On Owning

The work behind buying, owning, and exiting a business in the lower middle market.

Why this exists

Owning a business is the hardest job most people will ever take on. The payoff is freedom. Buying one starts it. Exiting one completes it. On Owning is about the work behind all three.

Who I am

I’m Lloyd Silver. Over two hundred M&A deals worked across both sides of the table. Twenty-plus years owning and operating Main Street businesses of my own.

I work with buyers acquiring their first or next business and with owners getting exit-ready and then through the deal. Running my own business keeps the writing here close to what ownership feels like and to the harder question that arrives the day after a seller signs.

What you’ll get

Here you’ll find insights and lessons from inside the practice. The writing is built to be read fast and used soon. Some pieces zero in on patterns across deals that close and deals that fall apart. Others focus on operator decisions that move the multiple.

The throughline is plain language on subjects most M&A people overcomplicate.

Three sections to follow

For Owners. Exit readiness and value-building.

For Buyers. Running an acquisition process that closes.

Deal Room. Stories and pattern work that crosses both.

New writing shows up in your inbox regularly. Shorter takes mixed in when something deal-related is worth flagging the same week.

Credentials

CFA charterholder, Certified Business Broker, principal at Two Oaks Advisors. Two years at Contrarian Thinking leading the Contrarian Community for buyers and the Growth Boardroom for owners.