“And I’mma step-up again and slam, grand-slam…”

– Cam’ron – You Gotta Love It


2018 is a special year for me: I will enter my third decade of being a venture capitalist working with some of the world’s best entrepreneurs; I also plan to complete the Grand Slam of Ultrarunning, a set of four 100-mile trail races held over a three-month period, for the third year in a row. This effort will mean running an aggregate of approximately 100 hours (hopefully less!) through rain, snow, high altitude and the dark of night.

Naturally, these two milestones have me thinking about the commonalities between ultrarunning and building startups, as I had done before for TEDx Beacon Street around the idea of “hacking” an ultramarathon (with others on the virtues of fasting, and silence). On the surface, there’s not much in common: one involves physical exertion over the span of a day or two and a clear finish line, the other mental and intellectual exertion over the course of years, with ever-changing goals.

An ultramarathon is, by definition, any foot race longer than a marathon (26.2 miles), with most running between 50 kilometers and 100 miles. These are deeply grueling races where competitors run across varied, difficult terrain requiring incredible physical strength and perseverance.

On the flip side (and decidedly non-physical, aside from the occasional bout of sleep deprivation), building a startup is creating and executing on an idea. But defining success as a startup founder isn’t straightforward, and there’s no set outcome or length of time for building a successful company. Though there may not be a clear endpoint, entrepreneurship also requires an incredible amount of dedication, persistence and mental strength.

Now let’s look at the odds of success for each activity: 50% of runners aged 30-39 (the largest age bracket) never cross the finish line at the Leadville 100 (one of the Grand Slam Ultra Marathon races). Meanwhile, only 50% of new businesses survive longer than 5 years. That’s half of all people across both activities that fail — and these are folks who have self-selected themselves to take on a challenge. The Western States 100 is the “Super Bowl” of ultrarunning and during one attempt I could not finish due to complete exhaustion, and was taken to the medical tent and rehydrated with two liters of IV fluid. But, just like a repeat founder, I learned some impactful lessons from the race, and applied them with success the next time I was out there.

Both activities take deep dedication in the face of failure. And both endeavors are filled with dramatic highs and lows, with opportunities for incredible success and fulfillment, but also devastating physical and mental challenges and heartbreak. Below are some other similarities I’ve picked up from the unique position of being Managing Director at Ridge Ventures, as well as an ultrarunner with over 50 ultramarathons under by belt.

Get prepared


Running an ultramarathon isn’t for the faint of heart. To complete a race that long and grueling, you must prepare mentally and physically. From long training sessions to qualifying races, the process for an ultramarathon can take weeks, months, or even years. While it’s easy to focus on the end goal of completing an arduous race, getting there would be nearly impossible without proper preparation and building a strong base. To get my legs in shape for an ultra, I often run 8-10 hours per week, including a training marathon each weekend. The preparation even trickles down into the smallest of details, like figuring out the right mix of salt and electrolyte supplements to use during the race by experimenting on training runs, or having a plan for taking care of your battered feet mid-race.

The same can be said for building a startup. Anyone who has ever watched an episode of Shark Tank knows that a VC worth their salt won’t take a startup crew seriously who hasn’t done their homework. Preparing to build a startup involves many things: everything from detailed research of the industry, to knowing what problem your startup will solve, to understanding how to launch the product and market it, gaining early user feedback, and potential pivot options. As Benjamin Franklin wisely once said, “If you fail to plan, you are planning to fail!” Preparation can’t be emphasized enough as a crucial component of startup success.

It’s all about willpower


Another parallel between building a startup and running an ultramarathon is the mental fortitude required for both endeavors. The long term nature of both ultramarathons and building startups requires huge amounts of mental strength. Running for such long distances allows for long, uninterrupted time alone with your thoughts. In order to control and maintain your physical output, your mind has to be clear, committed, and focused on the task at hand.

The same kind of mental fortitude can be applied to building startups. You won’t have all the answers from the get-go and remaining patient and mentally strong as you tackle any challenges (and there will be challenges). Just like each mile brings an ultrarunner that much closer to the finish line, each day in startup life brings you closer to success.

There is no skipping steps (or miles). If I have a 12-hour work day and get home after dinner, I will strap on a headlamp and go for a run, rain or shine. My running quota of 70 miles per week is non-negotiable and if I miss a day, I have to run double another day that week. You must pace yourself, tackle each challenge head-on, and prepare for the next obstacle, all with the mindset that eventually your goals will be achieved.

Obstacles are part of the journey  


During an ultramarathon, you should expect for at least one unexpected obstacle to pop up. Whether crippling fatigue, an agonizing blister, a serious injury, or even a moment of mental weakness — these obstacles can challenge even the toughest of competitors. The best way to increase the chances of overcoming these challenges is to prepare for them. Know they’re coming. Work them into your race plan.

The same can be said for a startup. Unexpected challenges are simply part and parcel of the entrepreneur’s life. That’s what pivots are made for. Before taking the world by storm with their Candy Crush app, gaming company King had 30 games that flopped. 30! They failed again and again, yet they still pushed on, eventually finding incredible (and well deserved) success.

Another example of a company overcoming challenges and embracing change is Pandora. These days, Pandora is synonymous with internet radio, but the company originally began as a music kiosk service for record stores. Getting to where they are today wasn’t easy, and required pivot after pivot, with many near death experiences — and I know this because I was one of their very first investors.

Embrace the crazy


Announcing to others that you’re running an ultramarathon is often met with disbelief. At some point the word “crazy” will likely be uttered. Why would you want to RUN a hundred miles??

Embracing that label and running with it (so to speak) is a necessary component of being an ultrarunner.

Yes, you have to be a little bit nuts to embark on such a grueling endeavor, but that’s exactly why you’re the one running it in the first place. Proving to others and yourself that you CAN and WILL finish arguably the most difficult physical achievement of your life will help test your limits and take charge of your life.

This same analogy goes for building a startup. Leaving a cushy job, spending your life savings, diving into the unknown to maybe find success as an entrepreneur? It’s crazy to say the least. But you’ll never know until you try. What all entrepreneurs have in common is that spark of intuition to venture out on their own. And though they may fail, they’re fearless in their “crazy” quest of achieving their entrepreneurial dreams.

There are no highs without lows

giphy1Ultrarunning and being an entrepreneur can be both painful and incredibly rewarding. They can make for lonely experiences, but also allow for moments of incredible camaraderie and teamwork. A great support team on the trail and in business are integral elements of both endeavors.

The bottom line is that there are no highs without lows. Earning those highs — whether they be crossing the finish line of a 100-mile race or incorporating your own company — requires grit, discipline and commitment. Expecting the unexpected, building out multiple alternative plans, and crafting a mindset around solving challenges, are the keys to success in both realms. The results of the Western States 100 lottery come out seven months before the race – and you think about that race every day up until it starts. The dedication, hard work, and journey to the start line is half the prize in itself, and the feeling of catharsis when that starting gun goes off is incredible. All the preparation I’ve done to get to this point has paid off.

And what kind of startup-focused list would this be if we didn’t at least mention competition? Ultra running is not just about finishing the distance. It’s about combining speed and distance to get to the front of the pack. I will never forget being at an aid station with three other runners at mile 55 of the Miwok 100K. It was the 9th hour of running, and we had to run out of Tennessee Valley up Wolf Ridge (the steepest hill in the Marin Headlands), and then bound straight downhill to the finish line. I looked at the three other guys and said to myself, “this is my backyard, there is NO WAY they are going to beat me.” That sense of competition and pride allowed me to hold them off and finished in 6th place overall. Many of the entrepreneurs I work with have the attitude of “total global domination.” Their desire to win is infectious, which is a necessity in helping their team succeed.

In the end, embracing the physical pain of an ultramarathon and the grinding and exhausting nature of building a startup can lead to the most satisfying moments of your life and career. You won’t regret taking on the challenge.