Your backup plan is the reason you’re going to fail

I’ve been an entrepreneur for over 20 years. I decided to start my first company in my dorm room with my college roommate, and have never looked back.

Toward the end of our first year of business (our company was called NBN Designs at that point, and we built websites) we found ourselves in New Zealand pitching a company to build a massive web portal . Up until that point, our largest website project was a $250 project for my aunt in Chicago. No joke.

Raj and me in 1999 pitching our big client in Queenstown, NZ. In our $50 suits :)

Somehow after a week of “pitching” we ended up leaving New Zealand with a $65,000 contract to build Queenstown.com. Again, no joke.

And we were off to the races. The first thing we did was quit our side jobs. I was coaching tennis during the day, Danny (our other partner) was waiting tables at night, and Raj was…well, Raj was traveling the world having the time of his life. When we won this project, we quit all of that and put our heads down on the business.

A few months in and we were making real progress, but our client had started to become unresponsive. And then I got the email from him that his business was filing for bankruptcy and he needed to cancel the project. The project that we had worked on for months, and that we had yet to receive a single penny for (we later learned that it’s smart to ask for some money upfront.)


As you can imagine, when this happened we thought our world was ending. It was devastating beyond comprehension. We no longer had second jobs to rely on and we were locked into a one-year lease on office space. Essentially, we were forced to be ‘all in’ on this business.

Looking back, this crushing moment ended up being the best thing that could ever have had happened to us. It is so incredibly hard to make a business work. The odds are stacked against you even if you put your entire self into the process. But if you have a Plan B, something that you can fall back on, then you’re making those slim odds even worse.

If you want to accomplish something great, you can’t have a back-up plan. You have to give it your all, every ounce of what you have, and I promise if you do that, you can accomplish anything.


A few weeks back I was thrilled to be interviewed by Sangram Vajre on his Flip My Funnel podcast, and we got into the concept of not having a Plan B, among other things. It was fun to share stories with him, and I hope you have time to check it out.

If this lesson of No Plan B was interesting to you, you might want to check out my book, The 5-Day Turnaround! It not only dives deep into that concept, but also other ideas that I believe will make anyone a better leader. Check it out!


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