How a Bad Boss, Boredom, and a School Crush Led Me To Entrepreneurship

bad boss entrepreneurshipI’m always fascinated by stories about how people decided they wanted to become entrepreneurs.  We always hear about the inspiring story, or the life changing event.  But, in most cases, it was a series of events and circumstances that all connected together to put the right pieces in place.

That’s my story, and I thought it would be fun to share it with you.  This starts back in 2009 when I started my first site, The College Investor, and hopefully it will give you some encouragement to start your own journey based on your own circumstances.


The Bad Boss

Looking back, I really think that it all started with a bad boss that I had but really didn’t even know it until looking back in hindsight.  This boss was terrible, but I was young, naive, and didn’t really know it.  The boss was bad because she wasn’t really a boss.  It was one of those situations where she would say things upward that derailed my career, yet I didn’t know it.  She would never give me feedback.  Then, her boss would stop by and ask me questions, and I’d look like an idiot.  Then she’d coach me.  Bottom line – it led to me being disengaged.  Talk about the triggers that make you want to quit your job.

The trouble was I didn’t want to quit my job, but I sure didn’t like it.  It made me look for other things to do to give me some enjoyment.

You have to realize that this was after I had received my MBA, and I was looking to do more.  The trouble was I was looking to do more at my current company, and that wasn’t happening because of my boss.  In turn, it led to boredom.



I was so bored!  I was making good money, but wasn’t achieving my career goals.  At this time, I was also engaged to my wife, and we were planning great things, but my work-life just wasn’t coming together.

Image the circles of your life: friends, family, work.  The first two were going 100%, while my work life was at 0%.  And the real problem was I didn’t really understand why it was at 0%.  So, in my search for entertainment, I went down the rabbit hole that was the Internet.  I knew I wanted more.  I knew I wanted to apply myself.  I’d been side hustling for a long time, but I was tired of the manual work and wanted something different.


My High School Crush

That led me to Facebook stalking people – not in the literal sense, but killing time online inevitably leads to Facebook, which in turn led me to looking up my old high school crush.  Turns out she was getting engaged!  Good for her!  Anyway, the guy she was getting married to was doing this blogging stuff.  I didn’t really know what it was about, but I clicked on his profile, found his website, and started reading.

Reading the site, it was essentially Pat Flynn about a year before Pat Flynn took off.  I think the guy was ahead of his time, and he’s sense moved onto other things online, but his site gave me a ton of inspiration.  I clicked his affilate link for hosting and got started on my first site: The College Investor.  My theme looked like crap, my content was terrible, but I was started in my online business and didn’t even know it.


Lessons in the Path to Entrepreneurship

The lesson I have to share is that your total experience is what makes you who you are today.  You can’t change who you are.  You are who you are – the sum of your history, your family, your life experiences, and more.  And that’s okay!  All of those things will lead you down a path that will get you to your end goal.

The thing is, at some point in time, you need to look up from the path, figure out where you are, and decide what you’re going to do – left, right, forward, back.  If you continue down the path with your head down, you may miss out.  You may not learn the lesson that was needed.  You may not be successful.

Entrepreneurship requires a bit of self-awareness that others don’t.  That’s thinking like an entrepreneur.  That’s key.

I’d love to hear your path to entrepreneurship to date?  Any fun stories to share?

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  1. Mine is mainly boredom! I am incredibly bored all day long.

    • You seem to have been moving really fast with your side incomes! Can you work on them during the day at work?

      I’m so bored at work, but I can’t access the outside world during the workday.

  2. For me it was boredom and not liking the people I work with. Making 6 figures was great but I wanted more and it couldn’t come quick enough. Talk about the new boyfriend – Pat Flynn – small world! I agree Pat seemed ahead of his time. A lot of people are still not believers of making money online.

  3. It’s amazing to think that things in the past have lead you to where you are right now. Thanks for sharing your story.

  4. Great headline, great story!

    There’s not much worse than being stuck in a job where you’re uninspired and understimulated.

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