In our first few months I made more than 500 cold calls, scheduling only 35 sales meetings. At each of those 35 meetings I was rejected. Yes, at every single one.



The frustrating part was that I was selling against Big Six consulting firms that had never done a full Windows implementation before. On these sales calls, I was competing against men in their 50s, men in suits, men representing companies that were considered "safe."

And there I was, in my 20s, a total nerd, fresh from Microsoft. I had worked on the Windows engineering team. I had years of relevant engineering experience, and my staff had even more. But the sales prospects chose the competition over us every time.

New Kids on the Block

I kept hearing wishy-washy reasons as to why they wouldn't buy, such as "I need to check our budget" and "We haven't worked with your firm before." Actually, what they were really saying was, "You're not in your 50s, you don't have gray hair, you're not with a huge, well-known firm, and that makes us uncomfortable."

After the 35th failed meeting I told myself, enough already! It was time to evaluate what I was doing wrong. I asked myself: What does my business stand for? I knew the answer cold: We delivered the highest quality work possible on time and on budget, we provided outstanding customer care, and we had solid engineering expertise. I had made my brand clear to our earliest tech clients, but now it was time to make it clear to their larger counterparts as well as prospects in other industries.

I decided to stick around and spy on the successful guys after my most recent rejection. Positioning my car near the building's entryway, I sank down in my seat and hid behind a newspaper as they walked out. As they passed by my car, I lowered the newspaper and stared at them. What did they have that I didn't?

They had glasses. They had wedding bands. They had navy blue suits. Their look said: "Hire us and your head won't roll." My look said: "Want fries with that?" Could my sales challenge be as trivial as my looks? Could it be that the prospects simply couldn't get past this stumbling block?

Look the Part

Sitting there in my car, I declared this stumbling block a stepping stone. I drove to the nearest mall and bought a fake wedding ring, non-prescription glasses, and a navy blue suit. Voil?! Now my look made potential customers feel comfortable.

When you're early in the game, trying to make it all happen, you have to realize that sometimes you just have to look the part to feel the part. It's just like declaring victory as you step onto the battlefield.

It's what we do as entrepreneurs: We act it until we are it. I had seen myself as a dweeby engineer. To take my company to the next level, I had to see myself as a CEO worthy of selling to the Fortune 1000. And I had to back this up with the right look.

Starting with the first firm that said yes after I looked the part, we went on to build a client base of 700 of the Fortune 1000. We went back to the companies who'd rejected us earlier and closed deals. When you come across stumbling blocks, resolve to turn them into stepping stones, whether in sales, financing, or management scenarios.