Watching Novak Djokovic play tennis is a pure delight, but I love listening to him talk about tennis even more. He's the GOAT - a perfectly tuned machine with a deeply intrinsic sophistication when it comes to the game. I always look forward to watching his post-game commentary. He has become an exemplar of sportsmanship, remarkably gracious when he wins and loses.
Earlier this week he played an incredible match against Jannik Sinner where he lost in three sets. You can watch the highlights here (they're incredible). What stood out to me more was Djoker's analysis of the game. Listen to how he talks about it, remembering every critical point and juncture throughout the match, reciting specifically what happened and when.
My favorite part is how he attributes Sinner's win to the fact that he was "more decisive and courageous in the moments he needed to be." He also notes, "In these types of matches very few opportunities are presented and if you don't use them the other player will."
So much about these comments remind me of company building. When I talk to entrepreneurs and look back on my own journey, so much of the story and outcome is usually attributed to having the courage to be decisive in the most important moments, which are almost always filled with ambiguity at best and more often absolute existential chaos. It's incredibly frightening to step up in those moments - it's much easier to let them pass you by. But having the courage to make decisions during these defining times, whether they are right or wrong, is oftentimes the thing that makes or breaks a company. It's one of the most important hallmarks of entrepreneurship.
Over the past year I've had several bouts of sleep anxiety. When I lay down to try to get to bed I get so anxious about not being able to fall asleep that I end up spiraling in my head and the anxiety compounds and grows out of control. I can get very uncomfortable in situations I can't control, like when my kids are sick, and this feeling of helplessness is particularly difficult and sometimes scary for me. I’m a pretty cerebral person so my instinct is to use my thoughts to manage my feelings and sometimes that can backfire.
When I was building companies I'd frequently wake up in the middle of the night and obsess about a conversation I needed to have with a team member or a lingering issue I needed to address (like firing someone or providing tough feedback), or I'd just stew about a competitor’s feature release. The issues would range from trivial to existential. I'm somewhat used to the struggle to get back to bed and fortunately don’t grapple with it frequently, but having trouble falling asleep in the first place is a new and intimidating thing for me.
It started in March when I had to wake up at 4am one day for an international flight. Ironically, it was the night I finished reading Why We Sleep which probably put some artificial pressure on me. I was recovering from a cold and so concerned about making sure that I fell asleep so I'd be rested for my trip that I couldn't sleep at all. It was the first time I felt anxiety physically manifest in my body as an incessant tingling in my arms. Since then I’ve had a couple more instances of this, mostly catalyzed by a feeling of helplessness about an event in my life.
While I’m extremely grateful this is a rare occurrence, I of course am concerned that it will happen with more frequency in the future. Sleep anxiety is really uncomfortable, and I have a great deal of empathy for people who struggle with sleep related issues. Perhaps an overreaction, I’ve started to research (ie completely fallen down the rabbit hole) CBT techniques to help. I’ve also cycled through various sleep products from the Eight Sleep mattress which we returned (I may try the ChiliPad since it seems less tactile and has a half-bed option), an Oura ring, and other smart sleep devices. I’ve found that the more things I buy for sleep and the more I focus on it, the more I feel pressure to perform. Oftentimes the obsession with the act has a counterproductive impact.
I’m going to play with a couple apps like Stellar Sleep and Sleep Reset to better understand how CBT is used for managing sleep anxiety. It makes me really happy that entrepreneurs have worked to help people with digital tools and education in this space. I'm somewhat surprised I haven't stumbled on a dedicated network for people to connect and share their sleep experiences and tips outside of Reddit.
Getting older is a weird thing. The problems I heard about when I was young and seemed like made-up adult issues gradually creep their way into life. I’m so appreciative that I made it 36 years without experiencing sleep anxiety, and I’m optimistic that tackling the issue will be a rewarding adventure. More than anything, I’m going to do my best to accept that sometimes things are very much out of my control and my world won’t collapse if I struggle to get to bed (or back to bed) on occasion. If anyone has any tips or recommended resources, please do send them my way.
Conventions around vesting for founders and early employees who receive big chunks of equity (eg more than ~5% of fully diluted shares outstanding) need to be updated. Founders are normally subject to traditional vesting cycles: monthly over four years with a one-year cliff. There are many reasons why founders like this, namely that they have a predictable time frame to fully vest which seems reasonable when starting a company. But there's a strong argument that this isn't in their best interest, especially when they have co-founders.
Too many times I have seen founders who have slogged through nearly a decade of company building resent the fact that a big piece of their cap table sits with co-founders who departed the company before things really started working. They are sad that they bailed when things got tough, or that they simply lost interest immediately after fully vesting and moved on to the next thing. And they're particularly frustrated that they and their leadership team own less of the company they worked so hard to build because they chose to spread their equity across people who wouldn't participate in the full ride. This happens more often than not - it’s the rule, not the exception.
To hedge against this predictable outcome, more founders should adopt longer vesting cycles for themselves and the earliest (big equity) employees. Stretching things out to a six-year vest helps to prevent co-founder abandonment. Equally important, it also protects you if your co-founders aren't the right fit early on - you don't want someone leaving two years into building your company with the lion's share of the cap table. That sucks for everyone. Another construct I like is a four-year cycle where vesting is backloaded (e.g. 10% after year 1, 20% after year 2, 30% after year 3, and 40% after year 4). Longer vesting cycles also align founders with investors who are committing to the company and team. I recently learned of a firm asking founders to stretch out their vesting schedule for their unvested shares when leading a round. I like this, and while some founders may view this as unnecessary, it is a good thing. Incentive alignment is powerful.
Some people may argue that by starting or joining something very early stage they are assuming a lot of risk and therefore should receive a lot of the upside. The fact of the matter is that it usually takes many years for something to click, and by the time they normally do the teams that are in place can look quite different. Do people who were there early when things weren't working and subsequently left deserve meaningfully more than those who buckled down and willed the thing to product-market fit and scale? I don't think so. People should be rewarded for making something work, and that usually means being there for when it works. Being granted a meaningful amount of equity is not an entitlement, it is something that should be continuously earned over time. Stretching out the vesting schedule helps to level the playing field for the people there today, and for those to come in the future.
