Greg Isenberg and the Rise of Multipreneurship
Greg Isenberg’s one of my favorite entrepreneurs because he’s obsessed with business ideas like me.
Greg runs Late Checkout, a holding company that makes over $10 million in revenue and around $5 million in profit per year.
Greg grew up in Montreal, Canada (shout out fellow Canadian!) and was writing blogs early on and starting online communities. Then when he was 17 he was in a school shooting where 19 people were shot and he realized life was short.
He decided to take building internet businesses seriously.
First he build Islands, which was a discord for college students. He sold to WeWork and rode the WeWork wave up to a $47 billion valuation and down to bankruptcy.
Greg decided he didn’t want to do a giant venture backed company again. He wanted to build a profit machine.
He decided to start LCA (latecheckout.agency), which was an innovation agency. But the difference was the positioning. Greg thought that if they came up with an idea that generated hundreds of millions or billions of dollars for a company then that would be worth a lot.
So he didn’t charge $5,000 a month. He charged $1.5 million per year. First year they made $1.5 million with one client, the second year they generated $5 million in revenue. And last year he almost sold it for eight figures.
Side note - take a look at the website. It wasn’t what I expected. And I love the tagline “The Product Innovation Agency for Billion Dollar Brands”
You may be asking how Greg got his first client. He uses what he calls the ACP funnel.
Audience - First he established an audience of 10,000 twitter followers
Community - Then he converts the audience to a community by getting emails and phone numbers, for LCA he threw parties to meet potential clients
Product - Then he builds a product that the community needs
Another one of Greg’s businesses is BoringMarketing.com. He started it with a twitter account where he would post boring marketing advice. Once he had a community he created an AI assisted SEO tool. In 2023 it brought in $350k in profit and it’s on track to generate $2-3 million in profit this year.
The biggest benefit that Greg finds from building multiple businesses is that when one struggles there’s the others generating profits. It also creates less stress as once a project reaches around $100k in profits he recommends finding an operator for the business.
Side note - this is a great masterclass on hiring CEO’s for your companies from Andrew Wilkinson who runs Tiny.
Greg’s other companies include:
You Probably Need a Robot - An AI community
Design Scientist - A design agency
Boring Ads - AI assisted ads
Multipreneurship.com - Community
Brand Kitchen - Builds businesses for creators
Community Empire - Community for creators and entrepreneurs
And if you made it this far you likely love business ideas. So check out Greg’s podcast, The Startup Ideas Podcast. Here’s an interesting one where they discuss how to start up a mural advertising business from someone who had done it in the past (biz idea starts at 9:08).
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