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 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

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

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

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

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