High Stakes

In this episode of High Stakes, K Street Capital Managing Partner Paige Soya continues the Venture Capital 101 season with a conversation about the user journey: how products get sold, activated, and adopted, and why VCs pay close attention to it. She’s joined by Mike Desai, co-founder and CEO of Truentity Health, which gives independent pharmacies, many serving rural communities, the infrastructu...

What actually determines what a startup is worth? In this episode of High Stakes, K Street Capital’s Paige Soya and Nick Duafala are joined by investment team members Joseph and Jose for a Venture Capital 101 breakdown of how VCs assess startup valuations and why it’s rarely as simple as founders might assume. The conversation begins with the core VC perspective: valuation isn’t based solely on wh...

What makes a business venture-backable? In this episode of High Stakes, K Street Capital’s Paige Soya and Nick Duafala sit down with Jonathan Sherry, founder and CEO of Alium and former co-founder of CB Insights, for a Venture Capital 101 discussion about the business models VCs evaluate and what makes them scalable, defensible, and fundable. The conversation covers the fundamentals of SaaS and ma...

For years, founders and investors have used terms like “fintech,” “SaaS,” and “platform” without always having a shared definition. But as venture firms rely more heavily on data to track deals, returns, and portfolio performance, getting that language right matters more than ever. In this episode of High Stakes, Paige Soya and Nick Duafala are joined by K Street Capital’s Joseph Whang and Jose Ci...

What actually creates a competitive moat? For years, founders believed the answer was simple: build a better product. Today, venture investors increasingly believe the answer is distribution. In this episode of High Stakes, Paige Soya and Nick Duafala are joined by Mark Schacknies, CEO & Co-Founder of NFTYDoor—a company K Street backed in its earliest stages after recognizing the strength of i...

Not all venture deals are created equal, and understanding the fine print can make a significant difference for founders. In this episode of High Stakes, K Street Capital's Paige Soya and Nick Duafala are joined by Scott Stern, Partner at Origin Ventures, to break down how venture capital deals are actually structured. From SAFEs and convertible notes to priced equity rounds, founder vesting, liqu...

What makes a pre-revenue startup worth investing in? Before there's revenue, traction, or a long list of customers, venture investors have to make decisions with limited data. So what signals matter most? How do VCs build conviction around a founder and an idea when so much is still uncertain? In this episode of High Stakes, Paige Soya and Nick Duafala sit down with Charles Hudson, Managing Partne...

How do venture capital firms actually exit their investments when startups are staying private longer than ever before? On this episode of High Stakes, hosts Paige Soya and Nick Duafala sat down with Andrew Seter, Principal at Savano Capital, to unpack venture liquidity, the growing secondary market, and how founders, employees, and investors are accessing liquidity outside of traditional IPOs and...

How long does it actually take to raise venture capital? In this episode of High Stakes, Paige Soya and Nick Duafala sit down with Matt Bressler, Co-Founder and General Partner at Lookout Ventures, formerly TDF Ventures, to discuss venture capital deal timelines, fundraising momentum, and the diligence process that takes place behind every investment decision. From initial founder meetings to sign...

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 mome...

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 h...

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 thos...

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 netw...

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 fou...

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 ow...

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...

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 ch...

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...

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 representa...

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 an...

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 re...

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)...

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...

“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 strateg...

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,...