Jeff Lawson

24 statements across 7 episodes · 12 bullish · 3 bearish · 6 people on the record · first statement Apr 22, 2021 by Peter Reinhardt · said 102 times in 26 episodes since 2016 · across every show →

On the record as a speaker too: Jeff Lawson's record, appearances and statements → this page counts the times other people say the name.

Mentions by year

brought up most by Harry Stebbings (38), Byron Deeter (19), Jason Lemkin (12), Henry Ward (4), Wesley Chan (3), Stevie Case (3), Rory O'Driscoll (3), Jeff Immelt (3)

tap a year for its mentions
0020340620162017201820192020202120222023202420252026episodesmentions
03620162017201820192020202120222023202420252026episodes it came up in
007.5315620162017201820192020202120222023202420252026episodesmentions per episode
2026 11 mentions in 4 episodes 3 per episode
2025 20 mentions in 6 episodes 3 per episode
2024 7 mentions in 4 episodes 2 per episode
2023 5 mentions in 3 episodes 2 per episode
2022 5 mentions in 2 episodes 3 per episode
2021 39 mentions in 3 episodes 13 per episode
2019 9 mentions in 2 episodes 5 per episode
2017 2 mentions in 1 episode
2016 4 mentions in 1 episode

every mention, scene by scene, with the transcript →

Everything said about Jeff Lawson, oldest first

Apr 22, 2021 neutral
Assertion Supported
Twilio CEO Jeff Lawson spent 18 months convincing Reinhardt to sell
“No, you know, it took Jeff about 18 months to convince me that it was the right thing to do.”
Peter Reinhardt Apr 22, 2021 ▶ 19:26 20VC: Segment Founder Peter Reinhardt on His Learning Process, How Great Leaders Listen and Encourage Debate within Their Organisation & How To Use Data Intelligently To Improve Decision-Making
May 27, 2021 positive
Assertion Supported
Twilio Allocated 1% of Pre-IPO Equity to Charity, Not Founding Equity
“He early on came to the board and said, I want to allocate one percent of Twilio's equity and not in like a marketing way where it's one percent of when we founded it, but like one percent now immediately pre IPO, which by the way is now worth hundreds of mill…”
Byron Deeter May 27, 2021 ▶ 26:00 20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage
May 27, 2021 bullish
Assertion Supported
Twilio Is Bessemer's Largest Investment in Total Dollars and Returns
“The initial investment started with David Callen leading a 125,000 dollar seed investment as part of this seed extension round that Mitch Kapoor led, and Ethan Kurzweil, who's now one of our great partners, was a senior associate at the time, and Ethan slid a …”
Byron Deeter May 27, 2021 ▶ 4:22 20VC: The Twilio Memo: Bessemer's Byron Deeter on How a $125K Initial Check Became Bessemer's Largest Position, What The Influx of Late-Stage Capital Means For Venture Today & Why The Incumbent Advantage Is Now An Incumbent Disadvantage
Jun 28, 2021 positive
Insight
Lawson: The only failure in hypothesis testing is spending without clarity
“Success is getting to a true or false as quickly and cheaply as possible. As hypotheses, the only failure mode is failing to prove it true or false, of going like, Spending a lot of time or money and still not knowing if the hypothesis is true or false.”
Jeff Lawson Jun 28, 2021 ▶ 30:27 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021 negative
Opinion
Lawson: Choosing between diversity and meritocracy is a false dichotomy
“First of all, it is a straw argument that there's a choice between diversity and merit, right?”
Jeff Lawson Jun 28, 2021 ▶ 35:02 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021
Insight
Lawson: A CEO's hardest task is anticipating their role 12 months ahead
“Figuring out what my role needs to be 12 months from now.”
Jeff Lawson Jun 28, 2021 ▶ 42:32 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021 positive
Insight
Lawson: Empowered, wasteful companies beat disempowered, efficient organizations
“The one where people on the front line are empowered and there's waste, or the one where they're disempowered and there's no waste. I would take the empowered, wasteful company pretty much every day.”
Jeff Lawson Jun 28, 2021 ▶ 28:26 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021 positive
Insight
Lawson: Hire candidates based on 'distance traveled' rather than elite pedigree
“And I would say it's the person who traveled the greater distance Is the person who you want on your team, not the person who has the standing necessarily, but the person is, it's all about distance traveled, not position in life.”
Jeff Lawson Jun 28, 2021 ▶ 39:36 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021
Insight
Lawson: True customer enthusiasm displays as exploratory feature questions
“When they like the idea, what they do is they ask you questions like, well, could it do this? Could it do that? And what you're seeing there is it's like tickling this part of their brain. You're tickling a problem that they have that maybe they didn't even kn…”
Jeff Lawson Jun 28, 2021 ▶ 8:16 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021 positive
Insight
Lawson: Career progression should depend on hypothesis-testing speed, not idea correctness
“Your career does not depend on your idea being right. Your career depends on your ability to actually test hypotheses quickly and inexpensively.”
Jeff Lawson Jun 28, 2021 ▶ 30:49 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021 positive
Insight
Lawson: Executive vulnerability prevents employees from assuming bad intent during mistakes
“And I think that vulnerability gives you a lot of leash with people. Because when you are vulnerable, when you are a human, when you try to hide that from people, you can be wrong, but people don't ascribe male intent. Because they see you as a human being. Bu…”
Jeff Lawson Jun 28, 2021 ▶ 32:37 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021
Insight
Lawson: Cohesive company tribes require symbols, heroes, and rituals
“And like what creates a tribe, I think is really three things. It's your symbols, your heroes, and your rituals. And that actually allows you to create this identity for a group of human beings to accomplish something together.”
Jeff Lawson Jun 28, 2021 ▶ 11:54 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jun 28, 2021 positive
Insight
Lawson: Actionable operating principles are more useful than general company values
“Values are nice, but principles are actually more usable. Principles are actually more aligning. Principles, how we get things done.”
Jeff Lawson Jun 28, 2021 ▶ 22:00 20VC: Twilio's Jeff Lawson on What It Takes To Create a Tribe, How To Create Anti-Fragile Organisations Through Decentralised Decision-Making and Why Values Are Nice But Principles Are Better
Jul 22, 2021 bullish
Prediction Not checkable as stated
Immelt: I will get a Twilio tattoo when they hit $5B revenue
“That's absolutely true. I got in 2006 and I told Jeff Lawson that when Twilio gets to be five billion dollars in revenue, I'm going to get a tattoo of the owl, which is the kind of the Twilio symbol.”
Jeff Immelt Jul 22, 2021 ▶ 28:50 20VC: Jeff Immelt on Leadership Lessons from 16 Years as CEO @ GE, Incumbent Innovation; Why Some Have Failed and Other Succeeded, When Boards Have A Positive vs Negative Impact on a Company & The One Fear Startup Founders Are Allowed To Have
Jul 22, 2021 positive
Opinion
Immelt: Twilio's Jeff Lawson excels at filtering out bad advice and distractions
“I think Jeff is awesome, and that he's a really good listener, but he doesn't listen all the time, and he doesn't listen to everybody, which I, behind the scenes, say to Jeff, I love that about you, really, is that you're discerning, you've got a nose for BS, …”
Jeff Immelt Jul 22, 2021 ▶ 14:36 20VC: Jeff Immelt on Leadership Lessons from 16 Years as CEO @ GE, Incumbent Innovation; Why Some Have Failed and Other Succeeded, When Boards Have A Positive vs Negative Impact on a Company & The One Fear Startup Founders Are Allowed To Have
Jan 25, 2023 positive
Assertion Supported
Twilio had a $200M run rate at IPO, aiming for $1B
“We, you know, IPO, we were two hundred million dollar run rate. And Jeff had set out this vision of we're gonna get to a billion dollar run rate.”
Stevie Case Jan 25, 2023 ▶ 16:56 Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970 · 20VC with Harry Stebbings
Sep 11, 2025 bearish
Opinion
Jeff Lawson: AI inference is not complex enough to sustain premium margins
“I believe inference itself is not such a hard algorithmic solve that, you know, you need to pay someone else to do it for you, but clearly training a model is”
Jeff Lawson Sep 11, 2025 ▶ 1:22:45 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025 negative
Assertion Not checkable as stated
Lawson: Most of Stripe's non-core product portfolio does not drive meaningful revenue
“I have heard whispers that a lot of their product portfolio is not really contributing to the business. It really is the core business, which is, you know, pretty common. I'd say probably the same of, you know, largely the same of Twilio too, right? It's a, it…”
Jeff Lawson Sep 11, 2025 ▶ 1:15:38 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025
Insight
Lawson: Founders commit 100% of capital, making VC portfolio concentration easy
“When I start a company, this is my, I mean, until now, all my prior ventures, that was a hundred percent of my capital allocation for myself, for my life, For my time, for my bank account, for everything. And so the whole idea that an investor would you know, …”
Jeff Lawson Sep 11, 2025 ▶ 29:36 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025 positive
Insight
Lawson: Cloudflare's DNS position gives it an ideal product expansion surface area
“I always admired the product surface area that Cloudflare had. Because they sit at this super strategic intersection of the world and then your website. And then you can ask the, and it's a dashboard. So once you're inserted into the DNS, and you're proxying a…”
Jeff Lawson Sep 11, 2025 ▶ 1:14:12 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025
Insight
Jeff Lawson: Only three API categories achieve breakaway revenue
“I analyzed every developer thing that was out there, and I decided there were three categories of developer companies, and only, sorry, there were many kinds, only three that actually got breakaway revenue. And there were a lot of folks that were stocked with …”
Jeff Lawson Sep 11, 2025 ▶ 1:17:22 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025
Insight
Jeff Lawson: Developers recreate paid API software internally at scale
“The problem is that developers, A, take your really cool thing that you're trying to charge them for as a challenge. Can I go make that myself? It's like a challenge. Like you're challenging me. You're saying I'm a developer who can't build the thing you built…”
Jeff Lawson Sep 11, 2025 ▶ 1:19:43 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Sep 11, 2025 neutral
Insight
Lawson: Financially rational founders should work at hyperscalers, not start companies
“If you just want to make money, probability adjusted, you should just go get a job at a hyperscaler. You will probability, probability adjusted, you'll make more money. So you don't start companies to make money. You start companies because you love what you'r…”
Jeff Lawson Sep 11, 2025 ▶ 12:57 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
Feb 19, 2026
Insight
Lemkin: Mistreated founder CEOs will return if boards offer humble pie and big packages
“When you're treated terribly as a CEO was like Jeff is, if people come back with humble pie and you care, you get over it. You got to pay the price. Like they might have to have to have given them a half million billion dollar package, but if there's a little …”
Jason Lemkin Feb 19, 2026 ▶ 1:26:57 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
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