Inside Running a Start Up

Many of you know that a little over a year ago, Chris and I founded an edTech startup with our business partner, called ClassMax.  I created ClassMax because I needed a tool in my classroom that didn’t exist.  I made a modified version of it myself by taking an existing product and modifying it as much as I could to do what I needed, but it wasn’t enough.  I came home and told Chris that I was really close to having a product that would be a tremendous help to teachers and that I thought maybe we should consider running with the idea.  Within six months, we had formed a company, hired full-time, professional web developers, and had a viable product up and running, for less than $100,000 (which is really inexpensive in any kind of software development).  By our one year mark, we had over 1,000 teachers using ClassMax in 43 states across the country.  We were doing great.



And then our money ran out and it was time to take the next big leap into the world of venture capitalists.  As far as I can tell, this is one of the biggest differences between running a start-up and owning a small business.  In the technology world, you need massive amounts of money to be successful at the beginning, and this doesn’t come from customers because you can’t build your product without the massive amounts of money.  That happens to be one of the many things our partner, Nick, brings to the table for us.  He works in the startup world full time and so he knows more about raising money than Chris and I do in this area and he has been super helpful as we move through this process.




No one told me that the name “start up” was really a big, fat lie.  What the industry should be called is “start up, stop, start up, stop, start up.”  We have taken the company as far as we can on our own dime and with one round of funding and now we are in the holding pattern until we get another round of funding to help us move forward.  And that part is about as difficult as waiting for the sun, moon, and stars to align perfectly because…

  • A customer wants all the bells and whistles.
  • But you can’t provide all the bells and whistles until you get more funding.
  • But an investor doesn’t want to fund until you have customers.
  • And a customer wants all the bells and whistles…

Are you seeing where I am going with this?  It’s like a chicken and an egg.  But let’s add in another really stressful part of working with investors…  None of them want to be the first to invest.  Remember when you were in middle school and your parents dropped you off to the dance or party or some other social event before anyone else was there and you just stood there like an idiot because this was before cell phones and so you literally just stood there, staring around the room?  Yeah, well, investors must have been scarred by these kinds of events because they are TERRIFIED of being the first to invest.  So, here’s the answer you get, “I’m in for xxx amount of dollar, but only if you raise xxx amount of dollars first.”  The result is that we have pockets of money everywhere, but NO CASH.


Which means that e’rryday we be hustlin’ at ClassMax.  Chris, Nick, and I have pitched so many times, you guys.  And it’s just like what you see on Shark Tank.  We usually get in front of 2-4 investors at a time and the meeting is unofficially hosted by our financial coordinator (basically like a stock broker for investors and companies).  He introduces us around the table and then we take off on our pitch – just like what you see on Shark Tank!  We tell them how much we are asking for, what the issue in education is, what ClassMax solves, we go over our business plan, our numbers, our staff, and then we show a demo of the product.

Over and over and over again.


And you might think that if we are doing this so often and no money has come in, then we have failed.  And that, my friends, is the hardest part of the whole darn thing.  You have to keep going.  You just keep on going.

Because you haven’t failed until you stop.

I learned that with my book deal and my glory days in my blog.  Do you remember that time?  It was probably four or five years ago, maybe more.  I had an agent, a book deal, and life was cruising with my blog.  But the deal we were brokering wasn’t the exact image of the kind of book I thought I wanted to write and so I pulled the plug and then fired my agent.

Talk about learning a life lesson about pride.  Man.  Pride very literally goes before the fall and I fell hard from that one.  Bruised my ego and basically lost my Marriage Confessions income.  That one hurt, both personally and financially.


So I am very mindful of that experience as we move through this one.  I’ve given up the pretense of being successful every day.  We are not.  We are unsuccessful lots of days.  But on some days, we are very successful and those are the days that keep us moving forward.  And I think that shift in my perspective is what separates successful companies from failed ones.  If I gave up right now, if we packed it all in and said, “Well, that was expensive and stressful,” if we emailed all of our users and said, “Sorry, guys, we’re closing up shop” that would be a failure.  We would learn and move ahead, yes, but it would still be a failure of a business.


But if we keep pushing, keep talking, keep working, keep hustling, then we aren’t failing.  We are just succeeding… very slowly.  But slow forward progress is still progress.  And so, we keep trucking, knowing that we have a product that will change classrooms and instructional practices on a grand scale.  Knowing that we have teachers who recognize this.  And knowing that all it takes is one phone call for our world to change.


I try not to blog too much about ClassMax because I don’t want to take advantage of my readership.  Who wants to check in to a blog for a funny, lighthearted story about kids or pets or something only to find a sales pitch?  Also, sales pitching is the WORST and I would never do that on my down time.  I barely do that when I have to!  But ClassMax is a huge part of our lives and it feels weird to not share what’s going on in that area.  And, personally, I tend to work through ideas and struggles and challenges here on my blog as I write about them, so it’s helpful for me to flush through ideas here.  Don’t worry.  I won’t do it often because nothing is more boring that business.  But I hope you’ll let me air out my thoughts on ClassMax every so often, so that I clear my head and refocus myself.

I’ll pay you back tomorrow with a post about how Chris drove me insane this weekend, I promise.  🙂


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