We were in the final stretch of closing a deal that had taken months to reach an LOI. On paper, everything worked. Off paper, we could feel it starting to slip.
The company, a SaaS business in the telecommunications space, was growing at an incredible pace, nearly triple-digit year over year, with healthy margins and one big but: massive client concentration.
The offers we had initially received fell short of our founder’s expectations. After weeks of back-and-forth with the two final acquirers that felt like the right strategic fit, we finally landed on a valuation and deal structure that made him smile and say, “This is it.”
And then he started lagging in due diligence.
We worried he was having second thoughts.
That’s when it hit me. I remembered what another founder we once worked with had told me: "Selling my business was the best and the worst day of my life."
The best, because years of building, risk, pressure, and relentless decision-making had finally crystallized into a tangible result. The worst, because the next morning he woke up and realized something unexpected: the thing that had structured his days, probably even defined his identity, and absorbed most of his mental energy was suddenly… gone.
At L40°, we spend our days advising founders through exits, from the first valuation assessment to buyer dynamics, deal structure, negotiations, closing, and everything in between. But what happens after the wire hits is often far more uncertain than most people anticipate.
The truth is this: selling a business is not one transaction. It’s two.
You sell the company. And then you have to redesign your life, your identity, and often, your relationship with money.
And almost no one prepares you for the second part.
Why life after selling your business can feel so disorienting
For most founders, their company isn’t just an asset. It becomes an extension of who they are.
Research supports this. Academic studies on entrepreneurial exits show that founders often experience a deep identity disruption after selling, particularly when the business has been central to their sense of self and social role.
This helps explain a statistic frequently cited in exit-planning circles: roughly 75% of business owners report some form of regret or emotional difficulty within the first year after an exit, even when the outcome is financially successful.
That regret rarely sounds like, "I shouldn’t have sold."
More often, it shows up as a quieter, heavier question: "And now what?"
A question that can open the door to deeper, almost existential reflections:
- “I didn’t realize how empty it would feel.”
- “I lost my sense of purpose.”
- “I thought the money would make this easier.”
Because while money solves liquidity, and those extra zeros in your bank account may finally enable the vacation you postponed or the beach house you always wanted to buy; capital does not automatically solve identity, structure, or meaning.
And for entrepreneurs who don’t have another venture immediately pulling them forward, that gap can feel especially destabilizing.
Recommended: Sell-Side M&A: An In-Depth Guide for Tech & SaaS Founders
The pressure before the exit
As founders get closer to an exit, psychological pressure often intensifies, not because of the money itself, but because of what the decision represents.
Selling a company forces founders to confront questions that rarely have clean answers:
- Am I leaving value on the table?
- What if I hold on longer?
- Is this the right moment, or just a convenient one?
- Am I giving up something I’ll never be able to rebuild in the same way?
These doubts don’t appear in spreadsheets or data rooms, but they can quietly slow momentum at the most critical moments.
I once worked with a founder who would call me almost every day during due diligence. The deal was strong, the buyer was right, and the terms were fair. Still, as we got closer to closing, his anxiety grew.
One day, after weeks of back-and-forth, I finally asked him what he really needed.
He paused and said, very honestly: “A therapist.”
Then he laughed, not as a joke, but with the ease of someone finally naming what was going on.
This wasn’t a sign of weakness. It was human. Letting go of a business you’ve built over many years inevitably affects more than just your financial outcome, no matter how successful the liquidity event may be.
Like many founders approaching an exit, he wasn’t struggling with the numbers. He was grappling with finality, identity, and the weight of making a decision that would permanently close one chapter of his life.
All while still being expected to perform flawlessly inside a high-stakes transaction.
Recommended: What happens (to the business) when you sell your business?
When the exit is done and the silence sets in
Once the company has been sold, a different psychological dynamic often emerges.
There is a concept in wealth psychology known as Sudden Wealth Syndrome. It is not a clinical diagnosis, but a useful framework for understanding what can happen when a major liquidity event triggers stress, anxiety, guilt, or disorientation.
The Sudden Money Institute describes this as a transition problem, not a money problem. Founders may experience:
- Loss of routine and decision-making structure
- Anxiety about “doing something wrong” with the money
- Pressure to invest, help others, or justify the exit
- A sense of isolation, as these concerns can feel difficult to talk about
This doesn’t mean something has gone wrong. It means a major life structure has been removed, and a new one has not yet formed.
The four psychological stages after an exit
Overall, working closely with founders through exits, and watching each of them move through the process in their own way, has pushed me to look more closely at the psychology behind it.
No two founders experience an exit in the same way. Some move on quickly, energized and ready for what’s next. Others pause. They reflect on what they’ve built, who they’ve become, and what they actually want moving forward. Those pauses often lead to the most meaningful conversations.
If we try to structure that emotional journey, research from the Sudden Money Institute suggests that major liquidity events often unfold across four transition stages:
1. Anticipation
Excitement, potentially a degree of fear, and constant projection into “after.”
Common mistake: making big life plans before the deal actually closes.
2. Ending
Relief mixed with grief. The company is no longer yours.
Common mistake: minimizing the emotional loss because “this is what I wanted.”
3. Passage
The in-between. The old identity has dissolved, but a new one not yet formed.
Common mistake: rushing into new ventures or investments to fill the void.
4. New normal
A new rhythm begins to emerge. This is an opportunity to be intentional about how you want to live and work going forward.
Common mistake: assuming purpose will appear on its own.
Being aware of these stages doesn’t remove uncertainty, but it helps reframe it. It can be useful for founders to recognize that what they’re experiencing is not failure or second-guessing, but part of a broader transition.
And once that transition is acknowledged, the question naturally shifts from why this feels strange to what to do next.
That’s where the first 30 to 90 days after an exit can become so important.
What to do after selling a business: The First 30–90 Days
Founders often ask me what they should do immediately after closing.
My answer is usually counterintuitive: “I don’t know. Take time for yourself?”. And that question mark is intentional.
Not because the answer is vague, but because there isn’t a universal one. Every founder exits with a different level of exhaustion, clarity, and readiness for what comes next.
What I do know is this: pause. That’s what the question mark really stands for.
The Financial Industry Regulatory Authority (FINRA), which publishes guidance on managing large financial windfalls, consistently emphasizes one principle: “avoid irreversible decisions early on”.
In practical terms, that means that the first 30 to 90 days are often best spent focusing on three things:
- Creating psychological distance from the transaction
- Stabilizing your financial setup
- Rebuilding personal structure (time, routines, health)
This is also the right moment to assemble what I think of as a personal board:
- Tax advisor (post-close planning matters)
- Wealth planner or CIO-type advisor
- Estate attorney
- And, yes, sometimes a coach or therapist
Let’s call this… risk management, perhaps?
Financial planning after selling a business starts with behavior
In fact, one of the biggest misconceptions founders have is that post-exit risk is primarily about markets. However, behavioral risk plays an equally important role.
FINRA’s research on windfalls highlights that poor sequencing, emotional investing, and decision fatigue (not bad asset allocation), are the most common sources of long-term damage after liquidity events
That’s why I like to think in terms of a simple “bucket” framework.
The Bucket Plan: How much cash to hold after selling a business?
The right amount of cash to hold on to will always depend on the size and structure of the exit, as well as on what you plan to do next.
That said, a common framework could look like this:
- Operating cash: 1–3 months of personal expenses in checking
- Safety liquidity: 4–6 months of expenses in high-yield savings or money market funds
- Near-term planned uses: 6–24 months of known expenses, such as taxes, real estate purchases, or lifestyle changes
- New ventures fund: a defined allocation to reinvest in building, acquiring, or backing what comes next
The goal isn’t so much about optimization, but flexibility. Enough liquidity to avoid rushed decisions, without holding so much cash that it creates anxiety or inertia.
One technical point many founders overlook is FDIC insurance limits. Standard coverage is capped at $250,000 per depositor, per bank, per ownership category.
After an exit, cash concentration risk becomes very real and entirely avoidable with proper structuring. Getting this right early is less about yield and more about protecting optionality while you decide what comes next.
Investment behavior and common post-exit mistakes
Then, there’s the decision-making component of an exit. Many founders move from operating within a capital structure shaped by their business to suddenly having far greater personal liquidity and discretion. That shift alone can distort judgment, even for highly disciplined and financially sophisticated operators. The challenge isn’t knowing what to invest in, but knowing when and why.
Some of the most common post-exit investment mistakes I have seen include:
- Moving too fast. Jumping into new deals or asset classes simply to recreate momentum or fill the space left by the business.
- Overconfidence after a successful exit. Assuming that a strong operating outcome automatically translates into an investing edge. Being a successful founder-operator requires a very different skill set from becoming a successful investor.
- Revenge or reward spending. Making large purchases or commitments as a reaction to years of self-control.
- Scattered capital allocation. Writing many small checks without a clear thesis, governance, or time horizon.
- Delegating too much, too early. Handing over full decision-making to advisors as a way to avoid engaging with uncertainty.
It’s important to note that none of these behaviors come from lack of intelligence or experience. They come from operating without the structure the business used to provide, and from not structuring a clear post-exit strategy.
This is precisely why liquidity planning and pacing matter. Not just to maximize returns in the short term, but to give yourself the space to make decisions deliberately, once the emotional noise of the exit has settled.
Designing a meaningful life after selling your business
Many times, something that may surprise founders is that they don’t actually miss the company. What they miss is something else. This could be:
- Being needed
- Routine
- Goals
- Momentum
- Belonging
- Having a reason for their intensity
Money creates freedom, yes, sure, but freedom without structure can also feel unsettling. Especially at the beginning.
The founders who thrive post-exit tend to consciously design a meaning portfolio, spanning:
- Health
- Relationships
- Mastery and learning
- Contribution
- Selective professional engagement
The truth is that identity doesn’t disappear after an exit, nor does it automatically transform. It needs a new container, and often a renewed sense of purpose.
Many exited founders actively seek out peers who have gone through similar transitions. They gather through retreats, small groups, or informal networks. In these settings, community can be just as impactful as it was during the building phase, providing shared context, perspective, and continuity at a moment when structure has been removed.
Read: When to Sell Your Business: The M&A Consideration Stage
A Good Exit Is a Transition, Not a Finish Line
Most exits are planned financially, but very few are planned personally.
The difference between the two becomes apparent only after the deal closes, when the noise subsides and the questions start to surface. Thinking about those questions early does not weaken an exit. It strengthens it.
At L40°, we work closely with founders on how they sell their business, from valuation and buyer fit to deal structure, transition, and closing. That’s how we also know that some of the strongest exits we’ve seen are those where founders also think ahead about who they want to be once the company is no longer theirs.
That kind of intentionality requires reflection, clarity, and an honest understanding of what the business has provided beyond financial outcomes. It’s, at the end of the day, a psychological exercise just as much as it can be a strategic or financial one.
Because the wire transfer is just one day. However, what determines whether an exit feels complete unfolds over the months and years that follow.
Life after selling your business is not just a footnote to the deal. It can be the chapter that gives the transaction its meaning.
