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Twilio

also referred to as: twilios

includes Twilio Flex, Twilio Segment Personas

43 statements across 24 episodes · 16 bullish · 7 bearish · 18 people on the record · first statement Jun 27, 2016 by David Cohen · said 291 times in 96 episodes since 2016 · across every show →

Mentions by year, the whole family

brought up most by Harry Stebbings (109), Jason Lemkin (41), Byron Deeter (35), Jeff Lawson (30), Stevie Case (15), Jordan Van Horn (4), Adam Gross (4), Wesley Chan (3)

tap a year for its mentions
004010802020162017201820192020202120222023202420252026episodesmentions
0102020162017201820192020202120222023202420252026episodes it came up in
007.510152020162017201820192020202120222023202420252026episodesmentions per episode
2026 31 mentions in 12 episodes 3 per episode
2025 54 mentions in 16 episodes 3 per episode
2024 17 mentions in 12 episodes 1 per episode
2023 31 mentions in 10 episodes 3 per episode
2022 33 mentions in 16 episodes 2 per episode
2021 70 mentions in 6 episodes 12 per episode
2020 4 mentions in 4 episodes 1 per episode
2019 10 mentions in 5 episodes 2 per episode
2018 3 mentions in 3 episodes 1 per episode
2017 25 mentions in 8 episodes 3 per episode
2016 13 mentions in 4 episodes 3 per episode

every mention, scene by scene, with the transcript →

Everything said about Twilio, oldest first

Jun 27, 2016 positive
Disclosure
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.”
David Cohen Jun 27, 2016 ▶ 5:46 20VC: Techstars Founder, David Cohen on Scaling Techstars Ventures and Investing In Uber, Twilio and Sendgrid
Aug 15, 2016 neutral
Assertion Not checkable as stated
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.”
Dave McClure Aug 15, 2016 ▶ 5:33 20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing
Feb 8, 2017
Assertion Supported
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.”
Randy Glein Feb 8, 2017 ▶ 14:11 20VC: The Radical Changes In Public Market Expectations, The Right Way To Assess Valuation & What It Means To Be A Disciplined & Diligent Investor with Randy Glein, Partner @ DFJ Growth
May 22, 2017 bullish
Opinion
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 …”
Kevin Hartz May 22, 2017 ▶ 19:01 20VC: Founders Fund's Kevin Hartz on Why Investing In Silicon Valley Is Broken & Why Fearlessness Is What Makes The Truly Great Investors
Feb 11, 2019 positive
Assertion Supported
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”
Harry Stebbings Feb 11, 2019 ▶ 0:30 20VC: Techstars Founder David Cohen on Why Seed Investing Is A Different Asset Class To Venture, What Makes The Best And The Worst Board Members & Why Every Company Has To Have A Pessimist In The Room
Jan 6, 2020 neutral
Insight
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.”
Gaurav Jain Jan 6, 2020 ▶ 12:21 20VC: Why Now Is The Hardest Time To Raise an Institutional Pre-Seed in the Last Decade, What To Do When The Founder and VC Interests Do Not Align & The Rise of Pre-Emptive Rounds with Gaurav Jain, Founder & Managing Partner @ Afore Capital
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
What-if
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 …”
Byron Deeter May 27, 2021 ▶ 15:02 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
Disclosure
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…”
Byron Deeter May 27, 2021 ▶ 36:32 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
Assertion Partly supported
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.”
Byron Deeter May 27, 2021 ▶ 18:07 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 neutral
Disclosure
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.”
Byron Deeter May 27, 2021 ▶ 6:17 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
Assertion Supported
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.”
Harry Stebbings Jun 28, 2021 ▶ 0:01 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: 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
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
Jun 28, 2021
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
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: 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
Aug 22, 2022 negative
Disclosure
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…”
Wesley Chan Aug 22, 2022 ▶ 34:34 Wesley Chan: How I Created Google Analytics; The Founding Story of Gmail & Canva | 20VC #919 · 20VC with Harry Stebbings
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 29, 2023 positive
Insight
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.”
Kevin Niparko Sep 29, 2023 ▶ 21:04 Kevin Niparko: Big Mistakes Founders Make When Hiring Product Teams | E1066 · 20VC with Harry Stebbings
Sep 29, 2023
Disclosure
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.”
Kevin Niparko Sep 29, 2023 ▶ 34:02 Kevin Niparko: Big Mistakes Founders Make When Hiring Product Teams | E1066 · 20VC with Harry Stebbings
Sep 29, 2023
Assertion Not checkable as stated
Niparko: Twilio's product hiring avoids theoretical case studies
“We don't give theoretical cases or external cases throughout the hiring process.”
Kevin Niparko Sep 29, 2023 ▶ 19:31 Kevin Niparko: Big Mistakes Founders Make When Hiring Product Teams | E1066 · 20VC with Harry Stebbings
Feb 14, 2024
Assertion Supported
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…”
Martin Gontovnikas (Gonto) Feb 14, 2024 ▶ 40:38 Martin Gontovnikas (Gonto): The Biggest Mistakes Startups Make When Scaling into Enterprises | E1115 · 20VC with Harry Stebbings
Apr 26, 2024 negative
Disclosure
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…”
Adam Gross Apr 26, 2024 ▶ 47:10 Adam Gross: Why Startups Doing Paid Under $100M ARR are not PLG | E1145 · 20VC with Harry Stebbings
Jun 3, 2024 negative
Assertion Supported
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.”
Jason Lemkin Jun 3, 2024 ▶ 37:59 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Oct 9, 2024 bearish
Disclosure
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.”
Jeff Wang Oct 9, 2024 ▶ 30:39 Jeff Wang: Sequoia Capital's $9BN Global Equities Fund on The Future for NVIDIA, Google & Meta|E1212 · 20VC with Harry Stebbings
Aug 25, 2025
Disclosure
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.”
Byron Deeter Aug 25, 2025 ▶ 51:22 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Aug 25, 2025
Disclosure
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.”
Byron Deeter Aug 25, 2025 ▶ 44:54 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 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
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
Nov 6, 2025 bearish
Prediction Not checkable as stated
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”
Jason Lemkin Nov 6, 2025 ▶ 59:00 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
Nov 6, 2025 neutral
Insight
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, …”
Rory O'Driscoll Nov 6, 2025 ▶ 53:07 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
Feb 5, 2026 bearish
Assertion Open · timeframe Feb 2027
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…”
Jason Lemkin Feb 5, 2026 ▶ 14:57 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
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
May 7, 2026 neutral
Insight
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”
Jason Lemkin May 7, 2026 ▶ 49:21 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
Jul 29, 2026 positive
Insight
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.”
Rory O'Driscoll Jul 29, 2026 ▶ 1:13:42 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
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