Why a very “boring” and disciplined life is the best life

Business Buyer and Builder,

Time flies, isn’t it? It is already the end of the third week of 2026. We're going to hear more stories where more baby boomers decide to achieve liquidity by selling their life’s work to private equity.

Take a traditional business in the services space doing between $2-4M in EBITDA, which they’ve built over the span of decades.

Their life’s work, liquidity achieved, hopefully there was sound financial planning involved and they’ve put aside what’s needed for them and the family to live a good, secure life…

Homes, cars, boats, vacations, supporting grandkids education maybe?

Did they sell 100% of the business? This is where things get interesting…

The seller didn’t want them to exit fully, alignment, customer relationship pass off, etc. The seller is mid-60s, healthy, doesn’t want to play golf 5 days a week, and his wife doesn’t need him home 5 days a week:)

Rolled equity of 20%. Second bite of the apple here we come. 

With deep industry knowledge and expertise from the seller mixed with hungry young investment professionals in their early 30s, the mixture is a potent combo to take the platform to the next level.

And it makes total sense, if you think about it.

Kids are grown up…so what else do you do? At the end of the day, it’s about keeping your mind and body sharp, simply enjoying the game and the fruits of your decades of industry experience and relationships (contacts). At the trade shows you know everyone and can vouch for the new buyer, your partner. There is a defined time-line of the next liquidity event for you. 

Maybe we start seeing more such cases because private equity and independent sponsors are aggressive (for understandable reasons) and more owners realize it’s actually a great idea to capture necessary liquidity, roll equity with the right partner and execute over a defined window of time to the next liquidity event.

“The best years are still ahead.”

Doing this in your 50s, even 60s, together with younger folks who bring the energy and financial expertise…imagine that team/partnership fully focused and aligned over the next 5 years...

So THIS next exit could potentially be a life-changing outcome for all sides. I’m sure we’ll see more and more such collaborations.

(“I’m not working for myself anymore, I’m working for my grandkids”)

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Which all lead me to a conversation with a friend, an independent sponsor, whose partner is in his 50s and has a successful exit under his belt.

The conversation was on: “Seeing more young investors starting to set up partnerships with gentlemen 20 years ahead of them.”

First, there’s nothing new…

There is precedent here; to make my point, let’s look at extreme success examples we all know… KKR and Blackstone.

• KKR - Henry Kravis and George Roberts partnered with Jerome Kohlberg. Kohlberg was 20 years older.

• Blackstone - Steve Schwarzman partnered with Peter Peterson. Same here: Peterson was 20 years older than Schwarzman.

Think about this.

Imagine the confidence the older gentlemen gave the younger men.

While talking to my friend, I asked, “What does this type of partnership give to a younger guy?”

• Younger guys have worked on deals at another firm but never on their own.

• Reputation - they are now getting deals that younger folks are not able to get or even see.

• Older partners have industry expertise and relationships with vendors, customers, and even competitors.

• They know the value chain of the industry.

• They collapse timetables while younger folks bring the hunger and the capabilities of a 30-year-old.

To sum up:

The older partner who’s 10-20 years ahead brings credibility, legitimacy and relevancy.

And the younger partner brings deal making drive, execution skills, and, most of all, energy.

Could we sum up and say we’re entering a new era?

As private equity buyers are aggressive. Founders in their 50s are realizing they don’t need to retire.

So what they do and what I believe we’ll see more and more:

1.  50+ year old founders selling to PE

2.  putting a bit of hard-earned capital aside

3.  then they take what’s left -- and get back in the game teaming up with 30-year-olds to build their next roll-up or holdco

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It is so refreshing to have conversations with folks who go through all the possible setbacks, from losing deals to new tariffs (Canada), and still close the platform acquisition followed by 2-3 add-ons in the same year

Now running an 8-fig EBITDA portfolio like nothing happened.

(Episode already recorded. There are so many Builders in the $1-15M EBITDA space, grinders and overall tough people who despite obstacles, keep moving forward building great investment firms/companies.

I take my job very seriously, working hard to bring you more stories like this.)

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After all… The real game is staying in the game.

Lots of people obsess over exits.

Not too many talk about durability.

It seems that in order to create real wealth? You just gotta stay in the game.

1. Acquire well

2. Operate conservatively

3. Keep optionality

4. Avoid zero

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The older I get, the more I think about the following:

A very “boring” and disciplined life is the best life. Day in, day out… And I really am happiest when it is like that.

I saw Alex Backer, the founder of the SaaS company Hyros, posting the other day that therapy for men is waking up to build great things and crush your goals, then standing back every so often to be proud of who you are… and then resuming.

Having a set of business, personal and character goals. You pursue them. Then you hang out with your wife and kids, go to bed, and do it again.

It is so true because we’ve been discussing this exact thing for a long time, and this became even more true after turning 30. And if you look at some of the top private equity and hedge fund managers, and owners of wealth management firms in their late 40s, 50s, and 60s… that is exactly what they do. 4am alarm. Looking at the market, reading news, going to the gym, and then straight to the office. Long day at work. Evening: dinner with wife and kids, more reading, and bed at 10pm. Or, if someone needs more sleep, bed at 9pm. All to do it all over again the next day.

And you can see that people like this have won in life. You can see the energy, passion, results, and the smile on their face.

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Lastly… to keep going, or to pivot? That is the question… Not always, but sometimes.

I believe Todd’s story is a great lesson for many business owners who may struggle to grow their companies as they want to…

Should I sell, keep trying, shut down, pivot?

In Todd's case, they were 4-5 years into building their $10m per year adtech company, which led them to analyze their current clients and then realize there is a much better business serving flooring retailers.

They then acquired 8 companies and launched an annual flooring event with 500-700 attendees, creating a real MOAT and eventually selling to private equity in a nine-figure deal.

I hope you enjoy and learn a lot from this conversation.

Here are the links to Apple podcast, Spotify and YouTube.

That’s all for today.

Thanks a lot for reading and I’ll talk to you again very soon.

Take care,

PrivateEquityGuy / Mike Markus