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My First MillionRanking The Best And Worst Businesses To Start w/ Billionaire Investor Andrew Wilkinson (#386)
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At a glance
WHAT IT’S REALLY ABOUT
Andrew Wilkinson Ranks Businesses By Difficulty and Dissects Investor Fraud and Folly
- Wilkinson walks through his portfolio from hardest businesses (bakery, restaurants, cat furniture e-commerce) to medium (agencies) to easiest (We Work Remotely), explaining why physical goods and large staffs make businesses brutal.
- He shares costly lessons including selling Pixel Union for $7 million before buying it back and taking it public, plus losing $10 million on Flow against Asana.
- He describes his new venture Tenzing, a modern investment bank for bootstrapped founders, and floats an idea for a service that targets one person's attention across the internet.
- The hosts and Wilkinson discuss fraud and hype-driven public markets, including Canadian stock promotions, Nikola, Bird and the FTX collapse.
- They debate venture capital's fee incentives and Wilkinson's non-binary term sheet, with Shaan Puri arguing you can't outsource conviction to big-name investors.
IDEAS WORTH REMEMBERING
5 ideasPhysical, labor-heavy businesses are the hardest to run
Wilkinson says brick-and-mortar and goods-moving businesses with many employees, such as his bakery and deli with 40 to 50 staff, are far harder than internet businesses, while his e-commerce cat furniture venture earned only 2 to 3% margins versus 30 to 50% in agencies.
Failed ventures teach you what a good one looks like
Wilkinson says his failed pizza restaurant showed him what a badly run restaurant looks like, so he recognized a stable, long-running bakery and deli with a great general manager as a good buy.
Operating experience makes for better investing
Wilkinson contrasts operator investors with spreadsheet investors who assume margins can simply be raised 20%, not realizing that requires convincing 100 people to change.
Don't sell great, fast-growing businesses cheaply
Wilkinson sold Pixel Union for $7 million at about a 14x multiple while it was growing 50% a year, then bought it back for $26 million and later took it public at a $260 million valuation.
Recurring SaaS revenue is stickier than agency work
Wilkinson says agencies face feast or famine and supply-demand balancing, while a sticky SaaS business is rarely ripped out, and he prefers 10,000 people paying a little over 100 paying a lot.
WORDS WORTH SAVING
4 quotesI always think it's better to have 10,000 people paying you a small amount of money than 100 people paying you a lot of money.
— Andrew Wilkinson
I will often do the wrong business before I find the right business.
— Andrew Wilkinson
You can't outsource your conviction.
— Shaan Puri
you're fighting an army that has unlimited budget. It's like Fiji fighting the United States, right?
— Andrew Wilkinson
High quality AI-generated summary created from speaker-labeled transcript.