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March 27, 2025

The Jazz Band and How It Relates to Business

Welcome back to the Mid Market Insider!

Today’s newsletter edition is about one of my favorite topics, the jazz band, and how it relates to having a plan in business (or not having one).


Most founders and business owners would love a clear, well-defined plan.

Right? Imagine if you had a clear roadmap to reach your business goals and the steps were laid out right in front of you.

I think we can all agree that’d be nice.

That plan can be compared to a symphony:

  • Everyone has their parts

  • They play at the same time

  • There’s a conductor

And…

If one person misses a note, the performance is ruined.

Okay, a bit dramatic there at the end, but you get the point.

People would love to have a clear roadmap, especially as they get close to selling a business.

But, unfortunately… It doesn’t really work like that.

I’m no expert on jazz, but how I think of it is you have a basic prompt and go with it — somebody adds something in and you have to adapt. Things happen and you have to just go with it.

You could start with the same opening riff 5 days in a row, and every day, it’s going to sound completely different.

When it comes to selling your business, how it actually works is there’s an idea of the destination (directionally accurate, maybe not), and you head towards it.

But none of us can know exactly where we’re going to end up — that’s just part of running a business or going through a sale process.

At one of our portfolio companies, we made a strategic decision to pursue a complementary line of business.

It was easy to understand who the customers were and what types of goods and services we would need to deliver.

However, the internal capabilities to not only deliver these goods and services but, perhaps more importantly, be able to win the work from new customers was far from certain.

We had some work to do…

To successfully add the new line of business, we needed new equipment and people with different skill sets.

We hired the minimum number of people we needed, bought used equipment to minimize capital outlay, and tried to test as much as we could.

Years later, the business has transformed the entire company and has become the bigger line of revenue for the company.

Hindsight being 20/20, we should have done it sooner.

My point is from above…

We didn’t really have a plan when we decided to move forward.

Today, the entire business doesn’t look exactly like what we thought it would — and it’s grown faster than we thought it would.

💡 Quick Tip:

Takeaway: While a clear, well-defined plan sounds ideal, the reality of running a business—especially when selling—is more like jazz than a symphony.

You start with a basic direction, adapt as things change, and realize that success often comes from being flexible and responsive.

In the end, businesses may not look exactly how you envisioned, but the unexpected growth can exceed your initial expectations.


That’s all for today’s newsletter! Thanks for reading!

📅 Next Week:

Next week we’re going to be discussing the dangers of rushed growth and why you should focus on “strategic pacing” instead. You won’t want to miss it. Stay tuned…

Keep building,
Nick

P.S. 

If you want to hear more from ‘The Most Boring Guy In Private Equity’, follow me on LinkedIn and YouTube. I dive into the world of private equity, share some tips and tricks for small business owners, and most importantly, share my industry knowledge.

Make sure to follow me so you don’t miss out!

If you want to discuss your business goals in greater detail book a discovery call: https://calendly.com/nickmclean/discovery-call. 

Just remember, this won’t cost you a dime and you get what you pay for :)

I just launched a podcast, Ambition with Nick!

Links can be found here:

Apple
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LinkedIn: Nick McLean
YouTube: NickFourPillars



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On the Ambition podcast, hear firsthand accounts of the challenges, risks, and rewards of transforming businesses from mom-and-pop shops to complex enterprises.

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