High Stakes

Hosted by Paige Soya

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Latest episode

Oct 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

October 15, 202643 min

The 6 Unit Economics VCs Use to Evaluate Startups | Paige Soya, Nick Duafala & K Street Capital

In this episode of High Stakes, K Street Capital Managing Partner Paige Soya and Principal Nick Duafala continue the Venture Capital 101 season with a discussion about unit economics: how investors evaluate a company's financial performance, efficiency, and potential to scale. Joined by members of K Street Capital's investment team, Paige and Nick break down the key metrics the firm looks at when evaluating startups, particularly SaaS businesses, and explains why founders should understand their expected economics even before generating revenue. The conversation covers lifetime value to customer acquisition cost (LTV), gross margins, CAC payback period, churn, net revenue retention, and the efficiency of revenue growth. The team explains what healthy benchmarks can look like, why the direction of a metric matters just as much as its current value, and how founders can use these numbers to make better business decisions. They also explore how AI is changing traditional SaaS economics, why higher infrastructure costs can sometimes make sense when growth justifies them, and why investors need evidence before changing their benchmarks. The episode closes with a discussion about adapting to uncertainty, lessons from career mistakes, and the importance of communication and teamwork. We dive into What unit economics mean and why VCs evaluate them at the seed stage Why founders should model expected economics before generating revenue How investors evaluate the LTV ratio and what a 3–5x ratio can indicate Why SaaS businesses typically aim for 70–90% gross margins How business models influence gross margin expectations Why improving financial metrics can matter more than hitting a benchmark today How AI companies are challenging traditional SaaS margin expectations What CAC payback period tells investors about customer acquisition efficiency How churn and net revenue retention affect customer lifetime value Why revenue growth needs to be evaluated alongside profitability and efficiency How investors think about burn rate and the efficiency of capital deployment Why founders should track unit economics even when they aren't raising money How VCs decide whether traditional benchmarks still apply to AI businesses What a consulting project taught Joseph about communication, validation, and teamwork Chapters 00:00 Intro: Understanding Unit Economics 00:50 Welcome to High Stakes: Venture Capital 101 02:30 Why Unit Economics Matter Before You Have Revenue 05:50 LTV:CAC: Measuring Customer Acquisition Efficiency 09:20 Gross Margins: What VCs Look for in SaaS 12:00 Revenue Growth, Margins & Business Model Trade-Offs 14:00 Evaluating Margins in AI Companies 16:55 CAC Payback Period: How Long to Recover Acquisition Costs 19:30 Churn & Net Revenue Retention 22:00 Revenue Efficiency & Predictability 24:00 Burn Multiple & Capital Efficiency 26:00 Evaluating Burn Rate and Startup Growth 28:00 Why Financial Benchmarks Need Context 29:00 AI Costs, Growth & the Future of Unit Economics 30:00 Final Thoughts on Unit Economics 32:00 Joseph's Side Projects Outside of Venture Capital 35:55 Career Mistakes, Validation & Team Communication 37:45 Closing Thoughts Topics: Venture Capital • Unit Economics • SaaS Metrics • LTV • Customer Acquisition Cost • CAC Payback Period • Gross Margins • Net Revenue Retention • Customer Churn • Revenue Growth • Capital Efficiency • Burn Multiple • Startup Valuation • Seed-Stage Investing • AI Startups • Venture Capital 101

October 2, 202635 min

Zero Churn, 90% Close Rate: The Customer Journey VCs Look For | Paige Soya & Mike Desai (CEO, Truentity Health)

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 infrastructure to provide chronic care programs to their patients. Mike explains how Truentity’s sales process often takes just one or two calls and why he actively disqualifies customers who aren’t ready. He also walks through the 21-day onboarding process and “go live day” that help drive adoption and retention—and shares how he built founder-market fit without a pharmacy background. Paige and Mike discuss the work behind zero churn, why pricing needs to support a hands-on customer experience, and what founders can learn by spending time inside their customers’ businesses. The episode closes with the best advice Mike has received: people buy from people. We dive into Why VCs look closely at the customer journey when evaluating a business How Truentity uses cold calls and converts more than 90% of demos into contract requests Why qualifying customers includes knowing when they aren’t ready Building founder-market fit by starting with a services business The checklists, training, and on-site support behind Truentity’s 21-day go-live process How dedicated Slack channels provide real-time customer support Why pricing and annual contract value need to support the customer experience Why every new hire attends a customer onboarding, regardless of role Mike’s early-morning routine, running, and lessons from working at eight startups Why human connection still matters in sales Chapters 00:00 Intro 00:54 Welcome to High Stakes: VC 101 & the user journey 01:38 Meet Mike Desai & Truentity Health 04:09 Why the user journey matters to VCs 05:00 Cold calling, customer qualification & a short sales cycle 10:39 Building founder-market fit without a pharmacy background 16:58 Onboarding, adoption & zero churn 21:58 Real-time support & the economics of a high-touch experience 24:42 Learning from customers in the field 27:33 Mike’s morning routine & running 29:24 Learning from failure 31:34 Best advice: people buy from people 33:32 Final thoughts Topics: Venture Capital • Customer Journey • Founder-Market Fit • Customer Discovery • Sales • Customer Onboarding • Product Adoption • Customer Retention • Churn • Customer Success • Pricing • Healthcare Technology • Independent Pharmacies • Venture Capital 101

September 17, 202639 min

How VCs Actually Think About Startup Valuations? | Paige Soya, Nick Duafala & K Street Capital

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 what a company is worth today. Investors are also considering what it could be worth at exit, how long it may take to get there, and whether the potential return aligns with the fund’s strategy and portfolio construction. The team walks through valuations at each stage, from pre-seed and seed to Series A and growth, and explains how the criteria evolve. At the earliest stages, the focus is heavily on the founder, vision, and technology. As a company matures, product-market fit, comparable financings, revenue quality, customer diversification, margins, and scalability become increasingly important. Paige and Nick also unpack the terms beyond the headline valuation that can materially affect a deal, including warrants, liquidation preferences, board seats, and pro rata rights. They discuss what “founder-friendly” investing means in practice, how cap tables may be restructured during challenging markets, and what investors learned from the wave of recapitalizations that followed the 2022 market downturn. The conversation then gets granular about revenue multiples: how growth, churn, customer concentration, market size, and revenue quality can move a multiple up or down. The team closes by exploring the “founder premium” earned by proven repeat entrepreneurs, followed by a lightning round on the best advice each person has received. In this episode: How VCs assess startup valuations Why fund strategy and portfolio construction influence valuation What investors evaluate at the pre-seed, seed, Series A, and growth stages Typical valuation ranges across funding stages Why K Street generally doesn’t lead Series A rounds—and how that affects its input on valuation How warrants can lower an effective valuation without changing the headline price How liquidation preferences and payout waterfalls work How board seats and pro rata rights factor into deal terms What “founder-friendly” investing means at K Street Why cap table recapitalizations became more common after the 2022 downturn How investors build revenue multiples from an industry baseline How growth, churn, revenue quality, and customer concentration affect a multiple What qualifies as “high growth” at the seed and Series A stages Why repeat entrepreneurs may command a “founder premium” The best advice each team member has received Topics: Venture Capital • Startup Valuations • Portfolio Construction • Pre-Seed Funding • Seed Funding • Series A • Growth-Stage Investing • Liquidation Preferences • Warrants • Board Seats • Pro Rata Rights • Revenue Multiples • Founder-Friendly Terms • Cap Table Recapitalizations • Customer Concentration • Founder Premium • Venture Capital 101

September 11, 202649 min

What Makes a Business VC-Backable? | Paige Soya, Nick Duafala, & Jon Sherry (Alium, Ex-CB Insights)

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 marketplaces, what constitutes a true platform, and why founders should understand the distinction between a business model and a pricing model. Jonathan also shares how CB Insights and Alium have used subscription models, seat- and capability-based pricing, and marketplace dynamics to monetize their businesses. The group then explores one of the biggest shifts in technology: AI and the rise of usage-based and labor-replacement models. They discuss whether AI will fundamentally change SaaS, why customers increasingly want to experiment before committing to annual contracts, and what founders should understand about consumption, utilization, pricing, and ROI. The episode also examines what VCs look for beyond ARR, including customer concentration, ACVs, renewals, paid POCs, and evidence that a company has built a repeatable business model. Finally, the conversation turns to liquidity in venture capital. With companies remaining private longer and fewer pursuing IPOs, the group discusses M&A, secondary markets, alternative paths to liquidity, and why exits in the $100 million to $250 million range can be compelling outcomes for early-stage investors. In this episode: What makes a business model VC-backable Why SaaS remains a compelling venture business model How marketplaces and platforms create defensibility Why a “platform” is not necessarily a business model How startups can evolve their business models as they grow The emerging “service as software” and labor-replacement model How AI is accelerating the shift toward usage-based pricing The risks and opportunities of consumption-based models Why customers increasingly want to experiment before committing What paid POCs reveal about the quality of a startup’s revenue Why VCs evaluate customer concentration and diversification What a strong seed-stage SaaS customer portfolio can look like Why founders shouldn’t confuse potential revenue with actual ARR How VCs approach liquidity when companies remain private longer The growing role of secondary markets Why $100 million to $250 million exits can be attractive outcomes Jonathan’s biggest lesson from CB Insights: never give up a market lead Why founders must keep moving forward Topics: Venture Capital • VC-Backable Business Models • SaaS • AI Startups • Usage-Based Pricing • Marketplaces • Startup Fundraising • Revenue Quality • ARR • Go-to-Market • Venture Investing • Liquidity • Secondary Markets • Founder Advice

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.

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