2025 Milly Awards LIVE ft. Steph Smith
Three major investing mistakes were revealed: missing out on three $10+ billion companies (Polymarket, Kalshi, and Whatnot) that were begging for investment, and throwing away connections through poor follow-up. Sometimes the biggest losses aren't what you invest in - it's what you fail to invest in
1h 44mKey Takeaway
Three major investing mistakes were revealed: missing out on three $10+ billion companies (Polymarket, Kalshi, and Whatnot) that were begging for investment, and throwing away connections through poor follow-up. Sometimes the biggest losses aren't what you invest in - it's what you fail to invest in when the founders are literally DMing you.
Episode Overview
Year-end awards discussion covering best and worst investments of 2024, featuring stories about missed billion-dollar opportunities, successful stock picks, personal embarrassments, and jury duty disasters.
Key Insights
Missed Opportunities Cost More Than Bad Investments
One host revealed missing three separate $10+ billion investment opportunities (Polymarket, Kalshi, Whatnot) despite being early users and having direct founder connections. The lesson: when you have domain expertise and founder relationships, act on investment opportunities quickly.
Simple Investment Strategies Can Outperform Complex Ones
A diversified stock purchase made on a single day (December 16th) across Shopify, Tesla, Eli Lilly, Google, Bitcoin, and Coinbase returned approximately 35% for the year. This 'Christmas shopping for assets' approach beat many sophisticated strategies.
Personal Health Investments Pay Compound Returns
Taking Accutane for acne after nearly two decades of suffering was described as a life-changing investment. Health improvements, though not financial, can provide outsized returns on quality of life and confidence.
Angel Investing Requires Extreme Patience and Luck
With 56 angel investments, only the top 2-3 deals (returning 100x+) made the entire portfolio worthwhile. The normal hit rate means going through 50+ investments to find 1-2 winners, requiring both patience and stomach for many failures.
Notable Quotes
"I was using Poly Market. I love the thing. The founder is in my DMs... I was like the ultimate in and didn't somehow end up making an investment."
"I operate on gut and swagger. I didn't say I researched these."
"I don't know why more people don't talk about this. And second of all, I'm going to call up my dermatologist and ask why I'm not on Accutane."
"I basically I had to go through 50 of them to get like the one or two winners which is pretty pretty wild."
Action Items
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1
Act on Investment Opportunities with Domain Expertise
When you have deep knowledge in a space and founders are reaching out directly, don't let analysis paralysis prevent you from investing. Set aside dedicated capital for these high-conviction bets.
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2
Implement 'Asset Christmas Shopping' Strategy
Consider making concentrated investments across diversified assets on a single day rather than dollar-cost averaging. Pick 5-6 companies/assets you want to own for 10+ years and invest equal amounts.
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3
Address Health Issues Proactively
Don't suffer with treatable conditions for years. Research solutions, consult specialists, and consider medical interventions that could dramatically improve quality of life.
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4
Maintain Long-term Perspective on Angel Investing
Expect most angel investments to fail and plan for 10+ year holding periods. Focus on finding the 1-2 deals that could return 100x+ rather than optimizing for higher success rates.