My First MillionNov 7, 20251h 19m74.8K views

I Own 38 Businesses. Here's What Actually Makes Money.

Name: I Own 38 Businesses. Here's What Actually Makes Money.
Uploaded: 2025-11-07
Duration: 1 h 18 min 33 s
Description: Andrew Wilkinson compares agencies, SaaS, restaurants, marketplaces, short-term rentals, real estate, fund management, local services, investing, and sweaty startups. The description says he built 38 companies, lost $10M, created Tiny from $4M, and ended with a $300M portfolio, while arguing that buying companies can beat building them.

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Synopsis

Andrew Wilkinson compares agencies, SaaS, restaurants, marketplaces, short-term rentals, real estate, fund management, local services, investing, and sweaty startups. The description says he built 38 companies, lost $10M, created Tiny from $4M, and ended with a $300M portfolio, while arguing that buying companies can beat building them.

Ideas in this episode

Local services roll-up
Apply the model-selection lens to choose small software or productized-service bets around a website engine, a mobile-services platform, or a builder business instead of capital-heavy acquisitions.
Small business acquisition (no experience required)
Andrew Wilkinson's model-selection lens favors small software or productized-service bets in familiar B2B niches over capital-heavy acquisitions, especially when the operator can compare SaaS, agencies, local services, and marketplaces side by side.
B2B bookkeeping / accounting SaaS
Andrew Wilkinson's model-selection lens favors small software or productized-service bets in familiar B2B niches over capital-heavy acquisitions, especially when the operator can compare SaaS, agencies, local services, and marketplaces side by side.