The 2025 Milly Awards!

Episode Summary

Executive Summary: End-of-year rapid-fire awards episode featuring Steph, Sam, and Sean, mixing personal reflections with business lessons. The hosts discuss best and worst investments, biggest personal losses, frame-breaking guests, coolest moments, and habits for the coming year, while highlighting growth in their podcast and ventures. Themes include long-term investing, family/community, content creation, discipline, and inspirational people who redefine ambition.

Main Topics: Best investments of the year (Priority: 5/5): Sam frames his best investment as buying and moving into a furnished New York City apartment, while Steph cites Accutane as a life-changing personal investment and Sam also details a concentrated stock basket that performed well over the year. Worst investments and missed opportunities (Priority: 5/5): Steph names networking events and a failed bubble tea investment as poor bets; Sean highlights missed startup investments in Polymarket, Kalshi, and Whatnot that later became billion-dollar companies, and also mentions losing on HubSpot stock. Biggest personal Ls (Priority: 4/5): The hosts share embarrassing or painful personal setbacks: Sean’s jury duty ordeal, Steph staying too long in a previous job, and Sean’s awkward pregnancy assumption at a party. Coolest moments of the year (Priority: 5/5): Sean’s piano performance at Jesse Itzler’s house and Steph’s trip to the World Series with her dad stand out as deeply emotional, high-signal moments; Sam also emphasizes Jesse Itzler’s inspiring presence. Frame-breaking people and favorite guests (Priority: 5/5): The episode highlights guests and figures who exceeded expectations or changed perspectives, including Jesse Cole, Will Guidara, Nick Mowbray, John Morgan, Sean Frank, Kristen Berman, Sebastian Thrun, and Fiona Oakes. New habits and next-year changes (Priority: 4/5): Sean plans to delete social apps and reduce consumption, Steph focuses on running and early mornings, and Sam emphasizes more content creation plus an earlier workout routine. Family, community, and living a rich life (Priority: 4/5): Several segments emphasize wealth as a tool for better living—being near family, buying time and community, and prioritizing relationships over status or accumulation.

Key Arguments: Long-term ownership beats constant trading; Sam’s one-day stock purchases were intended as 10-year holds and outperformed on a blended basis. Personal well-being can be a better investment than financial assets, as shown by Steph’s Accutane experience and Sam’s move to New York City. Some of the most valuable opportunities are missed by inaction, illustrated by Sean passing on Polymarket, Kalshi, and Whatnot. Network-heavy events often have negative expected value for some people; Steph argues most conferences are not worth the emotional cost. Frame-breaking people provide a useful standard for excellence by revealing new levels of ambition, craft, or discipline. Money should be used to improve life, not as a status metric; Kristen Berman’s housing decision is offered as a concrete example. Discipline compounds when tied to identity and schedule, as seen in early workouts, running, and social-media deletion. Family and meaningful relationships can be an underrated return on investment, from Jesse Cole’s hospitality to Steph taking her dad to the World Series.

Data Points: Podcast views/downloads in last 12 months: about 90 million - Sean cites combined views and downloads across platforms for the year Total subscribers across platforms: close to 2 million - Mentioned for YouTube, Spotify, and Apple Previous viral short/video: 30 million views - Sean references an Elon Musk story that performed heavily last year Steph’s Accutane treatment duration: 6 months - She says she took Accutane this year and is now clear Sam’s stock allocation count: 5-6 positions - He bought several stocks in a one-day “Christmas shopping” spree Sam’s total invested amount: $1.25 million - Approximate total spread across Google, Shopify, Tesla, Eli Lilly, Bitcoin, and Coinbase Shopify return: up 53% - One-year performance of Sam’s purchase Tesla return: up 16-17% - One-year performance of Sam’s purchase Eli Lilly return: up 35% - One-year performance of Sam’s purchase Google return: up 50% - One-year performance of Sam’s purchase Coinbase return: up 1% - One-year performance of Sam’s purchase Bitcoin return: down 8% - One-year performance of Sam’s purchase Angel investments Sean has made: 56 - Sean says he’s done 56 angel deals Angel investments Steph has made: about 15 - Steph estimates her count Top-line angel return expectation: 3-4x over 10 years - Sean’s conservative estimate for angel investing Jesse Cole company scale: 100M+ - Sean describes the Savannah Bananas business as bootstrapped to over $100M Blue Jays World Series wins: 2 titles (1992, 1993) - Steph references her father’s lifelong fandom Steph’s marathon time: 3:30 - She says her second marathon was just under eight-minute miles Podcast guest estimate for MrBeast’s home event: 90th richest person in the world - Sean recalls one attendee at the MrBeast gathering Sebastian Thrun’s AI course enrollment: 160,000 students - He released an online Introduction to AI course for free Waymo/robotaxi scale anecdote: 8 Waymos at one intersection - Steph describes the normalization of autonomous cars in San Francisco Fiona Oakes marathons: 248 marathons - Steph cites the athlete’s extraordinary running record Billionaire company valuations missed by Sean: above $10 billion each - Polymarket and Kalshi are described as now being above $10B valuations

Pivotal Quotes: "I operate on gut and swagger." — Sean: Explaining how he chose stocks without much research or formal analysis "Real success is how many people thank you for theirs." — Jay Yang (quoted by Steph): Used as a defining principle for what success should mean "I will die for you." — Sean: Describing the emotional shift after having children and the depth of parental commitment

Implications: Listeners are encouraged to think longer-term about money, career, and habits; invest in health, family, and community; and seek people and experiences that challenge their assumptions. The episode suggests status games matter less than building a life that feels rich and durable.