Kids These Days: Perspectives From New Graduates

Kids these days. As a 57-year-old adult, every time I hear that I stop listening. Because as a professor, I have found this following generation to be simply outstanding. And I am proud to be joined today by two fellow University of Missouri alumni, Trey Lucas, and Truman Webb. How are you? Thanks for being on.

Trey: What’s going on, Stewart? We’re happy to be here.

Truman: Thanks for having us.

Stewart: Absolutely. And when we send over, we talk about bullet points on these podcasts, and you guys have questions for me, which is a first. This is our like 80th podcast and nobody ever asks me anything. So this is great. Alright. So the way that we start these podcasts is always the same. Trey and Truman, here’s the deal. First three questions. Hometown. First job. Fun fact. Ready? Trey, I know you better. Let’s go.

Trey: So, my name is Trey Lucas. My hometown is Overland Park, Kansas. That’s where I grew up, was born and raised. What was the second question?

Stewart: First job.

Trey: First job. Are we talking internship?

Stewart: Anything that you got paid to do first. Whatever that was.

Trey: Okay. My first job was I was a freshman in high school and I started working at Waterway. It was a car wash.

Stewart: Car wash. There you go.

Trey: Oh yeah, selling car washes.

Stewart: All right, and fun fact?

Trey: Fun fact.

Stewart: Oh, here’s a fun fact. You two have known each other since kindergarten.

Trey: Correct. Yeah, Truman and I are actually best friends since kindergarten, and we were able to somehow come together during our last semester of college and live together. So it kind of came full circle.

Stewart: That’s so cool. Okay, Truman. Same three questions. Hometown. First job. Fun fact.

Truman: Got it. Hometown, same with Trey, Overland Park, Kansas. First job, I bused tables at a local Mexican joint called José Peppers. And fun fact, I climbed Mount Kilimanjaro in February this year.

Stewart: Oh, wow. That is a great fact. There you go. All right, so you two have graduated from the University of Missouri this past spring semester, right? Is it just this past one, ’22 or ’21?

Trey: So we just graduated in December, actually.

Stewart: Oh, in December of ’21?

Trey: Yeah. Yep.

Stewart: All right. So, one of you went into the insurance industry. One of you has gone down the investment banking path. How did you decide to do that? Starting with Trey.

Trey: So I feel like this is a pretty common answer amongst people within the insurance industry. It’s that they weren’t actively seeking insurance, it just found them, and the same applies to myself. So I was about a senior in high school when I guess this started. I was dating a girl at the time and her dad seemed to be doing something right. And so I was just constantly, “Hey, I’ll do whatever I can. You think you can employ me?” And he was always kind of like, “Oh yeah, whatever.”

And then two years later I ended up becoming president of my fraternity. And I think that changed things. I was also dropping my resume off at a few houses that I thought were pretty established like, “Oh, what does this guy do?” I would love to somehow just talk to him. I’m not asking for a job. I’m curious to what it is that they did. And I believe he heard that, is what I was told because I was doing it like three times a day for a week and was told, “Hey, you probably should refrain from doing that anymore.” But, it ended up-

Stewart: You know what they call that Trey, they call that initiative. That’s initiative.

Trey: Yeah. Someone else also said ‘stalking’, but ‘initiative’ is better.

Stewart: Initiative. Yep, initiative.

Trey: But he ended up referring me to my current boss now and just said, hey, he was also a former Mizzou finance major. And ended up emailing him, having a talk, had two internships with Amwins, Kansas City. And now I’m fully employed there and started on January 4th.

Stewart: Is it Amwin, or Amwins?

Trey: Amwins. A-M-W-I-N-S.

Stewart: And it’s an insurance brokerage?

Trey: Wholesale insurance brokerage. Yes, sir.

Stewart: Very nice. Okay. Truman, you man. You were a finance major at Mizzou. I was a finance major at Mizzou. The guy that taught me ECON 51. Is that still a class, ECON 51? Do they still call it that?

Truman: They may have changed the numbers.

Stewart: Yeah.

Truman: Yeah, they may have changed the numbers, but I’m sure it’s still a class.

Stewart: So the guy that taught me ECON 51 was a guy named Walter Johnson. And what I went back to Mizzou and spoke at the class there, the place I went, it’s like a memorial to this guy. That’s how long ago I went to Mizzou. The guy that taught me, there’s now a memorial outside of the building for him. So it’s been a while is my point. 

Truman, you were a finance major, you knocked the cover off the ball, and you’re now going to Stifel as an investment banker in the Fall. How’d you get there?

Truman: Yeah, it’s an interesting question. And definitely a story behind it. So in high school, I was really involved in my physics and my calculus courses. So I thought I could sort of translate that into becoming a mechanical engineer at Mizzou starting in the fall. But all that changed when an older member of my fraternity introduced me to an organization at Mizzou called the University of Missouri Investment Group. It’s a group that focuses on placing Mizzou students into Wall Street careers, like investment banking, private equity, venture capital, asset management, hedge funds, et cetera.

And so when I first went to the group’s first meeting, I really just had an eye-opening experience, what investment banking is and what these careers were. Because before that, I had no idea. I didn’t even know what investment bankers did. I didn’t know anything at all. So I changed my major from mechanical engineering to actually, accounting. So I’m not in finance, but I took a lot of finance courses through Mizzou. And so I instilled this four-year mindset where I knew I had to take certain steps of achieving my goal of becoming an investment banker post-graduation.

So I landed internships in a variety of fields like private wealth management, commercial banking, transaction services, and deal advisory for a big four accounting firm. Finally, this last summer, I interned at Stifel in their investment banking division. So I’m really excited to go back in the Fall, should be a good time. And I love my team, so it’d be great to join with them and learn as much as I can.

Stewart: I mean, that’s a very good summary, Truman. They call that initiative. You took the initiative. And look at the two of you. I mean, it’s great to see. I have no ownership at all at Mizzou anymore, but I still love it. And my real love is college students. Kids these days, they don’t want to work. Kids these days, they don’t want to do anything. Kids these days, they can’t get off their phone. It drives me insane. I look at people like you two and others that are so accomplished, not only in the classroom, but as human beings. I think that your generation has a service component that maybe my generation didn’t.

Can you talk about some things that you did outside the classroom, maybe even pre-college, that you feel like made a difference? I’m not talking about any sort of extracurricular activities that involved the consumption of alcohol or some other like pursuit, just to be clear.

Truman: Yeah. I can start with this. So my family is from a small town in Missouri, so we kind of come from humble beginnings and we understand how important it is to give back, be very recognizing what brought you to where you are. And so in high school, mostly middle school and sometimes in high school, I volunteered for my church youth band. So I played a lot of guitar for the band every Sunday. And I thought that was a good way for me to give back to younger kids, and I’d lead small groups and stuff like that.

And then going to Mizzou, the University of Missouri Investment Group, the group that kind of changed my path, my career path for the rest of my life, I then served on the executive board in my sophomore and junior year. And then I was president my senior year of that group. And giving back and making sure that each student got the same experience that I did, because it was a life-altering, really important group in my, I guess, professional development. And I wanted to make sure the group’s still surviving, still thriving, and growing because it is a very important group for me. And I think that a lot of students deserve to have a similar experience that I did.

Stewart: That’s terrific. When you came into the job market, it’s a pretty hot job market. The economy looks real iffy right now. The last time, in ’99, which is you two weren’t born. Is that true? That’s how old I am, man. That’s brutal.

Trey: We were one. We were one.

Stewart: You were one. Okay, great. I was born like the earth was still cooling. And so how did you find Mizzou’s career services, and did that help you get to your career now? Or was that your individual effort, some combination, parental connections?

I mean, it’s network, network, network, and that’s fine. But to your point, Truman, about other people having the same experience, my experience with underrepresented groups, in particular, is that some of those networking opportunities, and I’m a first-generation college student from a small town. My grandfather was a carpenter, went to eighth grade. I didn’t know what investment banking was either. And I don’t think I figured it out until I was like 30. So how did you find your networking and what advice would you give yourself when you walked through the door at Mizzou?

Trey: I can take this one first, Truman. So, I knew coming into Mizzou as a student and not playing sport, I was going to be at a disadvantage, because I think student-athletes, they’re a full-time student on top of a full-time job. I was like, okay, I need to get as active as I can in whatever it is I can. And so that started with joining ATO. But then I also started going to the business school and seeing what organizations and clubs that there were within there, and just kind of diversifying myself as much as I could.

Stewart: Can I ask a quick question there?

Trey: Yeah.

Stewart: You’ve clearly taken the initiative, but were you scared when you did that? When you went into the business school, were you like… I mean, it was scary for you, I would assume, right?

Trey: Yes. Everything is scary. Getting on this podcast is scary, Stewart.

Stewart: Really? Come on, man.

Trey: You know what I mean? My hands were like this before.

Stewart: Oh, come on.

Trey: Everything is-

Stewart: I mean, people who listen to these, here’s the hidden secret. If you goof it up too bad, we can just edit it out. So just relax. Don’t worry.

Trey: Yeah, no we’re good now. It is hard to take the initiative and it is nerve-wracking. But, if you at least give yourself a chance is how I look at it. One, you’ll either learn that okay, that didn’t happen. How can I reassess it and change what I did? But if you never give yourself the opportunity to try something, even if it is nerve-wracking, you won’t know. And so that’s why I’ve always just like, all right, I’m just going to go out there, and if something works, it works. And if not, it won’t.

Stewart: What sport did you play?

Trey: I played basketball primarily.

Stewart: Oh, okay. For Mizzou.

Trey: No, no, no. No, no in high school.

Stewart: Oh, high school.

Trey: I wasn’t good enough to ever play at Mizzou, unfortunately.

Stewart: Yeah. Yeah. We share that. What I used to say to my students is it’s just as important to find out what you don’t like. Sometimes that’s easier, right? You go, “I don’t like that.” Like commercial banking, I was like, pass. It was just me. Nothing wrong with commercial banking, it just was my thing. And when Truman said you tried a whole bunch of different things, Trey’s advice is, hey, go to the business school, figure out what’s going on, and throw your hat in the ring with some clubs and whatnot. You did that. Anything else that you did on the networking side that you think made a difference?

Truman: So I think the most important thing about internships is, like you said, is finding out what you don’t like, as opposed to just finding out what you do like. And no knocking on my previous internships, but private wealth management wasn’t quite for me. Neither was commercial banking, neither was deal advisory. And I think that investment banking really found that sweet spot for me. And I think that going back to what Trey said about taking initiative and reaching out first to these alumni, you’ll find that Mizzou alumni primarily are very responsive to you. If you say in your subject line to your cold email, “Hey, Mizzou student pursuing a career in investment banking,” in the subject line, they’ll see that. And your hit rate is much higher than if you just cold emailed someone who went to like Harvard or Yale or people get thousands of emails a day.

So I think that Mizzou has done a really good job of building this pipeline of people who are now in these careers and growing in prosperity. Now they see that future Mizzou students are trying to do similar things, and they’re much more able to give back. I think that’s a common trend that almost every Mizzou student has.

Stewart: So did you guys have questions for me, seriously?

Truman: I definitely did.

Stewart: Okay. Go ahead.

Truman: My end goal is to start my own business. I’m not sure what it is yet. It may be something in financial services, maybe something completely different. I’m not really sure. I think that a lot of clubs I was in, like I was in a venture capital club at Mizzou, shout-out to ACE, the group is a student manager venture capital fund that invests in startup businesses in the Midwestern area. And being in that group, you’re able to talk to a lot of business owners and people who start these early-stage businesses. I think it’s always interesting to hear their story and how they got to starting a business because it is a really big leap of faith. I mean, it’s something that I am hoping to muster up the courage to do eventually in my life. But I’m curious, Stewart, for you, your story, and how you got to starting this business.

Stewart: It’s interesting. It’s a great question. I just had the opportunity to listen to Betsy Ziegler who’s the CEO of 1871, which is a number one rated business incubator in the world, based here in Chicago. And it was amazing to me, eye-opening. And I think that venture capital gives you an eye into the future, if you will. I saw some things in her presentation that just boggled my mind, and I think that’s exciting, and I get that. I wanted to run my own business too.

And for me, I kind of landed here. I kind of got shuffled out a little bit. Couldn’t find the right fit. I moved to Chicago, lost my job, and became a professor through the grace of God seriously, and had a great six years at, shout-out to Lake Forest College in Lake Forest, Illinois. And then had another year at Northeastern Illinois University, which is a wonderful school, and met a great group of students there.
And so, I was fortunate to do that. And while I did that, I had launched Insurance AUM, but and the publishing aspect I launched in the fourth quarter of ’17. I funded it on my own credit cards, you name it. And I hung it out there. I was about 60 grand in debt. And I hadn’t taken in any revenue. And I’m not making asset manager money when I’m doing that, because that was my career prior. And I was ready to quit. In, like, June of ’18, I was ready to be done.

And my wife said, “You know what? Just keep going a little bit more.” In the next couple of weeks, Wellington Management, Rich Kaufman called me up and said, “Hey, we want to take your top subscription. Send us an invoice right away.” And it seemed like they paid it in about a minute. That was the reason that we didn’t go broke and go out of business in the summer of ’18. I’ve told Rich that story with tears in my eyes, thanking him for what they did for us, and we’ll never forget it.
But I’m 57, and I’ve taken on a lot of risk, and this is not the advisable time to do that in your life. The time to take risk is when you’re you. Because you don’t have children and grandchildren and whatever to deal with. And I don’t mean deal with in a negative way, but they are definitely, from a business perspective, we have a responsibility to them. My daughter is actually younger than you both, and she’s getting ready to go into college.

And so, it is frightening. It is frightening but incredibly rewarding. People say, “I want to be my own boss.” And that’s great. And I said that too. “I want to be my own boss.” And here’s the problem. When you own the thing, nobody tells you when you’re stupid. Nobody tells you, “Hey, listen, that’s a terrible idea.” I spent the price of a Tesla generating a capability that frankly was just a failure. And what I’d often say to students, I mean, Amazon, everybody talks about Amazon like it’s a juggernaut, but they’ve done 60 acquisitions that failed. Companies don’t fail because they make bad decisions necessarily. They fail because they don’t make decisions, and I think, as an entrepreneur, you’ve got to be willing to admit when you were wrong, cut your losses, and do something different. The ability to be nimble will keep you alive.

But I think it’s also helpful from where you’re going into the investment banking business in particular. It will give you a vantage point to see different business models, how scale works, scale and operating leverage works, how businesses develop value and repeatable revenue, and the value of that, which is something that we’ve been able to achieve here.

So, I did it out of necessity, I did it out at drive. I’ve done things that were a flop, and some other things worked. I really want to make this point. has a phenomenal team of people. Lindsay Michaels and Glenn McLaughlin are two of the key people. Our designer, Angela. That team is an incredible team and there’s no way that you can do this alone. I think that another part of being an entrepreneur is recognizing what you’re not good at and stop doing it. Hire someone to do the things that you’re terrible at. But long, long answer to a simple question, but what’s next?

Trey: First of all, that was a really good answer. And I was about to start taking notes when I remembered this is recorded.

Stewart: Just listen to the podcast, man.

Trey: That was awesome.

Stewart: Oh, thanks.

Trey: As similar to Truman, I’m inspired. I mean, I hope one day I’m able to start up a business of my own as well. Again, I have no idea what that is, but I’m sure I’ll be inspired some way down the road. I do have a question for you as well.

So, with everything you know now and everything you’ve been through in life, because there’s ups and downs always, if you were 23 years old again, which is how old Truman and I are right now, what would you wish you would’ve known, or what would you do differently with everything you know moving forward amongst your career? Whether that’s in life business or anything.

Stewart: I think a couple of things. One, I would take more risk, and at your age, career risk, because you don’t have far to fall at this point. And, it’s a good time to do it. In life, you want to take on options that have limited downside and lots of upside. And those are looking at areas of growth. The finance industry has changed dramatically, and continues to change dramatically. I think you’ve got to look where the ball is going, not where it’s been. Betsy Ziegler said the other day, the slowest… And this isn’t as big a deal for somebody your age, but at my age. She said, “The pace of change that you’ll experience in your life will never be slower than today.”

Trey: Wow.

Stewart: And so there’s a lot of changes going on, particularly in finance. And I think you’ve got to be mindful of that as you pick a career. There are jobs and lines of careers that aren’t going to exist with the development of AI. I saw a mock-up of an individual who looked like a real person, it looks like a photograph of a person. It is a virtual psychologist that is available on your phone, and you can replicate that person, “person” an unlimited number of times.

Trey: That is wild.

Stewart: These are concepts that I could never have even conceived of. So, I think at your age you take a lot of risk and you look for things that have limited downside and a lot of upside. The other thing I would say is, and I think you’re doing this when you say, “I want to start a business, but I’m not sure what it,” is to hold onto the goal, and let go of the path – because you don’t know where the water is going to take you when you go through the rapids. You kind of want to keep your head up and keep navigating. But if you think about it like GPS and you set in your coordinates, if you see a sign that says “Fresh raspberries two miles down the road”, and you take that detour, no big deal. You still know where you’re going. It’s not that a detour or a change or whatever derails you from your long-term goal. So I think, take a lot of risk and hold onto the goal, let go of the path.

Truman: Yeah. I think something that I always think about is how it’s kind of a catch-22 in a sense, because when you’re young, your risk profile is much larger. You’re able to take more risk. However, you don’t really have the funds necessary a lot of the time. And then when you grow older, you have the funds, but the risk profile is much slimmer, and you have people you have to take care of and an established career you have to leave.

Stewart: Don’t forget arthritis. And if anybody who’s ever seen me, I’m gray as a schnauzer. Yeah. Tell me.

Trey: Truman and I got a lot of gray hairs coming quick.

Truman: Yeah, it’s been-

Trey: We’ve been stressed a lot.

Stewart: Yeah. No, I hear. Just wait. Believe me, just wait. But yeah, it is true. But, when I’m talking about risk, I’m talking less about investing your capital as I am… For example, I would have been terrified to pack my bags and move to New York or Chicago when I first got out of school. I wanted a safer option. Because, I didn’t, frankly, think that I had what it took to be competitive. And what I would tell you is to have confidence that you do. And if you haven’t had the experience directly, that you’re smart enough to figure it out. And this is particularly true for females.

There’s a woman named Margaret Milkint who’s been on a couple of podcasts with us. She’s a dear, dear friend, and does a lot of work in diversity, equity, and inclusion. She’s a global leader in that field. And she said that a male, if they have 75% or so of the qualifications, they’ll apply for a job. And females sometimes will have more than 100% of the qualifications and won’t apply for it. So, I think it’s put your chips on yourself and take that sort of risk as opposed to investing capital. I’m talking more about taking a leap of faith that you are more capable than you may think you are.

Trey: That’s a great point. I can kind of go off of that. When I was a sophomore, so it would’ve been spring semester of ’19, when I was elected to become president of 155 man chapter at Mizzou. I mean, I had leadership from sports, but I was asking my grandpa and some mentors, I’m like, “All right, how do I?” And they basically just said, they’re like, “I mean, you were elected for a reason. And so that means people trust you. And you’re going to have decisions you’re going to have to make. And you’re just going to have to trust that what you’re wanting to do is going to be ultimately the right way.” It’s trusting your gut feeling over your heart because it takes all the emotions down. It’s like, this is what I think is right, and kind of doubling down on yourself.

Stewart: Yeah. And I do think that another great piece of advice is: don’t push through that pit in your stomach. I would say follow your gut. Your gut’s right way more often than not. But, believe this or not, we’re at the end of this podcast because people will be like, holy cow, these guys are going to… The last thing they want to do is listen to me, man. Believe it.

So, I want to say thank you very much to both of you. I’d love to have you back on. Congratulations on graduating in a really tough environment. Nobody needs to talk about how ugly COVID was for college students, but you had an atypical college experience, which is too bad. But it’s great to see you both out and doing so well.

Trey: Stewart, thank you for having us on. We’re very appreciative. We had a lot of fun. I would like to say one last thing. Even though college kind of took a detour from what it was to how it changed, Truman and I still were able to make the most of it and have a blast. I really don’t think either of us reflect on our college experience and say, “I wish it would’ve been different,” because I think we both really enjoyed how it went.

Truman: Definitely, definitely. Thank you so much for having us on, Stewart. I really appreciate it.

Stewart: My pleasure. Let’s end this in the right way. M-I-Z…

Truman: Z-O-U.

Stewart: I love it.

Truman: Let’s go.

Stewart: All right, man. Go Mizzou, go Tigers. Let’s wrap it up. Thanks for being on, guys.

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