Podcast by Paige Soya
28 August 2025
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:
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.
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46:01
14 August 2025
“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:
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.
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33:51
06 August 2025
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.
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38:15
17 July 2025
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.
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41:31
03 July 2025
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.
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37:49
20 June 2025
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.
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39:33