From Wall Street to Garage Startup: Matt Plooster’s Culture-First Blueprint for Investment Banking

What happens when a former Wall Street banker trades skyscrapers for a garage — and builds a mission-driven investment bank from scratch?

In this episode of Leadership Levers, Matt Plooster, Founder & CEO of Bridgepoint Investment Banking, shares the remarkable journey that took him from billion-dollar transactions at Deutsche Bank to launching a boutique firm with a simple belief: people and culture aren’t just part of the business — they ARE the business.

Matt’s story is anything but typical. A small-town Nebraskan who once walked on to play football at the University of Nebraska, he later found himself on Wall Street working on some of the largest private equity deals in the world. But purpose — not prestige — pulled him home.

In this conversation, Matt opens up about the cultural principles that define Bridgepoint and how investing deeply in people has become his firm’s most important competitive edge.

Matt walks through:

• Why culture is the only sustainable differentiator in high-performance service industries
• The leadership tension between scaling fast and protecting standards
• Why most people problems are really clarity and accountability problems
• The investment resources Bridgepoint makes in its people — from success coaches to supportive chaplains
• How mission, purpose, and trust strengthen both the work and the financial outcomes
• Why gratitude and perspective matter more as the stakes get higher. 

For leaders navigating growth, hiring or culture drift, Matt’s story is a reminder that the real engine of performance isn’t strategy or capital — it’s people who believe in what they’re building together.

Seeking to align your culture, boost performance & impact your bottom line? Let’s chat—no sales, just real talk about your challenges. Not ready? Join our PL3 Community for free insights & connections.

Chapters

• 0:00 Meet Matt Plouster And Bridgepoint
• 3:20 From Cornhusker Dreams To Wall Street
• 6:40 Leaving Big Banks To Start Up
• 10:45 Why Culture Is The Only Moat
• 13:55 People, Process, Or Profit

Transcript

William Gladhart: 0:00

Welcome to the Leadership Levers Podcast. I'm your host, Will Gladhart, CMO at The Culture Think Tank. At The Culture Think Tank, we empower leaders with metrics that strengthen culture, drive performance, and return. We're here today to learn about the actions leaders have taken to address organizational change. Today, our guest is Matt Plooster, CEO and founder at Bridgepoint Investment Banking. Thanks so much for taking the time to join us.

Matt Plooster: 0:31

Thanks, Will. Great to be with you.

William Gladhart: 0:33

Absolutely. So let's begin by having you share with our audience a bit about your background and your organization.

Matt Plooster: 0:40

Thanks, Will. Appreciate you having me. So Matt Plooster, founder and CEO of Bridgepoint Investment Banking. I am a small town Nebraskan. I have a very non-traditional background for an investment banker or a high finance person, I suppose you could say, or industry. I'm from a town of 400 people in Norrisville, Nebraska. That being said, I was blessed to get an opportunity to go into investment banking in my early 20s, right out of undergraduate. I had, so I'm from Nebraska, and in Nebraska we've got one thing, and that's college football. And in the 1990s, that meant something. And so I was a brilliant 18-year-old kid who turned down a full ride at Harvard to play football there to walk on at the University of Nebraska in the late 90s. And some people would say that was crazy. It probably was from a practical, rational standpoint, but man, what a blessing. Be able to run out of the tunnel for the Nebraska Cornhouse because a small town kid who just grew up idolizing the program was really neat. That being said, uh two or three years into that, I played in a couple games and only when the score was like 50 or 60 points of margin. And uh started to think, okay, what am I going to be when I grow up? Because I'm clearly not going to play in the NFL. I'd gone from like 13th to 8th on the depth chart at slot guy or wing back, we called it. And somebody said, You should be an investment banker. This guy just made a million bucks and didn't do anything on this deal. And I thought, man, that sounds pretty good. Right. Back then you could not go to Wall Street unless you really went to probably a top 10 or 20 school, the Ivy Leagues, et cetera. And so I uh walked in and told Coach Solich, who was the head coach of Nebraska at that time, hey, I'm gonna transfer back to Harvard. Uh and he said, send me a check when you're a rich Harvard guy. And I actually did not get in the second time, Poetic Justice. And I had gotten really close to going to the University of Chicago out of high school as well to play baseball and football. A lot of people say it's the best e-com program in the country. And so I transferred there and I had two very distinct academic experiences. I had Big 12 football, not going to class much. And I had University of Chicago on the bell curve, where the first day I showed up on campus as a junior transfer, realized that everybody was a lot smarter than me, but a great experience. So I had I had a very unique kind of juxtaposition of two college experiences, but I really went there to get into investment banking. I was fortunate enough to get a both bracket investment banking job, which both bracket investment banks are Goldman Sachs, Morgan Stanley, Deutsche Bank, the big banks that you read about in the Wall Street Journal, which was really cool. And my parents, we didn't know what investment banking was. The people that live in my town probably don't know what investment banking is, but it was neat to come from a non-traditional background and be able to work at and for some of the largest financial institutions in the world. So I spent my 20s mostly at Deutsche Bank in Chicago, a little bit in New York, business school at Columbia in New York, which was also a neat experience for a small town guy. Did $40 billion worth of transactions. A lot of those transactions were KKR, Blackstone, Carlisle, some of the largest transactions mankind had done. But I always was kind of a redneck Nebraskan at heart. And my wife and I had met working at Deutsche Bank and we had wanted to move back to Nebraska and raise a family. And I think as you get older, Will, I had shared that, you know, I went into investment bank because you could make $100,000. Right. As you get older, it's like, okay, what am I getting up in the morning to do? Am I passionate about that mission? Do I feel purpose-driven about it? And there had never been a real investment bank in flyover country, which is where I'm from. Lots of boutiques like us in Chicago and New York and maybe San Francisco. And so we moved back at 29 years old with more courage than brands to start and build one and to do that. Started Bridgepoint Investment Banking, which is the name of our business, which is a boutique investment bank in 2010, 15 years ago. We just had our 15-year anniversary in our garage. And I can remember on a gravel road. And I can remember looking over and I was looking at the trash cans in my garage thinking, huh? I just went from the second biggest bank in the world to to a garage on a gravel road. Was this a wise idea? Um it's been a true entrepreneurial journey. I'm not a I never had a trust fund or anything, just a normal guy. My parents weren't. It's been a huge blessing, though. We had our conference last month and somebody said, 15 years, you know, that's amazing you made it. And I said it was really amazing given we almost went out of business every day for the first five or seven years. But fast forward to the day, sorry, that's a longer story. Perfect. No, thank you. Uh fast forward to day bridge point's 25 or 30 bankers. We're headquartered uh in Omaha, which is where I'm sitting today when I'm talking to you. Original office in Lincoln, Nebraska. We've got an office in Denver, Colorado, Chicago, and New York. And what does that mean? We do middle market investment banking for private American companies. We sell companies, do MA work, and we raise institutional capitals to help those companies grow and transition, et cetera. We are a little bit unique in that we're very mission-driven about who we serve. Most investment banks do a lot of their work for private equity funds, and we refuse to work for private equity funds. So there's a little bit of a Robin Hood angle, even though I think five of the seven firmsmen in my wedding run private equity funds or senior private equity funds. We love sitting on the side of the table of main street American businesses who maybe it's their maybe their grandma or their grandpa founded it, right? Or they did and they took all the risk with a ladder and a truck and have grown it into something they can't believe how big it is now. And they've got one shot at goal to either, you know, transition that, monetize it, or help buy out a family member or help grow more quickly. But they don't Wall Street is the biggest caring world with a lot of smart people who went to Harvard and Princeton. And how do we do that correctly and in the most optimal way? And so that's what we do. We raise money for companies and we sell companies, and we only do it for people that have never done a deal before, basically, who've got one shot at goal to take care of their lifetime blood, sweat, and tears of their work. So it's been a huge blessing. And everybody that we've recruited kind of is that same person which has done really large deals that has come down market because they feel very mission-driven about helping those companies. So it's been really fun. Anyway, that was probably more than you wanted. Well, that's what it was.

William Gladhart: 6:27

No, no, that was great. Thank you so much for sharing the background. We're not going to talk about the uh Nebraska football rivalry because you know I was at K-State during those periods. You know, where were some pretty good ones? Yeah, exactly. Well, where we weren't exactly that good of a team.

Matt Plooster: 6:41

So that was still a face mask on Eric Crouch, by the way.

William Gladhart: 6:45

Um, so we'll be discussing three questions today. And I think you touched on, as you were kind of wrapping up the summary about your company, what our first kickoff question is. As a warm-up, can you share why you believe a healthy culture is critical?

Matt Plooster: 6:59

It's kind of the only thing that matters, quite frankly. Everybody in our industry smart as a commodity, right? And everybody on our team could go work at another investment bank. They're Uber talented, amazing people. Certainly, some of the things that you have to be compensated well, right? You have to have opportunity, you have to believe in the place that you're at. I think it's a fact, probably, that all of us, especially in investment banking, which is not a 40-hour a week industry, we spend more time with our work family than we do our actual family. And so, why do you want to be there? And why do you want to be on mission together? Why do you want to get up in the morning and do work together? And so, belief in our culture, belief in each other and our why is and trust of the integrity of who we work with and having fun doing it is kind of the only thing that matters. Otherwise, everybody here can be at another investment bank, and it's pretty much commoditized that everybody's really good at what they do in this industry and everybody's really smart.

William Gladhart: 7:50

Yeah, no, I think that's a great point because we work in very similar industries to yourself with culture and building that for leaders, or actually to help drive value in the company. We see that it does make a huge difference in not only the attitude, but also the financial performance of the organization. And how people show up. People have the same vision and mission, and you don't get 10 different answers of what we're doing here. You get the same answer, and that's really driven by the leader yourself. So it's been our experience that leaders tend to struggle in three key areas people, process, and profit. And your role as a CEO. Could you identify which of these three areas or combination thereof, because they usually are, has been a cultural challenge as you built your organization. What was it? People, profit, what was the third one? People, process, or profit.

Matt Plooster: 8:36

People, process, or profit. People for sure. It's a people business. We're in a human capital business, we're in a service business. It sounds basic and maybe a little bit cold, but the way that you scale a human capital business and an investment bank in this case is people. And getting the people piece right is absolutely almost the not to be not to overstate it, but almost the only thing that keeps me up. When you're a business owner and you're managing cash flow, at some point it just kind of becomes paper, right? And you kind of become numb to the swings of cash flow management, et cetera. And candidly, I don't get me wrong, self-financing a business is stressful, but you learn to I'm a very I'm a faith-based person, and so you trust that and you believe in yourself and you believe in your team. But boy, when there's a people issue, and if you care as a leader, that's what keeps you up at night. That is the only thing that ever really gives me anxiety, et cetera. And getting that right is so critical, but so hard. And candidly, we're still, even though I, you know, we're ink best workplaces, and people here say I love you. I mean, all the all the things that are really such a huge blessing, getting that right is a huge, huge challenge. We're going through that right now. Like we're we're scaling the business. I'm 44, very much want this to be uh, I'm not building this to exit, I'm building this to have impact and provide opportunity for our people and create service for our clients that need it. It's important work. But getting that right and that push pull between being just fanatical around culture and the values and the fit of your people. Right. You know, that's a that's a tough, that's a really tough balance. And candidly, I'm struggling with that right now. I think we're struggling about it. And if anything, we've heard to the side of like being too disciplined versus taking the bait because we could go out and hire 10 senior bankers for the next 30 days and add 30% to our growth. But boy, if we get two of those wrong, it is hugely disruptive.

William Gladhart: 10:20

Yeah. No, I think you're pointing out a great point. Uh we've seen it in uh MA quite frequently, as probably were yourself, where you bring in disparate cultures, you bring in different leaders, you bring different styles to the table, and it either makes or breaks the organization or you start to see profitability drop off, you see performance drop off because no one understands what their role is or a lack of clarity. So I think you identified very well that it's a continuous struggle for leaders to not only evaluate that, but to look at the numbers behind that and continue to say, are we on the right path? Are we being self-reflective? You know, when you kind of think about those challenges along that, was there any particular event that either negatively or positively impacted your organization, either around culture, performance, or something that you could share with other leaders that you really had to work through?

Matt Plooster: 11:10

I think maybe it's more about a couple of things I think that are impactful that we do do, that we figured out the hard way that kind of came from some friction, which is we eight or nine years ago instituted a success coach that we employ for not just ourselves personally and professionally, but for our business to really say, okay, look, you need to be excellent investment bankers here, but we also want you to come here to be incredible husbands and wives and mothers and fathers and really investing in our people at all levels, not just as you're an investment banker, what's your fee pipeline look like? And how are you going to go find more deals? We also have a corporate chaplain on staff to be there for our people in times of need because inevitably we're just a bunch of people like any business doing life together, and people lose parents and people get cancer and have miscarriages and I mean just all the things that happen in life. And being intentional about investing in the soft stuff, which is so foreign in our industry. Yes, it is. People didn't talk about people didn't talk about all those things. And then not to say we're homogenous. I mean, we have atheists and Christians and we have people of all both sides of the aisle and politics, all the things, which is beautiful. It's a beautiful thing, and it's a good mission. But being very intentional and slowing down in a very fast-paced industry to really focus on our people and investing in them and allowing them to be people has been something that's very different, I think, for us culturally versus others in our industry. And not to say that I'm 44 and have the old world figured out, but boy, for us, there's been a lot of magic in that. Um because people want to, I think more than ever, probably especially versus when I started my career, people want to have belief in what they're doing, who they're doing it for, why a purpose in a very different way than I think even 10 or 20 years ago. That's really been, even though it has the why of that whole effort hasn't been to do more business than revenue or profit. I think our clients select us because when they're in the room with us and our people, they feel that. They feel that we love each other, we believe in what we're doing, we're passionate about it, we're passionate about our core values of being honesty and integrity always and all the other things. And it actually has absolutely impacted us in allowing us to recruit more people and better people and also getting better clients.

William Gladhart: 13:16

Yeah, I think that's a great point, providing not only of that support for the human events that happen, because inevitably, as we go through life, I mean, just stuff happens. I mean, we can't avoid it, life, death, etc. But having that backup, that resource, I think is huge. And we've certainly noticed in the private equity and MA industries that over the last five years, specifically the last three, that there's been this shift all of a sudden back to, well, it's not just about the numbers. We have value in people. And we have value in the people and not only in the companies that we're buying and selling, but the value of our people and the inherent knowledge of who's sticking around to continue to grow and do these deals because it's not just the guy working 80 hours a week, because I know a bunch of them, and they're like 30, 35, and they're out of the industry. One of them runs a construction company because he's like, I couldn't do it anymore. I wanted to do something totally different where I hung out with people and helped transform their homes. And I was like, okay, you're just doing a different way to do that versus transforming a business or transforming something financially. So, Matt, thanks so much for your thoughts. As we kind of wrap up today, is there anything else you'd like to share or add for fellow leaders?

Matt Plooster: 14:27

I don't think so, other than I don't know about other leaders who might be listening, but running a business, being an entrepreneur is so acute and so intensive that I often struggle to just step back and appreciate the journey, which sounds so basic, but I think at least me, I'm an OCD entrepreneur, right? It's like, what can we do better? What's a problem, et cetera? But man, what a blessing to be able to be a leader, right? And to have people trust you and to be able to serve them. And so if anybody's listening and having like I am a lot of times in the car on the way to work and I've got a big day and I'm worried about a bunch of stuff and I put on a podcast, maybe just an encouragement for whoever's listening to to slow down and just take in what a blessing it is to be in the spot that we're in, because I know some days that I do a good job at practicing gratitude for where the Lord's put me, but that's not every day. And so if somebody's having a rough day or maybe feeling like they need uh some perspective, what an awesome journey that we're on and what a blessing it is to be a leader and go have a great day for your people.

William Gladhart: 15:21

Well, I think that's awesome advice, also in light of the fact that we collectively as entrepreneurs do all the things that would be technically classified as mental illness. So we always have to be mindful of those other pieces. So, you know, Matt, thanks so much for sharing a little more about you and your business and joining us on the Leadership Lovers podcast. I really appreciate your insights.

Matt Plooster: 15:43

Hey, thanks, Will. Go big RED.

William Gladhart: 15:49

Thank you for joining us on the Leadership Levers Podcast. Find all our Leadership Levers episodes on the Culture Think Tank website at www.theculture think tank.com or listen on your favorite streaming platform. We'd love to hear from you about the challenges you have faced as a leader. Tune in weekly as we invite leaders to share their experiences in strengthening culture and performance one action at a time.