The 2025 Milly Awards!

December 18, 2025

102 min episode · 2 min read

Episode

102 min

Read time

2 min

AI-Generated Summary

Published Dec 21, 2025

Key Takeaways

✓Investment Strategy: Sam bought five stocks on December 16th without research - Shopify, Tesla, Eli Lilly, Bitcoin, Coinbase, Google - achieving 35% blended returns by focusing on ten-year hold periods rather than trading.
✓Angel Investing Reality: Expect three to four times returns over ten years from angel investments, with success depending entirely on your top four deals achieving 50-100x returns while most investments fail completely.
✓Personal Injury Law Business: John Morgan built Morgan & Morgan into a billion-dollar law firm by focusing on profit-sharing with employees, aggressive marketing, and fighting insurance companies for common people rather than chasing prestige cases.
✓Lifestyle Design Framework: Behavioral economist Kristen Berman bought multiple apartment units around her existing home to create a micro-community with friends as neighbors, prioritizing relationships over luxury upgrades when spending money.
✓Networking Event ROI: Steph identifies networking events as her worst investment, recommending selective attendance only when you have existing relationships to reconnect with rather than trying to make new professional connections.

What It Covers

The My First Million hosts and guest Steph conduct their annual "Milly Awards" reviewing 2025's best investments, worst decisions, coolest moments, and frame-breaking people they encountered.

Key Questions Answered

•Investment Strategy: Sam bought five stocks on December 16th without research - Shopify, Tesla, Eli Lilly, Bitcoin, Coinbase, Google - achieving 35% blended returns by focusing on ten-year hold periods rather than trading.
•Angel Investing Reality: Expect three to four times returns over ten years from angel investments, with success depending entirely on your top four deals achieving 50-100x returns while most investments fail completely.
•Personal Injury Law Business: John Morgan built Morgan & Morgan into a billion-dollar law firm by focusing on profit-sharing with employees, aggressive marketing, and fighting insurance companies for common people rather than chasing prestige cases.
•Lifestyle Design Framework: Behavioral economist Kristen Berman bought multiple apartment units around her existing home to create a micro-community with friends as neighbors, prioritizing relationships over luxury upgrades when spending money.
•Networking Event ROI: Steph identifies networking events as her worst investment, recommending selective attendance only when you have existing relationships to reconnect with rather than trying to make new professional connections.

Notable Moment

Sean learned piano for eleven months as his personal challenge, then surprised Jesse Itzler by playing an Italian composition on Itzler's deceased mother's piano, moving everyone present to tears in an unplanned moment.

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