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What's That They Say About Assumptions?

Serial entrepreneur Logan Lenz shares the story of how he learned humility by making decisions based on expectation instead of reality.

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My Great Mistake

Editor's note: Failure can be a beautiful thing. With the right attitude, an entrepreneur can take the message from what went wrong and turn it into something that will be right in the future. Portfolio.com has partnered with the Young Entrepreneur Council to offer real-world stories of mistakes and the lessons they produce. Come back each Friday for another column in the series.

I started my first business at 21. I had a huge ego, and, like so many other young entrepreneurs, I thought I already knew everything. Even worse, I thought I was immune from any type of failure. Boy, was I so wrong.

In my eyes, my first company was going to be a multimillion-dollar enterprise within the first year. I had the business plan and revenue forecasts to prove it. Looking for a seed investment, I turned to my small Rolodex and started unleashing my charm on some of my wealthy contacts in hopes of winning over somebody enough to secure a seed investment.

After the first two meetings, my excitement and anxiousness overtook me, and since I was so sure the outcome of receiving investment funds was inevitable, I decided to lease a very expensive corporate office downtown. With little to no revenue at the time, I was counting on the imminent investment, which I obviously had yet to receive, to fund the future monthly rent payments.

Having an office fueled my perception that I was unstoppable and, now, even more marketable. On top of my gorgeous business plan and high expectations for success, I figured others would see the office as a sign that I was already running a successful company. Who wouldn't want to fund me now?

Weeks went by. A few friends and I were working out of the office trying our hardest to create revenue, but by the time the rent was due, we had nothing left in the bank account to write the check with. My horrible startup decision started to echo in my personal financial struggles for the next few months. For the first time in my life, I felt like a failure. I realized, though, that I had made two crucial mistakes in this situation: I ignored bootstrapping as a funding option and underestimated how hard it would be to secure an angel investment as a first-time entrepreneur with little to no real-life experience. I had become the personification of what happens when one makes assumptions.

In the end, I was fortunate enough to find another company to sublet the office space before I could be forced to file for bankruptcy. Having to post local ads and hustle to find someone to take over the office lease brought me back to earth and made me recognize the importance of humility.

While the growth of my company was negatively impacted by my anticipatory decisionmaking, I can now look back and smile at my immaturity and inexperience. If I didn't make such a horrible mistake, I might still be the egotistical college student that thinks he's better than everyone else.


The author is a member of the Young Entrepreneur Council. The YEC is an invite-only nonprofit organization comprised of the country’s most promising young entrepreneurs. The YEC promotes entrepreneurship as a solution to youth unemployment and underemployment and provides its members with access to tools, mentorship, and resources that support each stage of a business’s development and growth.


Logan Lenz is a serial entrepreneur that owns and operates Endagon, Iced Tees, and Jiggy Piggy. He also blogs at loganlenz.com.

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