Podcast by Paige Soya
23 July 2026
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, liquidation preferences, pro rata rights, and anti-dilution provisions, they explain the terms that shape startup financings—and why they matter for both founders and investors.
Along the way, the conversation explores common fundraising mistakes, why complicated cap tables can derail future financing rounds, and how founders can approach term sheet negotiations with greater confidence. Rather than simply defining venture terminology, this episode explains the reasoning behind the structures investors use and how those decisions can influence a company's long-term success.
Whether you're raising your first round, investing in startups, or simply looking to better understand venture capital, this episode offers practical insights into one of the most important—and most misunderstood—aspects of startup fundraising.
In this episode:
Guest:
Scott Stern, Partner at Origin Ventures
Hosts:
Paige Soya, Managing Partner, K Street Capital
Nick Duafala, Senior Principal, K Street Capital
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52:07
09 July 2026
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 Partner at Precursor Ventures, to explore how investors evaluate startups at the earliest stages of venture.
Charles shares his framework for pre-seed investing, including how he assesses founder insight, market timing, perseverance, resourcefulness, and a founder's ability to turn an early hypothesis into a scalable company.
The conversation explores what separates exceptional founders from the rest—and why, at the pre-seed stage, investing is often as much about the founder as it is about the business.
Great founders don't always have the most experience—they have the strongest insight.
At the pre-seed stage, investors look for evidence that founders understand a problem deeply and have uncovered insights that others have missed.
Resourcefulness is a leading indicator of startup success: Before founders have capital, customers, or large teams, investors can learn a great deal by observing how they create opportunities and solve problems with limited resources.
Timing can be just as important as the idea itself: Even great companies can struggle if the market isn't ready. Successful founders often launch when customer behavior, technology, and market conditions align.
At the earliest stages, investing is ultimately a bet on people: With limited financial or customer data, investors are evaluating a founder's ability to adapt, persevere, and execute through uncertainty.
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34:42
25 June 2026
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 acquisitions.
As private companies delay public offerings and remain private for longer periods of time, secondaries have become an increasingly important part of the venture ecosystem. But what exactly are they, who benefits from them, and why has the market grown so rapidly?
In this episode, we discuss:
Whether you're a founder, operator, investor, or simply curious about how venture capital works behind the scenes, this episode breaks down one of the fastest-growing areas of private markets in an approachable way.
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35:41
11 June 2026
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 signed term sheets, they explore what causes fundraising processes to move quickly, what causes deals to stall, and why many of the fastest investments begin months—or even years—before a company officially starts raising capital.
Topics covered include:
Whether you're raising your first round, preparing for a future fundraise, or simply interested in how venture capital works behind the scenes, this episode offers practical insights into how investors build conviction and make investment decisions.
Subscribe for more conversations with founders, investors, and operators shaping the startup ecosystem.
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37:26
28 May 2026
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51:54
14 May 2026
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 how companies get built.
A few take aways:
→ You can often tell within the first 15–20 minutes whether a founder has the qualities you want to back.
→ Investors are ultimately evaluating the quality of thinking behind the business — not just the business itself.
→ As AI removes more of the execution friction, thoughtful strategy, judgment, and founder insight become even greater differentiators.
We also get into:
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41:58