“0 to 100 real quick.”
Drake, 0 to 100 / The Catchup

What is wisdom anyway? Its definition is somewhat elusive. Many people talk about it, but by definition, wisdom is something that everybody hopes to attain. In general, a person’s goal is to exhibit wisdom in all facets of their life.

Last weekend I ran the Western States 100-mile run in just over 27 hours, non-stop. It was a grueling event as temperatures exceeded 100 degrees, altitude topped 8,300′ and at mile 80 I had to ford the frigid waters of American River. As I ran I drew upon all of my collective experiences to make various decisions, and I thought: “is this wisdom?”

The more I thought about this question, and I had a lot of time to think, the answer became clear. Not only was I making wise decisions, but I saw a direct parallel between the wisdom in long distance running and the wisdom I’ve gained as a venture capitalist and entrepreneur.

Here are 3 ways I applied wisdom to my 100 mile race and my life as a VC:


Knowing I’d be running for over 24 hours, it was critical to make sure I was going at a pace where I wouldn’t ‘blow up’ later. Throughout the day, I used my heart rate as a proxy to measure my pace. I focused on keeping my heart rate between 150 – 155 during the entire event. I further realized that I needed to slow my pace by appx. 1 minute per mile while running the portions of the race at 8,000′ altitude. While focusing on my heart rate, I thought about my TEDx talk on the 4 entrepreneurial hacks I employed a few years ago for completing the Wasatch 100 on no training: (i) having a good team, (ii) having a malleable plan, (iii) focus on the KPIs, and (iv) having fun. Drawing upon my experience in the Wasatch 100 and other races gave me the underpinnings to make wise decisions throughout the day – and night – and the next day!

Pacing is also a critical part of entrepreneurship. It’s not only making your most recent financing last, but you also have to allow yourself enough time to achieve your deadlines, such as releasing your alpha, beta and hard launch at the right time. Really knowing the steps you need to take and then allowing yourself time to follow them is essential pacing for any entrepreneur. Being a successful entrepreneur isn’t a sprint, it’s an ultramarathon.


Confidence is a characteristic of wisdom that allows one to make a decision based on one’s experiences. One of my favorite quotes was quipped by Supreme Court Justice Sandra Day O’Connor who said, “maybe in error, but never in doubt.” O’Connor admits she may not always be right, but she drew upon her experiences and intellect to make decisions for the entire country in the wisest way.

I’ve made a number of hard decisions while competing in the Western States 100 six times over the years. Early in this race I was experiencing cramps in my quads, calves, and shins due in part to my limited training. Given I’ve run over 40 ultras, I brought with me a number of salt and electrolyte tablets. Despite pre-race cautionary comments by the race doctor on the dangers of such supplements, I made the choice to take some buffered salt tablets and place them under my tongue, and this sublingual method sent a signal to my body that I was getting salt, and my cramps went away within 10 minutes. I continued to take buffered salt tablets and salt/potassium capsules throughout the day.

In contrast, one of my main ‘value-adds’ to my portfolio companies as a venture capitalist is to share my experiences of working with over 50 companies throughout my 20-year venture career. For example, I encouraged one of my software companies to provide a discount for their clients if they sold multi-year contracts. They were initially concerned about leaving too much money on the table; however, I pointed out that I have seen multiple positive effects with such a business model shift. One of the multiple advantages of such a shift is that the client is more committed to making the product or service a success if the contract is for a larger amount, even if it is for a longer time period.

Deciding to put a controversial supplement in my body during a time of duress or offering major business model altering advice to an entrepreneur based takes confidence based on a broad experience base – aka, wisdom.

Good Judgment

Along the race path there are aid stations every 5 to 8 miles. My natural instinct was to get what I need and leave right away, since after all, it was a race. It was tempting to get out of there as soon as possible and continue running with some of the other runners with whom I was with. However, I decided to stay. Usually when I enter an aid stations I refilled water bottles, graze a bit and leave. But after 20 hours of eating sports gels and salted potatoes, I usually don’t want to eat anything and nothing looks appealing. Given the length of the race, and the importance of keeping my energy level up, I forced myself to hang out at the aid stations after mile 75. I knew that if I took a little extra time, I would see things such as noodle soup, candied ginger and Clif bars that I should try and eat to keep my strength up. Essentially I didn’t know what I wanted, but I knew just by being there I would get getting more calories, which would be critical to complete the race.

Similarly in business, you have to know what you don’t know. I try to account for things that could happen and all the various hypothetical scenarios that could play out, but it’s impossible to anticipate everything that will happen. When I make an early stage investment, I know the average time I will be working with the company will be 6 to 8 years, so I need to plan for all contingencies. Thus, when I write an investment term sheet, I am careful to include various terms that may never happen, such as the ability to sell my shares if a founder sells hers or his (co-sale rights).

Last weekend, I met some really interesting people, made some great friends, and had an unbelievable day and night in the Sierras. While I believe I was making wise decisions, I learned that the reality of wisdom is it’s never fully attained. I learned a lot on that journey – knowledge I’ll draw upon in my next 100 mile race – which is only 2 weeks away!

Note: I am attempting the Grand Slam Ultra Series, consisting of the 4 original 100 miles races in one summer over a 3 month period: Western States 100, Vermont 100, Leadville 100 and the Wasatch 100.