255: The Hardest Part of Building a Successful Startup Company – The Messy Middle

In this episode of The Sweaty Startup, I’m going to share what I feel to be the hardest parts of building a successful startup. I feel it is essential for any entrepreneur to go through this trial by fire; and, it is how well the entrepreneur handles themselves through this phase that determines their long-term success. What is the hardest part of building a successful startup? It’s the “Messy Middle.”

Let me explain:

My fear for any entrepreneur that starts a business, for YOU, is that after building a company from the ground up, you wake up at 40 or 50 years old and all you have is a job: You have a company that controls you, you have no way out, you have no real enterprise value, and you’re working yourself to death. It doesn’t matter that you own the company, what you really have is a job. 

Now the sad truth is, most entrepreneurs get carried away in their business that they become just another small business struggling with the management of their company always reaching for more but never quite able to attain it…all because of what’s going on in their Messy Middle: the time after you start the company and before it becomes a valuable entity with employees and systems. 

There are many things that can send you off track once you are in this Messy Middle. One of them is listening to guys like me: entrepreneurs who started a company ten years ago, worked their way through the mess of managing their business, and harvested some degree of success. I’m not saying stop listening to me or other successful entrepreneurs. I’m saying don’t allow yourself to get distracted by the things they are doing. Learn from them, but stay focused. It’s really easy to look at people doing big things on the internet and think, “Oh, my God, I got to do something different.” 

This is the big entrepreneurial distraction that is ‘The Media’. 

Let me clarify:

The other day, I met with a friend of mine on Zoom who lives out in California. He and I went to College together and, like me, he also became an entrepreneur. He owns a really successful service company that makes around $2 million a year. The problem is he’s on the road all the time, and he’s working his hands down to the bone. They have good people and built good systems for some of the workers who transact on the ground, but he’s been unable to find a way to grow his company and go to that next level…that is, without him having to be there to manage it.

Instead of doing the work to standardize a system that delivers a product and grows on its own to take himself out of the company he gets distracted. He is always trying something new, going for that sexy thing that could be the next breakthrough product.  When that happens, he loses focus on what he should be excited about: his little old, sweaty startup that now generates $2 million a year. 

The focus for him should be building out systems, making those quality hires, and growing the company. Instead, his company has completely burned him out because it relies on him managing the business for the day-to-day. The company has lost the shiny feel it had when it was a new small business startup. It isn’t fun and exciting to him anymore. He’s stuck in that Messy Middle.

 So what do you do when you’re in the Messy Middle?

Keep your main thing as the main thing. What kills a lot of entrepreneurs is that once they get a little bit of momentum, they start to get sidetracked, distracted, at new opportunities and they mess it all up. They lose track of what was the foundation of their business, losing sight of the main core of their sweaty startup. They allow themselves to get distracted from the product or service that made them take off in the first place. Growing the business to that next level takes focus, and it can be done quickly if you do the right things. But many entrepreneurs aren’t willing to do the real hard things the boring things:

Sure, the key for you as an entrepreneur in your startup, in that beginning stage, is to get that fire and be excited. But as you begin to learn and gain momentum, when things aren’t fun anymore, the key is to develop discipline the discipline of saying “no”:  Say “no” to new opportunities. Say “no” to new things that will distract you.  Say “no” to the next big thing. Early on, it is vital for you to do the truly hard thing of building systems in order to scale yourself out of a “job”. Build systems that allow the company to run without you managing the business day-in-day-out.

So right now, if you’re in that Messy Middle and you have a business that is semi-successful and needs to be taken to the next level, your job is to take the main thing, that one thing that you found to be most profitable, and focus on that. Even if it’s not fun, even if it’s not sexy, keep your main thing as the main thing. Say “no” to the rest. Learn to make money and build systems around your main thing. Scale yourself out of managing the business, out of a job.  Then, when you have this type of momentum, that’s when it’s time to start saying “yes” again. That’s when it’s time to start having fun outside of your main business, that’s  when it’s time to start going out and meeting people. But for now, do the real hardest thing in building a startup: focus on what you are doing in the Messy Middle.

Three Key Takeaways:

  1. Don’t allow yourself to get distracted when you are in the ‘Messy Middle’ of building your startup.
  2. Develop the discipline of saying “no” to new opportunities that will keep you from the main thing that started your company’s growth.
  3. Scale yourself out of managing your business by building systems that allow for growth without you having to be there.

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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.