Why Adam Rossi Wanted to Undo His Exit

Adam Rossi built a 250-employee software company serving law enforcement and intelligence agencies. They routinely beat Lockheed Martin in head-to-head bids. 

Then a banker came back with five acquisition offers — each at the “absurd” number Adam and his wife had thrown out as a hypothetical. The winning bid came from SRA International, a publicly traded defense contractor, for a price that created generational wealth for his family. Adam took all cash and walked away with no earn-out. 

But as Adam discovered, the hard part wasn’t negotiating the deal — it was figuring out what to do after it closed. 

In this After the Deal episode, you’ll discover: 

• Why Adam wished he could “undo the whole sale” in the years right after his exit. 

• The surprising reason he took all cash — and why he now warns founders to consider keeping equity. 

• How a family member’s reaction to his sale tested his resolve. 

• Why he refused an earn-out — and what happened when he ended up working there anyway. 

• The hidden downside of having no financial diversification before a sale. 

• Why the first company you buy after an exit is the one most likely to fail. 

• How sudden wealth can trigger awkward — even entitled — requests from extended family. 

Show Notes & Links

Connect with Adam on LinkedIn

Definitions

Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.

Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.

Errors and Omissions Insurance (E&O): This is a form of liability insurance that protects companies and their employees against claims of inadequate or negligent actions, particularly in professional advice and services.

Quality of earnings (or “Q of E”): When an acquirer has secured an exclusive position to purchase your business via an LOI, and the transaction is over $1 million or $2 million in value, the acquirer will often hire an outside CPA firm that specializes in reviewing financial documentation, to provide an analysis of your historical EBITDA compared with the values provided in your CIM. A Q of E report can often be a milestone, enabling an acquirer to consider a major portion of their due diligence completed.

Re-Trading: This occurs when a buyer attempts to renegotiate the purchase price of a deal after initially agreeing to one. It is often seen unfavorably as it occurs after due diligence, seemingly exploiting newly discovered information.

About Our Guest

Adam Rossi

Adam Rossi is a tech entrepreneur who built a 250-person software company serving law enforcement and intelligence agencies—often outcompeting giants like Lockheed Martin in head-to-head bids. When a banker returned with five acquisition offers matching the “absurd” figure he and his wife had once tossed around, Adam accepted an all-cash deal from SRA International, a publicly traded defense contractor. The sale created generational wealth for his family, with no earn-out or strings attached.

After the exit, Adam learned that the hardest part of selling a company isn’t the negotiation—it’s deciding what comes next. Today, he shares his journey and insights to help other founders navigate the challenges of building, selling, and redefining success beyond the business.