Thoughts and Reflections on Leadership and Small Business Ownership on our 15th Anniversary

By Dan Kahn

Today is Kahn Media’s 15th anniversary! With that in mind, I wanted to share 15 of the lessons I’ve learned (mostly the hard way) over a decade and a half of running my own business:

  1. Have an accountant you can trust and a bookkeeper you can count on. We made this mistake early on, and it’s a common one. Make sure your books are clean, and you have a clear P&L to use as a road map for growth starting on day one.
  2. Don’t hire employees until you absolutely have to, then hire the very best people you can afford.Hiring too fast or too soon will put a business in a cash crunch. But, like all things in life, you get what you pay for. So, as you scale, hire the best people you can, not the cheapest. Don’t fall into the trap of just hiring college grads either – some of my best employees had life experience but either no degree or one in an unrelated field.
  3. Leaders eat last.Once I started scaling, I needed things like a payroll company, HR consultants, insurance providers and benefits like 401K plans. Those are important for attracting the right people, but they’re expensive. Think of it as an investment, not a cost, and pay yourself with whatever is left over, even if that means forgoing a salary for a while.
  4. Your office doesn’t define your culture. You do.Nobody cares about office pool tables and free snacks if they’re miserable. Build a culture based on trust, encouragement, kindness and accountability. Lead by example – employees will mirror their supervisor’s behavior with both subordinates and clients. So set the tone and stick with it.
  5. Be resilient. Rockysaid it best: “Nobody is gonna hit as hard as life. But it ain’t about how hard you hit. It’s about how hard you can get hit and keep moving forward.” Challenges are constant, so be prepared and resilient. Do SWOT exercises, identify threats, don’t get scared and get motivated. Have a financial safety net and constantly look for ways to navigate around icebergs.
  6. Listen more, talk less. This is a hard one for me as a Type A business owner. But people (clients, employees, vendors) will tell you everything you need to know about their wants, needs and challenges. All you have to do is stop waiting for your turn to talk and actually hear them.
  7. The customer is always right, except when they’re not. My default mode is always trying to help clients as much as possible whenever possible, even if they’re challenging or non-communicative. But it’s also important to stand up for your people – especially if the client treats them poorly. It’s far easier to get a new client than it is to replace a great employee.
  8. Always be closing. I learned this one years ago when I stopped pitching new business for a beat when we had a healthy client roster and our staff was solid. Then we lost one client, and another went Chapter 11, and I ended up not getting paid for a year. Lesson learned – never stop pitching, cultivating leads and closing deals.
  9. Be Ned Flanders, not Mr. Burns. I’m dating myself with a Simpson reference, but as a leader, I’ve found that being friendly, outgoing and inquisitive gets you much farther with employees – even the struggling ones – than being the demanding, arrogant boss who browbeats people.
  10. Read constantly. I spend at least an hour per day focused on long-form content, mostly business books and leadership autobiographies. By studying the past, I’ve expanded my worldview and approached challenges with a fresh perspective that’s critical in challenging times.
  11. Know when to say goodbye. Not every employee is a good fit. If they aren’t in line with company values, aren’t willing to learn the job or can’t work with the team, those are hard issues to fix and probably will do harm the longer they stay. If it’s not a fit, identify it early and move quickly.
  12. Self care matters. Entrepreneurship is tough. High stakes, high stress and constant pressure can be very isolating. Employees and even significant others don’t always understand what you’re dealing with. I’ve found a combination of daily exercise, dedicated time to think and reflect, and a strong business peer support network are hugely valuable.
  13. Order the steak. Owning your own business is a tough gig, so when the opportunity presents itself to enjoy the fruit of your labor, take it and savor it. One of the highlights of my year was climbing to the top of a mountain with a group of media and eating a meal of fresh game cooked over an open fire. Some call that a life goal. I got to call that “work.”
  14. Pick the right partner. I don’t mean business partner. I mean life partner. Long hours, high stress, the need for constant empathy and EQ, and the willingness to solve problems constantly are hallmarks of business ownership. That’s a whole lot easier if your partner has your back, and mine has been a sounding board, source of wisdom and a steadying hand since day one.
  15. Be vulnerable. This is a tough gig, and there’s a reason 70% of businesses fail in the first five years – it’s really hard. That said, I don’t care if you run a dry-cleaning business, a marketing agency or a manufacturing firm. People are the most important asset in your business – both your employees and your customers. The best way to connect with those people is to be honest and transparent and allow yourself to be vulnerable. Admit when you make mistakes, learn from them and move forward. They will respect you, and more importantly, you’ll respect yourself. That’s how we grow.

That’s a lot of lessons! Thanks for hanging in there with me. Thank you to everyone who has helped us get to this point in our business.

To our clients, from those early brave souls who took a chance on us when we were a startup running out of a spare bedroom to our current roster that ranges from startups to Fortune 500 global brands, thank you.

To the employees – all of those who have given us their time and trust and allowed us to grow as a team while each individual hopefully grew their career – thank you.

To the industries that have given us a home – automotive, luxury and outdoor – thank you for the opportunity and for including us in the conversation.

We have some BIG stuff cooking for 2024, and I’m more energized than ever. Time to climb another mountain!