The 2025 Milly Awards
Start small with stock picking by dedicating a specific amount (like $1.25M) to quality companies you understand and plan to hold for 10 years. Sean's 'Christmas shopping' approach - buying Tesla, Shopify, Google, Eli Lilly, and Bitcoin on one day - returned 35% in a year because he focused on long-
1h 39mKey Takeaway
Start small with stock picking by dedicating a specific amount (like $1.25M) to quality companies you understand and plan to hold for 10 years. Sean's 'Christmas shopping' approach - buying Tesla, Shopify, Google, Eli Lilly, and Bitcoin on one day - returned 35% in a year because he focused on long-term ownership rather than trading.
Episode Overview
Sam, Sean, and Steph share their annual awards covering best and worst investments, biggest personal failures, and memorable moments from their podcast year that reached 90 million views.
Key Insights
Long-term stock picking beats day trading
Sean's strategy of buying stocks he wants to own for 10 years, not trade, generated 35% returns. His picks included Tesla (up 17%), Shopify (up 53%), and Google (up 50%) because he focused on companies he believed in long-term rather than short-term movements.
Personal investments often outweigh financial ones
Sam's biggest investment was moving to New York City to be closer to family and work in-person, which significantly improved his happiness. Steph invested in Accutane treatment for lifelong acne, calling it transformative after 19 years of unnecessary suffering.
Angel investing requires extreme patience and selective focus
Both hosts acknowledge angel investing's brutal reality: out of 50+ investments, only 1-2 become meaningful winners. Sean estimates 3-4x returns over 10 years, but success depends entirely on hitting the rare 100x+ winners that make up for all the losses.
Missed opportunities hurt more than actual losses
Sean's biggest regret was passing on three $10+ billion startups (Polymarket, Kalshi, Whatnot) despite being perfectly positioned to invest. He was an early user of these platforms and had direct founder relationships but failed to act on obvious opportunities in his expertise areas.
Staying too long in wrong situations costs compound time
Steph's biggest mistake was staying in a prestigious job for 3 years despite knowing it wasn't the right fit. The lesson: don't let others' expectations or prestige trap you in roles that don't align with what energizes you.
Notable Quotes
"I don't do index funds and bonds because imagine if I'm one day on a podcast and they ask me about my best investment of the year. And I can't I have to start talking about seeing my mother-in-law."
"I took Accutane for 6 months this year and I'm clear. And I think it's like, you know, obviously your mileage may vary. Go talk to a doctor. But I'm just like, this is the best thing ever."
"I operate on gut and swagger. Okay. Um, and so the the the diff since then the the CEO of Eli Liy has come on and um cuz Lily has turned into like a trillion dollar company."
"I realized I found out this year that I had I passed on three different $10 billion startup investments that were right in my wheelhouse."
"My biggest personal L um was staying in a job too long. No shade to my previous employer, but I think the epitome of when other people think you should be good at something and you think therefore you should be good at something."
Action Items
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1
Create a 10-year stock holding strategy
Instead of day trading, pick 4-6 companies you understand and believe in for the next decade. Allocate a fixed amount across them and resist the urge to check daily performance or make frequent trades.
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2
Address persistent health issues immediately
Like Steph with Accutane, stop accepting chronic problems as 'normal.' Research proven treatments and consult specialists rather than hoping issues resolve naturally over time.
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3
Audit your current role for energy alignment
Ask yourself: Does this energize me or drain me? Are you staying due to others' expectations or genuine fit? If it's the former, start planning your transition to work that aligns with your strengths and interests.
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4
Act on obvious opportunities in your expertise area
When you encounter products/companies in your field that you use and love, especially with founder relationships, don't overthink the investment decision. Your domain expertise gives you an edge - use it.