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

About this video

Andrew Wilkinson joins Sam and Shaan to rank different business models on a tier list, evaluating each by median success outcomes, lifestyle factors, upside potential, and likelihood of success. They debate the merits of various business types—from MLMs (F-tier) to agency work, SaaS, marketplaces, restaurants, real estate, and investment management—with Wilkinson sharing lessons from his experience building Metalab, starting Tiny, and managing a portfolio of businesses. The conversation also addresses criticism of Tiny’s stock performance and Wilkinson’s philosophy on embracing a non-linear, multifaceted identity rather than staying confined to a single lane.

Key takeaways

• Andrew argues the best businesses to start are those with high median success outcomes, good lifestyle factors, meaningful upside, and reasonable probability of success—not just outlier scenarios
• Agencies can generate substantial profits (Andrew claims Metalab generated hundreds of millions in lifetime profits) but are ’lumpy’ and risky due to client dependency and feast-or-famine dynamics, making them a C-tier business
• Investment management with permanent capital (like Buffett or Bill Ackman’s Persing Square) is S-tier because fees are guaranteed regardless of performance, while hedge funds without permanent capital rank lower due to redemption risk
• SaaS is B-tier overall, but vertical niches with high switching costs (like Serato’s DJ software deeply integrated with hardware) can be exceptional; general SaaS is increasingly competitive as AI and LLMs lower barriers to entry
• Marketplaces are difficult and highly competitive; Airbnb as a concept is A-tier, but owning Airbnbs is D-tier due to regulatory risk and margin compression
• Restaurants are E-tier (worse than F-tier MLMs for most people): brutal low margins (10% is success), constant operator presence required, and high failure rates make them poor wealth-building vehicles
• Real estate is C-tier without a specific edge; it’s predictable but has a ceiling on returns, is illiquid despite creating wealth across generations, and lacks the innovation upside of digital businesses
• Andrew transitioned from starting many businesses to acquiring and improving existing profitable businesses in 2013, which proved more effective; Tiny’s $4–5M seed capital has compounded into a 300M+ revenue portfolio of 30 profitable businesses
• Criticism of Tiny’s stock decline since 2021 is partially fair but lacks context: the stock launched during peak mania at 1.2B market cap (not Wilkinson’s choice) and Tiny has continued compounding earnings at 25% and generating substantial EBITDA
• Andrew advocates for rejecting the pressure to fit into a single identity or ’lane’; embracing inconsistency (tech investor + restaurant owner + real estate developer) is healthier and more authentic than forcing yourself into a clean, marketable box

Episode details: published November 7, 2025 · 77K views · 1:18:33 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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