Uploaded October 2025 | Updated September 2026, 2 weeks ago
Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the European market open, and the emotional asymmetry of managing billions of dollars. They cover why he thinks successful private companies should avoid the public markets, the real genius of Elon Musk's business approach, and the pattern recognition that comes from years of investing. This is a rare, candid look into the strategies and mindset of a top public markets investor.
Show notes
• [Read] The Essays of Warren Buffett: Lessons for Corporate America by Lawrence A. Cunningham | amazon.com/Essays-Warren-Buffett-Lessons-Corporate/dp/161283383X
• [Read] The Buffett Partnership Letters (1957-1970) | ivey.uwo.ca/media/2975913/buffett-partnership-letters.pdf
• [Read] Value Investors Club (VIC) | ValueInvestorsClub.com
Full transcript on Substack: cheekypint.substack.com/p/dan-sundheim-of-d1-capital-on-the
Subscribe to Cheeky Pint
Spotify: open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFw
Apple Podcasts: podcasts.apple.com/us/podcast/cheeky-pint/id1821055332
Substack: cheekypint.substack.com
Key moments
00:00 The D1 operating model
07:54 Getting it wrong on NFLX
11:44 What makes a good stock picker
18:16 Portfolio-building
24:35 GameStop
35:57 The art of short-selling
41:48 How to spot a turnaround
47:12 Waking up at 3 AM
53:14 Money management
59:31 Dan’s 10-year hands-off stock pick
01:09:52 China
01:14:44 Are we in a bubble?
01:20:41 SpaceX
01:25:04 Investing in private companies
01:32:55 Thoughts on the banking industry
01:35:58 Advice for budding investors
Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the European market open, and the emotional asymmetry of managing billions of dollars. They cover why he thinks successful private companies should avoid the public markets, the real genius of Elon Musk's business approach, and the pattern recognition that comes from years of investing. This is a rare, candid look into the strategies and mindset of a top public markets investor.
Show notes
• [Read] The Essays of Warren Buffett: Lessons for Corporate America by Lawrence A. Cunningham | amazon.com/Essays-Warren-Buffett-Lessons-Corporate/dp/161283383X
• [Read] The Buffett Partnership Letters (1957-1970) | ivey.uwo.ca/media/2975913/buffett-partnership-letters.pdf
• [Read] Value Investors Club (VIC) | ValueInvestorsClub.com
Full transcript on Substack: cheekypint.substack.com/p/dan-sundheim-of-d1-capital-on-the
Subscribe to Cheeky Pint
Spotify: open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFw
Apple Podcasts: podcasts.apple.com/us/podcast/cheeky-pint/id1821055332
Substack: cheekypint.substack.com
Key moments
00:00 The D1 operating model
07:54 Getting it wrong on NFLX
11:44 What makes a good stock picker
18:16 Portfolio-building
24:35 GameStop
35:57 The art of short-selling
41:48 How to spot a turnaround
47:12 Waking up at 3 AM
53:14 Money management
59:31 Dan’s 10-year hands-off stock pick
01:09:52 China
01:14:44 Are we in a bubble?
01:20:41 SpaceX
01:25:04 Investing in private companies
01:32:55 Thoughts on the banking industry
01:35:58 Advice for budding investors
