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20 Years Ago Today I Became An Entrepreneur…

As the second plane hit the second tower, I turned to the software developer sitting next to me and said “We’re at war.”

Of course, I didn’t know what that meant yet.

None of us did.

In some ways, we still don’t.

I thanked my lucky stars that day that my family and friends were unaffected.

Or so I thought…

In Boston, everyone knew someone who knew someone who had lost someone.

But at a gathering in New York I faced a harsher reality: they all knew someone who had been lost.

It would turn out that I would be lost too, though I didn’t know it yet.

I would lose my career, my circle of friends, my closest relationships, and the person I was.

In many ways it was the most important day of my life.

A phoenix rising from the ashes at Ground Zero.

Technology spending dried up, and the venture capitalists pulled back their money.

So on January 1, 2002 I found myself unemployed for the first time in my 12 year computer career.

And there were no computer jobs.

Oh, don’t get me wrong. I loved being unemployed.

I played the piano for two hours every morning.

I took long walks on the Minuteman Trail in Arlington.

I controlled my schedule in ways that had never been possible when I had been working.

Just one problem.

Running out of money.

No desire to move back in with my parents.

It turns out that I had always been an entrepreneur at heart.

I just hadn’t known it.

I remember my favorite phrase from my favorite boss:

“We’re delivering a product in 9 months. We don’t know what the product is, or what it will do, and we don’t have a team, but Andy’s going to be in charge of getting it done.”

We got it done, all right.

Best project ever.

But to take that approach with a business of my own?

No one is more surprised than I am that Mike Merrick convinced me to buy a window cleaning business…

But I’m sure glad he did.

People still look at me with awe at the risk I took.

But I had done my homework. And at that time, continuing my career in computers was riskier. Window cleaning was the best opportunity I had found to make the kind of money I wanted to make, and it came with the promise of a more flexible lifestyle.

I started hoping that I wouldn’t get a computer job, because I knew I wouldn’t have the guts to turn down a computer job, and yet I wanted to see if I could succeed at my own business.

Fish Window Cleaning sold me on the glimpse of a life I discovered while I was unemployed.

Not having to go to an office every day.

Creating time and cash flow to do other things.

Start a family.

ImprovAndy.

This, and you.

Now I make my living teaching and writing.

Thank you for inviting me into your inbox.

For sharing your entrepreneurial hopes and dreams.

For being on this journey together.

I loved working in computers.

I love this more.

I shed my old life 20 years ago today.

The single guy who was a serious computer geek now started, grew, and sold one business, owns a second business, attracted and married a woman who loves and inspires me every day, and has two beautiful daughters who keep me young.

That other guy is long gone.

My heart goes out to the victims and families of that truly dreadful day.

Because I lost someone too.

Me.

It was a long, hard road back to somewhere I had never ever been before.

A place I hardly dared dream of for myself.

It was the kind of day I would not wish on anyone.

And while I mourn the loss of the old me, I am thankful for what it has allowed me to become.

God Bless.

26 comments on “20 Years Ago Today I Became An Entrepreneur…

  1. Andy,
    Thanks for sharing your story of how your life changed due to 9/11. 
    I had wondered how you got to be so clever in all things digital – now I understand.
    I had wondered why you were in the window washing business – now I understand.
    I didn’t know what to write back to you in response to your very moving email sent out on 9/11/21, until today when a friend shared this video about this 9/11 tree’s resilience: 
    https://www.youtube.com/watch?v=Xcrt1MNSgFw

    1. Thank you, Susana, for posting such an inspiring video. I do feel a kinship with that tree. Maybe we all do. Much appreciated!

  2. Thank you Andy for sharing yourself. Like so many, if not then, later we met someone who lost her husband on AA 11. We also have two friends who were late to work and a meeting. Happy for your new life and new you.

    1. Thanks Marianne. The CEO of the web startup I was working at was booked on Flight 11 that morning. His contact in California moved the meeting later in the day so my CEO switched to a later flight and was at the airport when this all happened. I’ve never seen anyone looking quite as shell shocked as he did when he stopped by the office later that day.

  3. great Story! I was walking on the minuteman trail in Arlington as well around that same time! We could have passed each other! Your story gives me hope I can make a go of it. I just lost my job and need to focus full time on my business!

    1. I love stories about connections that could have been. I’m waving to you on the trail 19 years ago!

      Glad to hear you have a business to focus on. This too shall pass. Hang in there!

  4. Hello Andy, I‘m in awe of what you have accomplished, you definitely found your calling, I like your sincere writing style and I read your posts regularly.
    Best wishes.

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