In the Cut Leadership Conversation with Greg Webb

Greg is semi-retired and spends his work time as the Managing Director of Quantitative Business Solutions and an Advisory Board member of the National Black Brewers Association. He’s the father of 2 adult children and a grandfather of 1 adorable grandson.

How do you identify?

I identify as a black male raised by a single parent in a low income, segregated neighborhood in St. Louis, Missouri. I was a young black male youth who fortunately showed promise in a segregated school system and I had an awesome opportunity to optimize my skills. I transitioned into a private boarding school in Colorado and then attended the Washington University Olin School of Business  in St. Louis which exposed me to a lot of new options and new people. Those experiences enlightened me and ultimately expanded my perceptions and opportunities.

What’s the work that you do?

When I was younger, I always wanted to be someone who people looked to for advice. That  meant that I had to accomplish goals and earn respect from my peer group. That was always an early aspiration of mine. And fortunately, I've been able to provide leadership, advice, counseling, coaching and mentoring to a lot of people.

Most recently, I led several  incredibly impactful entrepreneurship and student financial literacy programs in Milwaukee which was a lot of fun and I miss the people I worked with. Over several years I led more than 200+ cohorts of aspiring entrepreneurs, many of whom have done exceptionally well, building multimillion dollar businesses. We facilitated the program at the local college until Covid hit and then we went remote. The program restarted several times and ultimately lost funding.

For several years, we met with hundreds of Milwaukee Public 7th and 8th grade students. We showed them how the stock market and stocks interact and established semester-long stock market challenges with groups of students. The outcomes were encouraging and we provided cash awards for the best teams and I picked up on some valuable stocks researched by the students!

I'm still in contact with some of the participants who often ask for recommendations and/or funding for their businesses. This is evidence of the leadership that I demonstrated that starts with helping people help themselves.

You owned a business. Please share a bit about the lessons you learned there that you could apply to the entrepreneurial program?  

It was the most enlightening experience of my entire career! It was an Anheuser Busch distributorship, and fortunately, a very easy business to establish. Even though it was kind of turnkey, it was still a big challenge because I thought I knew more than I actually did about how to deal with, manage and motivate people.

Maybe because I have sales generation instincts, I found it harder to motivate our administrative team versus our sales team. I ultimately learned how to motivate most individuals within each team. We developed a mindset that everyone had an impact on the bottom line and implementing the right incentives was key. For some it was a financial incentive and for others it was an educational offering that we had.

Our business was based in New Jersey, one of the most diverse markets in the  United States. I had no idea that it had one of the largest domestic Portuguese populations which was a major challenge. I had to lean into managing, directing and leading a team of 100+ people representing a lot of different ethnic groups.

I quickly learned the importance of listening to people and responding to what they were saying as opposed to assuming that I knew what the answer was. It was a very good learning experience for the young man who came from the inner city of St. Louis and was now in the real world.

“On paper, we were the perfect fit.”

You had a business partner, as did I. Talk a little bit about the partnership dynamics in leading your company.

Well, we should have had synergy. On paper we were perfect. We were put together in sort of a shotgun marriage meaning we didn't select each other. He didn't want to have a partner but he needed one and that set up a certain amount of animosity from the start. It was interesting and unfortunate that 2 individuals with a similar beginning ended up with an amazing opportunity, and we did not get along.

I believe it was because our values were not aligned. I was operating with a shared power mindset and he wasn’t. However, the struggle helped me learn more about myself than at any other time. For several years, owning a distributorship was a goal of mine, and when I got there, I had some of the skills that I needed but not all of them.

In a small company, every team member sees and experiences everything, especially the dynamics of the owners. In the end, our employees favored my leadership style and I still have a plaque of appreciation from them in my office. Even years later, when I've gone back to New Jersey, I attend gatherings with my former employees. I love the beverage industry and that showed up in how I led my company.

What was your first “known to you” leadership moment and what sticks out about it?

That goes back to playing sports in high school. At a private boarding school in Colorado, I was selected as the captain of the football team. I played both sides of the ball like Heisman Trophy winner Travis Hunter… but was obviously not as good as him! When you're on the field, you have to direct people. Fortunately, it was a small school with a small team. We weren't great, but it was a valuable opportunity to learn about teamwork.

It also gave me aspirations because I was around a bunch of very wealthy, privileged individuals and I was a scholarship student. It encouraged me to figure out how to thrive and not go back to the environment I grew up in. Consequently,  I advanced from being a mediocre student to the Dean's list and honor roll. 

Does your identity inform your leadership style? If so, how or why? I’m guessing the answer to this question is, yes, and I’m interested in hearing how.

Originally, I was not totally comfortable going into that new environment and being around people very different from me, with different values and who didn’t look like me. It was a challenge and there were several times when I wanted to quit because it wasn't comfortable.

At those times, I would remember my goal and that I had an opportunity that most people, who look like me and are from where I’m from, do not get. So, I had to step up to the opportunity and embrace it and along the way I made some lifelong friends. While not aware of it, those friends helped me figure out some important issues. I basically flipped the paradigm from feeling less than to knowing that I was more than. I lived into my aspirations and adapted to the environment giving me more control of the situation, and not giving away my power.

The glass went from half empty to half full and that’s an important leadership lesson.    

“Leadership for me is about helping people help themselves.”

What’s your leadership superpower?

Resiliency, not living into the swings of emotional highs and lows. Not reacting negatively  to bad outcomes. I have learned from them and continue to move forward. That's the key. Without it I'd probably be a  wreck!

Trading in the stock market has helped that a lot! The volatility in leadership and the market are very similar. You’ll have more up days than down days in leadership and investing.

What’s your life’s purpose?

Helping people help themselves.

It’s a year from now, what are you celebrating?

Another successful year with my clients and the stock market. More international  travel. And the healthy growth of my kids and grandson.

Thank you for hanging out In the Cut with me Greg!

Please drop a note to Greg in the Comments below.