O.B. Rawls – A Payments Legend…Executive Director of Wellesley Hills Financials & founder of Jeroboam Advisory Services

OB Rawls is an accomplished senior-level executive with phenomenal success in FinTech payments and banking. He previously served as CEO of global payment processing for Paysafe and CEO and President of iPayment. His career of more than 30 years also includes senior-level executive roles with First Data now Fiserv, Hypercom, and Bank of America.

OB will be taking us on the twists and turns of his journey, including his most recent move, joining the firm of Wellesley Hills Financial as partner and executive director. And of course, along the way, he will be sharing with us a few insightful, actionable takeaways. So stay with us.

Transcript
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You're listening to Bridges to Excellence. Inspired leadership in payments and fintech. Show today, payments legend o.

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we limit our, um, our capacity as salespeople when we sell on price. And there's still a lot of agents in the marketplace saying, let me see your statements and let me tell you how I can save you some money. So I think salespeople have to be smarter, have to be more forthright, have to be focused on verticals and what all the needs of that vertical are and how they can, um, solve multiple problems for the merchant at one time.

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Welcome to Bridges to Excellence Podcast. Inspired leadership in payments and fintech. Bringing you conversations with payments most fascinating people on top of their game. Leaders, influencers, experts, and innovators. Each weekly episode turns our guests wisdom into practical advice. Their personal journey starts now. are meant to inspire and challenge you to explore your possibilities. Here's your host, Desmond Nicholson. OB Rawls is an accomplished senior-level executive with phenomenal success in FinTech payments and banking. He previously served as CEO of global payment processing for Paysafe and CEO and President of iPayment. His career of more than 30 years also includes senior-level executive roles with First Data. Now Fiserv Hypercom and Bank of America. OB will be taking us on the twists and turns of his journey, including his most recent move, joining the firm of Wellesley Hills Financial as partner and executive director. And of course, along the way, he will be sharing with us a few insightful, actionable takeaways. So stay with us.

Desmond Nicholson:

Obi, welcome to the show.

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Desmond, thanks for having me. it's really nice to be here and it's nice to, um, connect with you after all these years back from our First Data.

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For me, it's a privilege having you on the Bridges to Excellence podcast. There's no question in the fact that you are among the most respected and admired professionals in the payments industry today, especially within the ISO community. So again, thanks for being here. Now I understand in 2020 you attempted to retire and failed miserably. Is that true?

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That's true. And I really, was not very good at retirement, but I would give people who are following my footsteps and thinking about retirement, this advice never to retire in the middle of a pandemic. you can't travel, you can't,

Desmond Nicholson:

well taken.

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you know, it's, and so, I quickly kinda, wrapped myself up and work again. Pleasantly though, very pleasantly.

Desmond Nicholson:

coming out of Covid Pandemic, you started the consultancy firm of Jeroboam Advisory Services, since then, a few months ago, you joined forces with Wellesley Hills Financial as partner and Executive Director. So I guess there's no slowing you down. Is there.

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you know, I worked for a guy named Joe Plumer one time and he said, look, I can rest when I'm dead. That was his.

Desmond Nicholson:

Sage, Sage advice indeed.

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Yeah,

Desmond Nicholson:

Of course, uh, OBE. A bit later we will get into what Wellesley Hills Financial is all about, and of course talk about their go-to market proposition and also pry into what attracted you to them in the first place. first, let's start with your backstory. Shall we

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sure.

Desmond Nicholson:

us back to your earlier life, where you grew up and what your life was like while you were growing up.

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So Desmond, I, grew up in the east of North Carolina, 90 miles east of Raleigh, right on the coast of the interbank in a little town called Washington, North Carolina. very small town population of under 2000 people. it was in agricultural fishing. Town, and I grew up on a farm outside of town. It was a, great way to grow up, in the country. we didn't have a lot of money, but my parents seemed to manage our lifestyle, so I never knew I was poor until I was grown, during that time growing up and a good life, it was sort of like. The book, Hillary Clinton wrote that it takes a village to raise a child. I had,

Desmond Nicholson:

Mm-Hmm.

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uncles and aunts around us and so I had, 10 sets of parents growing up, and it was a fantastic way to grow up a lot of fun

Desmond Nicholson:

No chance of going wrong.

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where you were caught every time you did so.

Desmond Nicholson:

Uh, now where did you, go to school?

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I, went to school. I got my undergraduate degree at East Carolina University in Greenville, North Carolina. And, it always surprises people when I tell 'em my undergraduate degree was in social work. And so I actually worked for two years as a parole officer. and I found out that, government work was just not for me. I seemed to have too much ambition, to fit in with, the slower pace of, state government. Work. And then, I went to work for, bank of America and while I was there I went to, college on the weekends at Queens University in Charlotte. And that's where, I got my MBA.

Desmond Nicholson:

so you are now with, Bank of America. Should I assume that's where your payment, career started?

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I worked for the bank for 18 years, Desmond, and spent, did a lot of different things, in inside the company. Lived in, six different cities in the 18 years that I worked there. we were growing and we had sort of a go to grow mentality inside. And my last assignment at the bank was running. I was living in Norfolk, Virginia, running the, the credit card acquiring. Business for the bank. And, we had a, crisis inside the bank, and needed to raise cash. So I was tasked with finding a partner to finding someone, either be a partner with us in merchant acquiring or, to sell the firm to, and we ended up negotiating a joint venture with First Data. And we created, a 50 50 venture called Unified Merchant Services. And, that's how I moved from bank acquiring into, the enterprise. And, learned really a lot about payments back then, Unified Merchant Services. We were the fourth largest acquirer in the US back then. So it was, a lot of fun. We had a lot of, small business accounts and, some large accounts. We acquired a couple of big airlines, including American back then. So a really good education early on in my career about acquiring.

Desmond Nicholson:

So UMS was among the first, alliance partners that First Data had then right.

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It was, we were, number two. Wells Fargo was first, Deborah Rossi created the first joint venture with Roger Pierce.

Desmond Nicholson:

Your career with First Data was I guess, a maze of twists and turns, So can you walk us through the highlights, those milestones of that period the roles you played?

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Well, yeah, it was, very interesting. Back then, because the payment space was primarily manual, Desmond, it was a paper-based transactions. Merchants, at the end of their business day carried their drafts to the bank, paper drafts that were deposited into their banking accounts. And, we were, switching from, Paper to electronic processing. It was also a time where there was a lot of growth in, processing. and so business was expanding rapidly. We were educating the marketplace on not only, taking credit card transactions, but taking credit card transactions electronically. And, it was really exciting because we got, to help a lot of merchants, discount rates then were fairly high compared to now. And, merchants were very resisting to taking credit cards. They, thought it was an added expense to their business and they didn't understand that, the more options you have for, Clients to pay with the more your businesses grow. And we sold a lot back then on the, value of credit increases, the average ticket size and therefore more profits for the merchants if you take cards.

Desmond Nicholson:

So you were with, the UMS Alliance. I think it was from about 1993 to 1995,

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that's right.

Desmond Nicholson:

the president of that alliance.

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I was,

Desmond Nicholson:

Okay.

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and then,

Desmond Nicholson:

Then from there, you moved on, I think, to Nations

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no, I was at Nations before. I call it Bank of America now because not many people remember the Nations Bank

Desmond Nicholson:

you.

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name. But when, I left there, I went to the UK and built the, Lloyd's Bank joint venture for First Data, and I was the first General Manager. of, that,

Desmond Nicholson:

Now, that was about 1998,

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Yeah. There was a, there was a really interesting period of time when I was with UMS. we won the bid to process for the 1996 Olympics. In Atlanta. And, that was an exciting time. We actually did one of the first smart card pilots at the time for the 96 Olympics using, Hypercom terminals and Visa cards. It was a lot of work and we had okay results. we were, a little ahead of our time in the US hoping to use, smart cards, but it was a good, learning field.

Desmond Nicholson:

Can you elaborate on your experience with, Lloyds Bank? And that's the Lloyd Bank, TSB In Basildon on the outskirt of,

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That's right.

Desmond Nicholson:

London.

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Lloyd's bank was much like, other banks. in the growing credit card business, they, just like Wells Fargo and just like, Bank One and PNC and other banks that became, Alliances of First Data in the acquiring process figured out that as a bank their costs were too high to be in the competitive. Merchant acquiring business. And so by outsourcing their infrastructure, creating an external sales force that weren't bank employees, the alliances were able to compete in the, in the selling process, uh, much better. If you remember around, I guess 92. And on, that was the beginning of the era of ISO creation. And so

Desmond Nicholson:

Sure.

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these organizations that were just really good at selling and were good at, buying wholesale services from Uh, the major processors changed the market. They were very competitive in the marketplace, and banks with their existing infrastructure at the time, just weren't competitive. And so it was a, very, opportune time for Fiserv. If, remember Roger Pierce and Linda Mock, and Scott Lofted this as they created the acquiring program. And, we just took what we built in the US over to the UK with the Lloyds Bank joint venture and that joint venture is still in existence today.

Desmond Nicholson:

Wow. it occurred to me as you're talking that was the last meeting I think you and I had. I'd gone over to London to Lloyd's, to help set the stage. For bringing their, sales folks over to the United States at our sales training academy. And I remember the day when we sat down in the meeting, you were there, you gave it your blessings, and you had to leave for a meeting. And that was in 1999. that was the last time you and I were in a meeting together. Um, where did you go after there?

Track 1:

Well, I came back to the States. I spent, three years in healthcare. and that was an, interesting time. And I'll tell you, Desmond, I ran just as fast as I could back to the payment world. it was a nice experiment and I learned a lot, but it just wasn't home. So after, I left the, healthcare arena, I went to, Hypercom in, Phoenix, and there I ran global sales and operations for Hypercom I guess on all around the world. So I, went back to London, spent a lot of time. There again, rebuilding the distribution networks in Europe and Asia, and Latin America. But during this time, not but excitedly during this time, the electronification of payments was growing significantly. People were understanding the value of using, what was called a credit card terminal at that time. For card acceptance. And it was an exciting time. The world was, rapidly going to electronic payments and, consumers were more comfortable in using credit cards. And if you remember back during this time, the whole economy of Europe was changing in the Reagan years. The Iron Curtain came down and but all throughout Europe. There was the creation of middle classes that hadn't been there in the communist world. And so consumerism was growing unbelievably, But with that consumerism growth came the growth of credit card sales and processing. In the beginning, especially if you look through Slovenia, Slovakia, Hungary, the Czech Republic and that whole world, that was the eastern side of the Soviet block. They were hungry for consumer appliances, washing machines, and dryers and refrigerators, and most of those were processed using credit cards. During that timeframe, just an amazing period of, growth.

Desmond Nicholson:

I remember the, Hypercom all in one terminal.

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Yeah. Yeah.

Desmond Nicholson:

were the days

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Oh yeah. Well, after Hyper, mI actually went back to First Data I. And I spent some time with First Data right as we went, private. And so, I came back and I ran Tasq which was the hardware sales arm

Desmond Nicholson:

Okay.

Track 1:

First Data. And, from Tasq, I did a lot of different things inside the company in that nine-year period of time. I had a lot of the sales force for, large merchant services, so accounts from Sears, Walmart, Kmart was still around then, McDonald's and so large national and global retailers, uh, petroleum companies. And then, we had new business development and we had relationship management for those companies. I had the, the ISO channel, the bank channel at one time, and my last job there was running, The third party distribution business or the ISO channel as we know it. So in the nine years I stayed there, I probably had seven different roles in the nine years. And the value of that Desmond is you just pick up so many different tools that you can put in your toolbox and things you learn along the way that, Hopefully make you smarter and wiser and more balanced in your approach to the marketplace.

Desmond Nicholson:

Absolutely. So that's, Tasq. Now, where did you go from there?

Track 1:

when I left First Data, I went to I payment when we went, when we did our transactional, we went, public again. I I had to stay around six months after we, filed, and so then I took over the largest ISO in the world. Our payment. At that time, and we were a troubled asset. We had more, debt than we had in revenue. We had, maturing bond portfolio. and so we had to quickly refinance the company, uh, and build it up. But, our payment itself, Desmond, was a really, really good. asset, good people, good processes. It just had poor leadership and, poor management of the, resources that we had. but we were able to turn it around and we sold it to, Paysafe for 960 some million dollars and. That was a really good win for the employees and the shareholders And then I stayed with Paysafe for a couple of years. Retired at the end of 2020. Since that time I've been, working as an advisor, a consultant. I have, some board seats and we've done a couple of investments in small FinTech companies along the way.

Desmond Nicholson:

Now tell us more about, Paysafe, your function there.

Track 1:

At, Paysafe. I ran global acquiring for Paysafe. it was primarily, a North American and a European business. We had no business in Asia or Latin America. we were solely in the North American continent and, Europe. during that time I had small business acquiring large, you know, merchant acquiring, e-commerce, gaming. Um, so it was a, broader role. And again, I put a few more tools in the toolbox, Desmond.

Desmond Nicholson:

How would you describe your leadership style?

Track 1:

I think I'm a, team builder. Uh, I'm a, communicator. I like to gather information. I like to solicit advice Of the people that are below or above me in the chains. And then, I recognize that with all of that input as a leader, it's my responsibility to make the decision. So I'm not a consensus builder in that terms, I try to understand. What I'm charged with as a leader. So I gather a lot of information, hear what people have to say, listen to opinions that differ from mine and others, and then, make a decision. But you can't leave anybody behind. we're all on the same team together. So we move forward as a group, we win together and, if we lose, we lose together as a team.

Desmond Nicholson:

Okay, now we've come full circle. It's now 2023. What are you doing now?

Track 1:

So, about almost six months ago now, I knew the guys at Wellesley Hills Financial, and I had the opportunity to make an investment in the firm and to join, as a partner and, as the Executive Director of the firm, and I'm really having probably more fun than I've had in a long time. Desmond in this role, Wellesly Hills is a, uh, boutique investment bank headquartered in Boston. We, focus primarily on buy and sell side activities, so we help, people buy and sell. their businesses and we have, three focuses. We do traditional payment deals, sales of iso sales of small payment companies. but we also, have a specialty in the, FinTech market for, fintechs that have some type of enabling technology that help them, Stand out that helped them be different, and differentiated in the marketplace. And then we focus on fintechs that have some type of, software play or in the B2B space or a SaaS model. So we have three areas of focus, fintechs with, technology fintechs that are software or SaaS driven. Traditional payment deals.

Desmond Nicholson:

what attracted you to the. Firm in the first place and, what is your day-to-Day role?

Track 1:

Smart. So my, day-to-day role with the firm is, primarily, rainmaking, you know, creating, paths to, opportunities for us. And then deal management, in the process. But yeah, primarily rainmaking, We've, significantly increased the pipeline since I've come on board and, um, we've changed the focus of the firm a little bit to be more focused in these three areas. But we're really primarily a sell side investment bank. we eat what we kill, we generate fees from the sales of our properties and, we, don't exist unless we, create the transactions that help them be successful.

Desmond Nicholson:

okay. over the years, CEOs and leaders shared their thoughts on the phrase Work life balance, what does that mean to you and would you phrase it differently?

Track 1:

I would call it work life imbalance. it's a little, at least for me, Desmond, I, I don't know if I'm a workaholic, but I know that, over the years that my family suffered. from traveling, I've got over 5 million, well, four and a half million air miles on Delta and a bunch of miles on other airlines. And so I missed a lot of birthdays. I missed a lot of family gatherings, and, if I were doing this all over again, I think I would spend a little more time at home.

Desmond Nicholson:

Mm-Hmm.

Track 1:

I should have found a way to do that along the way. So, I wasn't very good at work life balance

Desmond Nicholson:

Hard work doesn't build wealth. True or false? And why?

Track 1:

No. It, doesn't build wealth. I learned to say it a long time ago. Plan your work and work your plan, and so

Desmond Nicholson:

Mm-Hmm.

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have to plan who you want to be and where you want to go, and then you have to set goals, and you have to, um, understand what it takes to, achieve those goals and how to win. And so I know a lot of people that work hard every day, but they don't have, they don't have the right mix of ambition, timing, fortune. Fortune plays into a lot of wealth building it in itself. So it's always nice to be good at what you do and to have the wind at your back to push you forward. So, unfortunately hard work does, not, create wealth hard work's just one part of the combination to success.

Desmond Nicholson:

Got you. what was a low point in your journey, what was that like yeah. Everybody has low points in their careers and in their journeys, and in my case, I kinda lost the way I.

Track 1:

in thinking about how I treated teams, how I, planned for success. And I had a period where I was more autocratic. I wasn't listening I wasn't being the type of person that made me happy as a leader. And, when you come to that realization, you realize that you changed. You're not who you thought you were or who you wanted to be. And so I really had to work to get back to a point of more balance in my life and, to be a better person. And when I did that, I was happier. I, I worked better, more efficiently and had better results. So balance to me is the driving, force behind our success and our happiness. And, it's in business terms. You have three entities you have to support. You have your shareholders, you have your clients, and you have your, employees. You, have to figure out how to solve and to serve all of their needs. And if you let either one of those overpower the other, then the wheel gets wobbly, runs off the tracks and you don't perform as well. So to me,

Desmond Nicholson:

So it

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balance,

Desmond Nicholson:

balanced.

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balance is the key to success.

Desmond Nicholson:

Great. Now, what emergent technology has caught your eye that holds great potential for the payment FinTech ecosystem, and why is that? I.

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I know it's the buzzword of, today, but I really believe that AI that artificial intelligence. Used in the right way is going to change the way we use data to drive our decisioning. And, machine learning can calculate and provide, um, opportunities and solutions to us faster than we can as people. It's a tool. it's not the end. We have to treat it as a tool and use it as a tool. And, we shouldn't be scared of AI. But, if you think about some of the algorithms that are used today for embedded finance and embedded, lending and embedded banking, they tell us so much information about our clients. And so if you're, a company that has, um, embedded, banking services. by having the checking account of the merchant, you get to see how they spend their money. Right. And knowing that and understanding it and analyzing it, allows you to build a whole host of services and insurance and finance and lending and, Payroll in company management techniques, and you can create an offering of products and services to, your client base that we don't see today. I've always thought that the best way to keep a merchant happy was to be able to sell him a lot of products and services, but our distribution system's not set up for that. if you think about most of the new merchant sales still come from third parties in the marketplace, and they're singularly focused. They're, I'm going to sell this merchant account. The merchant needs to buy payroll, he needs to buy insurance, he needs to finance his pizza oven, and he needs to do a lot of things, but we can't sell it to 'em that way. Through implementation of AI and then through. Other embedded tools, then we can offer solutions that these small businesses want and it helps them stay in business longer. And if they do, guess what? We stay in business longer. So to give you a good example, I think Square's use of, cash app of deposit services, of software services, they've been one of the best at offering products and services. To their small business clients. So AI is a tool for me.

Desmond Nicholson:

Okay. a decade ago, the CEO of a top acquirer predicted that. Transformation within the industry would bring about the demise of ISOs and MLS sooner rather than later. Do you think this prediction will eventually become true, or do you see a strong future for the feet on the street? And, what can agents do to help ensure their survival in the coming year and beyond?

Track 1:

You know, honestly, I think that agents could be endangered species, Desmond, in the marketplace, but not, anytime soon. the world is becoming increasingly focused on verticals. I. How to service those verticals better. most of the agents in the field are, generalist, and so they're, going to have to change. people still like to buy from people, so the last mile still exists in all types of selling, but we've got to, be more focused on what the merchant's needs are. More focused on how we can help 'em solve those needs instead of just saying, Hey, I got a product for you and you need to buy this because I can save you 10 cents. Or I can offer you, cash discounting and you can process for free. It's bigger than that. we've gotta become more professional. we have to become more broad-minded, and we have to have, Other products and services that merchants want to buy to exist. and I really believe that there is a continuation of the sales model if we get better at what we do and if we focus on merchant success instead of agent success.

Desmond Nicholson:

What do you see as the, greatest challenge facing the payments and FinTech space right now?

Track 1:

This is a naive answer, but I think it's selling on price. I still, I think

Desmond Nicholson:

Hmm.

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we limit our capacity as salespeople when we sell on price. And there's still a lot of agents in the marketplace saying, let me see your statements and let me tell you how I can save you some money. So I think salespeople have to be smarter, have to be more forthright, have to be focused on verticals and what all the needs of that vertical are and how they can, solve multiple problems for the merchant at one time. That's not going to be easy.

Desmond Nicholson:

OB, with such a rich tapestry of career accomplishments over the years, what would you most like to be remembered for?

Track 1:

You know, desmond that's a question. I've never, it was one that's, I've never been asked that before. I. And two is, I'm not really sure. I think in the business world, I want to be remembered for being fair, being progressive, being successful, you know, as you say, as we talked earlier about leadership, you know, wrapping our arms around. The team and all of us, celebrating success together. So to me, fairness, the ethical treatment of employees, of the ethical treatment, of clients and customers and providing returns to shareholders that are fair is important. So I just, I still don't, I haven't answered your question. I don't know how. I just did the best I could.

Desmond Nicholson:

That's, a good attempt. Now we move into our final round.

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The lightning round bridges to excellence, inspired leadership in payments and fintech.

Desmond Nicholson:

Okay, OB, in this segment I pose a question and you respond with a single word or one sentence. Shall we begin?

Track 1:

Yeah, let's try it. I'll try to be nice.

Desmond Nicholson:

Okay. The road not traveled.

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I wish I could have been a public company. CEO.

Desmond Nicholson:

What does success mean to you?

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Absolute happiness.

Desmond Nicholson:

What is the best advice you ever received? I.

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You need to take off that lead life jacket. Son,

Desmond Nicholson:

What one book would you recommend to our listeners and why?

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It is a little old fashioned and out of, favor today, but I would recommend that more of us should read the Bibles of our faith a little more and understand the principles in the, teachings.

Desmond Nicholson:

Good. What is your favorite quote in leadership or otherwise that inspires you?

Track 1:

That was a, that was a tough one, but treat others with respect. Treat everybody with respect.

Desmond Nicholson:

Who is your hero of all times and why?

Track 1:

You know, Desmond, I've never picked a hero there's so many good examples of leadership out there. I had a really good mentor one time, a gentleman named Lowell Thomas when I worked for the bank. Lowell was a tough boss. I mean, he was really a tough, hard boss, but he was thoughtful. He was sharing and he wanted to train the people that worked for him, but he was tough. And you had to be hard you had to. Understand his style, but he was one of the best bosses I've ever had. Taught me a lot, good things and bad things about who I want to be and who I should be and how I should work.

Desmond Nicholson:

Okay. What is one thing the people you work with? Would be surprised to learn.

Track 1:

I'm a softy. Yeah,

Desmond Nicholson:

Okay. got you Wine or bourbon. What's your favorite?

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wine, but I like both

Desmond Nicholson:

What is one thing like both

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I.

Desmond Nicholson:

What is one thing that has you fired up right now?

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this is a quasi political statement. I just wish, Desmond, that our country was not so divided. I wish we could on both sides of the fence, find something that would unify us together to move forward. We're a powerful country and I just wish we could, Learn how to get along and work together.

Desmond Nicholson:

Obie, it's been fun. taking us on your journey from your backstory to your new partnership at Wesley Hills Financial, all while sharing along the way nuggets of insightful wisdom. And of course for that we're grateful. cheers to you, my friend,

Track 1:

Thank you, Desmond.

Desmond Nicholson:

and best wishes for continued success. A legend in payments indeed. Now any parting thoughts to share or comments before we wrap up?

Track 1:

Yeah, I've touched on this briefly. Um, I, suggest to, people, um, be true to yourself. Um, have a, have some type of, or some set of guiding principles that drive you forward every day. Some anthem that you can sing, to yourself, and then be good, be kind, be fair in the process. Being a boss doesn't mean you have to be. A hard person who doesn't care, that is not concerned with the people they work with, but have your set of guiding principles and follow those.

Desmond Nicholson:

OB thanks for being on our show. And to our listeners, as always, you for your time and never forget the more you expect from yourself, the more you will excel.

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You've been listening to Bridges to Excellence podcast, inspired leadership and payments and fintech. Be sure to join us next time for more conversations with another of your colleagues in payments and fintech. Insightful conversations in their journey to excellence for transcripts and other materials covered on the show. Visit us at DesmondNicholson. com.

About the author, Desmond

Desmond Nicholson is the creator and host of the Bridges to Excellence podcast

1 Comment

  1. Tim McWeeney on 03/10/2024 at 1:10 PM

    A master class in payments and in life balance by OB Rawls.
    Thoroughly enjoyable and informative.
    Great interview!

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