High Stakes

Join seasoned investors and successful start-up founders as they weigh in on topics and trends currently dominating the venture capital space. Each episode brings together a founder and an investor to provoke a deepened understanding of the topic at hand. If you want to learn about how early-stage venture capital investing works, this show is for you.

High Stakes is a business podcast hosted by Paige Soya, with 72 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Paige Soya hosts High Stakes, a business show with 72 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #11

  Go-to-Market Is the Moat | Paige Soya, Nick Duafala, and Mark Schacknies (NFTYDoor)

  Aug 6, 202646 minS4

  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 its distribution strategy. NFTYDoor went on to become one of the country's leading white-label HELOC platforms, serving 500+ lenders, 36,000+ mortgage loan officers, and approaching $7B in annual run-rate volume before its successful exit. Using NFTYDoor's journey as a case study, they explore why venture investors increasingly evaluate go-to-market execution alongside technical differentiation, how AI is reshaping startup defensibility, and what founders should focus on to build businesses competitors can't easily replicate. In this episode: What venture capitalists mean by a competitive moat Why product-market fit comes before scalable distribution How distribution becomes a durable competitive advantage The role of network effects and switching costs Why founders should understand—not avoid—the competition How focus creates defensibility in crowded markets Why customer discovery matters more than the perfect pitch Practical advice for founders raising venture capital Whether you're building a startup, evaluating investment opportunities, or interested in how venture capitalists think about competitive advantage, this episode provides actionable insights into building durable businesses in the AI era. Topics: Venture Capital • Startup Fundraising • Competitive Moats • Startup Strategy • Product-Market Fit • Distribution Strategy • Network Effects • Switching Costs • Founder Advice • Go-to-Market Strategy • Startup Growth • Venture Investing

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  Episode #10

  How VCs Structure Venture Deals | Paige Soya, Nick Duafala & Scott Stern (Partner, Origin Ventures)

  Jul 23, 202652 minS4

  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: The differences between SAFEs, convertible notes, and priced equity rounds How valuation, dilution, and cap tables really work Why founder vesting exists and what investors are protecting Liquidation preferences, option pools, and anti-dilution explained Pro rata rights and why investors negotiate for them Common fundraising mistakes founders should avoid How to approach your first venture capital term sheet with confidence 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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  Episode #9

  How VCs Evaluate Pre-Revenue Startups | Paige Soya, Nick Duafala & Charles Hudson (Precursor Ventures)

  Jul 9, 202635 minS4

  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. In this episode, we discuss: Why pre-revenue investing requires a different approach than later-stage venture investing The two founder archetypes Charles sees most often: industry insiders and "naive outsiders" How investors determine whether a founder has a unique and durable insight Why proximity to a problem can be one of a founder's greatest advantages The difference between product innovation and business model innovation Why distribution strategy can matter just as much as the product itself How VCs evaluate founders when there is little customer or revenue data Why resourcefulness and perseverance are two of the strongest predictors of founder success How market timing influences pre-seed investment decisions Why being slightly late can sometimes be better than being too early What Charles learned from founders who succeeded inside large companies but struggled as startup CEOs How resilience and life experiences shape a founder's ability to navigate uncertainty Key Takeaways 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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  Episode #8

  Venture Liquidity, Secondaries & How VCs Exit | Paige Soya, Nick Duafala & Andrew (Principal at Savano Capital)

  Jun 25, 202636 minS4

  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: What venture secondaries are and how they work The difference between primary and secondary transactions Why startups are staying private longer The rise of the secondary market and what is driving its growth How founders, employees, and investors access liquidity before an IPO Why secondaries are becoming a critical component of venture capital exits The future of private market liquidity 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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  Episode #7

  VC Deal Timelines & Due Diligence | Paige Soya, Nick Duafala & Matt Bressler (Lookout Ventures & Fmr TDF Ventures)

  Jun 11, 202637 minS4

  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: Venture capital deal timelines How investors evaluate startup opportunities What creates fundraising momentum Preparing for investor due diligence Common fundraising mistakes founders make Building investor relationships before a raise Why some venture deals move faster than others 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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