Infinite Games – Launching the Compound Kings ETF and Building an Investment Process with Robert Cantwell of Upholdings

“I think the best investors are operators and the best operators are investors.” – Robert Cantwell

In this episode of Outliers, I’m talking with Robert Cantwell about his thoughts on ETFs, how great investors tend to think like founders, and why blockchain is his latest investment interest.

Robert Cantwell is the Founder of Upholdings, the first hedge fund in the U.S. to convert into an ETF with the launch of Compound Kings (KNGS). Robert started his career as an Analyst at Elevation Partners, which was co-founded by U2’s lead singer Bono. He then worked at the long/short hedge fund Meru Capital before serving as Everlane’s CFO for 5 years. Robert founded Upholdings in 2019 and launched Compound Kings (KNGS) in 2020. To date, Compound Kings has dramatically outperformed the S&P 500.

Chapters in this interview:

00:00:37 – Robert’s thoughts on the evolving ETF space
00:04:12 – Why a concentrated portfolio is important
00:10:19 – Robert’s business background that led him to found Upholdings
00:15:10 – Robert’s experience with Elevation Partners working with Bono
00:19:47 – Lessons learned as an investor vs. an operator
00:24:43 – Background on Compound Kings (KNGS)
00:32:27 – On share repurchases
00:37:58 – Inspiring investors
00:39:55 – On investing in Palm earlier in his career
00:44:21 – Why now is the worst time to invest in technology and innovation, aside from blockchain
00:51:49 – Why the best investors are operators and the best operators are investors
01:00:55 – Misconceptions about Chinese technology companies
01:13:50 – Upholdings’ investment process
01:18:53 – Mandates and regulations around ETFs
01:21:58 – Robert’s advice to investors