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.

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Show Notes:

(0:00) Intro

(3:06) MLM

(4:28) Freelancer

(5:07) Agency

(9:33) SaaS

(14:48) Restaurant

(17:03) Marketplace

(19:43) Short Term Rentals

(20:52) Content Creator

(23:06) Real Estate

(26:16) Fund Management

(35:21) Local Services

(36:36) Investing

(38:12) Sweaty Startup

(43:15) Tiny stock performance

(52:20) The courage to be disliked

(1:10:21) Inputs v outputs

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Links:

• Tiny - https://tiny.com/

• Never Enough - https://www.neverenough.com/

• Serato - https://serato.com/

• Rekordbox - https://rekordbox.com

• Pershing Square Holdings - https://pershingsquareholdings.com/

• Invest Like The Best - https://www.youtube.com/@ILTB_Podcast

• The Courage To Be Disliked - https://tinyurl.com/5fk3sa79

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Check Out Shaan's Stuff:

• Shaan's weekly email - https://www.shaanpuri.com

• Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents.

• 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

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Check Out Sam's Stuff:

• Hampton - https://www.joinhampton.com/

• Ideation Bootcamp - https://www.ideationbootcamp.co/

• Copy That - https://copythat.com

• Hampton Wealth Survey - https://joinhampton.com/wealth

• Sam’s List - http://samslist.co/

My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano //

Jonathan McCrea

The AI-powered Podcast Player