Through a friend in 2009, I met Matt Prince weeks before Cloudflare won the Harvard Business School pitch competition. Just out of the Army, I was also in business school and assumed my investment would be too small. Cloudflare (NYSE: NET) went public in 2019 and today has a $80B market cap.

Lesson: You miss 100% of shots not taken.

In 2008 during the financial crisis, I interned under Bruno Del Ama & Jose Gonzalez as they were bootstrapping an innovative ETF provider called Global X. Months later, Credit Suisse offered me a full-time position & I accepted it instead of the offer to be Global X’s 1st employee. After raising capital from J.P. Morgan, Mirae acquired Global X for $500M in 2018.

Lesson: Fortune favors the bold.

I played NYC rec league basketball in 2010 with Grant Feek, who jokingly said he was “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 2014, Arthur Hayes started BitMex, the first crypto derivative exchange, inventing 100x perpetual swaps. When I messaged to buy Bitcoin from him in 2014, he replied, “firstly I need to promo my new business bit-mex.com.” A year later, I wanted to invest in BitMex (too late). Today, Arthur is one of the youngest crypto billionaires.

Lesson 1: Fortune favors the bold.
Lesson 2: WAGMI.

My bschool classmate & friend Rachel Drori launched Daily Harvest in 2015 with $25,000, bootstrapped to profitability, & raised capital while she was pregnant (twice). As I moved from Hong Kong and London / Dublin in 2015-2016, I missed her early raises. In 2021, Daily Harvest became a unicorn generating $200M+ of revenue and was acquired by Chobani in 2025.

Lesson: Maintain & support your network.

In 2018, West Point grad 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 bigger checks.