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to venture—and the systemic obstacles that still stand in their way, from misaligned financial advisor incentives to outdated assumptions about risk, time, and wealth.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.

• 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

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.

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.

• 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 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.

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 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.

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 outcomes
• The importance of market size and market dynamics when evaluating startups
• The pitfalls of messy cap tables, notes, and SAFEs and how they can derail a deal

Sean 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 aligned
• How generative AI is reshaping team size, round size, and outcomes
• What investors really mean when they say they need 10%
• Why early investors can get wiped out even when a company wins

If 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.