Sep 18, 2026 · 58 min · 9 segments
This episode is for founders and family business owners preparing for a liquidity event: a sale, recapitalization, or IPO that turns years of work into a new chapter for the family. Co-hosts Claire…
S. Craig Stone IIGuest
Matt McClintockHost
Brendan BybeeGuest
Claire MartinHost
Yeah, you know, that's it goes back to the Stephen Covey's comment about, you know, begin with the end in mind.
Where do you where do you think you want to be at the end of the day? And, you know, as you kind of alluded to, most times.
Entrepreneurial families may only have one major liquidity event in their entire lifetime.
If they're serial entrepreneurs, they may go through that experience several times and they get better with each evolution of it because most times they start with they don't know what they don't know.
And their lived experience through the first one may suggest whether they ever want to repeat that.
It's interesting that Brendan and I can drip on the families over the years and say, hey, you need to prepare for this.
What is the ultimate solution? exit strategy, because we tell all families, you're going to exit your business one way or the other.
It's either by choice or chance or design or default, but it's going to happen.
And then all of a sudden it's like, oh, my goodness, how much do we have to, what do we do now? And we have a compressed timeframe.
I like to say that if we can get ahead of a transaction, I mean, this sounds a little silly, but three to five years before it ever happens, we can have phenomenal results, both quantitative from a planning and tax perspective, but qualitative because we know exactly where the dominoes are going to fall when that event happens.
It's usually the clients that get surprised by an offer out of the blue, and they haven't really thought through what this really means in that moment.
So getting them mentally and emotionally prepared for that is a big part of it.
The tax planning more often than not, regardless of our timeframe, takes care of itself.
Yeah, I'd say, you know, to that point, planning isn't really just about kind of controlling the future, controlling outcomes.
And the earlier you start planning, the more options you're going to have because, you know, they come up and somebody suddenly gives them an offer.
Before they know it, they're further down the path than they think before they finally reach out to their advisors.
And a whole swath of options are now off the table because of where they've already taken something to.
Yeah, you know, that's it goes back to the Stephen Covey's comment about, you know, begin with the end in mind.
Where do you where do you think you want to be at the end of the day? And, you know, as you kind of alluded to, most times.
Entrepreneurial families may only have one major liquidity event in their entire lifetime.
If they're serial entrepreneurs, they may go through that experience several times and they get better with each evolution of it because most times they start with they don't know what they don't know.
And their lived experience through the first one may suggest whether they ever want to repeat that.
It's interesting that Brendan and I can drip on the families over the years and say, hey, you need to prepare for this.
What is the ultimate solution? exit strategy, because we tell all families, you're going to exit your business one way or the other.
It's either by choice or chance or design or default, but it's going to happen.
And then all of a sudden it's like, oh, my goodness, how much do we have to, what do we do now? And we have a compressed timeframe.
I like to say that if we can get ahead of a transaction, I mean, this sounds a little silly, but three to five years before it ever happens, we can have phenomenal results, both quantitative from a planning and tax perspective, but qualitative because we know exactly where the dominoes are going to fall when that event happens.
It's usually the clients that get surprised by an offer out of the blue, and they haven't really thought through what this really means in that moment.
So getting them mentally and emotionally prepared for that is a big part of it.
The tax planning more often than not, regardless of our timeframe, takes care of itself.
Yeah, I'd say, you know, to that point, planning isn't really just about kind of controlling the future, controlling outcomes.
And the earlier you start planning, the more options you're going to have because, you know, they come up and somebody suddenly gives them an offer.
Before they know it, they're further down the path than they think before they finally reach out to their advisors.
And a whole swath of options are now off the table because of where they've already taken something to.
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