One thing I’ve noticed after talking with more than 100 founders in the last nine months is this.
When someone tells me they regret selling their business…
Almost never do they start by saying they didn’t get enough money.
That’s what most people expect.
Instead, the regrets usually sound more like:
“I wish I had started planning earlier.”
“I wish my wife and I had talked about what life would actually look like afterward.”
“I wish I’d known then what I know now.”
Hi, I’m Ryan Guth. I sold my own business years ago, wrote a book called Permission to Exit,
and today I help founder-led business owners prepare for one of the biggest financial and
personal transitions of their lives.
And over the years, one of the things I’ve learned is this:
It’s not what you make on the deal.
It’s what you keep.
Not only financially.
But in your relationships.
Your purpose.
And your peace of mind.
Today I want to walk through the two biggest regrets I see after owners sell their businesses,
because both of them are avoidable if you start early enough.
And if, while you’re watching this, you realize you’re within a year or two of thinking about a sale,
there’s a link below where you can schedule a conversation with me. No pressure. We’ll simply
talk through where you are and whether there are things worth doing now while you still have
time.
Let’s start with the first regret.
The first regret is waiting too long to prepare financially.
Founders don’t wait because they’re careless.
They wait because they’re busy! Doing exactly what made them successful in the first place.
Working on their business.
They’re still driving growth.
Leading meetings.
Probably closing major customers.
Or holding the key relationships.
And if they’re honest…
They kind of enjoy it.
They’ve built a company that allows them to do more of the fun stuff.
The problem is that preparing for a business sale isn’t another project you can stack on top of
everything else.
You can’t run a growing company while simultaneously managing your own M&A process,
responding to due diligence requests, coordinating your CPA, your estate attorney, your
valuation firm, and your personal financial plan.
That’s like an astronaut who also tries to build the rocket and command mission control
themselves. I have a feeling “Houston may be getting a call” if you follow.
The best exits not only have a plan, but a team to execute all the parts.
I often think about it like this.
Imagine you’re taking your fifty-foot boat out into open water.
Everything feels calm while you’re in the harbor.
But eventually you’re surrounded by massive commercial tankers.
Those larger ships aren’t slowing down because you’re not prepared.
That’s what selling to a sophisticated buyer often feels like.
Private equity firms and strategic acquirers have entire teams dedicated to evaluating every
detail of your business.
They’re used to doing this every day.
For most founders, it’s the first time they’ve ever sold a company.
That’s why planning while the water is calm matters.
Not once you’re already surrounded by the big ships.
One of the biggest mistakes I see has nothing to do with negotiations.
It’s the quiet, boring work that doesn’t get done beforehand.
- Tax planning.
- Estate planning.
- Structuring ownership.
- Preparing trusts.
- Coordinating with legal advisors.
Those aren’t exciting conversations.
But they’re the ones that help you keep the most money post-sale.
And here’s something many owners don’t realize, in my experience.
Once a serious Letter of Intent arrives, certain tax and estate planning opportunities simply
disappear.
The window closes because a buyer has inadvertently valued your company for you.
Valuation experts have to take this into account when valuing your company’s shares prior to
using the tools at our disposal to save you on taxes now and in the future.
That’s why I often tell owners I’d rather meet them two or three years before they think they’ll
sell than two or three months before.
That runway changes what’s possible.
Another part people underestimate is coordination.
Most successful owners already have some decent professionals.
They have a CPA or accountant.
Maybe the estate attorney they did their basic will or trust with.
Perhaps a financial advisor who does their company’s 401(k).
Sometimes a buddy who’s an investment banker.
The challenge usually isn’t finding good people.
It’s getting all of those people moving in the same direction at the right time.
Quite honestly, I spend a surprising amount of my time quarterbacking everyone else’s work.
Following up.
Keeping timelines moving.
Making sure conversations happen in the right sequence.
Sometimes I joke that I’m the Chief Revenue Officer for everyone else’s firm because I’m
constantly making sure things keep moving forward.
Somebody has to own the process. Thank goodness for me. If I didn’t do what I do, these poor
people would never get paid.
I see this all the time. A new client comes to me and their existing professionals are doing their
individual jobs, but nobody is coordinating the overall outcome. That quarterback role is central
to my planning philosophy.
So I’ve got a question for you.
If someone brought you a serious offer next quarter…
Would your personal financial plan…
Your tax strategy…
And your estate plan already be ready?
Or would you spend the next several months scrambling?
That answer tells you more than you might think.
Now let’s talk about the second regret.
I think this one matters even more than the first.
The second regret is never having the conversation at home.
Selling a business isn’t only a financial transaction.
It’s a family transition.
One of the first conversations I encourage owners to have has nothing to do with valuation or
which trust structure to utilize.
It’s this.
What does life look like after the sale for you and your family?
Are you staying employed?
For how long?
Will you be CEO under new ownership?
How about serving in an advisory role?
Working just part time?
Or are you making a clean exit?
Those terms are often negotiable.
But it’s difficult to negotiate confidently if you haven’t first decided what you actually want.
Especially with your spouse.
I’ve noticed something over the years.
By the time many of my clients reach this stage of life…
They don’t really have money problems anymore.
They have identity problems.
They have relationships that need nurturing.
They have post-exit purpose questions.
They have to re-learn financial stewardship because it feels different.
Those become the real issues.
Because no amount of money fixes that stuff. I’d venture to say adding money to unresolved
issues makes them worse.
I’ve watched owners spend years building incredible businesses while unintentionally neglecting
conversations that mattered even more.
What do we want our family to look like after this?
Where do we want to live?
How much are we actually going to work?
What kind of parents or grandparents do we want to become?
What does our purpose become when the business no longer needs us every day?
Those aren’t spreadsheet questions or financial planning software questions.
They’re heart questions.
And they shape the success of an exit more than the purchase price.
Remember Scrooge McDuck diving into his vault full of gold coins at the beginning of Duck
Tales? Did you ever meet his wife?
[pause]
I didn’t think so.
One thing I tell owners fairly often is this.
If your spouse and I have never sat in the same room together…
We’re missing something important.
Because I can help coordinate the financial plan, help you save on taxes, run a smooth
process…
I got that.
But if the two of you aren’t aligned before the transaction…
That’s much harder to fix afterward.
No second home…
No boat…
No luxury vacation…
Will ever replace being aligned with your spouse, your family, your values, and the purpose you
believe you’ve been called toward.
Money is a wonderful tool.
But it’s a terrible substitute for healthy relationships.
And no AI or robo-advisor is ever going to help you navigate that conversation.
Because it’s a human one.
So if you take nothing else away from this video, remember these two questions.
Am I preparing early enough financially?
And have we actually talked about what life looks like afterward?
Because those are the two questions that seem to separate owners who look back with
confidence from those who quietly carry regret.
Now if your business is profitable (like more than $1 million in EBITDA) and you’re thinking
about selling sometime over the next few years, I’d encourage you not to wait until the process
has already started.
Let’s have the conversation while there’s still time to shape the outcome.
There’s a link below where you can schedule a conversation with me.
No sales pitch.
No obligation.
Just an opportunity to think through where you are today, where you’d like to go, and whether
your financial plan, your family plan, and your exit plan are actually working together.
Thanks for watching, and I’ll see you in the next video.