PODCAST · business
$100M Exits with Jason Kirby
by Jason Kirby
In this podcast, we uncover the untold stories of founders who have weathered the highs and lows of raising capital. We go beyond the headlines and Techcrunch funding news articles to explore the uncharted territories of the fundraising landscape.In each episode, we'll sit down with founders from various industries who have raised venture capital to bring their visions to life. They'll open up about their personal journeys, fundraising tactics & more.If you're a founder, this podcast offers a ton of value & insights you can apply to your fundraising journey. Don't forget to hit subscribe!
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EP 114 | What Founders Get Wrong After Making Millions From an Exit
He built a company, sold it, and suddenly had millions in the bank. Here’s what no one tells you about what comes next. He bootstrapped a health tech SaaS company for 10 years and sold it to Agilent Technologies.Sriram Gollapalli went from grinding as a founder to managing millions overnight—and realized that making money and managing money are two completely different games.In this episode, he breaks down what founders don’t expect after an exit: the pressure of sudden wealth, the trap of overthinking investments, and why so many founders freeze when cash is just sitting in the bank. He shares how choosing the right buyer goes beyond valuation, why culture fit matters more than most realize, and the biggest mistakes he sees founders make when trying to invest in their exit.If you’re a founder building toward an exit—or already have one—this is the side of the journey no one prepares you for.What you’ll learn in this episode:How Sriram bootstrapped and exited his company after 10 yearsWhy culture fit matters more than price in an acquisitionThe biggest mistake founders make when cash hits their bank accountWhy trying to time the market can cost you millionsThe difference between being a great founder and a great investorWhy many founders hesitate to spend on themselves—even after a big exitHow to think about diversification beyond just stocksWhat most founders get wrong about managing wealth after liquidityRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=EP+114&utm_campaign=%24100M+Exits Get the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+114&utm_campaign=%24100M+ExitsHere's what you're in for: 00:00 Welcome and Guest Intro00:40 Building iLab Bootstrapped01:15 Running the Sale Process02:12 Choosing Agilent and Deal Terms04:24 Culture Fit and RSU Earnouts08:03 Deal Lessons and Next Steps10:22 Managing Money After Exit13:29 Founder DIY vs Advisors16:42 Biggest Post-Exit Mistakes23:51 Why Long Angle Exists27:10 Inside the Community Offerings30:11 Diversification and Private Markets39:33 Founder vs Employee Behaviors43:45 Advice for Newly Liquid Founders47:37 How to Join and ClosingABOUT SRIRAM GOLLAPALLI Sriram Gollapalli is a former tech founder and investor. He co-founded iLab Solutions, a health tech SaaS company he bootstrapped for over a decade before selling to Agilent Technologies. After his exit, he shifted his focus to investing and is now the co-founder of Long Angle, a private community for high-net-worth individuals focused on wealth, investing, and life after liquidity. You can reach out to Sriram through:LinkedIn: https://www.linkedin.com/in/sriramg/Email: [email protected] ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 113: The Truth About “Free” Investor Money
Most founders waste money right after raising it.Dipak Patel breaks down one of the biggest mistakes founders make after raising capital—hiring too fast and burning cash. Instead, the focus should be on using that money wisely and creating real value.His mindset is simple: treat every dollar like a loan. Even if it feels like free money, it comes with expectations. The best founders stay lean, hire carefully, and focus on efficiency before scaling.Rather than rushing into expensive senior hires, Dipak shares why it’s better to bring in the right people, give them ownership, and let them help build smarter systems first.If you’re raising money or planning to, this episode is a powerful reminder that discipline,not spending,is what drives long-term success.What you’ll learn in this episode:Why most founders waste money after raising capitalHow to think about investor money the right wayWhy every dollar should be treated like a loanThe importance of staying lean early onHow to hire smart and build efficientlyHow to avoid burning cash too fast Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+113&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+113&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Guest Welcome01:17 Spending With Payback Mindset01:32 Staying Lean and Hiring Lessons01:40 Equity and Efficiency Goals02:01 Stay Lean as a Founder02:30 Why They Sold and Exit Mindset03:02 What Gato Built in PropTech03:49 Listening to CRE Pain Points04:32 Dashboards Tickets and Waste Data06:16 M&A Sale Mistakes and Advisors10:35 Founder Takeaways on Cash and Raises12:03 Life After Acquisition and Earnout Reality15:40 Post Exit Reset and New Chapter16:01 Learning Food Tech Sales at Fuda18:25 COVID Pivot and CloudKitchens Consulting19:46 Joining NAO and Choosing Equity22:39 Scaling NAO Starts With CAC23:14 Fixing Ad Spend Targeting24:03 Referral Engine That Closes25:44 Cookie Outreach Playbook29:47 From Cookies to Healthcare Pivot34:18 Where Health Tech Is Going38:33 Winners Losers and AI Risk42:31 Consolidation and Startup Survival45:46 ClosingABOUT DIPAK PATEL Dipak Patel is an LCRO and operator, and a SaaS revenue expert. He is a 2x exited founder and has helped drive over $232M+ in ARR across the companies he’s worked with.He specializes in building go-to-market strategies for VC and private equity-backed companies, helping them grow efficiently and scale revenue. Dipak is also an advisor and investor, known for his focus on capital discipline and smart growth.You can reach out to Dipak through:LinkedIn: https://www.linkedin.com/in/dipakrpatel/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 112: How He Built and Sold a $100M Startup Twice | Dan Rosenberg
He built a $100M creator platform—and sold it twice. Here’s what actually happens after the deal closes.Daniel Rosenberg, cofounder of Represent.com, shares how he helped creators and celebrities sell products without upfront cost using on-demand production. This removed the biggest barrier for creators: launching a business without upfront cost or inventory risk.In this episode, he explains how Represent grew by working with top talent, why they focused on fewer, higher-value creators, and the risks that came with scaling fast. He also breaks down what really happens when you sell a company—from long deal processes to post-acquisition challenges.Daniel also shares how the creator economy is changing. Today, creators don’t just want sponsorships—they want ownership and equity.What you’ll learn in this episode:If you’re building a startup or thinking about exits, this episode gives you real, practical insights.How creators sell products without upfront costWhy choosing the right market mattersThe risks of scaling through big dealsWhat actually happens during an acquisitionWhy many deals fall apartHow the creator economy is shifting toward ownershipRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+112&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+112&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Meet Daniel Rosenberg 00:49 Represent Origin Story03:07 Landing Big Talent05:26 Growth Engine Explained07:49 Mayweather Cash Drop10:06 Licensing With Major IP11:01 Affiliate Versus Celebrity Focus15:05 Custom Ink Acquisition18:18 Deal Terms And Earnout19:59 Diligence Distraction Lessons21:40 Post Merger Integration25:10 Selling To Cameo29:37 Cameo Integration Reality Check33:33 Why Dan Stepped Away35:51 Ownership Shift In Creator Economy38:20 Partnering With Creators40:57 Risks And Who Should Worry43:12 Resources And ClosingABOUT DANIEL ROSENBERG Daniel “Dan” Rosenberg is a founder and entrepreneur best known for building Represent.com, a platform that helped creators and celebrities sell merchandise without upfront cost.He scaled the company to a $100M+ exit, selling it to Custom Ink, and later helped lead another sale to Cameo.Today, he focuses on the creator economy through Material Group, where he works with creators to build businesses where they have ownership—not just sponsorship deals.You can reach out to Daniel through:LinkedIn: https://www.linkedin.com/in/danielrosenberg1/ Website: https://www.materialgroup.co/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too much cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 111: How Defense Tech Startups Get Funded | AI, Warfare, and Venture Capital with Brad Harrison @ Scout Ventures | EP 111
From building startups to backing the future of warfare, this episode covers what founders need to know about capital, defense tech, and AI.Brad Harrison, Founder and Managing Partner of Scout Ventures, shares how fast defense technology is evolving—and why selling into this space is harder than most expect.He explains how AI, drones, and autonomous systems are reshaping warfare, and why success requires more than a strong product—founders need the right networks, industry insight, and an understanding of government buyers.The conversation also covers how deals work in defense tech, what investors look for, and why choosing the right capital matters—especially when navigating government contracts.If you’re a founder, investor, or operator in AI, defense, or emerging tech, this episode offers a clear view on how to build and fund in this space.What you’ll learn:How operator experience shapes investment decisionsWhy defense tech innovation is acceleratingHow AI and autonomous systems are changing warfareWhy startups struggle with defense procurementWhat gets funded in defense tech todayHow to align with real government demandWhy networks and relationships matterWhat drives successful outcomes and exitsWhy understanding the end buyer is criticalHow capital strategy impacts growthRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+111&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+111&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Entrepreneur Journey01:55 Founder Support at Scout03:46 Army Futures Command Shift05:17 Ukraine Drone Autonomy Leap08:12 Why US Procurement Lags10:53 Key Defense Tech Domains12:43 GPS Denied Navigation15:17 Next Gen Wireless 6G18:44 Founder Goals and Focus20:43 Red Flags and Hard Calls23:57 What Gets Funded Now28:19 Vendor Lock Risks29:11 AI Security Threats30:31 Autonomy Changes Warfare31:50 Selling to the Pentagon32:27 RFPs, TRLs, and SBIRs35:48 Lobbying and Budgets38:28 Founder Insight Advantage41:16 Tomahawk Robotics Exit44:32 Defense Tech M&A Drivers49:39 Scout Fund Strategy51:53 Space Deterrence Vision56:32 Founder Upside and WrapABOUT BRAD HARRISON Brad Harrison is the Founder and Managing Partner of Scout Ventures, backing companies like ID.me, Voyager Space, and Tomahawk Robotics.A former U.S. Army Airborne Ranger and West Point graduate, he later studied at MIT Sloan, focusing on building new ventures.He has advised leaders at the White House and Pentagon on defense and innovation, and is now based in Austin, Texas.You can reach out to Brad through:LinkedIn: https://www.linkedin.com/in/bradharrison Website: https://www.scout.vc/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 110: From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital
From building and exiting companies to deploying capital at a $1.8B investment firm, George Alifragis has seen both sides—as an operator and now a private credit investor at Metropolitan.In this episode, he breaks down the transition from operator to investor, lessons from scaling a global tech company, and how that shapes how he evaluates businesses today.He shares what really drives EBITDA growth, what makes a company attractive to private equity, and why operators often misunderstand how investors think about risk, growth, and returns.If you’re a founder thinking about exits or capital, this is a clear inside look.What you’ll learn in this episode:What changes when you go from operator to investorHow George scaled a global tech company and drove EBITDA growthWhat makes a business attractive to private equity buyersThe key differences between big corporations and mid-sized companiesWhy growth operators thrive in different environmentsHow investors actually evaluate risk and opportunityLessons from exiting companies to TELUS and a PE-backed firmWhy understanding the capital strategy is critical for a founderRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+110&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+110&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Welcome and George Alifragis Intro00:57 Operator Exits and Track Record02:32 From Bell to Building Altima Telecom07:24 Why He Left Corporate Life10:43 Regulation That Forced an Exit13:56 Moving to Miami and a New Chapter15:17 Scaling to a Successful Exit16:53 From Operator to Investor21:43 Inside Metropolitan’s Investment Thesis25:14 The Power of an Operator Network27:01 The Operating Experts Model Explained27:52 The Fishing Holes Investment Strategy28:47 Building an Ecosystem Partner Network30:12 Activating the Network at Scale32:21 The Deal Flow Flywheel34:30 How Deals Get Done at Metropolitan37:45 Alternative Capital Explained39:22 Structuring Bespoke Hybrid Deals45:07 A Real Deal Structure Breakdown50:25 Lessons on Cost of Capital53:53 Final Thoughts and How to ConnectABOUT GEORGE ALIFRAGIS George Alifragis is a multi-time operator turned investor, currently at Metropolitan, a $1.8B private credit firm, bringing experience from scaling companies, driving EBITDA growth, and evaluating businesses through an investor lens.He previously served as CEO of a global tech company, leading growth and exiting to a private equity-backed firm, and was earlier part of a successful exit to TELUS, one of Canada’s largest telecom companies.You can reach out to George through:LinkedIn: https://www.linkedin.com/in/galifragis/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 109: Why Silicon Valley Founders Are Panicking About AI w/ Jessica Mah
Jess Mah has built, scaled, and backed companies across multiple waves of Silicon Valley—but what she’s seeing now is different.In this episode of $100M Exits, she explains why even unicorn founders are under pressure in the AI era, where success is no longer about headcount, hype, or old playbooks. AI is compressing execution timelines, raising the bar for traction, and making many traditional founder skills feel outdated.Jess breaks down why relevance, speed, and adaptability now matter more than funding or past wins—and why many experienced founders are struggling to adjust. She also shares how to build lean, AI-first companies, protect your edge, use relationships as market intelligence, and why micro-teams may outperform bloated organizations.If you’re a founder navigating AI disruption, fundraising pressure, and shifting rules of company building, this conversation is a sharp reality check.What you’ll learn in this episode:• How AI is creating pressure even among unicorn founders• Why relevance and speed now matter more than money or status• What founders must unlearn to stay competitive• Why lean teams and micro-teams can outperform larger organizations• How to use side projects to rebuild your AI instincts and leadership edge• Why protecting your information edge matters more than everRaising capital?Get a list of vetted VCs for FREE here:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+109&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+109&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Meet Jess Mah01:21 Silicon Valley Stress04:03 Money Versus Relevance06:12 AI is changing the game11:06 Founders React Poorly14:17 Lean Teams And Traction16:37 Funding Bar Keeps Rising19:33 Differentiation And Wedges22:15 Bias In Venture Funding28:43 AI As Equalizer31:30 Multi-Project Mindset33:56 Building Quietly In Public38:17 Networking As Market Radar42:19 Protecting Your Information Edge50:07 Side Hustles For Legacy Founders56:40 Micro Teams And Reorg Reality59:22 Leadership Reset And FarewellABOUT JESS MAHJessica Ma is a serial entrepreneur, investor, and venture builder known for launching and scaling multiple technology companies in Silicon Valley. She founded her first startup while still in college and scaled it to a nine-figure valuation after Y Combinator. Since then, she has founded and incubated more than 10 companies with combined valuations exceeding $1 billion. Today, she focuses on AI-driven ventures and shares insights on how AI is reshaping company building.You can reach out to Jess through:LinkedIn: https://www.linkedin.com/in/jessicamah/Website: https://www.mahway.com/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A.He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it.For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast.Be sure to subscribe and let me know who you want me to interview next.
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EP 108: Luxury DTC Founder Chris Wichert: Raising $20M, Surviving DTC Collapse & Turnaround Exit
Chris Wichert raised roughly $20M to build a modern luxury sneaker brand, pitching Koio as the “Louis Vuitton for millennials.” After business school, he moved to New York and secured investors, including the Winklevoss twins, Founders Fund, and the founder of Aldo, scaling through press, retail experiments, and premium positioning.Then COVID hit. Retail revenue disappeared. Demand for dress sneakers collapsed. By early 2023, Koio faced roughly -$3M EBITDA in a market where DTC multiples had compressed and fundraising slowed dramatically.In this episode, Chris shares how they reset the business: cutting 40% of SKUs, reducing headcount by 70%, going remote-first, closing most stores, and removing $3M in costs without sacrificing revenue, returning the company to profitability.He also breaks down their exit process: running 200+ buyer conversations, navigating last-minute tariff-related deal risk, and ultimately selling to a Miami family office.If you’re a founder navigating scale, crisis, or exit timing, this episode offers a candid look at capital strategy, cost discipline, and realistic decision-making.What you’ll learn:Why early fundraising is about vision, not just numbersHow retail experiments validated a luxury DTC brandWhat happens when DTC multiples collapseHow to cut millions in costs without shrinking revenueWhy founders delay tough restructuring decisionsHow to run a disciplined, proactive M&A processRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+108&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+108&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Meet Koio Founder00:59 Why Raise Early Capital04:43 Retail Growth Playbook08:55 COVID Shock and DTC Reset15:51 Turnaround and Investor Realignment29:19 Choosing a Full Sale30:24 Building the Buyer Universe33:26 Tariffs Shake the Deal39:43 Founder Realism Shift52:43 Capital Traps and Exit AdviceABOUT CHRIS WICHERTChris Wichert is an entrepreneur and operator best known as the founder of Koio, a digitally native luxury sneaker brand built on craftsmanship and modern positioning. After raising ~$20M in venture capital, he scaled the business through retail expansion and premium brand building before navigating COVID and the broader DTC market collapse. Facing compressed multiples and a shifting capital environment, Chris led a full operational reset — cutting costs, restructuring the team, and restoring profitability — before successfully exiting to a family office. He now speaks and advises on capital strategy, turnaround execution, and proactive exit planning.You can reach out to Chris through:LinkedIn: https://www.linkedin.com/in/chris-wichert1/Website: https://ccatalyst.co/ABOUT JASON KIRBYJason Kirby is co-founder of Thunder, a tech-enabled investment bank helping founders reach ideal outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building, having coached hundreds of entrepreneurs and transacted over $135M personally; Thunder has transacted over $200M+.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: equip founders with knowledge, inspiration, and guidance to navigate capital strategy by interviewing founders and investors who’ve done it. For most, a $100M+ exit is a dream; for others, cash flow or IPO matters. Founders doing over $5M in revenue benefit the most from this podcast.Be sure to subscribe and let me know who you want me to interview next.
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EP 107: He Pivoted to Survive—Then Sold to Victoria's Secret for ~$700M | Brian Ree
From near bankruptcy… to a $700M strategic exit. Here’s how it actually happened.Brian Ree built DailyLook into a premium AI-powered personal styling brand, nearly lost it in 2014, rebuilt it around ruthless unit economics and LTV, merged with Adore Me, and ultimately exited to Victoria’s Secret in a $700 million transaction.In this episode, Brian breaks down the real story behind the pivot that almost killed the company, the $40 styling fee gamble that saved it, how focusing obsessively on lifetime value created a defensible moat, and why relationships drive major exits.He also shares how DailyLook scaled from $30M to $140M post-acquisition, what it’s really like operating inside a public company, and why building a fashion brand is a decade-long grind, not a hype cycle.If you’re building in DTC, fashion, subscription, or thinking about a strategic exit, this is a masterclass in resilience, economics, and timing.What you’ll learn in this episode:How DailyLook built a premium styling subscription powered by AI + human stylistsWhy negative unit economics nearly killed the company in 2014The $40 pricing decision that turned the business aroundHow obsessing over LTV created a long-term competitive moatWhy most DTC brands fail to control CAC and retentionHow relationships led to the Adore Me merger and Victoria’s Secret acquisitionWhat it’s like scaling from $50M to $140M inside a public companyWhy building a fashion brand is a 10+ year commitmentRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+107&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+107&utm_campaign=%24100M+ExitsFor full episode shownotes and resources, view them here.
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EP 106: How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap
From raising $100M from SoftBank to shifting from “growth at all costs” to building a durable business, Kris shares the real story behind scaling Sendoso to over $100M in revenue.In this episode of $100M Exits, Kris walks through what it was actually like pitching Masayoshi Son over Zoom, deploying nine figures into aggressive hiring, then quickly pivoting when the zero-interest-rate era ended. He breaks down the hard decisions around efficiency, acquisitions, AI-driven sales automation, international expansion, and why building a 100-person advisory network became his secret weapon.This isn’t just a fundraising story. It’s a lesson in adapting fast, evolving as a leader, and making bold moves when the market shifts.If you're building toward nine figures in revenue — or trying to survive the jump from hypergrowth to operational discipline — this episode is packed with real-world insight.Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+106&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+106&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Welcome and Kris from Sendoso 00:36 How SoftBank found Sendoso 02:07 The call with Masayoshi Son 04:46 What Kris did after the $100M landed 09:20 Using AI to scale sales without more headcount 12:11 Switching from hypergrowth to efficiency 16:32 Why Sendoso bought competitors 25:58 Making the merger work day one 27:18 The integration plan that kept it on track 28:03 Who they kept and who they didn’t 28:46 The tech migration and what took longer 29:47 M&A advice for founders 31:00 Talking to competitors before you need to 33:15 Why Kris chose a co-CEO setup 38:49 How Sendoso expanded internationally 44:17 How Kris changed as a leader 49:24 The advisor network that became a cheat code 51:42 Wrap up and how to connectABOUT KRIS RUDEEGRAAPKris Rudeegraap is the Co-Founder and CEO of Sendoso, an AI-powered sending platform helping B2B companies create meaningful engagement through personalized gifts, swag, and eGifts. He founded the company after recognizing a gap in how sales and marketing teams build real connections, drawing from over a decade in software sales.Under his leadership, Sendoso has scaled globally with strong venture backing, driven by his belief that authentic, personalized experiences win in a digital-first world.You can reach out to Kris through:LinkedIn: https://www.linkedin.com/in/rudeegraap/ Website: https://www.sendoso.com/ Email: [email protected] JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M, and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 105: From CEO to Employee: The Hardest Pivot of a Founder’s Career
From building a booming business overseas to being forced to start over, this is the founder journey most people never talk about.James Rose built and scaled an online furniture company during a massive property boom in Eastern Europe—only to see it nearly collapse during the global financial crisis. After years as an entrepreneur, he was forced to swallow his pride, re-enter the job market, and rebuild through sales and leadership roles.In this episode, James shares the unfiltered reality of going from founder to employee—and back again. He breaks down how sales became his lifeline, why founders delay exit planning, and how those lessons led him to build Inflectiv Group, a platform acquiring and rolling up profitable, founder-led agencies.If you’re a founder thinking about scale, resilience, or engineering a meaningful exit, this conversation delivers clarity without the hype.What you’ll learn in this episode:Why most founders avoid the reality check needed to plan a real exitHow losing a business reshapes your view of risk, pride, and employabilityWhy sales is one of the fastest paths to rebuilding after a setbackThe biggest mistakes founders make when fundraising or delaying M&AHow minority roll-ups unlock value for founder-led service businessesWhat acquirers actually look for in profitable agencies todayRaising capital?Get a list of vetted VCs for FREE here:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+105&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+105&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Introduction and Guest Welcome00:17 James Rose’s First Business Venture02:07 The Impact of the Global Financial Crisis04:09 Transitioning From Founder to Employee11:21 Re-entering Entrepreneurship Through M&A15:29 Market Trends and Acquisition Strategies29:58 Advice for Founders on Valuation and Exits36:35 Where to Learn More About JamesABOUT JAMES ROSEHe is the founder and CEO of Inflectiv Group, an investment firm backing independent marketing and communications agencies through minority investments, growth capital, and strategic support—while allowing founders to retain autonomy and control.A serial entrepreneur, investor, and growth leader, James brings over 20 years of experience across media, technology, and M&A. He has created significant shareholder value in private equity–backed businesses by scaling revenue from £0.5M to £7M+ and building effective go-to-market strategies.He has also worked closely with product and development teams to commercialize innovative SaaS offerings, bridging product vision and market execution. Today, James applies this hands-on experience to helping agency founders scale sustainably through disciplined growth and smart capital partnerships.You can reach out to James through:LinkedIn: https://www.linkedin.com/in/jamesroseequitypartners/Website: https://www.inflectivgroup.com/ABOUT JASON KIRBYCo-founder of Thunder, a tech-enabled investment bank helping founders achieve ideal outcomes through capital strategy and M&A.A serial entrepreneur with four exits, Jason has decades of experience in fundraising, M&A, and business building. He has coached hundreds of founders and transacted over $135M personally, with Thunder exceeding $200M+ in completed transactions.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSThe goal of $100M Exits is simple: equip founders with the knowledge and guidance to navigate capital strategy by learning from founders and investors who’ve already done it.For some, the dream is a $100M+ exit. For others, it’s cash flow or IPO. Founders doing over $5M in revenue will benefit most from this podcast.Be sure to subscribe—and let me know who you want interviewed next.
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EP 104: The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar
Most founders fail for psychological reasons—not tactical ones.In this episode of $100M Exits, Jason Kirby sits down with Aram Attar, founder of The VC Factory, to unpack the hidden psychology shaping fundraising outcomes, VC decisions, and why smart founders keep repeating the same mistakes.With 15+ years advising founders, sitting on boards, and training venture capitalists, Aram shares a clear conclusion: most failures aren’t about intelligence, strategy, or effort—they’re about how decisions are made under uncertainty.They explore the difference between trying to win versus trying not to lose, how VC psychology impacts fundraising more than your pitch, the hidden risks in earnouts and partial exits, and why the strongest teams balance promotion- and prevention-focused thinkers.Subscribe & get our free investor/buyer list at https://thunder.vcKey TakeawaysWhy founders repeat mistakes—even after seeing others failTrying to win vs trying not to loseHow VC psychology shapes fundraising outcomesRisks in earnouts, partial exits, and misalignmentWhy balanced thinking drives better decisionsWhat you’ll learn in this episodeWhy a “5-year plan” often turns into a 20-year journeyHow VCs avoid the sunk-cost trap in bridge financingThe mindset frameworks behind outlier investment betsHow to spot “what can go right?” vs “how do I not lose?” investorsThe #1 mistake first-time fund managers make with fund sizeRaising capital?Get a list of vetted VCs for FREE:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode104&utm_id=%24100M++ExitsGet the latest fundraising insights:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode104&utm_id=%24100M++ExitsTimestamps:00:00 Introduction00:39 A 20-year journey to a $2.2B exit01:57 How VCs make decisions03:50 Investing in a Mexican retail company06:20 What mindset-based investing really means10:04 Behavioral insights every founder should know15:34 Research behind successful VC thinking23:43 Missed deals and costly VC mistakes24:20 How investment committees really work24:51 The champion rule in venture capital26:06 Inside the investment committee process29:37 Why founder empathy matters33:04 The power of honest communication36:28 How to evaluate emerging fund managers43:01 Advice for new fund managers46:29 Final thoughts and key resourcesABOUT ARAMAram Attar is a venture capitalist and founder of The VC Factory, focused on improving venture outcomes by shaping how investors and founders think, decide, and align. His work spans advising VC funds, CEOs, governments, and accelerator programs, with an emphasis on psychology, character, and long-term performance.LinkedIn: https://www.linkedin.com/in/aram-attar/Website: https://thevcfactory.com/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders navigate capital strategy and M&A. A serial entrepreneur with four exits, Jason has coached hundreds of founders and led transactions totaling $200M+ through Thunder.Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITS$100M Exits equips founders with the insight and guidance needed to navigate capital strategy through conversations with founders and investors who’ve already done it. Best suited for founders doing $5M+ in revenue.Be sure to subscribe and let us know who you want us to interview next.
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EP 103: Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque
From building a $100M software business to watching it fall apart—here’s what really happened.He built a software company from the ground up and scaled it past $100M in sales.Matthew Whyatt started his first tech business at 22—and learned the hard way what happens when growth, partners, and focus drift off course.In this episode, Matthew breaks down the real story behind scaling fast, losing focus, and the lessons that reshaped how he thinks about sales, leadership, and building sustainable companies. He shares why sales is the lifeblood of every business, how founder-led sales eventually breaks, and what it actually takes to build a repeatable sales culture.If you’re a founder navigating growth, sales, or scaling challenges, this conversation is full of hard-earned lessons.What you’ll learn in this episode:How Matthew scaled a software business past $100M in salesWhy diversifying too early can derail focus on your core businessHow misplaced trust and lack of verification can destroy a companyWhat breaks when a founder-led sales team tries to scaleHow to build a repeatable sales culture rooted in diagnosis, not pitchingRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+103&utm_campaign=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+103&utm_campaign=%24100M+ExitsHere's what you're in for:00:00 Introduction and Guest Welcome00:36 Starting a Business at 2201:14 Early Marketing Strategies01:57 Expansion and Diversification04:26 Challenges with Business Partners11:07 Boardroom Dynamics and Decision Making22:41 Sales Culture and Ethical Practices26:11 Opening a New Zealand Office27:28 Financial Troubles and Trust Issues29:04 Tax Problems and Internal Mismanagement30:06 Data Supplier Issues and Business Liquidation32:49 Rebuilding and Moving Forward37:45 Sales Strategies and Lessons Learned40:43 Advice for Founders on Sales Culture49:40 The Importance of Diagnosis in Sales55:42 Final Thoughts and Contact InformationABOUT MATTHEW WHYATTMatthew is a sales and go-to-market expert with over 25 years of experience in software and SaaS. He has built, scaled, and exited multiple software businesses and has been involved in more than $100M in tech sales.He is the founder of TechTorque, where he helps software and SaaS companies sharpen their strategy, improve their sales process, and build revenue-driving marketing engines.Matthew is also the host of The CEO and the Salesman, a podcast focused on practical lessons from founders and operators on what actually works in business.You can reach out to Matthew through:LinkedIn: https://www.linkedin.com/in/matthewwhyatt/ Website: https://techtorque.com.au/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 102: He Raised $76M With No Defense Tech Background | Nelson Mills Founder of VATN Systems
From VC intern to $76M raised, here’s how it really happened.He raised $76M in two years—without ever working in defense tech.Nelson Mills, co-founder and CEO of a fast-growing underwater defense startup. Shares how he went from a VC intern to leading a company building autonomous undersea vehicles and why the maritime defense space became the perfect opportunity. He breaks down how he validated the market, assembled a world-class team, and raised more than $76M across multiple rounds. What you’ll learn in this episode:How Nelson raised $3.5M pre-seed, $13M seed, and a $60M Series A as a first-time founderWhy fundraising looks easy from the outside—and why it isn’t the biggest mindset shift Nelson made going from VC to founderWhat he’d do differently if he had to raise again tomorrowWhy raising capital ≠ success (and what actually matters)Subscribe & get our free investor/buyer list at thunder.vc.Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode102&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode102&utm_id=%24100M++ExitsHere's what you're in for:00:00 Intro00:06 From VC intern to founder01:18 Finding the opportunity in underwater defense02:56 Technical challenges & innovations07:23 Building investor relationships10:57 Inside the seed round23:17 Hiring & talent strategy26:31 Competing in defense tech28:24 Customer-driven product thinking29:29 Why lobbying starts on day one32:49 Navigating government sales34:23 Capital strategy & funding options37:28 Scaling hardware & supply chain44:18 Building a company with family46:00 Nelson’s advice for defense-tech founders48:38 Final thoughtsABOUT NELSON MILLSNelson Mills is the founder and CEO of Vatn Systems, an underwater vehicle startup building some of the world’s lowest-cost, high-production UUVs. In just 15 months, he led the company from concept to TRL 7, raising more than $3.5M in venture capital and assembling a team pushing the boundaries of maritime tech.Before launching Vatn, Nelson led hull development at Pure Watercraft, a marine electrification company backed by over $170M in funding. He later moved into venture capital, with roles at Link Ventures, Lux Capital, and Global Founders Capital, giving him a unique lens on product development, capital strategy, and scaling deep-tech companies.Nelson holds both a BA and an MBA from Columbia University and brings a blend of engineering insight, founder grit, and investor perspective to everything he builds.You can reach out to Nelson Wills through:LinkedIn: https://www.linkedin.com/in/millsn/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 101: Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai)
Andrew D’Souza, ex-co-founder of Clearco and now Boardy.ai, explains how he went from building a billion-dollar FinTech company to creating an AI “super-connector” that changes how founders meet investors.Andrew breaks down why warm intros no longer work, how Boardy.ai sparked investor interest before he was even fundraising, and why real-time AI conversations may become the future of dealmaking. He also shares ideas on founder psychology, network effects, and the next chapter of AI-driven relationship building.What You’ll Learn in This EpisodeHow Andrew D’Souza raised $8M using an AI agent (Bordy.ai)Why the “warm intro” is dead — and what replaces itHow Clearco scaled to a $2.5B unicornWhy investors chase the same 50 deals (and what founders should do instead)A breakdown of what’s actually broken in fundraising todayThe mechanics of AI-driven dealflow, investor matching, and credibility buildingRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode101&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode101&utm_id=%24100M++ExitsHere's what you're in for:00:00 Introduction and Guest Welcome00:16 Using AI to Raise Funds01:11 The Evolution of Fundraising05:02 Clear Co: Building a FinTech Unicorn08:56 Transitioning from Clearco to AI18:37 The Birth of Boardy25:45 The Initial Growth Strategy26:23 Defining Bordy's Vision and Purpose27:23 Building a Horizontal AI Platform27:55 Achieving Network Effects and User Success Stories28:57 Experimenting with Investor-Founders Matching30:12 The Importance of Trust in Business Introductions31:41 Boardy's Unique Onboarding Process36:23 Future Plans: Monetization and Expansion47:54 The Role of AI in Human Relationships53:17 How to Connect with AndrewABOUT Andrew D’SouzaAndrew D’Souza is a veteran founder and tech operator best known for co-founding and leading Clearco, the company that transformed non-dilutive capital and funded 10,000+ startups with over $2.5B deployed. With a background in Systems Design Engineering from the University of Waterloo, Andrew now invests, advises, and serves as a visiting partner at HF0, helping high-potential founders scale faster and build category-defining companies.You can reach out to Andrew through:X: https://x.com/andrewdsouzaLinkedin: https://ca.linkedin.com/in/andrewdsouza Instagram:https://www.instagram.com/andrewdsouza/ Website:https://www.boardy.ai/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 100: The Earnout Trap: What This Founder Learned After Selling His Company
After 20 years of steady, bootstrapped growth, Eric Friedman sold his company, eSkill, an online skills testing platform used by employers worldwide.In this episode, Eric breaks down how he built a profitable SaaS business with no outside funding, ran three separate sales processes, and closed a deal with private equity in 2024. He shares what founders should know about earnouts, how to choose the right investment bank, and the red flags he learned to spot during M&A negotiations.If you’re a founder thinking about selling a bootstrapped company, this episode is packed with real lessons on timing, valuation, and life after the exit.⚡ What You'll Learn: Why most earnouts never get paid — and how to protect yourself.The hidden risks behind LOIs, retrades, and exclusivity windows.How a dev-shop equity arrangement fueled 20 years of bootstrapped growth… until it didn’t.How interest rate spikes in 2022 instantly destroyed a great LOI.Why Eric ran three processes before landing the final buyer.How to evaluate PE buyers and spot red flags during diligence.Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode100&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode100&utm_id=%24100M++ExitsHere's what you're in for:00:00 Introduction03:40 Choosing an Investment Bank06:22 Running the Sale Process15:42 Finalizing the Deal and Advice for Founders19:59 Evaluating Potential Bosses and Partners20:25 The Importance of Thorough Due Diligence21:34 Transparency in Negotiations23:22 Understanding and Negotiating Earnouts24:47 Post-Acquisition Transition35:39 Life After the Exit37:21 Final Advice for FoundersABOUT ERIC FRIEDMANEric Friedman is an accomplished startup CEO with over two decades of experience leading and scaling SaaS companies. As the founder and CEO of eSkill Corporation, he built the company from concept to successful exit—achieving 20 consecutive years of revenue growth without outside funding. Under his leadership, eSkill became a leader in the HR technology space, serving global clients such as PepsiCo, GE, Deloitte, Stanford University, Zappos, the United Nations, and the U.S. State Department.He brings deep expertise in lean operations, sustainable growth strategy, and product-market adaptation. His ability to lead through both stable and volatile market conditions has made him a trusted operator in the SaaS space. His approach blends strategic discipline with operational agility—adapting go-to-market models and product fit in response to shifting customer and market needs.You can reach out to Eric through:LinkedIn: https://www.linkedin.com/in/eric-friedman-604258/ ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it.For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 99: From Zero to $10B in Secondaries: Greg Brogger 's Journey to a $160M Exit
In this episode, we break down how founders and early employees can get liquidity before an IPO—without selling shares, triggering taxes, or relying on a shaky secondary market. Our guest is Greg Brogger, founder of SharesPost (sold to Forge Global for $160M, later taken public and acquired) and now CEO of Collective Liquidity.Greg is one of the earliest architects of the private stock market, with over $10B+ in transactions. He covers:Why founders often wait too long for personal liquidityThe hidden risks of SPVs and secondary marketplacesHow to diversify equity without paying capital gainsWays to create a “financial floor” while still buildingHow exchange funds work—and why top founders use themIf you’re a founder, operator, or employee with meaningful equity, this episode shows how to unlock liquidity and reduce personal risk well before an exit.Raising capital?Get a vetted list of VCs: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=EP+99&utm_campaign=%24100M+ExitsFundraising insights: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=EP+99&utm_campaign=%24100M+ExitsEpisode Guide:00:00 - Selling SharesPost01:04 - COVID-19 challenges01:51 - Broker dealer model shift03:45 - Merger vs acquisition07:04 - Fundraising dynamics11:14 - Building SharesPost16:54 - Employee liquidity pushback19:28 - SPVs & market health23:13 - Nasdaq joint venture29:47 - Strategic moves31:11 - JV dynamics32:32 - Growth & COVID impact34:53 - Timing in venture37:07 - Founding Collective40:04 - Exchange funds46:21 - Liquidity strategies50:50 - Advice for founders57:43 - Key takeawaysAbout Greg BroggerGreg Brogger pioneered private-market trading as the founder of SharesPost, later merging with Forge. Before that, he helped build the Nasdaq Private Market and co-founded TrueCar and Internet Brands. He began his career as a securities attorney at Wilson Sonsini and holds degrees from UC Berkeley, UPenn Law, and Wharton. He currently serves on the board of Ownera.LinkedIn: https://www.linkedin.com/in/gregbrogger/Website: https://www.collectiveliquidity.com/About Jason KirbyJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders navigate fundraising and M&A. He’s a serial entrepreneur with four exits and over $135M in transactions.Email: [email protected]LinkedIn: https://www.linkedin.com/in/jasonrkirby/About $100M ExitsThis podcast helps founders navigate capital strategy, funding, and M&A through conversations with those who’ve done it. Best suited for founders doing $5M+ in revenue. Subscribe and share who you’d like to hear next.
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EP 98: How Andrew Ackerman Scaled DreamIt Ventures & Made 70+ Startup Bets
What really happens when a founder crosses the table to become an investor?In this episode, Andrew Ackerman, former Managing Director at DreamIt Ventures and author of The Entrepreneur’s Odyssey, joins Jason to discuss what he has learned backing more than 70 startups across ed-tech, prop-tech, and beyond.Andrew shares how he went from writing angel checks that disappeared to running one of the top accelerators in the U.S. He breaks down what founders get wrong about “value-add” programs, how he built a deal-flow system that attracted over 1,000 startups for just 12 spots, and what separates truly scalable founders from the rest.He also breaks down how to spot real accelerator ROI, why most programs aren’t worth it, and how experienced founders think differently about equity, advisors, and long-term value creation.Here’s what you’re in for:00:00 Introduction and Guest Introduction00:04 Andrew's Transition from Founder to Investor00:52 Early Angel Investment Experiences02:43 Joining DreamIt Ventures07:18 The Evolution of Startup Accelerators13:43 Selecting Startups for DreamIt26:15 Evaluating Startup Teams27:10 Switching Focus: From EdTech to PropTech32:17 Challenges in Accelerator Programs42:56 The Entrepreneur's Odyssey: A Novel Approach50:52 Connecting with Andrew AckermanRaising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode98&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode98&utm_id=%24100M++ExitsABOUT ANDREW ACKERMANAndrew Ackerman is a VC, SPV syndicate sponsor, and former Managing Director at DreamIt Ventures, with over a decade of startup investing and 70+ portfolio companies. A former founder turned investor, he’s built and scaled verticals in EdTech, PropTech, and ConstructionTech, creating DreamIt’s Customer and Investor Sprint programs to help startups raise capital and close enterprise deals faster. Andrew has advised CVCs, developers, and corporate innovation teams worldwide and published 60+ articles in Forbes, Fortune, AlleyWatch, and Propmodo.You can reach out to Andrew through:LinkedIn: https://www.linkedin.com/in/andrewbackerman/ Website: https://www.andrewbackerman.com/ Email: [email protected] (Subject line: “Fundraising Demystified Listener”)ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others, it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 97: From Startup Burnout to $100M Raise: Ron Reiter’s Redemption
He sold his Adtech company to Oracle after burning out, took it easy, then raised $100M+ for his next venture. Most founders dream of a big exit but few talk about what happens after.Subscribe & get our free investor/buyer list at thunder.vc.Key Takeaways:The emotional and mental cost behind selling Crosswise to Oracle.How burnout nearly ended Ron’s startup journey—and what pulled him back.The surprising truth about life inside a big corporation after acquisition.Why Sentra’s $100M+ raise was more about mission than money.Ron’s lessons on cofounder chemistry, resilience, and building without losing yourself.-------------------------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode97&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode97&utm_id=%24100M++ExitsHere's what you're in for:01:28 - Mental Health in Entrepreneurship02:55 - Starting the Podcast: Oracle Acquisition Journey03:32 - The Decision to Sell Crosswise09:29 - Navigating the Acquisition Process22:27 - Post-Acquisition Reflections and Retention28:26 - Market Dynamics and Strategic Decisions30:29 - Navigating Competitive Markets31:23 - The Catalyst for Starting Anew32:45 - Building with Friends and Finding Happiness35:25 - Defining the Right Role37:31 - Raising a Monster Seed Round42:25 - The FOMO Round and Series B Success49:28 - Investing in Founding Teams54:54 - Advice for Founders on Raising Money and Selling Companies58:06 - Final Thoughts and Wrap-UpABOUT RON REITERRon is a serial entrepreneur and cloud security expert known for turning complex technical challenges into scalable, real-world solutions. As the Co-founder and CTO of Sentra, he leads innovation in data security helping organizations regain visibility and control over their cloud environments.Before Sentra, Ron co-founded Crosswise, a cross-device identification company that bridged digital identities across devices and was later acquired by Oracle for $50 million.With over two decades in software development and more than six years as an Engineering Director at Oracle Data Cloud, Ron managed the Tel Aviv R&D branch and led initiatives across ID graph, DMP, audience, and contextual data products. His career reflects a deep commitment to building secure, intelligent systems that power the future of data-driven organizations.You can reach out to Ron through:Website:https://www.sentra.io/ Linkedin:https://www.linkedin.com/in/ronreiter/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 96: Inside the War Room: How to Manage a Company Crisis w/ David Meadvin
What do you do when your company is on fire, literally or figuratively?What do you do when the deal is days away from closing — and your company’s reputation explodes overnight?In this episode, David Meadvin, CEO of One Strategy Group, breaks down what really happens in the “war room” when crisis hits and how to protect your credibility, investors, and valuation when everything’s on fire.Subscribe & get our free investor/buyer list at thunder.vc.💡 Key Takeaways:Why reputation capital is a real currency during dealmaking.How to recover from a PR disaster before it kills your valuation.The difference between damage control and trust rebuilding.Tactical playbook for founders facing internal or public crises.How to stay calm when everyone else is panicking.Timestamps:04:22 - Navigating an IPO Crisis08:49 - Frameworks for Crisis Management11:50 - Handling Political and Social Issues16:47 - Personal Crisis Stories and Lessons20:26 - Decision-Making in Crisis Situations23:58 - Navigating Stakeholder Reactions24:37 - Building Trust with Investors25:12 - Handling Crisis Situations27:18 - The Importance of Communication29:21 - David's Career Journey30:39 - Advise for CEOs and Founders35:06 - The Role of Politics in Business38:58 - Final Thoughts on Crisis Management51:47 - Maintaining Mental Health as a Founder-------------------------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode96&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode96&utm_id=%24100M++ExitsABOUT DAVID MEADVINDavid Meadvin is the CEO and founder of One Strategy Group, a leading corporate and executive communications firm. With experience spanning both the public and private sectors, he’s advised Fortune 500 CEOs, political leaders, and top executives on high-stakes strategy and reputation management.Before founding One Strategy Group, David served as President of Laurel Strategies and held senior communications roles at Citadel, Bloomberg LP, and Facebook. In government, he was Chief Speechwriter for the U.S. Senate Majority Leader and Director of Speechwriting at the U.S. Department of Justice.Named to Washington Business Journal’s “40 Under 40”, David is recognized as one of America’s leading voices in executive communications, with work featured across major global media outlets.You can reach out to David through:LinkedIn:https://www.linkedin.com/in/meadvin/ Website: https://www.onestrat.com/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 95: How to Sell Your Startup: The Founder’s M&A Playbook
Most founders sell the wrong way. Here’s how to do it right.📣 Subscribe & get our free investor/buyer list at https://web.thunder.vc/vc-investor-listWhat you’ll learn in this episode:Forget the unicorn dream. This is how real founders achieve life-changing exits. Jason Kirby and Oliver Low — partners at Thunder — break down how to navigate the M&A process from both sides of the table: when to sell, how to structure a deal, and what to avoid when your future is on the line.🔥 3-6 Tactical Takeaways:Why timing your exit matters more than valuationHow to avoid the #1 killer of founder wealth: earnoutsThe rise of private equity buyers and what it means for startupsHow “venture orphans” can still create massive outcomesWhat Thunder looks for before taking founders to marketWhen Oliver Low sold his startup, it wasn’t a clean, overnight success story.It was years of building, negotiating, and learning the hard way how M&A really works.His company, Platform 360, eventually became part of a public company listed on the London Stock Exchange but the journey there was anything but straightforward.There were earnouts that didn’t go as planned.Buyers who vanished mid-deal.And market conditions that turned every negotiation into a gamble.For founders considering an exit or just trying to understand how real M&A unfolds — this conversation is a masterclass in playing the long game.Want more insights? Check out the full shownotes for Episode 95! HERE
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EP 94: I Bet My Entire Net Worth on Life360 — It Paid $8B Later
When Itamar Novick joined Life360, it wasn’t the family safety app we know today. The team was small. The product was rough. The future? Uncertain.Then came the moment that would define everything: 👉 The company was out of cash.👉 Investors were skeptical. 👉 Itamar had a choice — walk away or double down.He chose to bet his entire net worth on the company.That all-in moment eventually led to one of the most unique IPO journeys in tech — first in Australia, then on the NASDAQ. The risk paid off. Life360 became an $8B household name.In our new $100M Exits episode, Itamar shares:What it really takes to bet on yourself at scaleHow he managed acquisitions and integration while prepping for IPOWhy the hardest part of raising $200M wasn’t the moneyFor founders thinking about scaling beyond survival, this story hits hard.Here’s what you’re in for:01:41 From employee to cofounder and the leap that changed everything05:37 Raising capital when everyone says no06:21 Why big risky swings are the only way to win08:21 Scaling Life360 from idea to household name22:17 Acquiring startups and merging top talent37:48 Behind the IPO curtain and the tough calls nobody talks about40:41 Taking the leap to go public43:06 Why they chose Australia for the IPO44:47 Making the move to NASDAQ48:18 Founding Recursive Ventures and the next chapter52:02 Investing in the future with AI and founder-first thinking59:52 Hard-earned wisdom every founder should hear01:01:15 Getting funded with Recursive Ventures01:07:14 Final reflections and where to connectLooking for capital or to sell your company?Get a list of vetted & relevant Investors for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode94&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode94&utm_id=%24100M++ExitsABOUT ITAMAR NOVICKItamar Novick is the founder and solo GP of Recursive Ventures, a pre-seed fund backing startups in fintech, AI, and emerging tech. With experience as a founder, operator, institutional VC, and angel investor, he’s seen the startup journey from every angle.Itamar has invested in and supported 50+ successful startups, including Deel, Honeybook, Placer, Credible (IPO), MileIQ (acquired by Microsoft), Automatic Labs (acquired by SiriusXM), Tile (acquired by Life360), SafeGraph, and Armory. He was named one of Business Insider’s Top 100 global seed investors.As an operator, Itamar helped scale Life360 from Seed to IPO, growing revenue to over $250M. Earlier, he was a founding team member and Head of Product at Gigya (acquired by SAP). LinkedIn: https://www.linkedin.com/in/itamarnovick/Website: https://www.itamarnovick.com/ABOUT JASON KIRBYJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A, and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 93: Building Europe’s Palantir: How Max Buchan Raised $20M to Launch Valarian
Europe’s next defense-tech giant is being built in London. Subscribe & get our free investor/buyer list at thunder.vcHow Max Buchan helped take CoinShares from $0 to $50M revenue to $1.5B IPO —without VC money.The insider story behind founding Valarian, the UK’s answer to Palantir.Raising $20M in seed funding to build dual-use infrastructure for governments and enterprises.The shift from crypto to defense tech and why “digital sovereignty” is the next trillion-dollar opportunity.How Valarian attracted elite talent from Palantir, Darktrace, and top U.S. defense innovators.Lessons for founders raising capital in deep tech and dual-use markets.—-----------------------------------------------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode93&utm_id=%24100M++ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode93&utm_id=%24100M++ExitsHere’s what you’re in for:00:00 – How CoinShares hit $50M revenue with no VC03:30 – The problem that sparked Valarian: cross-border data control06:00 – Pivoting from secure messaging to compliance infrastructure08:30 – Raising $11M pre-product and landing IQ Capital & Molten Ventures10:20 – Expanding to $20M total seed and U.S. strategic backers13:40 – How defense tech funding evolved post-Ukraine16:00 – Defining product-market fit for dual-use infrastructure18:00 – Recruiting Palantir and Darktrace execs to Valarian23:30 – Why the UK talent system lags behind the U.S.32:00 – Operating in stealth: why Valarian waited to go public35:30 – The hardware Pelican Case: Valarian’s deployable defense tech37:00 – Consolidation and M&A in Europe’s defense tech ecosystem39:00 – Advice for founders building category-defining companies----------------------------------------------------ABOUT MAX BUCHANMax Buchan is the Founder and CEO of Valerian, a company building next-generation digital infrastructure to solve global data sovereignty challenges.Before launching Valerian, Max was the first employee at CoinShares, where he worked directly with the co-founder and CEO. In just 18 months, CoinShares grew from an idea to over $55 million in revenue and nearly $2 billion in assets under management, expanding to almost 200 employees and later going public on the Nasdaq with a $1B+ valuation.His experience scaling CoinShares across London, New York, Paris, Stockholm, and Jersey revealed a growing problem—how international companies manage data across borders. That insight inspired him to start Valerian, focused on digital sovereignty and secure global infrastructure.Max holds a degree in History and Economics from the University of London and was named to the Forbes 30 Under 30 Europe list for Technology.You can reach out to Max through:Website: https://www.valarian.com/LinkedIn: linkedin.com/in/maxbuchanABOUT JASONJason Kirby is the Managing Partner at Thunder.VC and host of $100M Exits. He’s helped thousands of founders navigate capital raises, M&A, and exits, with a focus on tactical, data-backed strategies.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/
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EP 92: Why I Left My $500M Startup to Start Again — Shay Levi (Unframe AI)
He sold for $500M—then started all over again. Get our free investor/buyer list at thunder.vcWhy Shay Levi left NoName Security after its $500M sale to AkamaiHow he built Unframe AI and raised millions at a massive valuationThe mindset shift from cybersecurity to AI innovationWhat founders get wrong about timing their exitsLessons on capital efficiency and founder evolution after a big win----------------------------------------------------Looking for capital or to sell?Get a list of vetted investors and buyers for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode92&utm_id=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode92&utm_id=%24100M+ExitsHere’s what you’re in for:00:00 – Intro: From $500M exit to new beginnings02:15 – The Akamai acquisition story: what really happened05:40 – Why Shay left at the peak08:20 – The “LLM moment” that sparked Unframe AI11:10 – Founder reinvention: starting again after massive success14:50 – Raising at a huge valuation from day one18:30 – Cybersecurity vs AI: mindset and market lessons22:00 – What $500M taught Shay about building the next one25:10 – Advice to founders chasing their second act28:00 – Jason’s recap and founder takeawaysAbout $100M Exits $100M Exits is where founders and investors who’ve achieved $100M+ outcomes share raw, unfiltered lessons. Hosted by Jason Kirby, each episode dives deep into the psychology, strategy, and playbook behind 9-figure exits and the next wave of category-defining startups.About the Guest – Shay Levi Shay Levi is the co-founder and former CTO of NoName Security, which was acquired by Akamai for nearly $500M. After scaling one of the fastest-growing cybersecurity startups of the decade, Shay left to found Unframe AI, a new venture pushing the boundaries of AI infrastructure and reasoning systems. Known for his product-first mindset and calm precision as a technical founder, Shay is now building in one of the most competitive spaces of the decade.You can reach out to Shay through:Website: https://www.unframe.ai/LinkedIn: https://www.linkedin.com/in/shaylevi2/?originalSubdomain=ilEmail: leave a comment to get an introAbout the Host – Jason Kirby Jason Kirby is the Managing Partner at Thunder and host of $100M Exits, where he shares stories and lessons from founders who’ve raised, sold, or scaled to 9-figure outcomes. He’s an active investor and advisor to high-growth startups navigating capital and acquisition strategies.LinkedIn: https://www.linkedin.com/in/jasonrkirby/
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EP 91: How She Bought Back Her Company From Investors
Melinda Nicca shares her story of raising capital, building a cash flow machine and buying it back from her investors to give herself independence again. In this episode, Jason Kirby talks with Melinda Nicci, Founder and CEO of Body Collective Group, and she opens up about her path as a health tech entrepreneur. She shares how her women’s wellness platform grew to reach over 6 million users, the highs and lows of fundraising, and the tough negotiations required to regain control of her company through a share repurchase.Mel also talks about navigating investor relationships, launching new products, and the future of AI in wellness. Her story highlights resilience, strategic thinking, and the importance of understanding the investor landscape.----------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode91&utm_id=%24100M+ExitsGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode91&utm_id=%24100M+ExitsHere's what you're in for:00:32 Mel’s Background & Vision02:25 Building Body Collective Group09:02 Fundraising Lessons21:24 Product Development & Expansion22:30 Navigating Investors31:25 AI Wellness Coach Vision35:39 Negotiating Buyouts & Reclaiming Ownership51:11 Future Plans55:26 How to Connect with MelABOUT MELINDA NICCIWith more than 30 years of experience at the intersection of technology and global health, she has built AI-driven platforms that have reached over 6 million people in 130 countries. As the Founder & CEO of Body Collective Group, she created Bella AI, the world’s most advanced women’s health assistant, and pioneered digital wellness platforms including Baby2Body and MBODY.Consistently recognized among the Top 100 Most Influential Women in Technology, she is known for translating AI research into real-world health applications, forging global partnerships, and scaling businesses to successful exits. Her board leadership spans high-performance sports and technology, with expertise in audit, risk, and strategy.She is passionate about advancing women’s health, scaling AI for global health, and driving purpose-led innovation that balances commercial success with social impact.You can reach out to Melinda through:Website: https://www.baby2body.com/LinkedIn: https://www.linkedin.com/in/melindanicci/?originalSubdomain=ukABOUT JASONJason Kirby is the co-founder of Thunder, a tech-enabled investment bank helping founders reach their ideal target outcomes through capital strategy and M&A. He is a serial entrepreneur with four exits and decades of experience in fundraising, M&A, and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, M&A and business development. He’s transacted over $135M and his firm Thunder has transacted over $200M+You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT $100M EXITSMy goal is simple: to equip founders with the knowledge, inspiration, and guidance to navigate the labyrinthine world of capital strategy to take your company where you ultimately want it, by interviewing founders and investors who have already done it. For most, it’s a dream to sell for $100M+, but for others it’s too cash flow or IPO. Founders doing over $5M in revenue will benefit the most from this podcast. Be sure to subscribe and let me know who you want me to interview next.
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EP 90: Search Funds Demystified: How Jon Staenberg (Agate Hound Fund) Nets 35% Annual Returns
This week, I chat with Jon Staenberg founding partner of Agate Hound Fund, to unpack the real mechanics behind venture capital and search funds. From his early days at Microsoft, to founding a search fund that delivers 35% net annual returns, Jon pulls no punches. He warns, “Don’t go into venture until you’ve actually got a skill,” and breaks down the challenges of buying a company. We explore how grit, curiosity, and critical thinking separate founders who retire early from those who build enduring empires, and why the “comprehensiveness of change today is astonishing.” Whether you’re curious about launching a search fund, leveling up in VC, or simply hungry for insights, this episode will equip you with the tools and the mindset to raise your game.Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Spotify&utm_medium=Video&utm_campaign=Episode90&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Spotify&utm_medium=Video&utm_campaign=Episode90&utm_id=FundraisingDemystifiedPodcastWe explore:0:00 – Intro & Meet Jon Staenberg of Agate Hound Fund4:50 – “Microsoft was way beyond my expectations…”10:30 – “Don’t go into venture until you’ve actually got a skill”16:15 – Search Funds 101: “5% net annual return22:00 – “Buying a company is hard… it’s messy”28:05 – Why grit, curiosity & critical thinking win33:40 – The “retire early” myth vs. 60‑hour workweeks38:20 – AI & the comprehensiveness of change today42:10 – How to connect with JonABOUT JON STAENBERGJon Staenberg is the founding partner of Agate Hound Fund, a search‑fund vehicle focused on acquiring and scaling founder‑owned companies. Before launching Agate Hound, Jon spent over a decade at Microsoft, where he led product strategy and saw firsthand how engagement and inspiration fuel innovation. A veteran operator turned investor, he’s passionate about teaching entrepreneurs that “buying a company is hard,” but also demonstrating how a disciplined, skill‑based approach can generate 35% net annual returns. Jon holds an MBA from Stanford and advises several high‑growth startups on go‑to‑market and capital strategy.Get in touch with Jon:Website: https://www.agatehound.fund/Email: [email protected] ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 89: From Uber to Snap to AI: Ben Chiang on Raising Millions Then vs Now
In this episode of Fundraising Demystified, I sit down with Ben Chiang, the former head of Uber China and founder of Forma (acquired by Snap- yes, from Snapchat), to unpack his journey through hypergrowth, high-stakes fundraising, and strategic exits. Ben shares the realities behind building in chaotic markets, the truth about investor dynamics post-exit, and how founders can stay sane while chasing scale. We dive into the underrated benefits of QSBS (Qualified Small Business Stock), why consumer startups have it tougher than ever, and the unique marketing challenges of building AI products in today’s crowded landscape. Great watch if you’re curious about any aspect of building and exiting in tech.—---------------------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode89&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode89&utm_id=FundraisingDemystifiedPodcastWe talk:00:00: From Zero to 50 Million Weekly Rides: Uber China’s Blitzscale Playbook02:48: Why Market Fit Is Make or Break06:07: Timing, Relationships & the Hidden Rules of Fundraising08:58: Forma’s Acquisition by Snap: Behind the Deal11:57: Luck, Credit, and the Realities of Startup Success15:00: Negotiating from Leverage vs. Desperation26:13: Founders vs. Investors: What Changes After an Exit28:08: QSBS: The Most Underrated Tax Benefit in Startups30:27: How Stock Market Volatility Affects Founders32:11: Leaving Snap: Rediscovering Purpose33:43: The Messy Reality of Building and Marketing AI Products37:14: Fundraising Now vs. Then: What’s Actually Changed?40:57: Herd Mentality and the Modern VC Landscape44:07: What It Takes to Enjoy the Founder Journey47:00: Final Advice: Know What You WantABOUT BEN CHIANGBen Chiang is a veteran operator and founder best known for launching Uber in China and later founding Forma, a startup acquired by Snap. His experience spans scaling platforms in hypercompetitive markets, navigating complex acquisitions, and now building across multiple AI content ventures. Get in touch with Ben:LinkedIn: https://www.linkedin.com/in/benjaminchiang/Twitter: https://x.com/ben_chiang ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 88: How a Broken Leave Policy Led to a $30M HR Tech Startup w/ Jenniffer Henderson (Tilt)
60 pitches in 90 days. A Series B term sheet that collapsed. A $15M valuation hit, and she still came out on top.In this episode, Jennifer Henderson, founder of Colorado-based HR tech startup Tilt, breaks down exactly what it took to raise over $30 million in venture capital while balancing motherhood, market crashes, and investor whiplash.Jen shares how Tilt was born out of personal trauma, why she built a leave management platform with empathy at its core, and what every founder, especially women, needs to know before walking into their next pitch.From Techstars to term sheet disasters, this is the real story behind startup success in today’s market.—---------------------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode88&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode88&utm_id=FundraisingDemystifiedPodcastHere's what you're in for:00:00 – “I don’t come from money”: Why Jen chose venture04:21 – Building Tilt from personal pain06:08 – Sales tactics that worked09:07 – How Techstars changed the fundraising game11:53 – Raising Series A: Saying no to ‘cute’ term sheets18:03 – Series B nightmares: exclusivity traps, errors & resilience33:07 – The truth about AI in HR tech39:02 – Advice to female founders: “Be successful. We need you.”42:56 – Surviving the current startup market ABOUT JENNIFER HENDERSONJennifer Henderson is the founder & CEO of Tilt, a Colorado-based HR tech platform that simplifies and humanizes leave of absence management for modern teams. After two traumatic parental leave experiences, she turned her frustration into a mission. From Starbucks barista to corporate leader to raising $30M+ across five rounds, Jen's journey is a masterclass in resilience, grit, and founder-first leadership. Tilt is now a trusted solution for teams across the U.S., navigating complex leave policies with care.Connect with Jennifer on:LinkedIn: https://www.linkedin.com/in/jenniferhendersonjctcjcdcEmail: [email protected] JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 87: Customer Retention Over Acquisition? Travis Steffen, Who’s Done $200M in Deals, Says Yes
This week, I talk to Travis Steffen, who has built and sold eight companies. He’s raised over $100M and driven more than $200M in exits.In this episode, we delve into what actually drives startup growth and what quietly undermines it. We also get into how one bad exit almost wrecked him, and what he learned from losing years and seven figures because of one avoidable mistake.If you're a founder, operator, or even just thinking about building, this episode will give you a clearer view of what’s worth your attention.—-------------------------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode87&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode87&utm_id=FundraisingDemystifiedPodcastWe get into:00:00 The Real Startup Journey: No Filters, No Hype03:07 Why "Never Quit" Is Holding You Back05:47 Churn: The Growth Killer Founders Ignore09:12 What You Learn When a Startup Fails12:05 Retention Isn’t a Metric. It’s a Strategy.14:52 Why Investors Walk, Even If Your Numbers Look Good17:48 The Retention-Valuation Link You Can’t Ignore21:06 From Flatlined to $70M: A Turnaround Breakdown34:37 How We Built the Most Trusted Brand in a Broken Industry36:19 Revatto: Built to Solve Churn Without Adding Work40:07 No Results, No Cost: A Different Kind of Retention Model42:29 How To Save Customers, Without a Product Tutorial45:10 You Probably Don’t Understand Your Churn. Here’s Why.47:24 How to Test Revatto, with $1,000 in Free Recoveries51:21 One Retention Habit That Changes the Game54:24 The Exit That Went Sideways, and What It Cost ABOUT TRAVIS STEFFENTravis Steffen is a founder, operator, and builder with a track record most founders never reach. He’s exited eight companies, raised more than $100M, and led over $200M in M&A. His work spans SaaS, cannabis tech, fintech, and AI. Today, he’s the co-founder of Revatto, a company that helps subscription-based businesses retain more customers and only charges when it works.Check out Revatto: https://www.revatto.com/ ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 86: What Founders Get Wrong About Exits (and How John Rood Got It Right)
Most founders dream of a life-changing exit. But few actually prepare for it, until it’s too late.In this episode of Fundraising Demystified, I sit down with John Rood, an exited founder who scaled a tutoring side hustle into a global edtech business, and sold it for over eight figures to private equity.John also shares the story behind his book Beyond the Exit and why post-exit life is often not what you think it will be.----------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode86&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode86&utm_id=FundraisingDemystifiedPodcastWe talk:00:00 – The Brutal Truth No One Tells Founders02:04 – How John Turned Tutoring into SaaS Gold05:21 – The Finance Hack That Boosted His Valuation07:10 – What Really Kicks Off an Exit11:08 – The $10M Mistake Founders Keep Making13:59 – What’s Actually Enough for You?17:01 – Why Most Founders Regret Life After Exit22:52 – Angel Investing: The Ego Trap No One Admits28:22 – The Weirdly Happy Knife Founder Story-----------------------------------About John RoodJohn Rood is the author of Beyond the Exit and the founder of one of the world’s leading pre-med test prep businesses. After scaling the company into a content-and-software powerhouse, he exited for over eight figures to a private equity firm. He now advises founders on exit strategy and post-exit reinvention, drawing from both his wins and the emotional landmines no one warns you about.Connect with John: LinkedIn: https://www.linkedin.com/in/johnrood1/Get the book: https://www.beyondtheexitbook.com/
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EP 85: From Burnout to Breakout: How Jennifer Tsai Bootstrapped Shoott.com to $10M After Raising $2.7M
What happens when you raise $2.7M... then realize you never want to raise again?Jennifer Tsai, founder and CEO of Shoott.com, built a profitable photography marketplace from the ground up; surviving death threats from creatives, a brutal CAC spike post-iOS14, and the chaos of marketplace economics. In this episode of Fundraising Demystified, we dive into how she scaled to $10M in revenue, hit breakeven, and is now facing the “what’s next” moment many founders dream of, or dread.Whether you're building a two-sided marketplace, wrestling with capital strategy, or wondering how to survive without more VC cash, this one's for you.Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode85&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcastIn this episode, you'll learn:00:00 – Death Threats, Disruption & The Origin Story of Shoott.com05:45 – Why Creatives Hated Us And How We Won Them Over12:08 – From $80K to $10M: The Fundraising + Growth Playbook17:52 – How We Hit Profitability (And 20x’d It)21:26 – Cash Flow Roulette: Paying Creators Before Clients Pay Us22:57 – The $300K Mistake That Nearly Sank Us25:57 – Should You Raise, Sell, or Stay the Course?27:32 – The Brutal Truth About Valuations in Today’s Market30:38 – Founders: Before You Build a Marketplace, Watch This
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EP 84: David Connors Used The Swarm to Raise Millions | Deal Flow, M&A, and Warm Intros
This week on Fundraising Demystified, I sat down with David Connors, founder of The Swarm, a Go-To-Network platform transforming how founders and investors connect- think LinkedIn but for companies.David shares how he used The Swarm to raise capital for his own startup, how the product helps other founders close rounds, and what he learned from working at Sequoia.Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcastSign up to get 70% off the Swarm: theswarm.com/thunderHere’s what you’re in for:00:42 - Who is David Connors and what is The Swarm?02:08 - How working at Sequoia birthed The Swarm05:32 - Raising The Swarm’s $2M pre-seed round solo (and why it was capped)11:37 - Raising a $4M seed and scaling a building a winning team14:31 - How to find investors and pick the right ones for follow-on funding18:52 - Getting warm intros for investor outreach in minutes22:28 - The best kind of warm intros ranked25:43 - Why Swarm raised an extension round29:10 - The shift from SaaS to data, 10xing revenue and getting Hubspot Ventures to invest32:40 - Vibe coding and AI tools that support The Swarm’s scale35:02 - Top tips for personal branding that boosted growthCheck out the pre-seed investment memo for The Swarm here: https://docs.google.com/document/d/1wzo0PxFCyNgaD627-e2q2wefV0LUk4DJjnEr3R4b07k/edit?tab=t.0ABOUT DAVID CONNORSDavid Connors is the founder of The Swarm, a Go-to Network platform that helps startups access warm intros to capital, talent, and strategic partners. A second-time founder with deep experience in startup M&A, David previously built a company acquired by Levels, a Sequoia-backed health tech firm. With a background in enterprise sales and operations, he built The Swarm to solve one of the hardest problems founders face: getting in front of the right people without wasting time on cold outreach.Connect with David via:LinkedIn: https://www.linkedin.com/in/connorsdavidWebsite: http://theswarm.com/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thanks for tuning in! We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.#startupfunding #venturecapital #theswarm #founderstories #fundraisingdemystified #saas #data #investoroutreach
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EP 83: Jess Loren on Digital Twins & Unconventional Strategies of Raising Capital as Female Founder
In this episode, Jess Loren, founder and CEO of Global Objects, shares her journey on raising capital as a female founder, including turning down a $20M offer and building her business using digital twins technology.Jess dives into how she's building a tech company rooted in culture, purpose, and innovation, while navigating the fundraising landscape as a female CEO. We talk about generative AI in media, managing a startup as a mom, building a tech community, and how to use AI to boost productivity.A great story about leadership, innovation, and startup resilience.—-------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode83&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode83&utm_id=FundraisingDemystifiedPodcastHere's what you're in for:00:00 - Intro00:35 – Raising Capital as a Female Founder: Intro to Jess Loren & Global Objects03:06 – Building a Tech Community in LA06:05 – Balancing Life as a Female CEO08:42 – Digital Twins Technology for Culture & Innovation13:16 – Using AI to Boost Productivity in Creative Industries16:34 – Generative AI in Media & Entertainment22:18 – Jess Loren’s Journey: From 2X Exit Founder to Building Global Objects25:47 – Funding Strategies & Investor Alignment28:16 – Global Objects' Mission and Growth Plan31:30 – Startup Leadership as a Female CEO34:05 – Jess Loren on Persistence, Boards & Building Visibility ABOUT JESS LORENJess Loren is a 2X exited founder and the CEO of Global Objects, a cutting-edge startup at the intersection of digital twins technology, cultural preservation, and generative AI. With a background in community building, immersive experiences, and Web3 innovation, Jess is known for her bold leadership, fundraising acumen, and vision for reshaping how we digitally capture and interact with the world. Her journey includes turning down a $20M term sheet to stay mission-aligned, proving that purpose and persistence can coexist at scale.You can reach out to Jess through:LinkedIn: https://www.linkedin.com/in/jessloren/Global Objects' LinkedIn: https://www.linkedin.com/company/globalobjects/ ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 82: How to Build a Startup Advisors | Barry Stamos of Supernova on Scaling & Managing Advisors
Startup Advisors can make or break your growth. In this episode, Barry Stamos of Supernova shares how to build a world-class startup advisory board, manage relationships, and scale successfully.With real-world lessons from the Tuft & Needle journey and his advisory platform Supernova, Barry dives deep into sourcing the right advisors, setting success metrics, avoiding red flags, and aligning compensation with performance.—------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode82&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode82&utm_id=FundraisingDemystifiedPodcastHere's what you're in for: 00:00 – Introduction00:08 – Meet Barry Stamos: Founder of Supernova00:43 – Barry’s startup journey and lessons from past exits03:10 – Why startup advisors and mentors are critical03:29 – Finding and managing startup advisors effectively05:29 – Startup advisor success story: learning from experience08:56 – The right time for early stage startup support12:26 – Tuft & Needle case study: startup advisor success story16:04 – The real role of startup advisors in startup growth20:33 – Managing advisor relationships for success21:27 – How to compensate startup advisors effectively23:53 – How to find startup advisors and sourcing advisors for startups25:55 – Making aggressive advisor requests29:16 – Startup advisor horror stories and startup advisor red flags33:05 – Introducing Supernova: the startup advisor platform35:44 – How Supernova matches advisors with founders37:51 – Advice for founders seeking advisors and building a startup advisory board40:00 – How to connect with Barry Stamos and Supernova —---------------------------ABOUT BARRY STAMOSBarry Stamos is a 3x exited founder, startup advisor, and CEO of Supernova—a platform that connects high-growth startups with a curated network of successfully exited founders. With a track record that includes advising breakout companies like Tuft & Needle, Barry specializes in helping startups scale smarter through strategic advisory boards, hands-on mentorship, and performance-driven advisor relationships.You can reach out to Barry through:LinkedIn: https://www.linkedin.com/in/bstamos/Supernova's Website: https://1supernova.com/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 81: IPO Market Trends 2025: Best Time to Go Public w/ Peter Goldstein | IPO Valuation & Readiness
This week, I host IPO market expert Peter Goldstein, who talks about the best time to IPO, how to position for strong IPO performance, what true IPO readiness looks like, and how companies are being valued in 2025.If you're a founder eyeing the public markets, this is your roadmap. We dive into shifting investor sentiment, the surge in the secondary market, and strategic insights on when to go public, build public company credibility, and leverage equity in IPOs to your advantage.______________________________________________________________Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode81&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode81&utm_id=FundraisingDemystifiedPodcastHere's what you're in for:00:00 – The 2025 IPO market02:15 – Investor sentiment in the current IPO climate04:40 – Why IPO timing is critical: the best time to IPO07:25 – IPO valuation expectations and market sensitivities10:05 – IPO readiness checklist for founders12:50 – What happens after IPO: risks and surprises16:15 – IPO performance in 2024 vs 202519:30 – Market cap requirements for IPO explained22:10 – How equity in IPO impacts control and growth25:20 – Benefits of going public beyond capital28:05 – Public company credibility and strategic advantages31:15 – The rise of the secondary market and investor access34:30 – Private stock trading trends and access to liquidity37:20 – When should you go public?40:10 – Employee stock incentive strategies in public companies43:30 – Parting shot from Peter GoldsteinABOUT PETER GOLDSTEINPeter Goldstein is a leading expert in the IPO market, founder of Exchange Listing LLC, and author of The Entrepreneur’s IPO. With decades of experience guiding small and micro-cap companies through public offerings, Peter is known for helping founders navigate the complexities of going public. His deep understanding of IPO readiness, valuation, and investor strategy makes him one of the most trusted voices in the space.You can reach out to Peter through:LinkedIn: https://www.linkedin.com/in/peter-goldstein-exchangelisting/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 80: JC Glancy’s Unicorn Startup ZenBusiness From Credit Card Debt, Gave Up CEO, Hit $1B Valuation
JC Glancy, co-founder of ZenBusiness, shares his remarkable unicorn startup journey, from nearly drowning in credit card debt to building a billion-dollar startup. In a bold and rare move, he gave up the CEO title early on but still led the company to raise a $200M Series C and dominate the legal tech space.This episode dives deep into startup realities: raising venture capital, overcoming failure, building an unbeatable team, outmaneuvering big competitors like LegalZoom, and scaling ZenBusiness through SEO, affiliate marketing, and obsessive customer focus.______________________________________________________________Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode80&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode80&utm_id=FundraisingDemystifiedPodcastHere's what you're in for:00:00 – Intro: JC Glancy’s founder success story begins02:30 – Credit card debt & early startup struggles06:15 – Building ZenBusiness into a unicorn startup09:00 – Giving up the CEO title: The bold move12:50 – How ZenBusiness outperformed LegalZoom16:10 – Product market fit: Why the early products failed19:45 – The SEO and affiliate marketing funnel that scaled23:30 – Fundraising strategy: From angels to $200M Series C28:20 – Building a powerful startup team without resources32:10 – COVID pivot story: How ZenBusiness exploded in growth37:00 – Recruiting top talent post-Series C41:30 – Founder exit strategy: Why JC stepped back45:00 – What JC is building next + advice for future unicorn foundersABOUT JC GLANCYJC Glancy is the co-founder of ZenBusiness, a unicorn startup that helps entrepreneurs launch and grow their businesses. From maxed-out credit cards to a $1B valuation, JC’s journey is a powerful founder success story. As head of product marketing, he built ZenBusiness’s marketing machine—driving explosive growth through SEO, affiliates, and data-driven customer insights. He gave up the CEO title, helped raise a $200M Series C, and led the company to outpace giants like LegalZoom.Connect with JC:LinkedIn:https://www.linkedin.com/in/jcglancy ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 79: How to Attract Influencers to Promote Your Startup: Celebrity Marketing & Influencer Deals Explained
In this episode, Gil Eyal of Stardust Ventures shares expert insights on celebrity marketing and influencer deals for startups. Learn how to pitch your startup to influencers, find the best platforms to connect, and structure celebrity deals, all without breaking the bank. Plus, discover the biggest mistakes startups make with influencer marketing and how to avoid them.----------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode79&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode79&utm_id=FundraisingDemystifiedPodcastHere's what you're in for:00:00 – Intro | How to attract influencers to your startup (Gil Eyal’s expert take)02:15 – The truth about celebrity marketing (Why celebs care about startups)05:30 – Biggest mistakes startups make with influencer marketing09:45 – How to get access to celebrities & influencers (Stardust Ventures' insights)13:20 – The power of storytelling in influencer marketing (Why authenticity wins)17:05 – How to pitch your startup to influencers (Gil Eyal’s step-by-step strategy)20:50 – Best platforms to connect with influencers (Where to find the right talent)25:10 – How to structure influencer & celebrity deals (Equity vs. cash agreements)29:40 – How celebrity partnerships impact startup valuations (Real success stories)35:00 – The most effective marketing channels for startups (Gil Eyal’s top picks)39:00 – B2B vs. B2C influencer marketing (How to make it work in different industries)43:00 – Final advice from Gil Eyal on startup growth & fundraisingABOUT GIL EYALGil Eyal is a leading expert in celebrity endorsements and influencer marketing, known for revolutionizing how brands leverage data-driven influencer strategies. As the Founder and former President of HYPR, he built the market leader in influencer marketing automation, which won multiple industry awards before being acquired by Juliusworks in 2020.A veteran of 200+ celebrity endorsement deals, Gil has worked with Leonardo DiCaprio, Serena Williams, Zendaya, Pitbull, and Stephen Curry, among others. Today, as the Founder of Stardust Ventures, Gil helps consumer startups scale through strategic celebrity partnerships.You can reach out to Gil through:Website Stardust Ventures: https://stardustventures.us/LinkedIn: https://www.linkedin.com/in/gileyal/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with four multi-million exits and decades of experience in fundraising and business building. In his career, he has coached hundreds of entrepreneurs on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 78: How to Make a Startup Successful, Founder Mindset & Startup Operations with Adam Spector of Chore
In this episode, I sit down with Adam Spector, CEO of Chore, to break down founder mindset, startup operations, and how to make a startup successful. Adam shares what separates successful startup founders from those who fail, covering topics like founder time management, startup productivity, outsourcing, and the best outsourcing tools for startups. We also dive into the reality of starting a business, common founder mistakes, and how to scale effectively. If you're a founder, investor, or entrepreneur, this is an episode you don’t want to miss!----------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode78&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode78&utm_id=FundraisingDemystifiedPodcastCheck out Chore: https://www.hirechore.com/partner/fundraising-demystified?utm_source=Podcast&utm_medium=Thunder_VC&utm_campaign=Fundraising+DemystifiedWhat to expect from this episode:00:00 – Why Founders Waste Time on the Wrong Things (and How to Fix It) 05:30 – The Brutal Truth About Startup Productivity Hacks 12:45 – How to Outsource Like a Pro and Scale Faster 18:20 – The Best Tools and Services to Automate Your Startup Ops 22:10 – The Harsh Reality of Starting a Business (What No One Tells You) 28:50 – The Biggest Mistakes That Lead to Founder Burnout and Failure 35:40 – The Ultimate Playbook for Making a Startup SuccessfulABOUT ADAM SPECTORAdam Spector is a 4-time founder, startup advisor, and investor with experience in scaling companies and optimizing startup operations. As the CEO of Chore, he helps founders and teams focus on what matters by providing fractional chief-of-staff services to streamline back-office work. Adam has invested in over 200 startups, giving him unique insights into why startups fail and what it truly takes to succeed.Chore Webiste: https://www.hirechore.com/Adam Spector LinkedIn: https://www.linkedin.com/in/adamspector2/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 77: How To Spot Massive Early-Stage Startup Trends With Katelyn Donnelly Of Avalanche VC
How do you identify and capitalize on the biggest upcoming trends?Katelyn Donnelly, GP of Avalanche Ventures, unveils her unique investment strategy focusing on "avalanches" – inevitable market trends driven by societal and technological shifts. In this episode, Katelyn shares her insights on what VCs look for in early-stage startups, emphasizing the importance of founders building their life's work and understanding the nuances of early-stage venture capital. ----------------------------------------------------Raising capital?Get a list of vetted VCs for FREE here:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode77&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode77&utm_id=FundraisingDemystifiedPodcastHere’s what you’ll find in this episode:00:10 Avalanche Ventures Thesis01:13 Identifying Market Trends04:04 KatelynDonnelly's Background06:28 Avalanche Ventures Investment Focus07:28 Examples of Avalanche Investments11:15 Solo GP Experience13:03 Evaluating Investment Opportunities14:41 Cold Emailing Advice for Founders19:29 Austin's Startup Ecosystem20:49 Venture Capital Insights28:17 Future Market Trends----------------------------------------------------ABOUT KATELYN DONNELLYKatelyn Donnelly is the Managing Partner of Avalanche VC, an early-stage venture firm that invests in technology companies transforming how people learn, earn, and own. Her extensive background includes co-founding Delivery Associates, a leading public sector advisory firm, and serving as Managing Director of Pearson Ventures, a global EdTech venture fund. Donnelly's career also features time at McKinsey & Company, and she has been recognized for her achievements, including being named to Forbes 30 Under 30. She is actively involved in shaping the future of education and technology, and is a member of Duke University's Learning Innovation Advisory Council.Connect with Katelyn:Katelyn's Website: https://katelyndonnelly.com/Avalanche VC Website: https://www.avalanche.vc/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: Jason KirbyABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 76: What VC Look For in Early Stage Startups with Dave Lambert Right Side Capital Management
Wondering what VCs look for in early-stage startups? In this episode, Dave Lambert, Managing Partner at Right Side Capital Management, shares insights on how to get funding for a tech startup, the importance of technical co-founders, and how to raise pre-seed capital while keeping control of your business.With over 2,000 investments, Dave reveals the fundraising strategies that work in 2025, common mistakes founders make, and why capital efficiency matters more than high valuations. ----------------------------------------------------Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode76&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode76&utm_id=FundraisingDemystifiedPodcastIN THIS EPISODE[00:00] Dave Lambert from Right Side Capital Management and Early-Stage Startup Investing[02:15] What VCs Look for in Early-Stage Startups[07:34] Fund Size and Unique Approach[15:40] Valuation Trends and Market Dynamics[07:34] RightSide Capital’s Unique Investment Strategy & Fund Size[15:40] Startup Valuation Trends & Market Changes|[17:29] AI’s Impact on Early-Stage Startup Investments[20:42] Fundraising Challenges & How Founders Can Overcome Them[27:36] Venture Capital vs. Bootstrapping: Choosing the Right Path[29:04] The Role of Transparent Communication in Startup Fundraising[31:18] How CEOs Should Manage Investor & Board Relations[36:13] How to Provide Investor Updates That Build Trust[43:36] Why Low Cash Burn is Critical for Early-Stage Startups[45:33] The Future of Early-Stage Venture Capital & Startup Funding[49:42] How to Connect with Dave Lambert ABOUT DAVE LAMBERTDave Lambert is the Founder and Managing Partner of Right Side Capital Management (RSCM), a venture firm specializing in early-stage startup investing. With over 2,000 investments, RSCM focuses on capital-efficient tech startups, making fast investment decisions at valuations under $4M.A former exited founder, Dave brings decades of experience in startup growth, fundraising strategies, and pre-seed investing.Connect with Dave:Right Side Capital Management Website: https://www.rightsidecapital.com/Dave Lambert LinkedIn: https://www.linkedin.com/in/davidlambert55/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: jasonrkirbyABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 75: Raising Capital & Selling a Startup for Millions – Jeremy Parker’s Swag.com Story
Jeremy Parker, co-founder of Swag.com discusses his incredible journey of building a successful swag business from scratch and ultimately selling it to Custom Ink. Jeremy shares valuable insights on raising capital, identifying market opportunities, and navigating the acquisition process.------------------------------------------Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode75&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode75&utm_id=FundraisingDemystifiedPodcastHere’s what you’ll find in this episode:00:19 How Swag.com got to $40 Million in Sales05:41 Wildest orders taken by Swag.com06:47 How Swag.com started15:35 Raising $3 Million in Venture Capital for Swag.com21:38 Getting Acquired by Custom Ink34:39 Advice for Founders36:55 Connect with Jeremy ParkerABOUT JEREMY PARKERJeremy Parker is the co-founder of Swag.com, a prominent e-commerce platform specializing in high-quality promotional products for businesses. His entrepreneurial journey began after graduating from Boston University, where he initially pursued film production. Parker's business background includes establishing a creative promotional product division and co-founding an e-commerce platform focused on social media influencer marketing, which was later acquired. He then focused his efforts on Swag.com, which has seen rapid growth and attracted major clients like Facebook, Google, and Amazon. Notably, Swag.com was acquired by Custom Ink in 2021. Parker has also been recognized for his achievements, including being named to Crain's NY 40 under 40, and Swag.com has appeared on the Inc. 500 list of fastest-growing private companies.Connect with Jeremy:Email: [email protected]: Jeremy ParkerABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 74: Jon Tucker of HelpFlow on AI for business efficiency and Evaluating AI Performance
AI for Business Efficiency is reshaping how companies operate, and in this episode, Jon Tucker, founder of HelpFlow, shares how AI is transforming customer service, workflow automation, and decision-making. We dive into Evaluating AI Performance, optimizing operations, and leveraging AI to scale businesses while staying competitive.Jon reveals how AI reduces workforce needs, enhances productivity, and even impacts venture capital and startup growth. We also explore Boardy AI, AI-assisted coding, and the rise of Chief AI Officers.-------------------------------Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode74&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode74&utm_id=FundraisingDemystifiedPodcastIf you’re looking to maximize AI output and boost efficiency, this episode is packed with insights. Don’t forget to like, subscribe, and stay tuned for more!Here’s what you’ll find in this episode:00:00 - Introduction to Jon Tucker & HelpFlow01:30 - AI’s impact on customer service & workforce reduction04:00 - The importance of Evaluating AI Performance07:15 - How AI enables business efficiency and scalability12:45 - AI’s role in startup growth and venture capital trends18:30 - AI workflow automation & AI-assisted coding24:00 - Future of AI: Chief AI Officers, automation, and scaling28:30 - Boardy AI and next-gen AI-powered networkingABOUT JON TUCKERJon Tucker is the CEO atHelpFlow.com. Over the past decade, he’s managed remote teams and faced the frustrations of micromanaging every detail—an experience that drove him to embrace AI for smarter delegation. Through HelpFlow’s “smart staff” model and their proprietary GuideLayer AI, Jon transforms traditional virtual assistants into high-value, autonomous team members. His goal? Free founders from busywork so they can scale faster and focus on what truly matters. Ready to see how AI can change the way you work? Try the AI at HelpFlow.com/demo-ai-videoConnect with Jon Tucker: Website:HelpFlow.comLinkedIn: https://www.linkedin.com/in/jontuckerusa/ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]:https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 73: Fundraising Quadrants Explained: Where Does Your Startup Fit?
Not all startups should chase VC money. Some should bootstrap, others should take on debt, and a few are primed for private equity. So how do you know which path is right for you?In this episode,Jason Kirby breaks down theFundraising Quadrants—a framework that helps founders identify where they stand in their startup journey and what type of capital makes the most sense for them. Whether you’re running an AI startup, a SaaS company, or a growing e-commerce brand, this episode will help you avoid common fundraising mistakes and focus on strategies that align with your vision.------------------------------------------Raising capital? Get a list of vetted VCs for FREE here:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode73&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode73&utm_id=FundraisingDemystifiedPodcastHere’s what you’ll find in this episode:00:00 Introduction to Fundraising Quadrants00:32 Speaker's Background and Expertise01:15 TheNorth Star framework: What do you really want to achieve?03:42 What are the Fundraising Quadrants? Find out where you stand05:29 Breaking down the quadrants: Early Growth, Established Growth, Strong but Slow, Struggling06:47 Venture Capital: When and how to attract investors (and when to avoid them!)09:09 Debt Financing: Leveraging assets, revenue, and strategic borrowing12:20 Private Equity: What PE firms look for & how to position your startup15:16 Planning Your Exit: M&A, acquisitions, and strategic partnerships18:24 The Big Question:Should you use investor money or bootstrap?18:44 HowThunder VC helps founders navigate fundraising-------------------------------------ABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 72: Bootstrapping, Exiting, and Alternative Fundraising with Laurits Just
Would you rather grind for years bootstrapping, take VC money with strings attached, or sell and move on? That’s the exact crossroads Laurits Just faced as the co-founder of BitsForDigits.In this episode, Laurits breaks down how he built and sold his startup, a marketplace for partial business acquisitions, and why he ultimately chose to exit instead of raising venture capital. He shares the highs and lows of bootstrapping, the challenge of getting a two-sided marketplace off the ground, and the inside story of negotiating his sale to Flippa.Now leading Flippa Invest, Laurits is on a mission to help founders secure funding—without the pressure of chasing unicorn status. If you’re a founder weighing your options, this episode will open your eyes to paths beyond traditional VC.---------------------------------------Raising capital?Get a list of vetted VCs for FREE here:https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode72&utm_id=FundraisingDemystifiedPodcastGet the latest fundraising insights, news, and tips:https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode72&utm_id=FundraisingDemystifiedPodcastHere’s what you’ll find in this episode: 00:00: Introduction 01:40: The story behind the startup and bootstrapping 02:49: Overcoming the challenges of a two-sided marketplace 05:44: Growing profitably and attracting acquisition offers 06:03: Why Laurits and his co-founder decided to sell to Flippa 09:53: Bootstrapping vs. raising capital: The three-door dilemma 12:34: Running a competitive sale process for maximum exit value 18:10: Life after the acquisition: Transitioning to Flippa Invest 21:04: How Flippa Invest offers an alternative to VC funding 24:19: The types of businesses that fit the Flippa Invest model 28:12: Understanding valuation and fundraising expectations 36:45: How founders can explore funding through Flippa InvestABOUT LAURITS JUSTLaurits Just is the co-founder and co-CEO of BitsForDigits, a marketplace for partial and full business acquisitions. With a background in finance, he worked at BlackRock and Rocket Internet in London before launching his startup. Holding three degrees—including a Master of Science from the London School of Economics—Laurits specialized in digital innovation, AI applications, and distributed ledger platforms.After leaving BlackRock, he co-founded BitsForDigits with a mission to provide liquidity solutions for self-funded business owners. Inspired by a blog post on Jeff Bezos' investment in Basecamp, he and his co-founder built a platform that made secondary transactions more accessible. After scaling the business to profitability, they ultimately exited to Flippa, where Laurits now leads Flippa Invest, helping founders secure funding beyond traditional VC.Connect with Laurits: Website: Flippa Invest LinkedIn: Laurits JustABOUT JASONJason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development.You can reach out to Jason through:Email: [email protected]: https://www.linkedin.com/in/jasonrkirby/ABOUT FUNDRAISING DEMYSTIFIEDOur goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape.Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 71: How Rebel Energy Scaled £1.5M to £100M with Penelope Hope
Penelope Hope, founder of Rebel Energy, shares her journey of building a renewable energy company from scratch with just £1.5 million raised, scaling it to £100 million in revenue in record time. Rebel Energy's mission to alleviate fuel poverty while delivering renewable energy has set it apart as an innovative force in the UK energy sector. In this episode, Penelope details her early challenges, fundraising strategies, and insights into scaling a utilities business sustainably and profitably. She also discusses her decision to step back from Rebel Energy and her vision for entrepreneurship in the UK. Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode71&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=YouTube&utm_medium=Video&utm_campaign=Episode71&utm_id=FundraisingDemystifiedPodcast Here’s what you’ll find in this episode: 00:00 Introduction and Guest Welcome 00:25 Early Days and Initial Fundraising 01:39 Fundraising Strategies and Challenges 05:57 Crowdfunding Success and Market Entry 09:27 Growth Strategy and Operational Efficiency 14:06 Profitability and Future Plans 15:49 Stepping Down and Reflecting on the Journey 19:09 Advice for Founders and Fundraising Tips 22:06 UK Startup Ecosystem and Opportunities 32:55 Networking and Access to Investors 34:49 Conclusion and Final Thoughts ABOUT PENELOPE HOPE Penelope Hope co-founded Rebel Energy, a UK-based renewable energy supplier with a mission to alleviate fuel poverty. Under her leadership, the company grew from its initial $1.5 million raise to achieving over $100 million in revenue while maintaining profitability from day one. A strong advocate of operational efficiency, Penelope leveraged automation to stay competitive in the fragmented UK energy market. Penelope has a background as an equity analyst and a deep commitment to social and environmental missions. After stepping back from Rebel Energy, she continues to inspire founders by sharing her experiences and advocating for founder-led innovation. Connect with PENELOPE: LinkedIn: https://www.linkedin.com/in/penelope-hope/ ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 70: From Founder to Philanthropist: $1.3B Deployed by David Goldberg
After achieving financial success as a founder, David Goldberg shifted his focus to making a global impact. As the founder of Founders Pledge, David has pioneered a transformative approach to philanthropy, enabling entrepreneurs to commit a portion of their exit proceeds to charity. Over the past 10 years, Founders Pledge has deployed $1.3 billion toward impactful causes, making it one of the most innovative nonprofit organizations for founders. David discusses the philosophy behind Founders Pledge, the challenges of creating a global philanthropic network, and the strategies for ensuring every dollar donated achieves measurable results. Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101 Here’s what you’ll find in this episode: 00:02 Introduction 00:16 David Goldberg’s journey from founder to philanthropist 03:50 The origins of Founders Pledge and its mission 08:00 How pledging future earnings fosters impact-driven giving 12:15 Deploying $1.3B: How Founders Pledge maximizes impact 20:30 The importance of trust and transparency in philanthropy 33:08 Scaling Founders Pledge: Challenges and aspirations ABOUT DAVID GOLDBERG David Goldberg is the co-founder and CEO of Founders Pledge, a global nonprofit that empowers entrepreneurs to commit a portion of their exits to high-impact philanthropy. Under his leadership, the organization has grown to over 2,000 members across 40 countries, with nearly $11 billion pledged and $1.3 billion deployed to transformative causes. Driven by a mission to simplify and amplify meaningful change, David transitioned from a diverse commercial background to the nonprofit sector, blending his expertise in finance, startups, and academia. Before Founders Pledge, David gained experience as a mortgage and investment banker and launched the secondary marketing department at Mortgage Capital Associates. A serial entrepreneur, he founded a boutique real estate firm in Germany and managed Urban Motion. He is a graduate of UCLA and the University of Cambridge, where he deepened his understanding of systems driving impactful change. Inspired by the desire to make philanthropy accessible, David has built a community where founders can harness their success to improve the world. Connect with DAVID: Website: www.founderspledge.com ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 69: Scaling and Selling to Eight-Figure Exits with Carrie Kerpen
From founding one of the earliest social media agencies to crafting an intentional path to a major eight-figure exit, Carrie Kerpen has redefined what it means to be a female entrepreneur in the digital age. In this episode, Carrie shares the transformative strategies she used to scale Likeable Media into a profitable and sellable business. Carrie reveals her RED (Recurring, Expected, Diversified) revenue framework, discusses the importance of building businesses beyond the founder and provides insights into the challenges women founders face during the acquisition process. _________________________ Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101 Here’s what you’ll find in this episode: 00:00 Introduction 00:15 Building Likeable Media and scaling one of the first social media agencies 04:15 The RED framework for making a business a sellable asset 10:10 The exit gap and its impact on women entrepreneurs 15:59 Why recurring revenue is key to a strong exit 22:05 Trends in M&A and the importance of AI in future acquisitions 33:20 Insights into The Whisper Way, Carrie's upcoming book ABOUT CARRIE KERPEN Carrie Kerpen is a trailblazing entrepreneur, author, and advocate for female founders. She built Likeable Media, a pioneer in the social media agency space, which scaled rapidly and achieved a major exit in 2021. Carrie now leads The Whisper Group, focusing on exit readiness for women-owned businesses, and is set to release her book The Whisper Way in May 2025. Through her work, Carrie has empowered countless founders to dream big, execute strategic plans, and confidently navigate the exit process. Connect with Carrie: Website: CarrieKerpen.com The Whisper Group: WeAreTheWhisperGroup.com LinkedIn: Carrie Kerpen ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 68: From Bootstrapping to an Eight-Figure Exit with Conor Tomkies
From dog genetics to bootstrapping to an eight-figure exit , Conor Tomkies has done it all. As the founder of Support Ninja, Conor scaled a bootstrapped business into a middle eight-figure success story, managing thousands of employees worldwide. After selling to private equity, Conor is now building Operator Equity and Entrepreneur Cooperative, empowering founders to scale and exit with purpose. Conor Tomkies shares how he leveraged strategic legal and operational efficiencies to save millions during acquisitions. He highlights his founder-first approach with Operator Equity, focused on scaling SaaS businesses using EOS, and discusses the startup shift from venture-backed moonshots to sustainable, profitable growth. ----------------------------------------------------- Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101 Here's what you'll find in this episode: 00:00 Introduction 00:37 Dog genetics and the birth of Support Ninja 02:54 Bootstrapping vs. raising venture capital 05:30 Lessons from selling to private equity 10:14 Why EOS is a game-changer for scaling companies 18:34 Operator Equity’s focus on SaaS and ecosystem synergy 27:00 Common founder mistakes and the value of recurring revenue 30:45 The rise of moonshots and the future of venture capital ABOUT CONOR TOMKIES Conor Tomkies is a serial entrepreneur, investor, and post-exit founder with a passion for creating scalable businesses and empowering other entrepreneurs. He founded Support Ninja, a bootstrapped outsourcing company that scaled into a middle eight-figure success story and sold it to private equity. Now leading Operator Equity, Conor focuses on acquiring and scaling SaaS businesses using the Entrepreneurial Operating System (EOS), helping founders navigate successful exits with a streamlined 45-day process that prioritizes simplicity and a human touch. Conor is also the co-founder of Entrepreneur Cooperative (ECo) and host of the Made It Podcast. Through ECo, he has built a community where seasoned founders share experiences, collaborate, and gain insider strategies for navigating business sales and life beyond the exit. It’s the network every entrepreneur wishes they had when starting out, focused on meaningful growth, impactful exits, and supporting the next generation of founders. Connect with Conor: Website: operatorequity.com Entrepreneur Cooperative: entrepreneurcooperative.com X (formerly Twitter): @conortomkies_ ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 67: From Bootstrapping to $175M Exits with David Hauser
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101 ----------------------------------------------------- What does it take to build, scale, and sell a business—and then do it all over again? David Hauser, the mastermind behind Grasshopper and Vanilla, has done just that. Starting with his very first pitch to his father for a Dell computer, David went on to raise nine figures for Return Path, bootstrap Grasshopper into a $175M success, and disrupt estate planning with Vanilla. But it hasn’t been all smooth sailing. In this episode, David opens up about the emotional aftermath of exiting a company, the identity struggles that follow, and how he found purpose by taking the leap into a new chapter. Now leading Durable Capital, David is focused on acquiring and scaling profitable companies while mentoring the next generation of founders. Here's what you'll find in this episode: 00:00Trailer/ Introduction 01:23 Early days: From a Dell computer to Return Path 06:02 Bootstrapping Grasshopper to a $175M exit 18:26 Vanilla and the decision to raise $42M in venture capital 25:34 Navigating post-exit identity shifts and finding fulfillment 39:00 Durable Capital: Buying and scaling profitable businesses 41:28 Mentoring the next generation of founders ABOUT DAVID HAUSER David Hauser is a serial entrepreneur, investor, and speaker known for founding and scaling successful companies like Grasshopper (bootstrapped to $30M+ ARR, acquired by Citrix), Chargify (profitable, Mark Cuban-backed, acquired by Battery Ventures), and Vanilla (raised $42M from Venrock and Insight Partners). A founding member of National Entrepreneurs’ Day, he has also invested in over 50 startups, including Intercom and Unbounce. David’s insights have been featured in major outlets like CNN, Fox, and The Wall Street Journal, and he has spoken at renowned events such as SaaSFest and Big Omaha. Now leading Durable Capital from Las Vegas, he focuses on acquiring profitable businesses and mentoring the next generation of founders. Connect with David on: Website: www.davidhauser.com ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 66: How Patrick Butler Built 3 Wildly Different Businesses
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101 ----------------------------------------------------- What do a career coaching platform, a French-American football team, and a fraud prevention startup have in common? Meet Patrick Butler, the mind behind all three. Talk about a guy who doesn't do boring. One minute he's running a career coaching platform, the next he's starting a football team in Paris, and now he's crushing it with a fraud prevention startup called BizDefender. In this episode, Patrick shares the details of how he's jumped between totally different worlds. We're talking crazy fundraising tricks, buying up companies most people would run from, and basically rewriting the rulebook on how startups actually work. Seriously, who starts a pro football team as a side hustle? This guy. And he makes it sound like it's no big deal. It's the kind of story that makes you wonder: Are some people just wired differently? Patrick seems to turn wild ideas into businesses while most of us are still planning our next move. Want to hear about breaking every conventional rule in entrepreneurship? This is your episode. Here's what you'll find in this episode: 00:00 The Unlikely Pitch: Starting an American Football Team in France 00:48 Meet Patrick Butler: From Startup Success to Private Equity Exit 01:24 The Journey of Talent Inc.: From Struggles to Success 02:11 The Power of a Great Co-Founder: Meeting Jeff 03:29 Building Talent Inc.: The Resume Revolution 05:51 Scaling Up: Acquisitions and Growth Strategies 09:46 Navigating Fundraising: Debt, Equity, and Private Investors 19:59 Post-Exit Reflections: Life After Talent Inc. 21:30 A New Venture: Launching an American Football Team in Paris 25:51 Meeting a Nike Executive and Defining Our Vision 26:40 The Importance of a Brand Book 28:09 Convincing the French with American Football Culture 30:30 Economics of Starting a Football Team in France 31:51 Revenue Drivers and Merchandise 36:07 Launching BizDefender: A New Venture 41:13 Preventing Small Business Fraud with BizDefender 43:40 The Journey and Future of BizDefender 47:59 Final Thoughts and Contact Information ABOUT PATRICK BUTLER Patrick Butler is a serial entrepreneur, co-founder, and CEO of BizDefender, a first-of-its-kind fraud prevention tool for SMBs. His entrepreneurial achievements include leading Talent Inc. to a successful exit and co-founding a professional American football team in France. Patrick is passionate about creating impactful businesses while fostering innovation across industries. Connect with Patrick on: Website: www.pbutler.com Biz Defender: www.bizdefender.com ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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EP 65: Navigating Debt Financing for Startups with Kyle Rector of Boundless
Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101 ------------------------------------------------ Think debt is a trap? Think again. Learn how the right kind of debt can fuel your growth without sacrificing control of your startup. In this insightful episode, Jason Kirby welcomes Kyle Rector, co-founder and president of Boundless, to shed light on an often-overlooked aspect of startup funding: debt financing. If equity raises are the headlines, debt is the subplot that drives growth for countless businesses—but only if founders understand how to wield it wisely. Kyle shares hard-earned wisdom from a decade of navigating the debt financing space, offering practical advice for founders at all stages. Kyle walks us through the spectrum of non-dilutive funding options, from the basics of debt vs. equity to the complexities of venture debt, revenue-based financing, and more. Whether you’re looking to extend runway, fuel expansion, or build sustainable operations, this episode equips you with the knowledge to make informed capital decisions. Here's what you'll find in this episode: 00:00 Introduction to Debt Financing 00:08 Meet Kyle Rector: Debt Financing Expert 00:55 Understanding Debt vs Equity 03:41 Types of Debt for Businesses 08:27 Term Loans Explained 09:59 Lines of Credit: Flexible Financing 11:42 Secured vs Unsecured Financing 16:48 Venture Debt: A Strategic Option 22:23 Revenue-Based Financing: Pros and Cons 29:49 Exploring Different Types of Debt Financing 30:07 Valuing Contracts and Lines of Credit 32:56 Preparing to Secure Debt: Key Considerations 37:14 Understanding Debt Service Coverage Ratio (DSCR) 40:35 Benchmarking Debt Options for Different Business Profiles 51:47 Building Relationships and Trust with Lenders 54:05 Conclusion and Final Thoughts ABOUT KYLE RECTOR Kyle Rector is the co-founder and president of Boundless, a capital marketplace connecting businesses with lenders through tailored solutions. With over 10 years of experience in debt financing, Kyle has facilitated billions in capital requests, spanning industries and geographies. His mission with Boundless is to simplify the capital application process, enabling founders to focus on scaling their businesses. Connect with Kyle on: Webiste: www.getboundless.ai ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: [email protected] LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.
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ABOUT THIS SHOW
In this podcast, we uncover the untold stories of founders who have weathered the highs and lows of raising capital. We go beyond the headlines and Techcrunch funding news articles to explore the uncharted territories of the fundraising landscape.In each episode, we'll sit down with founders from various industries who have raised venture capital to bring their visions to life. They'll open up about their personal journeys, fundraising tactics & more.If you're a founder, this podcast offers a ton of value & insights you can apply to your fundraising journey. Don't forget to hit subscribe!
HOSTED BY
Jason Kirby
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