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My First MillionThe 12 Awards Of 2023: No.1 Unsexy Business, Wildest Predictions & More
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WHAT IT’S REALLY ABOUT
Milly Awards: delusional characters, investing wins/losses, and unsexy winners
- The episode runs “part two” of the hosts’ annual Milly Awards, covering categories like most delusional person met, best/worst investments, unsexy business, content of the year, predictions, coolest moment, and breakout of the year.
- Sam Parr’s “most delusional” pick focused on Val, an under-the-radar operator with extreme work habits and a large, bootstrapped business portfolio, while another speaker contrasted that with Michael Dell as an unusually steady, low-flash billionaire.
- The investing segment ranged from opportunistic acquisition (a speaker buying a majority stake in Letterboxd after a coffee meeting) to cautionary tales about unfocused acquisitions (Castro as a “money bonfire”) and the slow, frustrating nature of angel investing returns.
- In “unsexy business,” the group highlighted scalable, non-glamorous winners like an HVAC roll-up story and Pantone’s standardization and licensing model, emphasizing how boring categories can produce large outcomes.
- The content, prediction, and breakout sections spanned TV/books and AI anxieties (including assistant/admin work disruption), with Ozempic/GLP-1 drugs and an AI podcast app (Snipd) cited as standout breakouts.
IDEAS WORTH REMEMBERING
5 ideas“Delusional” can mean unusually logical, risk-tolerant, and relentless.
Sam Parr chose Val, describing him as calm yet extreme: an immigrant entrepreneur who has built multiple businesses without raising money, invests in Brooklyn real estate, and keeps an unconventional schedule while raising five kids.
Some “crazy” success stories look boring on the surface.
A speaker described meeting Michael Dell and being struck by how ordinary and steady he seemed despite enormous wealth, including an anecdote where a private credit deal ended with him owning a pro sports team after a borrower defaulted.
Owning a community hub can be a powerful business model if you don’t break trust.
A speaker said buying 60% of Letterboxd came from a casual coffee conversation that turned into an acquisition, and framed social networks as “airports” where owning the gathering place enables many monetization options if the community is kept happy.
Pairing a trusted audience with a product you believe in can create outsized leverage—especially with smart deal structure.
Shaan Puri said his best investment was a minority stake in Shepherd, crediting tailwinds (remote work, profitability pressure driving offshore hiring) and the ability to drive leads from his audience; he also emphasized that deal structure mattered greatly.
In angel investing, time-to-liquidity and “missed shots” can be the real pain points.
Multiple speakers framed angel/venture investing as psychologically hard due to long timelines and low immediate liquidity, with Shaan emphasizing that missing big winners can matter more than small losses and Sam saying he dislikes the patience and lack of involvement.
WORDS WORTH SAVING
5 quotesI think Elon's insane, but I didn't wanna pick him 'cause that's too easy.
— Sam Parr
I think I bought it for a million bucks and it just lost 10 to 20K a month, and it was a small enough number that blended into all my other stuff. I just didn't really notice it.
— Unattributed
Paper don't pay my mortgage, at least not this type of paper.
— Sam Parr
If you think you wanna build a house, try it. It really sucks.
— Unattributed
There is a magic weight loss pill.
— Shaan Puri
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SPEAKERS
Shaan Puri
hostEntrepreneur and investor; co-host of My First Million and founder of Milk Road.
Sam Parr
hostEntrepreneur and investor; co-host of My First Million and founder of The Hustle.
High quality AI-generated summary created from speaker-labeled transcript.
