High Stakes

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Podcast by Paige Soya

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

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20 November 2025

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 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.

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47:47

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06 November 2025

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 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.

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37:31

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23 October 2025

How Diverse Founders Drive Bigger Wins

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.

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38:55

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09 October 2025

The Art and Science of Diligence in Early-Stage VC

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 startups
  • How speed, style, and grit signal founder potential
  • Why the way a founder articulates their vision can matter more than the metrics
  • The limits of AI in a process that’s deeply qualitative and human-driven

Whether 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.

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47:06

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25 September 2025

How VC success is truly measured

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.

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42:27

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11 September 2025

What LPs Want from VC Fund Managers

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 fund
  • Why many institutional investors are leaning into emerging managers
  • How individual LPs think about risk, liquidity, and the “long game” of venture
  • The difference between being an investor and being a fund manager
  • Why strong communication, transparency, and firm-building matter just as much as returns

Nasir 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.

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35:56