I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson

What It Covers

Andrew Wilkinson ranks business models from MLMs to investment funds, sharing insights from building MetaLab to hundreds of millions in profit and managing Tiny's portfolio of 30 companies generating over $300 million revenue.

Key Questions Answered

• •Agency Economics: MetaLab generated hundreds of millions in profit but ranks only C-tier due to feast-or-famine client cycles. Winning a $10 million Walmart contract means hiring 30 people, then facing layoffs when budgets shift unexpectedly under new project managers.
• •SaaS with Hardware Moats: Serato DJ software generates $45 million revenue and $15 million EBITDA by deeply integrating with Pioneer hardware. DJs invest $5,000 in equipment and won't switch easily, while manufacturers resist integrating with new competitors, creating defensible competitive advantages.
• •Permanent Capital Advantage: Bill Ackman's Pershing Square with 50 employees manages $15-20 billion, earning 1.5% fees ($200+ million annually) plus 20% performance carry. Permanent capital structure prevents investor withdrawals during downturns, unlike traditional hedge funds forced to sell positions.
• •Real Estate Ceiling Problem: Real estate investing ranks C-tier because rent has natural ceilings based on market rates. Unlike digital businesses where profits can fuel exponential growth through innovation, real estate requires massive capital expenditures to scale, creating illiquidity despite impressive paper valuations.
• •Courage to Be Disliked: Seeking universal approval traps entrepreneurs in narrow boxes. Jesse Itzler successfully reinvented himself from rapper to jingle writer to private jet company founder to coconut water investor, demonstrating that unlabelable careers attract more interesting opportunities than rigid specialization.