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

My First Million

Hubspot

Entrepreneurship, Investing, Business

4.8 • 2.7K Ratings

🗓️ 7 November 2025

⏱️ 80 minutes

🔗️ Recording | iTunes | RSS

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Summary

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: (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 — 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 — 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 — 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 //

Transcript

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0:00.0	We have 65 million of ARR. We do over $40 million of EBITA. We also manage a $200 million fund.
0:07.0	So we're over $300 million in revenue across 30 businesses. And all the businesses in the fund are profitable as well.
0:13.0	I don't know. I'm kind of like if that's failing, like sign me up, right?
0:17.0	You've owned a number of agencies. How much revenue lifetime has Meta Lab generated for you the hundreds of millions of dollars of profits not revenue
0:25.6	I don't know that I would still rank it very highly though sass where you
0:29.2	putting sass I would say it's a what do you think about marketplaces well I would
0:33.1	say it comes down to scale a good marketplace like Airbnb I'd say an A I'd rank
0:37.5	marketplaces in general as that's the one I would disagree with you with I feel
0:41.1	like I gotta ask you this because I think you get a lot of shit nowadays think a
0:44.3	lot of people go look at the tiny stock and then they click like max and basically
0:48.2	you see just a downward trend a lot of people I see on Twitter want to kind of
0:53.4	look at that and say oh this guy calls himself the Warren Buffett of the internet and he says he buys these great businesses. But what's going on?
1:01.6	I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel.
1:10.6	Andrew is here. Andrew is one of the most visited guests on the pod. Always good to have you, man. I wanted to play a game with you. You've done many types of businesses. You've done agencies and private equity. And you've started, you know, e-commerce companies. You've done a huge number
1:27.7	of companies in the last 20 years. So I want to do a game where we rank the different types of
1:32.8	businesses that you could start. And we could work out this criteria together. But I think the idea
1:37.3	should be we're not looking at the outlier scenarios. So in every industry, right, the world's
1:42.7	best plumber makes a fantastic living.
1:44.9	That may not mean that plumbing is the best trade to go into. No offense, so the plumbers out
1:49.8	there listening, but we're not looking at just the extreme outlier. So I think that here's my
1:53.7	criteria for a great business, Andrew. It's going to be the median successful outcome.
1:58.5	Okay, so like the sort of like normal case, if you can make it work.
	...

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