The toughest part of growing Segment from $0-200M+ ARR was letting go of product (which I understood) to focus on go-to-market (which I didn't). In 2017 I was really struggling with this. Five friends set me straight, a thread. 1/12
.@calvinfo @ivolo and I dropped out of MIT undergrad straight into Segment... and 6 years in we were now responsible for a growth stage startup with several hundred ppl. 2/12
I had no intuition for go-to-market strategy, systems, operations, recruiting... because I'd never seen it. I had never worked at another company! 3/12
At this point I remember thinking "Yeesh, it would be really useful to see inside another company or two right now." But I was too junior to get recruited to a board. What to do? 4/12
Eventually my coach @timporthouse had an awesome idea. 5/12
I should find some tech founders at a similar stage and do a peer board meeting: four of them in a single day, back to back, share all our board materials, financials and problems, and help each other. 6/12
Thanks to @rowghani at Y Combinator Growth, I'd met three of the world's finest French founders: @danielyanisse at Checkr, @collinmathilde at Front, and @dessaigne at Algolia. They all agreed to try this wild idea. 7/12
The peer board sessions were incredibly helpful, can't recommend enough. 8/12
One example: Segment had a developer-influenced enterprise software sale w/murky verticals. Algolia was more developer-led. But Checkr and Front were totally different: strong verticals and a very different sales motion. It was like I could see in color for the first time. 9/12
It was also an emotional support. 10/12
Like any human you get attached and loyal to your team. But sometimes it's not working out. I remember every one of us knew in heart of hearts we had to part ways with someone on our team... but we all needed the advice of the others to see it clearly and act. 11/12
Now in the midst COVID isolation it seems more important than ever to find peers to bond with, commiserate with, and learn from. Sorta awkward at first, but ultimately incredibly helpful. Thank you Ali, Tim, Nicolas, Mathilde and Daniel! 12/12

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More from @reinpk

7 Jan
After nearly 11 years leading @Segment from its infancy to the world’s leading Customer Data Platform, today is my last day at Twilio Segment. Starting Monday I will be working full-time on @CharmIndustrial, focused on permanent carbon removal via bio-oil sequestration. /1
Segment’s first two failed ideas were mine, so I’m incredibly grateful to have had my best friends @ivolo, @calvinfo and @ianstormtaylor as co-founders. Their idea to make open source analytics.js into a product sounded insane to me, but they couldn’t have been more right. /2
From that brutal analytics.js argument I lost in December 2012 to Segment’s $3.2B acquisition by Twilio and to incredible growth this past year accelerating to hundreds of millions in revenue, I’m incredibly grateful I had the opportunity to work with amazing sharp leaders /3
Read 16 tweets
2 May 19
1/ Today is 8 years since we founded @Segment! Like many startups, our first two years were brutal. The last six have been an insane ride. We made so many mistakes along the way, and owe so much to our early customers.
2/ While attending MIT and Y Combinator in Summer 2011 we built a classroom lecture tool called ClassMetric. YC constantly told us to solve real problems for our customers, but we somehow ignored this and 80% of the students just opened up Facebook instead of using our tool.
3/ Next we built a web analytics tool to compete with @Mixpanel and @googleanalytics, but they were already great tools... we had somehow managed to ignore YC's advice again. Real customers didn't have an issue with analytics.
Read 16 tweets

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