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#815November 7, 20251:20:11

I Ranked the Best & WORST Businesses to Start Before 2026 | Andr…

About This Episode

Shaan Puri and Andrew Wilkinson rank various business models—from agencies to permanent capital funds—based on their potential for scale, profitability, and lifestyle. Andrew reflects on his journey with Tiny, addressing the volatility of public markets and the importance of professional evolution beyond traditional industry labels. The episode concludes with a deep dive into the psychological freedom found in the courage to be disliked when pursuing authentic goals.

Episode Description

Which business model should you start? Get Andrew's cheat sheet with his full ranking and real profit margins here: https://clickhubspot.com/dge Episode 762: What’s the best business to start in 2026? Agencies, SaaS, Restaurants, Real Estate, Marketplaces. Angel Investing; Andrew Wilkinson has played every game. He built 38 companies, lost $10 million, and still ended up with a $300 million portfolio. This week, @shaanpuri spoke with him about: the best and worst business models to win in 2026 starting Tiny with just $4M (now $250M) the truth behind the Twitter hate on Tiny’s stock why buying companies beats building them His is not a redemption story. It is the unapologetic reality of building, failing, and getting back up.

Show Notes

Check Out Shaan's Stuff

  • Shaan's weekly email
  • Visit
  • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies!
  • Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC

Key Takeaways

1

Prioritize business models with high switching costs and toll road positions, such as vertical software that integrates with specialized hardware to create a defensible niche.

2

Build or invest in structures with permanent capital to avoid the risks of forced liquidations during market volatility, which allows for more aggressive and consistent long-term compounding.

3

Use jealousy of inputs rather than outputs as a compass for career decisions, ensuring you genuinely enjoy the daily tasks required to reach a specific success milestone.

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Quick Stats

Duration1:20:11
Guests1
Ideas Discussed0
Topics4