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Moneywise

25 Aug 2026 · 48m · 18 chapters

Episode artwork

How a $1.5B Wealth Manager Spends His Money

In short

Glenn Ullmann, founder of Ullmann Wealth Partners (RIA), explains how ultra-wealthy clients should spend confidently through “wealth management = investments + advanced planning,” including wealth protection, tax planning, wealth transfer, and philanthropy. He also shares his own spending, aviation passion, and how he structures his firm’s client service.

Guest backgrounds

Glenn Ullmann founded the firm in Oct 2002; manages about $1.5B; owns ~20% after recapitalizing with partners. He left the Air Force at 29, where he pursued pilot training and later flew large military aircraft. He grew up in upper-middle-class suburbs; learned investing from his father and grandfather (Morgan Stanley account at 14; first stock: Sears Roebuck). He later worked at Smith Barney and then built his own RIA.

Key claims

Clients need a “life map” (values, goals, obstacles, professional team) to align spending with long-term security. People should enjoy money during accumulation, and philanthropy builds both confidence and community impact. He stopped worrying about spending above ~$20M net worth.

Notable examples

A client attacked in New York shaped her security outlook; “Melissa” invested systematically (from $100/month to maxing 401(k), then major travel). He cites using appreciated stock to exceed donation deductions and frames private travel using dividend/interest income (e.g., $80k trip offset by ~$30k/month income). He personally spends ~$30k–$40k/month plus philanthropy; owns a Cirrus plane (~$1.2M) and notes Cirrus safety features like a parachute system.

Written by AI. May contain mistakes.

Chapters

0:00

Introduction to Glenn Ullmann

Learn about Glenn Ullmann's background and the founding of his wealth management firm.

“Glenn Ullmann founded Ullmann Wealth Partners in October of 2002, which, as he pointed out to me, was almost exactly the day the market bottomed out from the dot-com crowd.”
0:51

Glenn's Perspective on Wealth Management

Discover Glenn Ullmann's unique approach to wealth management and financial planning.

“Glenn, thank you so much for joining Money Wise today.”
3:09

Growing Up Around Money

Explore Glenn's family background and how it influenced his financial beliefs.

“I mean, that's a huge spectrum of things that you've done professionally.”
7:30

The Decision to Join the Air Force

Understand Glenn's motivations for enlisting in the military and pursuing a flying career.

“I mean, having a Morgan Stanley account at 14 through your dad, you were stock picking.”
10:05

Transitioning from Military to Wealth Management

Learn about Glenn's career shift from the Air Force to becoming a wealth manager.

“So it was the easiest, most direct route to fly an airplane.”
12:41

Building a Client Base

Hear about Glenn's early experiences in the financial industry and how he built his client base.

“Well, I think the skill set is probably very similar.”
14:00

Building a Wealth Management Career

Learn about the journey of establishing a wealth management career from humble beginnings.

“So my first job was in Jacksonville, Florida with Smith Barney.”
22:10

Navigating Wealth: Personal Experiences and Client Relationships

Explore the balance of spending and investing for both professionals and clients in wealth management.

“people in the Hampton community all the time.”
29:18

Spending Philosophy as We Age

Learn about the importance of spending money wisely as we age.

“And as people get older, you know, I'm in my, I'll say early 60s, 63.”
30:26

Navigating Financial Fears

Understand the mindset of those fearing financial instability.

“Some people, based on their history, you know, my dad and grandfather's business didn't go out of business.”
Show all 18 chapters
31:50

Personal Spending Habits

Explore the speaker's personal spending habits and management techniques.

“And the times in my life where I have gotten, you know, we call it in the military and flying behind the power curve.”
33:58

Living Life with Purpose

Discuss the purpose behind personal expenditures in life.

“Or, and you can put an infant in it, but pretty much four.”
35:36

The Importance of Philanthropy

Delve into the significance of philanthropy in one's life and business.

“And so walk me through what your personal giving looks like and why that's so important to the way that you run your business.”
36:42

Passion for Work and Giving Back

Learn about the speaker's passion for their work and giving back to the community.

“It sounds like you had two liquidity events, if I'm not mistaken.”
41:10

Investing After a Liquidity Event

Discover strategies for investing after a significant liquidity event.

“When you say you like having fun, it's like, oh, no, no, that's like actual fun, like flying your own plane to and from.”
42:00

Investment Strategies for Recent Liquidity Events

Learn effective strategies for managing newfound wealth after a liquidity event.

“What would you tell someone who's just recently had a liquidity event?”
45:30

Reflections on Real Estate and Financial Security

Explore the pros and cons of real estate investment and financial security.

“And, you know, obviously this firm is private equity, but outside this private equity, a little bit in private equity, a little bit in private debt, a little bit in private real estate.”
47:54

The Value of History and Communication Skills

Discuss the importance of history and communication in personal and professional life.

“And anyways, Glenn, this has been awesome.”
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Transcript

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0:00Glenn Ullmann founded Ullmann Wealth Partners in October of 2002, which, as he pointed out to me, was almost exactly the day the market bottomed out from the dot-com crowd. Today, the firm manages around a billion and a half dollars. He owned 100 % of it. Now, he owns about 20 after selling equity to the partners who helped him build it. He left at the Air Force at 29 with roughly$200 ,000 to his name. And he stopped worrying about money somewhere north of 20 million net worth. He and his wife spend about$30 ,000 to$40 ,000 a month. Let's call it$500 ,000 a year. And that's not including philanthropy.

0:34He owns a plane where he flies himself because, as we already learned, he was in the Air Force. He loves flying planes. And he paid about$1.2 million for it. He loves to have fun, and he keeps most of his liquid net worth in a surprising place that I think you're going to want to hear. This is Glenn Ullman on Money Wise. I'm your host, Daniel Burke.

0:55Glenn Ullmann: Let's get right into it. Glenn, thank you so much for joining Money Wise today. How are you doing? Great to be with you, Daniel. I'm doing great. I'm excited to chat today and learn a little bit about what makes your unique perspective around money and some of the advisement that you do with ultra high net worth individuals unique to the show. Tell me about yourself. Tell me what it is that you do. Yeah, sure. I founded Ullman Wealth Partners back in October of 2002. That was actually the day the market bottomed from the dot com and 9-11 events. And we focus really on three things. We believe wealth management is managing investments and we manage about 1.5 billion of client assets.

1:33Glenn Ullmann: But that's really not enough. You can do a great job with investments but not have bracketed a client's advanced planning and professional relationships. You know, I say, you know, you can have returns of 100 % a year. But then if you don't have an umbrella policy and you've got your head down looking at your phone and you run into the back of a car with Melinda Gates in it and you do a lot of damage, it doesn't matter how well you've done because they're coming after your assets. So we believe in that wealth management is the investments plus the advanced planning. How do we increase cash flow, decrease debt, we're applicable, decrease taxes, always applicable.

2:16Glenn Ullmann: Wealth protection, how do we put a moat around a client's assets? Wealth transfer, how do we get those assets that a client or a family has built to the next generation? And or charitable giving, a huge part of our practice, philanthropy. How do we both explain it, teach it, inculcate it, one of my dad's favorite words, and so that those who much has been given, there's great obligation in our communities. And then we make sure that our clients have the tools and data performance reporting online and make sure that they have the best in accountants, bankers, state planning attorneys, personal attorneys.

2:58Glenn Ullmann: So we wrap that whole thing around the client. That's essentially what I've been doing since the early 90s when I stopped flying in the Air Force. But I'm sure we'll get to that later. Well, it's a great segue because I am curious, given your history flying in the Air Force, what was money like in the household growing up that you ultimately enlisted in the military and then started this wealth business? I mean, that's a huge spectrum of things that you've done professionally. That's such an interesting question. I grew up north of New York City in the suburbs. My dad and my grandfather owned a plastics consulting company.

3:37Glenn Ullmann: So, of course, I don't have a pen right in front of me. But if you were trying to make a million pens, you would contact my father and grandfather, and they would work as the middleman between you, the customer, wanting your million pens, and manufacturers. So I grew up, as did my siblings, going with my dad and my grandfather to injection molding factories around the tri-state area. My grandfather was an amazing salesperson. I remember going to an injection molding plant with him. And injection molding plants are loud. I mean, because you're stamping out plastic pieces from raw materials. And he had a robin egg Cadillac Seville.

4:25Glenn Ullmann: And I always loved that car because it had like the indicator lights. you could instead of it blinking inside like we do now it was like on the hood and they would blink I just love that car I know it's not germane to our conversation but in this car my grandfather had more tchotchkes and he knew in a factory of 100 people I remember he may not have but I remember him knowing everybody's name I remember him bringing these little gifts in one of them I have on my desk here in the office and it said, it's like this gold, it looks like gold coins. And on the back, you flip it over and it says, your friendship means more to me than a pot of gold.

5:11I love that. Yeah.

5:12Glenn Ullmann: So, you know, it was, and they trusted him. They trust, my dad was a different personality, but they trusted him too. So, you know, I was always, my dad taught all four of us, there are four kids, how to invest and the importance of investing. He retired in his mid fifties and lived off of his investments and my mom for the rest of their lives. Wow. And so he taught us, he opened an account at Morgan Stanley for me, I think when I was 14. So I, you know, delivered papers after school, after track practice, learned how to collect from nice people who tipped you and people who would stick their dogs on you.

5:50Glenn Ullmann: And I remember reading Ann Landers and hopefully that name, Daniel, you're much younger than me. Hopefully that name makes sense and reading the stock pages. So I think the first stock I ever invested in was Sears Roebuck. And that was at 14 years old? Yeah, 14. I mean, it was his account, but I was allowed to call his broker. But I also loved airplanes. I had a picture of a 747 cockpit And you can't see it in this picture, but on the wall to my right is a photograph of a 747 landing at LAX. It's huge. So things haven't changed very much. I was always interested in flying, took a couple of flying lessons.

6:31Glenn Ullmann: And where I grew up north of New York City, nobody from my high school had ever gone into the military. You know, that people went to the Ivy League, students went to the state university system in New York, SUNY, but I had never heard of ROTC or OTS. But my folks said when I was 17, hey, there's a school you can go to. And if you graduate, you can guarantee you're guaranteed to go to pilot training. So that's how I ended up at the Air Force Academy. Three days after graduating from high school, landing in Colorado Springs. And that is the best thing I ever did. I learned that the whole country is not Catholics and some Jews sprinkled in.

7:15Glenn Ullmann: Not all Caucasian like where I was from. It was, you know, it's the great melting pot of America. It goes to the service academies. So it was. It was the best thing I ever did. Other than marrying my spouse, it was the best thing I ever did. And so it sounds like you grew up around money. I mean, having a Morgan Stanley account at 14 through your dad, you were stock picking. would you say would you call that upper middle class or how successful was the business at the time yeah i think i think i would say upper middle class though we did go through a time in 1973 the arab israeli war arab countries embargoed the united states so we weren't getting oil that was the time of very high gas prices inflation was starting though it would get worse five years later.

8:01Glenn Ullmann: And my dad and grandfather's business was built on petrochemicals. I mean, that's where plastic comes from. So they went through a really tough time. In fact, I remember my dad wanted to move to Connecticut to get his taxes lower. And my mom let him look. And at one point he said to us kids, hey, you know, things are tight. We may need some money. And I said, well, dad, you can have my paper route money. And my younger sister said, well, you can have my babysitting money. My younger brother was like five. And then my older sister thought about it and said, dad, mom, I'm so sorry you're having financial difficulties.

8:41Glenn Ullmann: I'm going to live at grandma's house. So that was her solution. But yeah, I would say upper middle class. But then there was a time where things were super tight. But again, my dad and my parents, they had very Very diversified, but very good investments. And that's how we learned. All four of us learned the importance of owning equities, the importance of paying yourself first. I mean, how to balance a checkbook. I know my dad, he died in 97, but I think he was still balancing his checkbook until about 97. He used to send my sister, my older sister, off to, I'm a younger sister, to this grocery store for him in his later years.

9:26Glenn Ullmann: And he would always say if it was$9.50 and he'd given him$10, it's like, where's my 43 cents? So they used to say, well, Dad, we had to put gas in the car. So of course. So what was it about flying and the lifestyle, the excitement, the energy from going to the Air Force? You mentioned that had never really happened with peers in your high school. So you sound like you were one of the first in that area. Why did you decide to leave, other than the exception of the turmoil in that season of life, an otherwise very comfortable lifestyle to go into the military at that time? I just wanted to fly airplanes.

10:07Glenn Ullmann: That was it. So it was the easiest, most direct route to fly an airplane. If I figured out ROTC, I know I would have had more fun. But, you know, I got to fly, you know, the needs of the Air Force were constantly changing. So it used to be that you had to be 2020 uncorrected. The year I was commissioned in 1985, it was actually up to 2070. And I was 2070 when I got through pilot training. So I just, I've always been in love with airplanes. You know, we own a small airplane, a Cirrus. This is the airplane. And you fly that personally. Yeah, we do. We do. We're flying the G7 now, but we've owned a second generation, which didn't have air conditioning, which, by the way, is not a good idea in Florida.

10:58And a third generation. Not in South Carolina either.

11:00Glenn Ullmann: No, no, no. A sixth generation and just went to a seventh generation. They're great airplanes because they have now a dual safety system. If you lose the engine, you just pull a lever and a parachute lowers the airplane to the ground. Whoa. That has saved hundreds of lives since 2000, I think, when the first production airplane. Now we're up to, I think, 11 ,000 total airplanes. And now, in addition to the parachute, it's got auto return. You talk about technology. Auto return, if Glenn stops functioning, Lisa just pushes this button, and the airplane declares an emergency with air traffic. It talks to the passengers.

11:44Glenn Ullmann: It finds the nearest suitable airfield and lands. It's incredible. That is incredible. I mean, really. It is. I've never heard of that in my life. That is one of the coolest things I've ever heard of before. And the thing is, you know, when I was flying big airplanes, AWACS, Airborne Warning and Surveillance Airplane, Control and Surveillance Airplanes, we brought those airplanes back and forth to Saudi Arabia in the 80s. GPS hadn't been invented. Our navigator was taking what we call cell shots. He was seeing where the stars were so he could figure out exactly where we were over the North Atlantic.

12:22Glenn Ullmann: And today, most of us have never seen a map, right? It's all - Right, wow. How's Google say I need to get there? I mean, so tell me how you went from that. You flew for seven years, if I have that correct. Yep. And now you own an RIA wealth management firm. Walk me through that shift. Those are two totally different people. Well, I think the skill set is probably very similar. So, you know, as we talked about, I've always been interested in money and investing. At the academy, you know, when I was a student, undergraduate, I would help cadets balance checkbooks. We would always be with the select few that were interested in investing, talking about investments.

13:09Glenn Ullmann: My emphasis at the academy was in management, but every academy grad is an engineer when they get out, but, you know, took investment classes and tax classes. So when I left the military, I actually got a job working for a pharmaceutical company, Siba Geige in Boston. And I had never really had a real job in my life, right? I went from high school to the academy and then, you know, the academy, you know what you're going to be doing. So and then, you know, after after graduating, you know what you're going to be doing. But I knew I didn't want to do pharmaceutical sales after about a month because it was it was as like a professional caterer.

13:50Glenn Ullmann: So I don't remember who said to me, probably some friend or family member said, you know, you love investments. You love talking about money. You should go be a stockbroker because that's what we were called back then. So my first job was in Jacksonville, Florida with Smith Barney. My wife at the time and I did not know where Jacksonville was. We had to look on the map. This was before a lot of people still. No, yeah. Yeah, it's true. It's like Jacksonville, North Carolina. No, Jacksonville, Florida. And I had an opportunity at Merrill too. And so we like Jacksonville. We like Ponte Vedra where we eventually settled.

14:26Glenn Ullmann: And, you know, I worked for Smith Barney for, I think, three, four years. Started to build a client base. Cold calling. I mean, I would pick up the phone. I would start the Ponte Vedra phone book at A, and I would just call and say, hey, it's Glenn Oldman and Smith Barney. I do financial planning and investment management. The wealth management term hadn't been coined yet. Let's meet for coffee. And I dialed 200 people a day, and I probably got 10 people to talk to me. And I knew how many people I need to call every week to get 10 appointments, and 10 appointments would turn into one client. so after yeah so after four years i wanted to go out on my own but it was the you know mid-90s the internet was in existence but i mean there was no wi-fi or i mean i remember plugging my computer into a landline and it would just show my dad how great my my my connection was and it would just go ding ding i mean he would do that for five minutes he's like i don't see anything yet um all i was doing in the 90s with my computer was playing roller coaster tycoon and minesweeper so i that's great there's stuff there's stuff going on in the 90s but it wasn't it wasn't super high tech compared to you know parachute lowering no driving planes no and google maps so yeah so um i was going to go independent but it was it was just too big a lift with two little kids at home So I had an opportunity to build an office for Robert W.

15:59Glenn Ullmann: Baird, a regional firm out of Milwaukee. They had only had two CEOs in their entire history when I joined. That would change about five years later. But, you know, built an office for them. And then in 2002, as we talked about earlier, I wanted to start my own registered investment advisor. I wanted to be a fiduciary. That was really important to me. I wanted to focus on planning. And, you know, I've been very lucky to be able to have had amazing professionals join me over the years. And several years ago, we recapitalized the firm side. I now have four other partners. So, you know, it's a great joint venture.

16:44Glenn Ullmann: I feel very lucky to be able to work with them. And they keep me around. I'm still here. Right. I'm sure you carry your own weight. I hope so. I'd love to get into the numbers. When you left the Air Force, what was your approximate net worth? It sounds like you were already investing quite heavily by that time. That's an answer I don't know, but I would suspect in the couple$100 ,000, you know, an Air Force second lieutenant, first lieutenant, they didn't make much money. We didn't make much money. And I just, you know, when I was captain, I made a little more money. And the Air Force didn't have a 401k then.

17:22Glenn Ullmann: They do now. DOD does now, but they didn't then. So probably a couple of hundred. But Daniel, I remember when I was getting out, sitting down and calculating based on where I was then. So I was 29 when I was getting out. And if I put away X amount of dollars every year, what I would be worth, how long it would take me to get to my first million. And all I can say is they had never happened. I mean, for a variety of reasons, it never happened. I probably would have gotten over a million and then went down again. But I remember having this. It was just on a piece of paper. Not a bad goal setting, but yeah, I know.

18:11Glenn Ullmann: I'm long-winded. I would say a couple of hundred thousand, if that, when I left the military. And so after the military, pharmaceutical sales, then firm, firm, eventually an RIA of your own. Right. Walk me through some of the milestones in your own net worth and journey to where now you mentioned one and a half billion under management. What's your current net worth now and who's the individual that you're typically working with? Yeah. Well, the firm works with clients. I'd say our sweet spot is probably two to 20. We have clients below. We have clients above. We don't make a determination like a minimum.

18:49Glenn Ullmann: We want there to be a good fit. We want the client to perceive the value, and we're developing a trust relationship. That's the most important thing. And we have, obviously, clients above that level. And I think as we've added great professionals, the type of client, the sophistication of that client has also increased. We work with a lot more business owners, pilots, physicians, attorneys. One of our partners is a former family law attorney. He and another one of my partners, Caitlin Frederick, run our divorce advisory group. So we have never had a year. I don't believe we've ever had a year where the business contracted.

19:34Glenn Ullmann: So even if - That's awesome. So for how many years? 25 years now? Yeah, even 07 to 09 where account values, if you were just invested in the S &P, went down 40 or 50%. We're obviously diversified. Clients have fixed income. But we've always, in times of market trouble, we have always added new clients because people need... You know, the quote that I love, one of Maya Angelou's many famous quotes is, people may forget what you did, people may forget what you said, but people will never forget how you made them feel. And I think to point to this firm and the people, there is an actual love of the people, the clients we get to work with.

20:26Glenn Ullmann: And that trusting relationship is most valuable. Yes, firm is financially very profitable. We all make a good living. We pay our team well. But if people didn't trust us, I wouldn't still be working. I'll tell you that. And what do you pay yourself? And what's your all assets in your personal net worth today? Let's just say you and I had a side conversation. So I'd rather not say because it seems to me like a form of conceit. But my net worth has grown over the years. The way our partnership works is we pay all the partners a set amount, and then you get distributions based on your stock ownership of the firm.

21:08And you own what percent of the firm?

21:10Glenn Ullmann: I own around 20 % now. And that's because of some different partnerships over the years, right? Well, when we recapitalized, it was very important because I, at that point, owned 100 % of the firm. And that wasn't sustainable and it really wasn't right because Brian James, Kerry King, Pat Kilbane, and later Caitlin, and we're about to add another equity partner. They helped build it. Pat's been with me 12 years, Brian 10, Kerry 8. So how could they not have equity to improve their net worth? It just didn't make any sense. and it would have been almost impossible to keep great talent. So that was when we recapitalized and I'm getting older and I have younger shareholders.

21:58Glenn Ullmann: So, you know, there'll be a process of selling shares to them so that they can enjoy the wealth that I've been able to create for myself. I talk about money, business, and all the different happenings behind the curtain with people in the Hampton community all the time. If those are the types of conversations that you also want to have with people, people like you, your peers, people who are maybe a few steps ahead of you even in their business journey, check out joinhampton.com. When I think of what you do in terms of RIA, correct me if I'm wrong, but it's almost as though you're running a business whose product is telling, this is the wrong word, but anxious rich people that it's okay to spend their money.

22:37Is that an accurate description of what it is that you do? Yes. So tell me what, pretend I'm stupid. What is RIA? And how do you explain the philosophy of spending wealth attribution, actually building generational wealth to someone who's maybe the anxious spender? Maybe they're already wealthy and they need help spending because they don't spend. Maybe they're not. Maybe they're on the bottom of that spectrum that you provided and they want to be closer to the top. Yeah.

23:13Glenn Ullmann: So, so much of what me and my partners do is spend a lot of time on what we call a life map. So a life map, the way we do it is a 11 by 17 graphical illustration of what's important to the couple or the individual. So, you know, we start kind of like where you started. You're like, well, tell me about, you know, how you went from where you grew up to the academy or tell me how you, you know, how you how the business has progressed. I mean, it's the same thing for people. It's like, where did you grow up? What did your parents do? I like to ask, what is your greatest accomplishment? But I also like to ask, what's the biggest obstacle you've ever had to get over?

23:59Glenn Ullmann: So, you know, you talk about getting to know somebody. She's now deceased, but we had a client who was a buyer for a retail company and lived in New York and was coming back from Asia. I had never heard this story, but we kept asking, you know, biggest obstacle. She had been attacked in her apartment in New York. She had surprised a burglar who basically stabbed her and left her for dead. And she survived that attack. But does that affect your outlook on money and spending, security, and life? And so we ask about those values, their values as they relate to money. Obviously, we asked about their goals, but also who their professional relationship, who is their CPA?

24:48Glenn Ullmann: Have we ever heard of them? Are they top tier? Banker, state planning attorney. We always ask, what do you like to do when you're not sitting here talking to us? It could be, I go to church. I go to mass every morning. You know, we will talk about assets, liabilities, insurance. So, you know, and obviously then family and not just family as in humans, but family as in pets. You know, we know all the pets, how old they are. So, you know, you take that and then we use that to create planning, even in our second opinion services. You know, we offer that free of charge, as do a lot of firms. You know, that's not groundbreaking, but we'll build a full life map.

25:31Glenn Ullmann: We'll do all the planning. And so to answer your questions, I think it's bifurcated. We have lots of Henry's, high income, not rich yet. So these are professionals who are able to put away$10 ,000 a month,$5 ,000 a month. So they are not high net worth yet, but 20 years from now, they will be. So that's on one side. So this is all about a client like that needs to also enjoy their lives, right? So yes, max out your 401ks. Let's put X amount of dollars into your investment account. And we can show them what that looks like. But let's say there's another$10 ,000 a month sitting around. That's not saved.

26:21Glenn Ullmann: Well, we encourage clients in the accumulation phase to go enjoy that money. because when you have kids, then you got the education fund and kids are expensive. But it's so important because things happen. I've been around as long as I have been in this business. Things happen. People get cancer. People die in freak accidents, going hiking and falling off a ledge. So it's important that somebody, a couple that's working that hard also enjoys themselves. So that's on people who are growing wealth. I think for people that have had a liquidation event, inherited money recently, I think the most important thing is realizing that you need to help your community.

27:03Glenn Ullmann: And we talk a lot about philanthropy. Obviously, there's a great tax reason for philanthropy, but there's a moral imperative to philanthropy. But at some point, and we do this through planning, you build confidence through planning. If we have a plan and the client can spend$35 ,000 a month, plus their mortgage, plus their federal income taxes and the graph of their projected liquid net worth is going straight like that. I don't know which way on the TV screen works, but is going up. You know, we can show them, OK, well, this is if you took one hundred thousand dollars worth of vacations in a year.

27:41Glenn Ullmann: So if it's still going up to the right, but maybe not like this, maybe like that, that gives people the confidence that they can spend that money. All right, Money Wise listeners, quick reality check. It's that time of year when you catch yourself thinking, why didn't I start earlier? We knew summer was coming. It always does. And if you keep doing what you usually do, you'll blink and it'll be New Year's again. Same story, same body, same excuses. That's why today's sponsor is Daily Body Coach. Daily Body Coach is a premium online coaching service for ambitious entrepreneurs and executives who want their body to perform at the same level as their business.

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28:45Glenn Ullmann: Yes, you'll look better this summer. Leaner, stronger, sharper. But the real win is that you'll stop carrying a body that's taxing your energy, confidence, and longevity. If you're serious about fat loss, muscle gain, and building a body that supports your standards, don't think about it. Don't bookmark it. Don't push it to Monday. Click the link in the description, and I'll hook you up with Anthony directly. Check out dailybodycoach.com forward slash moneywise. That's dailybodycoach.com forward slash moneywise. Same thing in philanthropy. And as people get older, you know, I'm in my, I'll say early 60s, 63.

29:25Glenn Ullmann: You don't look it. Thank you. I dress up well for podcasts. So, you know, at some point the conversation is, listen, if you don't spend this money and fly first class, your kids will when you're dead. We have clients who have health issues in their 60s and 70s. And we say, you know, you want to go to, you have to go to Little Rock. Well, from Jacksonville, you can't go to Little Rock direct. You have to go through Atlanta or you have to go through Charlotte. So let's fly you private. We have relationships with air charter services that can fly a client from A to B. We're not in that business, but we can connect and help work out the details.

30:11Oh, I can't afford to do that.

30:12Glenn Ullmann: He's like, you can't afford to do it. Is it improving the quality of your life? Because if your kids inherit 10 million each, trust me, you know, they're going to either have a wheels up account or they're going to have a fractional ownership. Again, that's at the higher end. Some people, based on their history, you know, my dad and grandfather's business didn't go out of business. I do remember it struggling. But there are other clients who have grown up in tremendous need with single parents, raising them, assistance from both churches and the government. And their greatest fear is running out of money.

30:54Glenn Ullmann: So sometimes those people need, you know, five or six years or 10 years worth of reserves that are just sitting. Yeah. You know, and that's fine. And when you think of your story, were you that anxious spender as well that you can resonate with some of these individuals? Or, I mean, when did you, what was your net worth when you stopped worrying about spending? Yeah, I mean, I would say probably above 20, I stopped worrying about it. And so in terms of a range now, I would expect you're probably somewhere in the 25 to 40 million net worth range. Yeah. And so you don't worry about money anymore.

31:33You don't worry about your spending. No. Do you find that your own journey is typical with your clients or that a lot of them come with their own baggage that you have to sift through?

31:43Glenn Ullmann: I think it's as unique as we are all as human beings. I mean, I've always been, I would say I've always been a spender. And the times in my life where I have gotten, you know, we call it in the military and flying behind the power curve. Behind the power curve is when you can increase the power, but you're probably still going to hit the ground because you're behind the power curve. You don't have enough ground below you for the engine to spool up enough to get you away from the ground. And although I've always been a saver, I would say my inability sometimes to say no to expenses has gotten me in trouble.

32:26What does that look like month to month? You're a spender. What's a typical monthly burn for you and where does that money go?

32:32Glenn Ullmann: A good amount of it goes to a prior marriage for a couple more years. But a lot of it just goes to Daniel. I don't know. I mean, I don't. I used to keep track of the wealth manager. I know. That's a horrible thing. The company owner doesn't know where his money's going. Okay. You need someone from your own firm to help you know where your money's going. Okay. So here's the thing. The firm manages all of my liquid network. I don't touch it. I don't look at it. We have a great system. So that's the first thing. I do know where all the money's going because I still have a checkbook ledger. And I write - Like manual with a pen checkbook?

33:09Glenn Ullmann: Yeah, with a pen. And so - Oh, man. I just came back from Colorado hiking and, you know, I go to a restaurant. Let's say it's$170. We all go to dinner, a whole bunch of us. And I will put in the checkbook ledger, instead of the check number, I just put Amex, A-X, and then the date, where it was, and the amount. so that when my Amex bill comes in, I just check them all off. It's already out of my cash flow. I mean, I don't have to think, oh, where am I going to get that$17 ,000 for my Amex bill? It's already written out of the checkbook. So it is poorly worded that I don't know where the money is going.

33:50Glenn Ullmann: I know exactly where it's going. But if I had to say, where does it go? I would say mostly fun, travel. than having an airplane. So you fly yourself in there. How many seats does your plane have? Or, and you can put an infant in it, but pretty much four. So we can get from - Operating expense on that, let's say annually. What does that come out to? It's gotta be, including flying and gas. It's probably 40 a year. Oh, that's less than I would expect. Well, the airplane's brand new, so it's under warranty. So yeah, 40, maybe 50. Okay. And the plane itself was how much? I think it was 125. $1 ,250 ,000.

34:32Glenn Ullmann: $1.2 million. Okay. So you fly, you have fun. Yeah. Your fun expense, what does that come out to? $20 ,000,$50 ,000,$100 ,000 a month? No, not that much. So probably prior marriage, that's probably a third in alimony. And then probably fun is another third. And then we've got five kids between us. And so I've got one in New Zealand, one in Berkeley is about to get married, and one in Boston. And I try to see them on a periodic basis. Okay. And you have a home in Jacksonville. You have a home in North Carolina. Yeah. Are there any other homes? No, that's enough. I try to throw people once or twice during every episode.

35:12Yeah. But so all in your annual burn, let's say 150 ,000 with the plane all in.

35:20Glenn Ullmann: I'd say not including philanthropy, I'd say 500, 30 to 40 a month to run our lives. 40 a month. And then so that's not including philanthropy. And you mentioned a couple of times so far, a lot of the even philosophy and morale of your business model is philanthropic. And so walk me through what your personal giving looks like and why that's so important to the way that you run your business. How do you make sure the charity is going to spend your money correctly? Yes, it's a huge tax benefit, but every year I exceed the amount I can deduct because especially in up markets, to give appreciated stock and never pay capital gains and put it into a charity fund is incredibly powerful.

36:06Glenn Ullmann: So if I meet somebody or I'm introduced to somebody, like we were talking about, I think we were talking about this earlier. No, maybe we weren't talking about it earlier. I have a lot of conversations during the day. I can't remember who I'm talking to. Maybe people shouldn't know that. But you don't have to be messing up your cash flow, your monthly cash flow, because you have a philanthropy fund. I'm curious. You mentioned, you joked earlier about, you know, they still have me coming in. Why are you still going in? It sounds like you're well past the threshold number of, you know, needing more.

36:40You're giving, you're spending, you're having fun, you're traveling. It sounds like you had two liquidity events, if I'm not mistaken. or I guess recapitalization rather. What's driving you to continue now and not just kind of retiring or whatever that would look like?

36:57Glenn Ullmann: I don't have a lot of other interests as I'm sometimes reminded. But the real reason is I still love what I'm doing. To be able to work with my partners and other team members, I mean, it's just fun. Our advisory firm, I'm the oldest at 63. Our youngest planner is 26. Our youngest partner is 36. We've got partners in their 40s. I just feel like it's an opportunity to teach and to mentor. And I love the clients. I mean, that's the thing. And there are a lot of clients now that I don't know. You know you have what's called an ensemble practice when you don't know a lot of the clients. Like we call every client on their birthday.

37:40Glenn Ullmann: No cards. Call. That's cool. And so they come up on the list and I don't know who they are. Well, that's great. That means the rest of the team has their own prime relationships. Every client in our firm has two advisors so that if one is unavailable, one gets hit by a bus, the other advisor, the wingman or wingwoman, knows everything about the client. The life map is another way that we make sure that not only does the wingman or wingwoman know the client, but the whole team can pick up a life map and pretty quickly get a sense of the client. We talk about this in terms of succession. I mean, we don't have to really worry about succession because we have partners at all ages.

38:20Glenn Ullmann: I mean, as long as I'm healthy and enjoying what I'm doing, I'll easily be around till 70. But I think it's also important to get out of the way. I mean, the firm does have my name on it for now anyway, Oman Wealth Partners. But I have a strong personality and my other partners do too. And sometimes it's important for a founder to get out of the way. And because if I'm around, you know, sometimes I think that deference to my opinion may or may not carry the day. So I know it's a long answer and I struggle with it. I really do. I have a series of three chronic illnesses, which I'm not going to discuss, although our clients know.

39:05Glenn Ullmann: But I love being involved. That's it. Yeah, I can tell. Yeah. It's a passion of yours. It is. It's no secret. Talking to you, I can feel that for sure. I've been able to do the two things that I have loved doing. I mean, flying airplanes was a passion of mine from before I'd ever been in an airplane. And money and wealth management and making people, I mean, our tagline is our discipline, your freedom. Giving people that freedom, that freedom not only from worry, even people who come to us and are not in good shape. I mean, I can't tell you how many times this team has helped people get back on track, has helped people pay off student debt, has helped them set up a payment plan with the IRS.

39:54Glenn Ullmann: They didn't even know they could call the IRS and say, hey, can I set up a payment plan? Encourage people to advocate for themselves where they were being underpaid in a market. Go get a different job. So it's not just that we manage a lot of wealth. We do, but giving people that confidence that if you do this, this, and this is going to work out. I know you got another question, but I have to tell you, it's my Melissa example. So Melissa has been a client of mine since 93. She's one of my first clients. She's been in the IT tech business, never out with Google or anything. But when I started with her, she was putting$100 a month into a mutual fund.

40:37Glenn Ullmann: Then it went to$500 a month. Then she got a 401k. She maxed that out. Melissa takes the best trips on earth. The amount of places that she's gone is incredible. And she has created this wealth by doing it systematic, literally doing it systematically. And it's my Melissa example. That is so gratifying. You know, she's now in her mid to later 50s. There's nothing greater than getting somebody on track, getting them back on track. That's amazing. Yeah, I get to do the two things and I get to go fly my airplane. Yeah. How lucky am I? When you say you like having fun, it's like, oh, no, no, that's like actual fun, like flying your own plane to and from.

41:15Glenn Ullmann: But how lucky, seriously, how lucky am I? I mean, I was adopted at three months. So, you know, my life could have, I don't know what my other life would have been like, but I'm the chosen one of the four kids because I was adopted. The rest of those were born to my biological parents, my adoptive parents. So, I don't know. It must have been a cockroach in a prior life or something. So anyway, I feel very grateful. I feel that from you. I'm curious, because half of our listeners, I would say, are ultra high net worth individuals themselves. The other half, they're aspiring. They're company owners.

41:52They might be doing$3 to$10 million a year. So they're successful, but they haven't made it yet in their own words. They're still shooting for the stars. What would you tell someone who's just recently had a liquidity event? Let's say they made$10 million of liquid. Where should they park that money? There's a lot of opinions on this, and I'm sure you have heard all of them. But where does someone put that money so that 5, 10, 20 years from now, it's still growing and they're not broke?

42:20Glenn Ullmann: Well, I'm biased. I would say figure out how much you're going to spend. Figure out how much is going to go into another business because a lot of entrepreneurs are serial entrepreneurs, so they're going to need liquidity. But, I mean, in a balanced equity fixed income portfolio, put some private equity in there, private credit, private debt, not a lot. But you can't help but be financially secure. And I think that one thing that people forget is that if you have$10 million, you're all worried about it turning into$5 million, right? Or$2 million. But a well-diversified, and I'm talking using low-cost mutual funds, you can use a personal, you can create a personal index, exchange-traded funds.

43:06Glenn Ullmann: It doesn't have to be complex, right? What people forget on$10 million is you're probably going to collect around$300 ,000 a year in dividends and interest. Whether markets are up or markets are down, that's the rent you're getting on your portfolio. That$20 million,$600 ,000 a year. So make sure that money that you're going to need is in fixed income. It can be in CDs, something that you can use for other investment vehicles. I'm not a big real estate guy. I own the building here. And we have the two houses that Lisa and I have together. I know people love real estate. To me, every real estate, real property I've ever had has made me money.

43:47Glenn Ullmann: But there's a tremendous cost of carrying it. You know, here, I mean, we just replaced the entire driveway here. It was a hundred grand. I have to replace my driveway too. Good grief. We have the same issues. I literally have to fix the irrigation so I can replace my driveway. Oh, that's painful. Because it's right next to the concrete. I got to move the whole thing. It's so painful. Yeah. So, I mean, real estate, we had a celebrity client years ago and she said, I never invest in things that eat while I'm asleep. I thought that was a great one. But look, you could also make the same argument if you know real estate really well that buying a class A property that's going to allow you A, to depreciate a big amount, that's huge on the tax savings side.

44:35Glenn Ullmann: We see that actually with the airplane. But you're going to get rental income. So no asset class, in my opinion, is bad. Some people are more comfortable in real estate. Some people are more comfortable in stocks. But stocks to me, I don't use that term other than I just used it. I don't like to use it because I think it creates that visual image in many people's minds of the stock market crash and food lines in black and white. They're not stocks. They're companies. You invest in the S &P 500, you're buying a piece of the 500 greatest companies in the United States. Why wouldn't you want to do that?

45:18Is that where most of your money is parked in index? Yeah. Yeah. Like 60%, 80 %?

45:24Glenn Ullmann: Well, if you take the real estate out, I'd say 90 % is in global equity with a little bit in private equity. And, you know, obviously this firm is private equity, but outside this private equity, a little bit in private equity, a little bit in private debt, a little bit in private real estate. But, yeah. That's great. And it should be. Yeah. I mean, I think that's typically my opinion as well. I do a tiny bit of stock picking, but it's typically with one of the 500 companies on the S &P 500. And there's a few that come to mind. I won't mention them, but I think from a lot of the people I've spoken to, whether it's 25%, 60%, like you said, 90%, S &P 500 is hard to not invest in if you have money that you want, I would say, safely.

46:13Maybe it's not the right word, but conservatively invest over time.

46:17Glenn Ullmann: But again, it's always the income side that we forget. And the income is so powerful. People who we can have the conversation about, let's say, flying private because there are health concerns or just time. They want to go from point A to point B. They want to go from point A to point B to a little town in western Colorado. And they don't want to take all day. They want it to take three and a half hours. Most of the time, if we say to them, it's going to be$80 ,000, but then say, oh, by the way, you're getting$30 ,000 a month in dividends and interest, which you're not spending. They're like, oh, it's a month and a half of income.

47:01Glenn Ullmann: Yeah, it's a great way to look at it. It's just changing that frame. That's great. Glenn, this has been an incredible episode. I really appreciate it. I think your insights, your insights are unique. And I think given that you yourself are a high net worth individual, but also advising, you know, and helping to manage the wealth of, it sounds like, you know, one and a half billion under management. That's incredible. I also love that you're a pilot. I love your background. And that we have to fix our driveways. Yeah, that's right. We have the same house in different places. So I might call you for your contractor.

47:34Come on. But yeah, man, driveways are just one of those things. You know, 50 to 75 years ago, people just drove on dirt. It's like driveways and roads are a brand new invention in the grand scheme. Well, driveways are.

47:48Glenn Ullmann: Now, the Romans did have a pretty good road system, but I don't think they had driveways. You just tied up your horse. They sure didn't. I mentioned I went to Clemson. I actually studied history, and I remember learning about the first fences that were made in the United States and all the things that humans just decided, yeah, I'm going to put this up and decide that this part of this fence is mine and that far since it's yours. And anyways, Glenn, this has been awesome. I really appreciate your vulnerability and sharing some of your wisdom. It's been a great conversation. And I would say, you didn't ask me this question, but if somebody said to me, I want to do this, what career field should I go into?

48:23Glenn Ullmann: I actually think English or history. Yeah. Why? Well, English, because what I have found, especially with some in like maybe the under 30s, just not used to, you know, talking on the phone is, is hard for some in our, in some of. Talking to people in general nowadays. Yeah. Because everything's on email or text. I'm a big student of history. I mean, I, I love reading history. My son, Andrew's always sending me podcasts. Every time I hear a newscaster or read some article where somebody says, this is unprecedented. I'm like, no, it's not. I had a history teacher, a professor who said unprecedented every single lecture at least five times to the point where I would back channel and group text with students and just say unprecedented periodically every time.

49:21Yeah, everything in history is unprecedented until you read five more seconds of history and realize nothing really is unprecedented. Nothing's unprecedented.

49:30Glenn Ullmann: It's, you know, as Mark Twain is alleged to have said, history doesn't repeat itself, but it sure does rhyme. I love that. Yeah. Glenn, I hope we can stay in touch. I mean, you're an awesome person. This is very cool. Again, I appreciate you coming on the show and look forward to hearing the finished quality episode. Awesome. Thanks, Daniel. Take care. Bye.

From the publisher

We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wr

Why do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.

He manages $1.5 billion for other people — and still tracks his own spending in a paper checkbook.

Glenn Ullmann is a former Air Force pilot who left the military at 29 with a couple hundred thousand dollars, cold-called 200 strangers a day out of a Ponte Vedra phone book, and built Ullmann Wealth Partners into a $1.5 billion RIA that has never had a down year — including 2008. He stopped worrying about money somewhere north of $20 million. Now 63, he spends $30–40K a month, flies his own $1.25M Cirrus, gives more to charity than he can deduct, and still shows up to the office every day.

This episode gets into the tension between saving and actually living: why Glenn tells clients with health issues to fly private before their kids do it with the inheritance, how a $10M portfolio pays you $300K a year in "rent" whether markets are up or down, and why he thinks stocks are a bad word. We also cover how he gave up 80% of his own firm to keep his partners, the paper ledger that runs his life, the client who started at $100 a month and now takes the best trips on earth, and why he'd tell a 20-year-old to study English or history instead of finance.

Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mw

Timestamps:
01:46 — Who Glenn is, what Ullmann Wealth Partners does, and why "returns don't matter if you rear-end Melinda Gates without an umbrella policy"
04:16 — Growing up in his grandfather's plastics business, the Robin's-egg Cadillac, and the gold coin that says "your friendship means more to me than a pot of gold"
06:26 — A Morgan Stanley account at 14, paper route money, and his first stock: Sears Roebuck
07:44 — Nobody from his high school went to the military. He went to the Air Force Academy three days after graduation: "the best thing I ever did, other than marrying my spouse"
11:50 — The Cirrus G7, the parachute that lowers the whole plane, and the button his wife can push if Glenn stops functioning mid-flight
13:35 — From AWACS pilot to pharma rep to stockbroker: dialing 200 people a day, 10 conversations, one client
17:45 — Net worth leaving the Air Force at 29 and the million-dollar goal on a piece of paper that "never happened"
19:26 — The $2M–$20M client sweet spot, and why the firm has never contracted in 25 years — even 2007–2009
21:57 — Why he went from owning 100% of the firm to 20%: "How could they not have equity?"
24:03 — The 11x17 "life map," and the client who was stabbed and left for dead in her New York apartment
26:15 — HENRYs who save $10K a month and still need to be told to go enjoy the rest: "People get cancer. People die falling off a ledge."
28:49 — "If you don't spend this money and fly first class, your kids will when you're dead"
30:40 — The net worth where Glenn stopped worrying: "probably above 20"
31:49 — Alimony, fun, and the pen-and-paper checkbook ledger a $1.5B wealth manager uses to track his Amex
33:29 — The $1.25M four-seat plane, $40–50K a year to operate, and a $30–40K monthly burn before philanthropy
35:10 — Giving appreciated stock and exceeding his deduction limit every year
36:21 — Why he still goes to work at 63, the wingman system, three chronic illnesses, and "sometimes a founder needs to get out of the way"
39:40 — The Melissa example: $100 a month in 1993 to the best trips on earth
41:26 — Where to park $10M after a liquidity event: "you're going to collect around $300,000 a year in dividends and interest"
42:55 — Not a real estate guy, the $100K driveway, and "I never invest in things that eat while I'm asleep"
44:48 — 90% in global equity, and why "they're not stocks, they're companies"
45:40 — Reframing an $80K private flight as a month and a half of portfolio income
47:39 — What he'd tell a 20-year-old picking a major: English or history

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