Check out our latest 60-minute chat with Tim as he discusses life events, his start in the business, and the passion it truly takes for what he does every day.


[00:00:00.300] – Tim Clepper

Hey, you know, I think everybody’s different, man. I mean, I think it comes down to, you know. Here’s the here’s the long and the short of it is if you don’t have something that guides your life that isn’t lik like money or material things or, you know, just just stuff, if you don’t have, like, a purpose of your life that you and something that’s kind of like like a magnet pulling you towards it, then, you know, you’re setting yourself up for failure.

[00:00:33.660] – Tim Clepper

I truly believe, like, whether it’s spiritual or whether it’s like, listen, I have to play tennis like I’m such and I’m not. But I’m saying, like, you have to have something that you do that is outside the scope of just business or being a parent or being like a friend. Like something for yourself that gravity pulls you, makes you a better person. And, you know, for us and it’s always been the case. I mean, it’s just been, you know, this spirituality that we’ve had and I’m not please don’t mistake.

[00:01:02.910] – Tim Clepper

That is like I’m this crazy spiritual, you know, lighting candles. And that is not me. But it is just all about like, I think having a backbone.

[00:01:11.790] – Aaron Calafato

Are you an optimistic guy?

[00:01:13.320] – Tim Clepper

I would say on a scale from one to ten, I’m probably 100. That’s probably my biggest downfall. But it works, man.

[00:01:19.530] – Tim Clepper

I mean, I think optimism in all cases wins the fight. In all cases,

[00:01:27.820] – Aaron Calafato

Do you have to force it, sometimes? You don’t have to force it?

[00:01:30.550] – Tim Clepper

I never force it. Totally listen, I’m good at, like, four things, right? And one of those four things is being optimistic. It was I was born with it. I’ve groomed it. I’ve worked years and years and years in therapy and counseling and you know, about like how to use some of the talents that I have had of which are limited and really kind of, I would say, learn how to control them. But I’m a crazy, opportunistic person, an optimistic person, and it’s something that we’ve had to learn how to manage. So for a long time, you’ve had for a long time, this

[00:02:12.480] – Tim Clepper

Is optimism, a skill that you develop or were you born with it?

[00:02:15.540] – Tim Clepper

I think you’re born with it. I mean, we all know there are people that are negative people right there. Either something happened to them where they were made to be negative or they were born negative. I don’t think people are born negative, but I think their circumstance might make them a more negative person. You know, I think I was born with a huge spirit and optimism and being an optimistic person. And so as I’ve gotten older and certainly as over the years, you know, we’ve experienced some really cool things like that optimism sometimes can just get unruly and you have to learn how to manage it. And just like anything else, like some people go and get a coach to help them with their golf swing or their baseball swing or, you know, their technique in jujitsu, whatever that is like. I’ve had a coach to help me with like that. Right? Not to become a more optimistic person and think about how many great things I can do. It’s literally to control the optimism. It’s the opposite of what you would expect.

[00:03:16.650] – Aaron Calafato

Yeah, that’s the opposite side of it. So if that’s one polar opposite, what is a circumstance that you’ve been through? Can you go into a tough circumstance in your life that’s ever tested that? Where you used it to heal or preserve.

[00:03:37.030] – Tim Clepper

I’m 40. I’m in my mid-40s. I’m going to be 45. And I think in everybody’s life, if you say you haven’t been through a tough situation in your life in your midmid-40s 40s, then you’re lying to whoever’s asking the question. I mean, I can give you a laundry list of them I’ve been through. I mean, personal injury, personal illness. My brother passed away from an opioid addiction seven years ago, almost to the day. You know, we’ve been through a lot. You know, I had a stroke 10 years ago. People don’t even know that. Most people don’t. But it almost killed me. And it’s something we’re through, like being optimistic and saying, you know, I’m not going to let that, like, stop me. I mean, I was in my early 30s when that happened, and it actually happened the same day it happened to Teddy Bruschi. And we’re like the same age, the football player. And it really freaked me out. I mean, obviously. But I’ll tell you what, if I would have said I’m done or I’m just not going to like. I’m not going to try to get better. I mean, I had to work my ass off. I mean, it was occupational therapy, physical therapy. I mean, I lost all my movement in my right arm, my right side of my face, everything. And we got it back within a year. And to the point now where you can’t really even tell unless you’re really looking at it.

[00:05:06.690] – Aaron Calafato

What do you credit that?

[00:05:08.560] – Tim Clepper

I mean, and you’re just asking me a simple question. I don’t go around preaching my story saying, like, well, I had a stroke and I recovered. I mean,

[00:05:16.020] – Aaron Calafato

that’s incran edible story.

[00:05:16.830] – Tim Clepper

But it is what it is. Everybody’s got something right? I mean, but I will tell you, and I think this is the stem of the question, it was optimism and saying, like, I’m not going to let that hold me down, like we’re going to get better. And that’s how you get better. I do remember my physicians telling me, like it was the fastest recovery that they’d ever seen. We had great physicians from UH.

[00:05:41.100] – Aaron Calafato

And you think it’s that stuff that you can’t see, the optimism, the drive, the family support, all of that stuff. Is that the stuff that you credit to guide you through that?

[00:05:51.090] – Tim Clepper

No question. Yeah, but it’s yourself, right? I mean, it’s not like. You know. Your uncle or your dad or your mom, I mean, some people, obviously, but you know, or your wife or, you know, your spouse or whatever, but not to say that my wife was in a tremendous support. She was the one that actually found it, figured it out. At the end of the day, it’s you. And guess what that’s in life to. It’s you. You can blame it on any but like, oh, well, I’m not successful. Oh, I’m tired all the time. Oh, I’ve got diabetes. Whatever. Yeah. Change your life, change you diet, do whatever it takes and be optimistic and make a difference for yourself, which ultimately makes a difference for everybody.

[00:06:39.390] – Aaron Calafato

How important is accountability?

[00:06:42.250] – Tim Clepper

I mean, in one’s life, it’s all accountability. I mean, if you look at what it took, I mean, accountability is a great question. That’s a highly debated question. I mean, I would debate that, but I think that you have to be accountable 100 percent for your actions at all times, all the time. And we’re all human and we all make mistakes and you have to be in. But at the end of the day, certainly, even in my role as the president of the family office, which oversees wealth and business and relationships and finds new business and philanthropy, I mean, like. I represent a brand, so I have to be accountable not only to myself, but accountable to the brand. I mean, even the people in this room and the people I mean, it all boils down to what happens. Like what? How I represent myself. If I walked in here with, like a holey t-shirt, flip flops and jeans, that would change the attitude of how people roll around here. And we don’t do that. Obviously, we set a tone. Yeah, it’s called leadership.

[00:07:59.200] – Aaron Calafato

So let’s let’s go back at a time machine, preferably the DeLorean.

[00:08:03.010] – Tim Clepper


[00:08:03.520] – Aaron Calafato

And let’s go back all the way to your childhood.

[00:08:07.420] – Tim Clepper

Had a great one. Fortunate for that. I middle-classcame from a very middle-class family in an upper-class class town. So, I mean, I grew up in Hudson, Ohio, which, you know, we moved here in the mid-70s and I’ve been here ever since. Thankfully, my dad was in the trucking business, worked for yellow freight. My mom worked at home taking care of me and my brother, who has, you know, subsequently passed away, but my parents devoted their entire lives to me and my brother, my mom especially. And my dad traveled this like a lot of people’s dad does that, you know, until probably I was in high school and he took a job, well stayed with Yellow Freight, but was working with the company that or working managing the office here in Cleveland. So he didn’t have to travel as much. But, you know, I came from I would say very, very a very, very fortunate situation. OK, good. The town of Hudson, I have I mean, like my parents,  I mean, my dad was in a trucking business. I mean,  I did not grow up a rich man. And my dad was the son of the one of the guys that worked on the Redding railroad, my grandfather. And I never knew my grandfather on my mom’s side of the family. As a matter of fact, my mom’s side of the family was Mennonite up until, you know, she was, I think, nine or ten. So we didn’t really even know that side of the family. There’s certainly some cousins that our dear cousins, friends and family of mine that on that side of the family. But most of us on my dad’s side of the family. Came from no money. I mean, my dad had to steal like food from, you know, when he was in high school in order to eat.I mean, like, you know, you talk about some of that stuff. So where our families come and he  wanted, you know, to make sure that his two boys had a better life than he had, although I think he had a fun life playing in the woods growing up as a kid, which they were able to do. I had an amazing family, amazing mother, amazing father. I started dating my wife when we were in ninth grade and we stayed together ever since. So my wife of 20 years is my high-school sweetheart. How weird. It’s weird, right? But today’s day and age. But is what it is and it’s a byproduct of just having she and her family totally amazing. So I grew up in a very fortunate situation, not necessarily financially fortunate, although I will tell you that living in Hudson, I got to be around a lot of people that had a lot of wealth and I got to see that. And I think that was one of the things that made me say to myself, you know, I’m going to work really hard. I’m going to go I’m going to become what I want to be. And I can tell you that’s not going to be, you know, in a like physical labor job. I mean, I want to learn, go to school and make a difference for something. And I don’t I didn’t know what that was obviously at the time. But, you know, it was living here in this town and having the family that I had that put me in the situation we’re in today, which I would tell you is an incredibly fortunate and I’m incredibly thankful for our situation today.

[00:11:37.820] – Aaron Calafato

So going back and looking up, if you could even just assess your own self. Yeah. Time you see the value of hard work. Yeah. You see. , your mom does in the home, you see. Yeah. Just on the road. Yeah. You know what it is to be working class. You see that you’re a part of that. You see the benefits. Hard work. But then you also see the outcome of not only wealth but you know, the American dream per se. The ability to be able to work hard and then that that becomes achievable to you. Do you think that’s maybe what sparked your interest in finance and in the work that you do now?

[00:12:10.180] – Tim Clepper

Yeah, I mean, so I’ll walk you through it. Right. So it and I learned this from my dad, right and my mom. But like, hard work pays off. Right? And sometimes I mean, I was up at five o’clock this morning exercising. If I didn’t exercise, I would weigh 400 pounds. I’m telling just because I love to eat a lot, but like I burn a lot and like I’m burning my candle burns. Right. So even this morning, the person that runs the class that we work out in said you don’t have to worry if it’s working or not. You’re here. It is working. Just keep doing it. Don’t fall off the rails and stop. And so from a very early age, I’ve always had to work and people that know me that would ever listen to this would say, well, Tim, I, Tim, when he was thirteen, worked for me. Whether it’s washing dishes or putting in a concrete driveway. I mean, I operated the sledgehammer in between my senior year in high school and freshman year in college in a concrete construction company. I mean, I’ve done pretty much everything, but I really realized that hard work and if you keep your head down, you can become something that perhaps you’re not right now. Right. I think, you know, I think I was born to do what I do today, but it’s taking a tremendous amount of training, a tremendous amount of just education, and not only in a classroom, but also on the street to get to where I am. And you can get there by just continuing to work, keep your head down and know that it’s going to work out for you. Like, know, like have the conviction that as hard as I work and as much as I put in, I am going to get it out. And if you think that way, you’ll get it.

[00:14:04.480] – Aaron Calafato

You know, it’s interesting for me, it feels like it’s a great equalizer. People start from different perspectives, right? Doesn’t mean the outcomes are always going to be the same. Yeah. Like anybody, no matter what your socioeconomic status, no matter where you’re at, if you work, you can achieve gains from that. There’s no question. I mean, and that’s a beautiful thing, right? There’s no entry country club pass to get into that. Everybody, if you are able them can do it.

[00:14:29.830] – Tim Clepper

You know, it’s funny. So I started at a company called McDonald and Co. as a stockbroker in the mid-90s, and that doesn’t even exist anymore. I mean, I literally used to call people at their house or at their office and sell them stock and they had no idea who I was..

[00:14:45.880] – Aaron Calafato

Cold call, cold call. The coldest of cold. The coldest of cold! I’m freezing.

[00:14:49.700] – Tim Clepper

Aaron, my name’s Tim Clepper. I work for McDonald and company I’d like to talk to you about three things.

[00:14:55.180] – Aaron Calafato

What’s that?

[00:14:55.930] – Tim Clepper

And that’s what I was trying to get you to say. Right. And I did. And that’s what you did.

[00:14:59.740] – Tim Clepper

And I learned how to do that. And here’s what I learned. If you do a hundred of those phone calls a day, you will be successful. It’s the math. It’s volume. But if you do ten, you’re not. So I got an opportunity to work for a company there that said if you do this, by the way, I’d figure that out. But if you do this, you will be successful. If you don’t do this, you will fail. And I did it and became successful. And that’s what I love about sales. Sales is repetition. Being able to take no for an answer or not taking no for an answer, but being able to hear no and keep going and keep going and having faith and being opportunistic and optimistic. Right? Which all we’re talking about all ties in together and sooner or later, somebody is going to say what they’re going to say, yes, I remember the first time somebody told me yes in a sale.

[00:15:52.740] – Aaron Calafato

How did that feel?

[00:15:54.570] – Tim Clepper

I was like I was so not used to hearing it that I didn’t know what to do!


It is the craziest thing. And if anybody is listening to this, it’s a salesman. You know what I’m talking about? Because it’s like the first time somebody says yes to what you’re selling, though, you’re like, I can repeat that. And so you might even go on a like a losing streak, but you get addicted to that. Right. And then you go out and get and that’s what makes you a crazy, great salesperson and anybody associated with know like it’s the addiction to that person saying yes again. Right. So if you really boil it down to my very essence, like that’s what I fell in love with, that put me into the situation we’re in today. I fell in love with sales and then realized that really what I fell in love with was the fact that I could create relationships.

[00:16:48.540] – Aaron Calafato

So at the end of the day. Hmm. Talk to me about relationships. Yeah. Why are they your super power?

[00:16:54.420] – Tim Clepper

All right. So first of all, it stems back to when I was a younger guy. I would say probably even in high school. I remember one of my best friends and his dad actually was the CEO of a publicly traded company. And we all looked up to him. Right. And this is one of the people like I got to hang out with while I was a kid growing up. But I mean, certainly that wasn’t my my family, but it was fun.


And it and when you’re the CEO of a publicly traded company, I mean that you’re at a different level. Right. And he said, Tim, I remember you stand in the kitchen. He said, I’ve never seen anybody that could grow relationships like you like. And he said that. And I don’t even know. I forgot I was probably junior. I don’t even know how old I was. But I was like I took notice to it. But then I was never the person in high school that was a clicky. I’m not a clicky person. Anybody that knows me would say that. I have a lot of friends and a lot of different circles and that and as we continued to kind of grow that, I realized that it was relationships like that’s that’s what I do. I mean, I am my relationships mean more to me than anything. Well, I can’t. I mean, obviously, my children and my family and all that, my wife. But my relationships mean more to me than anything in the world.

[00:18:15.590] – Aaron Calafato

You mentor a lot of young people and have for a long time, it if you had a group of 10 folks getting into any type of sales, any type of sales, any type of sales. Yeah, but if you had 10 people right in front of young people in a sound bite, what would you tell them. I know it’s a little repetitive for you. What would you tell them about how important relationships are in terms of what they do? how would you guide them if you were to talk to you down of 10 of you when you’re 18 years old, what would you say?

[00:18:54.160] – Tim Clepper

I would tell you that maybe more differently than about relationships, because obviously they’re important and certainly if you’re going to be in sales like I mean, you have to be able to cultivate a relationship. But the one thing that I talk to younger folks about is figure out what your superpower is. Everybody’s got one, right? I mean, and you might not even know it and it might not even become present or apparent to you until you’re like later in life. But like every soul, every person, every human being has a superpower of some kind. And you have to figure out what it is and then you have to develop it, grow and turn it into your strongest you’re your greatest strength. You know, my partner and you know, one of my best friends and everything, Matt, Matt calling his superpower is leadership, I don’t think there’s one person that would say that Matt called superpower wouldn’t be leadership. It is leadership. I’ve never seen anything like it. That guy, like people will run off the cliff, right? That’s his that’s a superpower mine is relationships. So when I talk to younger people and help them and mentor them and there’s many, many, many of them and they’re listening to that, they would tell you that it’s like figure out what your superpower is. And it might take a lot of people to help you figure that out. Right. And you can figure it out really quickly when you’re in sales, because the crazy thing about sales is especially if it’s like 100 percent commission where you live by the sword or die by the sword, like you figure out real quick what you’re good at, right. What your superpower is. Look, some people have looks as a superpower, right? Some people have their energy as their superpower. Some people have leadership. Some people have relationships. Some people have their intelligence as a superpower. I can’t tell you how many times I’m in a conversation with somebody that I know is way smarter than I am. Like, I don’t even know it. I don’t even know my brother was like that. My brother was almost a PhD in molecular biology from Penn State University. That close. I couldn’t even talk to him like my senior year in high school because I couldn’t understand what he like. He was so smart. And that’s one of the things and I’ll caution people like that’s one of the things that he got stuck on these painkillers not to go down that rabbit hole, but that was to dumb the world down a little bit so he could be normal and feel normal. But this is seven, eight, nine years ago, and it wasn’t like it is today. And he just got stuck on them and that was it. So my point to it is figure it out right and then grow the hell out of it and then sell that right. And then whatever that is like, whatever you end up selling just happens naturally. It’s like a byproduct of it. Right. So. That’s how I would mentor somebody that’s new, that’s younger coming in, I’m going to meet with somebody that’s younger in 40 minutes in their mid 20s, and we’ll have the same conversation. And that person is charged to have a very big he’s a he’s got very he’s got a very big position in life right now for being a young 23-year-old person. And he’s coming in for that very reason, is I need some help. And so you mentioned people all the time, all the time. Yeah, why is that? Max Schindler has worked for me and with me as a partner since he was a freshman. And he went to college full time and worked with me full time. Why is it important?

[00:22:36.220] – Aaron Calafato

Why is important?

[00:22:38.830] – Tim Clepper

First of all, it takes a team. Right. And one of my one of the things I hate to hear people say is I’m a self-made man. I’m a self-made millionaire. I watched a show last night on Discovery, like about undercover billionaire, I think it’s called I Wanted to puke in my mouth and no offense, but like he’s talking about like I made it on my own. I call total bullshit to that. It takes a village. It takes a team. Unless you came up with a winning lottery number and you pull the ticket and it was just blind damn luck. There’s not one person that could say I did it all myself. Right. So that’s one of the things that I really mentor people is and that’s why younger, like not so much even younger people, but other people like you and like the people in this room and the people in our company, like I have to surround myself with those people because that’s what makes us all better. Right. Like I said before, I’m good at, like, four things. Right. But the four things I’m good at, I’m really freaking good at. Right. Lebron is really, really good at like four things. I think he would tell you the same thing. Right. But those four things he’s good at, he’s really good at them. Right. We’re not perfect. Right. Not at all. And we’re not trying to be. So I know what I’m good at. So I need to go out and find other people that have skills that I don’t have to become like the best we possibly can be as a group.

[00:24:17.230] – Aaron Calafato

So you’re cold calling back in the day. Was that in the 90’s?

[00:24:21.070] – Tim Clepper

yeah, it was a fun time. I’m surprised I’m still alive.

[00:24:28.810] – Aaron Calafato

Let’s talk a little bit about going from there and then now to where we are and where you are in the city. Take me on a quick journey, but also some nuggets about what that experience was like.

[00:24:40.240] – Tim Clepper

OK. Yeah. So I’ll start from the very beginning. Right. So. Football player, lacrosse player, I was very involved with my school, was very involved with my friends, I was just that typical high school kid, right. I wasn’t overly good at sports. I was good enough. But, you know, I was hanging. I like to hang out like, you know, I was a kid. My brother was crazy, crazy, talented, you know. You know, as far as he was brilliant. Right? So I almost grew up like. I didn’t get those brains, so like he’s doing so it’s OK for me to be like a C student, but then when you get into college, those things change and you need to be now. Now it’s on. Right now it’s time to be like, this is all you. Now it’s time for you to start a life for yourself. So I had to learn real fast that I had to work really freaking hard to get really good grades, which is what I did. And I joined a fraternity and everybody listening to this would tell you that there are a lot of nights that I spent in my dorm room studying and in order to get like a good grade on our algebra 2 test, which I’m not a crazy, great algebra person, just that’s not the way my brain works. But I was able to get through it and ended up graduating magna cum Laude at Kent and with almost a 4.0. Interestingly enough, I started a credit union with a group of guys, men and women at Kent State University. And it was one of the best at the time, had no idea what happened. But I basically started a bank for students at Kent State.

[00:26:16.890] – Aaron Calafato

Just like you started a credit union at your college?

[00:26:18.840] – Tim Clepper

Yeah, in the mid 90s. Yeah. And I was the investment. I was the vice president of investments.

[00:26:26.400] – Aaron Calafato

People were investing?

[00:26:27.540] – Tim Clepper

Well, here’s who invested. Other credit unions invested in us. We were federally chartered, state insured. It was the Kent State Student Credit Union in the mid-90s. And if you’re listening to this, I’m sure you’re smiling right now. But I went around other credit unions and said, you know, Mr. Smith, that X, Y, Z, credit union, if you give me a hundred thousand dollars, I’ll put that in a CD down in at the time was called Corporate One and I’ll pay one percent less than what I can get on it. Right? So in that one percent I would make that would be the money that we made in our credit to make money to pay, to get the things that we needed to have. So Carol Cartwright, the President University, gave me a place in the student center. I had a full-blown office. We had four fifteen student employees. I mean, people were getting college credit for it was just absolutely insane. But people used to say like, oh, like we’re part of an investment club in college. We’re like, this was I mean, I had a business card and a cell phone in the mid 90s. Nobody had that. How big was that? It was the size of a shoebox. Right. I think I kept it in a shoe box. Right. I think it came in a shoe box. It was a Tandy or a RadioShack cell phone. But I was one of the first people and I wanted to have it because two reasons. One, you had to look the part, right? I mean, who was I really going to call on dam cell phone in college?But to like I used it right. It was cool. So I started a credit union and that really. And so how I got into the investment business professionally is all through college. I was managing the portfolio that we built. Right? Not only did I have  find the money in order to like have money to lend to other like lend to students. But we also had to manage that. And we had examiners like, you know, like, you know, federal examiners that would come in and basically tell me what I can and can’t do. And they would audit that and govern that. No Internet. So you can’t just type it up. They would literally be looking through the newspaper and say, like, you can buy this bond and here’s the CUSIP number and here’s when it matures and that’s what you have to buy. And here are the three brokers that you can buy it from like they would just now. I’m nineteen, right? And so I would make those phone calls and I would I became a very good client of a stockbroker. Right? And and they couldn’t believe that I was a young college kid that was making $500,000 trades. Right. But I was so that’s how I got that’s how I got interviews to become a stockbroker. And I partnered up with a guy who was a great friend, continues to be. And he really showed me the way to kind of like work my tail off. And when I say that, I mean, like in the office on Sunday nights at three o’clock in the afternoon to about 7:00 every single week, and you’re making your call list and you’re figuring out what you’re going to say. And you’re doing your research because on Monday it’s game on, babe. Right? You got to figure that stuff out on the weekend. And so we force ourselves to work on Sunday night. You talk about hard work and dedication, all that stuff. Imagine telling your wife or your family or girlfriend or whatever it is. Hey, I know you’re sitting at the pool right now, but like, I got to go to the office and get ready for Monday every week. Right? So when I started in the investment business, I thought somebody was going to come into my office with wheel barrow full money and, like, dump it on my desk and go buy a bunch of fancy suits and call. Today, it turns out it was the worst paying, easiest job you could ever have coming out of college. Right? But it was the best paying, hardest working job you could ever have to, and you learned real fast. I had a phone book and a telephone go. So after you get your licenses, sell whatever we have, and that’s what we did and I got really, really good at it and became really partnered up with some guys and they got they were more like into this is really when it went we were started changing from like stockbrokers to some of these guys to get into things like as foreign as financial planning, like we were straight up salespeople. I didn’t even care if you didn’t have money, like I’m selling you stock. You had to pay for it or the police are going to come and take you out of your house. Right now, this whole financial planning opportunity was maybe more like that’s more along the lines of what I want to do. I really didn’t want to be. Yeah, it was like way I’m like, that’s what I want to be. I mean, I like selling, but like, I don’t want to be like that guy, you know? And at the time I was 22, 23.

[00:31:07.230] – Aaron Calafato

I mean, I was that is that life sustainable?

[00:31:09.540] – Tim Clepper

That was more I saw that as a more of a path, a clear path like I and then what happened was I made a partnership agreement with a couple of guys and you know who you are. And they all work with us here today after twenty plus years of doing it, which is amazing. But it came down to look you guys and this is critical. You guys are hyper good at what you do, financial planning. You guys are certified financial planners. You guys, this is what you do. You don’t understand insurance and trusts and estate and we have all these relationships. I’m a sales guy, like let me go out and find relationships and bring them back to the den, so to speak, and then we’ll work on them together. But like your for lack of a better word, you know, you’re that economist. You’re that planner. You’re that guy that sits behind a computer. Like, you have a hard time going out and finding these people. But in that business, like back in the back in the day, you had to find your own clients. So the smart thing that we did was I was the finder. Everybody else was the minder. And I got really, really good at it, like really good at it. So I was at McDonald and company through the mid-90s. I went to another firm. I started an office with a gentleman who has just had a spectacular career in the finance business for a company by the name of Robert Baird and Company based out of Milwaukee, Wisconsin. Phenomenal company. And then then I went on to really a bigger ocean, so to speak. And I worked at Morgan Stanley as a senior vice president, as senior portfolio manager in my 30s. I mean, we were good and we were crazy big. And then I realized, like, this is just crazy, like I’m not in New York City, like I love my relationships and I, I just need to get out. And start my own thing, and that’s what we ended up doing in 2015 after nearly. 15, 16, 17 years of building and building relationships and having people like want you to be successful, right. And having these great partners that you’ve done deals worth and plan for and helped out and done gone way above and beyond what your call of duty is. And those people want to see you become successful. And then I finally got to the point in my life where I was like, now’s the time. I’m in my late 30s. If I don’t do it now, my young kids like if I don’t do it now, I’m never going to do it. And I remember talking to my wife about I’m like, hey, I just want to chill, I’m leaving a monster company where I have a monster job and I am we’re going to strike out on our own. And she’s like, what? Like and by the way, we don’t have any insurance and I’m going to have to fund payroll of our checking account. So if you see big time, like, drops in our checking account like that, because I got to pay for all these other guys that have been my partners for like since Max. We talk about Max, right? I talk about Max all the time. He’s like my brother. Right. Like somebody’s got to pay for him. I mean, he’s not going to do it for free. So we took a monster risk. The biggest risk I’ve ever taken in my life and  it apparently has paid off crazy because if I didn’t do that, we wanted to start a company around starting family offices for people and then lightning struck. And I will also say this in everybody’s professional career, you can look back to having a unicorn moment or not having a unicorn moment, and it’s as black and white is that you either landed that if you’re an NFL agent, you either landed that Tom Brady or you didn’t. If you are a broker, if you’re a financial guy, you either landed that billionaire or you didn’t it. If you’re a hedge fund manager, you either did that deal and made billions or you didn’t. It’s black and white. It’s on or off. It’s binary. I met Matt. And. This is before, like the company was doing great. Don’t get me wrong, but Matt came to me and talked to me about like, hey, I’ve got some ideas around what I want to do in the company. And what do you think about him. And we were just friends and I had Mike. He didn’t have I wasn’t managing any money from that, as a matter of fact. We had no business relationship. We were just friends. And I will tell you to people that say don’t do business with your friends, I think is bullshit. I think you do business with your friends. You do business with your family, because when things turn shitty, right, you have at least a relationship that you can go back to and say, look, we got to work on this together. Right. Anyway, the point being that in 2015, I had a lightning strike and that lightning strike is that. Just on, just because of a relationship, because we are kids went to first grade together and we showed up at the parent teacher meetings as parents in like, you know, as dads that not all dads mostly are at work. And like, we would show up together. Then we became really good friends and just started talking and.The answer to what Matt was asking was bringing in a partner to help him, and that wasn’t me, but I was the conduit to bring that partner in which then just set the world on fire for all of us and provided Matt with just an unbelievable situation to not only have, you know, a really significant liquidity event, but also take his company, which at the time Leaf Filter to a whole new level. I mean, I’m talking about like thousands fold in terms of people revenue and everything else, offices.

[00:37:35.680] – Aaron Calafato

So you take this huge risk?

[00:37:37.450] – Tim Clepper

By risking himself. Right, so as growing Leaf Filter, it was all his money all the time, right, and that was one of the questions like, well, I want to grow, but like, how do you grow, if you like, every time you want to open an office, you’ve got to dig into your own checking account. That’s hard. I was just what are we to say? We just had that conversation. Talk to Amy Clepper about it. She knows it really sucks. And I don’t care how much money you have. I mean, it costs money to start new things. Right. And that was really the that was really the thought process that came around bringing in a private equity partner to bring private equity. Right. And resources into his business, which was just about ready to go over the tipping point. And it obviously has.

[00:38:27.320] – Aaron Calafato

So I want to bring this full circle to the last part of the conversation. But just kind of you take this big risk, right? yeah, but you’re optimistic, right? And then you land your unicorn. But it was because you developed a relationship.

[00:38:41.870] – Tim Clepper

But I wasn’t looking for it.

[00:38:43.190] – Aaron Calafato

No, you weren’t.

[00:38:43.730] – Tim Clepper

No. And that’s the thing. And you don’t ever you have to be a beacon. People ask me all the time, like, why do you do the social media? Why do you do like why would you do a podcast? Why would you be, why would you put something out there about yourself or why would you dress a certain way? Like the answer is you have to be a beacon. You have to show people that, like, you’re you want to do business, you want to build friendships, you want to build relationships. You want to be like in order to grow. And the more people you have right behind you, like the more people not behind you, but like as a team. Right. If you’re the quarterback, you have to be the beacon. And that’s what it’s all about. That’s why we do what we do so that we are known and when we go into a meeting, people aren’t like, well, who are those guys? Right, or who? That’s why it’s so important to be out there at this level. The point being. If I didn’t start at McDonald and company and I use that, it was a phenomenal place as a stock broker, selling stocks to people that were 40 years older than I was on the phone without ever meeting them before. Right? And then being able to do it enough to make money and stay at it and then getting good at it and then realizing you wanted to take a different direction and then bringing on people that were really good at that with like financial planning and doing retirement work and really helping people and making a difference and learning about their families and their kids and then taking and then getting into the big time working for a big firm with a big title and a big job and then saying, you know what? I have enough faith in myself, I have enough relationships now I can go out and do it myself and take a monstrous risk because if I don’t do it now, I’m never going to do it. And then all of a sudden, bang, like the reason why I did that was to meet Matt. I didn’t know it at the time. I wasn’t looking for it. It wasn’t anything. It just happened. It was a unicorn moment. And I would tell you that if I didn’t have that experience and go through that pain and go through those problems and go, I wouldn’t have known what he was. I wouldn’t know what he was talking about. I mean, I helped 15 entrepreneurs sell their company and you if you’re listening, you know who you are. Some companies were small a couple million-dollar companies. Some companies were big, 50, 100 million dollar companies. But I got really good at helping people do that. And so when I met Matt, I didn’t know who he was, but then because I’ve had I mean, I learned how to do it, it was meant to be the only way I can tell you about my relationship with Matt. And like, I know we keep coming back to it, but, like, it was just meant to be.

[00:41:53.640] – Aaron Calafato

I was reading in The Wall Street Journal, I think it was a couple of weeks ago, but they said that single-family office is the new Vogue or something along that line.

[00:42:00.420] – Tim Clepper

How crazy is that? I started at the bottom of the freaking pyramid? Right? And now we’re at the very top of the pyramid as it relates to the finance business.

[00:42:13.620] – Aaron Calafato

What is a single-family office?

[00:42:15.060] – Tim Clepper

A single family office is a private firm, tax, investments, business, legal for one family. For one family, for one, I mean, it could be the Rockefeller family, right? It could be the Kaulig family. It could be you know, it could be the James family, right? It could be. What’s happened is. So many people try to take advantage of the system over so many years and manipulated people out of money and investments, that the regulation of private equity and hedge fund and money managers has become so punitive that people are just saying, you know what, I’m done. I’ve made billions of dollars, I’m not going to do this anymore. And I’m just going to set up a family office and I’m going to hire a bunch of, like a company to handle my stuff. Right? So when you have a family office. You don’t like you build your own firm. And thank God I’ve had all this experience because if I didn’t, I couldn’t have done what we did right. Family offices come in all shapes and sizes. I tell people if you’ve seen one family office, you’ve seen one. They’re all different. But it totally is the pinnacle. It is the top of the absolute top of the food chain as it relates to, you know, the finance business in America. People would argue hedge funds. And, you know, well, I’m a hedge fund manager. I’m a well, but at the end of the day, when it’s all said and done and you don’t have any more customers and you don’t have any clients and you don’t have any other people, and it’s just you. You don’t have anybody you have the answer to. It’s just you that’s top of the food chain. You look around and there’s nobody to your right. There’s nobody on your left. There’s a single-member family office.

[00:44:22.470] – Aaron Calafato

You’ve seen a lot of success with this model. But then you’ve also said, you know, the more that you make, the more you can give. So let’s talk a little bit about the philanthropy on this. Why is giving so important?

[00:44:33.990] – Tim Clepper

Right. So. It stems back to this. There’s no such thing as being a self-made man. Right? People have helped you get to where you are today, I don’t care who you are, right? When you get to where we are, you’ve gotten a lot of help, you’ve gotten a lot of help from a lot of people and you’ve been through. Excuse me, but you’ve been through a lot of shit. I mean, if you think this has just been easy to get here, it isn’t right. It is super freaking hard. But we made it right. It’s time now to it’s time to pay the bills. Right. And that is helping others. That’s why I’m convicted by it. That’s why Matt’s convicted by it. We didn’t get here by ourselves. I don’t care what anybody says. Right. And there was. There is a lot a lot of people that helped now we did it like Matt and even a ton of the work, but it takes a village, so. I have just I am just 100 percent convicted in the fact that you have to help others and by helping others, that helps the whole system, right? The whole system. And as you get bigger and bigger and bigger, you have to help more and more and more. You have to do more. You have to do more. Right. And I think one of the great failures and I think why people fail is when they say, you know what, I’m going to shut the door, I’m going to go on a boat and then so. Not one person have I ever met and somebody could be listening to saying, that’s bullshit, but I’m going to tell you this, not one person I ever met that said, you know what? I had this awesome life and we grew it and we it was and we built this amazing company and we brought on these brands. We got it. And now we’ve got all this money and we’ve got all the success and we’ve got all the stuff going. So now I’m going to go into that room, shut the door, not come out for 20 years. Well, you’d be like, well, that sucks, I don’t know what to do. Like, you don’t want to go, like it’s time to go, right? Why would you do that? Right. There are people that end up doing that, but they ultimately end up saying to themselves I should never have done that. Right? I should have never just left. Right? I don’t have that same energy. I don’t feel it. I don’t feel alive. And that’s we’re not going to do it. So we’re actually going to go the opposite of that. We’re going to give as much as we possibly can to help as many people as we possibly can for as many years as we possibly can do it. Why? Well, because people have helped us get to where we are. We’re giving back. We’re doing the right thing, we’re convicted by it, some people might challenge that, but I always go back to it.

[00:47:36.360] – Aaron Calafato

You said if you can make one person’s life easier, you do what you have to do to do it. You told me that. What? Why does that what drives that? I mean, is that is that your faith?

[00:47:46.470] – Tim Clepper

I don’t know what the answer is that dude.

[00:47:49.740] – Aaron Calafato

Because it’s easy that there’s always these answers. But I mean, I’ve met you and we talked a bunch and like, I can smell bullshit. I know when someone’s like a liar or I can tell it, they’re just. Yeah, really, there is a conviction behind that. You actually care about the human soul.

[00:48:04.560] – Tim Clepper

It’s the soul. I mean, and again, please. I mean, it’s like. I’m not that.

[00:48:13.850] – Aaron Calafato

This Isn’t the 700 Club,

[00:48:15.630] – Tim Clepper

I mean, like I’m I am not perfect, I don’t want to be perfect. I’m not supposed to be perfect. I don’t, I’m just not. But I will tell you that I believe in souls. I don’t care who you are, I don’t care what you’ve done, I don’t care, I believe in souls and I believe in helping souls. I believe in instead of hurting them, Instead I believe in the opposite of that and I believe in helping them. So that’s it. If you can make a difference in one soul. Then. That’s that’s like. One 100 percent win right there, just one. Now, if you can make a difference in a bunch of them, then it’s just I mean, the energy around that is just undescribable. So that’s what we end up doing. And it’s all walks of life. It’s kids. It’s adults, it’s men. It’s women. It’s people that have I mean, it’s just. I’ve said this quote, and I came up with it and I’ve used it and I use it in our own charities, but it’s the healing power of giving. Right? And it could be you could it might seem like you have to have cancer, it’s just like if you’re having a bad day. And I give you this cup of coffee, dude,  take a minute. I brought you this. You’re like thanks. I mean, that’s cool. It makes your day. Right? So it’s a healing power giving. And I think that’s where we are right now, you know, and we’ve really built this amazing company, the Kaulig companies. And, you know, the tip of our spear is certainly the philanthropy and what we’re doing and I couldn’t be more excited about it. It’s growing like a weed.

[00:50:12.560] – Aaron Calafato

Can we end with some rapid-fire questions and we’re out? What advice would you give to your 18-year-old self?

[00:50:21.950] – Tim Clepper

Don’t quit.

[00:50:25.740] – Aaron Calafato

What is one mistake that you would want to take back?

[00:50:30.070] – Tim Clepper

Oh, man. One mistake that you would want to take back? Hmm, man, I’ve made so many of them, but and I’ve learned from so many of them. I would tell you that would you take it back or did they know you learn, you know? Well, I’ll tell you, you know. My brother got really sick. And I had to cut him out of my family to the point where he didn’t have a place to live and asked if he could live with me and my wife and our two newborn kids. And the answer was, I love you, but no. And I think that was a mistake because I look back at it today and I’m like. Oh, my God, if I could have just had them in there for another couple of years, I mean, I could have done it. I mean. You know, but it’s my brother, my only brother who I grew up with one year younger than me, I was born in 1975, he was born in 1976, March 17th, 1976. I was born on March 4th, 1975. So almost to the day we were one year apart, I had to make that decision. And now that was a mistake, I think.

[00:51:50.890] – Aaron Calafato

What is one piece of advice that you would give somebody getting into your industry?

[00:51:58.230] – Tim Clepper

Well, you can’t get into my industry like. I mean. I am the president and chief executive officer of the Kaulig Companies, which is like our family office, looks different than anybody’s family. I mean, some of the guts and the nuts and bolts are the same. But at the end of the day, it’s totally different

[00:52:19.810] – Aaron Calafato

If they see you as a beacon and maybe their end point is different. What one piece of advice would you give just to give them that push?

[00:52:27.970] – Tim Clepper

Yeah. Find people that are already doing it and go work for them, work for them, don’t do it yourself, work for them and learn. Right? You can’t just show up and do what I do for a living. It is all relationships. It is banks, lawyers, investment companies, real estate transaction, like so that takes decades to learn. Right. Let alone being able to protect wealth. This might sound different. This might sound bad or this might, like making wealth is not that hard. The whole TV show, Accidental Billionaire or whatever it was that’s on Discovery right now, he’s in 90 days going to build a million-dollar company. And just to show like, you can do that. Right? So it’s like making wealth isn’t that’s not the hard part. It’s keeping it right. So you look at the people that win these mega lotteries rate and three years later, they’re bankrupt. How did you make how did you win 50 million dollars and lose it all? Well, you don’t have the infrastructure in place to manage it. You don’t have the mental, you don’t have the financial. You don’t have the infrastructure. And that’s what we provide here to the family. Like the what we have at the end of the day, whether it’s marketing, whether it’s finance, whether it’s legal, whether it’s accounting, whether it’s bill pay, whether it’s fixing the freaking car, finding the people that do that, like that’s what we hear. We are all infrastructure. We are all support. We’re backbone to the family. And that’s that’s what you have to. So can you just get into it?  I mean, you could work here, but like to get to where I am, you have to go through many, many years of learning in different roles. God, that was a long answer. Can I say one other thing?  You just can’t be one thing either. I think in the family office of the future, the single-member family office of the Future. And we should do a whole nother podcast on this because I could talk about it for hours and hours. And this is one of the things that makes us unique. Most single-family offices, 10 years, five, 10 years ago were like, don’t tell anybody how we made our money and don’t tell anybody what we’re investing in because we don’t want to, like, have other people rush to what we’re doing. You know, it’s totally different now. Right. So we’re all it’s a generational shift. You know, we’re not John D. Rockefeller anymore. Right. Like, don’t tell anybody. We own this island down the Caribbean. Like it’s changed. Right? So we look at it’s the opposite of that. Right. So now moving forward, it’s like we want to be able to tell our story and evangelize that to use a spiritual word so that we can do more business, build cool things and help more people as a result of getting the profit. It’s a that’s why our infinity logos infinity. It doesn’t start or stop or that’s why our logo is the infinity symbol. Right. It just keeps going. There’s no end in sight. We continued to do business, we continue to make money no matter how much money we have, so we can help more people and do more things. Right? Interesting thought. Point being, if you’re coming into doing this and you’re going to try to be in trying to get my job someday, which can’t have. Learn a lot of different things. Right? Business. Arts, psychology, legal, all that stuff get you to where I am today, if you pigeonholed yourself and say I’m just an accountant or I’m just not. No offense. I mean, we need all of that stuff. But if you’re going to be where I am in the seat I am, you have to have all you have to have some knowledge and expertise and a lot of different things.

[00:56:43.040] – Aaron Calafato

If you could be born in any era. Yeah. What would it be?

[00:56:45.840] – Tim Clepper

I would be born exactly in 1975.

[00:56:49.940] – Aaron Calafato

Let me ask you again, because I think it ran over your sentence, so if you could be born in any era, what would it be?

[00:56:54.170] – Tim Clepper

Well, I’d be the product of a baby boomer. Like, I wouldn’t change what I’m doing, I wouldn’t want to be born in the 1920s, I wouldn’t want to be born today, I wouldn’t want to be I mean, I wouldn’t want to be born. And I mean, I. Mostly because I don’t know any different, but like, I’ll take exactly what I have.

[00:57:14.570] – Aaron Calafato

If you could pick any other profession, this last one, would you pick a different one, where you’re sitting?

[00:57:20.030] – Tim Clepper

I would not do. I was made to do this.

[00:57:24.870] – Aaron Calafato

Thanks for talking with me.

[00:57:26.130] – Tim Clepper

It’s been fun, I got a lot more to say. Yeah,

[00:57:30.600] – Tim Clepper

thanks, buddy. All right.

[00:57:35.640] – Tim Clepper

That was fun. Oh, they sounded great. Yeah.

[00:57:40.530] – Tim Clepper

So most people. You don’t ask them if they’re Republican or Democrat, you don’t ask them how much money they made last year. It’s just uncomfortable. It’s just not it. It’s not polite. Right. Like, how much money do you make? Well, it’s kind of like asking somebody that right, and they don’t want to you don’t want to tell. I mean, it’s like I don’t want you to think positively or negatively or indifferent, like so over that same mentality has transferred into that single family office world until kind of just recently, and maybe until we started changing it, we might be one of the most vocal about it. You know,

[00:58:33.350] – Aaron Calafato

That’s a positive thing?

[00:58:34.570] – Tim Clepper

Yeah. And when I say helping other people, too, and charity and like philanthropy, you don’t have to be sick. Right? You don’t have to like there are a lot of entrepreneurs that are saying, how do I what do I do? Like, there’s like that’s charitable. That’s philanthropic, right? I mean, we do a lot of stuff that’s not just helping that seven-year-old that has brain cancer go to the Super Bowl. Like, that’s part of it, but that’s not all of it, and I think people confuse sometimes people confuse the fact that, like, we don’t help people that otherwise would be just fine. We do, because that gets kind of cool,

[00:59:20.690] – Aaron Calafato

it’s more than cool.

[00:59:21.650] – Tim Clepper

Yeah, it’s different.

[00:59:23.060] – Aaron Calafato

Yeah, you talked about like don’t discriminate. I mean that not in the political or racial sense, but you don’t you’ll take conversations with anybody I think you said something like you never know, aunt whoever who has an ice cream shop, you don’t know what her situation is. You don’t know. It seems like you value that relationship first, that that relationship is paramount first regardless. And if it doesn’t work out from a business standpoint, it doesn’t work out because you’re not going to say no. Right. We’ll talk. Right. That’s cool. That’s different.

[00:59:52.340] – Tim Clepper

Yeah. Now we’re to the point, and I think everybody in this room even knows it like. But you just can’t like I mean, certain people can, but like it just we’ve gotten to the point now where you have to schedule the time. I want to talk to you. But you know that, Tim. I need 20 minutes, like it’s hard for me to give 20 minutes, my days just become scheduled, right? So but if you get on the schedule. I’ll talk to certainly anybody in our company and most people that are outside of the company. I’m not afraid of anybody stealing our trade secrets. Yeah, here’s our trade secret. Be a good person and work your ass off. That’s our trade secret. All right. Thanks, guys. Thanks.