A new adventure

A new adventure

As they say... some personal news. After nearly a decade of building Segment, I'm leaving to start a new adventure. My last day was November 2nd.

We first signed the incorporation papers for Segment (then Classmetric) in May, 2011. I remember inking my name on top of this big wooden table in the kitchen of our college dorm. It was one of the first legal documents I’d signed outside of opening my bank account. My co-founders and I had just turned 21. We were starry-eyed at the prospect of participating in YC and excited to take on the world.

Never did I imagine that moment would be the start of a decade-long journey which would culminate in a $3.2B exit.

It’s hard to fully describe all of those moments in just a few sentences, but I’ve found the startup journey feels a bit like trekking up a mountain.

Some days, you’re delighted by the sights of wildflowers and hidden alpine lakes. Other days, every second is a grind as the wind and rain threaten to knock you off your feet. Day in and day out, you try and climb a little bit higher.

That journey has taught me countless lessons about product development, data pipelines, hiring, and of course, what it takes to build a company. I wouldn't trade the experience for anything (I’ll share those lessons in future posts).

I see the acquisition as an important trail marker in that journey. It's a milestone that everyone at Segment can point at and say: “Yeah, I helped build that."

With the acquisition, I’ve now reached my own crossroads on the trail. We accomplished what we originally set out to do all those years ago: build a great company.

Now, I’m ready to lift my gaze from the immediate path and widen my perspective. It’s time to look out at the horizon, and survey the other mountains worth climbing. Time to consider what new adventures the next decade might hold.

What I'm feeling

Before I share a little bit more about what's next, I wanted to take a snapshot of my thoughts over the last few weeks. My friend James (who sold his company in 2014) gave me a key piece of advice: take a moment to write down how you're feeling, because the next month will feel like a blur.

James couldn't have been more right. With the acquisition, the election, a global pandemic, and more-the events of the last two months have led me to do a lot of introspection. In no particular order, here's what I felt...

Pride — reading the comments on Twitter, Hacker News, and investor analysts, I couldn't help but swell with pride. I saw a lot of posts along the lines of "everyone at Segment is awesome" or "it's an incredible product". I kept expecting the trolling comments and hot takes, but they were noticeably absent.

Quite frankly, I couldn't believe how nice everyone was. This is the internet... that never happens!

In every sense of the word, we built a "good" business. We did right by customers, partners, our early employees and our current teammates.

Sadness — on Oct 30th, my co-founder Ilya and I said our last goodbyes to the company. In that moment, I felt a sudden wave of sadness. I fully realized I was parting with the teammates who I'd spent the better part of my 20's with. We'd grown up together, laughed together, struggled together, and in doing so, built something very special. I'm going to miss everyone over at Segment, and hope that we get the chance to work together once more.

Gratitude — Segment has been an incredible learning experience for me. I've had some of the world's best teachers when it comes to scaling a company, building infrastructure, finding product-market fit, and more. I'll try and write down as many of those lessons as I can over the next few months.

To our board: Vas, Miles, Ali, Kim, Rob, and Sue — thank you for teaching us how to grow and scale a company. You've consistently helped us step outside of our own heads and build a world-class enterprise business. You have my eternal gratitude.

To the countless teammates and leaders at Segment — thank you for teaching me everything from building infrastructure, GTM, hiring, finding product-market fit, and how to craft an amazing company. I've learned countless superpowers from each and every one of you.

To our customers — thank you for supporting us in the early days and pushing us to deliver a high caliber product. The fact that you cared about what we were building was the thing that kept us going. We really wouldn't be here without you.

To Tido — you deserve a special shoutout for taking on a founder-esque role when it came to scaling Segment. Thank you for getting us through a critical time in our history and building the world-class EPDS team we know today.

To Ian, Ilya, and Peter — thank you all for the good times, the hard times, and the countless laughs. I couldn't have asked for better friends to build a company with.

Deep satisfaction — There was one feeling that I didn't expect… this deep sense of contentment that continues to permeate every fiber of my being.

I've read about a concept in so many business books that it almost feels clichéd to say it, but the thing I'll remember most about Segment are the moments spent with all of my teammates.

The late nights polishing and testing before a big product launch. The hack weeks and off-sites that led to big new breakthroughs. The whiteboarding sessions spent planning our infrastructure. The packed rooms (and then zooms) with bigger and bigger customers. The 4am incidents to fix some part of our pipeline.

Those experiences are the ones I'll remember, but not for the reasons I thought I would. What made all of those experiences special were the people I shared them with, and all of the lives that were positively impacted by the company we created.

If I believed it before, I believe it more strongly than ever now: the most important aspect of any company are the people who work there. It's not the time spent writing code, well-researched product documents, or speaking at all-hands. It's the people.

What's next

Over the next six months, I’m embarking on a reading period to explore many different problem areas. I'm keeping an open mind, but plan to dive deeper into problems like tools for research, education, AI, data accessibility, housing, and climate change.

When we first started our Segment journey, I didn’t fully comprehended how long and soul-consuming the path to building an enduring business really is. This time around, I'd like to be more deliberate about the next effort to pursue.

As part of that next chapter, I plan to “work with the garage door up." Every few weeks, I'll be sharing my thoughts on what I've read, learned, and discovered.

If you'd like to follow along with my progress, I've set up a Substack with regular field notes: https://calvinfo.substack.com. Whatever lies in store, I'm excited to learn and build as the next chapter unfolds.

My only commitment outside of research will be helping various startups and companies I've invested in. The early investors we had at Segment consistently helped us avoid the pitfalls that can consume first-time founders. I'd like to repay the favor and do whatever I can to help the next generation of founders succeed as well.

To all of the family, friends, teammates, board members, and investors who supported us over the years: I want to say the most heartfelt thank you. We would not be here today without your encouragement, your thoughtful advice, and your helpful nudges.

See you all on the next climb.