Ray Peloso on Hard Work, Self-Awareness, and Positive Impact (His Mother Would Be Proud)

When we decided to do a Hall of Fame for executives in late 2024, the first name I mentioned was Ray Peloso. Little did I know then that I would be conducting his interview and writing his profile a little over a year later.

After a very challenging year for Maestro, it was only fitting that I would sit down with one of the people responsible for making Maestro (and me) what it is today. I met Ray at a CEO roundtable in 2017, where I was speaking. The organizers had told me that I could not run over because the speaker after me was a Presidential candidate, and he was on a very tight schedule.

When I arrived, they let me know that the schedule had flipped and that I would now be speaking after the candidate. In essence, he was now my opening act! I started that presentation with that joke; a few people laughed, and some others just rolled their eyes, thinking, “typical sales guy.”

Ray was one of those who rolled his eyes. However, my bad opening joke did not stop him from having an open mind and listening to what I had to share. After the presentation, Ray approached me, and we scheduled some time to speak. Thus, the beginning of a great friendship and mentorship relationship had begun.

I don’t believe Ray set out to mentor me. I think he had a problem and felt I might have more insight than he did, so scheduling a call was a logical step. That is the thing about Ray—he is smart and humble enough to know when he doesn’t know something.

This trait of seeking knowledge and taking advantage of expert insights has been a common thread throughout Ray’s life and career (more on that later). When I asked Ray about his career inflection point, he pointed to a leadership training he took in 2002 while at Capital One.

It was there that he had to tear down the walls of false bravado and ego. While they had made him fairly successful up until that point, they prevented him from having the self-awareness and emotional maturity necessary to be truly successful. As Ray shares the experience with me, he is energized and passionate. Two things that Ray often is when he is at his best.

He shares that he is still good friends with the trainer, David Martin. He tells me about sitting on a hill by himself during training, journaling, and becoming self-aware of his strengths and weaknesses. And then drops a nugget that I will carry with me forever (lesson 1,000,000 from Ray to me): “Awareness leads to choice. Choice leads to accountability.”

You really can’t blame 2002 Ray for being so cocky and confident that he needed leadership to become more self-aware and emotionally mature. At that point, Ray had been working since he was 11, raised in a lower-middle-class neighborhood by two immigrant parents. They taught him the value of hard work.

He took that lesson to Georgetown University, where he completed both his bachelor’s and his MBA. Upon graduating, he went to work in banking, where he found great success and many promotions. This young professional, whose mother arrived in the United States literally penniless, had already accomplished a lot by the time he met David Martin, but to hear him describe himself at that time, he was “a complete idiot.”

To Ray, being successful but lacking self-awareness or an impact beyond the bottom line makes you an idiot. Hearing Ray speak about the seminal moment when he realized he was an idiot and wanted to break down his facade made me curious: “Did he think I was an idiot?”

So, I asked him.

The answer was “no.”

It was the expected answer, because in all my years of knowing Ray, there are three things he doesn’t tolerate: 1. Idiots; 2. Whiners or people that lack grit; 3. People who don’t deliver.

The thing about Ray, though, is if he did think I was an idiot, he would have told me. Not to hurt my feelings, because Ray is not cruel, but because he values integrity and would not lie about how he felt about someone when asked (he would use tact, but his position would be clear).

When we talk about integrity, he points back to his parents’ influence, in particular his mother (he is quick to point out that his dad is a great guy and an ethical man). He also shares that he has tried to impart on his three daughters the wisdom of his mother, that to lead a good life, “you need to be making a positive impact on those around you in the world.”  And that making a positive impact should dominate other considerations.

As he shared this tidbit, I felt it was the best time to share with him the positive impact he has had on me. He took a bet on Maestro (and me) when it was only a few months old. He gave us a big project and challenged us to deliver excellence. When we did, he bet on us again. He pushed us again to deliver more than what we thought we were capable of and challenged us to reach new heights. His belief in us became core to who we are as a company.

After I tell him all this, Ray reacts humbly. Thanking me for sharing. Given the impact that he has had on my life, I felt I needed to ask him one more question before ending the interview. So, I ask, “I have a 14-year-old son. If you could give him any advice, what would you say?”

Ray pauses for a few moments and then shares a lesson for my son that I will be forever grateful for: “A successful life requires deep and enduring commitment. It requires you to have grit and resilience. You don’t quit, you don’t give up, you must be in it. You must be committed to those who count on you.”

As he shares this advice, it is clear to me that this is who he became on that hill in 2002.

You can learn more about Ray here. Be sure to congratulate him while you’re there!