High Stakes

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

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

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

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

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