My First Million Ep. #141 - The 2020 MFM Award Show (with Andrew Wilkinson)
Date: December 30, 2020
Host(s): Sam Parr, Shaan Puri
Guest: Andrew Wilkinson
Main Theme:
A fun, fast-paced “Year in Review” episode where Sam, Shaan, and Andrew break down business and investing trends for 2020, hand out tongue-in-cheek awards (“the Millies”), revisit favorite moments, share personal and business insights, and dish out predictions for 2021.
Episode Breakdown
1. Opening / Setting the Scene
- The guys celebrate the end of 2020 with an “award show” format called “the Millies.”
- Structure: Four sections — Awards, Predictions/Investments, Ideas, and Personal Life.
- Tone: Playful, candid, self-aware (“If you’re thinking this podcast is better than usual, that’s because we actually prepared for this one!” – Shaan, 00:21).
2. Millies Awards Section
A. Billy of the Year: Top Billionaire Stories [02:49]
Each host picks their “Billy of the Year”—their favorite billionaire story.
- Sam: Chuck Feeney (duty-free magnate who gave away entire fortune)
- “He made like 10 or 20 billion … officially has given away his entire fortune other than a million dollars and a San Francisco apartment.” (Sam, 02:52)
- Andrew: Mark Leonard (founder, Constellation Software)
- “Focusing on super boring verticals with low competition and high switching costs … compounding this business for 25 years … worth $1.9 billion and walks around with nobody knowing.” (Andrew, 03:19)
- Honorable Mentions:
- Dan Gilbert (Rocket Mortgage), Mackenzie Scott (philanthropy), Michael Saylor (bold bitcoin bet), Elon Musk.
- Winner (Shaan's pick): Eric Yuan (Zoom founder): “Zoom held the world together in 2020 … connect schools, families, businesses.” (Shaan, 07:21)
B. Breakout Company of 2020 [08:22]
- Andrew: Shopify – “the obvious winner of the pandemic” (08:39).
- Sam: Hoppin – Virtual events “launched in 2020, raised a lot of money, hired 250 people in six months” (Sam, 09:05).
- Shaan: Moderna – “Developed the vaccine in kind of record time… stock up 10x this year alone.” (Shaan, 09:27)
- Discussion around second/third order effects: Rogue Fitness as a COVID winner (Sam, 12:21).
C. Under-the-Radar Company [13:03]
- Sam: Calendly – Bootstrapped “worth north of a billion dollars” (13:20).
- Shaan: Pipe – “They turned SaaS contracts into a liquid asset where there’s a market… could be humongous.” (Shaan, 15:01)
- Andrew: Carta – “Super boring product … but could become a network or marketplace for private company stock.” (Andrew, 16:14)
- Fascinating discussion of how Carta could disrupt private market liquidity.
D. Favorite Non-Family Person of 2020 [19:08]
- Sam: Jack Smith and late Felix Dennis (“How to Get Rich”)
- Andrew: His business partner Chris, then—“cheesy” but—Sam & Shaan for idea-sparking. (21:01)
- Shaan: His personal trainer, Ja (“Trainers are about people—the right person makes all the difference.” 21:45)
- Candid chat on health, progress tracking, and mindset shifts.
E. Favorite Tool of 2020 [26:22]
- Shaan: Pinata Farm (meme creator): “It’s the shit you see on Reddit, but easy to make” (26:41).
- Sam: YouTube Premium & YouTube TV (“If I can have only Spotify or YouTube Premium … YouTube Premium, easy.” 27:30)
- Andrew: Readwise (resurfaces Kindle highlights); HuffDuffer (pulls audio from videos into your personal podcast feed)
3. Predictions & Investments
A. Highest-Returning Financial Investment [29:37]
- Andrew: Buying back, then IPO-ing his old Shopify ecosystem SaaS company (“Turned $10M into $220M”). (29:37)
- Sam: Airbnb stock (acquired at low valuation during COVID, big IPO pop, 30:21).
- Shaan: Amazon stock, Bitcoin (massive 2020 run-up), Zoom.
B. Best Bet for 2021 [39:55]
- Shaan: Bitcoin (“I’m betting on a five to seven-year horizon … strongest network effect I’ve seen in years.” 39:53)
- Andrew: “Sell pickaxes to gold miners—would rather own Coinbase than Bitcoin … Stripe—just take a percent on all online commerce.” (40:06)
- Sam: Index funds only (“I’m boring.” 42:00)
C. What Did You Get Wrong / Lose Money On? [42:08]
- Andrew: Gambled (and lost) millions on S&P 500 puts at the bottom, after making a successful initial trade (43:06).
- Sam: Overestimating Supercast’s breakout year.
- Shaan: Sold Tesla stock too soon, missed out on a 30x return. (46:49)
- “I was spooked by all the TeslaQ people on Twitter who were convinced Tesla was Enron.” (47:26)
D. Who Would You Invest In (Person) for 10 Years? [48:51]
- Shaan: Vishal Harpalani (young hedge-fund builder, “wannabe George Soros”)
- Sam: Ramon Van Meer
- Andrew: Brent Beshore (“Low-risk, old-school business buyer. Would bet on him for 50 years.” 50:12)
E. Wildest Prediction [51:04]
- Sam: SF will rebound as tech capital; paying for porn subscriptions will become normalized.
- Andrew: “No one’s going to give a shit about COVID in a year.” (52:57)
- Shaan: Agrees, travel will spring back.
4. Ideas Section
A. Best Podcast Idea of 2020 [54:44]
- Sam: Cloud kitchens/ghost kitchens as predicted by “Stu,” plus collectible sites (PSA acquisition).
- Andrew: Always-on AirPods / passive walkie-talkie communication.
- Shaan: Local news newsletters as a viable, high-utility, potentially profitable “labor of love” business.
- “If you did this in every city you could get to a $1-2M/year company, but it’s really satisfying.” (Andrew, 57:04)
B. Favorite & Least Favorite Guests/Ideas [59:04, 60:25]
- Guests: Ryan Begelman (Andrew’s pick), Daniel Gross (Shaan’s), Lance Armstrong for anecdotal reasons (Sam).
- Least Favorite Idea: Dog VR (Craig Clemons, “Oculus for dogs”), digital art/NFTs (“stupidest fucking idea I’ve ever heard,” Andrew, 61:17), Thrasio’s FBA rollup model.
- [Bet declared on Beeple/NFT art value over 10 years. 62:52]
C. Startup Trends They Disagree With [79:09]
- Sam & Andrew: Fast’s one-click checkout is a “feature, not a product” — Shopify Pay will win.
- Andrew: Lambda School won’t be a winner-take-all (“nothing unique about ISAs, everyone rolls it out”).
- Shaan: Remote-first startups are overrated: “Speed, agility, and creativity come from close, in-person work.” (82:13)
- Andrew strongly disagrees, praising global talent pools (“been running remote for 15 years and it works,” 83:10).
5. Personal Life & Reflection
- Best Book:
- Sam: Sons of Wichita (Koch brothers)
- Andrew: Lights Out (GE’s fall)
- Shaan: PayPal Wars
- Best/Worst Habit:
- Andrew: Nose breathing from Breath by James Nestor; drinks too much fizzy water (PFAS scare).
- Shaan: Regular workouts.
- Sam: Swaps Diet Coke for Topo Chico sparkling water.
- Best/Worst Purchase Under & Over $100:
- Shaan: Bulk clothes from 32 Degrees and Bomba socks; Amazon foot massager for wife.
- Sam: Power Blocks adjustable dumbbells; 85” TV.
- Andrew: Leica Q2 camera; MagSafe iPhone wallet.
Wife/Relationship Hack [99:13]
- Sam: Joint meetings with an accountant.
- Andrew: Automated reminders via Apple Shortcuts to reduce logistics fights.
- Shaan: Creates “happy hour”—20 minutes/day focused on spouse’s happiness.
Resolution & Year-End Reflection [101:28]
- Andrew: “No calendar” rule for meetings in 2021.
- Shaan: “Design Your Life” – self-reflection with scores & “version release notes,” not tied to new year (103:13).
- Sam: Runs 200m in 22 seconds—“very, very good for a 30-year-old not regularly athletic.” (104:15)
6. Notable Quotes & Memorable Moments
-
“He [Eric Yuan] made Zoom, and Zoom held the world together during 2020.”
— Shaan, [07:17] -
“Dan Gilbert—his net worth jumped by $36 billion in one day.”
— Andrew, [08:03] -
“If the oven burns hot enough, you can put anything in there, but you can always out-eat any workout.”
— Sam, [24:50] -
“All these other people are in my head—when I’m in the sauna, I’m walking … you guys spark ideas.”
— Andrew, [21:01] -
“COVID’s big lesson: you can adjust to almost anything.”
— Andrew, [92:48] -
“Dude, go eat a pear. Pears are amazing.”
— Shaan, [92:26] (spontaneous fruit tangent becomes an episode meme) -
“If you put raisins with turds, you’ve still got turds.”
— Andrew (on FBA business rollups), [64:11] -
"There's levels to this."
— Shaan, [97:51] (on personal growth)
7. Timestamps: Key Segments
- 00:21 – Award show setup
- 02:49 – Billy of the Year
- 08:22 – Breakout Company of 2020
- 13:03 – Under the Radar Company
- 19:08 – Most Impactful Person, Non-family
- 26:22 – Favorite Tool of 2020
- 29:37 – Best Financial Investment
- 42:08 – Biggest Miss/Loser/Bad Call
- 51:04 – Wildest Future Prediction
- 54:44 – Best Podcast Idea of the Year
- 59:04 – Favorite Guest
- 61:13 – Dumbest Ideas (“Dog VR”, digital art)
- 82:13 – Disagreement: remote work for startups
- 99:13 – Relationship hacks
- 101:28 – Resolution for 2021
Final Thoughts
- Rich in candid takes, practical ideas, witty banter, and personal transparency.
- The trio’s chemistry shines, blending humility (“I totally missed that”) with sharp business acumen and healthy self-deprecation.
- “2020 sucked”—a common refrain, but the group finds gratitude, opportunity, and optimism throughout the episode.
- “The Millies” format is lighthearted but offers real insight into winning businesses, overlooked moneymakers, and the value of long-term thinking.
If you’re looking for:
- Business trends and ideas you can act on
- Candid reflections and life hacks from serious builders
- A playbook to learn from both wins and misses
—this is the definitive “year in review” to inspire and entertain.
For more:
- Tweet feedback to @ShaanVP @thesamparr @awilkinson
- Links and references: [see podcast show notes]
TV Show of the Year:
- Cobra Kai (“The ultimate mood booster. It’s amazing.” - Andrew, 104:46)