The 2025 Milly Awards! - My First Million Recap
Podcast: My First Million
Published: 2025-12-18
Duration: 1 hr 42 min
Guests: Steph Smith
Summary
Sam Parr, Shaan Puri, and Steph Smith host the annual Milly Awards, reflecting on their best and worst investments, personal wins and losses, and standout moments of the year. Packed with humor, candid stories, and actionable insights, this episode captures the highs, lows, and lessons from 2025.
What Happened
The episode begins with Sam, Shaan, and Steph discussing their best investments of the year, ranging from financial wins like Shaan's 35% portfolio growth to personal life changes like Sam's happiness-boosting move to New York City and Steph's life-changing experience with Accutane after two decades of acne struggles.
The trio moves into their worst investments of the year, where Sam reflects on losing money by holding on to HubSpot stock too long, Steph recalls investing in a bubble tea company that folded, and Shaan laments missed opportunities to invest in breakout companies like WhatNot and Polymarket, which have now soared in valuation.
They share their biggest personal losses next, with Sam telling a painfully awkward story about mistakenly asking a woman when she was due, Shaan recounting his struggles to dodge jury duty, and Steph admitting she stayed too long in a job that no longer aligned with her passions.
The group then celebrates their coolest moments of the year. Highlights include Sam meeting billionaire Steve Houghton, whose family dynamic and generosity left a lasting impression, Shaan performing a piano piece at Jesse Itzler's house after a year of practice, and Steph taking her dad to the World Series, fulfilling a lifelong dream.
For Billy of the Year, Sam selects Steve Houghton for his inspiring balance of wealth and family values, Steph highlights Sebastian Thrun for his pioneering work in self-driving cars and lifelong innovation, and Shaan chooses Jesse Cole for transforming a minor league baseball team into a global entertainment phenomenon with the Savannah Bananas.
In the frame-breaking person category, Sam reflects on Will Guidara and his philosophy of 'Unreasonable Hospitality,' which challenges how excellence and human connection can redefine industries. Steph shares the story of Fiona Oaks, a vegan ultra-marathoner with no kneecap who runs to fund her animal sanctuary. Shaan spotlights Kristen Berman, who uses behavioral economics to engineer happiness by building a community-driven living environment instead of upgrading her lifestyle.
Lastly, the group discusses their biggest changes for 2026. Shaan plans to quit consuming social media to focus on reading the best books ever written, Sam is doubling down on content creation to grow his company Hampton, and Steph considers embarking on parenthood while continuing to push herself as a runner.
Key Insights
- Jesse Cole turned the Savannah Bananas, a minor league baseball team, into a global phenomenon by ditching traditional baseball rules for fan-first entertainment. From choreographed dances to mid-game player interviews, he reinvented the experience entirely, proving that breaking the mold can be more valuable than optimizing within it.
- Will Guidara’s concept of 'Unreasonable Hospitality' flips the script on customer service by making human connection the product, not a byproduct. His philosophy turns small acts—like customizing a meal to a diner’s life story—into unforgettable moments that redefine what excellence looks like.
- Fiona Oaks runs ultramarathons without a kneecap, using her winnings to fund an animal sanctuary instead of personal goals. Her story challenges the typical narrative of athletic success, proving that purpose, not perfection, can drive extraordinary achievements.
- Shaan plans to quit social media and focus on reading history’s best books, arguing that most people trade deep knowledge for shallow consumption. His bet is that timeless wisdom will outpace fleeting trends, creating compounding advantages over time.
Key Questions Answered
What were the best investments shared on My First Million's Milly Awards episode?
Shaan's one-day stock spree, which returned an average of 35%, stood out. He invested in companies like Shopify, Tesla, Eli Lilly, and Bitcoin. Sam's best investment was moving to New York City, while Steph highlighted the life-changing impact of Accutane.
Who is Jesse Cole, and why did Shaan Puri call him a Billy of the Year?
Jesse Cole is the founder of the Savannah Bananas, a minor league baseball team turned global entertainment sensation. Shaan praised his creativity, passion, and customer-first approach, which include practices like eliminating ticket service fees.
What is Will Guidara's philosophy of Unreasonable Hospitality?
Will Guidara's philosophy emphasizes going above and beyond to create extraordinary experiences, as demonstrated in his Michelin-starred restaurant Eleven Madison Park. For example, his team served a New York street hot dog to international guests who had mentioned missing the experience.