High Stakes

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1. How VCs Think About PR for Startups | Paige Soya & Kate Meissner (Velocity Partners)

   5 november 2026 · 44 min

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   In this episode of High Stakes, K Street Capital Managing Partner Paige Soya continues the Venture Capital 101 season with a conversation about public relations (PR) for early-stage companies: when startups should invest in PR, how founders can build a compelling company narrative, and why the right media strategy can help accelerate business growth. Lees meer

   She's joined by Kate Meissner, K Street investor and co-founder of Velocity Partners, a strategic communications firm working with venture-backed startups. Kate breaks down how founders should approach PR with limited resources, why publicity needs to start with clear business objectives, and how companies can identify the right moment to share their story with a broader audience.

   Paige and Kate explore how founders can develop a narrative that resonates with investors, customers, employees, and journalists. They discuss what makes a story newsworthy, why reporters prioritize their readers over the companies they're covering, and how founders can build relationships with journalists before their biggest announcements.

   The conversation also covers how AI is changing the media landscape, the rise of generative engine optimization (GEO), and why human relationships, credibility, and authentic communication may become even more valuable as more content becomes machine-generated. The episode closes with Kate's career journey, lessons from balancing entrepreneurship and family, and why founders should be selective about whose advice they follow.

   We dive into

   What PR means for early-stage startups and why it matters

   How founders should approach PR with limited resources

   Why publicity should start with clear business objectives

   When startups are ready to invest in PR and media exposure

   How founders can identify a compelling company narrative

   Why finding product-market fit can be a signal to amplify your story

   How PR can support fundraising, hiring, and customer acquisition

   How strategic product announcements can bu…

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

   15 oktober 2026 · 43 min

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   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. Lees meer

   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 pr…

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

   2 oktober 2026 · 35 min

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   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. Lees meer

   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 qualific…

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

   17 september 2026 · 39 min

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   What actually determines what a startup is worth? Lees meer

   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

   W…

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

   11 september 2026 · 49 min

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   What makes a business venture-backable? Lees meer

   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 opportuni…

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

   20 augustus 2026 · 42 min

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   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. Lees meer

   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 ta…

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

   6 augustus 2026 · 46 min

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   What actually creates a competitive moat? Lees meer

   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

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

   23 juli 2026 · 52 min

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   Not all venture deals are created equal, and understanding the fine print can make a significant difference for founders. Lees meer

   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

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

   9 juli 2026 · 35 min

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   What makes a pre-revenue startup worth investing in? Lees meer

   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 i…

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

    25 juni 2026 · 36 min

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    How do venture capital firms actually exit their investments when startups are staying private longer than ever before? Lees meer

    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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