So much can go wrong between the 25 to 100-employee ramp that I consider it make-or-break for a promising startup. Sure, if the market pull is strong enough, you'll "succeed" whether you were intentional about it or not, but man—just the amount of unnecessary suffering when it's done poorly!
I didn't expect this of myself, but it turns out that I am a Series B animal. In fact, I've come to realize that I'm better as an advisor than an operator in the early stages. But when the systems get more complex, sniffing out where the leverage is and managing the change through a growing organization plays perfectly to my strengths. So 25 to Dunbar's number is when I'm most in the zone.
I've been an IC (individual contributor) in a painful ramp and I've been a newbie executive in another—both tremendously valuable experiences. However, this time, on the third go-round, the game feels much slower to me and I'm actually having fun and able to exercise a lot of spontaneous creativity as a result. I'd love to trade notes!
I came across Kneesovertoesguy on YouTube in mid-2021 and it has been a revelation. I've always taken pride in my barefoot/minimalist adapted feet (a lifestyle change I made in 2010), but the mobility standards from ATG training really blew my mind.
Fortunately, when I tested myself, none of the standards were out of reach, but I was still far from being able to claim a clean bill of health by those standards.
I've therefore set out to meet the standard as soon as possible and maintain it for at least a couple of years to see what kinds of benefits I'd experience in practice. For instance, just doing split squats on the regular has already made my lower body feel more resilient. It's been more powerful than yoga for flexibility in many ways (although I'm sure my background in yoga is helping me achieve the standards much faster than I otherwise would be).
I've recently been talking to engineering leaders at startups that are in an earlier stage than CollegeVine and have found great joy in helping them transform their engineering teams by teaching important concepts and principles that I've learned over the years.
I didn't realize it at the time, but the intuition for why I've captured and distilled the right framework and principles is that CollegeVine essentially allowed me to do the closest thing possible to a controlled experiment on culture: we built the business one way through 2019, decided we didn't like that business model, pivoted and downsized, I did a bunch of thinking about engineering's role in all that, and did it all over again with another business model and culture with the same core group of people.
So the people didn't change, but the results were drastically different this time around. That's probably as close to an A/B test on culture as you'll get in this line of work.
But don't take it from me. Here's what a grateful advisee had to say:
"Just wanted to say thanks again for all the advice man. We've talked to many CTOs at various stages but you are the one who [our lead engineer] and [engineering manager] consistently want to hear more from." — a founder/CTO
Due to these positive experiences, I've vowed to always take a call from any budding engineering leader who wants help. Think of it as my way to pay it forward for all the good mentorship I've gotten over the years.