Tales of an Entrepreneur

Lessons-Learned

My company, Digital Royalty, just turned five! In social years, which is like dog years, that’s more like 35 years old. As I approach my 5th anniversary as the company’s founder, I realize there are some things that I wish I knew back then that I (kind of) know now when it comes to entrepreneurship:

  1. Get comfortable with being uncomfortable. When you start your company, there will be a thousand things each day that you’ve never done. That’s okay.

  2. Beware of shiny object syndrome. More companies fail from a lack of focus vs. lack of business.

  3. Your team is everything. Spend a great deal of time making sure the right people are on the bus and in the right seats.

  4. Entrepreneurs tend to wait too long to hire and too long to fire.

  5. Just because you can do it all, doesn’t mean you should. Realize what you’re uniquely qualified to do and delegate or outsource the rest as soon as you can.

  6. Don’t forget why you started your company. Remind yourself daily. (Or hourly if needed!)

  7. Being an entrepreneur is like the Chicago weather. If you don’t like the way something is going, wait 15 mins. It will change.

  8. Your plan is important but accept the fact that it’s going to change and you will need to adapt.

  9. When recruiting and interviewing talent remember this rule as you evaluate candidates: If it’s not a hell yes, it’s a no.

  10. You can’t turn your business off but if you don’t take time to go off the grid every once in awhile your business will suffer.

  11. Focus on the long game. Society has romanticized start-ups that burst over night yet that’s not the norm. Steady as she grows.

  12. A diverse support system is critical. You’re going to need more than just family and lifelong friends. It’s lonely at the top.

  13. You can color outside the lines without crossing the line. Disruption and destruction create two different outcomes.

  14. When we practice humility, our growth is accelerated.

  15. The people you choose to do business and the people you decide not to do business with will be the important decisions you make.

  16. Celebrate lessons. Lessons + blessings = Blessons. Accelerate the process of learning by sharing mistakes.

  17. Try to learn the difference between when to make things happen vs. letting them happen. Gas vs. breaks.

  18. Always call people back and return emails. Figure out a system for doing so if you’re “too busy”. It’s worth the time and effort.

  19. A five-degree shift changes your entire trajectory.

  20. Read outside the box. Don’t just read your industry trade articles. Explore beyond.

  21. The company can’t love you back. Logos don’t have feelings. Your team and partners have a human capacity but your logo does not. That doesn’t mean you shouldn’t passionately dive in head-first, just manage your expectations.

  22. There’s a big difference between true business partnerships and vendors. Alignment is key for longevity. Transactions are short-lived.

  23. Find a team of mentors and make sure you’re coachable. Then return the favor and mentor others.

  24. Your hustle factor is often your differentiating factor. Work hard.

  25. Where passion, purpose and skill collide, bliss resides.

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