7 Years Later: Leaving Wall Street to Buy Small Businesses

searcher profile

February 03, 2022

by a searcher from Brown University in San Francisco, CA, USA

Since 2015:

* 7 platform companies acquired

* 450 employees

* ~30 total acquisitions (lots of tuck-ins)

Not bad for 7 years work.


I'm talking about Chenmark:

Chenmark is a holdco founded by a trio who left Corporate America to buy small businesses.

2 of the 3 co-founders came on Acquiring Minds this week (find it in your podcast player or on the website).


My 3 fav takeaways:


1/ The size of business you choose to buy is a personal decision.

"Don't let anyone tell you there is a single correct size of business to buy."

A quote from Palmer Higgins, who noted that when they started in 2015, search was smaller than it is now, but even then there was a supposed Right Way and Wrong Way to buy small businesses, and they were definitely doing it the Wrong Way.


2/ But they were right.

(My words. The Chenmark guys don't gloat.)

But seriously. Like good investors, they had a thesis around the Chenmark project.

They poked and prodded their thesis, and most importantly they did some heavy introspection.

Do they actually WANT to spend a career running small businesses??

7 years later, yes and yes.

Yes, the napkin math of acquiring, growing, and holding small businesses doesn't lie.

This is a very real path to very real wealth.

And yes, they DID want to run small businesses.

Let me elaborate on that in takeaway #3...


3/ The founding thesis of Chenmark

It's a 2-parter:

1) The financial. Does this path pencil out? Very much so.

2) Life would be more interesting running small businesses than sitting behind a desk in a tower on Wall Street.

This second part of the thesis was highly personal. (love it)

Would they forgo intellectual challenges? I mean sure Wall Street can be lame, but it IS filled with high achievers at the top of their game.

And what about the dreaded...managing PEOPLE?

They liked this, embraced it.

Palmer acknowledges the personnel headaches, but talks about how gratifying it is to work with people and have an impact on their lives.

And as a small business owner you do this every day — and it's powerful.

As for the loss of intellectual stimulation — not true.

Sure it's different than competitive White Collar Land, but it's absolutely intellectually stimulating, and actually requires broader range.

James characterizes this as breadth (small business) vs. depth (Wall Street).

And lastly... a bonus - my favorite quote of the episode.

From James Higgins:

"The tricky thing about trying to build a holding company that owns a lot of small businesses is the first thing you need to do is move to Maine and buy a snowplowing business."

It ain't glamorous folks!

(at least not at the beginning)



Palmer & James Higgins of Chenmark

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commentor profile
Reply by a searcher
in Alpharetta, GA, USA
I did the same thing after 20 years on the Street - bought a commercial cleaning business 3 years ago and am closing on my second acquisition next month.My experience is almost identical to theirs in most ways.Their 2 part thesis is all you need.It ain’t rocket science, you just have to go for it.

And to Brian Cramers lengthy (and somewhat weird) critique - how many businesses has he run and operated?Probably none, like 90%+ of “advisors”.Seems like he’s selling something.

I can only say that I love managing my business.I love the nuts and bolts.I love the chance to help people develop skills and earn more so they can improve their lives.I love serving my customers and having them be grateful and come back on the next one.And yeah I love the freedom and free time but I can always dial that up or down.

After my first acquisition was “fixed” I had so much free time on my hands that I felt bored, restless.I had it made!But.One can only play so much golf and spend so much time with the kids.That’s why I am buying another one and I plan to do so every few years, or more importantly every time I see something that I like at the right price.

Good luck to all.
commentor profile
Reply by a professional
from University of Akron in Charlotte, NC, USA
Their purpose was good but I can tell by the acquisitions they made that their results would be something I would advise to avoid.For me, the Purpose is what I like to call a "Perpetual Wealth Machine". and the main driving force of the machine should be a business ownership in the form of what I like to call a foundational Passive Income Engine,.It's hard and more expensive to buy Absentee businesses but you should focus on businesses with higher Operational Viscosity or ones where they are easier to operate without as much built in friction and thus more easy to transform into a passive incoming producing asset.ROI for me isn't just about money/capital...it's also about time.your time is valuable and so the best calc of ROI is to include your time and stress.With 3 landscaping companies alone, I am sure the organization operated with a tremendous amount of stress and friction.Just going out and buyingalot of small businesses is setting yourself up for failure and living hell...I am sure you could probably acquire 1 foundational, high viscosity business to equal the cash flow from all the acquisitions they made.
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