One thing I’ve noticed is that a lot of owners feel like they have a plan because they have good people around them.
A financial advisor.
A CPA.
An attorney.
Maybe an investment banker they’ve had a conversation or two with.
On paper, it looks like a team.
But when you start asking how all of those pieces actually fit together…
How the business sale connects to the taxes, which connects to the estate plan, which connects to the reinvestment strategy, which connects to what your life looks like on the other side of the deal…
There’s usually a pause.
Because no one is coordinating it.
And if no one is waking up in the morning thinking about how all the moving parts of your exit work together, you don’t have a plan. You have parts.
That’s usually where things start to slip.
Not all at once, but in ways that can become expensive later.
Hey — I’m Ryan Guth.
I sold my company about a decade ago, wrote a book called Permission to Exit, and now I’m a CERTIFIED FINANCIAL PLANNER™ professional working with post-exit entrepreneurs.
One of the things I help owners do is think through the full picture of an exit — not just the transaction, but everything around it.
Because in practice, those decisions often matter more than owners expect once the deal is done.
Let me give you an example.
I was working with a veterinary service owner not long ago. Decent margins, steady growth, additional vets being hired to relieve the owner from her duties more and more.
She had an offer on the table that looked strong on the surface.
But when we started pulling it apart, a few things became clear.
A large portion of the deal was structured as rollover equity, meaning she’d stay invested in the business after the sale.
There was also an earn-out tied to future performance, which introduced real uncertainty into how much she’d actually receive. And the tax implications of the deal structure hadn’t been fully modeled against her personal situation.
None of those things are unusual.
What was missing was someone looking at all of it together and asking:
“Given what you actually want your life to look like after this… is this the right structure?”
Because this wasn’t just a financial decision.
She had a spouse who also worked in the business and he was ready for a different pace.
One daughter in college and the other in the working world – married, with a child.
Plus, vets work hard. Lunch is often replaced by an emergency surgery or some other fire to put out. She had a burning desire to step back from the business, not commit to another five years.
So the question wasn’t just “Is this a good deal?”
It was “Is this the right deal for you and your spouse?”
That’s the conversation that usually isn’t happening amongst the siloed professionals.
Here’s the other pattern I see a lot… and it connects to something I talk about in a different video on timing.
Owners tend to think about selling when they feel ready. Like in my example…
They’re tired. They’ve been pushing for years.
Maybe the industry is different than it was when they started. Maybe they’re starting to wonder what they could be doing instead. That’s a natural place to start.
But the business doesn’t always align with that timeline.
Sometimes the business is in a strong position - clean financials, solid growth, real market interest - and the owner just isn’t prepared to act on it yet. So the opportunity passes.
And sometimes the owner waits.
Margins start to compress.
Key people leave.
The growth story gets harder to tell.
And even if they’re personally ready, the business isn’t in the same position it was.
Those timing decisions aren’t just about the market.
They’re about how your business, your personal life, and your financial plan all line up at the same time.
Which requires someone looking at the full picture.
I think about this like a quarterback.
In a good offense, you have a lot of talented players. A strong line. Receivers who know their routes. A running back who can create space when needed.
Each of them has a job, and they do it well.
But someone still has to call the plays.
Someone has to read the defense, make adjustments in real time, and see what’s actually happening… not just their piece of it.
Without that, you don’t have a coordinated system. You have individual effort.
That’s what I see as the default.
Good professionals…
But nobody responsible for how the decisions interact.
And the cost of that doesn’t always show up in obvious ways.
It shows up in things like paying more in taxes than necessary because the structure wasn’t thought through early enough.
Accepting deal terms that carry more risk than the owner realized, because no one connected the legal structure to the personal values and goals.
Holding too much or too little equity post-sale without a clear reason tied to the plan.
Or simply landing somewhere that looks successful on paper, but doesn’t actually support the life the owner had in mind.
The sneaky thing is that these are quiet mistakes. They add up though.
And they usually surface after the fact, when there’s not much you can do about them.
What I try to do with clients is shift the timeline on those decisions.
Instead of waiting until a deal is already moving, we start earlier. As soon as possible. Even if selling is 2 years away.
So think about this. What does an ideal outcome look like for you?
Not just financially, but in terms of your time, your future involvement, your family, your next chapter, future business ideas?
If you sold in the next three to five years, how would you want the deal structured?
How much risk are you comfortable carrying post-sale?
What role do you want?
How should your tax strategy, estate plan, and investment plan be aligned with that outcome?
Those questions don’t get answered in a week. They take some thought.
Here’s the biggest question of all. Why isn’t your advisor already asking you these things?
This stuff takes time and coordination from someone who’s been there and done that.
It’s so much better to think through this stuff before you’re ready to sell. You’ll be in a clearer headspace without deadlines and due diligence.
If your business is doing a million dollars or more in annual profit, and you’ve started thinking about what an exit might look like, here’s the question worth asking:
Is anyone actually coordinating this for me?
Not managing an old Roth IRA. Not filing your tax returns. Not handing you a packet about your future death to fill out with your spouse on your date night.
Someone to just get this all done for you, so you can do what you do best–run your business and attend to your family.
Because these things DO have to get done.
If you want to talk it out for 15 minutes, let’s do it.
Not a pitch.
I just want this to be great for you.
Thanks for watching, and I’ll see you in the next video.