The Twenty Minute VC (20VC): January 29, 2026

Episode Overview

This roundtable episode of 20VC, hosted by Harry Stebbings with guests Jason Lemkin and Laurio Driscoll, delivers an energetic, insightful rundown of the week's biggest stories in tech and venture capital. The trio dissect landmark events including the $5.15BN Brex acquisition by Capital One, skyrocketing AI inference costs (with a focus on Anthropic), OpenEvidence's $12BN valuation, the state of the IPO market (EquipmentShare, Wealthfront, Ethos), and a data-filled look at a16z’s dominance in AI.

With sharp analysis, personal anecdotes, and their signature candid banter, the hosts debate who wins and loses in today’s tech market, the implications for founders and investors, and the state of SaaS and AI. The conversation spans celebratory moments, hard questions about late-stage valuations, competitive positioning, the economics of AI, and what these trends mean for both the current landscape and the future of venture capital.

Brex Acquired by Capital One: $5.15BN Deal

Summary

• Deal Details: Brex acquired for $5.15BN (50% cash, 50% shares)
• Themes: Was it a win or disappointment? What does it signal about late-stage valuations and the fintech landscape?

Key Discussion Points

The “Is it a Good Outcome?” Debate

• Harry Stebbings: “You built something from nothing to a $5 billion outcome before you're 30. Heroic result, absolutely be praised. I think it's a smart acquisition for CAP1 too...” [04:56]
• Reactions among the tech community range from praise ("heroic result") to sneers about falling short of Brex's peak $12BN valuation in 2021.

The Problem of Hubristic Financings

• Jason Lemkin: “This is the era I called hubristic financing... you set yourself up for disappointment because these companies... are promising...this 0.1% growth ad infinitum.” [06:17]
• The arms race of raising at sky-high valuations leads to tough feelings when exits reset expectations.

Counterpoints on Fundraising Strategy

• Harry Stebbings: “When you take money at a high price, you run this risk of subsequently exiting at a lower price and having this weird odd feeling for a day. But... you had to raise the money in 21, therefore you did market price at the time. The bad feelings last for a day and the $5 billion lasts forever.” [08:03, 00:00 repeated later]
• Stebbings emphasizes that context matters—companies have to play the hand they’re dealt.

Benchmarking Against the Competition (Ramp, Navan)

• Harry Stebbings: “Ramp, you started later and you're doing a billion. They started earlier, they're doing $700 million. Good news, you've won. But... if you multiply Ramp's {run rate} by 7, you get 7 billion...you think yours is worth 30x...maybe check your assumptions.” [11:52]
• The deal sets comps for private fintechs and raises existential questions about future exits.

What This Means for Capital One

• Harry Stebbings: “Now that they have Brex, they will probably be directing as much of that money flow onto their own rails...they'll be able to extract a lot more of the value.” [15:22]
• CapOne's strategic acquisition—building on their DiscoverCard network—could give them a formidable advantage.

Notable Quotes

• Jason Lemkin: “In 24 months we're going to even forget whether it was two X's or how to spell it...We'll forget. This is our world.” [09:04]
• Harry Stebbings: “Things prove up in the end, for what they really are, not what you delusionally think they are.” [10:03]
• Laurio Driscoll: “How does this change the game for Ramp? ...Does this help or hurt them?” [11:46]

TikTok Deal: U.S. Investors Take Over

Summary

• Deal: US investors own 80% of TikTok US; Chinese parent retains control of the algorithm.
• Themes: Geopolitics drives structure; deal is oddly attractive on revenue multiples.

Key Discussion Points

• The deal is fundamentally political, not economic: “You can't approach this deal economically. It's a political geopolitical decision...” [17:36]
• Extremely attractive for US investors: “15 or 16 billion dollars in the US revenue. They bought it for like one times revenue, plus or minus. That's a wildly cheap deal...” [17:36]
• Why aren't top-tier VCs (a16z, Sequoia) in the deal? Raises questions about hidden structural risks.
• Reminiscences about the Skype deal, which generated huge returns for early backers.

Notable Quotes

• Harry Stebbings: “Most addictive popular application in the United States social media marketplace at one times revenue — put me down for some.” [17:36]
• Jason Lemkin: “There's a reason they're not in that deal. It's free money otherwise. Right?” [19:37]

Anthropic Inference Costs: The Reality of AI’s Economics

Summary

• Headline: Anthropic's inference costs are 23% higher than expected, highlighting questions about AI margins and scalability.

Key Discussion Points

Inference Cost Crisis—Are Economies of Scale Real?

• Jason Lemkin: “Amjad's always been like, no, you're, it's going to, everything's going to get more expensive because as soon as we figure out how to do this stuff, we're going to burn even more tokens...” [20:32]

Margin Trends and the Path to Profitability

• Harry Stebbings: “...last year they had a negative 94% gross margin and this year they have a 40% plus or minus gross margin... there is significant leverage in inference costs and the P&L is getting a lot better. But it may not go all the way...” [21:55]

Challenges for Mid-Scale B2B Companies

• Many SaaS and B2B businesses can’t keep up with cost curves or competition: “I worry... you did all the right things... and the final nail in the coffin is we just can't afford the inference. We just can't build a competitive product.” [29:02]

Competitive Dynamics and Survival

• To survive, companies have to build "epically good" agents that deliver clear ROI—otherwise, outspent by VC-backed or better-funded competitors.

Notable Quotes

• Jason Lemkin: “Your inference costs are a marketing cost. The established players don't have that luxury.” [31:27]
• Harry Stebbings: “The problem of I have infinite demand for this digital good, which is still quite expensive to produce... is a wonderful problem compared to no one wants to buy this digital good.” [25:01]

Compute Demands and the AI Bubble Question

Summary

• Key Point: Massive, still-increasing demand for compute and infrastructure to support AI. TSMC (chip foundry) is raising capex to meet anticipated needs.

Key Discussion Points

• TSMC’s investments seen as the "first step in the AI pyramid"—signal of how core providers view the runway for AI.
• Risk that we are "over-investing at some level" but signs (for at least the next 12–24 months) continue to support current spending.

Notable Quotes

• Harry Stebbings: “If you dig a big deep hole in the ground... and put a fab in there and no one uses it, you're out 20 billion bucks. And they're leaning in right now.” [34:40]
• Jason Lemkin: “There's just, there's no upside in betting this is going to slow in the next 24 months.” [38:15]
• Harry Stebbings: “All you can do is play to the current scenario, but have a plan that if the world changes, you'll know how to change.” [38:15]

OpenEvidence Raises at $12BN Valuation

Summary

• Deal: OpenEvidence raises at $12BN, led by Thrive and DST, up massively from earlier rounds.
• Theme: The ultimate AI vertical SaaS play in healthcare; amazing growth, but is the TAM big enough?

Key Discussion Points

Is This Peak Valuation?

• Harry Stebbings: “It's a great company. It's a perfect use case for AI...they appear to have commanding market share. So the only question is how big is the market?” [39:16]
• Pharmaceutical ad spend is huge, but much is direct-to-consumer, not to doctors. Real direct-to-doctor revenue is smaller—so TAM expansion is necessary.

Hubristic Fundraising Risk Revisited

• Jason Lemkin: “Who does the $12 billion Brex around here, where nothing, nothing but greatness, but gets caught with the tail end of hubristic fundraising?” [42:27]

Founders, Market, and Execution Matter Most

• “This is such an obviously good deal in such an obviously good market with a wildly quality founder…” [43:06]

Notable Quotes

• Laurio Driscoll: “In the moment. It never feels that hubristic. ...12 billion did not seem that crazy.” [44:15]
• Jason Lemkin: “It's so easy to walk into the partners meeting and, and advocate for open evidence, isn't it? ...I propose 1 billion at 35 billion this week. It's a generational company.” [44:38]

a16z (Andreessen Horowitz) Dominance in Private AI

Summary

• Highlight: a16z’s report claims that 2/3 of private AI revenue comes from their portfolio.

Key Discussion Points

• Harry Stebbings: “If you add up all the AI revenue, you're going to get 13 billion for OpenAI, 4 billion for Entropic and everything else is in the noise...Actually, if you were to lump a third one in, it would be Databricks, which they have a massive market share in.” [46:03]
• Raises questions about venture capital as an asset class and whether it can/should absorb more capital if leading platforms dominate.
• Venture now functions as "two asset classes"—traditional early stage and new later-stage “private small cap growth” businesses.

Notable Quotes

• Harry Stebbings: “Most of the time we sit around here waiting, reading and thinking and I thought that's a real investor.” [50:41]
• Jason Lemkin: “If Andreessen has proven this penetration and AUM is repeatable ... Is Venture finally an asset class?” [46:50]

Succession in VC: Can a16z (and similar firms) Survive Generational Transitions?

Key Points

• Discussion about founder-led, branded VC firms (a16z, Khosla) facing inevitable leadership transitions.
• Conclusion: The real test is if these firms can transcend the founders and professionalize like modern investment banks.

Notable Quotes

• Harry Stebbings: “The graveyards are full of those indispensable men. ...Firms that proactively manage succession planning can make it happen.” [51:40]
• Jason Lemkin: “Can it survive at this elite level, a generational transition, Right? ...And I'm not sure.” [53:26]

IPO Market Update: EquipmentShare, Wealthfront, Ethos

EquipmentShare

• IPO: Pop of 33%, $8BN market cap, 47% growth.
• Summary: “It's a good ipo. Points to the need for scale, profitability...They seem to have built—in large part using digital technology—a pretty compelling business.” [55:04]

Wealthfront

• Contrast: IPO is “deeply broken,” stock trading down 30-40% from IPO, “subscale.”
• Debate: What does this mean for liquidity, talent attraction, and public company status?

Ethos Insurance

• Issue: Going public at $1.3BN, peak private value was $2.7BN—should subscale companies stay private?
• Conclusion: Startups must meet public market standards for growth and scale. Market will "clear at a price," even if it's not what late-stage investors hoped for.
• “To start a company from nothing and get to one or two billion dollars in value, get it public, have the chance to compound for five or ten years. It's an awesome achievement.” [65:20]

Notable Quotes

• Jason Lemkin: “If you're at billions in revenue, growing 47% and profitable...then you can IPO in an effortless fashion. I view this as an effortless IPO...” [56:02]
• Harry Stebbings: “It's the low end of the public company market cap, but it's a perfectly good outcome. And to be congratulated...” [65:20]

SaaS Is Not Dead: Salesforce and the AI Zeitgeist

Key Points

• Big Win: Salesforce wins $5.6BN, 10-year Army contract.
• Meaning: Strong endorsement for SaaS (systems of record), showing that AI-enhanced incumbents are far from dead.
• “The correct pushback has been ... all these systems of record like Salesforce are going to get replaced are obviously wrong...” [68:08]

Challenges for SaaS

• Shrinking seats, price increase fatigue, multiple headwinds.
• SaaS will adapt, but “magically charging per token doesn't necessarily change the fact for many providers...” [71:41]

Notable Quotes

• Harry Stebbings: “SaaS is not dead. And now SaaS has an army. I love it.” [68:01]
• Jason Lemkin: “You got to have these epic leaders and ICs to compete today.” [61:43]

Closing Reflections

• Venture and tech outcomes are power law distributed—most value accrues to few companies.
• Market pragmatism, scenario planning, and value creation remain the most important virtues for both operators and investors.

Memorable Quotes & Timestamps

• “The bad feelings last for a day and the $5 billion lasts forever.” — Harry Stebbings [00:00, 08:03]
• “You set yourself up for disappointment because these companies...are promising...this 0.1% growth ad infinitum.” — Jason Lemkin [06:17]
• “Most of the time we sit around here waiting, reading and thinking and I thought that's a real investor.” — Harry Stebbings [50:41]
• “SaaS is not dead. And now SaaS has an army. I love it.” — Harry Stebbings [68:01]

Key Timestamps for Segment Reference

• Brex Acquisition Deep Dive: 04:28 – 17:19
• TikTok US Deal: 17:19 – 20:20
• Anthropic & AI Inference Costs: 20:20 – 34:40
• OpenEvidence AI Round: 38:42 – 45:22
• A16z/VC Market Dominance & Asset Class: 45:22 – 53:46
• IPO Market (EquipmentShare, Wealthfront, Ethos): 54:48 – 66:46
• SaaS, Salesforce, and the AI Narrative: 67:42 – 72:17

Final Thoughts

An episode packed with substance—critical analysis, optimism for bold founders, warnings about capital cycles, and a clear-eyed look at what it takes to win in today's venture arena. The hosts strike a balance between celebratory moments and cautionary tales, all delivered with wit and wisdom for anyone navigating the world of tech startups and investment. This is an essential listen (or read) for founders, VCs, and tech observers seeking to understand where the market is and where it’s headed.