In the current capital-rich environment where anything seems possible, I’ve been slipping into a habit of wondering how previous companies would have worked out had we started them today. After much rumination I think my biggest missed opportunity was not a constraint of capital, but rather an undervaluation, and misunderstanding, of sleep.
Like many, I was given a rude awakening by Matt Walker’s (excellent) book a couple of years back. But it’s still pretty alarming the number of people I meet who give me blank looks when I enquire about their sleep habits. Listing my biggest sleep mistakes to help other founders and leaders:
1. I’ll sleep when I’m dead exited
My single biggest error was having a completely incorrect mental model for sleep, treating it as a requirement, not an enabler. First I thought of it as dead time that needed to be minimised. Then I began to think of it as a fixed cost for being awake. Both of these are wrong (scientifically). I still occasionally meet people who are trying polyphasic schedules to minimise sleep-time, there is now sufficient peer-reviewed data showing this is a very dumb idea. The best (both scientifically accurate and which clicked for me) mental model is to think of sleep (not food) as your brain fuel.
2. Red-eye flights and misplaced financial prudence
Pre-Covid, I flew a lot (~250k miles/year) which inevitably meant frequent red-eyes. In my first couple of companies, I used to fly economy for literally everything. Gradually I realised the false economy of that principle: if I’m flying into a day of meetings, my level of sleep is going to determine the quality of discussion and decision-making. I started thinking of myself as a vessel for sleep and (selectively) began flying business.
3. Not taking sleep as a fiduciary responsibility
Only in the last 2-3 years did I truly grok that sleeping properly was part of my responsibility as CEO (also true for any member of a leadership team). An investor backs a founder/management team for their competence in strategy and decision-making. That categorically requires good sleep habits: REM is really important for cognitive functionality and mental resilience. I’m still amazed that many investors suggest executive coaches but not sleep reviews.
4. Misunderstanding THE EFFECTS OF COFFEE
I am unquestionably a coffee snob. For years I lauded my own ability to ‘not be affected by caffeine’, which meant that every dinner ended with an espresso (permanently jetlagged road-warriors will empathise). It turns out this was also pretty dumb. Caffeine has a half-life of about eight hours, so although I never had an issue getting to sleep it was actually reducing my deep sleep cycles by ~30%. Do this for long enough and it will shorten your lifespan by 8-10yrs.
Like any convert, I’ve become pretty zealous about the importance of sleep for decision-makers. It’s a question I now ask of all CEOs and investors. If you want to dive in a bit more, I recommend Andrew Huberman’s podcast which has several episodes on the topic. Also, it was very cool to see the recent launch of Supermoon Capital, a fund focusing on sleep-related opportunities.
Half-formed thoughts and musings 