Startup lessons learned running 200 miles

The best lessons tend to be those taught the most painfully.

Last Tuesday, June 18 at 3:35 am ET, I took my final steps of a 200.2 mile race called, appropriately enough, Tahoe 200.

Before and after “mugshot” or how to age 5 years in a little under 4 days.

It was the longest ultramarathon (or ultra) I had attempted (and thankfully completed) to date and the stats are pretty cool:

• Total time taken: 87 hrs and 26 min
• Total cumulative elevation gained: 36,857 ft (my first-time “Everesting” or exceeding the elevation of Mt. Everest in a single activity)
• Total sleep taken: 3 hrs and 8 min
• Total calories burned: 25,342
• Total blisters earned: Too many to count

With some 84 hours awake and only about 3 hrs of audio listened to on the trails, I had a lot of time in my head. Part of that time was reflecting on how much the lessons I’ve learned training and running ultras have helped me in the similarly challenging and ultimately longer act of starting and building a startup: Spark.

There are quite a few lessons but here are the top 3:

Lesson 1: Break up a big goal into smaller milestones.

In this case, the goal wasn’t actually the mountain but who doesn’t like a good visual metaphor?

You cannot run 200 miles and count each mile along the way. You will inevitably go mad, not slowly as the miles take longer later in the race, but early and quickly as the full weight of what remains crushes you from the very outset.

My strategy was to live aid station by aid station, meaning my only focus was getting to the next checkpoint, typically 15–19 miles away. It’s a distance that I’ve traveled comfortably many times before and also gives you an opportunity to give yourself a small reward: a favorite snack or a needed sleep break.

Starting a company is hard. You need to define a north star before you’ve even done or built anything of substance. That north star needs to be ambitious and well articulated such that you can convince others (investors, early employees) to join you in your journey. And the better you are at articulating that north star, the farther and more ambiguous the path to get there will be and the easier it is to be crushed into inaction by the weight of your own ambition.

But inertia is a powerful force so the best thing to do is to get started and the best way to get started is to focus on a smaller milestone. Choose something knowable that you’ve done many times before, be it doing user research or scoping out key problems or developing a financial model or even just completing a brainstorm session. Once done, reflect on what you learned and choose a new milestone based on those insights then rinse and repeat.

Lesson 2: To rest is to reset.

There is no worse feeling than deciding to drop out of a race and to realize 10 minutes later that you’re ready again to keep going.

Rest can come in many different forms and doesn’t need to be the same for everyone. For some, it’s walking up a hill instead of running to give your legs the chance to use slightly different muscles. For me, I found particular joy in surveying the various boulders and fallen tree trunks along the trail and finding the perfect spot to rest for 15–30 seconds at a time (couldn’t be too slanted, too far, too high or too short). Afterwards, I was able to go much faster and for much longer than if I simply tried to push through the tiredness.

You can also use rest to extend your Duolingo streak.

To be clear, this is a hard lesson to internalize. To rest will typically involve a lack of progression and what are startups if not built on the exponential momentum of compounding progress.

Here is where a meta lesson is necessary: quickly disassociate your identity from the startup. As a key leader, you’ll have an outsized impact on the success or failure of the company but you must also very quickly build a system that can withstand your absence. Not just for your own sanity but for everyone else’s as well. And it’s those sporadic absences where you can truly rest and reset for the next milestone facing you and the team.

Lesson 3: Challenge assumptions.

Five years ago I would have said the idea of me running 100 miles is impossible. The ability to hold a new perspective where that distance is now half of what I’ve been able to accomplish is eye opening, not just for what I can run but by making it easier to question the many other assumptions I hold in life.

Warning: Challenging assumptions may result in equal doses of euphoria and pain.

Assumptions are easy to conflate with facts, especially the longer they are held. Challenging them then feels less like discovering the unknown but rather the pursuit of certain failure.

But it’s important to remember that failure is transactional, not a state of being. In fact, it’s a transaction of effort for data that you can then use to chart your next milestone in a more educated manner.

The very act of doing a startup is an exercise in repeated failure. Which also means it’s an exercise in constant reinvention. Your initial thesis is an inherent challenge to some widely held assumption. As you grow exponentially, you will need to constantly challenge yourself, your team, your processes on what worked before because they will break quickly and violently. Many of your ideas or solutions will fail but a few will not. The only way to get to a path forward is to start with questions.

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I’ll end by saying that this isn’t an attempt to convince others to run ultras — I will be the first to admit the toll it takes on your body. Regardless, it’s helpful to find a companion activity that lets you reinforce the lessons above through more cycles. So for anyone looking to do something that feels monumental, find your version of ultrarunning and most importantly, just get started!

Final bonus lesson: it always helps to have a great “crew” to support you!