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Disclosure
Weitzman: Speechify now prioritizes raw intelligence over handcrafted coding ability
“So one thing that we have changed about our hiring in the last even six months Is we really cared that you read a ton of textbooks about software engineering and that your handcrafted code was amazing. I still care that you read a lot of textbooks about softwa…”
Cliff Weitzman Sep 5, 2026 ▶ 33:29 How to Build Your Own Data Center & Why Every Startup Should Do It
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Maguire Pushed Sequoia's SpaceX Investment After Partner Voted '1' in IC
“Credits to Sean when he brought in the SpaceX investment, We vote on companies. I think someone voted a one. Yeah. I've seen fours, of course. I've seen threes. Never seen a two. I didn't even know we could do one. I didn't even know it was on the scale. But w…”
Julien Bek Aug 24, 2026 ▶ 17:49 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
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Bek: Sequoia will not back legacy services companies pivoting to AI
“I will not invest in one of those companies. For the following reason. I think you can make money in that business. The reality is I've only seen it in my career. The best companies are able to concentrate talent and you just not going to get frontier talent w…”
Julien Bek Aug 24, 2026 ▶ 1:14:38 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
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Mac: Uber refuses API access to third-party price-comparison aggregators
“We've not participated historically in the aggregation apps where some, you know, somebody will come to us and pitch and say, hey, you know, give us APIs that give us real-time info on Every car, every Uber car in the network what the price of that ride is, wh…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 48:58 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
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Lemkin's team churned off Canva and Notion due to AI agents
“My, me having churned, and Amelia having churned, we churned just not because, this is a tough one, Canva and Notion, both we churned, not because they're not great apps, we just no longer had any need for them in the agentic area, just no need. Canva and Noti…”
Jason Lemkin Aug 12, 2026 ▶ 4:33 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
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Stebbings: 20VC Lost Hundreds of Millions Passing on Deel Over Ownership Targets
“I look at ours, and our biggest mistake, and I can look at Deal, 11 Labs, I can look at Granola, and Starcloud, Fractile, could have done them all, but would have had one to two percent, and all of them we turned down purely for ownership, and that is hundreds…”
Harry Stebbings Aug 7, 2026 ▶ 28:56 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
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Menlo Ventures' Anthropic position is worth over $10 billion
“No, our position is, is north of that, but that's not that you can do the math on what carry usually is.”
Matt Murphy Jul 27, 2026 ▶ 55:02 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
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Nitski: Mercor shifts to senior hires as AI obsoletes junior skills
“We've biased towards more senior hires. Who are better at understanding what drives the business forward, finding, kind of, like, really crocking how we operate, how we make more revenue, how we deliver better services to our customers, how we keep our custome…”
Osvald Nitski Jul 25, 2026 ▶ 22:32 Mercor Head of Product on Revenue Concentration from Frontier Labs
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Nitski: Mercor's fix for lab concentration is moving down market
“I can answer this from kind of like a, how it affects the product team. We would love to move like our biggest challenge is moving down market so that every single enterprise can efficiently run human data projects for eval and training. And that'll diversify …”
Osvald Nitski Jul 25, 2026 ▶ 38:20 Mercor Head of Product on Revenue Concentration from Frontier Labs
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Curative Invested $500M Of COVID Testing Profits Into Health Insurance
“So after all was said and done, the money that we basically put forward into the insurance business, the health insurance company, was about five hundred million that we invested into the health insurance business.”
Fred Turner Jul 18, 2026 ▶ 33:24 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
Disclosure
Curative Administered 2.5M COVID Vaccines At A Loss
“We did two and a half million vaccinations. That was another service we did. We also lost a ton of money on that. That was a terrible business.”
Fred Turner Jul 18, 2026 ▶ 34:14 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
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Curative's Anthropic API Spend Grew 6x Monthly Into Millions
“Our anthropic cost over the last six or seven months has six X'd every month from, you know, a base of, you know, a couple of tens of thousands of dollars now up to millions of dollars a month.”
Fred Turner Jul 18, 2026 ▶ 51:17 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
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Curative's AI Agent Signs Hundreds Of Contracts Daily Without Human Review
“We had a contract, a standard template contract that was drafted by a law firm, and then we have kind of like guard rails for what Gwen can agree to, but she just red lines it and then signs it. It doesn't go to a law firm for a review. Like, we're signing hun…”
Fred Turner Jul 18, 2026 ▶ 59:44 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
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AI Agent Gwen Cuts Curative's Contract Costs From $2,000 To $70
“So it costs, with people, it costs us about 1500 to 2000 dollars on average to do a contract. The average with Gwen has been about 70 dollars.”
Fred Turner Jul 18, 2026 ▶ 55:51 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
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Abrahami: Off-the-Shelf AI Customer Support Tools Do Not Work
“We actually tried not to build our own. You know, we tried, we tested many different things. It doesn't work.”
Avishai Abrahami Jul 13, 2026 ▶ 36:01 Wix Founder: Will Base44 Win the Vibe-Coding Wars? | The Truth About the Economics of Vibe-Coding · 20VC with Harry Stebbings
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Jain: Glean's triage agent handles 95% of issues at an absurd $1M a month
“I would say it's absurdly expensive. I'll give you an example. We had this, we have a really cool triage agent for engineering. You know, and we have 15 people team on call team that was supposed to, that their work was to actually triage Every single producti…”
Arvind Jain Jul 11, 2026 ▶ 33:26 ⁠Why OpenAI and Anthropic Won't Win the App Layer | Glean Founder · 20VC with Harry Stebbings
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Mignano: USV avoids enterprise investing to focus on market obliteration
“At USV, we like to bet on businesses that obliterate, that literally obliterate markets and existing business models. And so, you know, we're, we actually don't do a lot of enterprise investing for this exact reason.”
Mike Mignano Jul 6, 2026 ▶ 32:50 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
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Sierra deliberately took lower valuations than offered in every funding round
“Every one of our rounds, we actually guided to and took a lower price than we could have.”
Clay Bavor Jul 4, 2026 ▶ 0:36 Open Models vs Frontier Models: Who Actually Wins? | The $100K Token Budget Every Engineer Will Need · 20VC with Harry Stebbings
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FOMO Holds More Cash in Bank Than Total Capital Raised
“Our team is scaling. I mean, we're making money. We have much more money in the bank than we ever raised.”
Paul Erlang Jun 27, 2026 ▶ 42:13 How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong · 20VC with Harry Stebbings
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Petersen: SoftBank led Flexport's $1B round and urged undercutting rivals by 10%
“Yeah, well, they led the round of a billion, yeah. And he was like, whatever the price of freight is, you'd just be 10% cheaper than everybody, and then if someone matches you, you'd just be 10% cheaper than that, which is like a terrible strategy. I did not d…”
Ryan Petersen Jun 20, 2026 ▶ 1:12:18 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
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Randle: Benchmark partner says any pre-AI SaaS liquidity is top-decile performance
“There's a partner here at Benchmark that says any liquidity for pre-AI SaaS companies is top decile performance. Any liquidity at all.”
Everett Randle Jun 18, 2026 ▶ 51:12 Anthropic's Fable Banned by US Government | Wix & Adobe Hit All-Time Lows | Mistral Raising at $20BN · 20VC with Harry Stebbings
Disclosure
Mercor spends more on AI agent tokens than employee headcount
“Right now, we're spending more on tokens for our internal agents than we are on employee headcount.”
Brendan Foody Jun 1, 2026 ▶ 43:06 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
Disclosure
Mercor Attacker Used Swarm of AI Coding Agents to Breach Systems
“Because in our incident, it was the attacker that used a swarm of coding agents to help get access to the system as is happening in a lot of these.”
Brendan Foody Jun 1, 2026 ▶ 6:10 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
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Meta Paused Mercor Relationship After Hack While Other Labs Expanded
“I mean, I think that Meta you know, like, currently the relationship is still paused. Every other one of the Frontier Labs has grown their relationship with us since and the company has been crushing it but they're the only one that is paused, which is public.”
Brendan Foody Jun 1, 2026 ▶ 7:50 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
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Foody Rejects $30B Sale Despite Receiving Significant Acquisition Interest
“No, I wouldn't. I mean, ultimately we've gotten a lot of acquisition interest and we could walk away with, like I could walk away with billions of dollars in cash.”
Brendan Foody Jun 1, 2026 ▶ 10:27 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
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Foody discloses Mercor holds over $500M in cash and is highly profitable
“And so we view having over five hundred million in cash and a super profitable business as a significant asset and allowing us to be prepared for when there is a market correction to make sure that we consolidate market share.”
Brendan Foody Jun 1, 2026 ▶ 20:44 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
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Laqua: Corgi Insurance never accepts the highest valuation offered in fundraising
“So we never take the highest price ever. I think that that's just a good rule of thumb. Like we always go with like the second or third highest price.”
Nico Laqua May 30, 2026 ▶ 38:05 The Hardest Working Startup in America | Nico Laqua, Co-founder & CEO @ Corgi · 20VC with Harry Stebbings
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Lemkin: My Team Does With 2.5 People What Used to Require 20
“I mean, we've gone not to be a broken record we're doing with two and a half people. We're doing what we did with 20 and everyone's get paid more on my little team, right?”
Jason Lemkin May 28, 2026 ▶ 29:18 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
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Degnan: Avoids hiring sales reps from the cybersecurity sector
“So I actually have an affinity of not hiring. People out of the security space.”
Chris Degnan May 23, 2026 ▶ 8:04 Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
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O'Driscoll: Passed on seed GPU capacity deal fearing CapEx boom cycle
“I did, to answer the question, Jason, logically, I chickened out. I didn't want to be that marginal capacity three years into the deal, three years into the CapEx boom, but there's a little part of me thinking, Rory, that might be a dumb decision.”
Rory O'Driscoll May 21, 2026 ▶ 45:39 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
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Browder requires pre-seed founders to live with him until raising seed
“It's in California, so it's like Hotel California, where you can't check out until you've raised your institutional seed, and then I, the company is off life support, and I can, like, relax a bit.”
Josh Browder May 18, 2026 ▶ 10:45 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
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Browder: Micro1 is his best-performing investment at over 1,000x return
“Ali Ansari is a micro one, is objectively my best performing investment in terms of multiple. The founders get upset when I reveal exact valuation numbers, but let's say over a thousand X, well over a thousand X and based on the kind of the scale of the busine…”
Josh Browder May 18, 2026 ▶ 43:17 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
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Browder invests all personal earnings into land instead of stocks or cash
“In terms of like my diversification retirement I take all the money I make and I buy land. I don't put it in the stock market. I don't buy, I don't keep it in cash because I think that the dollar is, it doesn't have a good future. I don't buy bonds or anything…”
Josh Browder May 18, 2026 ▶ 1:09:28 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
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Browder: FTC blocked acquisitions of several portfolio companies
“Several companies I invested in had the acquisitions blocked by the kind of Lena Kahn style approach.”
Josh Browder May 18, 2026 ▶ 1:12:29 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
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An Abridge investor required Shiv Rao to undergo a psychological assessment
“We were talking about psychological assessments, I think, before we started, and how some VCs will do that, and I had one before we took money from one of our investors”
Shiv Rao May 16, 2026 ▶ 52:10 The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings
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Harry Stebbings exits investments the minute founders step down as CEO
“The minute the founder transitions out of CEO role, I'm out.”
Harry Stebbings May 16, 2026 ▶ 53:09 The Five Year Desert to Product Market Fit & a $5.3BN Valuation with Shiv Rao, Founder @ Abridge · 20VC with Harry Stebbings
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Legora CRO: Every Enterprise Pitch Against Harvey Is a Death Match
“We have one big competitor, and they come up on every, it's a, you know, death match on every deal. It's super competitive. We have a ton of respect for them.”
Patrick Forquer May 11, 2026 ▶ 19:26 Inside Legora: Jude Law Generated $50M Pipeline | Are They Undervalued at $5.5BN? | Patrick Forquer · 20VC with Harry Stebbings
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Tobi Lütke: Shopify's logistics fulfillment pivot was my most public mistake
“I think my most public mistake was going into Full on logistics and physical warehouse building just before AI got really good and not like, and we didn't have the ability to you know, do both of those things at the same time. So we actually had to like abando…”
Tobi Lütke May 4, 2026 ▶ 51:05 Shopify CEO on How AI is a Scapegoat for Mass Layoffs & Trump Derangement Syndrome in Canada · 20VC with Harry Stebbings
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Lindquist: Clay's quota-to-OTE ratio is seven and a half
“Our quota to OT ratio is like seven and a half.”
Becca Lindquist May 2, 2026 ▶ 0:15 Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
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Stebbings: Passed on Granola, predicting no one would fund them
“Granada, Granada, I was the first VC they met, and I turned them down. I sent my partner a note saying someone should set up a JustGiving page for them, because no one will give them money.”
Harry Stebbings May 2, 2026 ▶ 59:45 Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
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Lemkin: Salesforce bill jumped to $22,000 while seats dropped to three
“Our Salesforce bill went up from 12,000 to 22,000 dollars a year, and our seats went down from 10 to two plus one.”
Jason Lemkin Apr 30, 2026 ▶ 25:54 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
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Lemkin: $100M+ startup reports three different ARR metrics monthly
“And for example, I've got one investment I made that's north of nine figures in revenue. I get three different ARR numbers each month. Three different definitions.”
Jason Lemkin Apr 30, 2026 ▶ 1:07:19 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Disclosure
AppLovin Cut Its HR Department From 70-80 Staff Down to 15
“But HR, for example, like that I touched on earlier, we went and took a pretty large HR organization, one that I think had 70, 80 people on it, and now might have 15.”
Adam Foroughi Apr 27, 2026 ▶ 20:14 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
Disclosure
AppLovin Shut Down Investor Relations to Buy Back Stock During 92% Crash
“So when we fell in 2022 one of the things we did on the investor relations side, you fall 92%, no one's buying your stock. We said, we're gonna buy our own shares, and we're gonna shut down investor relations, because what's the point? Why do I need to go to a…”
Adam Foroughi Apr 27, 2026 ▶ 40:00 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
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Midha: AMP provides billions in compute infrastructure at cost
“We're actually giving away most of our compute at cost. Now, if you're a shareholder, you'd go, wait on, do you have billions of dollars of compute infrastructure you're giving away at cost? Yes, because we think that's the right thing for humanity.”
Anjney Midha Apr 14, 2026 ▶ 22:10 The Early Days of Anthropic & How 21 of 22 VCs Rejected It | The Four Bottlenecks in AI | Anj Midha · 20VC with Harry Stebbings
Disclosure
Midha: AMP Is Securing 1.3 Gigawatts of Compute Infrastructure
“We have started securing about 1.3 gigawatts of computer infrastructure. That's roughly forty billion dollars of cloud spend over the next four years. And that is financed roughly, you know, between with about 20% of equity. The remaining is debt. So 20%, that…”
Anjney Midha Apr 14, 2026 ▶ 33:00 The Early Days of Anthropic & How 21 of 22 VCs Rejected It | The Four Bottlenecks in AI | Anj Midha · 20VC with Harry Stebbings
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Reyna: ElevenLabs is willing to lose money entering the government vertical
“And I don't care if I don't make enough money to justify it or like I lose money. It doesn't really matter to me.”
Carles Reina Apr 11, 2026 ▶ 36:26 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
Disclosure
ElevenLabs forces CVC investors to deliver revenue or face contractual penalties
“So how do you figure out something that works along the way so that, like, you put and end up saying, you know what, you will invest for every million dollars that you want to invest, you need to actually, like, bring X amount of revenues in the next 12 months…”
Carles Reina Apr 11, 2026 ▶ 57:47 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
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