June 9, 2012

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Bootstrapping a startup from three to 30 people — and counting — has without a doubt, been the most challenging thing I’ve ever done in my life.

While it’s extremely rewarding, nothing really prepares you for the emotional ups and downs, organizational challenges, and on-the-fly decision-making required to have any degree of success when turning nothing into something.

With that said, here are three pieces of advice I received that have stuck with me and my team since day one:

1. Watch out for the most dangerous 4-letter word in the dictionary.

These words of wisdom were given to us prior to starting by Russ Fradin, the very successful founder of Adify. He noticed that we were using the word “just” a lot:

“If we just close a few clients and just buy some search campaigns, then we’ll be generating revenue in no time!”

Of course, we didn’t understand until about six months in, when each of our “justs” took twice as a long as we expected and were four times more challenging. Today, it’s a mantra we live by internally: There is no such thing as “just.”

2. You don’t know anything until you’ve actually done it.

Coming from backgrounds in consulting and finance, our team members were experts at building fancy Excel models with amazing projections. “Buy this many clicks, have this percentage of users convert and only 5 percent market share, and we’re billionaires!”

It all made perfect sense as we analyzed and projected … until we actually did it. Then, we purchased clicks at three times the price we budgeted, converted a tenth of the users we projected, and realized that 5 percent market share was actually made up of hundreds of thousands of transactions and sales that needed to be closed.

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