I worked at Twilio for nearly 10 years and it's hard to overstate what a gift it was to work there and see Jeff operate as CEO up-close.
He created an environment where (at our best) we could have fun doing work that had a real impact, and we could it with people we enjoyed doing the work with. He pushed us to be creative to authentically empower and inspire developers. Wanna build a video game that teaches developers how to code and use Twilio? Let's try it! Wanna build an AI application with Tony Hawk and have Tony Hawk debug the code live on stage? Sure!
And Jeff would always be spending time with developer tools and Twilio's products himself, to the point that he could live code at the drop of a hat to show off what we'd been working on. This meant his own understanding of developers and their problems never ceased to amaze me.
But more than all of that, he was a rare CEO that led with empathy, humility and care.
Thank you, jeffiel. We can't wait to see what you build next.
Because Jeff wanted to be a celebrity CEO, and it was to the detriment of the company.
All of Twilio's growth (as a public company) happened on George's watch.
I don't think it's a coincidence that well after George left, on Jeff's watch - they had to do 3 different layoff for a total of ~24% of their entire public company being let go.
Note: former senior level Twilio employee, posted anonymous for obvious reasons.
For a public company, the CEO has to be a public CEO. Everyone takes on a different persona (some sell themselves as business geniuses, others as creative geniuses, and others as someone you wanna grab a beer with). Some really like it, and some do it begrudgingly. But at the end of the day, you can't be the same CEO of a public company as you were when you were private.
I've never known Jeff to hobnob with celebrities, travel in luxury or abandon his company. I'm not sure he's a "celebrity CEO" as much as he just became a public one, although I don't know him personally.
(FWIW, this is the reason I'd never want to go public. I personally don't like the system, but that doesn't mean it's not how the system works.)
Only if you pretend that the CEOs job is purely for raising money.
Nominally, CEOs are supposed to run the company and help brew the culture that makes that company productive.
We've grown a bunch of celebrity CEOs because people stopped caring about how companies worked over the last 10 years of low interest rates. But now that it's harder to raise money, it's time to see these guys run the companies they built.
Everything you said here is true, but I don't think it applies to Twilio or Jeff.
I don't think you can accuse Jeff of not caring about company culture. He built one of the defining dev cultures out there. Yes, this have changed as they've grown, but I've always found the people and offices of Twilio to be warm, productive and smart.
And Twilio was forged in the hardest time to raise money ever... 2008. If anyone knows how hard it is to build in a climate without easy money, it would be Jeff.
Memories are short, but Twilio was built when doing what seemed obvious - add an API to telecom services - was really hard. It's what Stripe is (doing, not done) to banking & payment, what countless companies have failed to do with Healthcare... I met Jeff in the early days and the fact that he (a) managed to stay the CEO through this growth & timeline, and (b) gave few enough sh!ts to maintain a hacker dev mentality makes him a notable standout. I'm not surprised that lots of people with legitimate viewpoints and perspectives DO/DID NOT like him or his approach. To me, that's a feature; we need less CEOs and senior executives who try to be all things to all people.
I was tasked with taking over some of jeffiel’s code bases around the time period we are discussing here. He perfectly skirted the line of telling me what he was thinking while writing stuff and simultaneously staying out of it and letting the people he hired take the reins. He spent most of his time interacting with Cxx and Director level people to set the tone and direction of the company, while still taking the time to know what ICs were doing so that he could usefully answer questions and use our products.
IMO, you and the GP are onto something with the term "celebrity CEO". In Jeff's case, he seems like a celebrity CEO for his employees/developers, who we identify with, though not for his customers, who we are largely not.
His customers probably expected better products, whereas his developers expected another round of amazing perks and fun work.
It's also a double edged sword where greater visibility leads to greater scrutiny. Galen Weston Jr stepped into the public eye much more during the pandemic as the face of Loblaws (Canadian grocery chain), and although it originally was welcome, he ended up outing himself as just another entitled, out of touch zillionaire, and at least in my social circles becoming kind of as punchline.
Why's that? He has been doing the commercials for around a couple of decades, staring long before he was the one doing the casting. Even after taking that role in 2016, the previous commenter points out that the commercials continued to be well received until well into the 2020s. It was a successful formula for a long time.
Indeed, positive audience sentiment has an expiration date. He rode the wave too long, perhaps, but it is hard to know when to stop. All ongoing media productions (e.g. TV shows) suffer from the same problem and question of when to keep going and when to move on.
I didn't actually know that he'd been doing it for a while, but I've not ever been a regular TV viewer. The change from my perspective was the commercials showing up in my Facebook feed and my family group chat joking around about the latest dispatches from old Gal Pal and how we could pick up a shrimp ring for 20% off.
So even if it was a longstanding thing, pushing the content toward a more millenial/gen-z audience is still a new direction and risk.
In the end, the biggest factor was the dissonance between his warm, cozy "all in this together" messaging combined with grocery price hikes and news like this coming on the other side of it all: https://www.blogto.com/city/2022/11/loblaw-report-profit-foo...
Funny thing is that restaurant patronage has declined considerably in Canada in the past year or so. Even with many restaurants now operating at a loss (i.e. paying you to eat) to try and win back customers, they are failing to capture hearts and minds.
If people aren't eating at restaurants, it is almost certain they are getting their food at the grocery store instead. For all the mockery of Galen, it seems the marketing strategy has been unbelievably successful.
That's probably why he continued to cast himself even as the audience focus shifted to millennials and gen-z. Letting someone laughing at you for a few minutes is no big deal. Watching them love you when they show up at your store over and over makes it all worthwhile, I'm sure.
I work in tech and had never heard of Jeff or George. I could name every CEO of Twitter or Google, or the founding CEOs of companies like Stripe, AirBnB, Uber, Coinbase, etc. Companies like Twilio and Unity don't really register.
I've worked on some of the foss tech (infra and ptsn) that twilio has used for almost a decade. Know all about what the company does. Have applied there (to which they never replied). Known plenty that work there.
Ironically my previous partner works there and she didn't know anything about the company prior to taking the job so me not even getting a reply to my application was a jab. I've always seen twilio in a positive light they do some really interesting work.
I live in the city of their HQ. I have no clue who the people mentioned in this thread are either but it makes sense that they'd see the CEOs in a positive light with how much positive I hear(d) about the place.
There actually haven't been that many, and double-checking against Wikipedia I forgot Parag Agrawal but Wikipedia forgot Linda Yaccarino. I divide them up into eras and power struggles:
1. Jack Dorsey. Founding era, founding engineer, forced out when Twitter was ~30 employees because he had no management experience.
2. Evan Williams. Growth era. Another founder, but one who had past experience dealing with hypergrowth, getting companies acquired, and working inside a big company.
3. Dick Costolo. Maturation era. Adult supervision, he's the professional CEO hired to manage Twitter because both of its previous CEOs were really startup people.
4. Jack Dorsey (2). Came back after gaining some political savvy and learning how to launch a boardroom coup. Founded Square in the meantime and got a bunch of experience being CEO of another company. Also famously the guy who shut down the Jan 6th insurrection by blocking the sitting U.S. president from Twitter.
5. Parag Agrawal. Caretaker; Twitter was in trouble by then and Jack Dorsey was either forced out or decided it was better to die a hero than be remembered as a villain.
6. Elon Musk. Bought Twitter in a fit of insanity.
7. Linda Yaccarino. Glass cliff. Installed as CEO so that X's eventual demise is not Elon Musk's problem.
I don't know the right answer here, but there are thousands of public companies. If every CEO has to be a celebrity, meaning that everybody knows them and which company they are the CEO of, it's going to end up like for actors: tier one world superstars, tier two stars, then people you don't hear much about, then people you read their names sometimes in the closing credits, otherwise they are only random faces on screen.
If that's the case, the top layers of the system have space for so many CEOs. Some won't even care to be there, they'll just do their job and take the salary plus bonuses.
Sure. I'd say 99% of people in tech couldn't name the Twilio CEO. I don't think he's really a celebrity CEO, at least not in the way that's being implied about him (as in, I think "public" and "celebrity" are being conflated here).
Jobs certainly was a celebrity CEO, and despite all the criticism of him, I've never once heard anyone imply he was bad for Apple (or its shareholders). Musk is a celebrity CEO, much to the detriment (and potentially benefit? who knows) of his companies.
The CEO’s job is to create value. The answer to your question is “it depends”.
If buyers of their services are impressed with his ability to live code and that moves the needle on results, then yes. If the same can be accomplished by having a non-CEO developer evangelist, then probably no.
There's celebrity CEOs and there's celebrity CEOs.
Without googling, can you tell me the name of the CEO of Target? Sony? Texas Instruments? BMW? FedEx? Mitsubishi? Exxon? Home Depot? Siemens? Procter & Gamble? 3M? Nestle? Broadcom?
I certainly can't.
But I bet you can tell me who the CEOs of Tesla and Amazon are.
Just because whoever-is-in-charge-of-siemens hasn't run a vanity PR campaign to raise their personal profile, doesn't mean it would help the company if they did.
The sum of the market cap of the first group of companies is ~2.068T USD, while the sum of the second group is ~2.270T.
And of course the CEO of Tesla is(?) allegedly the richest man in the world, which is one of the reasons why people know him. And I honestly don't remember the name of the CEO of Amazon since Jeff Bezos stepped down.
lmao Teslas market cap is such a joke. 750bn, 10x higher than BMW while I see tens of millions more BMWs on the road and the BMW brand has astronomically more staying power as brand recognition. Wild. Nobody would be surprised if Tesla flopped but we know BMW, a company over 100 years old won't flop.
I can't imagine being offered a choice between owning (the company) Tesla or BMW and picking Tesla.
edit: Tesla did 4.2% of total market in 2023, outpacing VW, Subaru and BMW. They did 25% more sales in 2023 than 2022. They sell 500-700k/yr right now with 2023 being 660k. BMW delivered 550k cars worldwide.
Shhh you must not rain on techbro's fanatical obsession with fantasy market caps. It's the only aspiration validating their particular niche of career.
This is not specifically about Jeff in any way, but no, it's not a CEO's job to be a celebrity. It's their job to allocate capital in a superior way (relative to the investors desires ie how much beta, and to marginal opportunities elsewhere in the market). If they cannot produce a better Risk Adjusted Return then they simply should be returning the capital, not being a rockstar and growing.
I've seen celebrity CEOs in non-public companies a lot more than in public companies. There is a difference between being the public face of the company and being a celebrity CEO.
George Hu cut his teeth under Benioff during the most meteoric rise of both Salesforce and Benioff's celebrity. I would be very surprised if Jeff's desire to be a public facing CEO would even cause George to notice, let alone bristle at.
It's more likely that someone as smart as George might have just looked at the fundamentals of the business and decided it could not keep this up over the long term.
or... it might have just been epic timing too. Probably.
I don't have any direct knowledge, but the gossip flying around internally at the time was that a big part of George leaving Twilio was because he wanted the CEO role, but knew Jeff wasn't going to leave and give it to him.
That was gossip, of course; sure, George may have decided back then that -- even with all the growth he drove -- Twilio wasn't going anywhere long-term.
The fact that George has not taken on a CEO role since tells me that it probably wasn't a driving factor for him. That's conjecture though. I think that role would be available to him at a lot of strong companies if that was his goal.
Being a celebrity CEO makes sense when interest rates are low and your main job is to keep convincing investors to pump in money. Of course when interest rates are high, and your main job is business and company fundamentals that's a lot less useful. I'm seeing a lot of startups (and public companies) with CEOs like that floundering right now.
I don't know the specifics of these two CEOs, but those were two very different eras financially in the tech sector. To nail all of it on just a CEO's door feels reductive, at best.
Please. George joined the company when it was damn near a decade old, and already a publicly-traded company. It's embarrassing to ascribe anywhere near the agency to someone like that than to a founder.
People who weren't there don't understand, but the world before "Ask Your Developer" was completely different than the world we live in today where developers are at the heart of how decisions are made, products are built and how the world itself is changing.
I joined Twilio in 2012 and I saw first hand how pivotal Jeff was in supporting the idea that in order for a platform to be successful it needed to treat developers like first class citizens, and not simply the recipient of a "directive to integrate" from the CTO.
This idea wasn't simply a fist bump to devs for cool points, it was a recognition that developers themselves held the key to innovation and creating radically new things. This culture led to entirely new ways of building API docs, designing developer dashboards, creating developer events, and so on.
So many of these things have become mainstream and the new baseline for platform companies that people forget how unlikely it was in the beginning and how hard Jeff had to fight to keep the company from treating developers as a means, and not as an end. And I think all developers who are happily hacking away on a free tier of a cool API with excellent docs and a vibrant developer community should tip their hat to a person who helped make this normal and influenced a generation of leaders to do the same.
> Wanna build a video game that teaches developers how to code and use Twilio? Let's try it! Wanna build an AI application with Tony Hawk and have Tony Hawk debug the code live on stage? Sure!
These are the strange effects of ZIRP and infinite QE. Many companies never had to care at all about profit and could just do things "for fun", and still see valuations skyrocket as long as they hired more people. What a time.
I think this is a bit reductive. Sure ZIRP created an environment where people could get away with trying crazy things, but there was still an expectation of growth in pursuit of some longer time-horizon market dominance. These kind of things may be more risky, but they still can be justified in the pursuit of market awareness and growth. Also, when you're building software products, there's real value to engaging the creativity of the team.
The fact that the music continued so long and led to incredible valuation inflation over the last 15 years made the excesses look a lot worse, but even in a more sane financial environment I'd argue you'd still want to do these things to be competitive in an attention-economy, just maybe not to the extremes we saw.
In my 32 years in the industry the best performing companies always did these things regardless of the macroeconomic climate. It’s when you ceded leadership to the accountants and shifted gears to maintenance mode that companies stopped growing. You never did these things for fun, you did these things because they had some knock on effect that made it potentially worth it, and in a portfolio of many small bets some would blow up into your next big product. Even the ones that seem far left field they created an environment where people felt allowed to dream at all, and their knock on effect was in creation of a risk taking culture.
Blaming low interest rates on taking risk and doing highly speculative things, and investing in a culture that values that by funding off the wall stuff puts too much emphasis on the capital markets. If the company was a steel producer, fine. If it’s a company that essentially captures the stuff of dreams and produces a service that executes thought stuff in machines, you have to decouple your R&D from capital management to the extent your free cash flow can accept it.
Note of course low interest rates and other capital market looseness will create more opportunity for this behavior, and not every company doing these things is doing some is a well managed way. But they don’t have to - that’s the magic of capitalism. Through a Darwinian process only those who strike magic win and survive and the others recycle and try again. This feels like a feature not a flaw of zero interest rates - it creates enormous value by virtue of incentivizing taking risk at a time of high innovation. There are times in history where innovation rates were very low, and zero interest rates would just incentivize broken behavior. But at a time when almost all growth is coming from innovation, maybe loose credit is smart. ml
> In my 32 years in the industry the best performing companies always did these things regardless of the macroeconomic climate.
Agreed. Creative, high performing people don't do well in a work environment that's structured like a regional bank.
Valve Software -- incredibly profitable, high performing and private company, did fun things like hire economists (and then later Greek prime minister) to study and simulate virtual, in-game economies [0].
Blizzard Entertainment had giant statues of orcs made and fan conventions before their downfall, ya know, in the ZIRP macro economic environment.
Google allowed their engineers 20% time. Before ZIRP.
I once heard that this was more like 120% time? Meaning, 'extracurricular activities' on company infra was allowed and encouraged, but not at the expense of regular productivity/output.
what about the hardware that significantly leverages their non-game software? I think the full ramifications of what they're doing with mobile gaming have not yet been felt.
> In my 32 years in the industry the best performing companies always did these things regardless of the macroeconomic climate.
I think the question is more about whether doing these things caused the company financial success, or whether the company's financial success caused them to do these things. It strikes me as plausible that it's almost always the latter, even if the company's financial success isn't attributable solely to the macroeconomic climate.
Usually the issue is you can’t encourage creative risk taking with structured austerity. Structured austerity is about improving operational efficiency and there’s a place for that. But at companies that survive and thrive on creative risk taking, giving the reigns to the CPAs kills the culture.
I think it’s usually a sign of success that to protect the golden goose you stop taking creative risks and focus on operational efficiency.
Macroeconomic conditions really matter a lot more for capital intensive enterprises like manufacturing, refining, real estate, etc. Most creative / R&D based companies are much less cost of capital sensitive and frankly low interest rates matter a heck of a lot less for their planning and operations.
> In my 32 years in the industry the best performing companies always did these things regardless of the macroeconomic climate.
My anecdote, FWIW, is that some of the worst performing startups do these tricks too.
There's something about flashy events and boondoggles that sound good on LinkedIn that draws bad founders into spending waaay too much on parties and fun activities.
Stripe obviously isn't in that category, but never assume that because a company spends a lot on parties and events that they're doing well.
> My anecdote, FWIW, is that some of the worst performing startups do these tricks too.
I absolutely agree with this. Monkey see, monkey do.
I think the big winners who make it "fun" are the exceptions that prove the rule. Whatever they really have that leads to success (be it simply luck, timing, connections, market fit, whathaveyou) is a lot less visible and harder to replicate than the lazy, obvious stuff like "make the workplace fun for developers" which any wannabe can emulate.
My wife is not in tech (and so enjoyed Silicon Valley quite a bit less than I did when we watched it together).
Every so often, she'd express frustration about the "over the top writing" in Silicon Valley. Way over half the time, I could tie whatever it was she was complaining about to some concrete story from our industry.
I read a great article about the making of the show and there were many real-life stories they couldn't include because they felt people wouldn't believe it was real.
I think their go-to example was meeting up with a Google X person in their offices and that person getting huffy about something or other and then trying to storm out. But then they had trouble with their keycard so there was that awkward pause because they couldn't just storm out and slam the door. Best part was that they were on inline skates (and rocking a pony tail!) so it was a totally Mike Judge perfect moment - weird silent tension as pony tail skate master is trying to beep himself out of the room.
I've definitely seen and heard about lots of strange things in SV that people simply wouldn't believe if they heard it.
My wife thought the show couldn't be reality. I told her I'm confident that almost everything you see in this show happened in SV to at least someone, just not the same company/people in a short amount of time.
It's like if you took every story in SV history and compressed it to one company in 6 years.
> In my 32 years in the industry the best performing companies always did these things regardless of the macroeconomic climate.
What companies?
Some of the best performing public tech companies of the past 30 years include Amazon, Apple, Netflix, Nvidia, and Microsoft.You can get some variety in this list by varying the exact start and end dates, but certainly the first 4 are going to make most lists. Others like Google and Facebook handily beat the total market.
Certainly a lot of companies that never went public (Instagram, WhatsApp, Credit Karma, etc...) performed very well for their investors when they got acquired. And some companies that since going public haven't been blockbuster successes, like Snowflake, still were probably very lucrative for their VCs and other early investors.
Anyway, I don't feel like most of the really great performing companies that come to my mind are particularly "fun," but maybe I maybe I'm not paying attention and/or don't know because I don't work at them.
Great comment. ZIRP is endless stock buybacks and $boomer_rock_band or $expensive_celebrity speaking at your conference. Those are capital owner and executive benefits and don't drive the product or curate new customers.
Tony Hawk at this event is just a marketing stunt and his celebrity can be beneficial to drive engagement, impress potential customers, keep existing customers happy, help with recruiting, etc. Those stunts can get incredible attention. Look at how common celebrities in advertising and endorsements are.
Stock buybacks, having the Moody Blues play your annual meeting or the Rich-dad-poor-dad guy give a speech to execs and play down to their biases doesn't drive marketing or the product. Its what execs enjoy personally and burn through money for these entitlements. Instead this money should be used to give raises to the working class.
Also I'd substitute accountants for MBA's in your comment.
Share buybacks are a capital return to investors. This is a sensible and desirable thing to do in a lot of macro environments. ZIRP may increase the instances of borrowing money to do share buybacks, just like it would increase the propensity to borrow money to do any other valid corporate activity. There were share buybacks in the 80s and 90s when interest rates were quite a bit higher than today.
Adjusted for inflation, there were more buybacks in 2000 than in 2015 and interest rates were quite a bit higher in 2000 than in 2015.
Were companies in other sectors besides so-called "tech" able to disregard profit and just keep hiring as a result of ZIRP and QE. If yes, what are some examples.
QE and ZIRP are deflationary policies because they reduce the amount of interest payments (which are no different from any other transfer payment) paid by the government.
No, they are inflationary policies; fear of deflation was one of the factors motivating them.
> because they reduce the amount of interest payments (which are no different
That's...mostly irrelevant. Yes, government interest payments would be inflationary because some of them go back into the domestic economy, but flooding the domestic economy with money through loose monetary policy is not net deflationary; the reduction in money pumped into the economy in interest payments is far less than the amount of money that is pumped into the economy to effect that reduction.
QE simply swaps one form of government liability (treasuries) for another (reserves).
They pay less interest on reserves.
The effect on the economy of banks holding reserves rather than securities is otherwise negligible because both securities and reserves can be used to satisfy any liquidity requirements, so reserves and securities are functionally identical.
That’s why it’s so dumb that people get in a flap over the idea of the Treasury issuing reserves “out of thin air” but they are fine with the Tresury issuing new securities “out of thin air”.
No I don’t, there was potentially some inflation due to fiscal stimulus but mostly due to supply chain issues. The continuing inflation is caused by interest rate increases, ie. the interest rate sets the inflation rate.
If you were right, Fed policy would drive the nation into an unbreakable positive feedback loop (irrespective, really, of preexisting conditions because the conventional economic levers would always drive the nation the exact opposite way intended) until conventional understanding of monetary policy was abandoned.
The fact that this hasn't happened pretty clearly disproves your understanding: the conventional understanding may be wrong in some way, but its not inverted.
Interesting. I tried to create a Twilio account 2 weeks ago and it was the worse developer experience I've ever had by far.
Like seriously.
They first make you deposit $20 to get started. THEN, they tell you to talk to customer support to activate your account (customer support took forever to reply).
Oh and then I had to fill out like 3 applications and my text messages are still randomly getting blocked - I have no idea why.
To be clear, this is literally just me using Twilio to text myself to test out the API. I'm not some spammer or something. It was impossible to get started.
This is industry self-regulation. See A2P 10DLC. Dealing with it at scale has sucked. If you want to send SMS, it's the price of admission everywhere--not just at Twilio. I know you said you wanted to send yourself an SMS, but you can test without sending using test credentials and magic numbers: https://www.twilio.com/docs/messaging/tutorials/automate-tes...
it is not just SMS, I just recently set up some AWS SES for sending emails (never done this kind of thing before) and boy is it a nightmare to get emails to not be flag as spam these days.
Like SPF, DMARC, DKIM. What the hell how many layers of security do I need to go through to get some emails delivered from a domain I own?
Strongly seconding this (especially as someone who was backstage with Jeff and Tony right before that demo). What's less visible is the impact and influence Jeff has had in enabling leaders and founders to do the right thing. So much of the pressure and industry influence on CEOs is to be short-term thinkers, to ruin their user experience, or to be harmful to workers.
I've seen, both personally and through others who've relied on his example or mentorship, Jeff be a force for good for those who were trying to do right while leading companies. And to even be someone to call in (or call out) a mistake when you make it — which a lot of bigger-name people are way too cowardly to do. He's also spoken up for his city, and for vulnerable communities, when it would have been so easy for someone of his stature to just stay silent.
It's obvious that Jeff is a brilliant technical innovator, but he is just as much of a pioneer of thoughtful and conscientious leadership in an industry that's become woefully bereft of it.
I'm having trouble parsing this against what Twilio does. Are they talking primarily about the Segment acquisition? I primarily know Twilio as an SMS gateway.
Twilio already uses aggressive sales strategies. They make you deposit $20 to test out their API AND THEN they tell you to get approved by talking to customer support.
I was unable to get approved so I guess I'm out $20 for no reason. They have the worst dev experience I've ever seen.
Probably as good at delivering shareholder value as anyone. Probably just didn't want to play ball when investors started asking him to strip out all the value to the customer and put the screws to the employees and purge anything and everything that might be mistaken for humanity and goodness. They love to do that shit and then pretend their new hollowed out strip mine is "lean".
I don't know much about what happened here, but I did meet the early Twilio team (not Jeff, unfortunately) back in 2009 and knew they were something special.
Jeff (and team) deserve a ton of credit for two massive things:
First, changing how people think about devtools. I know Stripe gets a lot of credit, but Twilio was 3 years earlier and really defined how we look at building, marketing and monetizing tools meant for devs. They were early (if not first) to the devrel space, and Jeff's live coding (paired with a phone literally vibrating) was something I had never seen before.
Second, I know a lot of people have lots of opinions about San Francisco, but I have a lot of respect to Jeff for always standing up and fighting for the city that enabled him to build his company. He seems to be a really good person, and is one of the few CEOs I find myself eager to emulate.
Good luck to Jeff, Twilio, and everyone else involved. Jeff built something really special in the early years. And jeffiel, now that you have a bit more time on your hands, hopefully we can finally cross paths!
When we started Iron.io in 2010, there were basically 3 companies at every developer event driving the API-first message: Heroku, Sendgrid, and Twilio. Back then, most thought Heroku (as the Platform) was going to be the one ending up in the public markets. Then they got taken out and Twilio bought Sendgrid. Congrats to Twilio and team for the years of success!
I used iron.io for years. Sad story there I think but I don’t know the details. Seemed like Great service for years then it kind of fell off, the service still worked thankfully. But no new features, and support would take days.
Thanks for using us! We ended up selling the service to private equity, hence the slowdown in features and support. Was an awesome and fun business to build but running a 24/7/365 service just as all the cloud providers were adding similar products was a slog.
I’m personally not a dev, maybe amateur dev, but I am a professional I.T. consultant and sysadmin, and I have used and thoroughly enjoyed Twilio’s tools for years. They are accessible enough for even low-skill amateur devs like me to be able to spin up test programs and functions that do really cool things. I am heartened to hear that my longtime support has gone to a company whose culture and leadership have been worthy. Hoping for the best to everyone involved.
Can't speak for the guy you asked, but I'm approximately his skill-set, and that's what I've used it for.
Long time ago, though; I can't speak to the developer experience now. $20 and contact customer support... What? It used to be easy. Like, create an account and ten minutes later your in business, easy. I used them for a number of (free-tier, I think) personal and (paid-tier) professional projects, and was a very satisfied customer.
I'm somewhat on top of the stock, here's my not financial advice take:
1. Growth rate slowed such that valuations had to come down (went from inevitable overtaking of Salesforce in size, to decades of growth required)
2. Environment -- Cashflow negative meaning another raise was required without fiscal controls and in a high interest environment that's really tough. A return to office end of covid anxiety meant the Covid bubbled stocks are returning to mean. (eg compare zoom has done relatively similar over past 5 yrs)
3. IMO a few execs were absurdly over compensated whilst investor pressure against dillution was targeted to rank and file employees. eg: Eyal Manor earned a reported $42M in compensation (and a $2.5M retention bonus that reading between the lines sounds like hush money), meanwhile ICs were often given below cost of living raises and no refreshers.
1-2 means outside investors had to lower the valuation and 3 meant a combination of dilution and morale hits.
A few other things that could contribute to a slowing growth rate:
1. People build software differently now. There's not as much reliance on text messages (fewer phone apps build built, 2fa via phone is considered dangerous, etc)
2. Gig economy is stabilizing. There was a huge increase in new companies for years, but at this point it feels like we've stalled on new innovations in that space (while a lot of VC-subsidized ones have faded out)
3. There's way more regulations on spam (good for us, bad for Twilio). I think Twilio did as good a job of avoiding spam as anyone could reasonably expect, but the barrier to entry to using Twilio for even reasonable projects now involves the government. Plus with the crackdown on spam (good!), a portion of their business has likely been affected.
I have no idea the breakdown of their revenue, but my understanding is that now they do a lot more than just the SMS they were famous for. Especially with all the companies they bought.
Semi-related to your third point, I do not trust a text message from a company that does not use the shortened phone number system that was popularized by Twilio. It's the easiest way to detect phishing attempts because scammers don't use those.
Why wouldn't you? Anyone and their mother could get a long code number from Twilio for $1/mo, without any kind of verification or KYC process.
Meanwhile, a short code would run you $4500 for three months (IIRC, memory is fuzzy, and it's probably changed), and you had to go through an approval process with all the mobile carriers (that is, Verizon, T-Mobile, etc. had to individually approve the short code) where you explained your use case and promised not to spam.
(Obviously things are different now with the campaign registration and approvals requires even for long code numbers. But short codes are still harder to get, and the approvals more rigorous.)
You’re both pretty much right it looks like he vested all the RSUs in one year so he while he took it all home in 2021 it had probably vested over 4 years, the first 3 when it wasn’t reflected as comp.
I truly hope it's not the divide and sell that activists have been pushing for. The time to sell to CRM or ADBE was during pandemic highs, now both those are probably more interested in AI hype. I think AWS or another cloud provider would be an interesting pairing though, but with Jeff out so does the hopes of an Amazon relationship besides 2023's announcement
They spent a ton of money buying other companies. That’s always capital intense.
Software isn’t capital intensive the way a large industrial factory would be, but it still has unfavorable financial conditions that require raising. You can’t sell software until you’ve built it, so you have to incur a large employee/R&D expense for years until the product is ready. And of course none of that is IP that you can just get a loan against (unlike say, building a factory).
It’s funny to contrast that with the video game publishers. They’ll push to sell things that aren’t even close to finished, make bank, and do it again and again.
I think the common thread with Twilio the sms/sip product and Twilio the CDP / nee Segment is this: businesses outgrow them. Both of them work well for smb and lower midmarket, but as companies grow, become horrendously expensive and essentially strongly encourage migration off. A public company is not a failure, but when your product has a ceiling with your customers, that's painful.
I also had a really annoying experience with Sendgrid post acquisition. I'd used Sendgrid for my first company (as in I personally made the purchase, implemented the apis, and for a long time, was the sole and then admin account). I went to use it for my next company pre website launch and they froze my new account and their customer service was a pita. To be fair, the site wasn't up, but I needed the ability to send emails to publish the site (it's a crucial part of new account flow.) They wouldn't allow me to use sendgrid even though I was happy to share my linkedin, my previous history with their company, etc. We're happy sendinblue customers.
One can continuously grow a stock if they reduce the shares outstanding.
That being said iirc buy backs have notoriously all gone to executives. Essentially they buy back, and then award themselves options to re-dilute, but cannot readily find a source for that. So maybe incorrect.
When a business does a stock buyback, the business receives the stock, not any executive(s).
The business might pay the executive with stock per the board approved compensation package, but a CEO does not wake up and say “I want to give myself 5M shares so let’s do a 5M share buyback”.
A buyback benefits all shareholders equally by reducing supply of the stock and therefore increasing its price.
It's not that executives receive the bought back stock, but that their stock based compensation plans result in no net decrease in the amount of outstanding shares.
My take: ignore the pandemic. The stock price was around $90 before the pandemic hit, which isn't much higher than it is right now. Twilio was basically the perfect remote-work-enabling pandemic company. And the market piled on and thought Twilio was a great place to put money during a global pandemic, when so many other places seemed risky or disastrous.
After mid-2021, that $400+ stock price started looking a little silly. And the broader market downturn in 2022 hit Twilio even harder than it hit the broader market.
And, meanwhile, Twilio's growth numbers -- while still being an unprofitable company! -- look worse than they did at the beginning of 2020. $75 might be generous for how the company is actually doing.
(Full disclosure: former employee for ~10 years, and I still have a few shares left.)
My take: They're too expensive at volume (and they have competitors, just not famous ones) and not specialized enough / not best in class compared to tools like Klaviyo.
This. They're great for small/mid-sized developers, but they price themselves out once you're doing billions of messages a month. At that point companies start looking at aggregators one level down (i.e. closer to the carriers or raw SMTP).
> One issue might be that Microsoft (as ever) launched a milquetoast competitor that sounds the same to a purchasing department in 2020.
AWS (and presumably Google) also provides a suite of telephony services with Chime, SNS, Connect, etc. I assume the strategy now is to sell to/merge with a smaller CSP to provide a competitive portfolio of services.
Not OP, but their approach to devrel was by itself a huge differentiator early on.
We’ve become so accustomed to developer-oriented marketing and programs that it’s easy to forget that Twilio was really at the cutting edge of this movement and should be credited (or at least acknowledged) for the easy on-ramps most developer programs now provide.
Twilio also pushed the envelope in terms of what it means to talk to their developer community. Greg Baugues’ talk titled “Devs and Depression” reached a lot of people who were struggling, and was one of the reasons I personally sought out therapy, and my life is much better for it.
Early Twilio was a very human-oriented company, and I think many developers and developer programs are better for it.
I'm Adam Washington. I was a couple of years behind you, but we bumped into each other socially a few times over the years. As a refresher, I was also the sophomore with the glasses in Shadiow's class that accidentally kicked over the trash can while trying to explain how graphs work.
Back in high school, I thought you were the brightest and chillest guy on the planet. My first Linux install was because I overheard you talking about it in class and I wanted to see what the fuss was about. Anyway, it's been a treat seeing you pop up again after all these years and discovering that my nostalgia lenses were right - you really are that smart and cool.
I was an intern at GigaOM in 2009 (a popular tech blog that ran conferences), and my first memory of Twilio was going to the sales people and trying to convince them to give Twilio a discounted booth because I thought the product was so great. I remember the salesperson laughing and saying "this booth costs more money than they have in their bank account", but there was some extra inventory and we got them the booth.
The early people all just had this vibe of technical-but-not-complicated. It's common now, but at the time it was such a breath of fresh air. They were one of the first companies to pitch "easy of use" (compared to "look at how amazingly complex we are!"). I know this is super obvious now, but back then I had never felt anything like that.
All the people I met (I specifically remember Danielle) were friendly and excited... not in a sales-y way, but in a "I just love what we're doing and want you to, too" way. And again, I know this doesn't feel unique now, but that's because Twilio helped shape how we think about all of this.
I loved their attitude, such as this talk from John Sheehan (https://www.heavybit.com/library/video/runscope-ceo-and-twil...) about how they look at customers. I remember him saying they would fly to any little city that would have them and buy pizza and just hang out. They caught on early that there were so many tech people out there around the country who would become lifelong supporters because of little gestures like this.
Overall, a lot of what I can say about Twilio is super obvious now. But it's kinda like how people watch Friends for the first time in 2023 and say "meh it's a pretty generic sitcom". It's because they created the whole genre and shifted how everything thinks.
> Overall, a lot of what I can say about Twilio is super obvious now. But it's kinda like how people watch Friends for the first time in 2023 and say "meh it's a pretty generic sitcom". It's because they created the whole genre and shifted how everything thinks.
I feel this way about most classic media. Famous movies and books almost always feel underwhelming to me because the notable ideas have been reused and referenced so many times that the original ends up feeling like a retread decades later. Interesting connection to tie this phenomenon to tech marketing and dev relations.
I had the "pleasure" working for Twilio for over 4 years. I cannot tell how much this showed me how you can fake it til you make it in SF.
Twilio tried to expand into Europe and failed miserably. Customers (especially German ones) wanted exact locations of data, exact routes of packet transportation, wanted features Twilio promised on Slides but never delivered.
I was part of at least 4 customer meetings (the biggest in Europe) where the clients just called Senior levels in and told them off.
Twilio was great when it just handled voice and text messaging. It never grew substantially, it never delivered features customers were asking for years. Messy code base, hired product owners with no clue what they should actually build.
Jeff was famous for over-promising and under-delivering. 1 year into my Twilio career, it was clear that the company would fail hard. Colleagues and I had bets on when Jeff will be fired or the company sold. Well, the last few months have been telling.
A sad story, since they had a great core product, really smart people, great people working there. But especially through the pandemic, they grew an insane amount without actually building anything of substance.
this is pretty much my take as well - but as a non-employee - I was a big fan and user of twilio when they first came out, even attended the very first few twiliocon conferences in SF, (mostly developer focused) where they would announce and release new features - lots of excitement as new things got announced and rolled out during the annual conferences.
Then after not very long, you would goto the conferences where they would make announcements about what is coming, but no real timelines attached and some things that were announced, never really materialized - or not fast enough etc.
Then they started diversify like crazy into other areas, unrelated, and I think they really lost their focus - stopped using them (99% stopped) a long time ago for those reasons.
I'm not the OP, but agree with their assessment and stayed 3.5 years despite that. For me, the reason was the vesting schedule: 4 years with a 1 year cliff.
You join and are granted 400000 options at $10 strike and stock is worth $10
2 years in and the stock price is now $110
You think the company is terribly run and the stock with crash at this point. However if you quit, you lose the 200000 unvested options worth $2M on paper
Even if the stock crashes to $20 they are worth $200k
Hard to find a better paying job in that situation until the options are fully vested
I mean, you can take it quarter by quarter. If you get your vest and (even if you sell them immediately) the value is worth it to you, you'll probably stick around for another quarter to get the next one.
You don't just say on day 1, "I don't think the company is going anywhere, but I'm committing to staying another 4 years".
I was in a similar situation. A year into a job with a large company, I realized the company had issues and that I didn't like most of the people I worked with.
I stayed for ~1 year after I realized I needed to get out: At the time I was getting paid very well, had very low expenses, and was saving to quit my job and start my own company.
My original plan was to stay a few months longer to build up some more savings, but "things happened" inside the company. I was re-assigned to a horrible manager; I hunted around for another assignment (on the advice of my boss's boss,) but that was going to be Flex-based. (And I bet correctly that Flex was going to fail in the marketplace.) I decided that I was better off quitting and self-teaching myself HTML + Javascript instead of getting paid to learn Flex. However, I could have stayed for a 2-3 more years, worked in Flex, made a boatload of money, and selectively applied for jobs elsewhere.
> One year into it you knew the company was going to fail yet you stayed on for 3 more years?
There's a lot of risk in changing jobs: If you "have a good thing going," it's best to bide your time until a better thing comes along. Interviewing is quite time consuming too, so don't assume that someone can just casually make a few phone calls and walk away with a "better" job. (This is especially the case if you have kids, a house, a mortgage, and a significant other who has their own career.)
Job mobility declines significantly with marriage, kids, and mortgage. I've toughed it out before, mostly to keep the good healthcare benefits. (This was prior to ACA eliminating the preexisting conditions BS. We didn't want the hassle, uncertainty of changing insurance during a pregnancy.)
Also, it's hard to job hunt when you're already over worked, both at home and the office.
Also, the devil you know. Every new job is a gamble. After a while, all the jobs kinda smell the same. So what's the point in playing frogger?
For starters, actually trying to deliver what they promised? Get the actual hard, boring job done bigger clients wanted. The not-sexy work behind the scenes. Main problem is that it doesn't look good on paper, and Twilio hired an absolute insane amount of people.
My guess is they profited _a lot_ from the crypto hype. Exchanges sprung up right, left and centre and they all needed customer call centres etc. So Twilio grew through that. Saw super high growth and thought: All is well. All the while the "real" customers didn't get the features they needed, and quit Twilio after a 6 month trial period.
The decline of Twilio's position has been as pretty clear for the last 18 months now, and has been a topic of conversation longer than that. Twilio never had the margins or control of their environment to nearly the degree you need to have in order to maintain software monopoly levels of growth over time.
Most of Twilio's business has been built on reselling network access purchased via SMS consolidators. These are companies who, decades ago, got their hardware installed inside the networks of the major phone carriers. This allows them direct access to send/receive SMSs. Twilio never really tried to own the network layer and these companies continued to demand higher and higher tolls for access. Short codes are a very good example of this. Twilio spent a lot of time and money trying to sew up access to those short codes.
On top of all that, high volume customers would move directly to these consolidators. Sometimes Twilio would keep some portion of the business if the sender used a round robin model to distribute sends, but often they didn't. OpenMarket and a handful of others were the goto providers at scale.
Add on to this the overall decline of the utility of SMS. Even as SMS volumes increased, they have not increased at the same rate as messaging overall. ie: other channels like iMessage and WhatsApp continue to pull volumes.
Cue Twilio's attempt to go up market. Flex and the purchase of Sendgrid were the best examples of this. Could CPaaS work for Twilio as a business model? I think we've seen so many fits and starts with the Flex product line and the integration of Sendgrid that it seemed like perhaps buying their way in to that market wasn't panning out.
Finally, as seen in the last year, the culture just seems to have gone off the rails at some point. [1] I don't know Jeff, but my respect for him is sky high. I've read all his writing over the years and he's been hugely influential for an entire generation of founders.
Unfortunately this seems like a bit of a hasty departure. I hope it isn't, but the choice of replacement CEO screams caretaker-CEO rather than shrewd strategic move.
Another commenter mentioned Stripe [2] and how they get a lot of credit for advancing DevTools. I agree that Twilio did it first and I think paved the way. Jeff Lawson and Twilio deserve more credit. "Ask your developer" was not a small thing at all.
I also think Stripe very likely is in a very similar position, but they are earlier in their cycle and they've avoided the scrutiny of being a public company. Credit card processors are gatekeepers and fully dominate in their markets. Stripe serves a purpose for them and dramatically improves access to their networks via great tooling and abstractions, but there is still a fixed cost toll to pay and what that toll is cannot be static for interminable time. Is Stripe in the "Commerce" market like Twilio is in the "Communications" market, or are they in the "payments" market, like Twilio is in the "SMS" market? (or somesuch)
In the early days of Twilio, carriers laughed at what we were doing. It didn't help that most of the people at Twilio pre-2014 didn't speak much "telecom." But to your point, it was tough to rely on these carriers who thought Twilio would be gone in a few years so they didn't put much stock in ensuring the infrastructure was redundant and robust.
I was on several calls with providers begging them to put us on a more robust network. Especially in years when there was an election. In those early years, we had one customer doing more minutes than our entire customer base. In fact, at an early Twiliocon (pre-Signal) John and Jeff had to help build out an entirely separate environment for them because it was dragging everyone else down.
My point is that the early days were definitely the "Draw the Owl" days. We were figuring out things on the fly. Carriers were dubious and it was tough to get things working consistently. However, by 2015 those same carriers were developing APIs of their own.
Twilio changed the game for the telecommunications industry. Two years before joining Twilio I was putting in large-scale Avaya systems. The fact that I wrote four lines of code to make a phone ring blew my mind. Twilio and Jeff created something special. It's sad to see his run come to an end, but every company needs to adapt to the changing times. This is just Twilio's time to adapt.
> In those early years, we had one customer doing more minutes than our entire customer base. In fact, at an early Twiliocon (pre-Signal) John and Jeff had to help build out an entirely separate environment for them because it was dragging everyone else down.
As an early large customer, I wonder if that was me... sorry for messing up everyone else ;) I do remember some issues at times, but nothing we didn't see with other voice and SMS providers. Well, other providers didn't have an online log browser, so I never had trouble with browsing logs their logs.
Twiml was much easier to use than the other 'programatic voice' apis at the time, and I never had time to figure out how to run calls on sip directly. As I recall, it didn't take much time to setup voice calls, and then boom. It was helpful that quality was good and support was helpful when there were destinations with poor results.
Fwiw I think a key difference in stripe vs twilio in your example is that stripe has 2 levers that twilio doesn't have good analogs to:
- stripe can be a "financial home" for many of its customers and build higher-margin pockets of software functionality, using easy payments as an on-ramp. See: stripe billing, radar, sigma, connect, etc.
- stripe is more likely to be able to "swap out" the credit card rails than twilio would be able to "swap out" sms. If the financial ecosystem evolves to make eg debit cards or any other kind of payment easier, stripe can simply add them as payment methods, as they already do for non-CC payment types (most notable outside of the US). So stripe is already at the abstraction level of "move money from customer to me" instead of "run their CC".
I think those are good points and valid, but Twilio definitly had equivalent arguments in their own product.
Encumbents manage scale very very well and historically they tend to come to a market late. While Stripe is rushing up the value chain, the issuers are just slowly lumbering around.
Billing, Radar, Sigma, Connect are all very well built products which drive usage of their core revenue generator. I suspect the revenue mix at Stripe is still largely payment processing. Voice minutes and SMSs on a carriers network, or authorizations and settlements on an issuer network.
I am not saying Stripe is doomed, far from it, but it's a non trival problem to solve over the long term and the default state is attrition. I think Twilio is a very good example of how difficult this can be.
> On top of all that, high volume customers would move directly to these consolidators.
This is pretty key to understanding Twilio's prospects as a business. In my experience, they are fantastically easy to integrate at first.
But they come with a cost that blows up your financial model if your product is any kind of high-volume use case, or if SMS is factored in as a direct cost and you're talking to investors about unit economics. At some point you have to get off of them and onto a cheaper-per-SMS solution, even if it costs more dev hours to maintain.
When I joined the Twilio Developer Evangelism team in 2014, we spent a lot of our onboarding practicing the "five minute demo" where we live-code a Twilio app from scratch. I thought this was dumb, mostly because live-coding is so damn hard.
Six weeks into the job I watched Jeff live-code a Twilio app in front of 10,000 people at IBM Connect. It was as if he was saying to all of us, "Yeah, live-coding is hard. And if I can do this in front of 10,000 people, you can do it at your local Ruby meetup."
It was the first of many, many times over my nine years that Jeff led by example, set the bar, and pushed us all to reach levels we didn't know we were capable of. Working under Jeff's leadership was the privilege of a career.
I worked at Twilio from 2014-2023 and had an incredible experience during those 9 years, including all of my interactions with Jeff.
One of my favorite moments was running into Jeff in the hallway at our Beale Street office just before he had to do a quarterly earnings call after we went public. I said "good luck on the earnings call" and Jeff said thanks then asked what happened to a link to a specific Stack Overflow question/answer from one of our docs pages that got removed. He had just been building an application and felt like that answer was particularly helpful for context in a certain programming language, and was surprised it was removed.
Jeff's always been software developer at heart even though he had a ton of non-dev responsibilities. There are definitely advantages and disadvantages in that mindset! But he created a tremendous company along the way and I wouldn't change working there for anywhere else during those years.
I joined Twilio in May '11 the week of the private launch of Twilio Client. I was #18 or so.
My first day, we got briefings on what it was, what it will do, and then had to finish docs and re-arrange the office for our top customers. (At that stage, most people knew them by name. Shout out patio11!)
Since I knew nothing and the docs were.. weak, I decided to take out the garbage. I grabbed the bags and asked where the dumpster was. Jeff Lawson stopped me and asked if I had an office key card to get back in. Oops, nope. So he grabbed a bag and we took it out together.
So yes, Jeff opened doors for me. ;)
Despite the last year or so of chaos, he founded and built a company that redefined telecomm specifically and tech gtm as a whole. Not a bad track record.
And the infamous five minute demo.. we drilled on that constantly. At my peak (2013), I was giving it 2-3 times a week in front of small groups, with the occasional sales reps, and in front of huge events.
My favorite times were:
- for one of Bob Metcalfe's courses at UT Austin. Yes, that Bob Metcalfe, the co-creator of ethernet. I talked about the origin of Metcalfe's Law here too: https://news.ycombinator.com/item?id=35259442
- 1:1 for Werner Vogels at SXSW. I gave it to one of his senior guys and he said "wow, this is great, let me go get Werner" which was intimidating as f.. a lot. But I managed to nail it.
Keep in mind his voting structure changed in May meaning he lost some shareholder power.
> Its use of supervoting shares, which gives CEO and co-founder Jeff Lawson a voting stake of 21.8% even though he owns only 3.7% of the stock, [1]
No derogatory remarks intended to Jeff, Jeff certainly has had great moments, but Kho is also a fantastic leader and capital allocator, who's made some truly uncanny calls (like raising in the market near the top,and share buy back near the bottom). I think Kho is the right person for the job in the times that Twilio finds themselves. It's something I've hoped for for years, as a shareholder. Jeff deserves praise for the humility to step down and promote from within a well groomed and talented successor.
Any exec who actually tries to sell the stock high, and buy it low is a winner in my book.
Most just follow the crowd and do shareholder dilutive buybacks at nosebleed valuations.
If you can buy a long duration US treasury yielding more than twice what your shares yield, maybe stop to think before doing any buybacks.
Though I've written it up to mostly short term-ism towards increasing their own compensation through pressuring share price in the immediate term. The alternative is that all these CFOs and others are financially illiterate or incompetent
Reminded me of another point on the board for Kho, He was smart enough to grab a billion in 10yr bonds at like 3% which was genius for the growth rate (if you can grow money at 10% then you should take every penny you can get below that).
The only party he missed was putting our cash reserves in BTC. (which is an inside joke). It would have made the money like $4-5B based on the time of the suggestion. I think investors will be happy to hear he flatly outright said no to that. It looked like a missed opportunity (at $64k)... until it didn't. (back at $16k)
Agree with this. For folks not familiar with Twilio leadership, I would liken Kho to Twilio's version of Tim Cook. For the size and stage of growth that Twilio's at, he's the best possible replacement for Jeff.
"Twilio Inc. Chief Executive Officer Jeff Lawson is stepping down from leading the software company he co-founded amid slowing sales growth and pressure from activist investors."
“The move is not likely to stave off the activists at Anson Funds and Legion Partners. Both are pushing for the company to sell itself or completely divest its data & applications business, CNBC previously reported.”
What a shit sandwich. Not everything needs to be a hockey stick. There's is an angle of the growth line that should not be exceeded because above that level of growth seldom is a good situation for the consumer.
The problem is that Twilio is not profitable. They wouldn't need to show a hockey stick if they were. Investor-subsidized, non-profitable companies have to sell growth to their investors because they have no other fundamental to point to.
Indeed, either take the investment and the dragons that will come to burn your village or grow slow and own your future (Basecamp/37signals), but make peace with that you’re always going to be small (but it’ll at least be yours).
instead of posting a poorly informed take, you should go and have a look at their list of product offerings. They havent been just a "notification API" for a long time now.
What a great run. I remember the IPO party in 2016, very early in my career, and being in disbelief that a texting API was used by so many people. It was my first time writing code for systems that operated at _real scale_. While the last few years have been a bit rocky, you can't understate the impact that jeffiel had on the developer tools ecosystem.
Reading this and related stories, seems to be related to activist investor pressure. Reading into that, seems that activist investors are pushing Twilio to divest from their Data & Applications business. How I understand it Twilio has moved into "customer engagement" from their initial core business and investors aren't happy with the direction or returns from that business unit.
I worked at twilio when they were a series B company and Jeff personally did the on boardings. I think it was the only company I've worked at where I felt that every engineer was a super star. I've followed their career since then, and they've gone on to do phenomenal work. My opinion is that they had very weak leadership below the C-suite. We brought on one of the founders of skype, and after having lunch with him all I could think is how good he is at talking and how little value he'll deliver. I felt the same about the core engineering managers, and they went on to screw over a lot of the early talent - that now thrives at top companies. Regardless, Jeff was amazing. He was the sweetest guy and use to throw bbqs at his home. How fast the years go by.
Seems like such a common failure mode - early team proves pmf, then founders go on and hire substandard management who alienate early folks, hire their puppets/friends and proceed to ruin everything. I've seen it personally a few times now and still not quite sure why otherwise smart founders keep falling for it.
I used twilio for years until in August of 2023 they started blocking all my text messages, then they wanted you to describe what you're using it for and you had to pay money to fill out a form to tell them what you're using the text messages for.... then they would deny that and then you basically can't use twilio, or pay them to fill out the form again so they can deny you again.... This is for outbound SMS (payment notifications to customers) so I wound up writing an Android application that runs on a phone that just sends out SMS messages using an API talking to a server..... I'm paying $8 a month to Tello now which is about 1/5 the amount of money that I was paying to twilio so I'm glad that I switched..... but I think they really screwed up recently.
This is likely because of industry regulations around A2P (application-to-person ) messaging that had a due date of August 31, 2023.
It's not just Twilio, you would have experienced this with nearly every SMS API provider. Across the different vendors I work with, I received numerous emails from each one advising me to come into compliance or risk my messages being rejected.
> It's not just Twilio, you would have experienced this with nearly every SMS API provider. Across the different vendors I work with, I received numerous emails from each one advising me to come into compliance or risk my messages being rejected.
From what I can tell, the telcos aren't performing any enforcement, even tho the deadlines and extensions are long past. Not to say they won't but the endeavor seems to have a stall vibe going on.
Some of that might be related to having major mass-campaign requirements placed on small biz who occasionally send a handful of texts (often non-sales) from their workstation phone apps.
At least I hope this is why it has stalled. Sending a few texts during a customer service session shouldn't be regulated as if it were a blast of 1M SMS ads.
The blocking was 100% not Twilio’s fault it was 100% bad actors and pressure from congress. Also we have three major carriers now in the US they needed to act fast in August since congress was going to go back I session in September to force this. So the carriers wanted to be able to say to congress see we are already taking care of the spam issue … see https://www.campaignregistry.com/. The single monopoly in charge of the regulations
> I used twilio for years until in August of 2023 they started blocking all my text messages,
New telco industry texting requirements came into play. In short, US biz are required to register with The Campaign Registry and pay regular fees if they want to do any (as in 1+) software text comms.
It can be onerous for not-large biz. Twillo took point early-on (inserting themselves into the administration, IIRC) and Twillo then got a lot of heat from their users - even tho the requirements originated from the telcos.
Somewhat surprising/disappointing to me was that now you can't even send SMS to a number that initiates the conversation--this would seem to be a pretty clear opt-in indicator. Because of that, I couldn't find a way (through Twilio) to get around the registration requirements just to send SMS to my own number for development purposes to try some things out. The registration workflow and UX is also comically terrible and confusing.
It's a shame as I think there are some legit non-spam use cases for SMS as a messaging platform, but considering you now seemingly need to pay, fill out a bunch of annoying/buggy forms, and wait for days to who-knows-how-long before sending a single message in development, I'd say it's been pretty well destroyed as anything a dev would ever play around with. Who's going to do all that before writing a line of code?
The time I wasted waiting for twilio to deny my reasoning for sending an SMS message to One of my customers, paying them to do this mind you, was about the same amount of time it took me to write an Android application that sent out SMS messages by reading from a custom API on one of my servers... I probably should have done that in the beginning it would have been a lot less money in the long run.
I think your frustration is reasonable. The telcos are favoring major marketing companies by unreasonably imposing big biz requirements on small biz and indy devs (through platforms like Twillo)
That bad UX is being supplied by The Campaign Registry org.
I do recall Twillo performing TCR's tasks in the beginning (applications, registration, etc) but only until TCR was spun up. It's all on TCR now.
They serve big businesses now. They don't want small players coming in with potentially abusive behavior. Twilio worked hard to build its relationships with carriers and doesn't want to be dragged down by spam.
Hats off to a legend. Twilio was The Beatles to the devtools space. They defined modern devrel and the bottom-up/PLG GTM motion. He also disproved would-be investors who said developers would never pay for an API; in fact they’d prefer that to building something only to get rug-pulled when a company decided their free API was no longer strategic for them.
And while you hear a lot about ruthless but effective asshole CEOs, Jeff happens to be a brilliant executive and a great human all at the same time.
I always thought AWS would end up buying them, of course this was 5+ years ago when I had that thought - not so sure anymore ... but I do agree, I don't think they will remain a company as-is.
I worked at Twilio from 2011 to 2022, and it was quite the amazing ride, especially for the first four or five years. Twilio basically wrote the book on API-first businesses, and on how to court developers to use and love a product, and evangelize that product to less-than-technical management types. While Jeff wasn't all that involved in the technical side of things by the time I joined, he still kept his engineering chops up, and it was always fun to see him live-coding Twilio apps on conference stages.
I was disappointed in Twilio for the last several years I was there. What had started off as an engineering (and product) focused company devolved into being driven by sales. We put out some products that were half-baked from an engineering perspective, and it showed: missing or buggy features, downtime, and unfulfilled promises to customers that sales/product made with barely perfunctory consultation with engineering. IMO it really hurt the company's reputation. I remembered a time when mentions of Twilio in tech circles would come with praise and even awe; more recently complaints seem to have overtaken the good vibes.
The "Ask Your Developer" billboard on US-101 as you entered SF was iconic. I loved that billboard; it perfectly encapsulated what the company stood for and illustrated why I was so happy there. For a while it was changed to something about reducing customer acquisition costs, a big red flag. More recently, it says some meaningless nonsense about "digital greatness" and "customer AI". That kind of shift tells me everything I need to know about where things have headed.
Ok, time to stop being so negative... having said all that, I wouldn't trade my time there for anything. I learned more than I thought possible, worked with a ton of people who I respect heavily, made many lifelong friends... it was a life-changing experience. Jeff was a big part of that, and I'll always be thankful to him, Evan, and John for creating a place where I could thrive and grow.
If you want to see Jeff Lawson in action, you should watch a great talk of him about company culture and values [1]. Even though I'm a programmer and usually don't think too hard about such topics, I can fully relate to his ideas. He's sharing the process of how they arrived at twilio's company values [2], which really are exceptional.
Usually company values are just written down as a checklist somewhere, which you once read and then forget about. But twilio's values are fun to read, think about and easy to follow.
All of the media clouds that did not include telephony, were always bad business cases, sometimes got repeatedly sold and resold like a proverbial hot potato, see TokBox.
Twilio did include telephony and was originally built as telephony-only provider, so it really stood out and was a lot more sustainable as a business than anybody else.
But, importance of telephony is falling. When was the last time you dialed-in to a Zoom conference? Without that, what's left of telephony? Just the 2FA SMSes.
I believe long term, providers like Twilio will become very thin layers of indirection to aggregate together underlying phone operator services, and will be mostly owner by those phone operators themselves, like Vonage now owns Nexmo, Twilio's direct competitor. Nexmo's API makes a lot more sense than Twilio's by the way, and is a true pleasure to use.
They have not adequately funded the video product for a very long time. Other companies built out better infrastructure and a much broader range of features. The market also turned out to be smaller and differently structured than all of us thought. (I am a co-founder of a company that competes with -- though also predated -- Twilio Video.)
I think with the US Carriers mandating proper campaign registration process for texting, even small number of testing it has taken a huge toll on their support. I think earning for last year q4 are about to be lower then expected
Twilio is great and super frustrating at the same time. I've run into outdated or missing documentation, and plenty of low hanging fruit UI improvements that get ignored. They seem to be asleep at the wheel at this point.
As someone who has loved Twilio from the early days and have built many apps for small and enterprise cases as well as fully embraced Flex in the customer experience space, I really have no idea what the hell they are doing now. Not sure if they are right sizing after trying to capture markets like video and Contact Center but it seems like even successful sales teams are let go now so curios where they emerge from this.
I haven't used twillo since 2014 and I don't use twillo at company. I have recently tried to use it for my own projects and I have not had a good time with the product. I was able to set things up fine with the docs but the ui and the support didn't seem to understand the hobbyist concept. I could not get my number registered for texting again and support did not care. Example: I cant release the number I have because it has an emergency address I need to remove. I cant find the ui to remove the address. I can only add address. While the ui banner says "Please add an emergency address to this phone number or you may incure a $75.00 charge per emergency call."
I am just waiting for my minimum required balance to be eating up by fees i dont understand. I have moved on to a chat service. I wish them luck moving forward.
We will now watch the enshittification and bedbathandbeyonding of Twilio.
I think this is especially sad as Twilio really was a reflection of the purity of product and engineering coming together to make more than the parts.
I can’t think of a better leader at the intersection of people and technology than Jeff Lawson.
I think Twilio has a unique opportunity to lead in AI if they kept their Hacker spirit. Unfortunately the fatal blunder here was that they signed up for this outcome via IPO. Not much better being private under PE, however it was doomed to this fate the moment they went public.
All that said, congrats Jeff (jeffiel) for doing such an amazing job and holding on this long.
Right now: voice-bot telephony. So, immediately have a twilio number that you can call/text and talk to a GPT much like I do with the ChatGPT app interface. This rapidly could couple into actions API for doordash amazon etc…so Twilio would be handling all this scalable AI-Telephony data. They have the infrastructure and engineering for it.
Long term: own the infrastructure for infinitely scaling call centers for any task you would need to do over sms/gsm voice
Twilio is in a weird spot. They are so cheap that it's very easy to build a successful company on top of their APIs, and choosing their APIs is a no brainer.
They probably need to go vertical and capture some of the value their users are generating to have the kind of revenue investors want.
I've been reading about the last year of twilio w/regard to layoffs and what not. Mostly trying to figure out what teams had layoffs, so down a rabbit hole.
This article [1] says "Anson and Legion [[2 investors]] have pushed Twilio to sell the Data and Applications unit, if not the whole company. Anson and Legion have both amassed individual stakes of around $50 million"
Twilios marketcap is 13.33bn. Why do 2 investment groups that own a collective of $100m twilio have so much power that they can push for layoffs or SELLING the WHOLE company?
They want twilio to sell a group that is 20% of their revenue. 20% of their revenue based on a 2023 $4bn would be around $800m or so. Twilio is an 8k employee company.. Is $50m in stock so high on the food chain that you get critical voting rights? That's nothing to an 8k large company.
Edit: Ok I'm learning about "Activist Investing" now and I'm pretty sure as opposed to that really nice seeming name it's corporate vultures who try to take over the board and push a company to do whatever they're doing with Bed Bath and Beyond and all those.
It was ONE Portfolio Manager who went from Legion to Anson and brought Twilio into their portfolio at both companies, at $50m each.
He launched campaigns at Kohls, BB&B, Twilio, Nutanix and SurveyMonkey at least according to this article.
And for anyone curious about Activist Investing - Moral of the story once you own 5% you get a form that notifies the board you own 5% and they send in a form to the SEC with all their wants/complaints: https://www.forbes.com/sites/emilywashburn/2023/02/03/whats-...
I love Twillio's products. As a developer turned product manager, I always find it striking that many teams try to reinvent the wheel while Twilio provides a suitable solution with a relatively favorable ROI.
Anyway, I wish the best of luck to Jeff. I consider his book Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century to be one of the must-read books for founders.
> I always find it striking that many teams try to reinvent the wheel while Twilio provides a suitable solution with a relatively favorable ROI.
This was not my experience. The gulf in pricing between Twilio's raw STUN/TURN solution (which they had clearly gone to great lengths to keep hidden amongst their product offerings) and their batteries-included WebRTC API solution was so vast it was almost comical. At a certain scale, a company could save maybe millions of dollars a year at the cost of a day or two of extra engineering effort. They were far from averse to the strategy of looting their customers.
I met Jeff back in 2011 when I was considering moving to SF. Although I didn't end up at Twilio, I distinctly remember thinking I'd be happy to work for him. His original Twilio demos were a big part in convincing me to make the move to working at a proper startup.
I wouldn't be happy about that. The innovation generally stops when the folks who really know the customer and have the audacity to pull the trigger on big changes are replaced.
not good for twilio. probably will bounce up in the short run as they increase financial discipline. (ie cut projects and teams). but then its not clear to me what their tech/product vision is going forward. and their core markets of sms and voip are slowly being replaced by other channels. (IE companies like Stream for chat, braze for notifications & marketing, authy for 2fa etc)
Shareholders have been critical of Twilio's performance, and therefore Jeff Lawson over the last year or two though... They're in a difficult place. They don't have the margins of a SAAS company and they've been losing a lot of money.
This was fine in a low interest rate environment where investors are willing to pay up for growth, but when that changed investors wanted them to cut costs and show a path to profitability. As a result Twilio was forced to do large layoffs and refocus the business on products with higher margins.
Perhaps Jeff just didn't want to run the type of business Twilio needs to become in this new environment. He doesn't strike me as the kind of person who gets passionate about running a mature business that needs to focus on optimising profit margins above all else. I he think prefers to get stuck in and build things cool things, and for better or worse that's not where Twilio is anymore.
> He doesn't strike me as the kind of person who gets passionate about running a mature business that needs to focus on optimising profit margins above all else.
There is optimizing profit margins, and there is not losing hundreds of millions of dollars per year, year after year.
The large GAAP loses comes from dilution – mostly in the form of stock based comp. In theory if growth exceeds dilution then investors are still owning an appreciating asset, and if the stock is richly valued (as TWLO was) then it makes sense to fund that growth with capital rather than debt.
But yeah, as a shareholder I felt their stock based comp was egregiously high and it took management a little too long to realise we're in a new world and things needed to change... A side point, but that's actually why I invested in TWLO because the stock got so beat up and their SBC was so excessive that it was kinda obvious that things were going to need to change and the market would react to that positively.
The markets seem to be reacting favourably to this news and again I think that's because there was an assumption that Jeff Lawson was largely to blame for the lack of focus on profit optimisation.
Personally I think Jeff is a great CEO though and I didn't want to see him go. I just wanted him to make some tough decisions to stop the burn – which more recently he seemed to be doing. While I do think they need to be more finance minded in this next stage of the business, I would doubt whether a developer focused tech company like Twilio will benefit much from a managerial leader like Shipchandler. We've seen this mistake made repeatedly by tech companies in the past.
How do folks respond to the notion Twilio could be replaced by KeePass or to what extent is that true/untrue in terms of 2FA? Not sure what they do outside of that
> Shipchandler has over 25 years of experience growing businesses and driving financial performance across global, public organizations. Prior to Twilio, Khozema spent over two decades at GE where he drove operating excellence in GE’s high tech aviation division, plus accelerated growth in the Middle East region.
I wouldn't be too enthused about him running a software-focused company. His experience yells "generic businessman brought in by investors to squeeze more profit".
> He has a deep understanding of Twilio’s business, operations and culture, having most recently served as President of Twilio Communications, and previously as Twilio’s Chief Operating Officer and Chief Financial Officer.
I agree that this is not a move I am happy to see. I hope I am proven wrong. I have been struggling with my love of Twilio. For years they have been one of my favorite tech companies, but I have been really struggling with them and their products lately. It feels like they have lost their core mission.
To be fair, Khozema joined Twilio as CFO more than 5 years ago; it's not like he was brought in externally and knows nothing about the business.
But yeah: Jeff had been working toward GAAP profitability for a while now, but was unable to deliver.
I have my own feelings and biases about the company's trajectory over the past years (I worked there from 2011 until 2022), but ultimately a) Jeff lost his super-voting shares last summer, b) he didn't deliver on profitability, c) growth numbers have been unimpressive for a while now. Activist investors have been saber-rattling for most of the past year. Of course Jeff was going to get forced out, sooner or later.
I worked at Twilio for 4 years and it was one of the highlights of my career. End of an era, for sure. Thanks Jeff for trying to build an anti-racist company even when it upset some of our investors.
Is the typeface/font being used here glitch for others, too? It looks kinda like a dyslexic optimized font where certain characters have different weights.
I know nothing about this board, but I imagine he must be the absolute best person for the job, because they probably seriously considered the downsides having to write up that statement.
If it was the other one, he'd be literally dead on arrival, so I guess that limits the potential confusion a bit. But yeah, I doubt he uses his full first name much these days.
“Jeff Epstein Appointed Chair of the Twilio Board of Directors”
That’s an unfortunate name to have. I’ve always wondered how people handle when this happens. If it’s as big a deal as I feel it would be if it were me.
He created an environment where (at our best) we could have fun doing work that had a real impact, and we could it with people we enjoyed doing the work with. He pushed us to be creative to authentically empower and inspire developers. Wanna build a video game that teaches developers how to code and use Twilio? Let's try it! Wanna build an AI application with Tony Hawk and have Tony Hawk debug the code live on stage? Sure!
And Jeff would always be spending time with developer tools and Twilio's products himself, to the point that he could live code at the drop of a hat to show off what we'd been working on. This meant his own understanding of developers and their problems never ceased to amaze me.
But more than all of that, he was a rare CEO that led with empathy, humility and care.
Thank you, jeffiel. We can't wait to see what you build next.