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Insight
Founders should eliminate Customer Success and hire technical sales engineers
“Yes. Get rid of them. Build a professional service organization. Hire more SEs who can do it. Customer success. Look, people think that's blasphemy. I get it. I don't believe in it. I inherited our customer success when Frank came in and he gave it to me. I go…”
Chris Degnan Nov 10, 2023 ▶ 48:13 Chris Degnan: Why You Should Hire a Head of Sales Sooner Than You Think | E1080 · 20VC with Harry Stebbings
Insight
Expert: Superintelligence does not imply a desire to dominate humans
“There is this idea, somehow, the desire to, and the ability to dominate, is linked with intelligence. A statement that a lot of people are making, including Jeff Hinton recently, That somehow, as soon as a machine becomes intelligent, it becomes uncontrollable…”
Yann LeCun Jun 2, 2023 ▶ 18:49 20VC: Who Wins the AI Race; Startups or Incumbents & Does Having Proprietary Data Really Matter For Startups Today?
Insight
O'Driscoll: Displacing Overeducated Young Elites Triggers Major Political Instability
“You can have dispossessed urban poor forever, and nothing happens, but if you piss off the twenty-something-year-old middle class, the overeducated elites, they tend to cause trouble.”
Rory O'Driscoll Mar 12, 2026 ▶ 0:38 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Insight
Chang: Employees are underperforming if a gun to the head yields more
“If you have a gun pointed to your head today, would you have done more? If the answer is yes, that means you're not doing a good job.”
Alan Chang Jan 5, 2026 ▶ 8:27 Fuse CEO Alan Chang: The Revolut Playbook of Speed & Ownership, Why Founders Aren’t Ambitious Enough · 20VC with Harry Stebbings
Insight
Lemkin: Fire half your team if AI hasn't reaccelerated growth
“If you haven't gotten a boost this year from AI, fire half your team right before the holidays, give them a turkey and three months of severance, but they failed. You have a, your team is not good enough. They had 18 months to ship a product that mattered in t…”
Jason Lemkin Nov 6, 2025 ▶ 58:06 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Insight
$7B Multi-Stage VC Funds Require $800B in Exit Cap for 4x Net
“You're close to, you know, eight hundred billion of market cap needed to return a Forex net for those multi-stage funds. Now, for reference, twenty-twenty-one, the best exit year of all time, there was 850 billion-ish of market cap exit value from that year. O…”
Miles Dieffenbach Aug 4, 2025 ▶ 38:34 Miles Dieffenbach: Inside Carnegie Mellon’s $4BN Endowment & The Math Behind DPI, TVPI, Illiquidity · 20VC with Harry Stebbings
Insight
Lemkin Advises CEOs to Mandate RTO and Fire Non-S-Tier Engineers
“The only advice I gave to this particular CEO is immediate, like he was hybrid. So I said to force a hundred percent of people returned to office in 30 days and let everyone go, except your S tier engineers, letting them all go. Because you don't need them.”
Jason Lemkin May 15, 2025 ▶ 42:40 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Insight
Hulme: AGI hype correlates directly with founders' capital fundraising needs
“I think there is a Correlation between how aggressively people predict AGI is coming and how much capital they need to raise. So you've got Emodi from Anthropic, you've got Altman, OpenAI, Musk, XAI, all of these guys are saying that it's just around the corne…”
Tom Hulme May 8, 2024 ▶ 1:11:38 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
Insight
Tobi Lütke: Study World of Warcraft guilds over corporations for organizational mastery
“I think you can learn more by studying World of Warcraft raiding guilds than you can learn from studying companies about coordination and what great looks like.”
Tobi Lütke Apr 3, 2023 ▶ 1:20:47 Shopify CEO Tobi Lütke: Remote Work vs In-Person; The Benefit of Setting Constraints | E997 · 20VC with Harry Stebbings
Insight
Gerstner: LPs should mark down 2020-2022 late-stage venture portfolios by 50%
“I said, I would take everything in your portfolio that received a valuation over the last two years, over five hundred million dollars, and I'd mark it down by 50%. What do you mean? And I said, well, if I look at the average gross stock in the NASDAQ, it's do…”
Brad Gerstner Oct 10, 2022 ▶ 39:23 Brad Gerstner: How I Pick Companies; Lessons from Warren Buffet; Chamath vs Gurley | E935 · 20VC with Harry Stebbings
Insight
Sacca argues sunlight reflection research is essential to avoid climate catastrophe
“And so the one thing we absolutely have to do is research sunlight reflection. And so we have no way out of this without reflecting sunlight back into the solar system to buy us some time.”
Chris Sacca Oct 11, 2021 ▶ 1:12:11 20VC: Chris Sacca on Coming Out of Retirement To Unf**k The Planet with Lowercarbon, How Chris Evaluates His Relationship To Money Today, Why We Have Bred a Generation of Ass**** Kids, Do VCs Provide Any Real Value and The True Unfiltered Opinion on Faceb
Insight
Midha: Top VC investors should be forced to retire to protect decision-making
“Venture capital is a business about outliers, and when somebody succeeds, their opinion, and I think their decision-making gets over-indexed on their successes, which often, as you know, are outliers, and it's hard to generalize from a single outlier, and my b…”
Anjney Midha Feb 8, 2019 ▶ 15:31 20VC: What Makes The Best Venture Firms Today So Special, The 3 Structural Impediments That Face Venture Today and Why The Debate on AR vs VR is BS with Anjney Midha, Founder & CEO @ Ubiquity6
Insight
Mir: Early-stage startups should avoid diversity of thought in favor of alignment
“But what we don't want, which I think is not commonly supported by other early stage startups is what we don't really want at this stage is diversity of thoughts, and I know that doesn't make sense. It's a little counterintuitive, but the reason why we don't i…”
Ari Mir Jun 30, 2017 ▶ 13:31 20VC: Why You Do Not Want Diversity Of Thought, Why You Have To Build A Sports Team and Not A Family & Why Extreme Cultures Are Easier For People To Understand with Ari Mir, Founder @ Clutter
Insight
Rachleff: 90% of a VC's value creation comes purely from stock selection
“90% of the value added of a venture capitalist is finding and choosing the right investments.”
Andy Rachleff Jun 20, 2016 ▶ 11:58 20VC: Andy Rachleff, Founder @ Benchmark & Wealthfront on What Makes The Best CEO & Board Member & Why Ivy League Endowments Are The Best Managed Capital In The World
Insight
Lemkin: A $9B exit is not enough for seed investing in 2026
“Nine billion doesn't clear the bar for seed investing in 2026.”
Jason Lemkin Aug 27, 2026 ▶ 8:30 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Insight
Lemkin: Dev teams not working on 2027 roadmaps by August 2026 cannot survive
“If no, if you're not into your 20, 27 roadmap deep into it by August of 20, 26 in the agentic world, your team is not good enough to survive today.”
Jason Lemkin Aug 20, 2026 ▶ 40:56 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Insight
E-commerce performance playbooks are the correct B2B SaaS growth strategy
“My philosophy is that the Ecom playbook Is the right playbook for SAS? Because if you look at e-comm, you have every single cent needs to equal a purchase or an ad to cart. You have hundreds of UGC creators, variety of creative, and you also have a ton of chan…”
Matt Swulinski Aug 14, 2026 ▶ 3:23 How to Build a $100M Growth Engine: Lessons from Wispr Flow & Superhuman | Matt Swulinski
Insight
Swulinski: Fire marketing team members who are not systems thinkers
“My hot take was probably fire most of your marketing team that is not a systems thinker. Like, stop brute forcing people in. Hire the right people into the roles because the role has changed.”
Matt Swulinski Aug 14, 2026 ▶ 1:05:58 How to Build a $100M Growth Engine: Lessons from Wispr Flow & Superhuman | Matt Swulinski
Insight
Angelopoulos: Chinese AI Progress Involves More Than Distilling US Models
“That doesn't mean that they're not distilling. They may still be using distillation as a sub-step in their training procedure, But it does mean that distillation is only part of the story and that there's something that those labs are doing above and beyond di…”
Anastasios Angelopoulos Aug 2, 2026 ▶ 4:10 Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
Insight
O'Driscoll: Open-weights models do not have open-source software's security benefits
“The reality is when you're getting open weights, you're not getting, it's not the same thing because all you get is the fixed weights that allow you to run the model. What you don't know is the black box inside those weights and how they work.”
Rory O'Driscoll Jul 29, 2026 ▶ 27:34 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Insight
Small stakes in massive outliers beat high ownership in mid-sized exits
“You have to be in the big outliers to drive great returns, and you're better off being in them at a very small percent than owning a large percent of a company that exits for three to 500. Those just aren't going to move the needle.”
Matt Murphy Jul 27, 2026 ▶ 8:09 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
Insight
O'Driscoll: Major Startup Breakthroughs Rely on Boundary Pushing Legalized Upon Success
“So many breakthroughs rely on a little bit of pushing the boundaries. I mean, Uber did with taxi regulation. Airbnb did with regulation. You're right. Polymarket did in terms of how they're regulated. So I'm actually going to get off my high horse and say you …”
Rory O'Driscoll Jul 16, 2026 ▶ 59:52 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Insight
Jain: AI-amplified companies producing 10x output will beat those shrinking headcount
“If you were trying to do the same amount of work and you believe you can do it with fewer people and therefore you shrink your competition can also do the same, but they chose actually not to do the same amount of work. They chose to actually, you know, elevat…”
Arvind Jain Jul 11, 2026 ▶ 30:12 ⁠Why OpenAI and Anthropic Won't Win the App Layer | Glean Founder · 20VC with Harry Stebbings
Insight
Mignano: Fred Wilson's key VC lesson is to never pass on price
“I asked him, what are a couple of the biggest lessons? And one of them was, never pass on price. So Fred says, never pass on price.”
Mike Mignano Jul 6, 2026 ▶ 48:31 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
Insight
Lemkin: Autonomous AI agents could reduce Salesforce and HubSpot to dumb databases
“If the agent can run 24 seven autonomously, take all your data and build all the analytics, build all the dashboards, run autonomously out of it then your data can flow between apps and you won't even care where it lives and all the fears about headless become…”
Jason Lemkin Jul 2, 2026 ▶ 1:12:27 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Insight
Lemkin: LLM-driven migration tools are destroying traditional B2B software moats
“It's a moat destroyer when LLMs will lift you from one vendor to the other, and I, you know, I don't even, like, I literally was doing a pitch this week, and the founder was going on and on about their moats, and I immediately didn't want to invest. Like, I ju…”
Jason Lemkin Jun 25, 2026 ▶ 1:10:00 DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
Insight
Petersen: Work-from-home ultimately benefits employers through global labor arbitrage
“The idea that work from home is going to benefit highly paid employees is sort of a total fantasy. Like, work from home done correctly, you should be hiring the world's greatest geniuses. There should be a labor arbitrage here, where you're finding really, rea…”
Ryan Petersen Jun 20, 2026 ▶ 39:21 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Insight
Grinberg: Believing a good product sells itself is delusional
“There's a very common Silicon Valley fallacy, which is there's like research is like the pinnacle. And then there's engineers who implement the research, you know, they're not quite there, but you know, they're still great. And then there's sales and marketing…”
Matan Grinberg Jun 13, 2026 ▶ 25:13 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Institutional Math Olympiad track records can be an anti-signal in hiring
“Especially there's some high schools that, like, really focus on, like, you must do the math olympic, like, you must do this, the Amy, to then go to the IMO, and, like, this is the path to success, where actually that's kind of anti-signal, because there it's,…”
Matan Grinberg Jun 13, 2026 ▶ 29:56 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Grinberg: Software requiring forward-deployed engineers to close deals is a bad product
“If we need FDEs to make the product work, we have a shit product. Like, the point of FDEs should be accelerate and get them consuming faster. If you're putting in FDEs, because that's the only way you'll get a deal done, I'm sorry, my friend, you have a shit p…”
Matan Grinberg Jun 13, 2026 ▶ 1:15:15 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Insight
Laqua: Demanding seven-day workweeks filters for the right hires
“And if you want to win, then actually it's something that I think attracts the right type of person and absolutely repels the wrong type of person.”
Nico Laqua May 30, 2026 ▶ 9:03 The Hardest Working Startup in America | Nico Laqua, Co-founder & CEO @ Corgi · 20VC with Harry Stebbings
Insight
Laqua: Startups must hire more non-engineers to compensate for lower intensity
“So naturally there, there's roles, I think that, that creep in, you know, you get the, like a lawyer and accountant are not going to work in the same way that you know, a software engineer might. And that's just a fact of life. So, okay. So if they don't want …”
Nico Laqua May 30, 2026 ▶ 29:15 The Hardest Working Startup in America | Nico Laqua, Co-founder & CEO @ Corgi · 20VC with Harry Stebbings
Insight
Lemkin: In AI Venture, Seed Investing Is for Suckers
“And I just think this going back to seed is for suckers. Like you want to invest the hour it blows up. The minute it blows up, you want to get the DM and just wire the money in AI. That's the play.”
Jason Lemkin May 28, 2026 ▶ 1:14:23 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
Insight
Peets: Healthy Sales Orgs Must Attrit Bottom 10% Annually
“Every, every healthy sales organization should be attrating the bottom 10% every year. You should be getting rid of 10% of your sales force every year.”
Chad Peets May 23, 2026 ▶ 1:14:17 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
Insight
Browder: Accept Sequoia or Founders Fund Over Double Valuation Term Sheets
“There's like the kingmaker firms that you should accept at any price. One example would be Founders Fund or Sequoia or people like that. And so if you get an offer from them at X and the offer from someone else is at two X, you should take their offer because …”
Josh Browder May 18, 2026 ▶ 49:42 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
Insight
Consumer-only healthcare startups rely on untrustworthy data-selling models
“The companies that you can build on top of just the consumer and healthcare, Oftentimes there's the kind of companies that, that paint themselves into a corner that can never be trustworthy enough to go enterprise. They're the kind of companies where the busin…”
Shiv Rao May 16, 2026 ▶ 32:30 The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings
Insight
Lemkin: Fireside chats and speakers are dead at tech conferences
“So I'll have to see, but we won't do, we'll never do Unless I'm forced to, I mean, if, you know, I do it for Sam Altman, but otherwise I'm not gonna do, there's, the firesides are dead and speakers are dead. There's just no point when podcasts are better.”
Jason Lemkin May 14, 2026 ▶ 1:06:02 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Insight
Lemkin: VCs never make real money investing in 'nice' founders
“Yeah, and every time you cut a corner, every time you invest in a founder that's really nice and really hardworking and really good guy, you never make any real money.”
Jason Lemkin May 14, 2026 ▶ 1:15:10 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Insight
Weitzman: Cutting Costs Is Easy, Growing Revenue Takes Genius
“Any Harvard MBA can cut costs. If you're smart, you could do it. It takes a genius to grow revenue.”
Cliff Weitzman May 9, 2026 ▶ 12:30 Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries · 20VC with Harry Stebbings
Insight
Weitzman: Team Leaders Should Be Their Team's Strongest Individual Contributor
“Like you should be the strongest individual contributor in your team if you're leading that team. If you need a people manager, we'll give you a people manager to manage the communication. But I want you mainly hands on keyboard coding, designing, talking to u…”
Cliff Weitzman May 9, 2026 ▶ 1:10:48 Cliff Weitzman: What I Learned from 100 of the World’s Top CEOs & Why Tokens Will Outspend Salaries · 20VC with Harry Stebbings
Insight
Lemkin: Modern CMOs should run marketing campaigns directly using AI agents
“A CMO today should be able to run their own campaigns, and this is why. I'm not saying you have to spin up Marketo or HubSpot. I'm saying you should be able to tell your agent, and our agent, our AIVP marketing started running its own campaigns the last two we…”
Jason Lemkin May 7, 2026 ▶ 1:32:07 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
Insight
Tobi Lütke: Non-profits attract smooth talkers rather than true builders
“It replaces merit of organization with pull of individuals. Who is attracted to these places? The people who want to do something that for which you have to use You know, pull. And you know, the smoothest talkers, the people who, it's not the builders who are …”
Tobi Lütke May 4, 2026 ▶ 36:31 Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada · 20VC with Harry Stebbings
Insight
Lindquist biases toward hiring former college athletes for sales roles
“And like, obviously I bias towards having college athletes because they've learned how to work hard. All you gotta do is teach them how to work smart. If you teach them how to work smart, it's really tough to teach someone how to work hard.”
Becca Lindquist May 2, 2026 ▶ 19:53 Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
Insight
Lindquist: Outbound sales will never be dead
“Outbound will never be dead. You can't reach every single company and every single buyer with whatever marketing you're doing.”
Becca Lindquist May 2, 2026 ▶ 53:20 Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
Insight
Lindquist: Downsizing SDR teams after adopting AI is a scared defensive play
“Anybody that's like, oh, well, you know, we're just going to cut our SDR team in half, I'm like okay. That's an interesting move, right? That's a scared play that you're making because you're saying I can get the same productivity for half versus saying I can …”
Becca Lindquist May 2, 2026 ▶ 58:18 Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
Insight
Adam Foroughi: Lay Off Teams Slow to Adopt AI and Rebuild
“And the reason I did that then is a belief that if the role was going to get automated, Or that AI was not being adopted fast enough in those departments. It's time to let those people go and rebuild the organization as if we were building it knowing what tech…”
Adam Foroughi Apr 27, 2026 ▶ 15:22 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
Insight
Adam Foroughi: Fixing a Bloated Company Requires Firing 99% of Staff
“The only way to fix a culture like that is to go and fire 99% of people and just rebuild it from the ground up.”
Adam Foroughi Apr 27, 2026 ▶ 24:10 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
Insight
Adam Foroughi: Getting Drunk With Coworkers Often Produces the Best Ideas
“The other thing I found is when we go out and we drink and we start shooting the shit, really good ideas can come of that too. It's not that we're going out and with a bunch of coworkers and talking about baseball. We're going out with a bunch of coworkers and…”
Adam Foroughi Apr 27, 2026 ▶ 39:31 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
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