What Matters Most And Why?

This past summer, I applied to a few MBA programs, including Stanford. Stanford has a famous essay question which I’ve used to title this post. It’s not a bullshit essay; it requires serious introspection. Writing it was cathartic. While I’m headed to Wharton and not Stanford, I wanted to share a lightly edited version of my response.

What matters most to me is seizing opportunities that come from moments of chance.

I was adopted into a loving family at birth, something my parents never kept from me. Their perspective was important: this was not a handicap. Just like people have brown hair or blue eyes, some people are adopted. When I was young, I would introduce myself to people and say, “Hi, I’m Tim, and I’m adopted!” I later realized our approach to the situation wasn’t the only path. Friends I met later in life believed their adoption was an impediment, which ultimately disrupted their lives. Because of my parents’ influence, I viewed mine as a conversation starter and an opportunity.

When I was a college junior, my father passed away unexpectedly. I responded by sleeping fifteen hours at a time and withdrawing. But my mother refused to let my brother or me use this unfortunate turn of events as an excuse. She led by example: going out to dinner, taking us on weekend trips, and encouraging us to return to life. I was scheduled to study abroad that spring and thought about canceling the trip. She suggested I reconsider. I went and visited countries across the Pacific Rim and studied in Australia.

In Oz, my new friends Mike and Colin and I purchased a burnt orange station wagon that we named after its original owner.

We drove Bert for hours to discover secluded beaches, waking up at dawn to hit the waves (or in my case the golf course). Australia is also where I met my wife, Meg.

Without taking on my mother’s positive perspective, I would have missed these chances to develop my self-reliance, capitalize on serendipitous circumstances, and pick out the Southern Cross constellation.

The increased confidence I gained on that trip helped me launch a career during the 2008 financial crisis, when jobs were being cut left and right. My first role at JPMorgan wasn’t glamorous. I moved money around for investment funds. But it was tied to venture capital and my foot was in the door. Within my first few weeks, my dad’s former boss Tim invited me out to lunch. He gave me an important piece of advice: ask for more work. I took it to heart.

Whenever I finished my daily required duties, I approached people within my group I admired, telling them I wanted to learn about what they were doing and would volunteer my time. Suddenly I had entrée into the managing director of sales, vice president of product, and executive director of performance reporting. These people charged me with creating sales proposals for important pitches, fleshing out new products in response to client needs, and solving bugs within performance models. Capitalizing on those opportunities, I gained great experience, better mentors, and a path more closely aligned with my career goal of becoming a VC. A few years later, this experience (along with much networking) was the foundation I needed to quit my job and launch Pilot Mountain Ventures with my colleagues Steve and Willy.

This same natural inclination towards saying yes and eye towards new opportunities led me to attend far too many networking events before and after joining the venture community. The events were filled with pizza, beer, and awkward conversations. Rock climbing one evening with friends from other startups, we bemoaned the state of networking. We wondered why it couldn’t be casual and relaxed. Ideas for a better, more supportive entrepreneurial community festered in my brain. I told them I wanted to experiment with something called Startup Climbing. I got their feedback, sought advice from a few others, and three weeks later hosted my first event. It was during the holidays and eight people showed. I considered it a successful event: it wasn’t just me who sought something different.

Over the next few months, eight became thirty and then sixty. I tried different distribution channels, like Facebook, email, Meetup, and Slack. I asked attendees for ideas and incorporated them, negotiating discounts and even free drinks for after the climb. Some things worked, many didn’t. But I watched as a community developed. People returned and brought their friends. I tried to embed an easygoing supportive culture by greeting strangers in a familiar manner and connecting them with other members and business opportunities.

I knew it was working when I sat down after a climb, perfectly sweaty and happy, and someone who had climbed with me for two months asked, “What do you even do for a living?” Instead of developing business connections, we’d built a friendship. In over two years, Startup Climbing counts nearly 10,000 members across New York, LA, Boulder, Boston, Raleigh, and soon to be Philly.

The best part about creating and being ready for new opportunities continues to be the non-linear impact of the experiences I embrace on my life and the others involved in it. I’m more capable to love my family, handle adversity, learn from mentors, find business opportunities, and personally develop because I’m always prepared to seize chance.

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