Digital health mafia departures

Making sense of company identity and individual careers

Last week, Halle Tecco posted a great write up - this time about healthtech startup acquisitions. I was lucky to be included along with TJ Parker (PillPack), Surbhi Sarna (nVision Medical), and Gil Addo (RubiconMD), who all shared great advice for how to approach a sale, and how to increase the probability of a successful deal. Have a look, and, while you’re on Halle’s site be sure to check out her long line of useful posts.

Two things I’ve been enjoying this month:

Drumha.us - A classic drum machine in a web browser, with a friendly interface and fun collection of sample kits and instruments. Compact, open-source, and free to use for anyone interested in music production.

The Peregrine by JA Baker - Recommended by Werner Herzog, who lists it as required reading for his film students, citing its “intense, visionary observation.” Structured as a diary, I’m reading the entries day-by-day and reminded to observe the water birds and raptors around my own place more closely.

Ok, on to a quick post about departures when starting →

Digital health mafia departures

Vive Collective recently published a list of digital health mafias - the companies whose employees in turn founded the most new startups. Propeller tops the list (on a per employee basis) with five, though my memory of the number of people who left to start their own thing is twice that at least.

I’m proud of that record and those people, and one day soon it would be fun to check in with them and write about their companies and what they’re up to today. But thinking about them today also reminded me how challenging it was when people chose to leave the company, particularly early on. 

Startups are bands. As a founder, few moments are more meaningful than having exceptional people find enough inspiration in your emerging vision to sign up. It confirms and energizes your ambition, and those people define and frame vital parts of the company. Amidst that, it’s easy to convince yourself you’re assembling a permanent lineup, whose familiar faces will be there in ten years when you cross the finish line together. 

But when people start to peel off for new projects, doubts and confusion arise. We don’t talk much about how to make sense of that experience as a founder.

At Propeller, I often found it perplexing. I tried to cheer them on without celebrating so much that others got ideas. But privately I worried about who was going to do what they did, or if anyone could. I asked myself what it meant to lose that person. Was the appeal of the company diminishing? Had they foreseen some problem on the horizon? At times, I was even slightly envious they got a fresh start to tackle a new set of problems.

One trick for me was realizing that, just like many bands, startups don’t have a permanent cast. Instead, they’re a classic example of a Ship of Theseus, the thought experiment that poses the paradox: If every piece of a ship is gradually replaced does it still remain the same object? 

Building a startup is a similar puzzle. It continually challenges you to juxtapose the identity of the company with the transience of its constituent parts. Initially, the team is the company, but these things separate with time. After all, there are natural tours of duty - as Reid Hoffman, Ben Casnocha and Chris Yeh describe in their book, The Alliance. According to their experience, the majority of people join startups for two-to-three year stints that modestly transform their careers (and the company). Consider and understand these dynamics, they argue, and you can co-create successful and productive missions at the company.

As a founder, it feels weird to balance the continuity of a company identity with the reality of employees’ dynamic careers. But if you can appreciate that organic renewal is its natural state, you realize how it’s invigorated by evolution. The whole thing will go through periods and variations in styles, just like a band. 

If you’re lucky, you get to see all kinds of versions of your company, unique embodiments made up by the different mixes of people. And later, when your own foundational tour has come to an end, how rewarding it is to see the long arcs of people who joined and left to lead their own adventures, and watch their energy echo through a new generation of companies.