The 10 Biggest Mistakes My App Development Company Made in Our First 10 Years in Business

You learn by making mistakes. Hopefully, my experiences can help you avoid some of the hardships we had.

Ten years ago, on October 14, 2010, right before I graduated college, I went to Boston City Hall, paid a filing fee and registered my company, Yeti, LLC. 

I soon brought on my business partner, Rudy Mutta, and now, 10 years later, we’re still in business and, despite Covid throwing us some major curveballs, growing.

We are a bootstrapped service business, so compared to some of our peers in our hometown of San Francisco, we can really only claim modest success, having never IPO’d or become a billion-dollar unicorn. 

Looking back on our decade running this business, we’ve had the highs of being in a Netflix documentary, building high profile apps with top-tier clients and making it into the Fortune 5000. But, what you don’t hear a lot about from entrepreneurs is the mistakes they’ve made.

As we look back over the past decade, those mistakes are the moments when we learned the most. So, instead of touting 10 years of triumphs, I thought I would share 10 of my biggest mistakes and the lessons that came out of them. Knowing very little about running a company 10 years ago, I could have saved myself a lot of time, money and energy knowing these things.

1. The taxman cometh

In our first year of business, we thought it would be wise to show just how profitable we were. We even made sure we cashed a massive check from a client at the end of December to close out the year with even more earnings. 

We didn’t realize that no one really cares about your profits at this stage, but the taxman cares that you pay what is due. 

Not having kept track of our expenses properly, not paying monthly or quarterly taxes and not saving adequately left us almost completely decimated after our first year. 

In hindsight, it would have been hugely beneficial to understand some of the basics of business tax going into this venture.

2. The world is not flat

When we started our company, we got really excited about the idea of keeping our organization completely flat, where everybody had the initiative and self-organized to hit company goals. This works when your company is six people, but as it grows, it becomes impossible.

Reflecting back, I think it was because I was scared of doing the work necessary to be a leader. I had one business coach eventually tell me, “It sounds like you are trying to operate a pirate ship.” That might sound fun, but in actuality, pirate crews don’t perform very well.

Leadership is an artform that is important to study and practice — you can often give people more freedom and job satisfaction by providing them with a structure to do their best work.

Read more: https://www.entrepreneur.com/