Ride It to the Sky

One of the worst feelings in the world is having a sick child. Nothing eats at your heart and soul more than the feeling of helplessness that is watching your kid feel ill. Like all parents, I’ve had plenty of harrowing experiences with my children ranging from hospital stays with viral meningitis to a one year old turning into a blue balloon with serum sickness. Nothing makes me more sad and anxious than seeing one of my kid come down with a bug.

Another unfortunate thing about kids being sick is having to physically go to a doctor’s office for just about everything. Some pediatricians do some form of telemedicine, many through Klara in my experience, but they’ll seldom diagnose or prescribe anything without seeing the child in person. At first I thought it was understandable, but so many of these diagnoses are rather rote and can be done with a photo or video. The other downside of having to physically go into your pediatrician is that you can never see them when you want, which is always as close to Now as possible. The options are normally wait a couple days or make your way to urgent care. More often than not what a parent wants is to simply know that things are fine and that tylenol/ibuprofen are good for now.

Last year I learned of a service called Summer Health that enables you to text with a pediatrician 24/7. The communication is pretty much synchronous and I love it because it nearly instantly provides me peace of mind. Every time I text Summer I’m sent a link where I can view the credentials of the pediatrician I am speaking with, and I enter a real-time SMS conversation with them within minutes. I’ve talked to them at all hours of the day about things ranging from head bumps, questions about strep throat, how to remove excess silver nitrate on one of my kid’s faces from a procedure at an ENT, whether you can administer antibiotics if they’re expired but have lived in the refrigerator, what medications are okay to take with norovirus, how to know if your child is a carrier for strep, and many more things from the mundane to quite serious. They also call in prescriptions and frequently ask for photos or video to better understand a condition. All of my interactions have been pleasant. And while the doctors don’t always nail the condition (eg maybe they think something is croup instead of another respiratory issue), I get an educated opinion quickly and know whether I can wait a day to take my kid in or if I should get a move on things. The service is roughly $20 per month which is an easy price for me to stomach paying for the peace of mind I get from it.

I’m really interested in this space for a whole host of reasons. First and foremost it’s a personal problem I have – I’m a parent of two children and they sometimes get sick. I also appreciate that I can instantly communicate with a real pediatrician over text. It’s like being able to text a family member that practices medicine – it’s an invaluable resource. The channel of communication makes it special along with the fact that it’s a real human being.

There are two things about its future that intrigue me most. The first is whether I’d be okay chatting with an AI. One of the things I’ve been doing recently is cross-referencing things I’m learning or recommendations from doctors with ChatGPT and I’ve found that ChatGPT nails most every question succinctly. I’ll sometimes start a medical search on google and end up on a research paper and find my answer (eg how would you calculate the dosage of this specific drug?), then I’ll go to ChatGPT and get a nearly identical answer. The results are pretty astounding, so for me I do think I’d be perfectly fine communicating with some chat-based AI, especially if I know there is a human in the loop somewhere and I can ripcord to them. The second thing I’d like to see happen is a suite of remote diagnostic tools more broadly utilized and made available to every household. One of the reasons why pediatricians want you to come into the office is because they physically want to see your child so they can evaluate them with a stethoscope and otoscope. There’s enough hardware out there now that should enable remote visualization of ears and throat and listening to breathing. It’d be a lot easier to stream or send a video of an ear canal, see an ear infection, and have antibiotics delivered to your door within hours than waiting 24 hours to see your pediatrician or in a waiting room for hours at urgent care. It’s obvious that this is where the future of care will end up, it’s just a matter of time (and not just for pediatrics but for all care). It’s also important that this trend will make healthcare meaningfully more accessible to people all around the globe, even in the most remote parts of the world.

I’m very excited by these trends. It’s incredible that something as simple as on-demand text based communications can change healthcare access and the healthcare experience. It’s a great building block and entryway to a much broader world of healthcare, and I hope it advances quickly because it’s going to help a lot of people and provide them much needed peace of mind when they need it most.

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.

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.

This may seem like a preposterous concept. Why should it be on the employee to help a founder recognize their talent? Shouldn’t good founders always know who is good and deserves to take on more responsibility? The sooner people realize that founders are massively flawed, are largely making things up as they go along, and have a real learning curve when it comes to how to nurture and manage talent, the better – you can use that to your advantage. If you can practice a delicate mix of patience, humility, honesty, and assertiveness, you can, as a young and talented contributor, truly thrive and shoulder more responsibility than most 20-somethings can fathom. This is an extremely difficult combination of traits to express, especially when you are early in your career, think/know you’re good, and likely have an ego. It requires a great deal of maturity.    

These are some things I wish I had known when I was starting my career at tumblr when it was very early stage, and things I wish I had known to communicate to high-potential people that were early in their respective careers. They may seem obvious, but they’re worth reiterating. The key is you want to understand how founders really feel and think in these types of situations.

• Don’t push for title. You do not need to be Chief-Anything-Officer in your early 20’s. Instead, push for responsibility. I don’t want to hear from a 20-something-year-old how they think they should be a “VP” or “Head of” or “C-something.” I will immediately go to an internal dialogue of “Screw this person, who do they think they are?” Even if you’re the messiah, most founders will think this. They want to come to this conclusion on their own. Don’t create a set of biases in the founder’s mind that you have a real sense of entitlement, even if you’re over-delivering. What I want to see is someone who is going above and beyond, delivering terrific outcomes, and yearning to do more. 
• Don’t imply that you are going to quit if you’re layered. Do people actually do this? All the time. Instead, produce outcomes that make you indispensable and carry yourself like you’re already in the role you want. I want approximately zero veiled threats from someone early in their career. There’s no better way to convince someone you’re not ready for a step up than to be passive-aggressive. Implying you’re going to leave if someone with 15 years more experience than you becomes your manager is just going to give a founder unnecessary anxiety. They’re going to question why you brought this up in the first place and whether they want to deal with the hassle. 
• Don’t constantly ask for things that don’t help you perform better in your role (like more salary, equity, title and reports), but do be honest about what your aspirations are and self-aware enough to know and articulate what you need to get there. I’ve seen high-potential high-performers ask for more money at virtually every review cycle (and in between!) who earnestly believed they were advocating for themselves. Maybe they were, but they were also being annoying. That was the last thing I wanted to constantly deal with. There is a tact to this process that requires real maturity. I am not suggesting to not advocate yourself, I am saying that you need to do it in a way that conveys you are an asset instead of a diva, a leader instead of someone who doesn’t know the ropes, and exhibit some semblance of an understanding of how these decisions are made amongst leaders and founders. 

These bullets may sound ridiculous or even condescending because you’re the Talent and you’ve gotta get what’s yours! And sometimes leaders do need a kick in the ass to recognize that they really are working with a superstar (I certainly needed several). But the ability to read the room and navigate it is a soft skill that will truly set you apart. In addition to being terrific at what you do, understanding weird founder psychology and being mature beyond your years can be the distinguishing factor in how much you learn, grow, and are compensated over the course of your journey at an early-stage growing startup. If you’re working with a decent founder you will notice that the people who managed to grow with the company from early on and ended up with the most responsibility and equity are almost always the ones who strategically asked for the least.