Business

High Stakes

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.

Latest Episodes:

Power Dynamics in VC | Paige Soya, Nick Duafala, Haley Bryant (Hustle Fund), & Ann Marie Guzzi (Dalmatian Ops, Angel Investor & Agora Initiative) May 28, 2026

Show notes

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 firms
How LPs influence deal flow and investor conviction
Why founders often underestimate their leverage
The hidden dynamics between associates, partners, and investment committees
How governance changes after the check gets written
Why founder-investor alignment matters at exit
IPOs vs M&A vs secondary transactions
How board control and voting shares shape outcomes
Why relationships and reputation matter throughout the venture ecosystem

Along the way, the group shares candid insights on:

Why fundraising feels a lot like dating
The difference between scarcity and abundance mindsets
What happens behind the scenes during diligence
How market conditions shift founder leverage
Why the best founders ultimately hold more power than they realize

Whether 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.

How VCs Evaluate Founding Teams | Paige Soya, Nick Duafala, & Neil Shah (CEO, ThinkNimble) May 14, 2026

Show notes

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 edge
How AI is changing startup team design
What “deep thinking” actually looks like in founders
Why pattern recognition still matters in venture
What investors are really evaluating in that first meeting

Angel Investors vs. VCs | Paige Soya & Dadi Akhavan (Startup-to-IPO Founder) Apr 30, 2026

Show notes

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” returns
How fund size, LP expectations, and mandates influence VC behavior
Why angel investors have more flexibility in what and when they invest
How early-stage founders should think about which type of capital to raise — and when
The tradeoffs between taking institutional money vs. staying in the angel ecosystem
What “stage of company” really means in practice for fundraising strategy
How experienced investors evaluate opportunity differently based on structure, not just preference

Dadi 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 VCs Source Deals | Paige Soya, Nick Duafala & Taylor Margot (Partner, Lytical Ventures) Apr 16, 2026

Show notes

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

Not All Capital Is Created Equal: Venture Capital vs. Other Funding | Paige Soya & Jill Ralph (Former Chemonics Capital and Motley Fool) Apr 02, 2026

Show notes

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 classes
What diversification looks like in a venture portfolio
How long it typically takes to see returns
What it means to be an accredited investor and how much capital you need to get started
How venture-backed companies differ from traditional businesses

Whether 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.

An Introduction to Venture Capital: Meet your hosts | Paige Soya & Nick Duafala at K Street Capital: Season 4 of High Stakes Mar 12, 2026

Show notes

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 platform
Why early-stage investing is different from traditional finance
What makes venture capital unique compared to other asset classes
How investors evaluate startups and work alongside founders

Along 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.

Unlocking Women Investing in VC with Julie Castro Abrams Dec 09, 2025

Show notes

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 Investing

Why the biggest limitations aren’t ability or interest, but access, time, exposure, and friction
How financial advisors, often unknowingly, disincentivize clients from exploring alternative investments like VC
Why the question “Do you personally invest in venture?” can reveal critical advisor blind spots
How inherited wealth, fear, lack of exposure, and over-reliance on traditional systems impact women differently

What VCs and Angel Investors are seeing from Y-Combinator in 2025 Nov 20, 2025

Show notes

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 scenes
What investor ratings mean for fundraising strategy
Why reputation has become a competitive advantage for VCs and angels
How this shift is redefining accountability in venture capital

Watch now to learn how your reputation has become your strategy in the evolving world of startup investing.

How Early Funding Rounds a Shape Startup's Future Nov 06, 2025

Show notes

The High-Stakes Decisions Behind Early Fundraising: When to Raise, Who to Raise From, and How Much Equity to Give Up

In 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.

How Diverse Founders Drive Bigger Wins Oct 23, 2025

Show notes

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.