Twilio acquired Segment for $3.2 billion in an all-stock deal. I was Segment's 4th engineering hire.

I'd finished working at 37signals at my one year Prototyper gig. I worked with Jason Fried, DHH, and Ryan Singer. Every time I went out for dinner with people from the company they would ask me how it was working with Ryan Singer, and then go into their stories about him. I liked working with Jason but I wasn't surprised when 37signals imploded. Two people ruled top-down with complete control, and the company was loaded with history and drama.

I knew what I wanted next: a startup where my work mattered, people my own age, open-source, B2B infrastructure, and no more Rails.

I wasn't in a rush. I thought this would be a good time to interview with the big tech companies: Google, Apple, and Facebook. I didn't want to work at these companies, working on a piece of a piece of a piece. But I wanted to experience their interview process, see if I'd pass their tests, and get an offer against the odds. At the time, these companies were against hiring people without degrees. These companies told you exactly what they were going to interview you on, and what resources to study—The Algorithm Design Manual was most useful. I flew out to the Bay Area and had a busy few days where I interviewed with one company a day. When I checked into the airport, the kiosk had a custom welcome screen because Google had booked my ticket. The interviews surprised me with how relevant and practical they were. One interview had me iterating over JSON, aggregating data. Another interview had me design the storage layer for Google Ads. I flew home. They sent over offers. I declined. I'd proved what I wanted to prove.

I talked with Segment. I flew out again to interview with them, and a couple other companies. Peter picked me up from the airport and we drove across the Golden Gate Bridge out to the Marin Headlands. I interviewed the next day. It was at their first office at 2nd and Bryant St, which was a converted 1 bedroom apartment. On the wall was a big screen TV with a Grafana dashboard with metrics on the API and the company's finances. Their interview was to create a small app that talked to a server Calvin had written—request, parse, respond. I had it implemented in about 5 minutes. Calvin took a peek and laughed and said Nice! It felt like two guys hacking on a side project. We hung out in the office for a bit and went out for a team dinner. I flew home. Jenn sent me the offer and said "By the way, we're going to Australia next week. We still have time to get you a ticket."

I had 36 hours straight of travelling: Toronto to Vancouver to Sydney to Melbourne to Lord Somers Camp. It's wild to see the sun rise and set all in the same flight. I installed Civilization 5 for the flight to Sydney, I'd never played the series. I played Civilization for over 12 hours straight.

The first few days in Australia, we attended Campjs, a 3-day tech retreat. The campsite's main area was reserved for hacking. Scheduled content took place in other rooms or outside. The final night was reserved for people to demonstrate what they built or learned at the event. I wish this setup were the standard for conferences.

After the retreat we flew to Sydney and Anthony—a native Aussie—drove all 12 of us in a huge van to the Blue Mountains. We stayed at a house for a few days, went on a hike, and saw the Jenolan Caves. Then we drove back to Sydney, stopping at a zoo along the way, and stayed in a hotel in Coogee. One day we went to Bondi Beach for lunch at an upscale restaurant, a nearby table had a group of women who looked like the Real Housewives of Bondi. They thought we were a football team.

Another fun trip was to NYC for Brooklyn Beta. The venue was the Duggal Greenhouse in the Brooklyn Navy Yard. At night we went out for karaoke and bar hopping. One night Anthony went too hard on the dance floor, did the worm, and split his chin open. He and Ian went to the hospital to get stitched up. The next day we drove to the airport together to head home. They went to the east side of the terminal and I went to the west side of the terminal but we met in the middle because our gates were on opposite sides.

One day my bank called me asking what to do with the wire they just received for me, as it was abnormally large. The number they told me was nearly my yearly salary. I felt my stomach drop, then Jenn called—she'd put a zero on the end of my monthly wire by mistake. I wired the money back and everything was okay. Shortly after, Segment automated its payroll.

I lived in a building at Queen and Spadina. Textile shop on the street, a gym on the second floor, a handful of apartments above. My neighbour and I walked in together and started up the stairs. I'm headed to SF tomorrow. Me too. What flight. Eight. Same. Where you sitting. We checked our phones. Same row. Him on one side of the aisle, me on the other.

Almost everyone was around the same age, with no kids. Although I lived in Toronto, I flew to SF almost every month. We'd play Diplomacy or Settlers of Catan after work. We hung out during the weekends—went for hikes, went to the park, went to concerts. We'd have impromptu nerf gun fights in the office. But most of all we got shit done. Segment was the most fun place I worked at and everyone who worked there during this time says the same thing.

We threw two office parties when we raised our series A. The couth party for the investors. And the uncouth party for friends and family, the next night. The idea was not to fill up the couth party and get too rowdy. The problem was nobody wanted to go to the couth party.

Segment worked over email, using team mailing lists. We held daily standups by emailing [email protected] your plan for the day. Everyone shared in the standup—CEO, sales, design, engineering. New customer sign ups triggered an email to the team and [email protected]. We sent emails to [email protected] to notify everyone of done work, that could include a short demo. We had a weekly all-hands video meetup. And each team had their own weekly meetup. Financials were available for anyone to see in a Grafana dashboard: our ARR, runway, expenses. Everyone knew about new deals.

TJ Holowaychuk shipped a lot every day. Quality work that was modular, packaged as a library, and then built on into an API or CLI. He wrote documentation. He was open to questions and talking things over. This was at the height of his celebrity but he was a hard working, no ego kinda guy. I was always impressed by him, one of the best coworkers I've had. Ian was another. Creative, always tinkering and making interesting projects. He had the idea for Segment's pivot. If there were squabbles he'd get everyone to take a breath and move forward. He was usually driving anything fun. These two made Segment what it was.

The shift from 30 to 100 people at Segment was sharp. I learned later that a VP smacked an underling in the face during a meeting around this time. The VP wasn't disciplined from what I understand and the other guy left the company. Ian left. TJ left. They were burnt out and have semi-retired. The work style had changed with more synchronous communication, Slack instead of email. We stopped hiring from open-source and started hiring people chasing hot startups with big series A rounds. We hired one of the worst teammates I've worked with. The hacker tribe phase of Segment was over. I lasted a couple of months before I was out.

I wished the company had stayed under 30 longer and that I'd joined earlier. More time with everyone, and more foundation to build. I left feeling unburdened, hungry. I felt like I didn't make my mark on enough at Segment. I picked Confluent as my next gig, to build Confluent Cloud from nothing. I wanted to build it all and I built more of Confluent Cloud than anyone. Five years later, Confluent IPO'd.

On the morning of October 10, 2020, Twilio announced they were buying Segment. That afternoon, Segment's stock team sent stockholders an email with a FAQ document on how stock would be handled: accredited investors would receive Twilio, unaccredited investors would receive cash. For accredited investors, the Twilio stock wasn't immediately tradable due to a lock-up period (50% sellable after SEC registration, remaining 50% after 30 days.)

The next day the stock team sent an email saying they'd host an info session over Zoom the following day. The Zoom call was full of people who'd worked at Segment over the years and ran long with questions, so they held a follow-up session that week. Twilio closed the acquisition on November 2, 2020. Later that week, Twilio's stock team gave me access to the stock transfer agent to manage my Twilio shares.

I made more that day than I would've made in over 20 years working at 37signals and I had more fun.