He Bought 7 Businesses Too Fast - Here's What He'd Never Do Again with Dev Shah

Buying your first business is exciting. Buying six more before you’ve figured out how to run the first one is where things get interesting.

Dev Shah discovered acquisitions through Acquire.com and quickly went from being fascinated by the idea of buying businesses to actually building a portfolio of them. His first deal was Sourcely AI, a student research tool he bought for just $4,000 while it was making around $500 a month.

A year and a half later, he had grown it to more than $5,000 in monthly recurring revenue and sold it for a low six-figure exit.

But along the way, Dev acquired six other micro-businesses, all for less than $10,000 each, using the cash flow from his original acquisition. And that's where he learned one of the biggest lessons of his acquisition journey: just because you can buy another business doesn't mean you should.

He couldn't integrate them as effectively as he expected. Some were sold. Some were shut down. Others continued running.

Today, Dev has taken those lessons into a much bigger world of acquisitions. He runs a buy-side advisory firm helping search funds, startups, and other buyers source deals, conduct due diligence, negotiate, and get acquisitions across the finish line.

And he's seen plenty go wrong.

Sellers who disappear after an LOI. Businesses with information that turns out to be fake. Owners claiming revenue that can't actually be verified. Deals that look attractive until you start pulling apart the numbers.

In this episode, Jaryd sits down with Dev to unpack what buying seven businesses taught him about moving too fast, how to build a buy box around your own skills and competitive advantages, and why serious buyers need to spend time in the market before they ever make an offer.

Dev also breaks down his approach to due diligence, why you should treat those 30 days as if you're already taking over the business, how to avoid becoming emotionally attached to a deal, and why your relationship with the seller can be just as important as the numbers on the spreadsheet.

From $4,000 micro-acquisitions to sourcing deals for buyers with millions of dollars behind them, Dev has seen both sides of the acquisition process.

If you're thinking about buying an online business, especially for $100K or less, this conversation is full of lessons that could save you from making the same mistakes.