320: Conquering the Messy Middle – The Key to Startup Success

My biggest fear for anybody that takes my advice and decides to finally make the jump into a sweaty startup is that in 10 years you’ll wake up and have bought yourself a job. You’ll own a company that controls you, you’ll be working yourself to death, and you’ll have no way out. I call this the messy middle.

The messy middle is the time between starting your company and having a real operation with employees. My fear is that you get trapped there, and once you’re there it’s easy to get off track. Three years after I started Storage Squad, we were still grinding it out in this messy middle, and it was a mess. It took me a long time to get where I am now, but I’ve accomplished more in the past 12 months than I did in the 9 years prior.

Getting distracted by exciting new opportunities or by big online entrepreneurs can leave you stuck. I met with a friend who has a successful service company bringing in $2M in revenue and $400K in profit a year among three partners, but he’s on the road all the time still doing work for the business. He’s been unable to find a way for the company to grow without him being directly involved. Instead of setting up systems and processes to grow and take himself out of the business, he gets distracted and finds himself trying out something new and different on the side, losing focus of his business because it’s burnt him out. When you’re in this state, it’s easy to look at other successful people and convince yourself that you’re in the wrong business and you have to put your energy somewhere else.

As you make money, the amount of opportunities available to you increases, and it makes it hard to stay focused on your core business. Growing and scaling take focus, and distraction will only hurt your business. I know what I need to do in my career: I need to let time do its work while I tackle problems and do work that isn’t sexy or fun to make my real estate private equity company really big. What I can’t do is get distracted by things on the side that aren’t worth my time.

Avoiding distractions can be difficult because the key to getting early momentum is energy and excitement. I never would have started out if I wasn’t easily excited, but that same excitement can take you off your task when you start making money. At that point, you need to shift gears to stay disciplined and focused.

If you’re in the messy middle, your business is semi-successful but a load on your time and growth has been stalling, your job is not to say yes to new opportunities. Focus on what makes you money and double down on it. Once you have your money, you can start getting creative and saying yes to other opportunities.

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About Me

I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.