My First Million – The 2025 Milly Awards!

December 18, 2025

Hosts & Guests:

• Sam Parr
• Shaan Puri
• Steph Smith (recurring guest)

Overview

In the annual "Milly Awards" episode, Sam, Shaan, and Steph reflect on the past year, handing out light-hearted awards across categories like best and worst investment, biggest personal L (loss), coolest moment, and more. They use this time to recap lessons, funny stories, notable guests, and inspirational moments from the year, while showcasing their signature blend of irreverence and real talk about money, business, and life.

Major Segments & Timestamped Highlights

Podcast Reach & Growth

[00:22]

• Sam and Shaan are astounded by the pod’s explosive growth:
  • 90 million total views/downloads in 12 months
  • Almost 2 million subscribers across major platforms
• Sam:

  “That number, 90 million, that’s a lot of view time. A lot of views.”

Best Investment of the Year

(Begins [01:27])

Sam Parr

• "Investment" taken broadly—his move to a furnished apartment in NYC.
• Sold all his cars, owns less, is closer to family and office, feels genuinely happier.
  [02:28]

  “Owning less stuff, moving to the city, being near your family. Working in person in an office, that's actually a pretty big change overall.” – Shaan

Steph Smith

• Not a financial investment: Accutane (acne medication) changed her life after decades of acne, inspired by a MrBeast podcast mention. [04:37]

  “I'm clear. And I think it's like, you know, obviously your mileage may vary. Go talk to a doctor. But I'm just like, this is the best thing ever.” — Steph

Shaan Puri

• Went shopping for stocks as a Christmas present to himself:
  • Spread ~$1.25M across Shopify, Tesla, Eli Lilly, Bitcoin, Coinbase, Google
  • Ended up with a 35% return over the year
    [06:42]

  "I operate on gut and swagger, okay?"

  • Shaan credits Sam for his hunch on Eli Lilly, with Ozempic-like drugs.

Worst Investment of the Year

(Begins [11:16])

Sam Parr

• HubSpot stock, post-acquisition, took a hit after high growth multiples faded.

Steph Smith

• A failed bubble tea franchise (invested during the “peak syrup” era); more soul-crushing, though: attending networking events she knew she’d hate.
  [12:24]

  “All these things that you just like, you know beforehand are going to suck. You're not going to like them, but there's some sliver of you that thinks, like, there might be something good there.” — Steph

Shaan Puri

• Passed on three $10B companies he was uniquely qualified to invest in:

  • Polymarket (prediction markets; founder was a fan, DM’d him)
  • Ki (another prediction market)
  • Whatnot (live e-commerce), after working at Twitch
    [14:41]

  “It was literally the thing I was doing … there's not 100 people on Earth that know that space better than I do … and missed it.” — Shaan

• Reflection on angel investing:

  • Shaan: “You need multi-hundred-x or thousand-x to look like a genius, but you don't really know for a while…” ([18:40])
  • Steph: “My learning from Peak Zerp was I never want to angel invest again, unless it's a company that I want to be involved with actively.” ([18:26])

Biggest Personal L (Loss) of the Year

(Begins [20:19])

Sam Parr

• At a party, mistakenly asked a woman when she was due... she wasn't pregnant.
  • [20:50]

    “I spent 30 seconds looking for an out... then in front of five other people, I just apologized. I said sorry and I walked away. I said, I'm so sorry.” – Sam

Shaan Puri

• Jury duty—a masterclass in failed excuses (tried to lie about needing to care for his baby); ended up being stuck for 3 days, didn’t even get picked.
  • [25:52]

    “I'm the primary caretaker of this baby ... my lie is gone ... I'll be here. Can't wait. I'll be there. And so I just let it pass.” – Shaan

Steph Smith

• Stayed in a job too long, despite being warned by Shaan. Eventually switched to a role at Grok, which is a much better fit.
  • [28:09]

    “I think the epitome of when other people think you should be good at something, and you think therefore you should be good at something and that you should figure it out versus, like, driving full force towards the thing that you love doing.” – Steph

Billy of the Year (Favorite Billionaires/Role Models)

(Begins [29:24])

Sam Parr

• Steve Houghton (real estate & oil billionaire): invited Sam and his wife to a family ski retreat after a pod.
  • Saw firsthand how wealthy people can maintain close family ties.
    [30:43]

  “They say money doesn't buy happiness, but I was very happy being in the 17,000 square foot home with his entire family.” — Sam

Steph Smith

• Sebastian Thrun (godfather of self-driving tech, founder of Udacity & Waymo):
  • Early AI course online (160K students), lifelong learner and builder
    [32:05]

  “He's been early to all of these trends and is just like continuing to build even though he's ... already rich.” – Steph

Shaan Puri

• Jesse Cole (Banana Ball / Savannah Bananas):
  • Built an entertainment empire in minor league baseball (waitlist of 3M, stadiums packed)
    [35:06]

  “That's playing business on such hard mode ... I would never be able to do something like that.”

Coolest Personal Moment

(Begins [39:17])

Sam Parr

• Visiting MrBeast’s “campus” (organized by Shaan) with other successful folks, including Jesse Itzler.
• Jesse was the only one openly marveling at MrBeast’s over-the-top life and calling out the insanity in a fun, grounded way.
  [40:43]

  “Jesse Itzler ... was exact. He was better than he appears on the internet. And he was very inspirational.” — Sam

Shaan Puri

• Learned piano through “misogi” challenge (inspired by Jesse Itzler’s annual rituals).
• Got to play a meaningful piece in Jesse’s home, where “Jesse’s crying, his family is crying.”
  [46:04]

  “It was like the craziest thing. So Jesse’s there, he’s crying ... it was this amazing payoff moment where they actually gave a shit about, like, what I was doing. ... one of the coolest moments of my life, if I’m being perfectly honest.”

Steph Smith

• Split between:
  • Gorilla trekking in Rwanda (with her dad).
  • But biggest: Taking her dad to two World Series games for their beloved Blue Jays.
    [52:21]

    “Totally worth it ... can't really think of a better way.” – Steph

Frame-Breaking Person & Favorite Guest

(Begins [52:49], [58:11])

Frame-Breaking People

• Sam:

  • Will Guidara (ex-Eleven Madison Park, “Unreasonable Hospitality”): Pursuing excellence and high intention in few things.
    [55:05]

    “We are going to go above and beyond and we are going to be excellent ... overfilling my cup, not just in business, but in life.” — Sam

• Steph:

  • Fiona Oakes (ultra-marathoner, vegan, lost kneecap):
    [59:43]

    “…runs a crazy number of miles … she lost her kneecap at 17 … she has multiple world records … because she just loves animals so much.”

• Shaan:

  • Kristen Berman (behavioral scientist): Used wealth not to “upgrade” housing, but to build a community by buying apartments for friends.
    [68:18]

    “Most people I know who make money, they isolate themselves … move into more private communities … a pocket of loneliness … she bought units for a micro-community of friends.”

Favorite Guest

• Sam: Sean Frank (Ridge Wallet CEO), “direct, blunt, wholesome.”
• Steph: John Morgan (Morgan & Morgan, “For the People”)—unexpectedly inspiring PI lawyer, master of quips and simple business wisdom.
  [62:24]

  “I don’t hunt deer, I hunt money.”

• Shaan: Nick Mowbray (Zuru Toys, self-made New Zealand billionaire with wild side quests and “insane agency”).
  [72:09]

  “…the closest person to Elon Musk that I’ve ever met…”

Biggest Change for Next Year

(Begins [75:34])

• Shaan: Social media apps deleted, will “trade” mindless scrolling for reading great books (“Luka Doncic trade”).
• Sam: Going all-in on content (Instagram, YouTube studio, writing).
  • Personal change: Working out done by 7 am (“I hate getting up early, but I love having gotten up early.”)
• Steph: Possibly trying for kids—discusses parental purpose, meaning, and (as a woman) anxieties about the process. [81:20]

  “Especially when you’re a woman, you have to … actually, you know, grow the kid ... It’s a little daunting, but I love hearing from both men and women, like the best parts of having kids.”

Meme/Tweet of the Year

(Begins [87:30])

• Steph: “May I meet you?”—the Bill Ackman meme, and the absurdity of men giving dating advice on Twitter.
• Shaan:
  • Joke:

    “A reminder that tapping your credit card is a spiritually passive and feminine behavior … men should … thrust into the chip reader.” ([91:12])

  • Wholesome:

    “Real success is how many people thank you for theirs.” — Jay Yang ([92:34])

• Sam: Loves the cinematic podcast content trend—e.g., YouTube/Instagram hits with beautiful, cinematic settings.

Best New Habit / Life Hack

• Steph: Running—ran two marathons in 14–16 months, from scratch to sub-8-minute miles ([98:36]).
• Sam: Early morning workouts (“No loser wakes up at 5am to work out” ([80:04])).
• Shaan: Learning piano (see Coolest Moment).

Notable Quotes & Moments

• On Angel Investing:

  “You need a multi-hundred-x or thousand-x type of return … and then you look like a genius, but you don’t really know for a while, to be honest.” — Shaan ([18:40])

• On Life After Kids:

  “Whatever I thought life was before this was just … pregame material for the real game.” — Shaan ([82:30])
  “I was, like, when I got married, I felt like, I’ll kill someone to protect you. And then when I had a kid, it was like, I will die for you.” — Sam ([83:31])

• Frame-breaking Philosophy:

  “Most people I know who make money, they isolate themselves … and they basically, like, create a pocket of loneliness … she bought units for a micro-community of friends.” — Shaan ([68:18])

• On Excellence:

  “Excellence is never an accident. It’s always the result of high intentions, sincere effort, and intelligent execution.” — Aristotle, cited by Sam ([53:55])

• On Social Media:

  “I operate on gut and swagger, okay?” — Shaan ([07:46])

Memorable Table of “Milly Awards” Winners

| Category | Sam Parr | Shaan Puri | Steph Smith | |-------------------------------|-------------------------------------------|--------------------------------------------------------------------|--------------------------------------| | Best Investment | NYC apartment/lifestyle | Stock spree (35% return, “Christmas shopping”) | Accutane (acne treatment) | | Worst Investment | HubSpot shares post-exit | Missed $10B company angel deals | Networking events, Bubble tea co. | | Biggest Personal L | Pregnancy question disaster | 3-day failed jury duty excuses | Stayed too long in wrong job | | Coolest Moment | MrBeast/Itzler weekend | Piano recital at Jesse Itzler’s home (everyone cried!) | Gorilla trek/Blue Jays WS with dad | | Billy of the Year | Steve Houghton (real estate, oil billion) | Jesse Cole (Savannah Bananas) | Sebastian Thrun (Waymo/Udacity) | | Frame-Breaking Person | Will Guidara (ex-Eleven Madison Park) | Kristen Berman (communal apartment living) | Fiona Oakes (kneecapless marathoner) | | Favorite Guest | Sean Frank (Ridge Wallet CEO) | Nick Mowbray (Zuru Toys) | John Morgan (PI lawyer) | | Biggest Change for 2026 | New content grind, early workouts | Quit social media, read more books | Possibly start a family | | Best Habit/Life Hack | Early workouts | Piano practice | Running | | Meme/Tweet of the Year | Cinematic podcasts/IG stories | “You could just do things”—Jay Yang; CC tap joke ([91:12]) | “May I meet you?” meme |

Closing Thoughts

The 2025 Milly Awards episode delivered exactly what makes MFM a cult favorite: humblebrags, failed bets, actionable lessons, deep life reflection, and plenty of laughs about the business of making, losing, and enjoying one’s first (or tenth) million. The hosts’ candor about money and meaning keeps things relatable and entertaining—another banger to close the year.

Key Takeaways

• Real wealth isn’t just about money—it’s about experiences, relationships, and doing things that matter to you personally.
• Angel investing is a mix of luck, deal flow, and a lot of losers for a handful of huge winners.
• Personal growth sometimes comes from unexpected places (new hobbies, therapy, community, or just letting go).
• Being intentional about your environment and habits—whether deleting apps, running a marathon, or building community—leads to richer, more memorable years.
• Meaningful life changes (kids, career switches, deeper friendships) almost always involve some discomfort and leap of faith.

Listen if you want:

• Honest talk about money and happiness
• Inspiration for taking risks and changing habits
• To laugh—and maybe cringe—at relatable personal fails
• The best “billionaire of the year” and biggest business “misses”
• A thoughtful, funny year-end reset for entrepreneurs

[End of Summary]