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.

Last week I met with an old colleague of mine who was one of the more talented people I've worked with in my career. They left Fundera as we were scaling (and went on to accomplish great things) because I was going to hire someone above them. We started working together when they were still in college and they did pretty much everything to help us get off the ground and reach product-market fit: operations, marketing, product, etc. They were a true high-potential generalist who was good at anything and everything they needed to do - likely better than even some of the best specialists in those functions. I think about them leaving as one of my biggest leadership mistakes and hardest lessons learned.

There is a lot of literature out there about how founders should always bet on their up-and-coming talent. It’s a common refrain, but we seem to regularly screw this up. We think it’s a safe move to hire the pedigreed external executive. Advisors and boards will push for it even if they don’t personally know the talent on your team. Everyone, not just founders, is predisposed to go after the “silver bullet” I’ve written about before. I think it’s important for founders to recognize this shortcoming - that our natural inclination is to wishfully believe someone out there can do magic for our company. But it's also advantageous to young and talented employees if they can recognize and expect this flaw in their founders, and I’ve been thinking about what a hungry, high-potential person can do to make it clear as day that a founder should be betting on them with more responsibility and not a trophy external hire.

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.

Last week I met with an old colleague of mine who was one of the more talented people I've worked with in my career. They left Fundera as we were scaling (and went on to accomplish great things) because I was going to hire someone above them. We started working together when they were still in college and they did pretty much everything to help us get off the ground and reach product-market fit: operations, marketing, product, etc. They were a true high-potential generalist who was good at anything and everything they needed to do - likely better than even some of the best specialists in those functions. I think about them leaving as one of my biggest leadership mistakes and hardest lessons learned.

There is a lot of literature out there about how founders should always bet on their up-and-coming talent. It’s a common refrain, but we seem to regularly screw this up. We think it’s a safe move to hire the pedigreed external executive. Advisors and boards will push for it even if they don’t personally know the talent on your team. Everyone, not just founders, is predisposed to go after the “silver bullet” I’ve written about before. I think it’s important for founders to recognize this shortcoming - that our natural inclination is to wishfully believe someone out there can do magic for our company. But it's also advantageous to young and talented employees if they can recognize and expect this flaw in their founders, and I’ve been thinking about what a hungry, high-potential person can do to make it clear as day that a founder should be betting on them with more responsibility and not a trophy external hire.