Podcast Summary: My First Million — “I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson”
Date: November 7, 2025
Hosts: Sam Parr & Shaan Puri
Guest: Andrew Wilkinson (Co-founder of Tiny, founder of Metalab)
Episode Overview
In this episode, Sam and Shaan welcome Andrew Wilkinson to break down, tier-list style, the best and worst businesses you could start before 2026. Drawing on Andrew’s ownership of 30+ businesses (agency, SaaS, restaurants, private equity, and more), they discuss the realities of different business models—including lifestyle, median success case, scalability, risk, and defensibility. The episode is fast-paced and candid, with Andrew offering hard-won advice, specific anecdotes, and reflections about public perception, internet criticism, and the “courage to be disliked.”
Key Discussion Points & Insights
1. Tier List Methodology (03:00–04:00)
- Goal: Evaluate business models by median successful outcome, not by rare outlier successes.
- Criteria: Median outcome, lifestyle/ownership risk, defensibility, scalability, and likelihood of success—not just upside.
- Structure: S-A-B-C-D-E-F, with “S” as “God Tier.”
2. Business Model Rankings & Deep Dives
A. Multi-Level Marketing (MLM): F Tier
[03:33–04:25]
- Andrew: “I mean, I would rank an MLM as an F. It’s a fundamentally unsustainable business that breaks. The problem with an MLM is it's reliant on recruiting other people… it makes money by finding the next sucker.”
- Most people lose money; only the founders/early joiners win (often unethically).
- Odds of jail: “50/50 you go to jail.”
—Andrew [04:25]
B. Freelance/Owner-Operator: D Tier
[04:43–05:10]
- Andrew: “It’s a living… nothing wrong with freelancing…but fundamentally it's an owner operator model. It doesn't really scale unless you scale it.”
- Good for self-employment, not wealth accumulation.
C. Agencies: C Tier (Tentative)
[05:41–07:30]
- Andrew: “I don't know that I would still rank it very highly... You’re either making a ton of money or you’re about to go out of business.”
- Feast or famine with big clients; scalability and reputation are hard to replicate.
- Example: Metalab’s outsized success was “lightning in a bottle”—other agencies didn’t hit.
- Memorable quote: “The worst thing that happens…Walmart…wants to give you 10 million…you hire 30 people…new PM takes over... cuts your budget... you have to lay off.” [06:31]
D. SaaS: B Tier (with caveats)
[09:41–13:32]
- Andrew: “It depends on the type of SaaS... A ChatGPT thin wrapper... bad SaaS business. But, the dominant player in funeral home management, all the funeral homes use it…that’s an incredible SaaS business.”
- Recurring, high margin, but rising competition from AI (LLMs) compresses margins.
- Success Story: Serato (DJ software): Integrated with hardware, dominant, “toll road to becoming a DJ.” $45M revenue, $15M EBITDA.
- Memorable moment: The DJ anecdote—status, lifestyle, defensibility [13:36–14:44].
E. Restaurants: E Tier
[14:55–16:38]
- Andrew: “Restaurant is a…great passion if you love food. Labor of love…one of the hardest businesses.”
- Low margins (10% is “winning”), physically and emotionally draining, relentless day-to-day effort needed.
- Humility: “When I meet somebody and they say I have a successful restaurant, I want to, like, Wayne’s World, get down on my knees and say, I’m not worthy.” [14:55]
- Sam: “Pretty much a crime [MLM] is the only thing that's been worse so far.” [16:38]
F. Marketplaces:
- Airbnb-level marketplace: A Tier
[17:30–19:01]- Winning a market = “lightning in a bottle,” strong defensibility and upside.
- Andrew: “I like a business where it becomes a verb…Airbnb, that’s probably an A.”
- General marketplaces: C Tier
- Difficult to get both sides (supply/demand); most fail.
- Controversial pick: “That’s the one I would disagree with you with.” —Shaan [18:32]
G. Airbnb Hosting / Short-Term Rentals: D Tier
[20:02–20:36]
- Fragile to regulatory changes and local ordinances, which can “kill” the margin overnight.
- Real examples from Andrew (Vancouver) and Shaan (San Francisco).
H. Content Creator / Influencer: D Tier
[21:32–23:29]
- Big wins possible (Huberman as example), but “if you don’t show up and bring the fire…your business goes to zero.”
- Defensible brand, but hard to scale or automate—“bit of a prison for some people.”
I. Real Estate (Ownership/Development): C Tier
[24:03–26:40]
- Pros: Predictable, great for long-term wealth (“no brainer” for some).
- Cons: Low ceiling, illiquid, doesn’t scale through innovation—“good way to make your kids really, really wealthy and then they'll buy an F1 team and lose it all.”
J. Asset Management & Investing:
- Asset management business (hedge fund, VC, PE—but not “Buffett-style”): B Tier
- Consistent fees, but huge swings and client redemption risk.
- Andrew: “Guaranteed to become a deca-millionaire…almost no matter what.”
- Permanent capital model (Buffett/Ackman): S Tier
- Fees AND permanent capital = “God Tier.” Most lucrative, defensible, and scalable.
- “That’s S. And Buffett is S.” [27:24]
- Only risk: public scrutiny.
- Astonishing moment: “Bill Ackman’s firm is 50 employees, $15B AUM, making $200M plus a year in cash flow just off the fees.” [30:04]
- Angel investing: E Tier (too risky, illiquid, hobby for most).
- "I have $30 million or something tied up in angel investments. Completely illiquid... I'd much rather own... stocks and real estate." —Andrew [39:03]
K. Buy a Sweaty/Local “Boring” Business: C Tier
[40:02–41:31]
- Wise to “skip the line” and buy a working business versus starting one, but often you’re buying a job rather than a scalable business.
- Andrew: “If I just bought businesses and improved them, I’d be much farther ahead than I am today.”
L. Local Service Businesses: C Tier
[36:48]
- Good if you’re an insider/operator; hard for outsiders to break in.
- Can dominate if you’re great at hiring and marketing, but operationally challenging.
Notable Quotes & Memorable Moments
| Timestamp | Speaker | Quote / Moment | |---------------|-------------|----------------------| | 04:25 | Andrew | “If you are willing to go to jail…you can make a lot of money, but I mean, like 50/50 odds you go to jail.” | | 06:31 | Andrew | "Worst thing…Walmart gives you $10 million of work…you hire 30 people…PM changes…budget cut…left with 30 people you have to lay off." | | 09:41 | Andrew | “SaaS…it depends…if you become standard in a niche, it's incredibly defensible.” | | 14:55 | Andrew | “Restaurant is a…great passion if you love food…one of the hardest businesses…To be successful, I want to, like…say, I'm not worthy.” | | 20:02 | Andrew | “I Airbnb’ed it... making a fortune... city of Vancouver changes the regulations. Boom. There goes my margin, there goes my business.” | | 23:29 | Andrew | “If Huberman was doing the same sort of podcast, but…reviewing candy…affiliate margins not that good…” (niche and trust factor matters) | | 25:39 | Andrew | “I don't like anything with a ceiling. You can't innovate to make more money.” (on real estate) | | 27:24 | Andrew | “Bill [Ackman] as S and Buffett as S…and other asset managers lower. They have permanent capital. That's the real distinction.” | | 41:31 | Andrew | “If I had just…bought businesses and just improved them, I think I'd be much farther ahead than I am today.” | | 46:21 | Andrew | “We have 65 million of ARR…over $40 million of EBITDA…over 300 million in revenue across 30 businesses…and all the businesses in the fund are profitable as well. If that’s failing, sign me up.” | | 54:25 | Andrew | “You do not want to be liked by everybody. I think that's a great signal that you're doing life wrong…you have to have the courage to be disliked.” |
Internet Criticism & “The Courage to Be Disliked” [46:21–60:00]
- Stock price as a bad scoreboard: Many judge Tiny’s success just by its public chart (“down from IPO”), missing the context of steady value creation.
- Andrew on criticism: “I really empathize with people…there’s this dirty, horrible part of humanity, myself included, that loves when someone who’s on an upswing falls.” [48:28]
- Confusion about Tiny's story: Multiple businesses merged, distorted chart makes success hard to recognize.
- Vulnerability/honesty: Andrew has “ADHD” and struggles not to correct misconceptions, but tries to focus on doing the work, not defending himself.
- Key lesson: Seeking recognition is a trap; “You have to have the courage to be disliked.” [54:25]
- Identity & boxes: Andrew and Shaan discuss how success often pigeonholes you, and society punishes “leaving your lane”—but in reality, reinvention is key to happiness.
Miscellaneous Highlights
- Inputs vs. Outputs: Shaan counsels to “be jealous of the inputs, not outputs”—love the day-to-day of your heroes, not just their results. [71:32–74:09]
- Business “Formulas” vs. Serendipity: Andrew’s best opportunities came from following curiosities and randomness, not predetermined formulas. [67:11–70:56]
- Content creation vs. craftsmanship: Shaan’s new project will focus on “craftsman” output, not the ephemeral cycle of podcasting/social media. [78:20–78:40]
Timestamps for Major Segments
- 00:00–04:00: Tier list structure & methodology
- 03:33–04:25: MLMs (F tier)
- 04:43–07:30: Freelancing & Agencies
- 09:41–13:32: SaaS (with Serato example)
- 14:55–16:38: Restaurants
- 17:30–19:01: Marketplaces
- 20:02–20:36: Airbnb/Short-term rentals
- 21:32–23:29: Content creation
- 24:03–26:40: Real estate
- 27:10–32:10: Asset management & investing models
- 36:48–37:45: Local service businesses
- 39:03–41:31: Angel investing & “boring business” acquisition
- 46:21–54:25: Internet criticism, Tiny’s story, courage to be disliked
- 54:25–60:01: Identity, labels, and creativity
- 71:32–78:40: Jealousy, fulfillment, “inputs not outputs,” closing thoughts
Takeaway Lessons
- Median-case matters: Don’t build a business model for outlier successes; pick one with a stable, defensible, and pleasant median outcome.
- Build for lifestyle: Passive/recurring revenue and control matter more than chasing status or risky high-upside swings.
- Defensibility is everything: Standardization, becoming a “verb,” and embedding into customer workflows are major levers.
- Public opinion ≠ success: Social media troll mobs and public market charts rarely tell the full story—focus on long-term compounding, not headlines.
- You can’t live for approval: Reframe disapproval as a signal you’re uniquely you—a requirement for real happiness and innovation.
Further Reading/Follow Andrew
- Andrew Wilkinson’s newsletter: never-enough.com
- Tiny: Public investment holding company, multiple operating businesses
This episode offers rare candor, uncomfortable truths, and practical wisdom for aspiring entrepreneurs and investors working through today’s noisy, fast-changing business landscape.