Wolf of Williamsburg / The endeavors
Aaptiv
CTO and SVP Product and Content, New York / 2017–2021
At Aaptiv I was CTO and SVP Product and Content. I partnered with the CEO to raise $40M+ across Series B and C, scaled R&D from 5 to over 80 people, and grew the paying subscriber base from 5k to over 350k members, about $20M ARR.
We built the AI coaching and content exploration work, and a content team producing 50 new classes a week across 15+ categories. Aaptiv was acquired by Pear Sports.
From the archive
- The Long Way HereI build technology companies, work with startups, run and ride bikes, fix old houses, and start more side projects than I need.
- Averages Won't WorkA clean churn chart hid the real questions about who was exercising, who was renewing, and whether the product had become a habit.
- Mail Back the Bike KeyCOVID put me in the old Poughkeepsie house for real. A few days later Aaptiv asked for the bike-locker key and a decision about whatever was still on my desk.
- A Ridiculous MonthPart of the ceiling came down, the repairs became my job, and our temporary move to Poughkeepsie stopped feeling very temporary.
- Aaptiv, From HomeAaptiv's at-home fitness use jumped, and the company opened a new enterprise and API channel.
- The Gutters Fell InThe Poughkeepsie Victorian started leaking during lockdown while I finished references, left Aaptiv, and weighed a CPO offer from Equinox Media.
- Only One HundredA leadership search wanted someone who had managed 200 to 500 engineers. My org was only about 100, which was suddenly a small number.
- Finish Interviews. Learn Stickers.After arranging a possible Aaptiv transition, I planned to finish a few big-tech interviews and learn enough about Apply to decide whether stickers were next.
- Two Titles, Both Question MarksA working note reduced a new opportunity to two possible roles and a longer list of questions about people, economics, and the work itself.
- Tell Me the Truth, LinkedInAfter years of building startup teams, I started asking what a much larger technology company might offer and what I would have to give up.
- Not Allowed to QuitThe crew plan for my first Vermont 100 was simple: bring food, track the math, and do not let me make bad decisions.
- Two Forty-Five, PleaseI bought a marathon plan from Brad Hudson, marked it up, then brought the questions straight into Aaptiv.
23 more in the archive.