Not Another CEO Podcast

Building software is hard but building a category-defining enterprise company for 20 years is a different game entirely.In this episode of Not Another CEO Podcast, David sits down with Marcus Ryu, Co-Founder and former CEO of Guidewire, the software platform that transformed the insurance industry and grew into a public company generating over $1.5 billion in revenue.Marcus shares the hard-earned lessons from building Guidewire from zero: developing strategic clarity, surviving years-long sales cycles, learning how to sell as a founder, navigating investor pressure, handling lawsuits from incumbents, and sustaining the emotional intensity of being a founder CEO for nearly 20 years.This conversation is a masterclass on company building, resilience, leadership, and the psychological realities behind building enduring businesses.Takeaways:1. Strategic coherence matters more than speed:Marcus explains how Guidewire constantly revisited its assumptions whenever new information appeared maintaining ruthless intellectual honesty around strategy instead of blindly executing.2. Every founder must learn how to sell:Despite not coming from sales, Marcus says learning sales became one of the most valuable skills of his entire career. Great CEOs are constantly persuading customers, employees, investors, and markets.3. Enduring companies require patience:Guidewire’s early sales cycles lasted 1–2 years, and implementations could take another 1–2 years. Marcus shares why building meaningful companies often demands long-term thinking and delayed gratification.4. Capital efficiency creates resilience:Guidewire raised only $29 million throughout its journey to IPO. Marcus discusses how treating every dollar like it could be the last shaped the company’s discipline and culture.5. Intensity without serenity can become dangerous:Looking back, Marcus says he spent years carrying catastrophic pressure and anxiety as a founder. His biggest reflection is learning that great CEOs can be both intensely driven and internally calm at the same time.Quote of the Show:“If you can be intense and serene at the same time, then you really have a superpower.” - Marcus Ryu, Founder & Former CEO, GuidewireChapters:00:00 - Trailer02:10 - The importance of strategic coherence in company building08:45 - Why startups need an enemy and a clear sense of differentiation15:20 - Discovering the broken insurance software market27:20 - Learning sales as a founder CEO31:00 - Getting the first customers & surviving long enterprise sales cycles36:20 - Building Guidewire with extreme capital efficiency43:10 - The pressure modern founders feel to grow at impossible speeds49:40 - Surviving lawsuits and competitive attacks from incumbents58:00 - Transitioning from founder CEO to investor at Battery Ventures01:06:30 - Marcus’s biggest personal reflection after two decades as CEO

He walked back to his apartment and found 50 sticky notes on the door. "Sorry we missed your package." That problem became a $1.5 billion company competing directly with UPS and FedEx.Itamar Zur, Co-Founder and CEO of Veho, shares the full story of building one of the most disruptive logistics companies in America from a business school dorm room to 65 markets, nearly 1,000 employees, tens of thousands of drivers, and over $300 million raised from General Catalyst, SoftBank, and Tiger Global.In this conversation, Itamar opens up about what it really took: obsessing over the Day One customer experience in a way most founders never do, rebuilding the company's values from scratch after 2022 nearly broke everything, and creating a deliberate program to identify and invest in top performers before someone else does.If you're building a company and want to understand what championship-level execution actually looks like from the inside, this episode is worth your time.Takeaways:Obsess Over the Day One Experience: Itamar would send detailed end-of-day reports not just to his buyer but to the CEO, CMO, and CFO of every new customer anyone whose email he could find. By the next call, those buyers weren't asking how things were going. They were asking what other markets Veho could go to. First impressions compound.Values Must Evolve as the Company Evolves: Veho launched with human-first, idealistic values. When the market turned in 2022 and performance management became non-negotiable, those values created internal friction. Itamar rebuilt them from scratch around a championship team mentality. The wrong people left. The right people finally had language for what they had been doing all along.Your 10X People Know They Are 10X Invest in Them Before Someone Else Does: High performers don't complain, don't ask silly questions at all-hands, and quietly deliver results every single day.The Co-Founder Decision Is the Most Important One You Will Make: Two original co-founders left over a fundamental strategic disagreement. Itamar refused to compromise on the vision, finding Fred one person he had met once at a conference changed the entire trajectory of the company.This Is a Marathon Protect the Runner: When the market shifted, the mental and physical toll hit all at once. He now meditates, exercises, sleeps 7–8 hours, and treats it the same way a professional athlete treats training. Everything else depends on it.Quote of the Show: "The way you do anything is the way you do everything." - Itamar Zur, Co-Founder & CEO, VehoLinks: LinkedIn: https://www.linkedin.com/in/itamarzur/ Veho Website: https://www.shipveho.com/Chapters: 00:00 – Intro: From a sticky note to a $1.5B logistics company 01:19 – The one thing: obsessing over the Day One customer experience 05:30 – Sending reports to the CEO, CMO, and CFO why it worked 09:45 – The moment of truth: lessons from Procter & Gamble 14:20 – Veho's original values and why they had to change 18:05 – Championship team mentality: rebuilding culture mid-flight 22:40 – How top performers act and why they never speak up 27:15 – The Force Multipliers program: investing in your all-stars 31:50 – Finding Fred: the co-founder story 38:30 – 2022: the year that almost broke everything 46:00 – The coach conversation that changed how he leads 52:00 – Taking care of your body and mind as a founder 58:10 – Advice to his younger self: give yourself time to learn

Description:Most companies don’t fail because of bad strategy they fail because of bad hires.In this solo episode, David Politis breaks down a battle-tested 10-step interview framework built from 20+ years of experience, hundreds of CEO conversations, and real-world hiring mistakes. From uncovering the real motivations behind a candidate’s story to spotting red flags most interviewers miss, this episode is a masterclass in hiring with intention.David challenges the common belief that “people are your greatest asset” and reframes it: the right people are everything. Because the cost of getting it wrong isn’t just time it can be millions in lost value, broken teams, and missed opportunities.Takeaways :1. “The right people” > just “people”: Hiring isn’t a volume game. One wrong hire especially at leadership level can cost millions in enterprise value and derail entire teams.2. Most companies are “winging” interviews: Very few leaders are formally trained in hiring. Lack of structure leads to poor candidate experience, wasted leadership time, and bad hires.3. Depth beats polish in interviews: Great candidates can go into the details. If someone can’t get into the weeds metrics, decisions, outcomes that’s a major red flag.4. The power of “why” questions: Asking layered “why” questions helps you move past rehearsed answers and uncover true motivations, decision-making, and character.5. Hiring is about alignment, not just capability: Understanding what energizes a candidate and where they want to go is critical. Even great talent fails when there’s misalignment with the role.Quote of the Show : "The reality is that we're winging it. And the cost of winging it is very, very high. The cost of hiring the wrong person there could be literally millions, if not tens of millions of dollars of enterprise value lost." - David Politis, Host of Not Another CEOChapters00:00 – Why hiring is the highest-leverage decision you make06:14 – “The right people” vs. just people08:30 – The hidden cost of bad hiring decisions11:00 – Why most companies are winging interviews13:30 – The importance of preparation and alignment16:00 – The power of taking decision-grade notes18:30 – Step 1–3: Setting the tone, story, and “why” questions21:00 – Going deep: testing real experience and competence25:00 – Finding what energizes candidates29:00 – Anti-selling the role + spotting red flags in questions

What happens when the company you built… is no longer yours?Rob LoCascio, Founder of LivePerson, shares the full, unfiltered reality of building, scaling, losing, and rebuilding as a founder. From starting with almost nothing to taking his company public, scaling it from $900M to $4B in just 12 months during COVID and then facing the brutal reality of losing control of what he built.In this conversation, Rob opens up about the hardest chapter of his career: fighting to hold onto his company, the emotional toll of watching it decline after his departure, and the moment he realized that everything he created was at risk.He also dives into what separates founders who come back from those who don’t, why creativity is the one asset no one can ever take from you, and how to rebuild your identity when the company you built is no longer yours.This isn’t just a story about success or failure it’s about ownership, resilience, and what it really means to be a builder.If you’re building something or afraid of losing it this episode will hit hard.Takeaways:They Can Take the Company, Not the Builder: Rob’s biggest realization came after losing control everything external can be stripped away, but your ability to create, build, and execute is untouchable. That’s the real edge founders have.Scaling Fast Comes With Hidden Risk: Going from $900M to $4B in 12 months sounds like a dream but hypergrowth brings pressure, expectations, and fragility that most people don’t see until it’s too late.Founder Identity Is the Real Battle: Losing a company isn’t just financial it’s deeply personal. Rob breaks down what it feels like to lose something you poured your life into, and how to rebuild from that.Fighting for What You Built Isn’t Optional: When things started slipping, Rob didn’t walk away he fought. And he explains why that fight was the hardest thing he’s ever faced as a leader.Your Gift Is the Only Constant: Markets change, companies rise and fall but your creativity, vision, and ability to build are the only things that stay with you for life.Quote of the Show:"They can take your company. They can take your money. But they can’t take your creativity, the ability to build again." - Rob LoCascioLinks:- LinkedIn: https://www.linkedin.com/in/rlocascio/- LivePerson: https://www.liveperson.com- KID Company: https://www.kidco.ai/- Uare.ai: https://www.uare.ai/Chapters:00:00 – Intro01:19 – From nothing: $5K, a couch, and starting over02:10 – Building LivePerson and going public05:30 – The COVID surge: $900M to $4B in 12 months09:45 – When things started to break14:20 – Losing control of the company he built18:05 – The hardest fight of his career22:40 – Watching the company decline after leaving27:15 – The emotional toll of losing everything31:50 – Identity beyond the company36:10 – Why founders can always build again41:25 – Creativity as the ultimate unfair advantage46:00 – What Rob is building next50:30 – The real meaning of success and failure

What really happens when you bet it all on your company & end up with nothing?Ra'anan Cohen, Author & Founder of MobileMax and Bringg, pulls back the curtain on what most founders never talk about going from IPO to broke, rebuilding from zero, and finally selling at a $1 billion unicorn valuation with the scars to prove it.In this conversation, he shares why he turned down $10M in stock at a public company and lived to regret it, how he secretly rebuilt himself while the whole industry thought he was already rich, and what changed at Bringg that made him finally know when to pull the plug.If you're building something and trying to figure out when to hold and when to fold, this episode is for you.Takeaways:Build the Team First, Everything Else Second: The single biggest factor in both MobileMax and Bringg was team. Ra'anan implemented a strict no-asshole policy at Bringg not just hiring for talent, but for personality, attitude, and the ability to endure a long, grinding journey.Know When to Take the Money: Turning down $10M in stock from institutional investors during MobileMax's IPO when the company was worth $100M cost Ra'anan everything. He walked away from Bringg at $1B because the 8-year scar from MobileMax kicked in.Fake It Till You Make It Has a Dark Side: After MobileMax collapsed, Ra'anan went to startup meetups while secretly broke and struggling watching everyone else perform success. He later learned everyone was doing the same thing. His book, Confessions of a Unicorn Founder, exists specifically to break this culture open.Secondary Is a Founder's Right, Not a Weakness: Old-school investors want founders "hungry." Ra'anan disagrees. Taking secondary closes the open loops in your brain the daily stress about going to zero and actually frees founders to dream bigger and swing harder, not less.Quote of the Show:"People like to say startup is like a roller coaster. I think this is very misleading. In the startup life as a founder, 90, 95% of the time I'm in crisis mode. It's not a roller coaster it's a marathon." - Ra'anan Cohen, Author & Founder of MobileMax & BringgLinks:Book: Confessions of a Unicorn Founder - available on AmazonLinkedIn: https://www.linkedin.com/in/raananc/Website: www.raanancohen.comChapters:00:00 – Intro: From IPO to zero to unicorn Ra'anan's full arc01:22 – The one thing that had the biggest impact: team building06:00 – The no-asshole policy and how to hire for attitude08:50 – Framing hard weeks as progress the "great week" mantra13:48 – MobileMax: the IPO, the $10M phone call, and saying no16:32 – Why Ra'anan didn't sell a single stock and what it cost him18:54 – When the iPhone reshaped mobile and MobileMax spiraled25:05 – Broke and "the guy who made it" faking it at startup meetups32:14 – The personal cost: family, presence, and the founder's obsession34:13 – How a late pizza sparked the idea for Bringg36:39 – Bringg's rise: customers, unicorn valuation, and pulling the plug38:35 – Secondary, investor philosophies, and closing the open loop45:26 – Fairness for founders: why secondary isn't just smart, it's right50:15 – Writing Confessions of a Unicorn Founder and what comes next52:02 – The one piece of advice Ra'anan would give his younger self

What if the reason your company isn’t growing… is because you’re spending too much time inside the company instead of with your customers?Erica Jain, Co-Founder & CEO of Healthie, breaks down how a relentless customer-first mindset shaped every part of the business from product decisions to hiring to long-term strategy.In this conversation, she shares how they got their first customers with no sales experience, why internal inefficiency is a bigger risk than doing too much, and what it really takes to maintain speed as a company scales. She also dives into rebuilding the product after early success, hiring for values, and staying in control while growing a profitable company.If you want to build faster, stay close to your customers, and avoid the trap of internal complexity slowing you down this episode is for you.Takeaways:Obsess Over Customers as Your True North Star: The single most important thing is to instill a true customer-first mindset across the entire company. Customers literally “keep our lights on” every decision, roadmap, and internal process should revolve around delivering an incredible experience for them.Simplify Your Values Ruthlessly: Erica and her team reduced their values from eight which nobody could remember to just the Three R’s: Respect, Resilience, and Reliability. Hire for values far more than skills, especially as technology changes rapidly.Profitability Equals Control: They chose to remain profitable for most of the company’s life to always stay in control of their destiny. Build a generational business and raise capital only when it serves clear long-term goals, never out of desperation.Mediocrity Is the Real Killer: Companies don’t usually die from doing too many things they die from descending into mediocrity caused by slow internal processes, too many meetings, and inefficient decision-making. Speed and execution velocity matter enormously.Hiring, Team Building, and Scaling Challenges: Hiring for values, the difficulty of identifying customer-first people in interviews, retaining talent (many team members 5–7+ years), going through a major codebase rewrite, and the constant battle against internal inefficiency as the company grows.Quote of the Show:The one thing I would do is instill… a true customer first mindset. There is something incredibly, incredibly powerful about waking up every single minute of every single day and wholeheartedly focusing on making sure our customers are taken care of.”- Erica Jane, CEO & Co-Founder of Healthie.Links:LinkedIn: https://www.linkedin.com/in/ericajain/Website: https://www.gethealthie.com/Chapters00:00 – Intro: Healthie’s growth, impact & profitability00:56 – The power of a true customer-first mindset03:11 – How to build with customers from day one06:00 – Hiring for values: the “3 R’s” framework08:53 – Evolving culture as the company scales12:54 – Operating systems & using OKRs effectively16:50 – Why inefficiency kills companies (not ambition)19:35 – Profitability, fundraising & staying in control24:08 – Starting Healthie & getting first customers30:30 – Biggest challenges: tech debt & rebuilding the product

How can one simple strategy drive your company’s success? In this solo episode of Not Another CEO Podcast, host David Politis dives deep into the significance of alignment and prioritization within a company. Reflecting on a personal article shared via Substack, David emphasizes the importance of refocusing and reprioritizing company goals as new challenges and opportunities arise.Takeaways: Concentration of Efforts: Narrowing down the focus to one primary goal can unify and effectively drive a company's momentum. By concentrating efforts, every team member can contribute to company growth.Effective Communication: Regular and focused communication is key to keeping everyone aligned with the company's goals. David suggests updating the team weekly to maintain a cadence that ensures urgency and focus.Culture of Outcome-Based Work: Create a work culture that rewards achievements based on outcomes rather than just effort. It’s crucial for employees to understand their work's impact on the company's success.Celebration of Successes: Recognizing and celebrating achievements fosters a positive work environment and encourages further productivity. Celebrations can be as simple as an email recognition or a shoutout during all-hands meetings.Strategic Compensation: Implementing flexible compensation structures isn't limited to sales teams. Properly aligning compensation with company goals can motivate teams across the board to go above and beyond.Removing Distractions: Encourage leadership to stay concentrated on key goals by avoiding changes in priorities throughout the quarter. Written notes can capture evolving ideas, which can then be revisited during the next planning phase.Leadership Involvement: Leaders should actively remove barriers for their teams rather than changing priorities. This approach helps maintain focus and supports execution on high-priority initiatives.Quote of the Show:“The less you communicate about the other things, and the more you just make all the communication about that thing, people are gonna understand this is what we're focusing on." - David PolitisWays to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #MarchPulseChapters:00:00 Intro00:48 Q2 Reprioritization Problem02:36 Five Cs Framework02:47 Concentrate Efforts04:32 Communicate With Cadence05:55 Outcome Driven Culture06:44 Celebrate The Wins08:13 Compensation Drives Behavior11:26 Stay Focused For A Quarter12:49 Outro

What does it take to transform a struggling startup into a booming enterprise? In this episode of Not Another CEO Podcast, host David Politis sits down with Didi Gurfinkel, Co-Founder and CEO of Datarails. Together, they delve into Didi's decade-long journey of building a successful financial platform from scratch, discussing both the struggles and triumphs of his entrepreneurial path.From his early days at Cisco to co-founding Datarails, Didi shares invaluable lessons on startup pivoting, embracing new technologies, and harnessing AI to revolutionize financial operations.Takeaways: The Power of the Right Team: Didi highlights the importance of having the right co-founders. He credits the success of Datarails largely to the strong foundational team that shared common goals and complementary skills.Embracing the Brutal Truth: Didi emphasizes the need for leaders to be honest about their failures and to learn from them while maintaining a visionary outlook for the future.Importance of Having a Name: Drawing from past experiences, Didi advises startups to choose a product that has a recognisable name and existing budget line.Finding Your Ideal Market Fit: Datarails achieved success by narrowing their focus to finance professionals who love Excel, aligning product benefits with users’ existing skills and preferences.Strategic Use of AI: Datarails seeks to prepare organizations for AI integration, ensuring readiness for technological advancements.Balancing Work and Family: Didi points out that while entrepreneurship is all-consuming, showcasing the possibility of building something significant can offer invaluable lessons for family.Quote of the Show:“If someone ask me, I'm not sure if I have the product market fit, I'm saying, no, you don't have it. If you had it, you know." - Didi GurfinkelLinks:LinkedIn:https://www.linkedin.com/in/didigurfinkel/ Website: https://www.datarails.com/   Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:21 Co-Founders Matter Most02:28 Finding the Right Partners05:47 Evolving Founder Roles07:28 Five Tough Early Years09:28 Building Tech Without Sales13:08 Staying Motivated to Pivot18:05 The Breakthrough Pivot20:52 Why FP&A and Mid-Market24:40 Scrappy Early Go-To-Market26:38 LinkedIn Phone Number Hack28:17 Knowing Product Market Fit30:43 Removing Buying Friction32:47 Zero to One Million ARR35:26 AI and Finance OS Vision41:38 Three Year Company Outlook43:06 Founder Origin Story46:25 Israel Startup Mindset47:50 No Work Life Balance51:02 Outro

What sets apart the founders who persevere through immense challenges and come out stronger on the other side? In this episode, David sits down with Shaun Abrahamson, Co-Founder & Managing Partner at Third Sphere. Shaun shares his unique insights into the high-stakes world of venture investing, particularly in climate tech and hardware, reflecting on the kinds of founders he backs and the unforeseen hurdles they've had to overcome.Shaun delves into his philosophy on investing in early-stage companies, emphasizing the importance of resilience and adaptability in founders. He also discusses the intricacies of climate tech investment and the lessons he's learned from over two decades in the field.  Takeaways:The Importance of "Burned Bridges": Shaun explains that he looks for founders who feel they have no option but to succeed, drawing a comparison to immigrants or those without a fallback, which can drive relentless focus and fortitude.Signals of Early-Stage Investment: Investing at the pre-seed stage involves identifying teams with potential through their work product rather than initial conversations. Challenges of Climate Tech Investing: The difficulty in obtaining clear customer signals within climate tech is highlighted. Shaun notes that genuine customer commitment is hard to gauge and is essential for moving beyond pilot projects.Weathering the Storms: Shaun emphasizes that founders who persist through geopolitical challenges, like supply chain disruptions and tariffs, emerge uniquely stronger. Quote of the Show:“Portfolio math is brutal because it basically says that most companies don’t matter… it’s very easy to say, it’s very hard for founders to accept they may not be that one or two companies." - Shaun AbrahamsonLinks:LinkedIn: https://www.linkedin.com/in/shaunabe/ Website: https://thirdsphere.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube:https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:30 Burned Bridges Mindset03:47 Early Bets And Bad Logos06:20 YC Founder Signal Noise08:48 Work Product Over Pitch11:32 Climate Hardware Realities15:39 Lego Building To Revenue17:29 Tariffs And Supply Chain Chaos20:02 Founders Forged By Turmoil23:54 Why Third Sphere Went Climate26:29 Mission Driven Founder Support27:26 Belief And Reality Checks30:41 Direct Feedback As A VC35:35 Private Credit Replaces Banks39:15 Founder Updates And Trust44:29 Portfolio Math Harsh Truths49:09 Biggest Missed Deal50:46 Next Decade Climate Bets53:16 Outro

What makes a startup truly successful in the eyes of venture capitalists? In this episode of Not Another CEO Podcast, host David Politis sits down with Rudina Seseri, Founder and Managing Partner at Glasswing Ventures, to dive into the realm of venture capital and discuss how startup founders can better position themselves for success.From her experience with early-stage companies to her unique perspective on the dynamics of venture capital, Rudina shares invaluable lessons about the importance of execution, understanding investor expectations, and the intricacies of navigating the startup ecosystem.Takeaways: The Value of Execution: For Rudina, the key trait she seeks in founders is execution excellence. It's not just about having a vision but demonstrating the ability and hustle to deliver beyond expectations.The Misunderstood VC Role: Many founders and employees don't understand the source of venture capital. Knowing that VCs manage funds from institutions like endowments and pensions changes the stakes and expectations.Importance of Strategic Partnerships: Rudina advises founders to seek investment from firms and partners that align with their stage and needs, rather than solely pursuing big names which might not provide necessary support.The Art of Quick Decision-Making: Efficiency in decision-making during early meetings can shape successful partnerships. Rudina values honesty in communicating why a VC might pass on an opportunity, emphasizing that a quick, thoughtful no is better than indecision.Sustained Support Post-Investment: At Glasswing Ventures, support continues beyond just funding, emphasizing talent acquisition, customer connections, and strategic guidance, ensuring startups grow sustainably.Quote of the Show:“What have we done for them lately to deserve to expect? Yes we’ve provided capital, but that’s not enough in my book." - Rudina SeseriLinks:LinkedIn:https://www.linkedin.com/in/rudinaseseri/   Website: https://glasswing.vc/  Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube:https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:37 Ruthless Execution02:32 Spotting Hustle Fast05:38 Execution in the AI Boom07:55 Retention and Switching Costs10:08 AI Interest vs Intent13:19 AI Hype and Human Loop17:58 How VCs Decide Quickly20:39 Giving Fast Honest Nos22:54 Execution and Go To Market Gaps24:21 How VCs Support Founders27:14 Portfolio Review Cadence28:27 Why Take Board Seats33:30 Term Sheets Beyond Valuation38:17 Choosing Firm vs Partner41:29 Scaling Support With Team43:01 Why She Became an Investor45:14 Outro

How do you choose an investor you’ll still trust when things inevitably get hard?In this episode, Ian Sigalow offers a candid, unfiltered look at early-stage investing and the founder–investor relationship, including one of the most sobering truths first-time founders often learn too late: it’s far harder to unwind a bad investor than a bad marriage. Drawing from decades of experience backing companies and founders at Greycroft, Ian breaks down how great investors actually think, decide, and engage behind the scenes.Ian shares what he looks for in exceptional founders, why the explosion of startups hasn’t increased the number of true breakout winners, and why most board meetings fail to create real value. This episode is a must-listen for any CEO navigating fundraising or building their first long-term investor relationships. Takeaways: Master of Two Domains: Sigalow emphasizes the importance of founders who excel in both product understanding and sales, calling them "masters of two domains" who are rare and invaluable.Big Market Potentials: Ian points out the essential need for startups to target significantly large markets. In the entrepreneurial world, having the potential to scale a company to a billion-dollar business is vital.The Earned Secret: A distinctive aspect investors look for is the "earned secret."The Importance of Trust in Investor Relationships: Sigalow stresses that founders should only take money from investors they trust, highlighting the lasting nature of these partnerships. Controlling the Board Meeting: Effective CEOs maintain control over board meetings, ensuring the focus remains on strategic issues rather than getting sidetracked. Quote of the Show:“A CEO should never take money from someone they don’t trust. It’s harder to get out of a bad investor than a bad marriage." - Ian SigalowLinks:LinkedIn: https://www.linkedin.com/in/iansigalow/ Website: https://www.greycroft.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube:https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:32 Founder's Qualities and Market Potential03:01 The Importance of Earned Secrets03:57 Challenges in Identifying Exceptional Founders06:12 The Evolution of Venture Capital17:42 The Role of Technology in Venture Capital21:45 Focus on Early-Stage AI Investments26:40 Choosing the Right Investment Partner10:50 Onboarding Process at Greycroft27:50 The Rule of Three in Communication29:24 Key Metrics for Founders31:21 The Role of Board Meetings38:26 Understanding Venture Capital Dynamics18:46 Ian's Journey into Venture Capital48:04 Outro

How do you lead at scale when the role constantly asks you to stretch past what feels possible?In this episode, Irina Novoselsky shares the honest, vulnerable truth behind leading at the highest levels: the job isn’t about having every answer, it’s about choosing to step into roles, decisions, and moments that stretch you and reveal what you’re capable of. Irina brings deep experience from modernizing CareerBuilder and now leading Hootsuite, the world’s most widely used social media management platform trusted by millions of users. Irina walks through the systems, disciplines, and mindsets that have shaped her career, from the 15-minute weekly all-hands that transformed Hootsuite’s culture, to her 100-day onboarding playbook, to redefining the company’s ICP in 10 days and doubling growth. She also breaks down how Gen Z will reshape every company’s go-to-market motion, why naivete is an early-career superpower, and how her immigrant upbringing forged the resilience she leads with today. Takeaways: Embrace Focus and Prioritization: Irina emphasizes the addictive nature of focus and its role in driving growth. By identifying core strengths and doubling down on them, businesses can achieve unparalleled success.Redefine Company Rituals: Hootsuite’s unique weekly 15-minute all-hands meeting, serves as a crucial touchpoint. It's a tightly produced session that keeps the team energized and informed.Foster Transparency and Engagement: For Irina, transparency is key. She advocates for open communication and regular Q&A sessions, encouraging feedback, even the uncomfortable truths.Quote of the Show:“I get scared frequently. I put myself in vulnerable moments all the time… but those are the moments when you realize you can do hard things." - Irina NovoselskyLinks:LinkedIn: https://www.linkedin.com/in/irina-novoselsky/ Website: https://www.hootsuite.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube:https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:10 Irina's Leadership Style and Hootsuite's All Hands Meetings06:53 The Importance of Transparency and Feedback08:49 First Steps as a New CEO14:27 Identifying Key Players and Cultural Carriers18:14 The Power of Focus and Prioritization23:53 Communicating with Investors and Board Members26:35 The Role of Social Media and Personal Branding28:42 Creating a Resonant Culture29:20 The Power of Social Media for CEOs30:31 Understanding Gen Z's Buying Behavior33:15 Challenges and Growth as a CEO36:18 The Importance of Vulnerability and Mentorship51:17 Transitioning from Finance to Operations54:03 Final Reflections and Advice59:04 Outro

Can experience truly make a difference in the startup world? In this episode of Not Another CEO Podcast, David Politis speaks with Vanja Josifovski, Co-Founder and CEO of Kumo, to explore the journey of leading a cutting-edge AI enterprise. From his prestigious roles at Pinterest and Airbnb to founding Kumo, Vanja shares the lessons learned, the dilemmas faced, and the excitement of turning vast amounts of relational business data into actionable predictions.Takeaways: The Importance of Co-founders: Vanja emphasizes the critical role of choosing the right co-founders. He stresses the importance of complementary skills and experiences that create a sustainable and successful leadership team.Understanding Market Adaptability: A major challenge for technical founders can be the transition to understanding the go-to-market strategies. Vanja shares the struggles of innovating while aligning with market needs and effectively communicating product value.The Journey From Idea to Reality: Vanja sheds light on how Kumo's idea sprouted from a simple yet groundbreaking aspiration to simplify the process of turning enterprise data into predictions without the complex machine learning cycle.Raising Capital in the Current Climate: Although initially easy due to Vanja's background, he warns about the “honeymoon phase” in fundraising and the necessity of making money quickly, even when resources are abundant.The Art of Unlearning: As Vanja continues his journey, he highlights unlearning as key to adapting to new challenges. The ability to let go of old practices and adopt new methodologies is vital for growth and evolution.Quote of the Show:“It’s always easier to watch somebody do things and criticize… if somebody’s watching you from the side, they’ll always find something wrong." - Vanja JosifovskiLinks:LinkedIn: https://www.linkedin.com/in/vjosifovski/  Website: https://kumo.ai/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:24 The Importance of Choosing the Right Co-Founders04:44 Defining Roles Among Co-Founders06:49 Challenges of Being a CEO10:22 Hiring and Building a Team12:54 Raising Capital and Investor Relations15:21 Kumo's Product and Market Fit18:57 Pricing Models and Strategies24:28 Acquiring the First Customers28:28 The Intensity of Starting a Company at 5032:33 The Importance of Unlearning as a CEO37:13 Challenges in Go-to-Market and Fundraising39:14 Kumo's Vision for the Future42:28 From Macedonia to Silicon Valley52:54 Advice to My Younger Self53:39 Outro

How do founders navigate the intricacies of investor relationships to scale iconic companies? In this episode of Not Another CEO Podcast, David Politis speaks with Amish Jani, co-founder and partner at FirstMark Capital, about key considerations for both investors and founders in the venture ecosystem. Amish discusses his criteria for investment, the importance of understanding the 'why' behind a founder's journey, and the strategic approach to board meetings. He also sheds light on the dynamics of venture partnerships, the evolving focus of SaaS in the AI era, and the burgeoning startup ecosystem in New York City.Takeaways: The Power of the “Why”: Amish emphasizes the importance of understanding the founder’s unique perspective on their problem. The "why" behind their journey not only reveals their depth of understanding but also what drives them to pursue their vision.Investor-Entrepreneur Fit: Amish highlights that mutual compatibility and alignment of values between the investor and the entrepreneur significantly enhance the collaboration's success over a long-term journey.Adaptability and Focus as Key Ingredients for Success: While having a clear vision is significant, the ability to adapt and listen to market feedback can sometimes pivot a company to more promising directions.Product-Market Dynamic and Competitive Edge: Amish talks about the emphasis on distribution, data acquisition, and building unique advantages that distinguish companies from competitors who may quickly replicate similar functionalities.Quote of the Show:“ We're not in a control business, we're in an influence business. And if you lose someone's ears, that's just as bad as not saying something at all." - Amish JaniLinks:LinkedIn: https://www.linkedin.com/in/amishjani/ Website: https://www.firstmark.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube:https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:19 Amish’s Investment Philosophy02:38 The Importance of 'Why' in Founders03:40 Evaluating Founders and Their Vision05:08 The Role of Product and Market Understanding06:13 Challenges and Insights in Venture Capital08:30 Investor-Founder Fit and Long-Term Relationships21:07 The Importance of Choosing the Right Investor21:56 The Role of Founders in Shaping Company Culture23:09 Navigating Hard Conversations with Founders25:54 Effective Board Meetings: Moving Beyond Sales Pitches30:04 The Current State of AI and Market Dynamics37:06 The Evolution of New York's Tech Ecosystem41:26 Why Amish Became an Investor43:47 Outro

Can imposter syndrome drive you to succeed? In this solo episode of Not Another CEO Podcast, David explores his personal experiences with imposter syndrome and shares valuable insights gathered from countless conversations with leaders who have faced similar challenges.Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #FebruaryCEOPulseChapters:00:00 Intro00:51 Personal Experiences with Imposter Syndrome03:04 Defining Imposter Syndrome04:56 The Two Paths of Imposter Syndrome06:48 Channeling Imposter Syndrome for Growth09:02 Practical Advice for Dealing with Imposter Syndrome13:28 Outro

Have you ever wondered how leaders manage to scale their organizations without being involved in every intricate detail? In this week’s episode, David Politis welcomes David Karandish, Founder and CEO of Capacity. Together, they delve into the art of building compound startups, scaling intricately interconnected businesses, and the profound role AI plays in today's market dynamics. Takeaways: The Compound Startup Strategy: David Karandish introduces the concept of a "compound startup," a term coined by Parker Conrad that he has effectively applied at Capacity. The premise revolves around integrating various point solutions into a cohesive platform, reducing costs while maximizing the bundle's value.Navigating Mergers and Acquisitions: Handling 14 company acquisitions in just three years, David shares his approach to successful mergers. He emphasizes the importance of each acquisition fitting into the broader company mission, fostering synergy rather than assembling a mere collection of brands.Building Machines in Business Processes: David advocates for creating “machines,” repeatable processes that enhance efficiency and scalability within an organization. Impact of AI on Business Operations: The discussion highlights the evolving landscape of AI solutions. While initial efforts centered around point solutions, the trend is shifting towards platform consolidation.The Role of Communication Frameworks: David reflects on how establishing a structured cadence for goal setting and meetings has been vital at Capacity, ensuring alignment across 350+ employees worldwide.Quote of the Show:“By machine, I don't necessarily mean how you think like a physical idea, but I mean more repeatable processes that scale and remove as much human decision making outta the process as possible." - David KarandishLinks:LinkedIn: https://www.linkedin.com/in/davidkarandish/Website: https://capacity.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Chapters:00:00 Intro01:43 The Concept of a Compound Startup04:09 Strategic Acquisitions and Integrations05:41 Challenges and Solutions in M&A09:24 The AI Revolution and Market Trends13:01 Implementing EOS and Organizational Frameworks17:38 Building and Operating Effective Machines21:12 Hiring for Stage Fit and Problem Solving27:57 St. Louis Entrepreneurial Scene33:39 AI and Market Noise38:53 Big Breaks and Business Models41:28 Managing Energy and Time43:34 Balancing Work and Family47:35 Advice for Aspiring Entrepreneurs48:31 Outro

How do you know if a company is actually building momentum, or just looking polished on the surface? In this episode of Not Another CEO Podcast, David sits down with Jeff Morris Jr., Founder and General Partner at Chapter One, to break down what truly matters at the earliest stages of building a company. Jeff invests at pre-seed and seed, where ambiguity is high, data is limited, and speed of learning is often the only real signal. Before becoming an investor, Jeff was an early product leader at Tinder, helping scale the product to hundreds of millions of users, an experience that deeply shapes how he evaluates founders today.Jeff shares how he thinks about product velocity, founder self-awareness, team dynamics, and why the individual partner matters far more than the firm logo. This conversation is a masterclass for CEOs building from zero to one and choosing who they want in the trenches with them. Takeaways: Product Velocity Matters: Jeff emphasizes the importance of product velocity, especially in the early stages of a startup. He explains that founders need to run numerous experiments to achieve product-market fit, often partnering with technical leaders to accelerate this process.Building the Right Team: According to Jeff, a strong indication of a founder's potential is their ability to attract a talented team. He believes that successful founders often draw in colleagues from their previous ventures, creating a "band" that's been together through various challenges.The Sales Dilemma: Founders with technical expertise often lack strong sales skills. Jeff looks for self-awareness in founders, assessing if they can identify their weaknesses and augment them with the right partners or co-founders.The Importance of Early Impressions: First impressions are crucial in the VC world. Jeff and David both agree that initial meetings often determine whether an investor leans in. Founders should craft a compelling story and use the first few minutes to capture interest.Aligning with the Right Investor: For Jeff, investing is akin to a decade-long partnership. He advises founders to seek investors who align with their vision and are genuinely interested in their success, rather than just providing capital.Preparation and Self-Awareness: Founders need to be brutally honest about their strengths and weaknesses. Jeff advises preparing thoroughly before meeting investors and leveraging one's unique strengths while addressing weaknesses to form a complete leadership package.Quote of the Show:“We talk a lot about product velocity being the most critical metric we look for." - Jeff Morris Jr.Links:LinkedIn: https://www.linkedin.com/in/jeffmorrisjr/ Website: https://chapterone.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #ChapterOneChapters:00:00 Intro01:10 Key Metrics for Early-Stage Investments02:37 Assessing Founders and Teams07:51 The Importance of Self-Awareness in Founders10:38 The Founder-Investor Relationship14:34 Navigating the Venture Capital Landscape19:12 The Dynamics of Fundraising27:36 The Current Investment Climate41:44 Jeff Morris, Jr.'s Journey to Venture Capital44:39 Outro

How do you create a work culture that stands out and inspires team loyalty across multiple companies? In this episode, we gain valuable insights on this and more from the illustrious career of Donna Dubinsky. Known for her pivotal roles at Palm Computing and Handspring, Donna offers a rare long-term perspective on leadership, culture, and the technological landscape that has spanned decades. Takeaways: The Importance of Building a Strong Culture: Donna emphasizes that a great company starts with great people. She shares the crucial role a positive culture played in her companies, stating that when you foster an environment people love, they follow you from venture to venture.Adaptability is Key: One of the most sought-after traits in employees, according to Donna, is flexibility. She highlights the importance of hiring individuals who are not rigid in their thinking but can pivot and grow with the company.Challenges of Raising Capital: Donna recounts the struggles in securing investment for Palm, despite her extensive network. She faced skepticism from investors due to previous failures in handheld computing and the prioritization of internet ventures over hardware.Reflective Organizational Planning: Donna shares her strategic approach to planning through biannual offsites, fostering a culture of reflection and adjustment. These sessions not only solidified strategic objectives but also enhanced team camaraderie through collaborative efforts and fun activities.Maintaining Integrity and Respect: Donna’s overarching advice is to treat everyone with respect. This principle was foundational in building the cultures of her companies and remains a critical lesson for sustainable leadership.Quote of the Show:“I really appreciated people who could deal with change. Changing circumstances, changing environment, changes within the company, as opposed to people who were rigid." - Donna DubinskyWays to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #Handspring #PalmChapters:00:00 Intro01:30 The Importance of People in Building Companies03:42 Creating and Maintaining Company Culture16:00 The Palm Story: Revolutionizing Personal Computing37:09 Frustrations of Being an Employee37:44 Challenges of Selling a Company39:02 Balancing Structure in Big Companies40:55 Starting Handspring and Product Focus45:03 Biggest Mistake at Handspring49:00 Advice for Fast-Growing Companies50:28 Impact of AI and Market Dynamics55:05 Personal Background and Career Beginnings57:33 Big Breaks and Mentorship01:03:06 Government Service and National Impact01:07:49 Outro

How do great founders use their best moments, not their hardest ones, to build the future of their company?In this episode, Jules Maltz shares the mindset that has guided him through decades of backing generational companies like Slack, Dropbox, Grammarly, MuleSoft, G2, and Buddy Media. For Jules, the brightest periods in a company’s journey are the moments to build aggressively: to hire exceptional executives, deepen product moats, and prepare for act two and act three long before the market forces the issue.Jules also opens up about what he looks for in founders, why authenticity matters more than pitch polish, and how trust is built in the first months of an investor–founder relationship. He reflects on his own misses, the evolution of venture capital, and the emotional clarity that underpins his earliest investment decisions.  Takeaways: Authenticity and Passion are Essential: Jules emphasizes the importance of authenticity and passion in founders. He looks for individuals who have a genuine drive and a personal connection to the problem they are solving.Beyond the Metrics: When evaluating potential investments, Jules seeks stories that transcend traditional metrics. He recalls his first investment in Twitter, where the pitch focused more on the transformative potential of the platform rather than immediate financial returns.Building Trust Early On: Establishing trust during the initial months after an investment is crucial. Jules believes that consistently delivering on promises and being genuinely helpful builds credibility.Adapting Communication Styles: Jules adapts his communication style based on the needs of each CEO. Some prefer regular updates, while others might communicate only during key events.Sustaining Growth Through Strategic Hiring: Jules advises companies to recruit strong executives and think ahead about their business strategies during periods of growth. By doing so, businesses can better navigate market changes and sustain their growth trajectory.Nurturing Relationships for Long-Term Success: Relationships are at the heart of venture capital. Whether it's trust between founders and investors or maintaining connections with past business partners, nurturing these relationships can lead to long-term success and learning.Quote of the Show:“When the sun is shining on your business, that’s a great time to recruit super strong executives and think about act two and act three." - Jules MaltzLinks:LinkedIn: https://www.linkedin.com/in/julesmaltz/ Website: https://www.ivp.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #IVPChapters:00:00 Intro01:25 Key Traits of Successful Founders03:52 The Importance of Authenticity06:17 Evaluating Investment Opportunities10:59 The Twitter Investment Story21:57 Building Trust with Founders27:11 Trusting Your CEO's Vision29:31 Navigating Hypergrowth and Market Changes33:53 The Excitement and Challenges of AI Investments41:51 Teaching and Sharing Venture Capital Insights47:24 The Role of Trust in Venture Capital50:35 Biggest Investment Regrets53:31 Outro

How can you get the most out of your year-end? In this solo episode of Not Another CEO Podcast, David explores how leaders can leverage the end of the year for reflection, rallying their troops, and recharging for what lies ahead.Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #DecemberCEOPulseChapters:00:00 Intro01:22 Reflect: Assessing Achievements05:15 Rally: Energizing Your Team11:14 Recharge: Taking Time to Rest13:33 Outro

How do you keep building when every month your company is almost out of money, and quitting would be the logical choice?In this episode, Artem Rodichev shares the gritty, unfiltered story of Ex Human’s near-death year. Instead of shutting the company down, that year hardened the team, shaped the culture, and created a level of resilience that became Ex Human’s defining advantage.Now Ex Human is profitable and building empathetic AI characters capable of multimodal emotional intelligence, technology designed to see, hear, and feel in ways that help combat loneliness. Artem also discusses his path from leading AI at Replica to building a company that spans both consumer and enterprise markets, powered by millions of user-created AI characters that generate a unique data advantage.  Takeaways:Persistent Belief in Your Vision: Artem emphasized the importance of having unwavering belief in your mission. His steadfast belief in the potential of AI to create meaningful human interactions kept him going through challenging times.Foster a Culture of Resourcefulness and Persistence: The trials that Ex Human endured became pivotal learning experiences, instilling a culture of resourcefulness and persistence within the team. Be Prepared for Sacrifices: Artem candidly discussed the personal sacrifices he made, including taking a salary below market rate and making hard personnel decisions. Expand Beyond Comfort Zones: Despite an engineering background, Artem knew he needed to step out of his comfort zone and learn essential skills like marketing and sales to lead Ex Human effectively.Data-Driven Innovation: Ex Human’s success hinges on continuously refining their AI models with data collected from their consumer app. This iterative approach allows them to stay ahead in the competitive AI market.Transitioning from a Stable Job to Entrepreneurship: Artem’s move from a significant role at Replica to founding his startup showcases the courage needed to leave stability behind in pursuit of a bigger vision.Quote of the Show:“Every month I thought I should give up. But then the other side of me said, if you give up now, you’ll never build the future you believe in." - Artem RodichevLinks:LinkedIn: https://www.linkedin.com/in/art-rodichev/ Website: https://exh.ai/#home Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #ExHumanChapters:00:00 Intro01:24 The Importance of Persistence04:33 Belief in the Vision05:53 Personal Sacrifices and Company Culture11:07 Solo Founder Challenges12:29 Building a Strong Team14:45 The Role of a Founder18:47 Consumer AI and Empathetic Companions29:41 Breaking Inertia: Leaving a Successful Company32:06 Limitations and New Opportunities: The Birth of a New Venture34:50 B2C and B2B: Balancing Two Markets37:11 The Importance of Data in AI Development42:28 Challenges and Competitions in the AI Market49:41 Personal Background: From Kazakhstan to Tech Entrepreneurship57:00 Final Reflections and Advice for Aspiring Entrepreneurs58:39 Outro

How do you scale a company from zero to $100 million in 18 months without losing quality, clarity, or control?In this episode, Matt Price shares the remarkable story of building Crescendo, one of the fastest-growing companies ever featured on the show, by reimagining customer experience through advanced AI and deeply trained specialists. Matt’s journey has come full circle: from a technical support rep early in his career, to scaling Zendesk, to now creating an entirely new model for enterprise-grade customer care.Matt opens up about assembling an elite leadership team in record time, creating a vertically integrated product-and-operations engine, and designing a culture anchored around accountability, curiosity, and constant communication. He also explains why outcome-based pricing changes everything, how General Catalyst’s creation model gave Crescendo an unfair advantage, and why traditional BPOs simply aren’t positioned for the AI era. This is a masterclass in speed, focus, and operational excellence. Takeaways:Building a Stellar Team: Matt emphasized the importance of assembling a high-quality team quickly. He discussed how bringing in top talent, especially those with experience in related fields, has been crucial for Crescendo's rapid growth.Curiosity and Vision as Key Attributes: When recruiting for a fast-growth environment, Matt values curiosity and passion for the company's vision. These attributes, combined with relevant experience, are critical for innovation and progress.Prioritizing Outcomes Over Traditional Models: Crescendo has embraced outcome-based pricing, aligning the company’s success with customer satisfaction. This model contrasts with traditional seat-based pricing and encourages the entire organization to focus on end-to-end service quality.Integrating AI Thoughtfully: Matt spoke about the evolution of AI in customer care and its potential to transform the industry. By integrating AI with human expertise, Crescendo offers enhanced support experiences.Strategic Acquisition for Growth: The strategic acquisition of traditional BPOs has allowed Crescendo to expand its distribution and offer scalable AI solutions. Matt's approach underscores the power of mergers and acquisitions in achieving rapid growth.Creating a Culture of Accountability: Matt stressed the significance of having someone accountable for leading every project or initiative. In a fast-paced environment, clarity in roles and responsibilities is vital for efficiency and progress.Fostering Open Communication: Maintaining open communication channels, even in remote settings, is a priority for Crescendo's leadership. Matt ensures his team stays connected through regular meetings and an open-door policy.Quote of the Show:“Customer care was constrained by the economics. In order to deliver customer care up to now, you have to put humans in, a lot of people in… and AI now changes that, AI puts us into a world of abundance. And we need to shift our mindsets now as CX leaders… we’re moving from being deflectors to creators and innovators." - Matt Price Links:LinkedIn: https://www.linkedin.com/in/growthspecialist/ Website: https://www.crescendo.ai/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #CrescendoChapters:00:00 Intro01:32 Building a High-Impact Team03:40 The Role of AI in Customer Service06:03 Rapid Growth and Company Evolution07:58 Leadership and Team Dynamics11:03 AI Integration and Product Development21:53 Founding Crescendo and Market Opportunities28:10 Challenges and Focus as a CEO31:08 The CEO's Influence on Team Dynamics35:00 Outcome-Based Pricing in SaaS36:22 Challenges and Benefits of Outcome-Based Models41:25 Strategic Growth Through Acquisitions47:04 The Future Vision for Crescendo48:34 Personal Journey and Early Career58:33 Advice for Aspiring Entrepreneurs59:29 Outro

Have you ever wondered what it takes to build a company from your garage to a public entity?In this episode, Chieh Huang shares the raw, unfiltered story of building Boxed from a garage into a national e-commerce brand serving tens of millions of customers, and the emotional toll, unlikely breakthroughs, and market forces that shaped every chapter of the journey. He reflects on the lonely months of almost no orders, the overnight surge that changed everything, the pressure of becoming a public company CEO, and the reality that even the strongest operators can’t outrun macro cycles.Chieh also opens up about what happens after the final chapter closes, the exhaustion, the identity shift, and the unexpected necessity of real recovery. His honesty about the highs, lows, and lessons he’s taking into his next company makes this a powerful episode for founders navigating their own versions of the broken-glass analogy. Takeaways: From Humble Beginnings to a Notable Success: Chieh Huang started Boxed in 2013 right from his garage, with only dreams and a strong will to succeed. Within a few years, Boxed scaled to become a renowned online wholesale retailer, serving millions.The Challenge of Maintaining Purpose: Chieh emphasizes the importance of cultivating an intrinsic purpose within a company. At Boxed, the sense of purpose wasn’t predefined but evolved over time as the team grew, particularly among the fulfillment center workers.The Rollercoaster Ride of Fundraising: Chieh's journey wasn't without financial hurdles. While initial investments were relatively easier owing to his prior success in the gaming industry, subsequent rounds posed challenges, reflecting the inconsistent nature of venture funding.Consumer Business Dynamics: Chieh discusses the unpredictability of consumer businesses, highlighting how a single viral moment or endorsement can drastically influence a company's success, unlike enterprise businesses that grow through steady acquisition of clients.Public Company Experience: Huang's experience in taking Boxed public via a SPAC (Special Purpose Acquisition Company) taught him that public market dynamics significantly differ from private venturesHandling Burnout: Chieh and David discuss the inevitability of burnout in an entrepreneur's journey and the importance of managing it proactively through short breaks, personal downtime, and stepping away when necessary to recharge.Quote of the Show:“Being a CEO is like trying to be the greatest of all time in a broken glass eating competition." - Chieng HuangLinks:LinkedIn: https://www.linkedin.com/in/chiehhuang/ Website: https://boxed.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #BoxedChapters:00:00 Intro00:46 The Journey of Boxed02:42 The Purpose Behind Boxed07:14 Starting in the Garage09:23 The Big Break and Rapid Growth20:36 Fundraising Challenges and Successes26:02 Navigating Market Ups and Downs32:09 Reflecting on Past Experiences33:59 Journey to Going Public36:26 Challenges of Being a Public Company CEO39:22 Navigating Investor Relationships44:17 Balancing Work and Avoiding Burnout50:03 The End of Boxed and New Beginnings55:03 Early Entrepreneurial Spirit57:54 Role Models and Mentors01:01:25 Core Motivations and Advice01:05:51 Outro

When was the last time you paused long enough to thank the people who quietly helped you build?In this special compilation episode, we highlight moments from eleven CEOs who reflected on the investors that shaped their companies’ trajectories, not just through capital, but through conviction, guidance, and belief. These clips reveal how the right investors help founders stay grounded in their mission, navigate uncertainty, and make better decisions during pivotal moments of growth.Across these stories, one theme stands out: exceptional investors don’t just finance a business, they help founders become better leaders. They open doors, challenge thinking, and offer support that often goes unspoken and uncelebrated. As we head into the holiday season, this episode is an invitation for CEOs to pause, reflect, and acknowledge the people whose partnership made the climb possible.Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess Chapters:00:00 Intro02:17 Daniel Chait - Greenhouse02:54 Kyle Porter - Salesloft06:50 Craig Walker - Dialpad13:24 Dane Atkinson - Odeko21:11 Diego Oppenheimer - Algorithmia24:46 Itamar Friedman - Qodo28:43 Jeron Paul - Spiff34:03 Nadia Boujarwah - Dia&Co38:59 Nick Patrick - Radar44:16 Toby Kraus - Lightship53:30 Tom Buiocchi - ServiceChannel54:09 Outro

How can you motivate your team to embrace AI in their daily work? In this solo episode of Not Another CEO Podcast, David discusses strategies to drive an AI-first mindset in your company.Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #NovemberCEOPulseChapters:00:00 Intro03:16 Get Your Team Using AI06:24 Get Traction With Focused AI Projects10:42 Install A Champion To Own AI14:00 Outro

How do you build one of the fastest-growing integration platforms in tech, while keeping culture, momentum, and innovation in sync?In this episode, Shensi Ding, Co-Founder and CEO of Merge, shares her journey from investment banking to leading one of the most successful integration infrastructure companies in the market. She opens up about the company’s evolution, from a small startup in San Francisco to a category leader powering technology products and AI agents for companies like Ramp and OpenAI.Shensi also discusses how she built Merge’s in-person culture during the height of the pandemic, what it takes to recruit top talent, and the lessons she’s learned about decision-making, adaptability, and sustaining momentum as a founder. Takeaways: The Importance of Company Culture: Shensi emphasizes the significance of maintaining an in-person culture at Merge, even amidst the challenging conditions of the COVID-19 pandemic.Maintaining Quality Over Competing on Price: Shensi discusses the challenge of maintaining a premium product in an environment saturated with copycats. She was inspired by the CEO of Gong, who reinforced that a company cannot be both the best and the cheapest.Navigating Growth and Innovation: An integral part of Merge's ethos has been to constantly innovate and adapt, which Shensi highlights by discussing the launch of new products and their strategic shifts towards AI-driven solutions.Integration and Expansion as Key Growth Drivers: Shensi highlights the significance of diversifying Merge’s product offerings and expanding into new markets to drive growth. By strategically adding categories and aiming for enterprise-level clients, Merge has expanded its market reach and increased its potential for acquiring larger clients.Lessons in Leadership and Adaptability: David and Shensi discuss the value of learning from industry veterans and mentors, which Merge facilitates by inviting successful leaders to speak with their team.Navigating Fundraising and Investor Relations: In discussing fundraising experiences, Shensi highlights the importance of clear differentiation and conveying the unique value of your product to investors. While the initial seed round was challenging, securing well-known investors early on eased future fundraising efforts.Quote of the Show:“You can’t be the best and the cheapest. You need to decide what you want to be." - Shensi DingLinks:LinkedIn: https://www.linkedin.com/in/shensiding/ Website: https://www.merge.dev/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #MergeChapters:00:00 Intro01:40 Starting Merge During the Pandemic02:50 Challenges of In-Person Work Culture03:42 Expanding to New York and International Markets04:50 Maintaining Work Ethic and Decision Making06:42 Evolving Leadership and Learning from Mistakes10:56 Bringing Industry Leaders to Inspire the Team13:56 Acquiring the First Customers16:38 Dealing with Copycats and Maintaining Quality21:08 Product Evolution and Adapting to AI27:59 The Halo Effect of New Products29:59 Promoting AI Tools Internally33:15 Fundraising Challenges and Successes38:08 Moving Upmarket and Adapting41:42 Founders' Background and Journey47:16 Balancing Work and Personal Life50:41 Outro

How do the best founders learn faster, think deeper, and turn that mindset into companies that endure for decades?In this episode, host David Politis sits down with Nikhil Basu Trivedi, Co-Founder of Footwork, one of Silicon Valley’s most respected early-stage investors. Nikhil’s career spans both sides of the table, from co-founding Artsy, the groundbreaking online art platform, to investing in category-defining companies like Canva, Lattice, Frame.io, and The Farmer’s Dog.Nikhil shares how he evaluates founders, why the “slope of learning” is the most important quality he looks for, and how he builds long-term partnerships based on trust, curiosity, and shared ambition. He also opens up about the changing venture landscape, the hype and opportunity of AI, and what it means to be an investor who has truly walked in a founder’s shoes.Understanding the Importance of Learning: Nikhil emphasized the significance of the "slope of learning" in evaluating founders. This refers to a founder's ability to quickly learn and adapt to evolving market conditions, especially in the fast-paced AI era.Making a Lasting First Impression: According to Nikhil, the first few minutes with a potential investor are critical. Whether it's 15 or 30 minutes, founders must capture the investor's attention and highlight their vision's potential.Pitching with Conviction: Nikhil advised founders to clearly articulate why their business has the potential to be massive. It's crucial to strike a balance between ambition and grounded reality.Value of Ongoing Communication: Post-investment, Nikhil stressed the importance of maintaining regular communication between founders and investors. Leveraging AI for Better Investments: Footwork has been proactive in using AI to manage and analyze portfolio companies, allowing them to track company progress and trends efficiently.Empathy from Experience: As a former operator and founder, Nikhil shared his belief that empathy is crucial in the investor-founder relationship. Understanding the challenges founders face allows investors like Nikhil to be better partners, offering thoughtful guidance rather than prescriptive advice.Quote of the Show:“In the first 30 minutes with a founder, I’m trying to assess their slope of learning… We invest in slope, not just smarts. How fast a founder learns matters more than what they know on day one." - Nikhil Basu TrivediLinks:LinkedIn: https://www.linkedin.com/in/nikhilbt/ Website: https://www.footwork.vc/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #Footwork Chapters:00:00 Intro01:27 Key Traits in Founders: The Slope of Learning04:59 The Importance of First Impressions in Pitching13:48 Evaluating and Supporting Portfolio Companies19:44 The Impact of AI on Venture Capital24:04 The Value of Thought Partnership31:10 Reflections on Missed Opportunities and Career Choices36:30 Future Aspirations for Footwork 38.25 Outro

How do you build something meaningful without losing yourself in the process?In this episode, David talks with Betsy Fore, Co-Founder and former CEO of Tiny Organics and Founding Partner of Velveteen Ventures. Betsy shares her remarkable journey from toy inventor to serial entrepreneur and impact investor, becoming the first Native American woman to raise a Series A along the way.She opens up about co-creating Tiny Organics alongside 100 founding families, facing setbacks like her unaired Shark Tank appearance, and learning to redefine success through purpose and presence. Betsy also reflects on the lessons that shaped her new book, Built on Purpose, blending practical entrepreneurship with spiritual grounding and a values-driven approach to leadership.Now, through her venture fund and nonprofit, Betsy is focused on investing in solutions that uplift communities, children, and the planet, showing that business can be both profitable and deeply purposeful. Takeaways: Unforgettable Beginnings and Tiny Organics' Success: Betsy's tale begins with her concept of engaging 100 founding families, transforming them into co-creators of Tiny Organics and fostering community-driven innovation.Embracing Challenges and the Road Less Traveled: Betsy's first entrepreneurial venture, a Fitbit-like product for dogs, taught her the significance of understanding consumer behavior and product-market fit. A Unique Shark Tank Experience and Fundraising Insights: Navigating numerous challenges, including a memorable Shark Tank experience, Betsy shares insights into the traditional venture fundraising path and the nuances of raising capital, particularly as a Native American woman.Discovering Purpose Beyond Business: Betsy's inspiration for her debut book, Built On Purpose, stemmed from a desire to demystify the practice of manifestation and align it with business creation.Melding Investment with Impact: Through Velveteen Ventures, Betsy shifts her focus towards using her skills to benefit her community and the broader planet. Her investments in healthcare, climate, and solutions for children.Quote of the Show:“The most important relationship a founder can have isn’t with investors or customers. It’s with themselves." - Betsy ForeLinks:LinkedIn: https://www.linkedin.com/in/betsyfore/ Website: https://www.tinyorganics.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #TinyOrganics #VelveteenVenturesChapters:00:00 Intro01:26 Building Tiny Organics with Founding Families07:47 From Tiny Organics to National Recognition08:34 Lessons from a Previous Venture13:51 Shark Tank Experience19:18 Navigating the Venture Capital Landscape25:07 Securing Initial Funding and Building a Strong Advisory Board26:15 Realizing the Importance of Giving Back27:55 Founding Natives Rising and Healing Through NLP29:20 Investing in Underrepresented Founders31:39 Writing 'Built on Purpose' and the Power of Manifestation35:38 Inspiring Stories from Native American Founders38:21 Launching a Venture Fund with a Purpose41:26 From Rural Illinois to International Success49:35 The Importance of Self-Compassion for Founders50:35 Outro

How do you scale exceptional customer support without losing the human touch?In this episode, David sits down with Ryan Wang, Co-Founder and CEO of Assembled, to explore this very challenge. What started as a simple scheduling tool has evolved into an AI-powered customer support platform trusted by leading companies like DoorDash and Salesforce.Ryan opens up about the realities of scaling a fast-growing company, balancing innovation with culture, leading through learning, and keeping mission and execution at the heart of everything. His insights offer a playbook for founders and leaders aiming to build resilient, adaptable organizations.Takeaways:Understanding the Challenge of Scaling Support: Ryan Wang shares insights into the evolution of Assembled, beginning with a fundamental question: how to scale great customer support without losing efficiency..Wearing Multiple Hats: Ryan emphasizes the importance of diving into different roles within a company. For founders, this means deeply engaging with various functions, learning from their challenges, and understanding what excellence looks like.The Art of Networking: The conversation highlights the importance of connecting with top industry leaders to learn and seek guidance. Founders should prioritize genuine learning over mere networking, making it easy for mentors to share their expertise.Adaptability and Product Evolution: Assembled’s journey reflects the necessity of being adaptable. Ryan discusses the creation of a "new products" team to innovate without disrupting the existing structure, showcasing a strategic approach to product development.Facing Cultural Challenges: The transition to AI tools and methods posed cultural challenges at Assembled. Ryan acknowledges how these changes can strain company culture, advising that clear communication and integrating efforts can prevent breaking the company culture.Mission and Execution: Ryan and David discuss how a strong mission and purpose can act as a modern moat for companiesQuote of the Show:“As CEO, your job is to hold the line, even when it breaks hearts, because someone has to protect the long-term vision." - Ryan WangLinks:LinkedIn: https://www.linkedin.com/in/ryanywang/ Website: https://www.assembled.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #AssembledChapters:00:00 Intro01:22 Deep Dive into Leadership and Management04:25 Networking with Industry Leaders09:12 Balancing Multiple Roles as CEO15:31 Transition to CEO Role23:33 Evolution of Assembled's Product29:13 Running Through Y Combinator30:28 Demo Days and Team Dynamics32:16 Staying on Top of Rapid Changes35:53 The Concept of Moat in Business40:22 Adapting to AI and Cultural Challenges45:09 Future Vision for Assembled47:42 Personal Background and Influences52:45 Advice for Aspiring Entrepreneurs55:15 Outro

How can founders build companies that scale without burning themselves out in the process?In this episode, Noah Shanok, Founder and former CEO of Stitcher, reflects on his entrepreneurial journey leading one of the earliest podcast platforms, which ultimately sold to SiriusXM for $325 million. He shares candid lessons from the early days of Stitcher, navigating sleepless nights, hiring versatile early employees, and learning from missteps along the way.Noah also discusses how his time at Amazon influenced his approach to structured hiring, why prioritizing personal well-being is critical for long-term effectiveness, and how founders can overcome imposter syndrome. Now working as a coach to entrepreneurs, he brings a unique perspective on balancing growth with sustainability, drawing on both successes and challenges from his own journey.Prioritize Yourself as a Founder: Noah candidly discussed his early days at Stitcher, which were characterized by overworking, sleep deprivation, and unhealthy habits. He advocates for founders to prioritize their well-being to ensure they can think clearly in the short term while remaining effective in the long run.Building the Right Team: Noah emphasized the impact of hiring a versatile team early on. His advice to recruit a "jack of all trades" who can adapt and grow with the company resonates with many startup leaders.Overcoming Imposter Syndrome: Noah addressed the imposter syndrome prevalent among founders. He shared strategies to navigate these feelings by focusing on decision-making confidence and holding oneself accountable.The Importance of Timing and Market Dynamics: Reflecting on Stitcher’s challenges, Noah acknowledged the role of timing and market forces. Factors such as market readiness and timing of product launches are crucial in scaling a business successfully, emphasizing that external shifts can heavily influence a startup’s trajectory regardless of internal effort and execution.Leveraging Strategic Partnerships: Noah’s success in securing high-profile deals started with creating strategic partnerships. By working with seasoned advisors, founders can effectively enter new markets and secure pivotal deals that may hasten growth and establish industry credibility.Quote of the Show:“ I've helped hire hundreds of people at Amazon. If I started another company I would implement a very light version of Amazon's process, and I would do it very, very early." - Noah ShanokLinks:LinkedIn: https://www.linkedin.com/in/noahshanok/ Website: https://startupceo.coach/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #StitcherChapters:00:00 Intro01:42 The Importance of Hiring a Versatile Team Member02:24 Finding the Right Person for the Job07:00 Lessons from Amazon's Hiring Process13:29 Stitcher's Early Business Development Deals21:37 Challenges and Realities of Strategic Partnerships26:53 Coaching Founders: Common Challenges and Solutions32:29 Transformative Changes and New Habits33:13 The Impact of Prioritizing Self-Care37:50 The Power of CEO Support Systems38:24 Dealing with Imposter Syndrome45:24 Lessons from Stitcher: Timing and Market Dynamics48:58 The Drive to Build and Help Others51:50 The Importance of Mentors and Advisors57:25 The Need for a Support System for CEOs59:38 Advice for Founders 1:00:58 Outro

Do you know how essential a support system is for a CEO? In this solo episode of Not Another CEO Podcast, David discusses the often overlooked, yet critical support necessary for CEO success.Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #OctoberCEOPulseChapters:00:00 Intro02:53 The Importance of a CEO Support System03:57 Key Components of a CEO Support System05:10 The Role of Co-Founders and Key Executives07:33 The Value of Executive Assistants and Chiefs of Staff09:24 Leveraging Board Members and Advisors14:38 The Importance of Therapists and Personal Relationships19:16 The Power of CEO Peer Networks21:27 Outro

What can founders learn from an entrepreneur who has built, scaled, and exited multiple companies while reshaping an entire city’s startup ecosystem?In this episode, David Cummings, Founder and CEO of Atlanta Ventures, reflects on his journey building ten companies, including Pardot, which sold to ExactTarget for $95 million, and investing in some of Atlanta’s most successful startups like Calendly and SalesLoft. He shares the guiding principles that shaped his entrepreneurial path, from building a culture-first company to navigating the realities of bootstrapping, scaling, and liquidity events.David also opens up about his role in transforming Atlanta’s tech landscape through Atlanta Tech Village and his ambitious project to redevelop South Downtown into a vibrant startup district. Along the way, he offers candid advice for founders on leadership, resilience, and blending work with life in a sustainable way.Visionary Leadership: Cummings underscores the importance of having a clear and opinionated vision. The strategy of creating a product that provides "the most bang for the buck" without falling into the trap of building every requested feature was crucial to Pardot’s success.Bootstrapping Success: Despite the odds against fundraising in a nascent market, Cummings attributes his company’s success to resilient bootstrapping. This allowed him to maintain control and leverage opportunities like strategic acquisitions without compromising his vision.Cultivating Culture: A major highlight from Cummings' leadership was the deliberate cultivation of a workplace culture that prioritizes being positive, self-starting, and supportive.Balancing Ambitions and Personal Life: As an advocate for the "work-life blend," Cummings emphasizes that while early-stage startups demand an intense commitment, sustaining a balanced life is about integrating passion for work with personal commitments.A Tech Renaissance in Atlanta: Cummings' latest venture involves the redevelopment of a historic part of Atlanta into a vibrant startup district. This ambitious project aims to transform south downtown Atlanta into a living ecosystem for innovation and growth, reinforcing Atlanta’s position as a world-class city with a thriving entrepreneurial community.Quote of the Show:“All the entrepreneur styles are different. But for me personally, I'm that shock absorber style. I recognize that things can be great and things can be bad, and just modulate it for the team." - David CummingsLinks:LinkedIn: https://www.linkedin.com/in/davidcummings/ Website: https://www.atlantaventures.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #AtlantaVenturesChapters:00:00 Intro01:44 Early Challenges and Successes at Pardot02:24 Building a Strong Company Culture03:02 Product Vision and Customer Focus05:55 Transition from Doer to Leader12:49 Bootstrapping vs. Fundraising20:34 The ExactTarget Acquisition31:08 Reflections on Entrepreneurship and Liquidity36:52 Understanding Startup Valuations38:09 Building a Winning Team at Pardot41:17 Investing in Founders with the Right Attributes43:29 The Atlanta Tech Village Journey51:44 Revitalizing Downtown Atlanta01:00:56 David's Entrepreneurial Beginnings01:06:57 Balancing Entrepreneurship and Family01:10:36 Advice for Aspiring Entrepreneurs01:12:50 Outro

THE FIRST EPISODE OF INVESTORS UNFILTERED!What do venture capitalists really look for in founders, and how can CEOs build strong, lasting relationships with their investors? In this episode, Chip Hazard, Co-Founder and General Partner at Flybridge, offers an inside look at how VCs think about evaluating founders, funding opportunities, and long-term partnerships. He shares the traits that consistently stand out and explains how these factors matter as much as business metrics, especially in the early stages.Chip also unpacks the evolution of fundraising, from vision-driven early rounds to later stages where metrics and revenue quality become critical. He reflects on the dynamics of board relationships, the importance of clear alignment on strategy, and why constructive feedback and ongoing communication are vital to scaling effectively. Takeaways:Ambition is Key: Chip emphasizes the importance of passion and ambition in founders. He's looking for those with domain expertise and unconventional thinking.Alignment on Strategy: For founders, aligning on strategy with investors is crucial. Chip notes that understanding an investor’s vision for the company can prevent conflicts and foster a positive partnership.Ongoing Communication: Chip discusses the importance of consistent communication between founders and investors, particularly in the early stages. Regular check-ins on strategy, challenges, and progress help maintain alignment and support.Insightful Board Interactions: The role of a board is to offer perspective and support strategic decision-making. Chip highlights that effective board meetings should align on strategy and not create unnecessary work for the company.Balancing Metrics and Vision: As companies evolve from pre-seed to later stages, the focus shifts from purely vision and team to include metrics and financial performance.The Value of Constructive Feedback: Constructive, honest feedback is essential. Chip stresses that a good VC relationship involves recognizing challenges, offering guidance, and maintaining trust without dictating to the founder.Quote of the Show:“ Startups win on speed. They don’t have anything else other than the ability to execute fast." - Chip HazardLinks:LinkedIn: https://www.linkedin.com/in/chiphazard/ Website: https://www.flybridge.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #FlybridgeChapters:00:00 Intro02:11 The Key Traits of Successful Founders04:09 Assessing Founders Beyond the Pitch06:04 Stages of Investment and What VCs Look For15:36 Working with Founders Post-Investment22:08 The Importance of External Perspectives25:52 Challenges in Board Dynamics30:37 Aligning with Venture Capitalists37:55 Geographical Differences in Startups40:13 Reflections and Regrets in Venture Capital43:18 The Passion for Investing45:47 Outro

What does it take to reinvent an entire industry that’s been rooted in tradition for decades? In this episode, Michael Jacobson, CEO of French Florist, shares his journey from corporate consulting to transforming the floral business.Michael explains how he grew a single 3,000-square-foot location into a $9 million operation by modernizing systems, cutting inefficiencies from the supply chain, and infusing emotion into every part of the customer experience. He also reflects on the challenges of scaling in a traditional industry, the decision to franchise, and the importance of mentorship, high standards, and culture in building a business that lasts. Takeaways:Develop a Strong Brand Identity: A major part of Jacobson’s strategy was creating branding that emphasizes emotional connection, redefining flowers as essential expressions of love rather than luxury items. Listen to Your Employees: Before anything else, Jacobson prioritized understanding the needs of the staff already working in the flower shop. Their insights provided critical low-hanging fruit, such as switching outdated and costly phone systems, which paved the way for larger innovations.Direct-to-Source Supply Chain: By eliminating unnecessary intermediaries in the supply chain, French Florist improved both the quality and cost-efficiency of their products. Direct relationships with flower farms allowed the business to offer fresher flowers with longer shelf life at competitive prices.Prioritize Customer Experience: French Florist’s focus on exceeding customer expectations through personalized service has been crucial. They constantly seek ways to enhance customer satisfaction, such as offering unique video card messages to accompany floral deliveries.Strategic Hiring and Internal Culture: Hiring talented individuals who align with the company’s values and culture has been a priority. Jacobson emphasizes unconventional and thoughtful interview processes to ensure new hires share the company’s vision and drive.Quote of the Show:“ If it ain’t broke, don’t fix it is one of my least favorite sayings. If there’s a better way, I want to find it." - Michael JacobsonLinks:LinkedIn: https://www.linkedin.com/in/michaelrichardjacobson/ Website: https://www.frenchflorist.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #FrenchFloristChapters:00:00 Intro01:38 Transformative Leadership and Infusing Emotion03:22 Building a Culture of Love and Excellence08:25 Hiring for Values and Unconventional Interviews14:51 The Origin Story of French Florist19:19 Initial Challenges and Early Improvements24:36 Revolutionizing the Floral Industry with Technology31:43 Revenue Growth and Optimization33:15 Supply Chain Innovations35:15 Direct Importing from Farms37:36 Challenges in the Floral Industry40:28 Franchising and Expansion48:18 Personal Reflections and Motivation1:01:01 Outro

How can CEOs stay adaptable while leading through pivots, growth, and constant change? In this episode, Scott Voigt, Founder and CEO of Fullstory, shares his journey from a failed first product to creating the leading digital analytics platform used by thousands of companies worldwide. Scott dives into the tough realities of leadership, from making difficult people decisions to evolving as a CEO as the company scales. He opens up about the power of storytelling in fundraising and leadership, the importance of mental well-being, and the lessons he’s learned from being an early builder in Atlanta’s thriving tech ecosystem. Takeaways:The Power of Storytelling: Scott Voigt emphasizes the significance of storytelling in his role as CEO. It's not just about what you say but how you say it. Through effective storytelling, he energizes and aligns his team, creating a shared vision and purpose.Hiring and Building a Strong Team: Voigt discusses the challenges of hiring and the importance of finding the right fit. He stresses the necessity of moving people out quickly if they are not a good fit, even though it can be difficult.Navigating Investor Relations: Scott’s journey of securing funding for Fullstory involved both challenges and triumphs. He shares the importance of being strategic and deliberate in choosing investors and board members.The Journey of Fullstory's Market Fit: Voigt candidly reflects on the evolution of Fullstory's product-market fit. Initially, as the team worked on a different product, they faced numerous rejections. However, the pivot to Fullstory's current offering brought about an immediate and undeniable product-market fit.Overcoming Internal Challenges: Discussing exits, Voigt argues that the company's mission should transcend any individual's role, ensuring continued alignment and progress regardless of internal changes.Quote of the Show:“When your spidey sense tells you something isn’t working with a person, make the change fast. It only gets harder the longer you wait." - Scott VoigtLinks:LinkedIn: https://www.linkedin.com/in/scottmvoigt/ Website: https://www.fullstory.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #FullstoryChapters:00:00 Intro01:36 The Biggest Impactful Decision at Fullstory03:35 The Challenges and Lessons of Letting People Go08:38 Hiring Philosophy and Interview Techniques18:56 The Importance of Storytelling as a CEO24:54 Fundraising Journey and Product Pivot33:38 Reflecting on the Early Struggles37:14 The Importance of Team Chemistry43:28 Navigating the Atlanta Tech Scene48:20 Biggest Challenges and Lessons Learned51:01 Future Vision for Fullstory57:15 Personal Reflections and Advice01:07:53 Outro

How do you scale a global company while transforming an industry as traditional as law?In this episode, Max Junestrand, Co-Founder and CEO of Legora, shares how he’s building the world’s first truly collaborative AI platform for legal services.Max reflects on his unconventional path from engineer to entrepreneur, what it took to win over law firms as an outsider, and why ambition and adaptability matter more than experience in fast-scaling environments. He also opens up about navigating hypergrowth, hiring with intention, and the cultural values that drive Legora’s mission to reshape how legal work gets done. Takeaways:Pioneering Global Expansion: Max's approach to expansion defies conventional paths. Instead of focusing solely on local markets like many Swedish companies, Max boldly decided to expand globally. The Power of Collaboration: Max stresses the importance of a shared mission between stakeholders and service providers, focusing on delivering unparalleled value and continuous improvement in legal services. Hiring and Culture Building: Max places a strong emphasis on ambition and cultural fit when hiring, believing these attributes are crucial for scaling a company. He maintains personal involvement in the interview process to ensure new hires align with the company’s high standards and growth trajectory.Learning and Growing from the YC Experience: Max’s experience with Y Combinator (YC) was transformative. Despite the complexities of maintaining operations during this period, the experience underscored the importance of mentorship and networking.Pushing the Envelope: Max underscores the importance of maintaining a proactive stance in innovation. By consistently exploring new pathways and pushing boundaries, he ensures the company remains at the forefront of technological advancements.Quote of the Show:“ There's a real value in actually being the second mover, and the value comes from two things... You get to see what is the right path and what is the wrong path." - Max JunestrandLinks:LinkedIn: https://www.linkedin.com/in/maxjunestrand/ Website: https://legora.com/ Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #LegoraChapters:00:00 Intro01:41 Founding and Early Challenges02:42 Sales Strategy and Growth06:40 Building a Strong Team13:55 Global Expansion29:43 Expanding Beyond Local Markets31:13 Challenges of Going Global33:40 Product Development and Iteration37:08 Competing with Industry Giants42:43 YC Experience and Early Challenges49:52 Personal Background and Motivation1:00:48 Outro

Ever wondered what to consider when hiring your first key employees beyond the founding team? Or what are the secrets to successful fundraising for startups? In this solo episode of Not Another CEO Podcast, David shares his insights from CEO gatherings, trends he’s noticed in the community, and a recent family trip that emphasizes the importance of origin stories.Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #AugustCEOPulseChapters:00:00 Intro02:55 Hiring Your Founding EA13:08 Fundraising Isn’t Fair18:55 The Importance of Origin Stories23:55 Outro

What does it take to build and scale a company while staying grounded in your values? In this episode, Flint Lane reflects on his journey founding and growing Billtrust and coming out of retirement to start Major League Table Tennis. He shares lessons on resilience, leadership, and the balance between personal integrity and business success. Flint also discusses the challenges of navigating growth, what he has learned about himself along the way, and the importance of staying true to purpose even in difficult times. Takeaways:Scaling Begins with Small Wins: Flint emphasizes the importance of "stacking wins" in business, where each small victory propels you forward. He believes the key to success lies in maintaining momentum and making rapid, intelligent decisions.The Role of Mission and Values: For Flint, defining mission and values within a company is crucial for guiding decision-making processes. These elements serve as the company's moral compass, helping employees make decisions aligned with the organization's goals.Navigating Executive Leadership: Flint shares insights into the dynamics of leadership and succession planning. He describes the challenging process of evolving leadership roles to meet the company's growing demands.Overcoming Cybersecurity Challenges: Flint recounts a severe malware attack that tested the company's resilience. He stresses the importance of investing in robust cybersecurity measures and learning from such incidents to better protect critical business assets.The Power of Transparency: Flint argues for fostering trust and collaboration within the organization. By openly communicating challenges and strategies with his team, Flint was able to cultivate an environment of honesty and collective problem-solving.The Entrepreneurial Lifecycle: Flint illustrates the different stages of a company's growth, each with unique challenges and opportunities. From startup to public company, the journey requires adaptation and learning.Transitioning from Software to Sports: After two decades at Billtrust, Flint embarked on a new venture with Major League Table Tennis, driven by his passion for the sport.Quote of the Show:“Any business is a combination of hundreds of thousands, if not millions of decisions, millions of small, little victories." - Flint LaneLinks:LinkedIn: https://www.linkedin.com/in/flintlane/Website: https://www.mltt.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #MajorLeagueTableTennisChapters:00:00 Intro01:23 Flint Lane's New Venture: Major League Table Tennis01:56 The Importance of Stacking Wins04:06 Effective Communication and Decision Making06:30 The Role of Transparency in Leadership14:51 Hiring the Right People21:06 The Evolution of Executive Teams27:17 The Importance of a Strong Board31:53 Navigating the Startup Journey33:19 The Decision to Go Public36:34 The Acquisition Process39:06 Cybersecurity Crisis43:54 Transition to Major League Table Tennis49:33 Reflections on Entrepreneurship56:46 Final Thoughts and Advice57:48 Outro

How does an aspiring product leader transition to the helm of a successful tech company? In this episode, Nick Patrick shares his unique perspective on leadership and growth in the tech industry.Nick discusses critical insights on how Radar's unique product strategy, company culture, and operational practices have driven their success. Takeaways:Multi-Product Strategy Innovation: Nick emphasized Radar's growth through expanding their product offerings rather than focusing on a singular solution. By catering to diverse customer requests, Radar transitioned from a geo-fencing platform to a comprehensive location service provider.Customer-Centric Approach: Nick underlined the importance of being customer-driven in product development. Radar has prioritized building what customers request, as long as it aligns with their overall vision.Modernizing Company Culture: Radar has seen increased cohesion and morale by embracing a focused mission and maintaining a workplace culture that emphasizes teamwork over rigid organizational roles.Leadership through Uncertainty: Leading through the pandemic, Radar faced significant challenges with clients from the travel and retail sectors. The company pivoted by redefining its strategy, focusing on delivering multiple product solutions, strengthening its market position.The Shift from Remote Work Culture: While embracing remote work during the pandemic, Nick advocated for in-person collaboration as a competitive advantage. By returning to office-based work, Radar has fostered a more cohesive culture and quicker iteration of ideas.Strategic Fundraising Tips: Nick shared valuable insights into securing investment, noting the importance of creating urgency during fundraising and finding investors who truly “get” the company's vision.Quote of the Show:“Either people happen to Radar or Radar happens to them… you wanna hire people like they happen to Radar." - Nick PatrickLinks:LinkedIn: https://www.linkedin.com/in/nicholaspatrick/ Website: https://radar.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #RadarChapters:00:00 Intro01:12 The Impact of Multi-Product Strategy03:16 Challenges and Management of Multi-Product Approach07:43 Product Involvement and Team Structure12:30 Customer-Centric Engineering14:42 In-Person Collaboration and Office Culture19:52 Founding Radar and Early Challenges28:36 Fundraising Journey and Investor Relations34:55 Navigating Business Through Uncertain Times35:47 Adapting to Market Changes and Setting Expectations38:20 Cultural Shifts and Social Issues41:21 Future Vision for Radar43:24 Personal Journey and Entrepreneurial Spirit47:38 Balancing Work and Family Life51:03 Advice for Aspiring Entrepreneurs54:25 Outro

What happens when you jump from a career in finance to tackling the beauty industry? In this episode, Natalie Mackey shares her reflections on building Winky Lux, from bootstrapping to private equity. She opens up about the importance of core values, the challenges of fundraising as a female founder, and the lessons she learned navigating through different growth stages. Takeaways:Importance of Core Values: Natalie emphasizes the transformative impact of clearly defined core values in the evolution of Winky Lux. The company started with general ideals, but crystallizing specific values became vital as the company scaled.Consumer-Centric Approach: A pivotal moment in Winky Lux's development was the decision to pivot from a marketplace to a full-fledged brand. This shift was entirely consumer-driven, based on insights gathered from direct customer interactions.Fundraising Challenges: Natalie candidly discusses the journey of fundraising, particularly as a female founder. Despite the competitive landscape and systemic biases, she underscores the importance of perseverance and strategic financial planning.Brand Aesthetics and Market Trends: Natalie delves into the significance of aesthetics in the beauty industry. She describes Winky Lux's vibrant, art-inspired branding, which aligns with current market trends.Embracing Community and Collaboration: Natalie credits a considerable part of her success to the entrepreneurial community, highlighting how networks like YPO foster invaluable support and collaboration.Quote of the Show:“I don't mind swinging and striking out, but I really, really, really hate not having swung." - Natalie MackeyLinks:LinkedIn: https://www.linkedin.com/in/natalie-mackey-15169370/  Website: https://winkylux.com/  Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #WinkyLuxChapters:00:00 Intro01:23 Core Values and Company Culture at Winky Lux11:28 The Importance of Customer Feedback24:38 Challenges and Insights in Fundraising33:32 The High Stakes of Venture Capital35:06 The Changing Landscape of Entrepreneurship36:37 The Role and Structure of YPO40:00 Challenges and Resilience in Business45:03 Future Prospects for Winky Lux48:17 The Journey from Finance to Entrepreneurship51:27 Mentorship and Community Support59:11 Final Reflections and Advice1:00:55 Outro

What does it take to leave a high-profile role at Tesla and start your own electric vehicle company? In this episode, David talks with Toby Kraus, Co-Founder and CEO of Lightship, about his journey from working on Tesla’s Model S to building an innovative electric RV startup. Toby shares insights on taking big risks, scaling early teams, and navigating the challenges of a hardware business in the EV space. They dive into lessons learned at Tesla, the importance of building trust with investors, and the unique market opportunity Lightship is chasing. Takeaways:The Importance of Coaching: Toby emphasized the value of having a co-founder coach to strengthen the relationship between company leaders. He and his co-founder began working with a coach from the beginning, which Toby credits with helping them maintain a strong partnership and navigate the pressures of building Lightship.Adapting to Growth: As Lightship expanded, managing a larger team and aligning everyone with the company’s mission became a significant challenge. Toby learned that relinquishing control and trusting team experts were vital to maintaining momentum and effectiveness.Venture Capital Challenges: While their early seed round was successful, each subsequent round of funding became increasingly difficult, highlighting the unique challenges hardware companies face compared to software firms, as venture capitalists often favor faster software cycles.Creating a Culture of Ownership: Creating opportunities for team members to take ownership of projects fosters an environment of trust. By delegating responsibilities and empowering team members, leaders convey confidence in their team’s capabilities.Grateful of the Bumpy Path: Despite the mistakes and challenges he faced, Toby insists that changing any aspect of his journey might not have led to the founding of Lightship. Each experience, no matter how difficult, contributed to his current success and perspective.Quote of the Show:“My hidden agenda is I want to know why you wanna work here." - Toby KrausLinks:LinkedIn: https://www.linkedin.com/in/tobykraus/  Website: https://www.lightshiprv.com/  Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #LightshipChapters:00:00 Intro01:46 The Importance of a Co-Founder Coach02:28 Building a Strong Co-Founder Relationship07:15 The Tesla Connection14:38 Raising Capital During COVID16:20 Challenges of Hardware Startups24:00 Demonstrating Commercial Traction26:50 Sales and Marketing Strategy28:22 Hiring for Innovation30:05 The Importance of Interviewing Candidates30:39 Understanding the Common Failure Mode32:02 The Value of Authentic Motivation33:38 Emotional Runway vs. Cash Runway34:31 Challenges in Building Lightship37:38 Managing a Growing Team40:40 Relinquishing Control and Trusting Your Team44:00 Future Vision for Lightship50:03 Balancing Work and Family Life56:41 Reflecting on the Journey58:21 Outro

What does it take to drive significant transformation in a tech company? In this episode, David interviews Bryan Murphy, the seasoned entrepreneur and current CEO of Smartling. Murphy shares insights into his strategic decision to integrate AI rapidly at Smartling, the challenges faced in execution, and the creation of a separate R&D function to innovate without disrupting core operations. Murphy discusses his approach to leadership, the impact of meeting with hundreds of customers, and the critical role of operational discipline. Additionally, he reflects on his entrepreneurial journey, from his early ventures to his mentoring experiences and the factors driving his unyielding ambition.  Takeaways:Embracing Innovation and AI: Bryan emphasizes the importance of being early adopters of AI in order to remain competitive. He recounts how Smartling's leadership team proactively engaged with AI technologies as soon as they became available. Cultivating Customer Obsession: A significant part of Bryan's approach as CEO involves a deep focus on understanding and anticipating customer needs. He actively engages with customers, often initiating conversations with questions about the primary problems they are trying to solve.Building a Robust Operating Rhythm: Bryan highlights the critical role of a structured operating rhythm in executing plans effectively. Weekly leadership and management council meetings at Smartling help streamline processes and keep initiatives on track.Strategic Decision-Making in Remote Work Setup: With over 200 employees across 20 countries, Bryan holds annual gatherings and regular meet-ups to foster team cohesion while accommodating the global distribution of the workforce.Clarifying Business Metrics and KPIs: To Bryan, measuring success involves defining clear Key Performance Indicators (KPIs) that are aligned with customer value. These metrics directly inform product development and strategic priorities, ensuring the company remains focused on delivering value to customers.Overcoming the Innovator’s Dilemma: Bryan explains the challenge of balancing innovation with existing successful practices, a common issue known as the innovator's dilemma, by systematically integrating new technologies like AI to improve its service offerings without destabilizing its well-established operations.Advice for Aspiring Leaders: Bryan advises newcomers to the industry to always meet their obligations first and then seek opportunities to contribute more broadly, ensuring career advancement and sustained organizational impact.Quote of the Show:“[CEOs] have that latitude to run across the organization and dive down into each one of the respective parts of the organization, no one else can do that or does do that." - Bryan MurphyLinks:LinkedIn: https://www.linkedin.com/in/bryanmurphy2/Website: https://www.smartling.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #SmartlingChapters:00:00 Intro01:36 Embracing AI at Smartling02:43 Implementing AI in a Production Environment07:29 Customer-Centric Innovation11:01 Understanding Customer Needs24:25 Balancing Leadership and Involvement31:37 Weekly Operating Rhythm33:58 Strategic Planning and Key Initiatives35:43 Balancing Focus and Resources48:52 The Importance of Mentorship51:40 Reflecting on Entrepreneurial Journey54:06 Outro

What’s it really like to build a SaaS company from scratch, not just once but twice? In this episode, David talks to Thomas Pedersen, the serial entrepreneur who co-founded OneLogin and now leads Bunny, a bootstrapped billing platform for B2B SaaS.Thomas also opens up about co-founding two companies with his brother, surviving a major security breach, and how he’s approaching company-building differently this time around. Takeaways:Why Thomas Is Bootstrapping This Time: After raising $175 million for OneLogin, Thomas opted to bootstrap Bunny, focusing on control and long-term product quality. He discusses how this choice affects hiring, spending, and overall company culture.Bringing the Band Back Together: Bunny’s small but mighty team includes engineers from OneLogin. Thomas shares why working with trusted colleagues has helped them execute quickly and avoid early hiring pitfalls.The Grind Creates the Bond: Reflecting on the early OneLogin years, Thomas explains how hard work and shared struggle helped forge lasting relationships and why people often want to work with him again.Building with His Brother, Again: Thomas co-founded both of his startups with his brother. He explains how they complement each other technically, navigate disagreements, and have grown even closer through the experience.Remote from Day One: From commuting weekly between LA and San Francisco during OneLogin’s VC-fueled growth to now working from a boat in the Mediterranean, Thomas discusses why Bunny is remote-first and when in-person still matters.Lessons from a Security Breach: A major breach at OneLogin could have destroyed the company. Thomas details how transparency and direct communication with customers helped them retain trust and bounce back.Quote of the Show:"It’s really hard to get a design partner… I wish every Saas or every startup could find a customer like that." - Thomas PedersenLinks:LinkedIn: https://www.linkedin.com/in/tbpederWebsite: https://bunny.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #bunnyChapters:00:00 Intro01:32 Building Bunny: Lessons from OneLogin02:39 Team Dynamics and Hiring Strategies05:59 Working with Family: A Brother's Partnership10:55 Remote Work and Company Culture16:40 Bootstrapping vs. Venture Capital23:37 Marketing and Personal Branding28:46 Passion for Solving Business Problems31:21 The Importance of Solving Business Problems31:38 Challenges and Solutions in Billing33:24 Early Days of OneLogin33:40 Building SAML Integrations36:20 Acquiring First Customers for Bunny37:35 The Role of Design Partners41:28 Handling Security Breaches45:04 Transparency and Customer Trust48:09 Future of Bunny50:46 Entrepreneurial Journey and Background54:45 Mentorship59:13 Advice to His Younger Self01:03:04 Outro

Do you know the key factors for successful leadership in high growth tech companies? In this episode, CEO of commercetools Andrew Burton shares his extensive experience in building and scaling tech companies. With over 25 years in the industry, Burton details his approach to leadership since becoming CEO of commercetools in 2024. He emphasizes the paramount importance of maintaining customer focus, building strong team culture, and aligning company goals.  Takeaways:Understanding Customer Needs: Andrew highlights the importance of stepping into customers' shoes to understand their challenges and measure success through their lens. He emphasizes starting conversations by asking customers about their challenges and how they define success.Aligning Around an Ideal Customer Profile: A crucial step Andrew implemented at commercetools was refining their Ideal Customer Profile (ICP). He stresses the necessity of focusing on where the company can deliver the most significant value and understanding why they're uniquely positioned to serve that particular segment.The Role of Leadership in Team Development: Andrew believes in playing as one team and ensuring a unified direction across the organization. He discusses the importance of testing for cultural and operational inconsistencies as a new CEO and aligning the team around shared objectives and metrics. Strategic Planning and Adapting to Change: Andrew shares insights into effective strategic planning by decoupling it from the stress of annual closing and starting a new fiscal year.Curiosity as a Driver for Success: Andrew describes how a curious approach to understanding problems and developing solutions leads to personal and organizational growth, making it a critical quality he looks for when hiring team members.Balancing Passion and Work-Life Integration: Andrew touches on the concept of work-life balance, suggesting that it is deeply connected to one's passion and motivation. He encourages individuals to be mindful of what genuinely drives them and to regularly assess whether their professional and personal lives are aligned with these motivations.Mentorship and Learning from Diverse Experiences: Andrew reflects on his journey and the importance of mentorship, emphasizing that learning from a variety of experiences and colleagues, regardless of hierarchy, contributes to a well-rounded leadership style.Quote of the Show:"Anybody that's really, I would argue successful… in their space, is going to know or have an appreciation for, at the core, the customer." - Andrew BurtonLinks:LinkedIn: https://www.linkedin.com/in/burtonandrew/Website: https://commercetools.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #commercetoolsChapters:00:00 Intro01:58 The Importance of Customer-Centric Leadership04:21 Engaging with Customers: Strategies and Insights09:36 Aligning Company Mission and Team Goals13:10 Defining the Ideal Customer Profile (ICP)17:50 Building Trust and Credibility as a New CEO23:15 Strategic Planning and Measuring Success31:50 Monthly Cadence and Operational Efficiency33:05 Reflections on Planning and Offsite Meetings34:50 Journey to Becoming a CEO35:58 Curiosity and Leadership43:44 Mentorship and Influences46:24 Hiring and Growth Mindset51:43 Future of Commerce Tools53:36 Personal Background and Motivation56:59 Work-Life Balance and Career Advice01:01:48 Outro

What happens when you commit to shipping a podcast episode every week for an entire year? In this solo episode, David Politis reflects on 12 months of building Not Another CEO Podcast, from humble beginnings to an ever-growing audience of Founders, CEOs, and leaders. David shares 10 of his favorite highlights from the journey so far, covering everything from guest stories and personal milestones to the behind-the-scenes evolution of the show. This episode is a heartfelt thank-you to the community that has grown around the podcast and a look ahead at what’s next. Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/#NotAnotherCEO #Podcast #1YearReflection

What does it take to transform a scrappy logistics startup into a leading supply chain platform trusted by Fortune 500 brands? In this episode, Sean Henry shares the story of founding Stord, dropping out of college to build it, and scaling a distributed logistics network from zero to national reach. He opens up about fundraising setbacks, building conviction in tough moments, keeping customer experience front and center, and navigating the pressure of rapid growth while staying anchored in purpose. Takeaways:Dropping Out to Go All-In: Sean left college to pursue Stord full time, driven by a conviction that there was a better way to manage logistics in a fragmented industry. That early decision required grit and belief before traction or investor backing.Turning Cold Outreach Into Capital: Sean shares how his early fundraising relied on writing 150 cold emails a day. Persistence and storytelling helped him break through, eventually leading to key early checks that helped kickstart Stord’s growth.The Importance of Mission and Mindset: Through tough moments and early challenges, Sean and his Co-Founder stayed grounded in their mission. He talks about the psychological weight of leadership and the discipline required to keep moving forward.From Scrappy Marketplace to Full Stack Platform: Stord started as a logistics marketplace but pivoted into a fully integrated supply chain solution. Sean explains how that shift allowed them to deliver better customer experience, tighter control, and long-term defensibility.Customer Experience Is the Product: Even as a logistics company, Sean believes customer experience is the most important differentiator. He shares how Stord built systems and culture that put CX at the center of every part of the business.Navigating the Growth Curve Without Losing Focus: Sean discusses what it’s like to scale quickly while holding on to high standards. He shares lessons around team building, leadership habits, and making time for clarity amid the noise.Believe, But Be Realistic: Sean reflects on the importance of conviction, but also warns Founders to avoid believing their own hype. He recommends surrounding yourself with people who keep you honest and grounded as you grow.Quote of the Show:"If we don't have a customer, we don't have employees. If we have a vision but have no customers, that vision means nothing." - Sean HenryLinks:LinkedIn: https://www.linkedin.com/in/shenry96/Website: https://www.stord.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #StordChapters:00:00 Intro01:49 The Importance of Customer Obsession05:44 Hiring for Customer Obsession10:19 Scaling and Company Culture21:30 Early Challenges and Pivots39:26 The Rise and Fall of the Trucking Network40:23 Navigating Hard Decisions and Growth42:50 Investor Relations and Fundraising Journey44:11 Mentorship and Early Influences45:33 Strategic Partnerships and Business Alignment51:23 Overcoming Challenges and Turning Points56:10 Future Vision and Expansion Plans01:03:51 Personal Background and Entrepreneurial Spirit01:13:14 Advice to His Younger Self1:14:40 Outro

What can you learn from someone who built and sold multiple enterprise startups, led teams through acquisitions, and now mentors the next generation of Founders? In this episode, Ellen Rubin shares lessons from her journey as a serial Founder and now Operating Partner at Glasswing Ventures. She talks about building strong cultures, nurturing early career talent, supporting women in tech, and helping startups avoid hype in favor of real-world value. From lunch-and-learns to boardroom decisions, Ellen reflects on what it takes to grow people and companies with clarity and purpose. Takeaways:How to Spot Future Founders Inside Your Company: By encouraging curiosity and inviting team members into strategic conversations, Ellen helped cultivate talent that would eventually become leaders. She looked for people who asked questions, engaged outside their lane, and showed deep interest in how the business works.Practical Support for Women in Tech: Ellen shares her multi-layered approach to supporting women in technology. She has a personal policy of responding to every outreach from a woman Founder or aspiring leader, offering both encouragement and actionable help.Building Strong Local Ecosystems: As a passionate advocate for Boston’s tech scene, Ellen emphasizes the importance of keeping post-exit Founders and big companies engaged with the next generation. She believes physical proximity and local mentorship still matter, even in a hybrid work world.The Value of Regular All-Hands and Real Transparency: At her startups, Ellen hosted weekly all-hands to build alignment and trust. She prioritized consistent updates, company-wide visibility into fundraising stages, and direct Q&A with leadership to keep teams connected and focused.Lessons from Amazon and the PR/FAQ Method: Ellen talks about her time at Amazon and how the press release and FAQ approach to product planning shaped her thinking. She encourages Founders to use writing and storytelling as a way to clarify product vision before building anything.AI That Solves Real Problems: Now an Operating Partner at Glasswing Ventures, Ellen focuses on “intelligent verticals” that use AI to automate industry-specific workflows. She emphasizes the importance of AI being integral to the product, not just a wrapper for marketing.Quote of the Show:"Why wouldn't you wanna be the Founder CEO? That's like the coolest thing in the whole world." - Ellen RubinLinks:LinkedIn: https://www.linkedin.com/in/ellenrubin/Website: https://glasswing.vc/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #CauselyChapters:00:00 Intro01:45 Key to Startup Success: Building the Right Team03:08 Exposing Team Members to the Bigger Picture06:08 Encouraging Curiosity and Engagement09:45 Supporting Women in Technology15:03 Challenges in the Tech Industry17:50 The Boston Tech Ecosystem21:37 Importance of Local Community in Remote Work Era27:08 Customer Engagement and Feedback30:07 Effective Operating Rhythms35:23 Lessons from Amazon37:50 Navigating the M&A Process38:31 Deciding the Right Time to Sell40:59 Taking Calls from Corporate Development44:30 The AI Revolution: A 70-Year Overnight Sensation46:00 The Role of AI in Modern Enterprises01:01:58 The Importance of Mentorship01:06:25 Balancing Entrepreneurship and Family01:09:13 Advice for Aspiring Entrepreneurs1:10:27 Outro

What happens when you try to fund and scale a legal tech company in one of the most rigidly regulated industries in the country? In this episode, Todd Richheimer shares how he grew Lawfty into a tech-powered personal injury platform that has generated over 55,000 cases and nearly a billion dollars in recoveries.From taking his first client calls on his cell phone to surviving a last-minute funding failure, Todd speaks openly about scaling, leadership evolution, and what the legal world looks like as regulation and AI collide. Takeaways:Finding the Right Co-Founder in the Hamptons: Todd met his Co-Founder, a former MIT engineer, in the Hamptons. They spent a year working on ideas every Saturday before launching Lawfty, combining Todd’s legal background with Mike’s technical skills.Building with Complementary Strengths: Todd surrounded himself with people who could help him see around corners. He emphasizes that knowing your weaknesses and recruiting to fill them is the most impactful thing he's done as a Founder.The Power of Shameless Outreach: Todd started the company by emailing every contact in his Gmail account. With no product and no revenue, he relied on personal relationships and a willingness to ask for help to land early clients and supporters.Leading with Empathy and Integrity: Todd acknowledges his struggle with letting underperforming team members go, especially when they're good people. Instead of defaulting to layoffs, he focuses on reshuffling and preserving relationships where possible.From Answering Phones to Scaling Teams: For over a year, Todd personally fielded every intake call. That hands-on experience shaped how he hires and builds processes today, and made him intimately familiar with every part of the business.Navigating Capital Constraints Without Venture Money: Due to legal restrictions, Lawfty couldn’t raise institutional equity. Todd had to get creative with structured finance, high-interest loans from individuals, and careful debt planning to scale the company.Legal Tech’s Big Bang Moment: Todd sees the convergence of AI and regulatory change as a generational opportunity for the legal industry. With non-lawyers now allowed to own law firms in more jurisdictions, he believes the space is finally ripe for innovation and scale.Quote of the Show:"Standing up for individuals always felt right to me… so I didn’t necessarily care about the personal view that people had." - Todd RichheimerLinks:LinkedIn: https://www.linkedin.com/in/todd-richheimer-esq/Website: https://www.lawfty.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #LawftyChapters:00:00 Intro01:41 The Importance of Complementary Skill Sets02:41 Finding a Co-Founder in an Unlikely Place03:44 Building Lawfty: From Idea to Execution06:19 Challenges and Strategies in Team Building09:29 Navigating the Interview Process12:47 Understanding Lawfty’s Business Model16:26 Early Customer Acquisition Tactics20:57 Fundraising Journey and Lessons Learned26:38 Scaling as a CEO29:31 The Legal Tech Revolution32:09 Challenges in Legal Services34:52 Building a Tech-Enabled Law Firm37:14 Overcoming Industry Stigma42:35 Fundraising Challenges and Solutions47:01 Personal Journey and Entrepreneurial Drive54:12 Advice for Aspiring Entrepreneurs56:48 Outro

What does it take to lead a global humanitarian organization through a pandemic and beyond? In this episode, Michael Nyenhuis shares how he has led UNICEF USA since March 2020, starting his role just two weeks after COVID shutdowns began. Michael talks about building strong boards and leadership teams, the balance between confidence and humility, and how to create connection in a hybrid work world. With decades of experience in humanitarian leadership, he reflects on his journey from journalist to President & CEO, and how staying close to mission and people shapes lasting impact.Find Michael's Newsletter here: https://www.linkedin.com/newsletters/relentless-6990692731056488449/ Takeaways:Rebuilding the Board and Leadership Team: Michael explains how reshaping governance and leadership early in his tenure has been crucial to the success of every organization he has led. He emphasizes getting the right people in place who share the mission and bring diverse skills and chemistry to the table.Evolution Over Revolution: Describing his leadership approach, Michael shares his belief in "relentless incrementalism." He believes consistent, thoughtful progress is more sustainable than sweeping change and that small steps taken regularly are key to building lasting impact.Starting a CEO Role in a Global Pandemic: Michael began his job just as COVID shut the world down. He relied on daily video updates, creative communication, and a golden retriever named Izzy to build relationships remotely. He reflects on the benefits and drawbacks of trying to lead without in-person interaction.Creating Culture in a Hybrid Workplace: UNICEF USA has embraced hybrid work, but Michael is intentional about maintaining connection. From monthly staff engagement days to leadership meetings and all-staff retreats, he builds structured moments for human interaction and relationship-building.Honest Career Advice for Aspiring Humanitarians: Michael stresses that global development is a profession, not just a passion. He shares how expertise, formal experience, and training are key to entering the nonprofit space and why it is important to respect the rigor of humanitarian work.CEO Roundtables and Mentorship by Listening: Michael hosts monthly roundtables with staff based on anniversary dates, offering space for Q&A and storytelling. He also invited youth leaders to mentor him, flipping the script to show respect and learn from the next generation of changemakers.Balancing Confidence and Humility: Michael reflects on the need to balance strong leadership with the humility to listen. Early in his career, he sometimes over-relied on consensus. Today, he sees the value in trusting instincts while remaining open.Quote of the Show:"When you find what you're supposed to do, doors start opening." - Michael NyenhuisLinks:LinkedIn: https://www.linkedin.com/in/michaelnyenhuis/Website: https://www.unicefusa.org/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #UNICEFUSAChapters:00:00 Intro01:28 Key Achievements at UNICEF USA03:18 Building Effective Leadership Teams14:13 Navigating Challenges During the Pandemic20:14 Remote and Hybrid Work Dynamics29:31 CEO Round Table and Onboarding30:48 Operating Rhythm and Annual Planning32:18 Monthly Staff Meetings and Engagement36:22 Public Speaking and Media Training39:55 Managing Diverse Constituents42:36 Biggest Challenge: Leading Through COVID-1945:16 Career Journey and Journalism Background51:47 Mentorship and Youth Engagement54:32 Balancing Confidence and Humility in Leadership58:03 Outro

What does it take to walk away from a big idea and start over inside the same company? In this episode of Not Another CEO Podcast, Adam Dell opens up about the journey behind Domain Money. A serial Founder with multiple exits, Adam reflects on making hard pivots, recruiting top talent personally, navigating investor psychology, and why execution, not ego, is what earns the right to exist. He also shares how AI is transforming financial services and why the emotional highs and lows of startup life never really go away. Takeaways:Recruiting Personally, Relentlessly: Adam still personally recruits on LinkedIn, often spending hours each day identifying talent, crafting outreach, and filtering for startup fit. He believes CEO-led recruiting cuts through noise and shows prospects the role's importance.A Pivot Before the Crash: Originally conceived as a crypto banking platform, Domain Money pivoted early. Adam made the call based on market fundamentals and moved decisively, even when his team was still optimistic about the original vision.Transparent, Yet Optimistic Leadership: During the pivot, Adam prioritized honesty with his team while maintaining belief in the mission. He communicated openly about uncertainty and made clear that success was entirely on them.Investor Support Built on Track Record and Clarity: Adam credits his investor relationships and clear, data-backed thinking for enabling a smooth pivot. Though they challenged him, his investors supported the shift and recognized the market opportunity in personal finance.AI as a Backbone, Not a Gimmick: AI plays a major role in Domain Money’s operations, especially in improving planning efficiency. Adam is enthusiastic about AI’s pace and scope of change, calling it central to his product vision.The Mental Game of Being a Founder: The pivot at Domain Money required layoffs and letting go of certainty. Adam talks candidly about staying objective under pressure, fighting through doubt, and surrounding himself with trusted mentors while still waking up every day to earn it.Quote of the Show:"That uncertainty, that thing inside of you that forces you to figure it out, is very motivating to me and I quite enjoy it." - Adam DellLinks:LinkedIn: https://www.linkedin.com/in/adamdell/Website: https://www.domainmoney.com/Ways to Tune In:Substack: https://notanotherceo.substack.com/Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 YouTube: https://www.youtube.com/@NotAnotherCEOPodcast Transistor: https://podcast.notanotherceo.com/ #NotAnotherCEO #BusinessSuccess #DomainMoneyChapters:00:00 Intro01:25 Recruiting Strategies for Startups07:15 Fundraising Insights and Market Sentiment11:46 The Evolution of Domain Money16:25 Navigating Pivots and Team Buy-In23:07 Growth Strategies and Partnerships26:20 Acquisitions and Exits29:23 Strategic Partnerships and Revenue Growth30:37 The Impact of AI on Technology and Business35:12 AI in Financial Planning and Wealth Management39:51 Challenges and Pivots in Business49:09 Personal Background and Entrepreneurial Journey57:37 Advice for Aspiring Entrepreneurs01:00:30 Outro