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20VC Prediction Open · timeframe Sep 2030
Lawson: AI will decimate SaaS seat bases and human workflow roles
“The thing I would say though about any company in SAS today, and Atlassian is a Prime example of this is they are primed for, ah, disruption right now because AI is going to decimate their seat base for their products. It'll decimate the roles people are playi…”
Jeff Lawson Sep 11, 2025 ▶ 59:19 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
20VC 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
20VC Assertion Not checkable as stated
Lawson: No Legacy Non-Tech Company Succeeded Opening Silicon Valley Offices
“Well, and I struggle to think of a single, like, kind of, let's say, legacy company who said, hey, we got to get in on the software thing, and opened up their Silicon Valley office and actually succeeded in that.”
Jeff Lawson Sep 11, 2025 ▶ 42:08 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
HOW I BUILT THIS Prediction Not checkable as stated
Jeff Lawson: Future company offices will be showrooms, offsites, and coffee shops
“I personally believe that the future of a company like ours, I think that the company's offices are going to consist of three different types of locations. I think you'll have number one, like a showroom, the place where you bring customers or like recruits or…”
Jeff Lawson Apr 3, 2023 ▶ 1:10:18 Twilio: Jeff Lawson
SAASTR Assertion Contradicted
Lawson: Twilio has never killed or deprecated an API it built
“We've killed the teams, but maintain the products. So we find another home internally for the product to live. We have never killed an API that we've ever built.”
Jeff Lawson Jul 10, 2017 ▶ 26:47 Twilio: The Inside Story with Jeff Lawson, CEO/Co-Founder
SAASTR Assertion Not checkable as stated
Twilio maintains five nines API availability despite 18,000 annual production deployments
“Now we can ship 18,000 times a year, and we have a five nines available API, and a seven nines success rate of the request that we're serving.”
Jeff Lawson Jul 10, 2017 ▶ 30:27 Twilio: The Inside Story with Jeff Lawson, CEO/Co-Founder
20VC Assertion Open
Lawson: Domino's Pizza Outperformed Google Stock Over 10 Years
“Better return than Google over that time period.”
Jeff Lawson Sep 11, 2025 ▶ 41:50 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
20VC Assertion Not checkable as stated
Lawson: Corporate venture investing gives Salesforce direct core business advantages
“In that, in the Salesforce world, the answer I would say definitely is yes. Obviously it cemented the role in the center of an ecosystem. They ended up making acquisitions. They have more information to make their product decisions on, like all sorts of benefi…”
Jeff Lawson Sep 11, 2025 ▶ 50:52 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
20VC Prediction Not checkable as stated
Lawson: Atlassian and Mike Cannon-Brookes will stay aggressive on acquisitions
“So I think Mike will be one of the more aggressive on the acquisitions front because they've always been and so I think it's in the DNA of Atlassian, so I do think we are looking at one of those, even if I am not fully on board with the most recent.”
Jeff Lawson Sep 11, 2025 ▶ 1:10:05 OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings
HOW I BUILT THIS Assertion Not checkable as stated
Lawson: Twilio was among the only companies marketing directly to developers
“And at that time, no one else was trying to reach them. We were like one of the only ones.”
Jeff Lawson Apr 3, 2023 ▶ 55:19 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Not checkable as stated
Telecom carriers shut down competing developer API platforms within a year
“Almost every carrier in the world that I can think of in that era, in those early days, like, Built an API on top of their services and launched with great fanfare, their developer platform. And every one of those carriers within 12 months had shut it down.”
Jeff Lawson Apr 3, 2023 ▶ 56:41 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Not checkable as stated
Jeff Lawson: Twilio's SF offices see low single-digit utilization
“At the beginning of the pandemic, we had, I think, three buildings in San Francisco. And today, you look at those offices, they're about, you know, low single digit percent utilization.”
Jeff Lawson Apr 3, 2023 ▶ 1:09:23 Twilio: Jeff Lawson
SAASTR Assertion Not checkable as stated
Lawson: Top software companies spend 40% to 50% of R&D on internal platforms
“It's not at all uncommon for great software companies to spend upwards of 40, even 50% of their total R&D budget on those platforms. Because those investments are multiplying the investments that you're making in the other 50% of your R&D investments.”
Jeff Lawson Jan 15, 2021 ▶ 37:29 How To Collaborate, Manage & Work With Developers With Jeff Lawson, CEO Twilio
SAASTR Prediction Not checkable as stated
Lawson: Twilio employees will shuffle teams based on remote work preferences post-pandemic
“Within Twilio, I suspect when we can go back to offices, there will be a bit of a team shuffling going on, because certain teams will say, we want to be back in an office, and other teams will say, we're really happy virtual, and people will find the teams tha…”
Jeff Lawson Jan 15, 2021 ▶ 45:41 How To Collaborate, Manage & Work With Developers With Jeff Lawson, CEO Twilio
HOW I BUILT THIS Assertion Supported
Versity raised an $11M venture round while its founders were undergrads
“Again, we're still basically full-time students, and we raised, I think, eleven million dollars.”
Jeff Lawson Apr 3, 2023 ▶ 12:00 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Not checkable as stated
Jeff Lawson says Versity generated only $26,000 in lifetime revenue
“And in the course of that, we made a total of about 26,000 dollars of revenue in the lifetime of the company.”
Jeff Lawson Apr 3, 2023 ▶ 14:52 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Not checkable as stated
Versity acquired users for $1 compared to CollegeClub's $50 CAC
“And I think they were paying like when they took their whole marketing spend and they divided it by the users, they were paying something like 50 dollars to acquire a customer. And so, that's a lot of money. And when you took the entire cost of operating our b…”
Jeff Lawson Apr 3, 2023 ▶ 16:12 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Contradicted
CollegeClub burned roughly $50M monthly before its canceled 2000 IPO
“They're like, yeah, we've been burning, you know, fifty million dollars a month or some ungodly number. And now that we're not going public, we don't, we're not, we don't have the money. And so we've got to reduce our burn, like, immediately.”
Jeff Lawson Apr 3, 2023 ▶ 19:20 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Supported
Lawson: Uber was an early Twilio customer for ride arrival texts
“You know, like one of our early customers was Uber, and they came to us and said, well, actually, we want to let you know when your ride's arriving. Can we do that with Twilio? We said, of course you could. And they, like a day later, rolled out the first vers…”
Jeff Lawson Apr 3, 2023 ▶ 40:37 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Supported
Twilio failed to raise any venture capital in summer 2008
“And so we spent that whole summer and did not have a dollar to show for it from investors. We raised no money.”
Jeff Lawson Apr 3, 2023 ▶ 45:47 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Not checkable as stated
Lawson: Sony Music was Twilio's first inbound customer post-launch
“I remember the day we launched Sony. Reached out. And you'd say, Sony? What did Sony need? And you'd sort of think about some big enterprise use case. Well, it was actually Sony Music, and there was a music promoter who worked at the record label who was like,…”
Jeff Lawson Apr 3, 2023 ▶ 48:38 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Partly supported
Uber had roughly five employees when Twilio won their business
“Uber, when we won them as a customer, I think the whole company was about five people.”
Jeff Lawson Apr 3, 2023 ▶ 52:26 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Not checkable as stated
Twilio generated $200K in year one and $2M in year two
“Our first year, we made 200,000 dollars. Our second year, we made two million dollars.”
Jeff Lawson Apr 3, 2023 ▶ 57:18 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Partly supported
Uber grew to account for a quarter of Twilio's total revenue
“So they were growing to be like a quarter of our revenue. I'm like, that's actually a problem. That's not something to celebrate. That's actually something to worry about.”
Jeff Lawson Apr 3, 2023 ▶ 59:19 Twilio: Jeff Lawson
20VC Assertion Supported
Twilio grew from 1,900 to over 5,000 employees in two years
“And one of the things I keep telling the company, because I actually just saw a stat that in the beginning of 2019, Twilio was 1900 employees. Here we are just over two years later and we're over 5000, right?”
Jeff Lawson Jun 28, 2021 ▶ 17:07 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
SAASTR Assertion Supported
Lawson: Domino's stock outperformed Google, Amazon, and Facebook over the past decade
“The Domino's stock since in the last decade has outperformed like Google and Amazon and like Facebook.”
Jeff Lawson Jan 15, 2021 ▶ 19:22 How To Collaborate, Manage & Work With Developers With Jeff Lawson, CEO Twilio
SAASTR Assertion Not checkable as stated
Lawson: Twilio's early top 50 accounts were personally closed by the CEO
“What I did is I looked back at, like, every major customer that, that, you know, I could look at, like, our top, like, 50 list or whatever, and I go through the list, and I, like, a substantial number of them I looked at, and I'm like, wow, when we were really…”
Jeff Lawson Jul 10, 2017 ▶ 19:52 Twilio: The Inside Story with Jeff Lawson, CEO/Co-Founder
HOW I BUILT THIS Assertion Partly supported
Versity raised a $1M friends and family round during college
“Well, we raised first a C like friends and family rounds. We raised money from people we knew and Kevin participated and a few other folks like that. And that was while we were still full-time students, we raised about, if I remember, a million dollars.”
Jeff Lawson Apr 3, 2023 ▶ 11:21 Twilio: Jeff Lawson
HOW I BUILT THIS Assertion Not checkable as stated
Twilio's first non-founding engineer requested a $100K salary
“We hired our first software developer who was not a founder joining the company, a guy named Adam Belli. And I remember Evan saying, hey, Adam is great. We really got to hire this guy, but he wants a salary of like a hundred K.”
Jeff Lawson Apr 3, 2023 ▶ 51:07 Twilio: Jeff Lawson
20VC Assertion Supported
Major telecom carriers launched API side projects during Twilio's early years
“And actually it's during the period of time Byron was talking about almost every major carrier did have an API program, believe it or not, but it were like small side project.”
Jeff Lawson Jun 28, 2021 ▶ 24:48 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
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