Today we have Michael Phelps on what it takes to be the best in the world, Tom Gayner on building a “Baby Berkshire”, Corey Hoffstein on lessons he learned in 2020, and George Kinder on why life planning is important.

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Investing

We Study Billionaires: TIP332: Long-Term Investing w/ Tom Gayner. Tom Gayner is the Co-CEO of Markel Corporation, which has been referred to as a “Baby Berkshire” because it is structured similarly to Berkshire Hathaway. He explains the framework he’s used to generate stellar returns for over 40 years, looking for four things when analyzing an investment: profitable without leverage, talented management with integrity, capital discipline, and fair price. He elaborates on each of the four, covers the structure of the firm and the use of a rolling five year average to judge performance, and then talks about navigating 2020. [January 16, 2021–1 hour, 1 minutes] iTunes Podcast | Spotify | Google | Breaker | Website Linkv

This Week in Startups: David Tisch shares insights from 350+ early-stage investments in companies like Plaid & Roman, importance of reputation, dealing with sharp-elbowed investors & more. Tisch is managing partner of BoxGroup, a seed-stage capital firm, and a co-founder of TechStars New York City and talks with Jason Calacanis about the past and present of angel and venture investing. They talk about how it’s changed over the past 10 years, now no longer having to recruit both companies and other angel investors to events. They take a broad look at how their careers have changed now that they have funding from LP’s. They also touch on other investments, such as Plaid (which just broke up with Visa), best practices when working with founders, and the importance of maintaining a strong reputation during your career. [January 21, 2021–1 hour, 20 minutes] iTunes Podcast | Spotify | Google | Breaker | Website Link

The Long View: George Kinder: A Financial Plan Needs To Be a Life Plan. Kinder is the founder of the Kinder Life Institute, which trains financial professionals in the field of what’s called Life Planning. The episode focuses on this topic and the idea that advisors should help people use their money to make them happy, not maximize returns. He covers the famous three questions he uses to help people determine what they want in life and explains how he works with advisors to help equip them to have these types of conversations with their clients. [January 20, 2021–43 minutes] iTunes Podcast | Spotify | Google | Breaker | Website Link

Odd Lots: The Important Lesson a Quant Manager Learned in 2020. Corey Hoffstein is a fund manager at Newfound Research, which employs trend following and momentum signals in its trading. He talks about the lessons he learned from how the market performed during 2020. Although he says you’d expect a trend following strategy to have underperformed with the sharp changes in trends, he was surprised by how it played out and talked about the lessons he learned. He touches on the impact of the Fed stepping in, not to complain, but to say that he thinks that may be leading to sharper reversals over time. He also discusses the spectrum of quantitative to qualitative and possibly needing to step in to override a strategy. Lastly, he hits on why he thinks tail risk within the market has increased over time. [January 21, 2021–53 minutes] iTunes Podcast | Spotify | Google | Breaker | Website Link

I can’t control the field, I can’t control the game I’m playing. I just have to play the game.

The Meb Faber Show: #280 — Matthew O’Connor, AdQuick — People Use The Term Disrupt All The Time…And I Like To Think We Can Kind Of Help Erupt The Industry. O’Connor is the co-founder of AdQuick, a marketplace for out-of-home (billboard) advertising. He became interested in the idea after he started at Instacart as one of the first few employees working to grow it market by market. He talks about the early days at Instacart and then dives into building the company. He explains why purchasing a billboard advertisement is so difficult historically, why billboards frequently go unused, and how the marketplace is benefitting users and consumers by providing better data. He also explains why DTC brands are embracing billboards in middle America and how Reddit co-founder & AdQuick investor Alexis Ohanian used the platform to do a huge campaign for his wife, Serena Williams, when she was going back to her first tennis match after a break from the sport, which generated a lot of publicity. [January 18, 2021–55 minutes] iTunes Podcast | Spotify | Google | Breaker | Website Link

The Meb Faber Show: #281 — Adrian Helfert, Westwood Group — We’re Fundamental Investors And Multi-Asset Investors That Can Look Across The Capital Spectrum. Helfert is the Director of Multi-Asset Portfolios for Westwood Group, where he leads Westwood’s multi-asset strategies group. This episode takes a broad look at all asset classes around the world, including bonds, stocks, and TIPS. He offers ideas on how to look for income with MLP’s and REIT’s to earn income with rates at ~0% and why TIPS are an attractive insurance policy against possible future inflation. He also touches on the energy sector, gold miners, and the impact low rates have had on growth stocks. [January 20, 2021–48 minutes] iTunes Podcast | Spotify | Google | Breaker | Website Link

The Rest

The Tim Ferriss Show: #494: Michael Phelps and Grant Hackett — Two Legends on Competing, Overcoming Adversity, Must-Read Books, and Much More. This is one of the best episodes on both mental health and what it takes — both mentally and physically — to be the best in the world. Phelps is the greatest swimmer of all time and Hackett was the captain of the Australian national team and set 16 world records. The two good friends talk about their journeys, handling the mental pressure to perform, and what it takes to consistently perform at an elite level.[January 21, 2021–1 hour, 56 minutes] iTunes Podcast | Spotify | Google | Breaker | Website Link

“Trying to do something that no one’s ever done before, you really have to approach it in every single different way possible than ever has been done before. There is no blueprint for it.” — Michael Phelps

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