High Stakes

Hosted by Paige Soya

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Latest episode

Jun 2026

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EN-US

About the show

Join seasoned investors and successful start-up founders as they weigh in on topics and trends currently dominating the venture capital space. Each episode brings together a founder and an investor to provoke a deepened understanding of the topic at hand. If you want to learn about how early-stage venture capital investing works, this show is for you.

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60 recent

June 11, 202637 min

VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)

How long does it actually take to raise venture capital?In this episode of High Stakes, Paige Soya and Nick Duafala sit down with Matt Bressler, Co-Founder and General Partner at Lookout Ventures, formerly TDF Ventures, to discuss venture capital deal timelines, fundraising momentum, and the diligence process that takes place behind every investment decision.From initial founder meetings to signed term sheets, they explore what causes fundraising processes to move quickly, what causes deals to stall, and why many of the fastest investments begin months—or even years—before a company officially starts raising capital.Topics covered include:Venture capital deal timelinesHow investors evaluate startup opportunitiesWhat creates fundraising momentumPreparing for investor due diligenceCommon fundraising mistakes founders makeBuilding investor relationships before a raiseWhy some venture deals move faster than othersWhether you're raising your first round, preparing for a future fundraise, or simply interested in how venture capital works behind the scenes, this episode offers practical insights into how investors build conviction and make investment decisions.Subscribe for more conversations with founders, investors, and operators shaping the startup ecosystem.

May 28, 202651 min

Power Dynamics in VC | Paige Soya, Nick Duafala, Haley Bryant (Hustle Fund), & Ann Marie Guzzi (Dalmatian Ops, Angel Investor & Agora Initiative)

In this episode of High Stakes, K Street Capital’s Paige Soya and co-host Nick Duafala sit down with Haley Bryant, Partner at Hustle Fund, and Ann Marie Guzzi, angel investor, Managing Partner of Dalmatian Ops and Co-Founder of The Agora Initiative, for a deep dive into one of the most misunderstood topics in venture capital: power dynamics.From the moment a founder starts fundraising to the moment a company exits, who actually has the power, and how does that shift over time?The conversation breaks down:Who really makes investment decisions inside VC firmsHow LPs influence deal flow and investor convictionWhy founders often underestimate their leverageThe hidden dynamics between associates, partners, and investment committeesHow governance changes after the check gets writtenWhy founder-investor alignment matters at exitIPOs vs M&A vs secondary transactionsHow board control and voting shares shape outcomesWhy relationships and reputation matter throughout the venture ecosystemAlong the way, the group shares candid insights on:Why fundraising feels a lot like datingThe difference between scarcity and abundance mindsetsWhat happens behind the scenes during diligenceHow market conditions shift founder leverageWhy the best founders ultimately hold more power than they realizeWhether you’re a founder raising your first round, an emerging investor, or simply curious about how venture capital actually works behind closed doors, this episode offers an honest look at the incentives, relationships, and structures that shape startup outcomes.Subscribe to High Stakes for more conversations breaking down the realities of venture capital, startups, and company building.

May 14, 202641 min

How VCs Evaluate Founding Teams | Paige Soya, Nick Duafala, & Neil Shah (CEO, ThinkNimble)

Most people assume VCs are evaluating traction, revenue, or the pitch deck first.Those things matter — but often, the real signal is something harder to quantify: how a founder thinks.In this episode of High Stakes, Nick Duafala and I sat down with Neil Shah (CEO of ThinkNimble) to unpack how investors actually evaluate founding teams — especially in a market where AI is fundamentally changing how companies get built.A few take aways:→ You can often tell within the first 15–20 minutes whether a founder has the qualities you want to back.→ Investors are ultimately evaluating the quality of thinking behind the business — not just the business itself.→ As AI removes more of the execution friction, thoughtful strategy, judgment, and founder insight become even greater differentiators.We also get into:Why second-time founders often have an edgeHow AI is changing startup team designWhat “deep thinking” actually looks like in foundersWhy pattern recognition still matters in venture What investors are really evaluating in that first meeting

April 30, 202639 min

Angel Investors vs. VCs | Paige Soya & Dadi Akhavan (Startup-to-IPO Founder)

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.

April 16, 202649 min

How VCs Source Deals | Paige Soya, Nick Duafala & Taylor Margot (Partner, Lytical Ventures)

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

April 2, 202631 min

Not All Capital Is Created Equal: Venture Capital vs. Other Funding | Paige Soya & Jill Ralph (Former Chemonics Capital and Motley Fool)

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.

March 12, 202635 min

An Introduction to Venture Capital: Meet your hosts | Paige Soya & Nick Duafala at K Street Capital: Season 4 of High Stakes

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.

December 9, 202547 min

Unlocking Women Investing in VC with Julie Castro Abrams

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

November 20, 202547 min

What VCs and Angel Investors are seeing from Y-Combinator in 2025

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.

November 6, 202537 min

How Early Funding Rounds a Shape Startup's Future

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.