16 Years of Entrepreneurship; 16 Lessons I Will Never Forget

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This year Situation turned sixteen years old. It’s our official Sweet Sixteen! As hard as I have worked over the past sixteen years, I consider myself to be a very lucky dude. Many people work hard (far harder than I) and don’t get the luck of longevity in their business for one reason or another. We’ve grown from a single person shop to almost eighty staff members. We have serviced many of the leading global entertainment and media brands. And I have had the privilege to work alongside a range of amazing people — from junior to senior.

As I reflect on my personal growth, I want to share my top sixteen learnings since I founded Situation. This is advice I wish I had received before I got started. Whether you’re interested in starting a business or just trying to embrace the entrepreneurial spirit in your own role, I hope you’ll find these helpful. In no particular order…

1. Someone’s word is more valuable than someone’s signature. I’ve signed many contracts over the years and one truth always prevails — a signature alone can’t save you from bad people. I’ve chased people who have owed me money, and I’ve learned the hard way that who you do business with is equally important as the actual business you do.

2. Living below your means is the single best path for growth. We have grown one-by-one to where we are today. We have grown off our own sales. No reliance on bank loans or investment capital — just a patient, focused strategy to save and live below our means. There are plenty of counter arguments that an infusion of capital is the wiser move to manage growth. But for me, the freedom to think and act on what is truly best for the long-term of the company has been far more valuable than any outside investment.

3. Respect is the only currency that counts. Virtually all conflict I’ve seen in business stems from a lack of respect. Respect of one’s opinion. Respect of one’s time. Respect of one’s authority. Leading with respect cures many ills.

4. Trust action. Or more bluntly — “put up or shut up.” Many people have a good heart and good intent, but struggle to turn ideas into action. I admire the person that writes the first check, takes the first leap into the unknown; the person who leads by putting their own skin in the game. This can be hard and scary, which is why it’s such an admirable trait.

5. The power of the human spirit is remarkable. The kindness people extend to one another far outweighs the cut-throat spirit the media business culture is often painted to be. When I started, I was far more reluctant to believe in this basic idea. But as the years pass, I’ve seen people do unbelievable things for people they care about. This is one of the most inspiring things I get to see from where I sit.

6. Flexibility is the most important employee perk. What might be meaningful as a 25-year-old may not be as meaningful as a 45-year-old. Aside from salary, benefits like vacation time, work from home policies, and a 401(k) become more important. If your goal is to recruit a team of people for the long-term, create an environment of flexible policies that can shift with your employees’ needs.

7. “Working for yourself” is not an accurate description of entrepreneurship. My name is attached to many documents that say if something goes wrong, I’m on the hook. I speak with many young people interested in starting a business, and one of their driving reasons is the ability to “work for yourself.” This is the wrong reason to start a business. I have eighty employees who are dependent on me and the success of the company. That is a heavy burden and a responsibility that should be seriously considered before starting a business.

8. Nothing good ever happens after 10pm. Well, I’m sure we could all smile about a moment that happened late one night after a few cocktails. But as someone who used to work in the nightlife business, I can assure you that in my professional life, good things rarely happen after 10pm. Playing the social scene is part of my business, but you need to know “when to say when” well before something happens that you don’t want to become witness to.

9. Loyalty is a double-edge sword. The idea of loyalty is very important to me. I try to surround myself around people I trust, and there’s no better trust builder than commitment and consistency. At the same time, loyalty can be blinding. It’s hard to be objective in relationships that start to feel personal. “That’s just the way they are…” or “but they do these other things so well.” I don’t have a solution, but I try to be vocal and aware of the tensions that can arise.

10. Believers create good. There’s nothing more inspiring than discussing big ideas with people who create momentum in the development of the idea. The “yes, AND…” people. At the same time, there’s nothing more demoralizing or frustrating than sitting around a bunch of people who inherently start with “no, BUT…” The power of believing creates a compounding interest that’s at the core of innovation; and if you don’t have that around you, growth is impossible.

11. Doing the right thing isn’t as hard as it seems. I’ve worked with many business owners over the years — good people do the right thing; bad people don’t. “It’s complicated” is a weak way of skirting around doing the right thing. I’ve met some incredible leaders who lead through incredibly complicated circumstances, and yet they consistently make the right call — not simply the easy one. This is what makes them great.

12. Government doesn’t relate well to business owners. This isn’t a political statement, and it applies to all political parties. I know; I’ve operated under all of them. The way government officials talk about small business, and the rigidity with which they govern is counter intuitive to how most entrepreneurs work. If I didn’t compromise, I wouldn’t be in business today. (Good gravy, I hope I don’t get audited because of this article!)

13. The full picture often never sees the light of day. The sheer number of decisions I must make on an ongoing basis precludes me the opportunity to give full context to the reasons behind my decisions. People always respond better to decisions when they understand “why” and for a range of reasons, I often don’t have the runway to deliver the full picture. This is one of the most frustrating growing pains I struggle with personally.

14. Growth hurts, but it does the body good. We’ve grown so big that I often don’t recognize the people in our own hallways. Growth hurts, and many people struggle as change can be uncomfortable. But as painful as it can be, growth provides fuel for personal and professional development. Watching the growth of our young employees in their careers is among the most fulfilling outcomes of this long ride of entrepreneurship.

15. Work-life balance is a journey as much as it is a destination. There are never enough hours in the day to capture all the priorities I have. One day I’ll feel like I’m not focusing enough on the business, then the next day I’ll feel that I’m not focusing enough on my family. These feelings typically aren’t linked to time spent — they’re linked to the sense of fulfillment I take from the time spent. I’m at my happiest not when my hours are balanced between work and personal — but when I feel present and useful wherever I am. The biggest threat to “balance” is the empty calories of unproductive time that creeps up on all of us in some way.

16. Business will always be very personal to me. We are all human and deal with human issues — life, death, and everything in between. A business deal in-progress will always pale in comparison to any personal issues — from health to happiness. This is why I love surrounding myself with people who don’t take themselves too seriously and bring a human kindness with them wherever they go. I want to be in an environment of passionate people who focus on humanity more than policy in the culture we create.

Celebrating my company’s Sweet Sixteen, I’m not going to say I know how it all actually happened. I believe much is a mixture of luck and right place/right time. I do feel, however, that I’ve taken a lot along the way; from the mentors I had, to the schools that taught me the fundamentals of what I do today. And for this reason, I try to give back. Cheers to Situation! Cheers to the people that supported me all the way through! Cheers to the next sixteen to come!

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