Leaders Listen: Leadership Lessons from a Longtime Entrepreneur

Theodore Roosevelt once said “People ask the difference between a leader and a boss. The leader leads, and the boss drives.”

When I endeavored to put my thoughts on paper about what it means to be a successful leader, I realized that it would be more effective to understand my leadership style from someone who has been on the receiving end of it for over 30 years. I sat down with my longtime assistant and colleague, Arlene Converse, to talk about how my leadership has impacted her career. Below are three takeaways from that conversation, and how they can positively impact your business.

Take risks on people you believe in.

When I met Arlene, she was a young mother who didn’t have two nickels to rub together. But upon our first meeting, I recognized what some might call “fire in her gut.” Not only did she have a desire to succeed, but in many ways, it occurred to both of us that she had no choice but to succeed.

A few years into my working relationship with Arlene, I made the decision to give her an opportunity to run one of our entities in an industry she wasn’t as familiar with. That was 22 years ago. On the other side of risk is reward, and my investment in and risk on Arlene has more than paid off.

In our conversation, Arlene asked me “Did you ever consider that I could fail?” My answer: “absolutely.” I knew that entrusting Arlene to run a business in an industry she didn’t yet understand was a risk, but there is no point in taking a risk in giving opportunity just to micromanage through it. That brings me to my next point.

Give people the tools they need to succeed, then give them the opportunity to fail.

This goes right back to the Theodore Roosevelt quote. “The leader leads, and the boss drives.” After rigorous training and education, I believed Arlene was set up for success. I was excited for her, and my excitement fueled her desire to succeed. But I knew for her to truly be successful, I would have to hand over the reins.

Throughout the course of my career, I’ve had many employees who were given the tools they needed to succeed, and subsequently failed, and that’s okay. The successes will always outweigh the failures, and there are always lessons to be learned either way. But you simply can’t be a good leader if you never put yourself and others in the uncomfortable position of risking failure.

Jim Moffat, Chairman and Chief Executive of Deloitte Consulting summarized it best when he said: “The aim shouldn’t be to try to have one uninterrupted string of successes, but rather to have a portfolio of some winners and, yes, some losers.”

Be someone people want to work for – and with – by being excited about your vision.

The bottom line is that no matter what else you do if you are not someone people want to work for and with, people will leave.

We’ve all heard the old refrain – it’s not where you work but who you work with that makes an experience worthwhile. According to a Gallup poll, 75 percent of people who voluntarily leave their jobs leave because of inadequate leadership. So how do you become the type of leader that makes people want to stick around?

Almost unanimously, employees that I have spoken to cite our shared excitement around our vision as the main reason for staying. Today, I run a fintech company that runs on culture-driven fuel. When you are genuinely excited about the work you are doing, that excitement will radiate and permeate the rest of your workforce and will rally people around you to continue to work for and with you.

As you can see, by speaking to one of my closest employees, I was able to identify some of the fundamental building blocks of my leadership style. And while leadership may look different for everyone, we can all agree that we cannot build strong teams without a healthy dose of risk, investment, and vision. Not only do I encourage you to use these building blocks in your own business, but share this article with your teams and discuss what they see as your building blocks of leadership.


Vincent Ney is the President and CEO of Expansion Capital Group, a business dedicated to serving American small businesses by providing access to capital and other resources so they can grow and achieve their definition of success. Since inception, ECG has connected over 12,000 small businesses nationwide to approximately $350 million in capital.