Let Me Talk You Out of Being an Entrepreneur



A short, two question quiz might just save five years of your life (and a hell of a lot of pain)

I reached for my beer and tried to think of how best to respond to the question that was just presented to me by an aspiring entrepreneur. A warm breeze was blowing, and we were sitting outside my favorite meeting place in all of Austin: The Mean Eyed Cat. Part dive bar, part Johnny Cash museum and part BBQ joint – The “Cat” has a lot to offer and provides a super casual setting to have real conversations with entrepreneurs.

“So, can you think of any reasons why I shouldn’t start this business?” she asked after finishing the short summary presentation.  

The question Sarah put forward was the right one and the hardest to answer. She had reviewed with me her latest business idea, filled with market information and data to support it.  .  

The truth was I really didn’t know what to think. The idea was solid, the data supported her value proposition and the existing competition didn’t seem strong. Plus she had direct experience with a similar business so on paper it should have all lined up. But there was still something missing that I struggled to put my finger on.

Finally, after a very long sip (ok, gulp) of beer, I mumbled the one question that kept running through my head.

“What do you think is missing?” I asked quietly.

“What do you mean?” Sarah asked. “Was there something missing in the analysis or did my market size not get you excited?”

“It’s  not that,” I replied as I struggled to get my thoughts together. Finally, I asked the question that was really bothering me, but yet I couldn’t articulate effectively. “In five years, if this doesn’t work, will you still be passionate about running this business? Are you really willing to give up five or more years of your life pushing this rock uphill if it doesn’t go as well as you think it might?”

Sarah looked at me with something between anger and relief.  Then she took a slow sip (or gulp) of her beer and leaned back on the wooded picnic table that served as our conference room table. After a few minutes, she shut her laptop and stated with no hesitation “No. I would be pissed and feel like I had wasted a bunch of time on a shitty idea.”

“That’s your answer,” I replied quickly. “Entrepreneurship is so damn hard that if you are not completely, passionately committed to the mission you are trying to accomplish, then your chances of success go down dramatically. I just don’t feel the energy when you talk about this idea.”

“Well, if you have time for one more beer, can I run a completely stupid idea by you?”  Sarah asked optimistically. She sheepishly opened back up her laptop and brought up a presentation she had been hesitant to show me. As she flew through the materials I watched her passion, enthusiasm and energy increased dramatically. She didn’t make it half way through the presentation when I raised my hands in mock surrender.

“This is the business you need to start.  How much do you need to get going?” 

The idea was a good one but not dramatically better than the idea we had discussed 20 minutes earlier, but on this one the energy, passion and commitment were all obvious. It was clear her focus was at a much higher level for this idea and I quickly got the sense that she was going to make this her life’s mission. 

Entrepreneurship is so stinking hard and most entrepreneurs radically underestimate just what lies ahead when they get started. In some regards, ignorance is bliss. Had I known how hard it was to do, I would have never taken the step myself. However, there is a difference between starting something without thinking through every last risk (if you did that you would never take the leap) and making sure you know exactly what you are getting into and preparing accordingly.

The story of Sarah is a real one, and she is now running an amazing startup in Austin that my firm Next Coast Ventures is proud to have funded. One key point here. This is NOT about following a passion – I think that alone is dangerous thinking. 

For entrepreneurs, the key is to have a solid idea and strong value proposition that YOU (as the entrepreneur) are ALSO passionate about. 

The difference comes down to commitment, energy and focus. It doesn’t guarantee success but it sure increases the likelihood.  

When I talk to an aspiring entrepreneur, I ask them to do a couple of things BEFORE they get started.  The goal isn’t to discourage them but rather to make sure they are really ready to jump into the pool.  In my book Mr. Monkey and Me I call these “Monkey Minders” and they show up at the end of each chapter. Here is my short two question test to make sure you are ready to jump into the pool:

  1. Let Someone Talk You Out It Test. Go to someone you really respect, tell them your idea and beg them to talk you out of starting the business. Listen to all the reasons why your idea is dumb or why the business will fail and see how it changes your conviction level. Once you found one person to tell you not to do it – find five others to do the same. Then see how you feel.  Are you deflated and depressed OR are you even more convinced that you are going to prove them all wrong? 
  1. Next Five Years Test. Like the question I posed to Sarah, this one gets to the sustainability of your idea. At Next Coast Ventures, we see so many entrepreneurs who have a pretty good idea, but we can tell that deep down they aren’t passionate about the business. Even the best start-up ideas will be hard to get off the ground – without real passion around the idea, the hill becomes that much steeper to climb.

The good news is that these two questions are really simple and are designed to test the very core of your commitment and energy around your idea. If you feel your energy or commitment level waning after the test, this could be a very real warning sign.  The ups and downs of starting a business, regardless of size, are all-consuming. That needs to be your expectation.  If you start to waiver on either of these questions that is a good thing —you might have just saved several years of pain.  This is why I created the Entrepreneur Survival test – a tool for entrepreneurs to evaluate their grit, passion and commitment to making their dreams a reality. Take it, share it and utilize it to see where you stack up. 

If your idea “fails” these tests it doesn’t mean you shouldn’t be an entrepreneur.  It might just mean that your idea needs more time, research or shaping. The real moment comes when you start to wake up and your idea turns from a “maybe I will” to “I have to do this”. Once this happens, the first step of your journey will have already begun. You will be ready to jump in the pool regardless of what comes. 

The first step is the hardest but with that step comes something called momentum.  Momentum brings progress.  Progress can turn into destiny.  This mindset has the power to change lives — starting with yours! 

Don’t miss future blogs – sign up for my Entrepreneur Survival Guide here.

Monkey Masters: Jason Dorsey

Monkey Masters: Jason Dorsey

For my third interview of Monkey Masters, I am thrilled to interview Jason Dorsey.  Jason is one of the most interesting entrepreneurs I have ever met and his insights, experience and background are truly exceptional.  The list of Jason’s accomplishments is too long...

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