Through a friend in 2009, I met Matt Prince a few weeks before Cloudflare won the Harvard Business School pitch competition. At the time, I also was in business school, & assumed my investment would be embarrassingly small. So I didn’t make the ask. Cloudflare (NYSE: NET) went public in 2019 and today has a $50B market cap.

Lesson: You miss 100% of shots not taken.

In the 2008 financial crisis, Bruno Del Ama & Jose Gonzalez bootstrapped an innovative ETF provider called Global X. I interned later that Summer. Months later, Credit Suisse offered me a full-time position & I accepted it instead of Global X’s offer to be their 1st employee. In 2016, JP Morgan invested and in 2018, Mirae acquired Global X for $488M.

Lesson: Fortune favors the bold.

I played NYC rec league basketball in 2010 with team captain Grant Feek, who jokingly said “I’m the shortest guy on the team, by far.” In 2011, I moved to Hong Kong and had lost touch when Tred launched in 2012. In 2018, we hooped again in Seattle. Off the court, Grant scaled revenue to $100M & Tred was acquired by Cox Enterprises in 2023.

Lesson: Maintain & support your network.

In 2013, Arthur Hayes was laid off in Hong Kong. In 2014 he started BitMex, the first crypto derivative exchange & invented 100x perpetual swaps. When I messaged to buy Bitcoin in 2014, Arthur replied “firstly I need to promo my new business bit-mex.com.” I asked to invest in 2015 (too late). Today, Arthur is one of the youngest billionaires.

Lesson 1: Fortune favors the bold.
Lesson 2: Support your network.

My bschool classmate & friend Rachel Drori launched Daily Harvest in 2015 with $25,000, bootstrapped it to profits in two months, & raised capital to scale while she was pregnant (twice). I had just moved to London & had my head down working as a Trader. Today, DH has over 2 million customers, is valued at $1B+ and generates over $200M in annual revenue.

Lesson: Maintain & support your network.

In 2018, Samar Parikh was leaving Amazon as I was starting. By 2022, he & Nater Youngchild had bootstrapped D8aDriven to $8M rev on 40% EBITDA margins. Samar wanted $1M capital to scale so I called 5 other VCs to join (all declined). A year later, D8a was acquired by Carbon6 & in 2025, Carbon6 was acquired by SPS Commerce for $210M.

Lesson: Write big checks.