Jackie Ossin Hirsch: The Business Therapist of Florida M&A

In the world of lower middle-market M&A, Jackie Ossin Hirsch is a force of nature. A Certified Business Intermediary (CBI) and the founder of Crowne Atlantic, Hirsch has spent 26 years in the trenches of Florida business brokerage. While the industry average for a broker might be a handful of deals a year, Hirsch has closed over 400 transactions in her career, ranging from small Main Street shops to $50 million enterprises.

Her entry into the industry was anything but glamorous. In 1998, at age 22, she answered a newspaper ad and was hired by a broker looking for anyone with a pulse and a real estate license. "I just started, and everybody in the office made fun of me and didn't think I could do it cuz I was literally more than half everybody's age," Hirsch shared in one appearance on the Top M&A Entrepreneurs Podcast.

By age 26, she founded her own firm. Today, she is known not just for her volume, but for her "no-filter" approach to deal-making—a style she describes as a mix of directness, humor, and necessary "business therapy."

Hirsch views a small business not merely as a P&L statement, but as a "bespoke creation." For many sellers, exiting is a traumatic life event comparable to a death or a divorce. She notes that business schools teach finance, but they do not teach how to handle the psychological ungluing of a founder selling their life's work.

This emotional volatility requires buyers to have high emotional intelligence (EQ), not just high IQ. Hirsch recounts a meeting where a buyer from Brooklyn came in firing rapid questions at sellers from Iowa, causing them to physically recoil. The deal died immediately due to culture clash. Conversely, she saved a deal between a seller from West Virginia and a buyer from Maine by explicitly calling out their cultural communication gaps, allowing them to understand each other's "language."

Hirsch specializes in construction, manufacturing, and business services—industries where "creative accounting" is common. She warns first-time buyers that small business books rarely follow GAAP principles. She has seen sellers bury the cost of a personal boathouse ($250,000) in their cost of goods sold, or pay a child living in another state a six-figure salary for negligible work.

Because of this, she advocates for a "Quality of Earnings (QofE) Light" for smaller deals. This involves spot-checking specific jobs—tying the purchase order to the invoice, to the bank deposit, and matching it against labor and material costs.

"There are no myths in business brokers. Everything that you hear on the internet is true. You could buy a business no money down right from a business broker. I did do two of that last year, but I don't like to tell people that," She says. While possible, she notes these "no money down" deals usually require the buyer to already own a business with the same NAICS code, debunking the social media myth that anyone can do it easily.

Hirsch has witnessed the influx of "searchers"—individuals, often with MBAs, looking to buy a business to run. Her advice to them is blunt: do not waste a broker's time. She receives 30 to 50 outreach calls a week and rejects almost all requests for "coffee chats."

"Call with a point and call with a reason... If you want to get seen deals, you need to be very specific in your outreach," she says.

To be taken seriously by a high-volume broker, Hirsch advises searchers to have three things ready before making contact:

She is skeptical of buyers who treat the search as an academic exercise, citing one group that looked at 2,000 businesses before buying one. "I can't show somebody 2,000 businesses... that's not realistic," she notes.

For those looking specifically in the Sunshine State, Hirsch points to a unique resource: BBFMLS.com. This is a state-wide MLS specifically for businesses, managed by the Business Brokers of Florida. She notes there are approximately 861 brokers in the state, transacting about 1,100 deals per year through that system.

However, even with organized data, external chaos is inevitable. Hirsch recounted a deal that took 1.5 years to close, plagued by zoning issues and an absentee landlord. When they were finally ready to sign, the closing was delayed again—because Taylor Swift was in town.

"The bank was located in a town where Taylor Swift was going to be... so we had to delay it another week because of Taylor Swift," Hirsch comments.

Reflecting on a career that started with ridicule and evolved into over 400 closed transactions, Hirsch attributes her success to "betting on herself." She bootstrapped her firm at 26 and maintains a philosophy of radical authenticity.

"I can't help but be myself. I would be a terrible actress. Some people find it direct, some people might find it offensive... but it's still usually with a lot of love," Hirsch said in one appearance on the Lead IN Podcast.

Her advice to anyone entering the market is to embrace the risk. She encourages buyers to stop looking for a perfect, risk-free deal because it doesn't exist. "The only guarantee in life is that we will die," she told her daughter when discussing fear. In business, as in life, Hirsch believes the only way out is through.