Founders' Forum

What Smart Entrepreneurs Do in Uncertain Times with Kerry Benson

Marc Bernstein / Kerry Benson Episode 154

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Uncertainty is everywhere—but what if it’s actually an opportunity? In this episode of Founders Forum, recorded in July 2025, Marc Bernstein sits down with Kerry Benson, alongside guest co-host Karla Trotman, to unpack how leaders can navigate constant change with clarity and confidence.

Kerry, President & CEO of Big Edge Advisors, shares his journey from humble beginnings in Queens to becoming a trusted advisor to executives and boards. With over 35 years of experience in technology, finance, and leadership, he offers a grounded perspective on thriving through disruption—without losing sight of what truly matters.

Together, they explore how today’s uncertainty—driven by global shifts, AI, and economic changes—differs from the past, and what leaders can do to stay steady in the chaos.

Key Takeaways:

  •  Why uncertainty feels more intense today 
  •  The power of having a constant anchor 
  •  How early hustle shaped Kerry’s path 
  •  Lessons from scaling and transformation 
  •  The “Seeds and Seasons” life framework 
  •  Why people-first leadership matters

About Kerry Benson:

Kerry is a seasoned technology executive, business advisor, private investor, board member, and mentor who has built a 35+ year career driving digital transformation and enterprise value. As former Chief Information Offer of PFM and now President and CEO of Big Edge Advisors, he helps senior executives, business owners, and boards solve complex challenges through leveraging his expertise, strategic partnerships, and powerful network. Known for his leadership, operational excellence, and people-first approach, Kerry is a trusted advisor to C-suite leaders and colleagues alike.

Connect:

Website bigedgeadvisors.com
LinkedIn linkedin.com/in/kerry-benson-a5417a

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Welcome And Sponsor Message

Announcer

The following programming is sponsored by Marc J. Bernstein. The views expressed do not necessarily reflect the views of this station, its management, or Beastly Media Group. Entrepreneur, founder, author, and financial advisor Marc Bernstein helps high-performing business owners turn their visions into reality through his innovative work and the forward-focused forum. Marc connects entrepreneurs to resources that fuel their success. Founders Forum is a radio show and podcast where entrepreneurs share their journeys, revealing the lessons they've learned and the stories behind their success. Join Marc and his guest for a mix of inspiration, valuable insights, and a little fun. Now let's dive in.

Why Uncertainty Feels Everywhere

Marc Bernstein

Good morning, America. How are you? We are here in um uh kind of hazy Philadelphia on a very hot dog days of summer kind of day. By the way, we're all dog owners in the studio here this morning. And I recently looked up the the the dog days of summer. I don't know if you guys know this, but um where it came from. But I think it was a Roman, like goes way back to Sirius, who was the dog god, I think. And uh and and that makes sense because I see on Sirius XM they have a little dog logo sometimes they use, right? So so there was something about um it was in the middle of the summer when the when when that god was kind of came out and when there were a lot of storms and stuff like that. So it down over the years it's become the dog days of summer. Anyway, so there we are. So we're not gonna talk about that, although the weather is very uncertain, and our topic that this morning that we're gonna talk about is uncertainty, because there's certainly a lot of it in the air these days. And Kerry, who's our guest today, actually suggested the topic, and Karla is with me. And in a second, well I'll introduce Karla because she's already been on our show. Karla Trotman is president and CEO of Electrosoft Incorporated and author of Get Her Book Dark, Dirty and Dangerous The Building. Oh, Building the Vibrant Future of Manufacturing. So something got messed up in our notes here. So anyway, it's on Amazon. You can get it where books are sold. And um, I, for one, am going to be reading it. Um and Kerry, I'll formally introduce in a minute, but we were talking about so in the news today I mentioned that the Wall Street Journal had an article about the effects of the tariffs. That's a big subject these days. And um that those kind of things and the policy decisions by the Trump administration, and again, this is not political, this is just observation of what's going on, and the uncertainty it's created in the economy and in basically in the United States culture right now, that we're just starting to see a little bit of the effects of that, especially in the economy. And they also observe that the effects aren't as bad as economists predict predicted, but that remains to be seen. There's still a lot of things up in the air. So it seems it's beyond that. It's it seems like we have a culture of uncertainty worldwide at this point. Kerry, you brought up the topic, but give us your thoughts on that.

Kerry Benson

As I said earlier, and by the way, thank you, uh Marc, for inviting me uh to the show. And uh so this is really a a good time for me. Um, but I I think um it is it is a very relevant topic, obviously. Um uncertainty is it's it's not obviously a new thing. I mean, we've always had to deal with it. But but but today, as we stand, whether it's uh uncertainty in terms of you know where the the f financial markets are, um or uncertainty as far as changes that are being impacted by things like AI, um all of these things are ultimately um change related and they create uncertainties for people. And so it's um it's something that I think about every day, it's something that's in our faces. Uh the good news is that we're evolving and there are some positive um things to to look at um in terms of the uncertainty. Uncertainty and change, you know, in the end, it may seem scary in the beginning, but then over time things tend to work out. So this is this again, this is not a new topic, right? Um and I think what's important, um, at least for me, and and I try to share this with friends and colleagues and people that I mentor, is that in the midst of uncertainty, it's always important to have have something that's constant, something that you can turn to, something that you can rely on and kind of stay focused on in the midst of uncertainty, in the midst of change. And for for different people, it means different things. For me, it's having a plan. It's it's thinking about you know the road and journey that I'm on on an ongoing basis and making sure that you know I I make adjustments to some extent, but at the end of the day, I'm still focused on that goal, you know, that journey.

Marc Bernstein

Remain focused on your journey. Yes. Got it. Karla, your thoughts?

Karla Trotman

Yeah, I just had a question for you, Kerry. Do you think that it's a little different this time? Whereas in the past it may be a recession or or something happening geopolitically that doesn't really impact us, but this time it's more of a restriction.

Kerry Benson

Yeah, I I think the difference is is that one, it's it's much more in your face. And I think uh given you know the different you know things that are going on, it's happening um in so many places, in so many ways, whether if you're you're working for the government and you're worried about your job, or if you're working in, you know, life science, life sciences and you're worried about you know your your research dollars, or if you're working in, you know, technology, which is where I come from, it used to be that, hey, if you're in tech, you're good. You know, you don't have to worry about anything. You're you kind of got the golden ticket. That's not the change. That's not the case anymore. That's not the case anymore. So so it is different in that sense. It's it's it's happening, it's so pervasive, in other words, it's happening everywhere, and not only on a in the you know, in the U.S. but around the world when you think about it, right? Other countries are now having to deal with uncertainty around terrorists. Like, okay, what what's gonna happen today, tomorrow, you know, is it gonna stick, is it not? You know, what does it mean for me? So I think it is very different in that sense. Yeah.

Meet Curry Benson And The Theme

Marc Bernstein

Do you think I I see a big connection between uncertainty right now and disruption, because it's a big time for disruption. I mean, we're you know, we're our country is being led by chief disruptor, and I'm you know, I'm not again, no judgment in my what I'm saying right now, but there's no question that he is out to change as much as he can in the world. And he was not the only one. He's modeled himself after some other leaders around the world that are trying to do the same thing. So so therefore, I think the uh to your point, Carl, I think the uncertainty is much more pronounced than than what we've seen in the past. Yeah. So anyway, so let me introduce Kerry Benson now. Kerry is president and CEO of Big Edge Advisors. I love that name. Kerry is a seasoned technology executive, business advisor, private investor, board member, and mentor who has built a 35-plus-year career driving digital transformation and enterprise value. As former Chief Information Officer of PFM and now president and CEO of Big Edge Advisors, he helped senior executives, business owners, and boards solve complex challenges through leveraging his experience, strategic partnerships, and powerful network. Known for his leadership, operational excellence, and people first approach. Kerry is a trusted advisor to C-suites and colleagues alike. So, and he's also an entrepreneur, I want to mention, too, because we may not have come through in that um in that summation. But welcome again, Kerry. Thank you. Thanks for being here. Um so Kerry and I just mentioned real quickly, met at a meeting of the Sattel Institute. That's right. And you've heard a lot about that because we've had Ed Sattel on the show telling both his business story and the Sattel Institute story. And we, as a board member there, I I I put on commercials for Sattel Institute because it's a great, it's a really interesting organization that's creating a um a platform nationally, it started in Philadelphia, but nationally for uh businesses and nonprofits to interact and figure out how to best serve their communities. And um and I I know are you new to Sattel?

Kerry Benson

No, I oh I'm I um I've been attending uh that um I I've attended several meetings. Uh a good friend of mine, Alan Cohn, over at um Sage Financial.

Marc Bernstein

Oh, yeah.

Kerry Benson

Uh he and I work together um uh on the board of a nonprofit. And so I go as a guest of his.

Marc Bernstein

Nice.

Kerry Benson

Uh and also Tony Conti, who's I think Tony was the vice chair there. He's he's my mentor, actually, in one of my mentors.

Marc Bernstein

Oh, really? Yeah, interesting.

Kerry Benson

Great, great friend for many years.

Early Hustles And Learning Tech

Marc Bernstein

I didn't know that. So very interesting. So let's talk about your how you're how you got started in your career um and really kind of started as an entrepreneur at at a young age.

Kerry Benson

Yes, absolutely. So I'm originally from New York City. I grew up in um uh Long Island City, uh Queens, and uh oldest of three uh children in a single parent household. You're a typical urban kid. Uh I was the oldest, uh, and I kind of always prided myself in trying to be a good role model for my younger siblings. And uh and I grew up, you know, in the uh in the 80s, you know, early 80s. Um I'm not as old as as young as I look.

Marc Bernstein

Um but um I was always uh the kind of person I think I was gonna say you're you're you're not as you you look younger than than that. Yeah to me you look younger than you than when you grew up. But anyway.

Kerry Benson

Oh yeah, well thank you. Um so I I grew up uh again just always thinking about where I was. I was a very self-aware kid, and I had to be because of I guess my environment. And I kind of lived, you know, two lives. I tell people I grew up with uh about maybe 14 guys we'd run the streets and you know, um and I was uh fortunate enough to always be thinking about the future, always looking around me, looking at the older, older kids. And so I started out at a young age at 10 with a paper route, right? I have I do I delivered papers on Sundays, I delivered groceries. I was always trying to figure out ways to help my mother. Um and um and that led me to um starting a barber business. I remember sitting in a barber shop one day, again, didn't have a dad, so I'd take myself to the barber and I would sit there and had I've been waiting a while and I got tired of waiting. I'm looking at the barber cutting the person's hair, and I'm like, I can do that. And so I I leave and I, you know, I got impatient, and I ended up going out and buying myself a pair of clippers, and I ended up uh cutting my own hair, and then next thing you know, I'm cutting my friend's hair, and I and then from there it just started growing into a business at 13, and um and it got to a point where it just kind of got a little out of control. Um went on to college and um I was through entrepreneur though.

Marc Bernstein

You saw one you saw a need and you fulfilled it.

Kerry Benson

Yes, yes. I was cutting out of my bedroom, you know. But um that wasn't kind of where my my my future um weird and weird lied. I I always thought about I was a big star Star Trek and uh lost lost in space kid talking about my age, right? Now we know, right? Now we know.

Marc Bernstein

If you know lost in space, yeah, you're up there.

Kerry Benson

So I was intrigued with you know lights and buttons and so on. What I really wanted to do was I wanted to be an engineer, but I had no guidance. I didn't know what that was. There was no one around me that I knew that even went to college, right? Um, but I ended up uh buying myself a computer when I was in high school, actually, a Commodore 64 uh 64 computer, which you know is one of the first computers, taught myself basic programming in my my room that I share with my brother. My brother's watching cartoons, and I'm I'm on the compute, the computer learning how to do basic. And and that um led me to go into college, and I ended up at Baru College, studied information systems. Coincidentally, when I uh took my first computer programming course, I didn't do well on my first COBOL exam. Uh, and the professor called me into his office and says, Kerry, you'll you you should change your major because information systems is not where you, you know, where you should spend time. And I really that I took that that to heart. And um and from that point forward, I, you know, I got all A's in my my computer classes, and I was always a good student generally, but it was, you know, it it really was one of those things that kind of set me on the course of of you know focusing on technology. And from that point, I ended up um getting my first job out of uh college working for the uh New York City uh transit authority in the capital budgeting division as a junior programmer. And uh I did very well there, but I didn't like the environment because it was uh it was just too a little too slow for me. I was teaching everyone everything, and I was like, I gotta get out of here. I wanna I want to learn in that that stage of my life. So I ended up moving on and uh joining an advertising agency called Foot Cone and Belting. And then there that's where I cut my teeth around hardware, and I was supporting 500 people in Midtown, running around changing, you know, hard drives and that kind of stuff. And that got me uh you know more adept into some of the you know the technical stuff. And then I ended up uh on Wall Street, which I you know did some programming too.

Marc Bernstein

Deloitte that was next.

Kerry Benson

Actually, no, it's uh it's a it's an organization called you know uh Public Securities Association, which is uh was a trade association for the municipal uh bond market. And uh and and there's a there's a common thread between all of these experiences along my journey, and you'll see kind of how it all culminates into into where I ended up.

Marc Bernstein

No, I know.

Kerry Benson

Yeah, yeah. So I ended up, you know, again at PSA programmer, ended up becoming a manager of the programming team and and ultimately uh started a company while I was there called Aerosync with a with a friend that I had grown up with uh in the neighborhood, and he actually came from the industry. I was, you know, I was always kind of an entrepreneur and had that reputation, so to speak, but he was a real like corporate sales guy, right? He he went through sales training for a company called CentOS and uh five years, and he was very, very knowledgeable. And so he got me into that business. We started everything from the ground up, and we go after big companies because he had that sales experience. And I was the analytical guy, back office guy, doing all the marketing and marketing and operations stuff. We ran out, um, we had our company, um, we were in downtown Brooklyn, and uh we ran out of our apartments, and uh we had uh we had a lot of uh sizable customers very quickly. We were growing too fast though, and we didn't know much about managing cash flow. And so we ran that for three years, and I decided to pivot, you know, you were still working your job the full time. And I was still working my job full-time. Right, right. Yeah. Interesting. Yeah.

Break

Marc Bernstein

All right, so pivot. Great time for a commercial. One minute, we'll be right back on Founders Forum.

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Marc Bernstein

We're back on Founders Forum with our guest Kerry Benson, and we have Karla Trotman in the studio with us. And uh, we were just talking about pivoting from the aerosync business, and you still had your job. And um at some point, I know you got your master's in finance at NYU. It's where I finished law school, so we share that in common. I spent a little time at NYU. And um then you were working on all kinds of cool stuff in the financial services business.

Kerry Benson

Yes, yes. So after Aerosync, I decided I wanted to do something else. And uh literally the last minute, last day, last hour, I took my application in to uh to NYU and said, hey, I want to get into the school. And and I remember on my uh the essay I wrote, I said, you know, I'm gonna be successful, and if you want to get credit for my success, you're gonna let me in. Right. And so I I I got in major in finance and um and I majored in finance uh because I I felt I needed to kind of have a balanced, you know, resume and background because I was everything I had done up to that point was technology related. And so majoring in finance and learning about all the products and and the industry was great, and it was perfect, perfect planning and timing for me because it really gave me uh a huge uh leg up. And did you have a question?

Karla Trotman

I did have a question. Um I I guess I think oftentimes that we as as business people we don't know really how much money there really is out there. And being on Wall Street almost gave you an edge and an insight into okay, this could be a very lucrative life if I spin it in the right way. I guess was that maybe part of the determining factor of getting your master's in finance?

Kerry Benson

You know, it was more um after being in finance uh for a while, I learned that because you know, some of the um, you know, careers like investment banking, sales and trading, all those careers I knew nothing about, right, until business school. Um and I learned, yeah, you can make a lot of money. Um I but I still had that technology, you know, goal in my heart, and I I just I just couldn't let it go, right? And so I study things like uh risk management in financial services and and I looked at systems at the time um and and you know we did some programming around risk management for financial products. I had to understand how the financial products work, but then what is what did that mean from a technology standpoint? What did it mean from a data standpoint? And this is I'm talking early 90s, right? Um so um it wasn't about the money for me so much, but it was about getting the experience, getting the skill, and doing something that was interesting and challenging.

Marc Bernstein

So that leads us to I you spent a long time at PFM.

Kerry Benson

Well, actually from B school, I ended up going to Deloitte.

Deloitte Lessons And Big Projects

Marc Bernstein

Oh, okay. Yes, Deloitte showed up differently in my notes. Yes, okay.

Kerry Benson

I ended up uh so I ended up finishing out um my MBA and uh got recruited at a couple of offers, but I decided to to uh join Deloitte. And it was one of the best things I could have done because it's a great place to get the foundation you need, um, whether it's related to technology, strategy, operations, et cetera. And I started out uh I started out with a with a kind of internal entrepreneurial group called Peerscape. We were building a financial benchmarking product. And I'll never forget when I graduated, I always wanted to go to Brazil. And I and I was gonna go with a group of guys to Brazil, and I had bought my ticket and I was ready to go, and then um I was asked to start on the day that the week that I was leaving during that week, and I was asked to build a telemarketing system for this this new product called Peerscape within six weeks. And so I forfeited my trip and um and I ended up building that system, making my mark at Deloitte. And the senior partner at the time who uh the who ran the practice, uh who became a mentor, Mark Swarez, who I'm I'm forever grateful uh to, um, he saw something in me. And uh from that point forward, I was able to, you know, get it get on really good projects. And so I worked uh in uh worked in healthcare for about three years, you know, implementing electronic medical record systems. I did some work in the manufacturing space, Owens Corning. Then I ultimately ended up working in financial services, uh moved over to the New York office, which was a very competitive office at that time. And uh my first project, believe it or not, was the JP Morgan Chase merger. Wow. I I was uh co-lead uh of a PMO in the investment banking division. So that was a huge opportunity and a huge undertaking. Um and uh and so on, yeah.

Marc Bernstein

By the way, I was just gonna mention, even before you mentioned the uh uh the um internal entrepreneurial group that you were working with when you developed the the product, the really you've been doing entrepreneurial type activities all the way through. That's there's a theme there. That's true. So I want to it's a show for entrepreneurs. I want to make sure that was clear. So you can be an entrepreneur within a company and and um and be very successful, which you were. So from Deloitte, what happened?

Kerry Benson

Yeah, so um I I worked um at JP Morgan on that project. I also worked um for a company, uh a big bank called State Street Bank, where I um I actually did the due diligence for an acquisition.

Marc Bernstein

They're Boston based, right?

Becoming CIO And Scaling PFM

Kerry Benson

Yeah, they're Boston based. Um and I ended up um doing due diligence, the applications due diligence for their acquisition of the back office for Merrill Lynch Investment Management. Um and so ended up doing a pretty good job there, got a job offer, turned it out, turned it down at first, but then I ultimately took And I started at State Street. They're running that, the technology team supporting Merrill Lynch Investment Management. At the time, they were managing about $190 billion in assets for fund accounting. So it was a big operation. And did a really good job there. Got called up to Boston by my boss and her boss. And they said, Hey, Kerry, you did a bang up job with this governance thing I had done. Hey, what does your future look like? And me being the type of person that I am, I put together a PowerPoint and says, Here's my journey, here's where I am, here's where um, here's where I've been, here's where I am, here's where I'm going. And I was a vice president at the time. And I said, in the next two years or so, I'd like to be a senior vice president at the bank. And then post that I'd like to be a CIO. And they were kind of like a little shocked. They looked at me and it's like, okay, sounds good. But State Street's a big bank. So I left, and 30 days later, I get a I get a call from a search firm looking for uh a CIO. They were doing a national search for this small company called PFM out of Philadelphia. And I interviewed, probably had maybe 20, 25 interviews, and ultimately uh ended up there. Now, what brings all of my my background and experience that I've talked about together is that PFM at the time uh it's it's it was a you know the conglomerate had uh it has a consulting practice at the time, it had an asset management practice at the time, it had it, you know, it was it it still is the largest independent financial advisor of the states and local government. So remember I worked at the Transit Authority, I worked at State Street, you know, in investment management, and I also worked at Deloitte in consulting. So all three of those, you know, kind of came together. And then also sort of entrepreneurial, right? And that was a common thread as well.

Marc Bernstein

So I just want to point out we time flies on the shows, and we've got a lot to cover. We only have about five minutes. Oh god. So I want to talk quickly about um, you know, what happened, PFM. In fact, I'll just read from my notes real quick that while you were there, you can as the CIO, you contributed the company's growth. We talked a lot about this, scaling from 220 employees and $35 billion in assets to 700 employees and 170 billion in assets. And then PFM got sold to U.S. Bank.

Kerry Benson

The asset management part of the business, correct?

Marc Bernstein

And you and you stayed on with them to help with the transition for for uh 12 months.

Kerry Benson

Right.

Marc Bernstein

And what was that experience like? And I want to make sure we get to talk about um your nonprofit work too before we're done.

Kerry Benson

So yeah, that was a great experience, very dynamic, you know, obviously uh very intense. Uh we pulled we pulled off that transaction uh in in less than nine months, around six or seven months or so. It was pretty intense. So great experience, and uh, you know, one I'll never forget. And I, you know, it was a little difficult leaving a great firm like PFM, but definitely in good hands.

Marc Bernstein

And as a result, you are now a consultant with your own firm, Big Edge Advisors, and consulting on a lot of the things, I know advisory work and private investing and board work. Um anything you want to add about that, and then we want to make sure we talk about seeds and seasons.

Kerry Benson

Sure. Yeah, I I I think um, you know, as far as the advisory work, I would say that I have a lot of experience, like over 35 years of experience in different areas, consulting, et cetera, things I've talked about. So what I enjoy most about what I do in terms of advisories is talking to business leaders about their goals, their their objectives, not only from a technology standpoint, but from a strategic standpoint, from a pre people standpoint. I've worked with lots of people. I'm a I have a good you know instinct for for strong leaders, et cetera. So I I play a very important role there in you know private companies, you know, public companies, as well as nonprofit, you know, companies. And just kind of dovetailing to my nonprofit experience. I've been uh working in nonprofit as a board member for more than you know 10 years and uh in Philadelphia. And so I'm you know really um happy with that that part of my life as well.

Marc Bernstein

Nice. So tell us about Seasons, Seeds and Seasons, which is a framework that you created.

Seeds And Seasons Life Framework

Kerry Benson

Yeah, sure. So Seeds and Seasons is is a framework that I that I created, and it kind of going back to me being very self-aware, I'm always very con uh conscious of where I am in this journey called life, right? And I look forward, but I also look back and say, you know, like where what was it that allowed me to get out of the circumstances that I was in? Why was I so different? And at the end of the day, it it came down to a few things faith, family, friends, finances, you know, fitness, and and ultimately fulfillment. So I look at my uh playbook, if you will, it's around those things, right? And I try to make sure that I'm spending time in all those areas. Uh, it's so important for me to stay healthy, right? Because you don't, if you don't have your health, you don't have anything. I spend lots of time with my friends. I have lots of friends and associates and leverage that very well. Um and I try to make sure that I'm giving back, you know, and pouring into my family, into the social relationships that I have. And then finances. I'm big into finance, right? I mean, I have to have the financial wherewithal to do the things I do and have the freedoms that I have today. So I'm always spending time in those areas. So when I think about season seasons, it's really around planting seeds in all those areas, but also thinking about it across the seasons of your life, right? Throughout time.

Marc Bernstein

By the way, freedom's another F. You could add to that too. I like that. Thank you. I'll add that.

Kerry Benson

Because that's what it's all about for me.

Marc Bernstein

Yeah.

Kerry Benson

Right.

Legacy Of Developing People

Marc Bernstein

Hey, we only we have like a minute. Um, just real quick, your thoughts on because you've done a lot. I know you have two adult children that are one's a uh teacher and one is in medical school and a long, happy marriage. Um what talk about your legacy for a minute that you'd like to leave, and then we're just about out of time.

Kerry Benson

Aaron Powell Yeah, the legacy I like to leave it it centers around people, and and I firmly believe that everybody has something to bring to the table. I think it's really the culmination and kind of collaboration of all the gifts and talents that we have as human beings, being able to identify those, help people see what I can see that maybe they can't see, uh, and then having them, you know, be able to leverage that. Um I think that that's so important. So really helping people uh, you know, to get the most out of what they're what they're here to do.

Marc Bernstein

Well, we squeezed a lot into a short amount of time, and I really appreciate you being here, Kerry. Love to hear your story, and we'll maybe we can get you back on. You'd be a great co-host. Thanks again to Karla for being here. And uh thanks to all of you for listening, and we'll see you next week on Founders Forum.