The 2025 Milly Awards!

Key Takeaways

The Milly Awards offered unconventional insights into personal and financial investment strategies.
Hosts and guest openly shared significant personal losses and career regrets from the past year.
Influential individuals, recognized as 'Billy of the Year,' were honored for pioneering work and unique life approaches.
Personal challenges, such as a year-long piano commitment, highlighted the rewards of dedicated effort.
Discussions on behavioral economics and community living provided alternative perspectives on wealth and happiness.
Hosts are implementing digital detoxes and new morning routines to enhance productivity and focus.

Sam Parr deployed $1.5 million across five assets: Shopify, Tesla, Eli Lilly, Bitcoin, and Coinbase, allocating 20% to each.
An additional $1.25 million was invested in Google, Coinbase, Bitcoin, Shopify, Tesla, and Eli Lilly for long-term ownership.
One host admitted to buying stocks as a 'shopping spree' rather than through rigorous research, departing from a commitment to index investing.
The investment in Eli Lilly was influenced by information about a new drug rivaling Ozempic and a subsequent positive CEO interview.

Participants noted that many angel investments have gone under, with years three and four identified as the riskiest phase for startups.
One participant stated they have made 56 angel investments, highlighting the need for numerous bets to find a few winners.
Small returns from some exits were observed, alongside the difficulty of identifying successful ventures.
One host passed on opportunities to invest in three startups (Polymarket, Kalshi, Whatnot) that later reached valuations over $10 billion.

Sam Parr recounted mistakenly asking a woman if she was pregnant while she was with her child, leading to an awkward apology and her 'smug smile and a look of disappointment.'
Shaan Puri attempted to avoid jury duty by fabricating a work trip and using his baby as an excuse, but was required to stay for the full duration of jury selection.
Steph Smith shared her biggest personal 'L' was staying in a job, specifically a podcast, for three years longer than she should have.

Sam Parr recognized Steve Houghton, a billionaire in real estate and oil, for demonstrating how wealth can benefit family bonding and comfort within a 17,000 sq ft home.
Steph Smith selected Sebastian Thrun for his pioneering work in self-driving technology, co-founding Waymo and Google X, and his influence in online education with Udacity.
Thrun's initial research group is noted as the origin for many modern leaders in the self-driving car industry, highlighting a profound lineage of innovation.
Jesse Cole, who transformed a minor league baseball team into a highly popular entertainment entity by absorbing sales tax on tickets, was also chosen.

Shaan Puri's 'Coolest Moment' involved playing the piano for the first time for an audience at Jesse Itzler's house, after practicing daily for a year.
His commitment was inspired by Itzler's 'Masogi' concept, a Japanese ritual of undertaking a year-defining challenge.
The performance of 'Nouvelle Beyond Shadow' moved Jesse Itzler, his head of strategy, and Itzler's wife, Sarah (founder of Spanx), to tears.
The experience, described as serendipitous and unplanned, was captured on camera during a podcast recording session, validating his year-long effort.

Will Gadelra, author of 'Unreasonable Hospitality' and inspiration for 'The Bear,' was highlighted for his restaurant 11 Madison's reputation for exceptional customer service.
An anecdote about elevating a street hot dog to a fancy meal illustrated the concept of 'unreasonable hospitality' and excellence.
Sean Frank, CEO of Ridge Wallet, was a favorite guest for his directness and stated ambition to sell Ridge for $1 billion within three years.

Kristen Berman, a partner at Irrational Labs with behavioral economist Dan Ariely, consults companies like Panda Express on framing choices to encourage desired behaviors.
Instead of upgrading her lifestyle, Berman purchased surrounding apartments to create a compound with friends, prioritizing community and happiness based on data.
This strategy diverged from typical wealth accumulation and isolationist tendencies observed in others, demonstrating an alternative approach to using money.
One host shared a similar personal experience of intentionally buying homes near friends to enhance life quality through fostering close-knit communities.

One host decided to delete social media apps including X, Twitter, YouTube, and Reddit, aiming to reclaim 10-15 hours per week for activities such as reading.
This decision was described as a 'Luka Doncic trade,' exchanging social media consumption for reading, and was initiated on a flight.
Another host is experimenting with a similar social media detox, using a 'brick' device for phone restrictions, though still accessing platforms on their computer.

Steph Smith expressed nervousness about potentially having another child, seeking insights into what makes having children rewarding, particularly for women.
Shaan Puri described the profound impact of having young children, likening it to entering the 'real game' of life and finding joy in children experiencing the world for the first time.
The conversation explored how fatherhood deepens feelings of love and fulfillment, making one less self-centered and more present.
Speakers acknowledged potential downsides, such as loss of personal time, but emphasized the overriding joy and sense of purpose from dedicating oneself to family.

A tweet was discussed suggesting that tapping a credit card is 'spiritually passive and feminine behavior,' contrasting it with men 'penetrating' the chip reader.
A wholesome tweet by Jay Yang stated, 'Real success is how many people thank you for theirs,' which was presented as a profound metric for success.
The speakers discussed the consumption of inspirational and motivational content, noting a potential trend where people in the early or later career stages consume more.