Andrea spent a decade in operational and financial leadership at TGG Accounting before becoming CEO of Exit Consulting Group. She's a Certified Exit Planning Advisor who understands how businesses are built, run, and made ready to sell. Named one of the Top 50 Women Leaders of California for 2025.
Deal fatigue when selling a business is not just about being tired of meetings, documents, and negotiations. In Andrea Steinbrenner’s segment, it becomes clear that fatigue is what happens when owners start too late, clean up too much under pressure, and realize mid-process that they never fully defined the outcome they actually wanted.
Her contribution to the event is important because she brings the internal side of the transition into view. Laura focuses on tax architecture. Josh focuses on exit readiness. Shaaya focuses on buyer logic. Andrea focuses on what the owner is living through while all of that is happening.
Andrea begins by circling back to several issues Laura raised earlier: entity structure, owner compensation, and timing. Her point is that those are not just tax topics filed away in the CPA relationship. They become live transaction issues when a sale process begins.
If compensation has been handled inconsistently, if the structure was never aligned with the owner’s goals, or if the owner has been running too many personal and business decisions through the company without a clear strategy, the process becomes harder. The owner is forced to fix foundational items while also navigating buyers, diligence, and emotion.
That is exactly where fatigue begins. What could have been handled calmly over time now has to be handled in motion.
This is also why implementation matters so much. For a related perspective, see Why Most Tax Strategies Never Get Implemented (And How to Fix It).
Andrea argues that owners often focus too narrowly on liquidity. That is understandable. The transaction is usually large, personal, and financially defining. But it is not the only question that matters.
She introduces a broader lens that includes not just liquidity, but also legacy and relevance. In practical terms, that means the owner should think beyond “What number do I want?” and ask what the deal means for employees, relationships, identity, continuity, and life after closing.
That broader framing is not soft or secondary. It can directly influence the quality of the transaction and the owner’s willingness to accept certain structures, tradeoffs, or buyers.
The most memorable part of Andrea’s session is the story she tells about an owner who believed everything would be fine if he simply got “his number.” She then walked him through a hypothetical close where the money hit the bank, the celebration happened, and the deal looked perfect on paper—until he had to tell his employees that key long-time people were gone.
The story lands because it exposes something many owners avoid until very late: the purchase price can be right and the outcome can still feel wrong. You can hit the number and still dislike the buyer, lose people who mattered, or end up constrained by deal terms you barely thought about because liquidity dominated the decision.
Andrea’s point is not that price is irrelevant. It is that price alone is too narrow to carry the whole weight of a transition.
One of the strongest bridges Andrea makes back to tax strategy is this: if the owner thinks more broadly about the outcome, good advisors may still help them get closer to the economic result they want even if it does not all show up in purchase price. The tax strategy, planning, and execution can still support the larger win.
In other words, not everything has to be solved by squeezing a few more dollars into the offer itself. Sometimes the better outcome comes from understanding the total after-tax picture, the transition structure, and the practical implications of the deal terms.
For IRS guidance relevant to business sale treatment, see the Publication 544 page and the IRS sale of a business overview.
Andrea closes with a warning against what she calls the “nasty R-word”: regret. That regret usually does not come from one single mistake. It comes from a stack of smaller decisions made without enough clarity. Owners delay. They assume they can fix things later. They prioritize the obvious number over the less obvious consequences. Then, when the process accelerates, they discover how little time is left to shape the outcome.
Her practical message is to plan, prepare, and execute early enough that the finish line feels like a win in the full sense of the word. That means financial win, tax win, people win, and lifestyle win.
If you are re-evaluating your advisory bench before that kind of process, read How to choose a tax advisor for your business.
Andrea’s talk is the reminder that a sale is not just a financial event. It is a human event with tax consequences. The owner who plans early has more room to protect both. The owner who waits often discovers that the emotional side and the tax side collide at the worst possible time.