True Grit: 35 Lessons From 35 Years Building a Company

Today is Sullivan’s 35th anniversary. When I started the firm in 1990, I never dreamed I’d still be at it 35 years later. But starting and building this company has been a dream come true. I’m so proud of what we are today: my teammates, our clients, the work. We’ve been true to our mission although we look nothing like what we did at the start.  The world has changed and so have we.  

We’re ranked among the top 10% of independent advertising agencies. Our strategy and creative work receive numerous industry accolades. And our team members are sought-after speakers. But these are the stats I’m most proud of: Our average client tenure is 8.9 years—almost 3x the industry average. And employee tenure is 8.7 years, 3.5x the industry average. It’s proof that we’re doing something right. 

How did we get here? For anyone just starting or considering starting a business, I offer 35 lessons learned over these many years—shared in the hope that they might help you navigate this journey with greater clarity, resilience, and purpose.    

Starting from Scratch. 

1. Find your niche. Look for a need that’s not currently being met. Focus on the NEED, NOT the product, and make it your north star. The product will change over time. 

2. Get in the weeds. Make sure you know—to the most minute detail—how you’re going to execute. Without it, your idea is just a daydream.  

3. Set measurable goals. Build a plan and set metrics so you can measure your progress. Have an exit strategy in mind before you even start.  

4. Build flexible systems. Focus on building strong, sustainable systems that are not dependent on a few exceptional people and can be changed as the world around you changes.  

5. Jump in before you’re ready. The timing will never be perfect, you’ll never have all the answers, and even the best plan will always have a few holes. Maintain a bias towards action. 

It’s Personal. 

6. Always act with integrity. Your reputation is your most valuable asset.  

7. Check your ego. This is not about you. While your identity might be tied up in the company, it’s a team sport. Try to never burn bridges, no matter how painful.  

8. Take risk. Don’t be afraid to make mistakes. Use your judgment. Go outside your comfort zone and try new things. Some of it will work and some of it won’t.  Build on your successes, learn from your failures and keep pushing yourself and your firm to be its best.  

The Company You Keep. 

9. Know what you’re good at. Define your role around your strengths—then hire to fill in the gaps.  

10. Hire the best people you can afford. Find people who are experts, but also consider how their personality, motivation and values complement the team. 

11. Learn to let go. What got you here won’t necessarily get you where you want to go. Delegate, empower and trust. Give your employees the freedom to contribute, grow and develop as they fulfill their own ambitions. 

12. Encourage employees to think like owners. Motivate them to contribute to what matters to your business. Giving them incentive compensation, bonuses, or even equity can align your interests and theirs. 

13. Find the best outside advisors. Work with good lawyers, accountants, bankers, and consultants who have experience working in your field or with companies like yours. They’ll be an ongoing source of wisdom—to seize opportunities—and stay out of trouble. 

Everyone’s a Salesperson. 

14. Make it easy for customers to buy.  Remove hurdles and don’t make it complicated to buy your product or service. Consider something small to encourage trial.  

15. Be clear about what you’re selling. Customers will want to know exactly what they’re getting, especially if it’s a service. Describe deliverables in tangible, easy-to-understand terms.  

16. Charge what you’re worth. Undercutting your competitors may get you some short-term gains but it’s not sustainable. Offer your best work and charge what it’s worth—you’ll need the money to pay for the best people and deliver the best service. 

17. Retainers are a false sense of security and make it harder to buy. If you do good work at a fair price, clients will be loyal. If you don’t, they’ll look elsewhere. 

18. Understand who makes the decisions. The person you’re talking to is not likely the only person who has a say—especially if your clients are large corporations. Learn who the buyers and the influencers are—including procurement, general management, legal, HR, etc.—and be attuned to all their motivations.  

19. Know your competitors. Not just in a generic sense, but ideally in every pitch. Know what sets you apart and what to push harder on. Play to win. 

20. Don’t give up. Sales cycles can be long. Be patient and persistent, and find ways to maintain an ongoing dialogue with your prospects. When you get a “no,” assume it just means not right now—and then be there when they’re finally ready to buy.  

21. Ask for the order. Have confidence in what you’re selling. You’re not being annoying or “salesy” if you’re offering a valuable solution to a problem your prospects need to solve. Act like it. Be direct, assume they’ll say yes, and give them the nudge they need to get over the hump. 

22. Marketing works. Know your audience, understand their needs, and invest the time and money to reach them with a message that motivates them to act.   

23. It’s okay to say no. Not every customer is right for your firm, and not all growth is good growth. If the work is a distraction, sucks up resources in an unproductive way, or doesn’t align well with your skillset or mission, just politely say no. Or recommend a “competitor” for whom it might be a better fit. 

Loyalty Matters. 

24. Always do right by your clients. Yes, always. Even if it means owning up to a mistake, starting from scratch, or losing money on a transaction. Your dedication won’t go unnoticed and will pay off in the long term. 

25. Be the best part of your clients’ day.  Strive to make the time your clients spend with you fun and inspiring. Surprise and delight them. Leave them looking forward to the next time you meet. 

26. Prioritize your existing customers. The time you spend building long-term relationships is far more rewarding and profitable than churning clients. 

27. But don’t ignore new clients. They keep you on your toes and bring new energy and vitality to your company. And of course, they’ll be tomorrow’s long-term clients.  

It Comes Down to the Numbers. 

28. Hoard cash. Anticipate your cash flow needs and plan so you NEVER run out of money. Have a standby line of credit for emergencies that hopefully you’ll never have to use. 

29. Spend money on what matters. There are some things you can’t compromise on. Be frugal with everything else. 

30. Keep clean, accurate books. Never co-mingle personal and business expenses. 

31. Pay on time. You made a commitment to your employees, vendors and partners. Honor it. 

32. Reinvest in your business. Set targets and reinvest some of the profits back into your business. That’s how you’ll continue to evolve, to enhance your offerings, invest in infrastructure, and attract and retain the best people. 

Enjoy the Ride. 

33. Pat yourself on the back.  When you do something well, acknowledge your accomplishment.  It’s easy to focus only on what needs to improve. 

34. Set limits. Building a business can be all-consuming. You’ll be better in your role if your life is full—family, friends, exercise, adventure. Make time for the things you truly love. 

35. Have fun. Life is short and you’ll spend a lot of your life in this endeavor. Make sure it brings you and your team joy.