The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 43 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Lemkin: Only infrastructure SaaS companies are winning two-pronged AI customer growth
“To be a two-pronged AI beneficiary, you have to be able to monetize your AI, and you have to attract new customers. There's two prongs, and the ones that have done it so far are close to infra, right? Cloudflare, Twilio, Mongo, Datadog and even DigitalOcean”
Lemkin: Top 25 public software stocks slowed every quarter since Q1 2022
“Every single quarter since Q one of 20, 22 growth has slowed for the, for all public software stocks. Every single quarter it has slowed and it continues to slow. And there are a handful of folks that have reaccelerated like Mongo and Palantir. And there are a…”
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: 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 …”
Lemkin: Twilio Has Failed to Profit From Segment After Multi-Billion Acquisition
“It hasn't been able to make segment, make any money. Which it's paid billions of dollars for.”
Jain: Cloud cost savings are offset by rising startup labor costs
“So the cost saving that's come from the shift to, you know, AWS, Twilio, et cetera, it's offset by the increase in labor costs, which is why that number has stayed fairly stable, and we expect that to stay stable in the future.”
Lemkin: HubSpot and Salesforce must demonstrate AI revenue growth in 2026
“HubSpot and Salesforce got to deliver in 20, 26 because they're in play. They have the AI things they built, they ship the products, but they haven't seen the bump that data dog and Twilio and Mongo have”
Wang: SCGE held Twilio too long, missing out on legendary returns
“So Twilio initially was a very good investment for us and actually ended up being a decent investment overall. It could have been a legendary investment. We held on for too long.”
Gonto: 80% to 85% of top PLG revenue comes from enterprise accounts
“If you look at all of the companies like Atlassians of the world, like the Twilios of the world, Outsido, or even Bursell, most of them, what ends up happening is that 80, 85% of the revenue comes from mid-market and enterprise, 15% come from SMBs, but that 15…”
Niparko: The best product leaders are generalists across multiple domains
“The best product leaders within our organization are generalists can apply their craft to a bunch of different domains.”
Wesley Chan Passed on Twilio's Seed Round Due to Expert Bias
“And I passed on it because, you know, I looked at it and, you know, talked to my team at Google voice and everybody looked at it. It's like, oh, this is easy to do. Like, you know, once the company gets big enough, they don't need toilet anymore. Boy, I didn't…”
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.”
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.”
Twilio Built Software Layers to Avoid Becoming a Commoditized Infrastructure Pipe
“The commoditization of communications or the migration of their larger customers. So I think you asked a very insightful question along the way, which I probably didn't give enough due to, which is we worried about that very heavily. And so part of our Preempt…”
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.”
Early rounds for Lyft, Credit Karma, and Twilio were uncompetitive
“When we invested in Lyft out of FB Fund, I guess it was called Zimride at the time, and when we invested in Credit Karma and Twilio they were not really that competitive rounds, even though, you know, the founders were compelling most of the time.”
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 …”
O'Driscoll: Legacy SaaS giants have lost high-valuation growth premium
“These companies, they're in a much more bounded world now. They might grow 15%. They might grow five percent. They might trade at six times revenues. They might trade at four times revenues. You know, if you look at the stock chart, the area of magic is gone, …”
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, …”
Deeter: Bessemer owned 28% of Shopify and Twilio at IPO
“We own 28% of Shopify and Twilio at IPO and we owned, you know, well less than that of Procore and Service Titan just because we, you know, included a lot of other investors downstream.”
Gross: Passed on Twilio Seed Due to Misjudging Market Value Potential
“I saw the Twilio seed. I didn't think big enough. And this has been a problem with my kind of personal cognitive model for a while, is I didn't think big enough, I didn't understand, ah, how much value was there, and I over-indexed on how commoditized it would…”
Twilio conducts product reviews on demand rather than on fixed schedules
“We run product reviews on demand as product teams are at a point where they want additional input.”
Twilio Commits to Dual Listing on Long-Term Stock Exchange
“Just last week, this founder committed his company to being one of the first to dual list on the long-term stock exchange.”
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.”
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.”
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…”
Deeter Expected Video to Overtake Voice and SMS Much Faster
“I certainly have expected video to take off faster than it did. As you think about the Twilio product set, for instance, and all of the channels that we've entered now, I would have thought that voice and SMS would have plateaued earlier, and that video would …”
Twilio Went Through Multiple CROs Trying to Crack Enterprise Sales
“We went through several chief revenue officers who were quite capable, and yet couldn't fully crack it.”
Twilio's Revenue Was Declining Month-Over-Month When Bessemer First Invested
“When we made the investment, not only was the revenue tiny, but it was actually down month over month.”
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 …”
Hartz: HyperTrack is the Stripe for location-based services
“So if you think of messaging as with Twilio, or if you think of Stripe with payments, think of HyperTrack for location-based services, and it's exciting to me because it becomes a mechanism to imagine or to build all these great new services that if you think …”
Box and Twilio Reached $200M ARR Prior to Going Public
“In fact, the last two IPOs that we've seen at DFJ over the last couple years, Box and Twilio, were both companies that were on nearly two hundred million dollar annual revenue run rates before they got public.”
David Cohen: Twilio and Uber were Fund 1's first and fourth investments
“The first investment I made was in a company called Twilio. Fourth investment I made was in a company called Uber.”
O'Driscoll: OpenRouter is the Stripe or Twilio of LLM APIs
“From a business model perspective, in other words, the kind of front-end API to aggregate a lot of complexity, What Open Router does for LLMs, what Stripe does for money, and what Twilio does for telecoms.”
Deeter: Bessemer's largest all-time investments include Twilio, Canva, and Anthropic
“So it used to be Twilio. Then you know, probably StubHub, Canva, Anthropic Yeah, probably, probably that bucket.”
Niparko: Twilio's product hiring avoids theoretical case studies
“We don't give theoretical cases or external cases throughout the hiring process.”
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.”
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.”
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?”
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.”
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…”
Stebbings: David Cohen's portfolio companies have created over $80B in value
“To date, David has backed hundreds of startups, including the likes of, check this out, Uber, SendGrid, Twilio, ClassPass, PillPack, and many more. In total, these investments have gone on to create more than eighty billion dollars in value”