High Stakes

In this episode of High Stakes, Paige Soya sits down with Dadi Akhavan, a startup-to-IPO founder and angel investor, to break down one of the most important dynamics in early-stage investing: angel investors vs venture capitalists.While both play critical roles in the startup ecosystem, the way they invest and what they need from their investments iis fundamentally different.We explore how those differences shape everything from deal selection to decision-making to founder outcomes.Key themes include:Why venture capital funds are structurally driven to pursue “outlier” returnsHow fund size, LP expectations, and mandates influence VC behaviorWhy angel investors have more flexibility in what and when they investHow early-stage founders should think about which type of capital to raise — and whenThe tradeoffs between taking institutional money vs. staying in the angel ecosystemWhat “stage of company” really means in practice for fundraising strategyHow experienced investors evaluate opportunity differently based on structure, not just preferenceDadi also shares insights from his own journey, from building companies to taking one from startup all the way to IPO, and how that experience shapes his approach to investing today.This episode is a deep dive into the mechanics behind startup funding decisions, and what founders often overlook when choosing between angels and VCs.

How do venture capitalists actually find deals and how can founders break into those conversations? In this episode of High Stakes, Paige Soya and Nick Duafala are joined by Taylor Margot (Partner at Lytical Ventures) to break down one of the most important, and often misunderstood, parts of venture capital: deal sourcing. They unpack where deals really come from, from warm referrals and deep networks to unexpected moments of curiosity, and why the strongest opportunities are often driven by relationships, not cold outreach. The conversation goes beyond surface-level advice to explore how sourcing has evolved, the role of personal brand, and why depth matters more than breadth in today’s market. For founders, this episode is a playbook. The group shares practical strategies for getting in front of VCs, from leveraging your network the right way to standing out at events, and what not to do if you want to build lasting investor relationships. They also dive into the psychology behind cold outreach, why most inbound gets ignored, and how to increase your odds of getting that first meeting. Whether you're an investor looking to build deal flow or a founder trying to raise capital, this episode offers a clear, tactical look at how connections actually turn into deals and how to position yourself on the right side of that equation. What you’ll learn: -How VCs really source deals (and why it’s not just about “who you know”) -The difference between warm intros, cold outreach, and organic discovery -Why deep relationships outperform wide networks -How founders can effectively get in front of investors -The biggest mistakes founders make when approaching VCs -Why venture is a long game—and how to play it

Venture capital is one of the most misunderstood asset classes in investing and one of the most powerful when approached correctly.In this episode of High Stakes, K Street Capital Managing Partner Paige Soya sits down with investor Jill Ralph (Motley Fool’s former President of Global Membership, and former VP of Chemonics Capital) to break down Venture Capital 101, from both the investor and founder perspective.They unpack what venture capital actually is, how it fits into the broader investing landscape, and why it operates so differently from traditional asset classes like public equities. From risk and liquidity to diversification and portfolio strategy, this conversation covers the fundamentals every new investor should understand before entering the space.But this episode isn’t just for investors. For founders, Paige and Jill dive into a critical question: Is your company even a fit for venture capital? They explore what types of businesses are best suited for VC, what taking on venture funding really means for your company’s future, and how it can fundamentally shape your growth trajectory.They also cover:Why venture capital is considered one of the highest-risk asset classesWhat diversification looks like in a venture portfolioHow long it typically takes to see returnsWhat it means to be an accredited investor and how much capital you need to get startedHow venture-backed companies differ from traditional businessesWhether you’re an aspiring investor looking to break into venture or a founder evaluating funding options, this episode provides a clear, foundational understanding of the risks, rewards, and realities of venture capital.Because while venture is high risk and long-term, it also offers something unique: the opportunity to back innovation early and watch it grow from the ground up.

Welcome to Season 4 of High Stakes and this season we’re starting with the fundamentals.In Venture Capital 101, K Street Capital Managing Partner Paige Soya and Principal Nick Duafala break down how venture capital actually works for founders, investors, and anyone curious about the startup ecosystem.In this opening episode, Paige and Nick share the origin story of K Street Capital and their own paths into venture, from Wall Street and investment banking to founding and exiting a fintech company.They discuss:How K Street Capital started as an angel syndicate and evolved into a venture platformWhy early-stage investing is different from traditional financeWhat makes venture capital unique compared to other asset classesHow investors evaluate startups and work alongside foundersAlong the way, they also talk about some of the companies K Street has backed, from digital health platforms to AI-powered robotics, and what makes those opportunities exciting.This episode sets the stage for the rest of the season, where Paige and Nick will walk through the full venture capital playbook, including angel investing vs. VC, startup evaluation, deal terms, portfolio strategy, and more.If you're a founder thinking about raising capital, an investor interested in venture, or just curious about how the startup funding world works, this season is designed to be your starting point.Listen to the full episode and follow along as we break down Venture Capital 101.

In this episode of High Stakes, host Paige Soya, Managing Partner at K Street Capital, sits down with Julie Castro Abrams, GP and Founder of How Women Invest, for a candid look at one of the most important shifts happening in venture capital today: the surge of women stepping in as LPs, angel investors, and fund leaders.Just over a decade ago, there were only 12 women-run funds. Today, there are more than 380. We are in a watershed moment—one filled with opportunity, friction, and long-overdue change. Julie breaks down not just why this moment is happening, but what’s still holding women back from fully participating in the ecosystem.Together, Paige and Julie uncover the lived experiences, expertise, and decision-making strengths that women bring to venture—and the systemic obstacles that still stand in their way, from misaligned financial advisor incentives to outdated assumptions about risk, time, and wealth.Whether you’re a GP, an operator thinking about becoming an LP, or simply curious about how capital flows and who gets to shape innovation, this episode is packed with insights you won’t want to miss.In This Episode, We Cover:The Real Barriers Keeping Women from InvestingWhy the biggest limitations aren’t ability or interest, but access, time, exposure, and frictionHow financial advisors, often unknowingly, disincentivize clients from exploring alternative investments like VCWhy the question “Do you personally invest in venture?” can reveal critical advisor blind spotsHow inherited wealth, fear, lack of exposure, and over-reliance on traditional systems impact women differently

In this episode of High Stakes, K Street Capital Managing Partner, Paige Soya, sits down with Gabriel Jarrosson, Managing Partner at Lobster Capital, to unpack how Y Combinator’s internal tool “Bookface” is reshaping investor-founder relationships in 2025.YC’s Bookface allows founders to rate their experiences with investors — creating a private reputation system that influences who founders choose to work with in the future. The result? A new era where investor behavior, transparency, and credibility matter just as much as capital.💡 In this episode:How YC’s Bookface works behind the scenesWhat investor ratings mean for fundraising strategyWhy reputation has become a competitive advantage for VCs and angelsHow this shift is redefining accountability in venture capitalWatch now to learn how your reputation has become your strategy in the evolving world of startup investing.

The High-Stakes Decisions Behind Early Fundraising: When to Raise, Who to Raise From, and How Much Equity to Give UpIn this episode of High Stakes, host Paige Soya sits down with Jennifer Neundorfer, Managing Partner at January Ventures, for a candid conversation about the early fundraising decisions that can make or break a startup’s future.Together, they dig into the nuances of when to raise capital, who to take money from, and how much equity to give away and the ripple effects those choices have on company trajectory, investor fit, and founder control.From bootstrapping to pre-seed, Jen and Paige share real examples of companies that got these calls right and others that didn’t - plus actionable guidance for founders navigating their first round.What You’ll Learn:When to raise: How to know if you’re truly ready for outside capital and why raising too early can hurt more than help.Who to raise from: The dangers of taking the wrong investor money and how to identify the right venture partners for your business.How much to raise (and give up): Why founders should aim to give up no more than 25% early on, and how multiple small rounds can quietly cause major dilution.Real-world examples: What happens when pre-seed investors impose “weird” terms and how it can stall future fundraising.Investor perspective: What makes a company uninvestible from a venture firm’s point of view.

Many investors still see backing diverse founders as a bigger risk.In this episode of High Stakes, Paige Soya sits down with Melissa Bradley, General Partner at BAE Ventures, to challenge that misconception and explore why portfolio diversity can actually fuel stronger returns.Melissa shares her experience investing across sectors, from tech to CPG, and how diversity isn’t just about representation, it's about building companies that understand different customers, markets, and opportunities.Watch the full episode for a deeper dive into how diversity drives returns.

How do investors evaluate founders when there’s little or no traction? What really drives decisions in early-stage venture capital?In this episode of High Stakes, host Paige Soya sits down with early-stage investor Matt Gittleman to unpack the art and science of diligence. From scorecards and rubrics to founder storytelling and grit, Paige and Matt explore why rigid frameworks can fall short and how experienced investors read between the lines.You’ll learn:Why scorecards and rubrics can be gamed (and what to use instead)Matt’s “levers and hurdles” approach to evaluating startupsHow speed, style, and grit signal founder potentialWhy the way a founder articulates their vision can matter more than the metricsThe limits of AI in a process that’s deeply qualitative and human-drivenWhether you’re a founder preparing to fundraise or an investor refining your own diligence process, this conversation offers a candid look into how early-stage deals really get done.

How do you know if you're actually a successful venture capitalist? It's harder to tell than you might think. In this episode, K Street Capital Managing Partner Paige Soya sits down with Henri Pierre-Jacques, Managing Partner of Harlem Capital, to dive deep into the metrics that really matter in venture capital - and why most of them have nothing to do with spreadsheets.Henri shares the brutal realities of fund performance, including why only 16% of funds make it to Fund IV and how the 2021 vintage created one of the tightest performance bands in 20 years. But beyond the financial metrics like TVPI and DPI, we explore the operational indicators that successful VCs track daily: graduation rates, win ratios, cash efficiency, and the often-overlooked importance of deal access and founder relationships.

Most founders know the pressure of fundraising, but what many don’t realize is that venture capitalists have to fundraise too. Behind every investment is a group of limited partners (LPs) whose expectations shape how funds operate, the kinds of companies they back, and even the way they communicate with founders.In this episode of High Stakes, host Paige Soya (Managing Partner, K Street Capital) sits down with Nasir Qadree, Founder and Managing Partner of Zeal Capital Partners, to explore what LPs really want from VC fund managers and why it matters.They cover:What LPs look for when deciding whether to re-up with a fundWhy many institutional investors are leaning into emerging managersHow individual LPs think about risk, liquidity, and the “long game” of ventureThe difference between being an investor and being a fund managerWhy strong communication, transparency, and firm-building matter just as much as returnsNasir also shares lessons from raising Zeal Fund II, the importance of aligning with LPs beyond capital, and why DC is uniquely positioned to create category-defining companies.If you’ve ever wondered how LP priorities shape the venture ecosystem (and ultimately, what gets funded), this episode offers a candid inside look.

What makes a venture investment a true home run—and why is it so hard to find those opportunities?In this episode of High Stakes, Paige sits down with Sean Glass (entrepreneur, investor, and founding partner at Ayuda Partners) to unpack the mechanics of venture capital decision-making. Together, they explore:Why venture returns rely on power-law outcomesThe importance of market size and market dynamics when evaluating startupsThe pitfalls of messy cap tables, notes, and SAFEs and how they can derail a dealSean also shares insights from his own entrepreneurial journey, including raising capital in tough markets, achieving outsized returns for early investors, and building conviction around companies that can define entirely new categories.Whether you’re a founder raising capital, an investor honing your thesis, or just curious about how VCs make high-stakes decisions, this conversation is packed with hard-won lessons from both sides of the table.

“The Ownership Equation: Why Check Size, Stage, and Strategy Matter in VC”What does a $2M check actually mean for the founder, the investor, and the future of the company?In this episode of High Stakes, Paige Soya sits down with Michael Bosch to unpack the mechanics behind venture capital that most founders and even some investors get wrong. From rigid ownership targets to flexible fund strategies, and from GenAI-fueled capital efficiency to cap table waterfall risks, this conversation gets into the tactical realities behind early-stage funding.You’ll learn:Why check size, ownership percentage, and stage must be alignedHow generative AI is reshaping team size, round size, and outcomesWhat investors really mean when they say they need 10%Why early investors can get wiped out even when a company winsIf you're a founder raising capital or an investor navigating the new VC landscape, this episode breaks down what really matters and what’s changing fast.

At K Street, we’ve had the privilege of backing some incredible founders and over time, one theme has become increasingly clear: The most impactful leaders aren’t just building great companies, they’re also investing in others. These are dual threat CEOs: founders who play both offense and defense. They're scaling their own ventures while also writing early checks, mentoring rising entrepreneurs, and giving back to the ecosystem that helped them succeed. In the latest episode of High Stakes, K Street investor Sara Fagen joined Paige Soya to unpack what that role really looks like and why it matters. She shared a powerful perspective on how investing can be a vehicle for impact especially for new founders who have big ideas but lack access or experience. These early-stage bets often start with a conversation, a relationship, and a belief that someone just needs their first chance. That’s the ethos we carry at K Street. We back operators who pay it forward and we’re proud to count so many dual threat CEOs in our portfolio and community.

Ever wonder why venture capitalists fight for board seats? It's not just about control or fancy dinners. In this episode, Paige Soya (Managing Partner, K Street Capital) sits down with Brian Goldsmith (Managing Partner, Avenue Growth Partners) to pull back the curtain on board governance in venture capital.In this episode, they cover the real work behind board seats, share war stories from boardrooms and explain why the right board can literally save companies from bankruptcy.Moving beyond the quarterly meeting stereotype, Paige and Brian dive into the substantial work that happens between board meetings. They discuss how effective board members provide ongoing strategic support, help founders navigate cash flow crises before they become critical, and serve as trusted advisors during the inevitable ups and downs of startup life. The conversation explores the real motivations behind VC board seat requirements, moving beyond simple control narratives. Brian explains how board seats enable better value creation through ongoing visibility and trust-building. He also discusses how they provide necessary governance rights to protect LP interests. They discuss the delicate balance between serving as a fiduciary to the fund while remaining a supportive partner to founders, especially when these interests might appear to conflict.

There’s a lot to love about working in venture capital but there’s also a lot of hard, often overlooked work that doesn’t make the headlines. In this debut episode of High Stakes, Paige Soya, Managing Partner at K Street Capital, sits down with James Barila, Former Revolution VC investor, now Executive Director at Station DC, for a candid conversation about the realities of running a venture fund – beyond sourcing deals. They unpack the not-so-glamorous core responsibilities of a VC that don’t get the headlines they deserve but keep a firm alive.  The episode also explores why emerging managers need to be setting up a DC ground game strategy early. For founders in tech and innovation-driven sectors, engaging with the Washington ecosystem is not optional. Proximity, presence, and participation can be the difference between momentum and missed opportunities. Whether you're an emerging manager, a founder navigating policy, or an LP curious about what happens behind the scenes, this episode offers a clear-eyed look at the unglamorous – but essential – side of venture.

What separates successful founders from the rest?In this episode of High Stakes, Paige Soya (Managing Partner, K Street Capital) sits down with Alex Wirth, CEO & Co-founder of Quorum, to unpack the habits, mindsets, and leadership lessons that helped him scale his company from 2 founders to 300+ employees over 10 years.Key takeaways: ✅ How to build the right team at every stage of growth ✅ When founders need to evolve their leadership style ✅ The role of mindset and resilience in navigating startup highs & lows ✅ Lessons on scaling without overextending your cash flowWhether you’re a VC or an operator, this conversation is packed with timeless advice.

In this episode of High Stakes, host Paige Soya sits down with Myrto Lalacos, Principal at VC Lab, for an in-depth conversation on landing a job in VC. Myrto shares her unique career journey—from leading accelerator programs in the UK to co-founding a B2B SaaS fund and launching the Venture Institute, an initiative aimed at connecting diverse, emerging talent with pathways into VC. Together, Paige and Myrto explore what it really takes to be a fund manager, and the often-overlooked skills critical to running a venture firm—not just sourcing deals.What You'll Learn in This Episode:● How Venture Institute is reshaping VC education to cultivate tomorrow’s top investors● Why deep roots in the startup ecosystem aren't just helpful—they’re your unfair advantage● Myrto’s bold leap from accelerator programs to deploying capital● The incredible story of a candidate who coded their way into a VC role● What sets Venture Institute’s analyst training apart● The fundraising muscle every fund manager must buildWhether you’re an aspiring investor, curious about breaking into VC, or want to understand how new funds are formed, this episode is packed with real world insights and inspiration.#startups #venturecapital #careerventurecapitalist #VC #VCLab

What really happens when a startup shuts down? In this revealing episode of High Stakes, host Paige Soya sits down with Dori Yona, founder of SimpleClosure and seasoned entrepreneur, to unpack the complex—and often hidden—realities of shutting down a startup. After navigating the painful process of closing his own VC-backed company, Dori realized just how broken and opaque the process was, and became determined to fix it. Now, after guiding over 500 shutdowns in 2024 alone, he brings clarity to a topic most founders and investors would rather avoid. From legal minefields and IP entanglements to payroll risks and emotional tolls, Dori shares what every stakeholder needs to know about ending a startup the right way.Key Points From This Episode:How Dori’s own shutdown journey inspired the creation of SimpleClosureHidden liabilities and risks founders and VCs often missWhat happens to intellectual property, equity, and employee obligationsData from 2023–2024: which startups are shutting down, where, and whyThe surprising prevalence of founder-led shutdownsVisa challenges for international founders during closuresHow SimpleClosure streamlines the wind-down processThe role of VCs in helping founders exit cleanly and move forwardWhether you’re a founder, operator, or investor, this episode is a must-listen for understanding the realities of startup shutdowns—and how to navigate them with integrity.

Not every startup story ends in a big exit. Sometimes, despite best efforts, companies miss key milestones, burn through their runway, or become what investors call “zombie startups.”In this episode of High Stakes, host Paige Soya sits down with Tony Chan, partner at ORIC and seasoned venture capital and M&A expert, to explore the hard truths of venture investing. Tony shares insights into what happens when deals go south—and what investors can (and should) do when startups are struggling.Key Points From This Episode:• Common examples of how companies can handle early closures and exits.• The importance of early, honest conversations when things aren’t going to plan.• Why founder optimism and investor caution can be hard to reconcile.• Founder trust in VCs: how it hinges on operating experience and credibility.• Navigating misaligned incentives among early and late-stage investors.• What really happens behind the scenes before and after a board meeting.• How disciplined investors avoid FOMO and spot underfunded opportunities.• Why some startups are turning to even-sided mergers instead of IPOs.• The growing role of secondaries in private market liquidity.• How VC is shifting as private equity becomes more accessible to retail investors.

Why do some VCs lead while others follow? On this episode of High Stakes, host Paige Soya sits down with Mark Volchek, founding partner at Las Olas Venture Capital, to explore the dynamics of leading versus following in venture capital. With a focus on early-stage B2B software, Mark brings insights from his journey, from founding a FinTech company during the dot-com crash to launching and managing multiple successful funds since 2016. Together, they unpack the pros and cons of leading investment rounds, how firm size and resources influence strategy, and how to navigate key decisions like taking board seats, aligning with co-investors, and allocating resources. Mark also shares advice for founders on finding the right VC fit and explains why there is a firm out there for every type of startup. Tune in for a deep dive into how venture firms decide when to lead and when to follow, and what that means for investors and founders alike!Key Points From This Episode:• Mark’s journey from entrepreneurship to venture capitalism.• Lessons from being an angel investor and limited partner (LP).• The value of being on the board of companies you’ve invested in.• Key advantages and challenges of leading investments.• How to take the size and resources of your VC firm into account.• The difficulties of following on in oversubscribed rounds.• Unpacking the necessity of aligning with co-investors.• Mark’s advice to founders on how to find the right VC fit for your company.

How do you make it in venture capital when the path is anything but straightforward? In this episode of High Stakes, Ethan Austin, Founding Partner at Outside VC, shares his journey and the key lessons he's learned as a founder in the world of early-stage investing. From the importance of empathy and people skills over traditional finance experience to the power of networking and taking bold, unconventional actions to set yourself apart, Ethan breaks down what it takes to succeed in VC. He also reveals why storytelling, strategic name-dropping, and putting your own capital on the line can make all the difference in your career. Whether you're looking to break into the industry or refine your approach, Ethan's insights will help you navigate the highs and lows of venture capital success. Tune in to learn how to leverage relationships, embrace failure, and become a smarter, more resilient investor!Key Points From This Episode:• No straight path: a founder’s guide to a career in early-stage venture capital.• Why empathy and people skills matter more than traditional finance experience.• The power of networks: how relationships open doors.• How the best investors assess risk, luck, and opportunity.• Key traits of successful VCs, including dedication, creativity, and resilience.• Insight into what it really takes to break into the venture capital world.• Taking bold, unconventional action to stand out from the crowd.• The magic of winging it, embracing failure, and just making the leap.

When choosing to invest in a company, there are a lot of elements for VCs to consider—and government policy is no exception. Today on High Stakes, we explore the role of government policy in venture capital and its impact on the industry. Joining Paige Soya to break it all down is Bruce Andrews, who has spent the last 30+ years at the intersection of business, public policy, and politics. Over his career, he’s occupied a range of consequential roles, both in government and commerce, from Deputy Secretary of the US Department of Commerce to Vice President for Global Public Policy at SoftBank. Bruce unpacks the ways government policies affect VCs, how a change in administration can impact startups, and what companies should do to prepare. He sheds light on his time at SoftBank and what it taught him about the VC industry before expanding on how the company helped startups by giving them access to government affairs experts. We also hear Bruce’s reflections on failure and success, his advice to listeners, and more. Join us for a fascinating exploration of government policy and its impact on the industry of venture capital!Key Points From This Episode:Bruce’s background in government and commerce and his time at SoftBank.How American policies compare with regulatory approaches in other countries, like China.Challenges SoftBank successfully navigated when working with the US government.Predictions for the new administration: potential regulatory changes and their effects.How SoftBank helped companies by giving them access to a government affairs team.What Bruce considers his biggest failure in the VC industry and what he learned from it.Final thoughts from Bruce and the best advice he has ever gotten: “Be nice to everyone.”Links Mentioned in Today’s Episode:Bruce Andrews on LinkedInSoftBank GroupGambling Man'Blackstone’s Byron Wien Discusses Lessons Learned in His First 80 Years'Stay at Risk and Live Forever: Lessons from a Life of Curiosity, Grit, and ReinventionPaige Soya on LinkedInK Street CapitalK Street Capital on Youtube

What would you do if you spent two years working relentlessly on a startup idea only to realize no one wants it? That’s exactly what happened to Basel Fakhoury before he and his co-founders scrapped their first business and pivoted to User Interviews, a platform that has now raised $45 million in venture capital. In this episode of High Stakes, Paige Soya sits down with Basel to break down what it really takes to raise money from VCs, from navigating rejections to mastering the fundraising narrative. They cover the art of building investor relationships (spoiler alert: it’s a long game!), the must-have data points and deal terms that can make or break a pitch, why a strong financial story matters just as much as traction, and how User Interviews transitioned from a scrappy Craigslist hustle to a SaaS powerhouse. Plus, Basel shares the biggest mistake he made as a founder and the fundraising strategy that changed everything.Key Points From This Episode:• Focusing on things you can control: what it takes to raise venture capital.• What investors actually look for and how to make it easier for them to say yes.• The psychology behind a VC’s biggest fear (and how to leverage it).• Why warm introductions and investor networks are crucial.• Reasons that transparency and consistency are key in VC due diligence.• Red flags that make term sheets a dealbreaker for founders and funders.• One thing that VCs really want to know: can you do it again?Links Mentioned in Today’s Episode:User InterviewsBasel Fakhoury on LinkedInBasel Fakhoury on XEntrepreneurs Roundtable Accelerator (ERA)The Lean StartupPaige SoyaK Street CapitalK Street Capital on YouTube

In the final episode of Season 2, K Street Capital’s Managing Partner, Paige Soya, sits down with Greg Vetter—the driving force behind Tessemae’s, one of the nation’s most iconic condiment brands.Greg unpacks the journey of growing a family business into a brand that was valued at $300M+ at its peak. From navigating the fallout of the pandemic to ultimately filing for Chapter 11, his story is one of grit and perseverance.He also opens up about his new book, “Undressed: The Unfiltered Story of My Failed American Dream and How It Led to Success,” offering a candid look at the lessons learned along the way.A fitting close to a season all about exits—don’t miss this one.Greg’s book- https://www.amazon.com/Undressed-Unfiltered-Failed-American-Success/dp/0960127704Connect with us here:1. Greg Vetter: https://www.linkedin.com/in/gregvetter/2. Paige Soya: https://www.linkedin.com/in/paigesoya/3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

In this episode of High Stakes, Dimitry Gershenson shares how his team tackled the operational and financial diligence required to pull it off, in this conversation K Street Capital’s Managing Partner, Paige Soya.Dimitry reflects on the challenges of validating key information, noting that diligence often means asking the same question in multiple ways to uncover inconsistencies.They discuss the importance of trusting your instincts during the diligence process and how open, honest communication can make or break a successful transaction.Connect with us here: 1. Dimitry Gershenson: https://www.linkedin.com/in/dgershenson/2. Paige Soya: https://www.linkedin.com/in/paigesoya/3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

What started as an MBA class idea led to an acquisition by one of the nation’s leading baby and kid gear marketplaces.Alli Cavasino and Natalie Poston, founders of JoyLet, built a no-frills “rent-the-runway” model for baby gear, allowing parents to rent items for the time they need.In EP 19 of High Stakes, Alli and Natalie join Paige Soya, Managing Partner of K Street Capital, to discuss the exit and how they navigated the roadblocks in their journey.Connect with us here:1. Alli Cavasino- https://www.linkedin.com/in/allicavasino/2. Natalie Poston- https://www.linkedin.com/in/natalieposton/3. Paige Soya: https://www.linkedin.com/in/paigesoya/4. K Street Capital: https://www.linkedin.com/company/kstreetvc/00:00 Introduction00:47 Meet the Founders: Ali and Natalie01:41 The Birth of Joylette04:41 Early Challenges and MVP Development05:38 Raising Capital and Going Full-Time07:31 Learning and Pivoting the Business Model09:34 Customer Acquisition Strategies16:43 Deciding to Exit19:34 The Exit Process24:43 Reflections and Future Plans

How do you leverage intellectual property for M&A?In this episode of High Stakes, Todd Bracher joins Paige Soya to answer. With over 20+ years experience in building great products, Todd believes that the world’s biggest problems already have solutions, but they need the right design approach to shine.They discuss:- how better design can give your patent the moat it needs- TRLs and IP litigation attorneys- making a product market-ready Don’t miss out. Connect with us here: 1. Todd Bracher: https://www.linkedin.com/in/toddbracher/2. Paige Soya: https://www.linkedin.com/in/paigesoya/3. K Street Capital: https://www.linkedin.com/company/kstreetvc/Resources: 1. Design in Context (Todd’s book)- https://www.toddbracher.com/book2. Market Efficiency Index (Free tool for founders/investors)- https://www.toddbracher.com/mei

Hookit was acquired by KORE Software for much more than the $20 million they raised over three funding rounds.But getting there was no walk in the park.In this episode of High Stakes, K Street Managing Partner Paige Soya is joined by Scott Tilton, exited co-founder of Hookit.They discuss:• how Hookit got acquired for 2x the offer price• why co-founders need to be aligned before the big close• embracing the shift to becoming an employee after a mergerConnect with us here: 1. Scott Tilton: https://www.linkedin.com/in/tiltcore/2. Paige Soya: https://www.linkedin.com/in/paigesoya/3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Managing our digital footprints has become almost impossible without the right tech.Personal data is more vulnerable than ever, and cybercriminals are ready to take advantage.That’s where PrivacyHawk steps in — your defense against this growing digital chaos.We're thrilled to have backed PrivacyHawk in its recent $3M funding round.In this conversation with Aaron Mendez, CEO of PrivacyHawk, we discuss everything from dead weight on your cap table, the need for a better understanding of liquidation preferences, and why you're better off selling early rather than too late.Connect with us here: 1. Aaron Mendes: https://www.linkedin.com/in/mendes/2. Paige Soya: https://www.linkedin.com/in/paigesoya/3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Building a company for exit? Prepare for the long haul.In this encore episode, hosted by Paige Soya, Richard Leggett, former CEO of FrontierView, and lead investor Tom McCormick dive into the harsh realities of the world of M&A.They share how they navigated the pressures of competing priorities, kept the business afloat during the pandemic, and avoided a fire sale by strategically positioning for a successful exit.With candid insights on resilience, timing, and critical decision-making, this episode is a must-watch for entrepreneurs facing tough choices.Note: This episode is a re-upload with added substance and a quick sneak peak into the conversation at the start. Enjoy!

In this episode of High Stakes, host Paige Soya dives in with Zach Axelrod, CEO of Redball Energy, uncovering the game-changing moments that shaped his entrepreneurial success. Discover:• How financial leverage and perfect timing led to Zach's career-defining $100M exit• Insider tips on maximizing returns from high-growth investments• Crucial lessons on negotiation power dynamics and maintaining controlZach's candid insights on market timing, profit-taking, and strategic flexibility are pure gold. Don't miss this masterclass in entrepreneurial wisdom!

Imagine thinking your startup is doomed, only to be acquired for $165M.On this episode of High Stakes, Russ Hiddleston shares the wild ride that led to DocSend’s $165 million acquisition by Dropbox.In this chat with Managing Partner Paige Soya, they discuss funding, exits, Russ’s next venture, Distill (hint: think Wikipedia but for company and people summaries).

In episode 12 of High Stakes, Paige Soya, Managing Director of K Street Capital, interviews Marcus Brauchli, co-founder of North Base Media and former managing editor at the Wall Street Journal, on the intricacies of investment exits. Marcus shares his extensive experience in the venture capital world, highlighting the lessons learned from both successful and failed exits. They cover the wide range of stories Marcus has to share on the importance of legal documentation, the complexities of international investments, and the various exit strategies companies may face. Marcus also emphasizes the necessity for founders to plan for exits from the beginning and maintain open communication with investors. Tune in for insightful advice on navigating the unpredictable landscape of venture capital exits.

In Episode 11 of High Stakes, Paige Soya interviews Sean Griffey, CEO of Industry Dive. Griffey discusses Industry Dive's journey from bootstrap beginnings to a company with $100 million in revenue and over 400 employees, culminating in its acquisition by Falfurrias Capital. He emphasizes the importance of preparation and cultural fit in acquisitions. Griffey also shares insights into Industry Dive's subsequent acquisition by Informa in 2022, navigating the transition from private equity ownership to being part of a large public corporation, and the opportunities and challenges it brought.

In episode 10 of High Stakes, Paige Soya, Managing Partner at K Street Capital, and Joe Fluet, Founder of Fluet Law Firm and MAG Aerospace, discuss Fluet’s journey from founding MAG to navigating significant exits and recaps. He emphasizes a values-driven approach to business, discussing how aligning with investors who share these values is crucial for long-term success. Tune in to hear Fluet’s insights underscoring the complexity and critical decisions involved in building lasting, impactful companies.

Join us as we dive into the world of multiple exits with Martin Tobias, Managing Partner of Incisive Ventures. Martin brings a wealth of experience and perspective as a GP and a three-time venture-funded CEO who has navigated IPOs and strategic acquisitions, sharing insights from his journey with Loud Eye Technologies, among others. He discusses the nuances of laddering and IPO pricing, the challenges of lock-up periods, and strategies for managing concentrated positions post-exit. Tune in to Martin and Paige’s discussion on the dynamics of modern exit strategies and valuable perspectives for both founders and investors.

Political operative turned tech entrepreneur, Sara Fagen, shares a wealth of knowledge in this episode of High Stakes. Join us as Sarah and host Paige Soya discuss lessons from raising venture capital, timing an exit, the dynamics of venture-backed versus self-funded businesses, and strategic reasons behind acquisitions in the tech industry. Throughout the conversation, Sarah reflects on the realities of building and exiting successful tech companies.

Join us as we sit down with Hans Miller, founder of Airside, a pioneering company in the digital identity and travel space, to explore his strategic exit during the COVID-19 pandemic. Hans shares how the pandemic reshaped Airside's trajectory, and offers lessons learned for startup founders and his perspectives on the future landscape of digital identity in travel. Hans's candid reflections provide valuable insights for founders and investors alike.

Step into the boardroom with host Paige Soya, seasoned public investor and former investment banker specializing in IPOs Rob Schwartzberg, and investment banker specializing in mergers and acquisitions Darren Womer as they discuss two paths that founders may ultimately find themselves deciding between: M&A or IPO. Drawing from their extensive experience and expertise, Rob and Darren offer listeners a behind-the-scenes look at both processes, sharing insider tips and practical advice for founders taking their businesses to the next level. 

In this episode of High Stakes, host Paige Soya chats with serial entrepreneur Rami Essaid about his journey founding, scaling, and ultimately exiting three successful companies. From paying his way through college selling cell phones in a mall to leading multimillion-dollar ventures, Rami's journey is marked by a series of strategic exits, each offering unique challenges and lessons. He candidly discusses the need for founders to keep doors open, maintain optionality, and prioritize strategic alignment when considering exit opportunities. Whether negotiating with investors, managing expectations, or planning for the future, his pragmatic advice serves as a guiding light for entrepreneurs navigating the complex landscape of exits.

Explore the intersection of risk and reward in the cannabis industry with Mark Smith's candid account of one of his earliest investments. From early optimism to unexpected challenges, Mark shares the valuable lessons he learned while investing in a rapidly evolving industry and the resilience required to weather the storms of market volatility.

Mei Xu's inspiring story is one of resilience, determination, and true entrepreneurial spirit. With candor and wisdom, Mei recounts the challenges and triumphs of navigating the sale of her business, providing a poignant glimpse into the emotional and practical complexities she encountered along the way. From managing the demands of chemotherapy to overseeing a high-stakes business transaction, Mei offers a compelling narrative of entrepreneurship as a journey of growth, discovery, and passionate pursuit of excellence.

Join host Paige Soya and featured guests, Richard Leggett, former CEO of FrontierView and Tom McCormick, lead investor, as they discuss their highly successful exit after facing unprecedented challenges including the impact of the pandemic and rescuing the company from a potential fire sale offer. Rich and Tom offer candid insights into lesson’s learned and the importance of adaptation, resilience, and strategic decision making in a dynamic business environment.  

In this Season 2 premiere, host Paige Soya sits down with Roy Schwartz, exited founder/CEO of Axios, to discuss his journey through exits and entrepreneurship. The conversation highlights the complexities of acquisition deals, the rollercoaster of negotiations, and the importance of finding the right fit for both parties involved. Roy sheds light on the pivotal decisions that are made during the exit process, when to say no, when to say yes, and how to keep dialogue open and communication transparent so that acquirers and founders can align. His exit experience with Axios exemplifies how rewarding it can be to stay in the game until you find just the right buyer. 

Join us in the final episode of Season 1 of High Stakes as we delve into the vibrant world of Consumer Marketing and GTM strategies. Hear firsthand insights from Shizu Okusa, the visionary behind Apothekary's wellness journey; and Sahil Rahman, the co-founder of Rasa, who's charting new territories in the restaurant industry. Together with host, Paige Soya, they'll shed light on the challenges, innovations, and foresights of today's dynamic venture landscape. 

In this episode, we dive into the do's and dont's founders should know while fundraising. To help dig into this topic are two members of the K Street Capital team, Nick Duafala, Principal, and James Culver, Associate. Tune in to gain the knowledge and strategies that can make a real difference in your startup's fundraising efforts. Whether you're a seasoned entrepreneur or just starting your journey, this episode provides essential guidance from the experts at K Street Capital.

In this episode of High Stakes, Paige Soya sits with Climate Tech pioneers Logan Soya and Kiran Bhatraju of Arcadia. Dive into an enlightening discussion about the confluence of Climate Tech and VC. Explore the intricacies of atoms vs bits investing and the burgeoning world of Climate Fintech. Discover the concept of transforming buildings into power plants and dissect the rise of SPACs in the sector. As both seasoned investors and groundbreaking founders, Kiran and Logan offer a unique dual-perspective on the challenges and opportunities of the current exit landscape. Tune in for a conversation packed with insights, trends, and expert advice.

In this episode of High Stakes, seasoned investors Ed Ingle and Jonah Seiger join Selena Strandberg, founder of "The Know", to delve deep into the realm of real-time employee sentiment analysis. As they weave through the intricate tapestry of venture capital, they shed light on the pivotal role such tools play for C-Suites, VCs, and startups. The discussion offers invaluable insights for both budding founders and astute investors. A must-listen for those eager to grasp the pulse of modern VC trends and the tech shaping them.

This episode addresses a question that we’ve seen come up in popular media lately: Are startups dying and VCs backing away? To help answer this question are two members of the K Street Capital team, Nick Duafala, Principal, and James Culver, Associate. In their conversation, Paige, Nick, and James reflect on K Street Capital's unique investment philosophies and share insights from their firsthand experiences. Listeners will gain insights into whether startups are in fact facing challenges and if VC firms are becoming more cautious in their investments.