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Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Sam Lessin is a Partner at Slow Ventures, where he has backed breakout companies like Robinhood, Airtable, Ro and Solugen. Previously, he was VP of Product at Facebook, where he led core product and identity. He also founded Drop.io, which was acquired by Facebook. ---------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 00:54 TVPI Is Bullshit? 08:06 Mid-Tier VC Funds Are Getting Annihilated 14:55 The Impact of Mega Funds on Startups 24:37 The War on Relevance: What Companies Truly Matter? 38:25 Mary Meeker’s AI Report: What Everyone Missed 40:31 $600B in AI CapEx - Where Is the Revenue?! 53:34 The Existential Dread Missing in Most B2B Startups 01:04:24 IPO Market Is Back: What Actually Matters Now? 01:09:32 YC Startups at $60M Valuations: How Should You Play It? 01:13:34 Why 3% Ownership Could Still Work—Maybe 01:17:39 Kalshi Quick-Fire Round ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Jason Lemkin on X: https://twitter.com/jasonlk Follow Rory O’Driscoll on X: https://twitter.com/rodriscoll Follow Sam Lessin on X: https://twitter.com/lessin Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #samlessin #openai #tesla #ipo #ycombinator #meta #startups #jonyive

Sam LessinguestRory O’DriscollguestHarry StebbingshostJason Lemkinguest
Jun 5, 20251h 27mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Venture returns, AI capex, and relevance in a shifting market landscape

  1. The panel argues that net DPI (cash returned) is the ultimate measure of venture success, while TVPI can be a noisy, often-marketed proxy whose usefulness depends on time horizon and mark quality.
  2. They debate whether mid-sized VC funds are being “hollowed out,” with mega-funds distorting pricing and check sizes, but also note that strong A-to-C investing can still produce meaningful outcomes even outside “generational” companies.
  3. A recurring theme is a “war on relevance,” questioning which companies truly matter in platform shifts and how that worldview influences investing, selling decisions, and founder motivation.
  4. Mary Meeker’s AI data is used to highlight unprecedented AI adoption and a massive infrastructure CapEx wave, alongside uncertainty about when applications and revenue will fully catch up to spending.
  5. For B2B, they emphasize that token-cost deflation and agentic interfaces (e.g., MCP) threaten traditional SaaS UX and moats, making urgency (“existential dread”) and fast product iteration critical to survival.

IDEAS WORTH REMEMBERING

5 ideas

DPI is the scorecard that ultimately matters, but TVPI can carry weak signal early.

They agree LPs “eat” distributions, not paper marks, yet acknowledge TVPI may be a rough proxy in years 2–5 when no cash has returned—especially if marks are credible and consistent.

VC has split into two different businesses: returns-first investing vs asset gathering.

Lessin frames venture as either (1) disciplined investing to return cash or (2) scaling AUM for fees and brand; conflating the two creates confusion about strategy, fund size, and what “success” looks like.

Mid-sized funds aren’t automatically doomed, but mega-funds change the game mechanics.

O’Driscoll pushes back on “no middle,” citing examples where A/B entry still yields strong multiples; however, mega-funds can overpay, inflate round sizes, and force everyone else to adapt to distorted pricing.

Selling is a core skill—don’t sell the rare ‘infinity’ assets, but be ruthless when the thesis breaks.

They stress that early-stage investors get many reps buying but few reps selling; discipline means holding true generational candidates while taking liquidity (including secondaries) when upside is no longer asymmetric or the narrative is frothy.

The ‘companies that matter’ worldview is motivating but can become nihilistic or misleading.

Lessin argues most companies don’t “matter” in a paradigm-shift sense, while Lemkin and O’Driscoll counter that many “non-generational” wins still produce real wealth and can be fund-material—especially with correct pricing and timing.

WORDS WORTH SAVING

5 quotes

Look, from my perspective, this is simple, right? Which is there's two very different games that are called venture capital or even, you know, private capital in general. One game is actually making people money... and that is a DPI game, and all that matters is DPI... There's also an asset gathering game... As a business, the asset gathering game is actually a better business... Uh, the problem is, like, I just am an intellectual snob, and I have no respect for asset gatherers. Like, I think it's a stupid game.

Sam Lessin

You can say, "TVPI means nothing. I'll stick my head up my ass, and I'll look in seven years. I'll see how they're doing." Or you can use TVPI for what it is, a proxy, a loose proxy for performance.

Rory O’Driscoll

Public company investors are just mean VCs on steroids. We turn on a dime from, "I can't believe you're not spending more," to, "What the frick do you mean you're spending so much money?"

Rory O’Driscoll

Every single one of you will cash the fucking check. Every single one of you.

Rory O’Driscoll

The default is, is that most of us don't matter, and most of the companies in the world don't matter. And, but the, but the things that matter really matter, right? And like, I think the job is to find the things that really matter.

Sam Lessin

DPI vs TVPI vs IRR and LP incentivesAsset gathering vs true return generation in VCFund size “death zone” and portfolio constructionSecondaries and when to sell non-“infinity” positionsMega-fund effects on Series A pricing and availabilityAI adoption curves, token cost collapse, and hyperscaler CapExAgentic interfaces/MCP and SaaS becoming “systems of record” behind agentsIPO window reopening, valuation realism, and public-market disciplineChina model competition and AI commoditization riskYC valuation inflation, dilution dynamics, and ownership math

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