#130 Robert Cantwell of Compound Kings: My Favorite Books, Tools, Habits and More | 20 Minute Playbook

In Episode #130, we deconstruct Robert Cantwell's peak performance playbook—from their favorite book to the tiny habit that's had the biggest impact on their life. Robert is the Founder of Upholdings and Portfolio Manager of Compound Kings. We cover longevity in investing, source documents, and learning from fintwit.
Last updated
September 12, 2022
Min Read
Robert Cantwell previously supported leading growth companies as an investor at Elevation Partners, and as an operator at Everlane.
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About Robert Cantwell

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“I wish someone told me that who you work with peer-wise is the number one driver of whether or not you enjoy working or not.” – Robert Cantwell

Robert Cantwell is Founder of Upholdings and Portfolio Manager of Compound Kings, which is an exchange traded fund focused on investing in compounders. I had Robert Cantwell on last year in episode 23, where he joined me shortly after launching Compound Kings in late 2020. Before founding Upholdings and launching Compound Kings, Robert had an incredible career, both as an operator and an investor. 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 CFO for five years. Robert founded Upholdings in 2019 and officially launched Compound Kings in late 2020.

In this episode, we cover why Robert is obsessed with how we think, process information and make decisions. The single biggest lessons that Robert has taken away from launching and scaling Compound Kings over the last two years, how being a compounding focused investor is different than being solely growth or value focused, why he skips to the back of investment books and goes straight to the source material to form his own opinions about the contents of the book, the investing tools that he and his team use daily at Compound Kings to beat the S&P 500, and his three-step process for consuming thinking through and ultimately coming to conclusions about everything that he reads.

For more, explore the transcript of this episode.


In this episode, we deconstruct Robert Cantwell’s peak performance playbook—from their favorite book to the tiny habit that's had the biggest impact on their life. In it we cover:

  • (00:00:00) – Introduction
  • (00:02:13) – Longevity in investing
  • (00:03:37) – Investment philosophy at Compound Kings
  • (00:09:05) – Source documents can level up investment knowledge
  • (00:11:23) – Consuming info vs. processing info
  • (00:14:02) – Key tools and learnings from fintwit
  • (00:16:30) – Who you spend your time with is paramount

Listen to the episode on Apple Podcasts, Spotify, Overcast, Google Podcasts, Amazon Music, Castbox, Pocket Casts, Player FM, Podcast Addict, iHeartRadio, or on your favorite podcast platform. You can watch the interview on YouTube here.

An Idea Worth Trying

Robert recommends using source documents as a resource when researching investments. Look for anything from court transcripts to earnings calls to round out your research.

Our Favorite Quotes

Here are a few ideas we'll be thinking about weeks and months from now:

  • “In investing, longevity is the number one recurring theme amongst people that have successful careers in it. And so when you think about longevity, you want to think about what are the things that you need in order to attain that?”
  • “The biggest takeaway is that the investment management business is not, in fact, different from any other business. It is about products, marketing, and distribution, and you've got to be superior at all three of those things to build a business that matters. It turns out that investment management is not in fact just about investing.”
  • “We are focused on the businesses that are putting capital into the highest return on investment opportunities and then trying to pay the best price relative to getting that really high ROIC that those companies are able to achieve with what they're doing.”
  • “Source documents has become a fascinating thing, whether it could be court transcripts, it could be earnings calls, it could be an old piece of research that was put out by university. And what I've enjoyed about going deeper into source documents is that it challenges you to come up with your own conclusion on something, as opposed to relying on a news outlet or another writer to offer their interpretation of it.”

Selected Links

We covered a lot of ground in this interview. Here are links to the stories, articles, and ideas discussed:

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