How I Created My Own School

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I was doing some quick math recently to calculate how much I’ve invested in my personal leadership and entrepreneurial development over my lifetime. So far (I’m not done). 

What made me do that? 

It was a casual conversation that I overheard in the gym. 

One guy was telling another about a program he’d spent $2K to attend.  

“Two thousand dollars?!” the other guy said, as if it was a lifetime of money.  “Must be nice.”

“I think it was worth it,” the first guy responded.

“You’re crazy,” the other guy said before I walked away thinking to myself that if he thought the first guy was crazy, he’d think that I was nothing short of a lunatic.

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The first time I remember that I spent money on making myself better, I was in my mid-thirties, trying my best to run and grow an industrial waste service company I’d co-founded when I was 27.  I spent the money to join a CEO Roundtable Program created by our local business chamber group.

The cost was $500/year.  Even though the cost was modest, almost insignificant really, I dragged my feet for a few months before I wrote the check.

What did I get for the $500?  Access, ideas, camaraderie, meaning, and togetherness.


Although I’d never thought of myself as a CEO (CEO’s run huge companies like Amazon and Google, I thought), for only $500, I was now a member of a group of business leaders I, quite likely, would never have met otherwise:

  • There was Tom, the president of a large law firm;
  • And Anne, the founder of a marketing/PR company and an awesome entrepreneur;
  • Then there was John, who ran the Milwaukee office for a giant family-owned construction business.
  • And Dan, the founder and president of a dynamic commercial real estate brokerage.

I felt like I was out of my league, but I was welcomed by the group anyway.

Like an equal. Like I belonged. 

It was weird and cool at the same time. Energizing and confidence-boosting. It made me feel like anything was possible, that any problem could be solved, and that I could get value from and provide value to others. It was Powerful.

I stuck with that Roundtable group for more than 10 years, happily plunking down the jokingly low $500/year for an education and connections with (what I quickly came to believe and understand) successful people who cared about me as much as I did about them.

And I didn’t stop there.

In fact, I stepped up my spending on myself dramatically.

My thinking was that if $500/year could benefit me so significantly, spending more on higher quality coaching, training, idea creation, peer-to-peer counseling – and being around more and more successful people – would return the many multiples of what it cost, like interest and dividends compounding over time.

And more.

In all, between the ages of 35 and 50, I invested more than $200,000 in myself, in what became my own personal school.

By attending my personal school, I became the product of that education, improving as a leader, business person, entrepreneur, dad/husband, colleague, investor, communicator, value-creator, friend, boss, co-worker and cheerleader.

Oh, and there was another benefit to having invested in my own personal school.  The value of my business increased five-fold, thanks in large part to the lessons my education provided.


I’m sure that if I told that guy at the gym how much it “cost” me to go to my school, he’d think I was nuts, crazy. And I’d say, yes, like a fox!

When I began investing in myself, a different level of people, ideas and expectations became my world. Changed my world. Improved my mindset. Made me a bigger believer in me as well.

Want somebody to invest in you? It might be a good idea to show them how much you’re willing to invest in you.

If I was interested in giving advice – and I’m not – and you’re someone who’s interested in accelerating your growth, perhaps exponentially, I might suggest that you start designing and attending your own school.  You can start this anywhere – there is no reason not to.  Start small, like I did.  Just Start!

Start small, like I did.  Just Start!

Mike Malatesta

Mike Malatesta

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