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15 Lessons I Learned Over 15 Years as an Entrepreneur

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by Patrick Dillon / From Our CEO, Management

September 9, 2022

  • 3 min read

My entrepreneurial journey began at a young age—I was lucky and knew this was the path for me. I started my first business at 12 and hired my first employees at just 14. However, it wasn’t until I was 27 and moved to San Diego to start my first real company that my real education began. Since then, I’ve started around ten businesses and currently own and manage three companies.

Owning a business is perhaps one of the most fulfilling activities one can pursue, maybe in line with being a parent, as many often compare the two. And just as being a parent the first time teaches one a lot of new skills, so does becoming an entrepreneur. Here are some of the most important lessons I’ve learned in entrepreneurship.

1. The work isn’t just about running a business.

In a big way, it’s also learning about yourself. Over the years, I’ve found the truly happiest people have been the ones that have spent a lot of time working on themselves.

2. Have a sizable starting nest egg.

And not just for the business, but for yourself too. This will allow you to focus on doing the right thing and not sweat the small stuff in the beginning. Sometimes that means raising money and not going into a new business strapped for cash because it’s easy to give up when pushed to the edge, which is omnipresent in most cases.

3. Focus on profit.

Without it, there’s no point and no chance it will work long-term. Get your bookkeeping in order in month one. You’ll thank yourself soon enough.

4. Support your people.

As a business owner, you are there to support your team, not the other way around. Unfortunately, I’ve had two partners in past businesses who either didn’t believe in this, or didn’t live by this. I don’t work with either of them anymore, and both have had a string of failures since.

5. Create a bullet-proof hiring and training strategy.

Put way more thought and energy into your company’s hiring and training programs than you think is necessary. Hire Slow; Fire Fast is a mantra anyone in management should learn to live by.

6. Never stop learning.

And understand that range is just as important as expertise. As business owners, we need to know a little about a lot of things, as well as a lot about a few things.

7. Seek good advice from the right people.

Don’t listen to inexperienced people, and don’t seek specific advice from a non-expert in a particular area. That’s a waste of time, kills your confidence, and can put you down the wrong path. Instead, build a community of experts you can tap into for different things.

8. Hire for talent, experience and passion.

In the businesses I’ve pursued, education has generally not been as useful as skills learned on the job. Seek out people who are doing what they love and truly love what they do.

9. Provide an environment where your experts can focus.

I’ve found the fastest way to hamstring great talent is micromanagement. Let them go, and they will show you that you can trust them.

10. Nothing is permanent.

The hard times and the good times almost always pass. So, don’t sweat feeling lost or feeling like you don’t know what you’re doing. Everyone faces that. Just figure out how to mess up less the next time. And when things are going well, take a moment to breathe and enjoy it.

11. Find joy, and have some fun.

Figure out something that gives you a daily sense of joy and brings you energy, and then do that every day. Whatever is pressing can wait, and you’ll be in a better place to deal with it when you have a clear mind.

12. Integrity is everything.

Develop a process by which your organization can operate with a strong set of moral values. How you and your people conduct themselves is measured by everyone you touch. In the end, this is what you will be most proud of over any accomplishment.

13. Never stop trying to qualify for your job as CEO.

At every stage and level of success, you should always be the person you would hire to do the job. If you get to the point where you are not that person, it’s time to replace yourself.

14. Show daily gratitude.

Call team members out of the blue and tell them they’re doing a great job. Call a client and tell them you appreciate them. Thank your family for supporting you. They’ve had to listen to a lot!

15. Your perception is your reality.

I wish I had understood early on just how much mindset matters. Over the years, I’ve seen just how important this lesson in entrepreneurship is, perhaps more than grit or any other factor in one’s success. You must mold your thoughts before your plans can work.

Want to book a call and talk about your business with Patrick?

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