Why I am going to lose thousands of dollars (and how you can avoid doing the same)…

My grandfather used to say, “The best wit bought wit.” Well, I just paid a lot of money for some wit.

About 3-4 years years ago I invested into a business that an acquaintance had started. There was lots of enthusiasm from him and his partner. I was shown spreadsheets with bold predictions. Pro-formas. Powerpoints. Everything looked great. Get in while you can. The sky is the limit!!!

I remember my gut telling me not to do it as I stroked the check, but I also remember telling myself (or lying to myself) that this was different. Surely these guys knew what they were doing. They had put so much energy into the business already, had made a compelling case, had … well, basically, they had done everything differently than how I would have done it, and I guess I was hedging against my own better judgement. “Maybe they know something I don’t,” I told myself.

Well, they didn’t. And now I’m learning my lesson. Or being reminded of a lesson I already knew but temporarily decided to ignore. You see, these guys didn’t talk about building their business one customer at a time. Or about creating a profitable, enduring business. Or about having a narrow focus and dominating their niche. Rather, they shot out Facebookian projections and used words like “viral.”

Look, I don’t know everything about business. Far from it. I learn something new every day. But in my years I have learned that while the media glorifies companies like Google and Twitter and Facebook and Groupon, those companies are tiny exceptions. They are outliers. Blips on a radar.

Yes, the people that started those companies had great ideas, and, yes, their solutions “went viral,” (I can’t stand that word now). But they got lucky and they are not the examples you should focus on when building your company or when investing into a company or when deciding to take a job at a company. It’s like playing the lottery. Sure, one in a million people will win big, but the other 999,999 people will lose their money.

We’ve built Schedulefly the least risky, most rewarding way. We’ve rolled up our sleeves and chipped away. One. Customer. At. A. Time. We have never expected it to blow up overnight while we kicked back and slapped fives and watched the customers flooding in so fast that our servers crashed. By the way, that’s another media-glorified badge of honor: “They grew so fast so quickly that their servers crashed!!! Wow!!!” I think it would suck if that happened because it would mean the people that pay us their hard-earned money wouldn’t be able to use our site until we got our servers running again. But I digress.

Most successful companies didn’t shoot out like a rocket and soar to space. Most successful companies started like a steam engine leaving the station. They took time to get going. Can’t you just see it:


Those first few “clicks” happened over a few years. Not a few months. Or weeks. Or days. And surely not overnight.

So if you ever have a chance to be a part of “the next great thing,” (as a partner, an investor, or an employee), be careful. Very careful. Because you may very well end up investing your money, or time, or both into somebody else’s attempt to win the lottery. Could you win? Yes. Is it likely you will? I bet not…


P.S. I don’t mean for this to be a pity party and I hope it doesn’t come across as pessimistic or negative. I’m o.k. with the loss. C’est la vie! Just wanted to put this out there so that perhaps at least one person will read it and benefit from it.