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Disclosure
a16z paid growth prices for early-stage Character.AI to back Noam Shazeer
“My partner, Sarah led around a character AI and, you know, it was extremely early stage and, You know, we invested at a, you know, what you would call a gross stage price. But we knew that the likelihood of some degree of success in backing Nome was extremely …”
David George Dec 15, 2025 ▶ 18:24 a16z's David George on the Most Controversial Bet at a16z & Do Margins and Revenue Matter in AI? · 20VC with Harry Stebbings
Disclosure
Wiz invests heavily in unquantifiable brand efforts over pipeline metrics
“And we spend a lot of our efforts on those types of things, and I have no way of tying it back to a number. And I don't really care because I think that's what really matters.”
Raz Herzberg Dec 12, 2025 ▶ 18:46 20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg
Disclosure
Wiz saved millions by building internal AI tools instead of buying SaaS
“I definitely think that we've been able to save ourselves a lot of SaaS requests that asked us for millions of dollars, and I can give you names of specific products after, and just build it internally.”
Raz Herzberg Dec 12, 2025 ▶ 1:12:41 20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg
Disclosure
Mansour: Kalshi lost team members twice before suing the US government
“The next day we came back, and we were like, we're gonna try again for the twenty-twenty-four election. And then we tried another year till the end of twenty-twenty-three. Then the government blocked it again. And then, so that's the second time. And then God …”
Tarek Mansour Dec 8, 2025 ▶ 18:18 Kalshi CEO Tarek Mansour on Raising $1BN, CNN and CNBC Deals & the Polymarket Feud · 20VC with Harry Stebbings
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Lemkin: Fastest-Growing Portfolio Companies Do Not Care About Profitability
“I think in the fastest growing companies that I've invested in, no one gives a rat's ass about the bottom line.”
Jason Lemkin Dec 4, 2025 ▶ 38:50 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Disclosure
Shlomo: Passed on AI agent startups like Manus over commoditization fears
“I had the opportunity to invest in like this agent companies, right? Like the Manus, the, those folks. I don't like, I felt like, I don't know the industry good enough to understand if at some point this would get commoditized by the model companies. And so th…”
Maor Shlomo Nov 24, 2025 ▶ 51:58 Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings
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Max Altman admits holding Gusto past its $10B valuation was a mistake
“It might not have hurt to sell Gusto. I think Gusto's a great business, but I think, you know, they were valued at ten billion at one point, and I think they're still gonna be a strong business. I don't know if they're gonna have explosive growth from there.”
Max Altman Nov 21, 2025 ▶ 1:05:02 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster
Disclosure
Randle: Dismissing CoreWeave as a low-margin compute middleman was wrong
“When CoreWeave was first raising in private markets, I was like, oh my god, this is, they're reselling a commodity, you know, they're a middleman, they're a broker of compute, it's gonna be low margin, yada, yada, yada. How wrong was I?”
Everett Randle Nov 10, 2025 ▶ 26:38 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
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Randle: Benchmark does not strictly adhere to fixed 20% ownership targets
“I think sometimes people confuse the inputs for the outputs at benchmark where it's like, oh, like they have to have 20% ownership and they only want to invest at a hundred posts. All these things. And I think that's, that couldn't be further from the truth. W…”
Everett Randle Nov 10, 2025 ▶ 39:51 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Disclosure
Lemkin says his last three VC investments yielded 6-8% ownership
“And the last three investments I've done are in the six to eight percent range, even though that's my rule.”
Jason Lemkin Nov 6, 2025 ▶ 26:15 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
Disclosure
Ferriss deliberately alienates 10% of his audience to preserve his authenticity
“So I will deliberately kind of routinely get rid of like 10% of my audience by just being unapologetically brazenly myself, showcasing the things that I would not be inclined to showcase otherwise, and I find that, at least for me, that has helped to keep off-…”
Tim Ferriss Oct 31, 2025 ▶ 10:34 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
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Ferriss: Viral video clips with 100M+ views drove zero podcast growth
“I've had clips, shorts, that have exceeded a hundred million views. The branding of the show is there. It's clearly an interview on my podcast. There's a link to the full episode, and the impact on the long-form episode has been imperceptible. You look at the …”
Tim Ferriss Oct 31, 2025 ▶ 13:04 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Lemkin: Will not invest in Anduril or defense startups building weapons
“No one, not interested in the company personally, just personally at this point in life. I just want to do things I'm interested in to a fault, not interested in building weapons and stuff like that. Just not my vibe.”
Jason Lemkin Oct 30, 2025 ▶ 1:25:14 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Disclosure
Bouaziz never conducts scheduled one-on-ones or formal performance reviews
“I've never had one-on-ones with them. I've never truly had performance reviews with them.”
Alex Bouaziz Oct 20, 2025 ▶ 13:51 Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation · 20VC with Harry Stebbings
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Snowflake neglected new customer acquisition for two years while optimizing for IPO
“And so we took our eye off the ball for, I want to say, like two years on new logo acquisition, and that hurt us.”
Chris Degnan Oct 10, 2025 ▶ 29:53 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan
Disclosure
Databricks outbid Snowflake for startup acquisitions by two to three times
“They buy companies that Snowflake Has had term sheets on for three times or two times the amount of money that Snowflake is offering to buy the companies for, because there's no consequence.”
Chris Degnan Oct 10, 2025 ▶ 31:41 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan
Disclosure
Snowflake Fired Second-Line Managers Who Couldn't Pitch the Product
“So we have fired managers last year. I went through a certification of second line managers and we fired people because they couldn't sell the product.”
Chris Degnan Oct 10, 2025 ▶ 36:37 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan
Disclosure
Snowflake eliminated its dedicated Customer Success department entirely
“And so I got rid of customer success. Now, customer success is a responsibility of the entire company.”
Chris Degnan Oct 10, 2025 ▶ 45:11 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan
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Former Snowflake CRO admits making more money made him a worse leader
“Worse. Because I don't want to do the hard things. When I say the hard things for a CRO is when you're five hundred million dollars, billion dollars in revenue, getting on a plane and traveling around the world, going on two week trips away from your family.”
Chris Degnan Oct 10, 2025 ▶ 50:12 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan
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Feldman: Cerebras achieved higher valuation because rival chip startups had negative margins
“I think the reason we were able to raise it a higher valuation and from better investors and more money is because we had them. Right? And others who were out looking for mark, looking for money had negative margins.”
Andrew Feldman Oct 6, 2025 ▶ 53:01 Cerebras CEO, Andrew Feldman on Why Raise $1BN and Delay the IPO & Why NVIDIA’s Worried About Growth · 20VC with Harry Stebbings
Disclosure
Feldman: Cerebras passed on a major China deal in 2019 before export controls
“We had a huge opportunity in, in 2019 to do a deal in China, and I decided to pass because I didn't think it was the right thing to do. Long before the Department of Commerce limited exports to China, I didn't think it was right.”
Andrew Feldman Oct 6, 2025 ▶ 57:00 Cerebras CEO, Andrew Feldman on Why Raise $1BN and Delay the IPO & Why NVIDIA’s Worried About Growth · 20VC with Harry Stebbings
Disclosure
UAE Accounted for 75% to 80% of Cerebras' H1 2024 Revenue
“I think in the S-one it says and that was for maybe the first half of 24, we haven't published others, but a lot. I think 75, 80%.”
Andrew Feldman Oct 6, 2025 ▶ 1:02:46 Cerebras CEO, Andrew Feldman on Why Raise $1BN and Delay the IPO & Why NVIDIA’s Worried About Growth · 20VC with Harry Stebbings
Disclosure
Lemkin: SaaStr team replaced 11 human employees with AI agents
“I live it that we've replaced 11 people on our team with AI agents.”
Jason Lemkin Oct 2, 2025 ▶ 29:50 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
Disclosure
General Catalyst reinvests all management fees instead of distributing them
“By the way, we, we're not, just to say, like, in our business, we don't distribute any fees. We invest everything back in the business, and that's a deep belief that we don't want to be in the game where the partners of the funds at General Catalyst Want bigge…”
Hemant Taneja Sep 22, 2025 ▶ 1:12:10 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
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Taneja: General Catalyst regrets passing on OpenAI over corporate structure concerns
“I look, that structure, many people overthought it, and I overthought it as well, and there's a lot going on on that platform that's changing the world, and I don't have a front row seat. So, yeah, I do regret that a little bit.”
Hemant Taneja Sep 22, 2025 ▶ 1:23:13 General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
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Lemkin: Telling 100% of founders with strong M&A offers to sell in 2025
“Every single founder. That I, this year that has had a strong M&A offer. I've told them to take it a hundred percent of the time.”
Jason Lemkin Sep 18, 2025 ▶ 40:42 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
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Lemkin: Over 51% of tech founders regret selling their companies
“In my experience as a founder, I, most, I would say more than 51% of founders regret it. I regret it.”
Jason Lemkin Sep 18, 2025 ▶ 1:10:59 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
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Mercor's customer concentration breakdown is similar to Nvidia's
“Our largest customer, I can't share the exact percentage, but the breakdown is relatively similar to Nvidia.”
Brendan Foody Sep 15, 2025 ▶ 17:38 Mercor CEO & Co-Founder, Brendan Foody: How They Grew from $1M to $500M in 17 Months · 20VC with Harry Stebbings
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ElevenLabs is considering acquiring a company worth hundreds of millions
“One that, that is, we are considering is an acquisition of another company now, which is a big company. And that company, you know, is in hundreds of millions of dollars.”
Mati Staniszewski Sep 8, 2025 ▶ 1:21:28 ElevenLabs CEO/Co-Founder, Mati Staniszewski:The Untold Story of Europe’s Fastest Growing AI Startup · 20VC with Harry Stebbings
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Alex Schultz: Meta is building a data center the size of Manhattan
“What we're doing in Louisiana, where we're building a data center the size of Manhattan”
Alex Schultz Sep 5, 2025 ▶ 16:15 20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader
Disclosure
Alex Schultz: Meta supported Apple against UK government encryption backdoor demands
“That's why we came out in support of Apple. That's why other companies have come out in support of Apple in that situation. Despite the fact, as companies, we've had a lot of disagreements. We supported Apple in that.”
Alex Schultz Sep 5, 2025 ▶ 31:32 20Growth: Meta CMO Alex Schultz on How All Founders Have to Change Their Marketing Playbook in a World of AI | Is AI Plateauing, What it Means if China Wins the AI Race and Why Zuck is a Generational Leader
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Jason James: Tezi won't hire full-time PMs until reaching 50 employees
“Like for us, my theory was we didn't need PMs until call it 50 people or so. We actually do have some gaps. And so we have PM That's like former senior director at Slack that contributes about 15 hours a week, and it really helps fill the gaps on his enterpris…”
Jason James Aug 29, 2025 ▶ 8:57 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi
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Benioff: Salesforce is not participating in AI talent buying frenzy
“No, and we're not.”
Marc Benioff Aug 28, 2025 ▶ 4:51 Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
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Lemkin: His organization spends $500K on 11 AI agents vs $12K on Salesforce
“So we're paying 10 grand, 12 grand a month, 12 grand a year for Salesforce. Nominally, nominally, nominally, we're paying 500,000 dollars for 11 AI agents.”
Jason Lemkin Aug 28, 2025 ▶ 40:35 Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
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Deeter: Bessemer refuses to hire sector-specific investors or protect cooling sectors
“This is very much why we don't hire sector-specific investors, and we don't give you air cover if your sector goes out of favor, meaning our job's to make RLPs money, and if you're in a sector that's cooling off, you better get the hell out and go somewhere el…”
Byron Deeter Aug 25, 2025 ▶ 1:00:54 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
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Lemkin: SaaStr replaced five human employees with 10 AI agents
“We have 10 AI agents at our little team that have replaced five humans and it's going to go up.”
Jason Lemkin Aug 21, 2025 ▶ 1:13:04 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
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Osika: Majority of Lovable's paid usage revenue goes to AI compute
“I don't give you the exact numbers, but if you look at the paid usage, it's majority, it's not everything.”
Anton Osika Aug 18, 2025 ▶ 9:40 Lovable CEO, Anton Osika: The State of Foundation Models, Grok vs OpenAI, and Replit vs Bolt · 20VC with Harry Stebbings
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Lemkin: Success Rate Placing Veteran B2B Executives Dropped to 10%
“Listen, until maybe 18 months ago, if any seasoned B to B executive that I knew needed a job, ok, that I knew reasonably well, I'd get him a job by an email. I could reach out to someone, not even in my portfolio, extended network founders I met that I knew me…”
Jason Lemkin Aug 14, 2025 ▶ 1:06:38 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
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Databricks waited until $500M ARR to verticalize its sales team
“I didn't go vertical at Databricks until we were probably five hundred million plus, right?”
Ron Gabrisko Aug 4, 2025 ▶ 25:37 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko
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CMU Endowment Is Willing to Pay 2.5% Fees and 30% Carry
“If you're raising you know, that early stage fund, the core five hundred million dollar Series A fund, charge us your, you know, two and a half and 20, and if you're good enough, two and a half and 30. We're okay with that, right?”
Miles Dieffenbach Aug 4, 2025 ▶ 51:35 Miles Dieffenbach: Inside Carnegie Mellon’s $4BN Endowment & The Math Behind DPI, TVPI, Illiquidity · 20VC with Harry Stebbings
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Carnegie Mellon Endowment Does Not Screen VC Managers for Founder Friendliness
“Yeah, I mean, we do not, when we're sourcing and we're doing reference work, that is not something we try to dig out. Like we want the most founder friendly GPs. That's not something we source for.”
Miles Dieffenbach Aug 4, 2025 ▶ 1:22:20 Miles Dieffenbach: Inside Carnegie Mellon’s $4BN Endowment & The Math Behind DPI, TVPI, Illiquidity · 20VC with Harry Stebbings
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Chen: Built Surge AI V1 solo rather than fundraising $10M-$30M
“As opposed to feeling like I needed to go out and hire 10 engineers in order to build a product, instead of feeling like I needed to go out and fundraise, you know, 10, 20, thirty million dollars in order to hire, you know, more people. Again, I just wanted to…”
Edwin Chen Jul 21, 2025 ▶ 17:17 Surge CEO & Co-Founder, Edwin Chen: Scaling to $1BN+ in Revenue with NO Funding · 20VC with Harry Stebbings
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Stebbings invested $12M in Lovable, citing consumer brand leadership
“Why did I write a twelve million dollar check into Lovable? I think very much in the same way that ChatGPT owns the consumer brand for that front end OS for the modern consumer, I think Lovable's reached escape velocity with the consumer brand in this space”
Harry Stebbings Jul 17, 2025 ▶ 45:18 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
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Stebbings: Lovable scaled from $4M to $19M ARR during funding round
“Jason, when I did the last round of Lovable, it was a two hundred million price, and I did it at a four million in revenue. By the time the deal was closed, it was at nineteen million in revenue.”
Harry Stebbings Jul 17, 2025 ▶ 57:35 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
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O'Driscoll: Scale GP would pass on xAI at a $200B valuation
“So I think they'll achieve a very hard technical problem with very low rewards. So that's why I would pass a two hundred million.”
Rory O'Driscoll Jul 17, 2025 ▶ 1:07:56 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
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Galloway reached his $150 million wealth target ten years ago
“My number was one hundred and fifty million because I thought it would be hard for me to spend half a million dollars a month, although I figured out how. And four percent of a hundred fifty million is six million, half a million dollars a month. I got there a…”
Scott Galloway Jul 7, 2025 ▶ 30:58 Scott Galloway on Billionaire Happiness, Money & Self-Worth | Why We Should Drink More & Not WFH · 20VC with Harry Stebbings
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Stebbings: 20VC portfolio company will surpass Superhuman's 8-year revenue in 9 months
“We are in a company that is similar to superhuman that will be at More than their revenue in nine months for what it took them eight years to go to.”
Harry Stebbings Jul 3, 2025 ▶ 54:04 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
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Stebbings: 20VC lost a $5M ARR Series A deal valued at $600M
“We lost to Series A, actually last 10 days, and it was doing five million in ARR and it was, yeah, started at like, two, twenty-five million ended up at 600.”
Harry Stebbings Jul 3, 2025 ▶ 1:11:48 Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
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