High Stakes

Hosted by Paige Soya

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Latest episode

Aug 2026

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About the show

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.

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60 recent

August 20, 202641 min

Learn the Lingo VCs Actually Use | Paige Soya, Nick Duafala, & K Street Capital

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 Cifuentes for a Venture Capital 101 breakdown of how VCs classify the startups they evaluate. Using real-world examples from Salesforce, Airbnb, Facebook, and Auth0, the team walks through the eight categories that make up K Street’s internal deal taxonomy, why consistent classification matters, and how founders can use the same framework to better understand, and communicate, their businesses. In this episode: The eight categories we use to classify startups Why a company’s industry and its customer’s industry aren’t necessarily the same How B2B, B2C, B2G, and dual-use define customer type Why go-to-market motion—direct, enterprise, product-led, or channel—matters to investors How VCs think about business and revenue models The difference between product type and technology category, and why AI increasingly cuts across both What separates a true platform from a suite of products or services How K Street uses AI internally to keep deal data consistent and comparable Whether you’re a founder refining your fundraising narrative or a new investor learning the language of venture capital, this episode is a practical guide to how VCs actually think about and categorize the companies they evaluate. Topics : Venture Capital • Startup Fundraising • Startup Taxonomy • Business Models • Go-to-Market Strategy • SaaS • Marketplaces • Venture Investing • Founder Advice • Startup Strategy Timestamps 00:00 – Cold open: The data problem behind bad taxonomy 00:58 – Welcome to High Stakes: VC 101 02:04 – Meet the deal team: Joseph & Jose 05:09 – The 8 categories of startup taxonomy 05:50 – Category 1: Industry 06:52 – Verticals within industries + the “customer industry” mistake 11:27 – Category 2: Customer type (B2B/B2C/B2G) & market characteristics 12:26 – Dual-use, government contracting & defense tech 14:37 – Category 3: Go-to-market strategy 19:19 – Category 4: Business model & revenue model 21:44 – Can a services business be venture-backable? 26:19 – Category 5: Product type 28:16 – Category 6: Technology (AI, quantum, space & robotics) 32:01 – How K Street uses AI internally for deal data 36:11 – What makes something a true “platform”? 38:03 – Rapid fire: Hidden talents, biggest mistakes & best advice 41:01 – Final thoughts

August 6, 202645 min

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

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

July 23, 202652 min

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

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

July 9, 202634 min

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

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.

June 25, 202635 min

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

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.

June 11, 202637 min

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

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.

May 28, 202651 min

Power Dynamics in VC | Paige Soya, Nick Duafala, Haley Bryant (Hustle Fund), & Ann Marie Guzzi (Dalmatian Ops, Angel Investor & Agora Initiative)

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 moment a company exits, who actually has the power, and how does that shift over time? The conversation breaks down: Who really makes investment decisions inside VC firms How LPs influence deal flow and investor conviction Why founders often underestimate their leverage The hidden dynamics between associates, partners, and investment committees How governance changes after the check gets written Why founder-investor alignment matters at exit IPOs vs M&A vs secondary transactions How board control and voting shares shape outcomes Why relationships and reputation matter throughout the venture ecosystem Along the way, the group shares candid insights on: Why fundraising feels a lot like dating The difference between scarcity and abundance mindsets What happens behind the scenes during diligence How market conditions shift founder leverage Why the best founders ultimately hold more power than they realize Whether you’re a founder raising your first round, an emerging investor, or simply curious about how venture capital actually works behind closed doors, this episode offers an honest look at the incentives, relationships, and structures that shape startup outcomes. Subscribe to High Stakes for more conversations breaking down the realities of venture capital, startups, and company building.

May 14, 202641 min

How VCs Evaluate Founding Teams | Paige Soya, Nick Duafala, & Neil Shah (CEO, ThinkNimble)

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: Why second-time founders often have an edge How AI is changing startup team design What “deep thinking” actually looks like in founders Why pattern recognition still matters in venture What investors are really evaluating in that first meeting

April 30, 202639 min

Angel Investors vs. VCs | Paige Soya & Dadi Akhavan (Startup-to-IPO Founder)

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 those differences shape everything from deal selection to decision-making to founder outcomes. Key themes include: Why venture capital funds are structurally driven to pursue “outlier” returns How fund size, LP expectations, and mandates influence VC behavior Why angel investors have more flexibility in what and when they invest How early-stage founders should think about which type of capital to raise — and when The tradeoffs between taking institutional money vs. staying in the angel ecosystem What “stage of company” really means in practice for fundraising strategy How experienced investors evaluate opportunity differently based on structure, not just preference Dadi also shares insights from his own journey, from building companies to taking one from startup all the way to IPO, and how that experience shapes his approach to investing today. This episode is a deep dive into the mechanics behind startup funding decisions, and what founders often overlook when choosing between angels and VCs.

April 16, 202649 min

How VCs Source Deals | Paige Soya, Nick Duafala & Taylor Margot (Partner, Lytical Ventures)

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 networks to unexpected moments of curiosity, and why the strongest opportunities are often driven by relationships, not cold outreach. The conversation goes beyond surface-level advice to explore how sourcing has evolved, the role of personal brand, and why depth matters more than breadth in today’s market. For founders, this episode is a playbook. The group shares practical strategies for getting in front of VCs, from leveraging your network the right way to standing out at events, and what not to do if you want to build lasting investor relationships. They also dive into the psychology behind cold outreach, why most inbound gets ignored, and how to increase your odds of getting that first meeting. Whether you're an investor looking to build deal flow or a founder trying to raise capital, this episode offers a clear, tactical look at how connections actually turn into deals and how to position yourself on the right side of that equation. What you’ll learn: -How VCs really source deals (and why it’s not just about “who you know”) -The difference between warm intros, cold outreach, and organic discovery -Why deep relationships outperform wide networks -How founders can effectively get in front of investors -The biggest mistakes founders make when approaching VCs -Why venture is a long game—and how to play it