High Stakes

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.

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 flow

Whether you’re a VC or an operator, this conversation is packed with timeless advice.