23 Lessons from 23 Years in Business

I officially started my business 23 years ago — the morning of September 11, 2001.

Of course, history and our lives changed forever that day. It was certainly a challenging start for the business, but challenges have been a constant companion throughout my journey.

Today, I’m known as the guy who started a business from one dollar and scaled it to mid-market size without partners or investors. I bootstrapped it so that it could truly be my company. I’ve guided my business through thick and thin, through four recessions, 9/11, a pandemic, a fire, and even a flood (my building caught fire during the Super Bowl in the early 2010s). Through it all, we’ve adapted and evolved, always focusing on human resources, always maintaining a consultative approach, and always prioritizing culture.

Over the years, I’ve learned countless lessons, personally and professionally. Here are the 23 that stand out most as I reflect on 23 years in business:

1. Challenges are workout sessions: Entrepreneurs face challenges every day. These aren’t just obstacles; they’re opportunities to grow, get better, and solve problems.
2. The path and the goal are separate: Goals will change as you evolve, and that’s okay. You derive the most value along the way, as long as you stay true to yourself and know your values.
3. Play the long game: Business is an ultramarathon, not a sprint. Good things and bad things will happen along the way. Keep your eye on the prize.
4. Build your support system: Starting a business requires a strong support system. My wife and extended family of entrepreneurs supported me while knowing I had to learn on my own, even if it hurt.
5. Leverage change: Change is one of your most important assets. Markets, situations, customers, employees — everything changes. Embrace it.
6. Understand the phases of business: If you’re blessed to make it through the first few years, you’ll go through distinct phases — finding your market, building a small team, creating your first management team, and scaling processes and technology. Understanding this complexity and how you communicate as a business matters.
7. Accept team evolution: The people who join you early for the entrepreneurial experience may be replaced as you grow with those who seek stability and scale.
8. Be willing to work for free: Starting a business is hard. Be prepared to work for free to prove your idea. I did this for many months.
9. Scaling is about small experiments: Scaling a business is a series of small experiments. Try things, learn, and either fail or succeed quickly, then repeat.
10. Build a caring culture: I learned that I could build a culture where people truly care about each other and our community. Today, my business’ culture is the most important element to our success. Cue lesson #11.
11. Culture matters as much as strategy: Culture really does matter. A good strategy will only get you so far if you don’t have a strong culture to back it up.
12. Strategy is crucial for scaling: Strategy, or how you create value and differentiate, is essential for scaling. You simply can’t grow without a solid strategy.
13. Execution is always a challenge: Effectively executing a strategy requires talent, focus, and planning. Execution has always been the most difficult for me as a scaling business.
14. Everyone can be a leader: Leadership isn’t about titles. Not every decision needs to come from the top down — trust your teams to self direct.
15. Know the difference in decisions: Understand the difference between a $9 decision and a $99,999 decision. This distinction isn’t always as obvious as it seems.
16. Trust is given, not earned: Trust is a full bucket that should be given, allowing people to learn, try, and stretch. Don’t make them earn it one day at a time.
17. Change your role as you grow: Be willing to change your role every year, or even faster, if you’re growing quickly. I’ve done every job in the business, but in year 23, I’m not qualified to do many of them today.
18. Know when to transition from Founder to CEO: Entrepreneurship requires two decisions — starting your company and deciding whether you’re willing to transition from Founder to CEO. They are very different roles.
19. It takes a village: You need a mentor, advisor, customer advisory board, and eventually a formal board. Accountability is key.
20. It’s lonely at the top: It’s true. Read, get advice, join an exchange group. Take in information and talk to those who have been there before.
21. Innovate where it matters: You only need to create the wheel where you’re innovating in your market and product. Bring in tried and true tactics for the rest.
22. Create a learning environment: As the old joke goes, the CFO asks, “What if we train them and they leave?” The CEO replies, “What if we don’t and they stay?”
23. Don’t take yourself too seriously: There is more to life than work. I enjoy playing many roles — community leader, thought leader, father, husband, and son. Each role has shaped who I am today.

Thank you to everyone who has been a part of the Placers, Opposite the Crowd, or Outside Insights community these past 23 years. Your support has been invaluable.

Cheers,

Chris