Dare to Disrupt: Lessons from a Serial Entrepreneur on Building Startups that Challenge the Status Quo

I had the pleasure of interviewing Bill, the Founder/CEO of Gumball, an advisory firm that has helped more than 80 CEOs rapidly scale their companies. He has been an important mentor to the people who have worked for him and is proud that more than 150 of them have become CEOs. Bill recently published “Press Go! Lessons Earned by a Serial Entrepreneur” to share both the business and life lessons that he’s earned throughout his career.

Bill began his career at Air Products — a F100 company. In his 12 years there, he held executive positions in Supply Chain and Information Technology. Longing to have a greater impact on the business, he left to find that opportunity in the world of startups. Seibel has been CEO of 10 startups and an Operating Executive for another 4. They include Cambridge Technology Partners (1992’s #2 IPO, $5.3B market cap); ZEFER ($136M revenue in its first 15 months in business — setting the record as the fastest-growing professional services firm ever; named Red Herring’s Top Company to Watch and Gartner’s Magic Quadrant Leader); Demantra (awarded Top Business Turnaround; acquired by Oracle); and Mobiquity (Fastest Growing Company in New England, One of the Top Mobile Firms in the World (Forrester), One of the Five Coolest Tech Vendors on the Planet (Gartner), and a finalist for Company of the Year — leading to a successful acquisition by Hexaware).

Bill has also served on 12 nonprofit boards, including Brigham and Women’s Hospital, Boston Public Library, D’Amore-McKim School of Business at Northeastern University, both the College of Information Sciences and Technology and the College of Engineering at Penn State, Carnegie Mellon’s School of Entrepreneurship, Boston Chamber of Commerce, New England Chapter of the Private Director’s Association, and the Telecommunications Committee of the US Chamber of Commerce.

Bill has been recognized as Tech Luminary, Technology CEO of the Year, Penn State Outstanding Alumni, CEO/Founder of New England’s Top Small Business, a finalist for New England’s Entrepreneur of the Year, featured in Forbes — Mobiquity’s Founder And CEO Bill Seibel Is Unstoppable, recognized by Governor Charlie Baker for his “many entrepreneurial contributions to the Commonwealth of Massachusetts,” and awarded Marquis Who’s Who 2024 for Extensive Contributions in the Start-Up Sector.

What motivated you to become an entrepreneur?

For me, it’s always been about hoping to build a special company. By that, I mean a startup that is financially successful, withstands market turbulence, and delivers on the expectations of its investors. One that delivers significant value to its customers. It’s also a company that satisfies the personal and professional ambitions of our employees. Perhaps, sometime in the future, they may point at a building or product, or a news article and proudly say, “I helped create that.” Most importantly, a special company disrupts an industry. It changes the rules. I believe that the biggest professional high ever is achieving something that everyone, even the experts, especially the experts, say is impossible to do. If your startup isn’t disrupting something — then why do it? Of course, that’s aspirational. It’s not yet who we are 100 percent of the time. But it is who we want to be 100 percent of the time. And I’ve been on a path to pursue that for more than 30 years. I love what I’m doing, helping entrepreneurs achieve their personal and professional ambitions. And I’ll continue to do that for as long as I can.

What has been your biggest challenge when growing your startups?

An “expert” is defined as someone who has made every mistake possible in a very narrow field — and that qualifies me as an expert in building teams. When I have an idea for a new startup, I share it with colleagues that I respect. Often, they will share in my excitement and ask if they can be part of it. I’ll invite them to ‘get on my bus’. As my idea matures and evolves, and I have a better idea of what I really need, I look back and ask myself, “who are all these people on my bus and how did they get there? And, more importantly — how do I get them off?” Lesson #1 — do not build your team until you have a clear idea of the skills and experience you need to make your startup successful.

I attempted to mitigate that risk when drafting the founding team of my next startup. There was no shortage of people who wanted to join, and I had learned how important it is to make the right hiring decisions. I invited 15 potential team members to spend a day developing our business model and exploring how we would work together. Not only were they all very talented — each also brought a piece of the puzzle we needed to build a special company. As the day unfolded, it became increasingly difficult to get the group to stop focusing on what was in it for them. Our discussion deteriorated to reporting structure, compensation, and who would be entitled to a private office. I adjourned the session early and coined Lesson #2 — The population of talented people is large enough that we could always surround ourselves with talented people who aren’t A-holes. Culture is critical.

As I gained more experience, I saw a lot of great people rejected because they “were not a culture fit.” Google culture. It’s defined as the characteristics of a particular group of people, encompassing language, religion, cuisine, social habits, music, and arts. That has nothing to do with how a team performs — and it crushes diversity. That doesn’t define a great team. That defines a playgroup! Now google values. It’s defined as principles, standards of behavior, and what’s important in life. And that’s critically important to a high-performing team. Lesson #3 — when building a team — go with values over culture.
More recently, I learned Lesson #4. When building your team, commitment to the mission trumps talent. As Herb Brooks said, when he was criticized for passing on the USA’s most celebrated hockey players on his way to winning the 1980 gold medal — “I’m not looking for the best players. I’m looking for the right players.”
Building the right team is always a big challenge. You need to recruit the people with the skills and experience that you’ll need in a future that may still be a bit unclear; team members who share the same values and also commitment to the same mission.

If you had to share, “words of wisdom,” with a Founder who’s about to start their own startup, what would they be?

A good business idea starts with the customer, not with the technology. Cambridge Technology Partners was built on a technology that was 28 years old; ZEFER on a 17-year-old technology; and Mobiquity on tech that was 38 years old. When a new technology finally takes off, it’s not because, all of a sudden, there is a fundamental change to the technology. It’s because, all of a sudden, there is a fundamental change in the business problem companies are attempting to solve.

So, find a problem that people have — that they need to solve. Figure out how you can credibly solve it. It needs to be a big problem. Customers need to be willing to spend money to solve it. And if they already have a budget to solve it — better yet. So big problems are good, but big, complex solutions aren’t good. Don’t worry about the technology until you have that figured out. Then capture that in a succinct Customer Value Proposition that explains why your prospects should buy from you. It doesn’t state what you do; it clearly and concisely frames why you do it. Getting that wrong is the biggest mistake that I see startups making.

How can our readers follow you on social media?

I’m active on LinkedIn (linkedin.com/in/billseibel). And I’m happy to do my best to answer any questions that you send to bill.seibel@gmail.com.

This was very insightful. Thank you so much for joining us!