Business Sale
You'll spend two years on the transaction. The outcome gets decided before it starts and after it closes.
Owners put nearly all of their focus on the deal itself and very little on the years that set it up or the life that follows it. That imbalance is where most of the regret comes from, and almost none of it's visible
while the deal is happening.
Who is this for
Before, during, and after the deal
Who is this for
Before, during, and after the deal
01
You're thinking about selling in the next few years.
02
You're in a process now, or holding a signed letter of intent.
03
You closed recently and you're deciding what happens next.
04
You sold, and the part nobody warned you about is the part you're dealing with.
This is written for owners whose sale involves a banker running a process, a quality of earnings review, and a structure with more than one moving part—cash at close, rollover, earnout. Below that, the questions are real but simpler, and a good CPA and a good attorney will usually cover them.
Where standard advice breaks
The deal is the shortest phase. It receives all the attention.
Where standard advice breaks
The deal is the shortest phase. It receives all the attention.
Most guidance about selling a company is about the transaction. How to find buyers, run a process, survive diligence, negotiate terms. That material is useful and widely available.
It also addresses the phase where the least value is created.
The preparation years determine what the company is worth and whether it is transferable at all. The years after determine whether the money accomplishes anything. Both get a fraction of the attention the deal gets, and both are where the durable outcomes are set.
01
Reactive rather than ready
Goals remain unclear, valuation issues remain uncleaned, and the business still depends on the owner in ways a buyer will price. Buyers can read it immediately, and the gap is rarely a rounding error.
02
Leverage reverses at signing
A letter of intent feels like the finish line. It is actually closer to the beginning of the phase where leverage moves to the buyer, when the seller has already closed the deal mentally.
Then there's the part almost nobody is warned about. The wire arrives and the identity that came with the company doesn't survive it. That's not a soft problem appended to a financial one. It's the most common source of post-sale regret among owners whose deals went well.
After the sale
A different problem begins when the wire arrives.
After the sale
A different problem begins when the wire arrives.
Proceeds from an exit behave like any other windfall once they land, and the failure modes are the windfall failure modes. Anchoring on a pre-tax headline number. Expenses that creep. Decisions made in the first ninety days that cannot be undone.
FOR THE PROCEEDS
Sudden Wealth
How to sequence decisions, identify the real number, and prevent a successful transaction from becoming an unsuccessful windfall.
FOR THE LIFE IT MUST FUND
Retirement
When the sale is funding the rest of your life rather than the next venture, the problem becomes one of your income, identity, and time.
What gets sorted first
Five questions that shape the real outcome.
01
Whether the business is transferable, not just profitable.
A company that runs on the owner’s relationships, judgment, and presence is worth less than its earnings suggest, and sometimes considerably less. This is knowable years ahead and fixable only with years of lead time.
02
What the deal actually pays.
Headline price is one number and rarely the operative one. Cash at close, equity rollover, and earnout are three different things with three different risk profiles, and an offer that looks larger can pay materially less. The structure question is where most of the real negotiation lives.
03
Which tax positions need lead time.
Several of the meaningful ones require action years before a sale, not months. Discovering them during diligence means discovering that they are no longer available.
04
What you're actually optimizing for.
Not price. Price is a proxy. Some owners need maximum cash at close, some need the team protected, some need to be gone in ninety days, and some need to stay involved. Those produce different deals, and an owner who hasn't decided will accept whichever one arrives.
05
What happens the following Monday.
The most predictable post-sale difficulty is not financial. Deciding it in advance is the only version that works, because the moment the wire lands is the worst possible time to start.
What I write about
The event is chaos. Bankers, attorneys, tax specialists, valuation advisors, each doing their piece well and none of them looking at the whole. The Business Sale Paradox is largely about that gap. Hundreds of decisions, most of them permanent, most made under time pressure, and nobody holding the entire picture.
Then it ends. The wire hits and the calls stop. Life was one way before and it's another way now, and there's money that has to become something.
Most of the book is about that switch. How much you can spend without wrecking it. What the money can actually fund and what it can't. How it gets invested so a bad year doesn't force you to sell what's falling, and what to do with a drop instead of just enduring it.
And what comes after. Taxes get more complicated after a sale and stay that way. The "can I afford it" questions—the house, the boat, the foundation—only get answered by running them against a plan.
One chapter gets more mail than the rest. The one about a monthly transfer from investments into a bank account. A paycheck. You know the number, so when you're on vacation you're not doing math in your head about whether the trip was a mistake.
Patagonia
How long this usually takes
Patagonia
How long this usually takes
One of my clients, an adventurer and a wildly successful entrepreneur, started thinking about selling long before he ever took a meeting with a banker.
I remember hiking with him through Patagonia. Towering peaks, roaring winds, open wilderness. At 40,000 feet flying over the Andes on the way home, we spent hours talking about what a sale might look like. What kind of buyer would make sense. What he'd do next. What life after would look like.
Ten years later he called and said, "I'm ready."
The business had grown beyond what either of us imagined that day. What struck me wasn't how much the company had changed. It was how much he had.
BEFORE
Build transferability
Prepare the company, clarify the objective, and create options.
DURING
Protect leverage
Evaluate structure, not only price, and keep the advisory team aligned.
AFTER
Design what follows
Give the proceeds a job, then keep running it as your life changes.
The Book
The Business Sale Paradox
A successful sale is more than a successful transaction.
The Book
The Business Sale Paradox
A successful sale is more than a successful transaction.
About Robert
Three decades at the intersection of wealth and life-changing events
Robert Pagliarini is a CERTIFIED FINANCIAL PLANNER™ professional with a doctorate in financial and retirement planning and a master’s degree in psychology. He's a partner and senior wealth advisor at Beacon Pointe Advisors.
He's spent more than thirty years working with people after the ground moves — sudden wealth, the sale of a business, retirement, and Heavy Money from an inheritance or legal settlement. He's written eight books on personal finance. The work and the books have always sat at the same intersection. An event, the money, and the life the money has to support.
Questions readers ask me
These come up more than anything else after someone reads the book.
Questions readers ask me
These come up more than anything else after someone reads the book.
Everyone keeps quoting the headline number. I don't know what I actually keep, or whether it's enough.
Is this enough that I never have to work again? I don't trust my own math on it.
This is the biggest financial decision of my life and it's my first one. Everyone else in the room has done it a hundred times.
Everyone gets paid when this closes. I don't have anyone who's only on my side, and I don't know who's still around after.
I closed four months ago and the money's still in cash. I don't know what it's supposed to be doing, and I'm not sure who to ask.
The book works through all five. If you have a question it doesn't answer, write to me. I read everything that comes in.