How Humphrey Yang Built His Wealth

Humphrey Yang’s Background (0:00)

Brian: How Humphrey Yang built his wealth.

Bo: Brian, I am so excited about this because we have a special guest in studio today that has literally impacted the financial lives of tens of millions of Americans. I am so excited that we have Humphrey hanging out with us today. Welcome to the studio, Humphrey.

Humphrey: All right, you guys are really excited for a Tuesday morning at 10 in the morning Central time, 8 a.m. Pacific. You know, every single Tuesday we are all loaded up with some caffeine.

Brian: We have a special guest here and with an intro like that, this has got to be like what are these guys doing, right?

Humphrey: I know, right?

Brian: But in all seriousness, look, we talk about a lot of our content. I know I’ve shared many times that Bo comes from very humble beginnings. I shared all my mistakes and all the things that have made me who I am in Millionaire Mission. So, you know, there is something about where you come from, what you’re raised in, who your parents are, that stuff shaped you all through your childhood. And I mean, what I want to know is when Baby Humphrey came to the world, give us a little background. What was it like being Baby Humphrey?

Humphrey: Yeah. Baby Humphrey was really addicted to video games. I loved video games and you know I grew up in a pretty good, I would say the house was pretty nice for where my dad was in his career. I think he spent a lot of money on his house.

Brian: Got it. And what did your parents do for a living?

Humphrey: My dad was a fighter pilot.

Bo: Oh, cool.

Humphrey: Yeah, he was a fighter pilot in Taiwan. And then he came to America on a CIA contract.

Brian: Even cooler.

Humphrey: That was to fly unmarked planes in Vietnam. So he flew in the Vietnam War for the United States. That’s how he got his citizenship. And he kind of flew an unmarked plane. He said 75% of those people that flew those planes died. So he was one of the remaining few.

Brian: No shadow on you.

Humphrey: Yeah. And then so after he immigrated to the United States, he started working in commercial. So he would fly these cargo planes to Tahoe and Reno from San Francisco and then he flew commercially for airlines and stuff like that. But he mostly was a successful businessman as he would do airplane leasing. So what that means was he would be a broker between an airline and the people that made the parts. So an engine contract could pay him like a pretty good commission because I think back in the day airlines used to lease engines from these manufacturers at for 30 years or whatever and they would advertise them against their balance sheets. So that’s how he made his money. He would sign these bigger deals, especially with the Asian airlines because he was Chinese. He worked with a couple American business guys and he would be the Chinese contact in the 70s and 80s.

Brian: Okay, that’s awesome. Great. How about your mom?

Humphrey: My mom did not work. My mom has a middle school education. My dad found her in China when she was like 32 and then they got married in six months. So it was pretty quick.

Brian: That’s awesome.

Humphrey: Yeah. So he built his wealth that way. But when I was growing up, money was always a big topic in our household. He grew up very poor. He had nothing to eat. From ages like 8 to 13, he was struggling. And both his parents went to jail. One went to jail. His dad went to jail. And my grandmother passed away early. So he grew up really poor with nothing in Shanghai and then there was a Japanese occupation at that time and that’s why he fled to Taiwan. Now with that in mind that gave him a scarcity mindset around money, right? He hoarded everything that he could. And that was kind of passed down to me. I think growing up he would always say if you don’t have to spend money don’t spend money. Like if you absolutely need something then you spend money but only if it’s an absolute necessity. No wants spending, but he would kind of categorize some wants in a different bucket like if you need a nice desk chair because it’s going to help your body you need that obviously. And so that would sometimes make me rationalize to spend like an $800 desk chair when I didn’t really need it. I don’t need this new video game because I’ve beat the old one, right? That’s the kind of thought process. But that was why I think money was always a topic for us. I think I was like four or five and I would ask my dad are we well off, are we doing good and you know he wouldn’t really give me an answer and he didn’t really give me that much money as a kid. He gave me a little bit of an allowance like five bucks here and there but that’s all I really remember about my childhood is money was always a topic.

Impact of Parental Money Mindset (4:52)

Brian: What shaped you though? I mean, is that the thing that seeing parents that modeled being tight with money, did that create some weird uncomfortable or bad dynamics with money though? Because there is something, it’s one thing to grow up where you know if your parents tell you you’re poor but you know there’s money coming in that might have its own after effects too. I mean so did that do you have some ripple effects from that?

Humphrey: I don’t think we were told we were poor, but it definitely made me scared to invest because he was kind of more of a risk averse person with his money. So, it was a lot of cash. A lot of cash. He bought his house in cash. And so, he was always afraid of going into debt. He never wanted to be in debt. He saw how debt and leverage kind of ruined a lot of his friends. And so, for him, it was always like if he had the money, he would buy it. And then also he kind of instilled these values in me of let’s be more risk-averse or save your money. If I had $10,000 at age 25 he’d be like oh yeah you should save 60% of that and maybe you can invest 20% of that. And now I’ve kind of changed my mindset around that to flip it around almost.

Bo: I was going to ask what changed because obviously now you are a personal finance expert. You’re literally sharing how to make sound financial decisions with tons of people. What changed? How?

Humphrey: Data. Data changed. Yeah.

Bo: So, you just learned—what was your background getting into even the financial space?

Humphrey: Yeah. So, I studied finance in college at Loyola Marymount University. I didn’t really learn that much about finances in college, but that was around 2008. So, I do remember that quite well.

Brian: It’s a great time to learn some stuff.

Humphrey: Great time to learn some stuff. And I wasn’t really an investor until I became a financial adviser at the Merrill Lynch program. So, Merrill Lynch, they had a program to learn to become a financial adviser. I studied for the Series 7 and 66, passed those and I really learned more about money, the data behind the S&P 500, the market, how you should be really investing your money to make it grow, to go against inflation and the printing of more currency.

Brian: Well, I have a question just because this just came to me. When you’re a Merrill Lynch adviser, you do a lot of proprietary funds. At what point did you like maybe I ought to be buying an index fund? I mean where does that fit in? I’m just curiosity-wise because you now you have the hindsight. I mean is that something that pops up?

Humphrey: Of course so I was not an adviser for very long. I’d say about a year and a half. And the reason is because I realized that the industry at least the Merrill Lynch program was more about prospecting and getting people to bring their assets over to you. And then once their assets were over to your firm, Bank of America, Merrill Lynch, and I assume Morgan Stanley would probably work this way too or some of the other bigger firms, they kind of put you in these set products and really the investments they take care of themselves and really the clients are there to have somebody to talk to on a quarter-to-quarter basis, right? They’re really interested in let’s keep the relationship happy. Let’s maintain their expectations, make sure that they’re at least matching market returns, maybe less a little bit of the management fee, but really it wasn’t about taking huge risks in my opinion. I think it was more about the guidance that a financial adviser could give you. So once I really learned about how an index fund, a Vanguard S&P 500 index fund could just do as well as a financial adviser, I just didn’t really believe in the space anymore as much. But I’m not saying that they’re not useful. They’re still useful.

Brian: Well, look, we actually, most people, I would agree that’s because I’ve seen you’ve covered Ramit and others. I would tell people if all your financial advisor does is the investment side, that’s already been commoditized through index investing anyway. That’s why I was just, I had a friend who lives in Chicago. He works with one of these institutional advisory firms. It’s even on one of the lower cost sides. And he was like, and I was like, “But if they’re not talking to you about your property and casualty insurance, Roth conversions, are they reviewing your tax return every year to see if you’re leaving money on the table or making sure everything got implemented right?” I was like, “This is what a financial planner does. It’s not if you’re just doing asset allocation and telling you, hey, do this Fund of America or this index fund here, that’s commoditized already. So, you’re never going to insult me by saying you don’t think a financial advisor earns their keep because if all they do is investment stuff.”

Humphrey: So, I do think they earn their keep with all the things that you just mentioned, right? And I also have a friend. He makes, he’s on YouTube. I’m not going to name him, but he is also from an immigrant background. And he makes $20,000 to $50,000 bucks a month. But he was all cash for a long time. And he kept asking me, should I invest? Should I invest? Should I invest? This was like last year, 2024 before Trump took office and he was like, “Should I invest?” And I was like, “Yeah, you should invest.” He never did. And so what he did this year was he actually hired a financial adviser just so that he had more confidence to invest, right? And so he hired this great firm out of San Francisco and you know he’s paying like a 1% management fee, but the alternative is not investing.

Bo: But think about how much better off he is even with that 1%. I mean, obviously the value that he’s receiving far exceeds the fee that he’s paying, and that’s the trade-off that you ultimately want, right?

Humphrey: And so for him, I told him you could just go with an index fund, but if he’s too risk-averse to do it, he might need that extra help and he also gets the other services now, too, right? So, he actually kind of likes it now. But that was something for him that he had to realize, you know, he wasn’t able to do it himself, just the investing portion. So, he trusted someone like you, Abound Wealth Management.

Advice to Young Humphrey (10:52)

Bo: I love it. So, if you could go back in time and talk because you said you had to gather data to be able to inform yourself, if you could go back in time and talk to 20-year-old Humphrey, or that just brand new starting out, or if you could say something to folks that are just starting out, you just celebrated a birthday. Is there some information or something that you would tell them that would accelerate all those years of data gathering it took you for it to click that you would say now oh man if I could just tell 20-year-old Humphrey this I would let him know, Humphrey do this?

Humphrey: I would have invested way sooner and I would have not touched it at all. What happened was when I was like 24, 25 and wanted to get into this financial advisory business, that’s when I started investing and there were these dips and periods of times where I had some Apple stock and I sold a portion because I got a little nervous or I sold a portion of Tesla stock. It came out in 2012 and it was like $10 bucks a share or less and I bought some and I sold some. I was like, “Oh man, if I just never touched it, I just kept dollar cost averaging and just buying, my portfolio would probably be like three times as big today.” But I was just, you know, I got scared.

Bo: So, you’re saying don’t let your emotions drive your financial decision-making when it comes to being an investor, when it comes to putting money to work. Go into it and try to remain as unemotional as possible and maybe even employ strategies that allow you to be unemotional, maybe index funds instead of individual stocks that you feel like could cause you to move in that direction.

Brian: Well, and that’s what I was going to add is that because I think that this could be an emotional freeing event for a lot of people because you’re a trusted voice out there, tens of millions of Americans. Let yourself off the hook. If you’re one of these people that bought maybe because the hot topic right now is Nvidia, and there’s a lot of people doing exactly what you said. They bought Nvidia, but then after it went up four-fold, they sold a portion of it. That’s the problem with all these things is that if you get it right after it doubles or triples, you’re likely going to sell it because it feels like, hey, I’ve made all this money. I ought to sell it. And then you go kick yourself when it goes up 10, 20-fold. Well, it’s the same way. And if you bought it and then it goes to complete crud, you kick yourself that way. It’s a no-win situation. All of your happiness and other things are driven by this individual holding. That’s one of the reasons I love index investing is because it takes out the emotional side and it lets you actually focus on your time and what’s important to you versus getting so caught up in your happiness being tied to this one company or this one pick.

Humphrey: Yep. It does take a lot of discipline though and I’m sure everyone watching right now is really into money. So that’s, and that’s another problem is that you’re probably keeping track of the market right now as we speak because you’re so interested in money. And so it’s almost better to be almost ignorant sometimes. Ignorance is bliss sometimes with investing, right?

Bo: I love that. That’s why I do my net worth statement one time a year. One time a year because I like surprises. I like seeing what happened, right? But you said that one of the things that transformed was being able to gather data and let that inform your decision. Well, one of the things that we love to do every single Tuesday at 10 a.m. is we come right here so that we can load you guys up with data. So, we tell our audience we want to be here to help them do money better. And one of the ways we do that is by answering your questions and you guys are in for a treat right now because we have Humphrey here to answer questions with us. So, if you have a question that you would like for us to weigh in on or if there’s something you want to get our or maybe just Humphrey’s take on, make sure you get it in the chat right now. We have the team out in the wings collecting your questions. So, with that, creative director Rebie, I’m going to throw it over to you.

Humphrey: No hard questions, please.

ETF vs Mutual Funds (14:50)

Rebie: Okay. I do have a question up first from John. It says, “Super excited to see this collab.” So am I. We are too. It says, “What are your thoughts on ETF versus mutual funds and aggressive versus conservative investing? Would love to see what all three of you have to say about this.”

Bo: Okay, so first, how about a very quick vocabulary? When we say ETF, that just means an exchange-traded fund. It’s a basket of stocks, but rather than trading at one time throughout the day, it trades throughout the day, similar to a stock. So, it’s very similar to a mutual fund, but it’s more liquid and more able to be traded throughout the day. Mutual funds, same sort of thing. Basket of goods, could be stocks, could be bonds, could be other types of holdings, but rather than having to go out and buy all 500 companies in the S&P 500, you could buy a mutual fund, one holding that represents those. You could buy an ETF of the S&P 500, one holding that holds those. That’s kind of the vocabulary difference between the two. So Humphrey, what are your thoughts on mutual funds versus ETFs? And then even he tacked on aggressive versus conservative investing.

Humphrey: Yeah, I would also add that ETFs are typically passively managed, right? Versus a mutual fund usually has an active fund manager that is getting paid based on that performance. So sometimes your expense ratio or your fee that you pay per year for holding that fund is a little higher with a mutual fund, right? Typically in the range of 0.35% to 0.5% or whatever it is, sometimes even higher, right? There’s like those Cathie Wood ones, the ARK Invest ones. Those are like 0.75% to 0.85% expense ratio. So, you really have to think about how your fees impact your overall returns and how they’ll eat into your returns over a long period of time. But an ETF is usually passively managed and usually tracks a specific sector or index. And I typically prefer those. Aggressive versus conservative investing, I think it depends on your risk tolerance and your time horizon, right? So if I was 20, I’m probably aggressive because I have 45 years until retirement at, hopefully I retire earlier, but let’s say it’s 45 years and for a normal retirement, I can probably be more aggressive and even if I lose some money, it’s okay because I have so much time to make it up. So I would probably err on the side of aggressive as you’re younger and want to build that wealth and then more conservative as you kind of start to need that cash flow.

Bo: Love it. I think one of the other things that people don’t realize is that oftentimes people think okay mutual fund that means it’s going to be aggressive, ETF that means it’s going to be aggressive, but there are actually conservative versions of those holdings. There are bond mutual funds. There are bond ETFs. But a lot of people they say, “Okay, well, I heard what Humphrey said. I want to be aggressive while I’m young and I want to get more conservative, but I don’t know how to do that. Like, how do I make that adjustment?” And what’s great is there are some solutions that actually allow you to do that.

Brian: Yeah, this is, look, we think there’s a time and a season for being buck wild aggressive trying to get as much growth as you can. That’s the actual risk tolerance, especially in those Roth accounts. We want you, but it’s that balance of you don’t want to be so crazy that you risk it and it goes to zero, but you definitely want to maximize growth opportunities and while you’re young, that’s a great thing. But then as you get a little gray in your hair and you get a little older, it’s just like that. I love the title of glide path. I mean that’s what a lot of the mutual fund companies will talk about. What’s glide paths? If you think about we talk about index target retirement funds where you only have to think about how much you can save each month and when you need it and then they do the rest. It auto allocates. You can do the same thing yourself even with index investing. And it’s the same way I look at the way I handle my own money. People who are trying to be debt crusaders and pay off their low interest sub-4% mortgages before you’re 45 years of age, they think you’re cutting risk but I think that it’s actually cutting your chances of making sure you build wealth. But there’s a time or season is that be more aggressive while you’re under 45, but then when you get over 45 and hopefully have built up your assets and your army of dollars working for you, then you can pivot to taking the risk off by paying down debt aggressively. So, all this stuff is interconnected with how you look at being aggressive versus conservative. And then I’d like to say on the ETF versus mutual funds, a lot of times these things, it’s almost like synonyms of each other. If you’re doing index investing, I’m an index investor. My monthly investment that goes in weekly because I’m a nut is an index mutual fund because it’s just easy with the custodian that I have to set up an automatic builder. I know they’ve gotten where you can even do this with ETFs but the mutual fund is the cheapest version of the S&P 500 out there. It is very very cheap to buy this index mutual fund. But then sometimes when I’m doing tax planning and I need to do some loss harvesting or other things when we’re in those type of seasons, I will buy ETFs at the end of the year because it’s just a very tax-efficient way to use those tools. But you’re not hurting yourself if you buy an index mutual fund or you’re not hurting yourself if you buy an index ETF. You just need to know what they are and they aren’t. And then it’s okay if you have both in a lot of cases too.

Bo: Love it.

Rebie: Yeah. Good stuff. Thank you John for the question and for being here in the live stream today.

Cash in the Messy Middle (20:26)

Rebie: All right, this next one’s a good one. Let’s see if we can help Bianca. She says, “Hi, Money Guy team. I make around $70K to $75K gross. I invest 25%. But I feel like I’m missing out on life. I’ve never been on a plane anywhere and I was thinking of taking a second job to help do this.” Thoughts?

Brian: How old is—

Bo: I was going to ask that question.

Rebie: You know what, Bianca, if you’re out there, let us know.

Humphrey: I’d say by the lower caps that she’s probably Gen Z.

Rebie: This is not—Look at the perspective. I love it. I think that’s very possible. Bianca, let us know.

Bo: You know, do you see a lot, Humphrey? Do you come across this a lot in your audience where people are like, man, I’m so committed to the future. I’m so focused on thinking about the future that I have to save. I heard Humphrey say that if I just start investing early, then I’m going to set myself up for success. So much so that they kind of lose track of the present.

Humphrey: Oh, Bianca’s 26.

Bo: 26. 26 years of age.

Humphrey: Nailed it.

Bo: I don’t do that kind of math. Public math. Bold. You did that on the fly.

Humphrey: I do see that a lot. And you know, my audience typically oversaves, right? Because they’re watching the channel and I’m always like hey get your savings to 20%, 25%. In Bianca’s case I think she might be able to lower it to 20%, 15% and maybe enjoy life a little bit. Because what’s the point of money right if you’re always saving for the future? You’re going to be 65 and you maybe missed out on some experiences. So that’s what I would say to Bianca is if there is room to maybe invest 20%, you can still hit your retirement goals and maybe even more but still be able to enjoy a little bit of life.

Brian: I don’t know. We actually have a great deliverable that I would tell Bianca and if the team could pull it up, if you go to moneyguy.com/resources, What You Should Save. Because it’s funny if you’re 26 years old, if you look at the cross reference here for a 25-year-old who’s saving 15%, you pretty much have a replacement ratio close to 100%. If you’re doing 20%, 133%. 25%, 166%. Without a doubt Bianca if you tell me because look as soon as I hear you haven’t even been on an airplane, I resemble this so much because I didn’t get to do a lot of fancy vacations and other things as a kid growing up and I remember the first time I got to fly was my first job and I was going to do an audit and I went and bought a sports coat because I thought that’s what you did. You dressed up to go on an airplane because I didn’t know anything, coming up from humble beginnings. And it sounds like Bianca, you’re the same way. I don’t want you to wake up when you’re my age and go, “What the heck was I doing in my 20s? Why did I screw up and save?” Because I’ve seen so many, we were just at press publish or whatever and there was a guy, Casey Neistat, his whole thing was once he started making big money, he realized how empty it was. I know that if you’re broke right now, you’re like, “Shut up with this stuff. I hate it when rich people tell me it’s horrible to have all this money.” No, but I’m telling you, there is a balance there from yes, cover your basics. Do the responsible discipline thing. But there is a thing where you get so disciplined, you squander what life is meant to be if all you do is hoard it in the background. That’s why I say there’s a fine line between financial mutant and a financial miser because what Casey was saying is he got to the top of the mountain and realized oh my gosh it’s so empty here that I haven’t built enough life into this that he was running and screaming from the mountain tops go back, go back and go do more stuff. And I think that’s the thing I would tell you Bianca. I don’t want you to be in your 50s and go what was I doing? Yes I’m wealthy, I’m loaded but I’m not in my 20s anymore. I’m not going to be in my 30s and I’m going to miss out on a lot of life. So, enjoy every age and decade you’re in. Bedazzle your basic life so that you have just a life of no regret.

Bo: I also think that she’s doing really good. I mean, she’s crushing it. Investing 25%. That’s why we can also tell her it’s okay because I have so many people and I know you do in your audience too, Humphrey, that they’re hard on themselves. They need somebody to kind of coach them and say it’s okay. A lot of people, we were picking on financial advisors earlier. Another thing I think we as financial advisors do, a lot of people think we’re the Suze Ormans. I’m aging myself by saying that because her shows were no no no. It’s just the opposite. We are constantly telling people, “Go do this. Go do more. Go live your best life.” Because sometimes you financial mutants are the hardest on yourself. And you need somebody out there giving you perspective and context saying go enjoy your life. Money is nothing more than a tool that allows us to accomplish the goals that we have. But I think so often we forget not all goals have to be 40 years down the road. Not all goals have to be 20 years down the road. It’s okay if one of your goals, Bianca, is to fly in an airplane and go on a trip somewhere if you use the money that you have right now to help you accomplish that. And so one of the things I tell all people to do is, hey, list what all your goals are, both long-term, intermediate term, and then short-term. Prioritize how important they are, and then make sure your dollars align with that priority. Because if just having a big stack of money at the end of your life is your only goal, then yeah, throw everything at that. But if you have other goals that are not that, it’s okay to deploy and use your dollars to accomplish those things because we only get one spin on this thing. So, you might as well make the most of it while you’re here.

Humphrey’s Journey with Money (26:26)

Brian: I do want to, this isn’t part of the question, but Humphrey, I have to ask since we’ve got you sitting here. Bo and I are knuckleheads. We went through this whole phase where we even did this thing called Tightwad Nation because I was tight as a tightwad. I mean, I resembled a lot of Bianca of just the way I’ve lived my life. But I have as I’ve gotten more success I’ve eventually traded in my tightwad card because I have realized I spend more money on stuff and I felt like I was a hypocrite and I have a no hypocrite policy. What’s your journey like? I mean have you felt an evolution with how you’ve looked at money?

Humphrey: Yeah, I think I still err on the side of tightwad, but I am not opposed to spending money on experiences now because I think they bring you a lot of joy and fulfillment. Like, you know, just even running the marathon on Sunday, I stayed at a nice hotel that was close to the start line because I didn’t want to walk a mile to the start line, right? I will run 26.2 and not walk a foot further. So, I’ve become more abundant with at least the spending habits. I mean, my father passed away this year, but he passed away with more money than he should have, and he never enjoyed his life. Towards the end of his life, he was still eating frozen meals because that’s what he was used to. He just got conditioned. And he still wanted to fly economy even though he didn’t have to. And so I kind of looked at his life and I said, “Okay, how can I change my habits so that I at least enjoy a little bit of the money but still have some money for later and perhaps have some money for my future family?”

Brian: I love that. But your parents got to see all your success though.

Humphrey: Oh, yeah. Yeah. My mom’s still kicking it, so she’s good. She’s not a tightwad. She likes to spend the money for her. She’s like, “Budget? What’s that?” So, you know, I also grew up with a mom who was like, “Oh, what’s a budget?” And then my dad’s like, “No, don’t spend any money.” So, I got a really good balance of what’s right and what’s not right here.

Rebie: That’s awesome. Oh, that’s great. Well, Bianca, great question. Thank you so much. I will say, Bianca, you’re in this live stream. You’re saving 25%. A lot of people can’t or it takes a while for people to get those basics down. So, I love that you’re already there. And I think what the guys shared about potentially looking at your goals differently and doing those experiences was amazing. And go grab that download at moneyguy.com/resources, How Much Should You Save.

VTI vs Target Date Funds (29:40)

Rebie: All right, I’ve got another question for you. It’s from Derek S. It says, “As an early 30-something, would you consider it dangerous to be solely invested in something like VOO instead of a target date retirement fund? Should there be more diversification than one index?” What do you think?

Bo: This is going to stir the pot. Since you’re our guest, we’re going to let you take this one first. Young 30, all VOO, all equity. Is that okay?

Humphrey: So, I would question the target date retirement fund because if I’m not mistaken, you guys have to correct me here. Usually a target date retirement fund when you are 30 is like 90% VOO anyway, right? It’s 90% S&P 500, 90% market. VTI has 500 and change stocks in it anyways. So, I’ve always viewed that as pretty diversified, but I would like to hear your take on if you would add more bonds or fixed income into that portfolio as an early 30-something. It depends on his goals too, right?

Brian: I’m willing to go first. Look, Bo and I have even debated this and Bo makes some, I’ll let him kind of have the word on it because I tried to craft some rules where I was like 20-somethings, yeah, just go buy the total market or S&P 500. I think that those index funds are so strong. But Bo’s gonna get into the behavioral stuff that goes with why we say index target retirement funds is because look, we know in the beginning it’s just the behavior of starting the saving and investing because there’s such a battle of consumption out there for 20-somethings that people just don’t even start the habit of building 10% or 15% savings rates. So, the fact that we’re even at this discussion of having is it okay to do just index funds versus index target retirement funds, you’re so ahead of the masses on this because most people don’t even have the discipline to get that far. But I’m never going to beat up because we even gave advice. I had a studio tour who came through and I found out that their index target retirement fund was 10% bonds and they were 26 years old. And I was like, well, look, in the Roth accounts, buy VTI or buy the total market or whatever you want, and then that way it’s going to bring your total allocation to probably a 3 to 5% bonds, which now you’re not going to lose as much sleep about. So, you can even balance it out. But I’m not going to pick on you either way. I bet a financial mutant who’s asking in their 20s or even early 30s these two questions, you’re going to come out a winner both ways. So, we’re now getting into we’re splitting hairs.

Bo: Well, I think that when it comes to the advice that we give, we want to probabilistically set you up for success. We know that a lot of success in finance is based more on behavior than is based on actual mathematics, right? And so, I’m going to do this little exercise really quick. This will seem unkind. It’s not. Humphrey, at what age did you turn old? His response, oh, I’m not old. Yeah, I’m not old. So, Brian, at what age did you turn old? And you’re going to say, “Oh, I’m not old.”

Brian: Well, no, I’m going to say 50 kicks like a donkey. I don’t feel bad, but it’s just that everybody looks at you different once you tell them you’re in your 50s.

Bo: Here’s the reason why I asked that question. I would imagine everyone says, “Hey, I’m not old yet. I mean, maybe I might be old in 10 years.” And so, we all subjectively assign, oh, I’m still young. I’m still aggressive. I can still, my risk tolerance is still high. And so one of the problems I see with folks in their 20s, they’re VTI for life and they get really used to 12%, 13%, 14% annualized returns because that’s when they came through. And then in their 30s, they keep doing the same thing. And the numbers get bigger. And the bigger the numbers get, the bigger the numbers get. And so then they carry that into their 40s. Well, I’m still young in my 40s. I got 25 working years. I can still be 100% equities. Well, then you get to your 50s. Gosh, I’m not retiring yet. And you end up to where while there should likely be a glide path, it never actually happens. And so it’s not uncommon. Brian and I, we used to sit down with prospects and they’d be 65 ready to retire. We look at their portfolio and say, you’ve got 97% equities and 3%. And so then we show them, hey, we do an analysis. Here’s your current portfolio today and here’s what we’re recommending. They’re like, “Guys, I’ve been annualizing 15% per year, and you’re going to put me in something where I’m only going to make 7%, 8% per year,” and it’s a really hard adjustment to make. And then what happens? 2008 happens, and then you have fourth quarter of 2018, you have COVID, you have 2022, and there’s these significant downturns, and you really do suffer from a very real sequence of return risk in those early years of retirement, early years of financial independence. And so if we can build the behavior early on that diversification is not bad, taking some risk off the table is not bad. Having a healthy savings rate that can maybe compensate for me not getting the absolute best return possible every single year is not bad because when it comes to investing, when it comes to building wealth, it’s more about how much you get to keep over the long term than how much you make this month, this quarter, this year. And so if we can set that behavior, and I think the 30s is a great time to start thinking about that. I don’t think that’s going to be a bad thing.

Brian: I want to give some context. I think when you’re in your 20s and 30s, and I’m gonna make a plane analogy. We’ll bring your father, fighter pilot in here, too. In your 20s and 30s, you can put up with a lot and you just have the tolerance. You can do it. I mean, I make the joke all the time that it seemed reasonable to go on a trip and put 10 guys in one hotel room in my 20s. Now, if I don’t have an en suite, I’m like, what are we doing here? It’s just funny how your life will change. And I think about all my people who are VTI for life or some semblance of I’m just going to be wild with the aggressiveness all the way up until I retire. It is the analogy. That’s why I like the glide path because you’re landing an airplane of life. Can you imagine if you’re on a commercial flight and they are flying you in and then all of a sudden they tell you, “Okay, we’re quickly approaching San Francisco airport.” And then they dive on that thing. They circle it in and then skid it in and you’d be like, “Oh my god, the trauma you would have would probably make it where you’d never want to fly on an airplane again.” Because yeah, they got you in, but there was a lot of drama and a lot of things that really impacted you. Whereas, I’m telling you, as a person you’re going to change. Your life is going to change. Success is going to change you. You’re going to want a nice smooth commercial type landing where the pilot is slowly pulling it down to where when you touch down you go, “Wow, what a great landing. That felt smooth. That felt so good.” And you have no drama trauma that you took with you. That’s what people do to themselves with investing is that they’re doing it wrong. I mean, if you have to go to where you’re just taking all these risks and then it hurts, you didn’t do it right because a good diversified portfolio should serve you well when you’re young and aggressive and then it should serve you well when you get old and you’re starting to dial down the risk.

Humphrey: Yeah. I want to add one more and I actually have a question for you guys. You know, recently the stock market’s been phenomenal, right? And so that’s kind of what we’re used to right now. 80% of the time it’s phenomenal. And I’m thinking about those downturns that you’re talking about. Right now I have one individual stock position that’s up five, six times, right? And I don’t want to sell it because I don’t want to take these capital gains hits. What would you guys say to someone like me who has a lot of short-term capital gains and maybe they’re becoming long-term soon but I don’t want to take the tax hit?

Bo: Yeah, it’s a really hard thing because when it comes to buying individual stocks, I learned this very early on in my very first investments class. They say when it comes to buying individual stocks you have to make two decisions really really well. You got to buy at the right time and you got to sell at the right time. And oftentimes it’s that second one that’s really really difficult. Whenever we have a client who comes to us, hey, I’ve got this one stock position and I’ve made 1,000% or I’ve gone 5x on it or whatever. Okay. What would be more painful to you right now? If you’re at 5x and we saw this really bad downturn and all of a sudden it went to where you’re only up 2x and so you lost out on that. Is that more painful? Or what if you sold it today and you sold at 5x and it didn’t go to 10x? And we’ll ask that question. And so then a lot of times we’ll ask them which one of those is more painful for you. Okay, that’s going to tell me where your bent is in terms of holding it or getting out of it. And once we do decide, okay, maybe it makes sense for us to begin divesting out of this position. Well, then comes the how. Well, if I think it’s an all-time high right now, do I just sell that chunk today or do I want to remove emotion from the equation and say, okay, every month I’m going to sell this percent or I’m going to sell, every quarter I’m going to sell this many shares. Just like I dollar cost average into a position, I can dollar cost average out to try to remove it. If the stock goes up, great. I’ve still got holdings that are making money. If it goes down, it’s okay. I took some of my chips off the table. And you can approach it that way because what we want to prevent people from doing is being emotional and making this knee-jerk reaction that again changes the way their behavior happens in the future.

Brian: I’m going to make this personal because personal finance is very personal. You were successful. I imagine this thing, even though it’s up five-fold, is probably a small percentage of your total net worth. You might get benefit because I have one holding that I’m so proud of because look, I did the same thing. I bought Apple in 2008 and I talk about this in Millionaire Mission. I sold it after it doubled or tripled. Meanwhile, I have a childhood best friend who bought it. He still owns those shares from 2008. Holy cow. What those shares are worth. It is literally one of those stories where you hear people say, if you bought $1,000 worth of Amazon, it turns into a million bucks. Nobody does that. There’s a few people that do unique things like that. That’s why I highlighted it in the book, but I’m like everybody else. I sold Apple after I made two or three-fold when I bought it in 2008. Well, I have another, I got another lick that I hit in 2018. I bought a stock and now I’ve just decided it’s part of my permanent portfolio. I’m just, now it’s fun for me. Even though this thing, I really think this thing is, I’m at the path where this one purchase is going to be worth seven figures off of this one thing and I want to see if it’ll do it. I just want to see it. So it’s kind of a fun conversation piece but it’s such a small percentage of my total net worth it just doesn’t matter. So for me and I think for you, if it’s fun for you keep that. But if this was, we have people come to us all the time even with like an Nvidia where this is, but they worked for Nvidia and this is now 80% of their net worth. I don’t care how good a company is. We have to divest you of this so that you don’t have the Lucent stories and all these other things that I constantly give experience shares on. So for somebody like that then you have to get out of these investments to make sure it’s more balanced from a risk goal perspective. But for you, I think let’s, because do you know how many conversations I get to have about this stock that I bought in 2018 and now it’s going to potentially be seven figures at some point. I mean, that’s a fun little sweetener of life that you get to share.

Bo: But you can do it depending on how you acquired it. You get, there are ways to be sophisticated in how you dispose of it. You can do charitable giving with appreciated securities. You can do loss harvesting to try to offset it. You can sell specific lots depending on how you bought that. So just because you make the decision to exit a position doesn’t mean you have to take on a big tax hit. There are ways to get around that or at least to minimize that to the best of your ability.

Brian: And I even detailed, and I feel like I’m giving a plug for Millionaire Mission, which I am. My giving strategy uses a lot of appreciated holdings where I will dollar cost average into my same joint account kind of what I’m giving to the churches and other things because it’s just a really cool thing when you get to give those appreciated holdings and then push up the basis. It’s fun.

Bo: Can I tell you another behavioral thing I think is just wild that people do sometimes and I bet some of you financial mutants do this. Say I bought Apple in 2008, right? And say I bought $10,000 of it and it’s worth $20,000 now. I always tell, hey, if you’re charitably inclined, you’re someone who wants to give to charity, why would you not give that appreciated? “Oh, but I bought it in 2008. I can’t.” No, no, no. You realize right now today you have $20,000 of exposure. If you gift that $20,000 of Apple to the charitable giving account and then you go buy Apple today for $20,000, you still have the exact same investment exposure that you had from that stock you bought back in 2008, you just eradicate the gains. I’m amazed at how many people not only are anchored to the stock that they bought, they are anchored to the day that they bought it. And that is a fallacy because you don’t want those gains. You want to get rid of those out of your portfolio. So, even if you have a position you love and you’re thinking, “Oh, I would never get rid of this fill in the blank.” No, think about it. You can always just go rebuy it today and reset your basis.

Humphrey: Cool. That’s a really good tip slash tax hack. I love that.

Student Loans from Parents (43:28)

Rebie: Okay. I’ve got another question queued up for you. This one’s a little, I don’t know. I’m interested to hear what you’re going to say. Spicy. Oh, boy. A little spicy. Maybe. Maybe. You be the judge. It says, Sing Speak says, “I have low-interest student loans from my parents. I’ll be 24 when I graduate. So, how should I balance my investing and paying them off to preserve the relationship?”

Humphrey: Does this person mean that the parents loaned this person the money?

Rebie: That’s how I read it. Yes. So, it is true. There’s a mathematical component here. There’s also a relational component. So, I’d love to hear your thoughts.

Bo: I think I’ll start with this one as you guys are gathering your thoughts. I think, Sing, this is what I would say. Mom, Dad, I love you guys. But I went to moneyguy.com/resources and I downloaded the Financial Order of Operations deliverable. It’s a free copy. It’s a nine-step process of what I should do with my next dollar. And because I listen to these guys, because I listen to Humphrey Yang, this says right here that I should not begin paying off low interest debt until step nine, mom and dad. So, I’d love, but Mom, Dad, I haven’t, I’ve got to max out my Roth. I got to max out HSA. I got to max out my retirement plan. I got to be at a high percent savings. I’m just not there yet. But mom and dad, as soon as I get there, you are number nine on the list. And I think that’s the way I think that’ll work.

Brian: Humphrey, I have thoughts, but I want to hear Humphrey’s thoughts first.

Bo: I do too.

Humphrey: I guess my thought would be it depends on how fragile the relationship is. If it’s something that’s really important to your parents, maybe set up a little payment plan where monthly you spend a small portion of your income, not a large portion, very small. We’re talking $100 bucks a month, maybe where it goes back to paying your parents off and then maybe you can slowly amp that up over time. But I do agree with you that it should be lower on the priority list of paying off the low interest rate debt because there are a lot of better things you can do with that money, but it depends on your parents. Like, if they’re hounding you every month being like, “Hey, where’s my payment? I need that money.”

Bo: Where’s my money?

Rebie: I noticed there wasn’t anything about if there was an expectation set in this question. So have you already committed to something? Like have they let you know? So I don’t know. That’s probably a conversation that just needs to happen.

Bo: How low interest is this debt? Maybe we just refinance at a higher rate with mom and dad. Mom, dad, you gave me this at 2%. What if we refinance at 5%?

Brian: I will give the old man answer here because I’m the only one on this panel that has a 22-year-old daughter. Can I tell you one of the funnest things about being a parent is if you see your children model really good behavior, like critical thinking skills. So, if your parents had the ability to where they gave, were able to essentially fund college with a low interest loan. This is ripe fertile ground to have a conversation. That’s the first thing I do is if you have a good relationship is have a great conversation with your parents about exactly what Bo set up is that hey you know I’m starting out I want to do my Roth IRA I want to do this but also I feel this obligation because you guys have paid it forward to me to have this education I would love to figure out the balance. If you just have that conversation, do you know the tingle factor your parents will have? Like yes, this is what I’m talking about. It’s connecting everything I’ve done. And then I would say to your parents, I want to do something. Even though I know that this is a step nine of the financial order of operations, I believe it is so important for me to model. I don’t know if it’s $50 a month, $100 a month. I want you guys to see it as me honoring this gift that y’all have done, the investments you made, but I’m also I want you to know why it’s so low in these beginning stages. It’s more of a trophy or a token contribution to thank you for the gift, but then I’m still going to fund my Roth, my 401(k), and all these other things. And I guarantee because I know, I’ve shared another plug for the book. That’s how, I don’t mean to plug this, but I put all these stories in the book because I had, I was on the other side of this is that I remember when I got into my adult life, I realized very quickly how hard it was to be an adult and I got myself in some credit card debt and I had to call my dad and it was only like $300. But it crushed me to have to call my parents to ask and I remember when it was time when I called them back to say, “Hey, I’m ready to pay you back.” They’re like, “No, no, don’t worry about it.” You know, and I’m like, “No, no, no. This is a principled moment.” And I think if you could have those conversations with your parents because they made an investment in you and have a principled conversation, use this as a tool, man, the tingles I get just thinking about that as a parent, you will make their year because they’ll start to see man it took, the graft of what I was trying to imprint and share with the next generation because we know the stats. Every time we do the wealth studies and it comes from Millionaire Next Door, Dave Ramsey and them and all theirs and we’ve done 25,000 even in our own interviews of all the financial mutants, 70% to 80% of millionaires are first generation. So that stat only exists if we know the stats that between 70% disappears in generation 2, 90% by generation three. So if your parents, if they had the abilities to pay it forward, and now you’re actually breaking the trend that creates those stats that we all cite, they’re going to be very excited about that.

Humphrey: Good answer.

Rebie: That was great. No, honestly, that was a good variety of thoughts.

Rebalancing Portfolio (49:12)

Rebie: All right, I’ve got another question queued up for you from Makula. It says, “How often does Humphrey rebalance his portfolio? Any differences between what the Money Guys recommend?”

Humphrey: Honestly, not enough. For someone who makes content on YouTube a lot about personal finance, I admittedly have not rebalanced it in a couple years, so I should rebalance it this year. Probably at the end of this year. Ideally, I would be doing it once a year, but I’d love to hear your take.

Bo: Yeah. So, I’ll tell you the way that I think about this. One of the things I do is because I’m a contributor accumulator, I like to think about as I’m making contributions, I’m kind of naturally rebalancing in terms of the asset class. I mean, most of it’s on autopilot, but every now and then I might just kind of do a manual override. Hey, I need more small cap or I need more international, whatever that thing may be. For our clients, what we generally target is we will want to look at rebalancing generally twice a year, right? And there’s no science to that, but what we do is we review it. It doesn’t mean that we actually place rebalances, but we want to review the allocation with the eye towards rebalancing. And a lot of times it might be, okay, hey, our large cap target is 47% and you’re at 48.2%. Yeah, we’re not going to rebalance that. We’re going to allow that to be in an acceptable range, but we’ve at least investigated, right? And then when the market gives us opportunities, we want to make sure that we take advantage of those opportunities. So, a lot of people don’t recognize that in 2025, this has been a fantastic investment year. It’s been a great year for investors. In April, we were down like 19% off the high. So, if you were someone who was recently buying or you’ve recently allocated some dollars, there was a good chance that you had a huge opportunity right there in April of this year to do some loss harvesting, to do some rebalancing, to allocate your dollars in a different way where you could take advantage of that. Now, that’s not timing the market. That’s being tactical in how you think about your rebalancing. So we look for, in a just a normal boring year, looking at it twice a year. But in years where we do see those big intra-year declines, we want to be kind of dialed in. Is now a good time for us to get back to target or make some tweaks that we maybe have not made?

Brian: I’m willing to be confessional and tell you that I do a better job and I know all of our advisers here do a better job with rebalancing than I do for myself is because it’s part of our direct process what we do for clients. For myself, I will say because I have a no hypocrisy policy. I like to be transparent with you guys. It’s once a year because I do my annual net worth statement once a year. I do charitable giving off of appreciated holdings that I have and so forth. So, those things naturally create when I do the net worth statement and then also when I’m doing my just truing up my annual giving, those are perfect rebalancing opportunities for me to kind of think about it and those create those. So, I am doing it, but I’m not doing it as much as if I was a client of the firm. I’m just being confessional about that. But it’s once a year would be my answer.

Humphrey: Love that. Well, you guys have inspired me for sure. I should probably rebalance.

Rebie: I think there was a lot of alignment on that one, honestly.

Brian: Well, create a process. I mean, that’s everything in my life is try to create a system or a process. That’s probably why we came up with Financial Order of Operations is because I just love thinking about money in a methodical way. So it really makes the good habits that much easier and the bad habits that much harder because human nature is we let our emotions and all these other things come into play. So if we can create a system that takes all that out, even if you’re not doing it as well as you could, it’s still getting done.

Bo: Now a brief aside only because I think from an investment perspective this is an interesting thought process to go down. So when you rebalance you’re really making two decisions. I’m making the decision to sell something and to buy something else. Well, we believe as investors oftentimes momentum is a real thing that happens in the markets. There are markets that momentum will carry an asset class on. So, I’ll use the large cap example again. It is not uncommon for us to look at a rebalance. Okay, this is supposed to be 47%. It’s at 48%. If I were to sell that 1%, is there something else in the portfolio that’s compelling right now for me to buy? Or if there’s nothing compelling for me to buy, I might be okay allowing my portfolio to drift a touch. Now, this is where there’s a little bit more of an art there than a science, but I don’t want people to get so dogmatic in rebalancing they think, “Okay, I’ve got to place trades today.” Because a lot of times, depending on the fund, there might be charges, it might not be an inexpensive thing to rebalance. And so, I don’t want to see you selling $7 of this, I’m going to go buy $4, $3, and $1 of this. That math doesn’t math. But I want to make sure that when you make a financial decision, when you make a decision in your portfolio, there’s a reason you’re making it. You’re not just making it for the motion of it.

Brian: Well, I get upset. I’m not going to name names, but we name them. Asset location is important because when we do asset allocation, obviously in your retirement accounts, you’ll put your fixed income because they’re taxed a certain way. And then in your Roth accounts, you’ll put growth assets. So we’ll do asset location within different account structures and there is a custodian that does, because we work with clients who might work with a custodian or an employer that gives them advisers for free and they take that as an executive benefit. And we have these custodians that we’re like no no in this retirement account we want this allocation and they’re like no no our fiduciary responsibility won’t allow us we have to and we’re like oh my god you knuckleheads. So this is why sometimes as financial planners you have to be careful with being too dogmatic where it needs to be more practical of what’s the total plan, what’s the why, does it fit into the personal finance situation because a lot of these people they’ll create a system that’s a system for the sake of being a system without really thinking about the whole picture.

Humphrey: I agree with both of you. I think you got to really think for yourself too and not just follow a rule because someone on the internet told you to.

Brian: That’s coming from three guys on the internet right now.

Humphrey: So, you know, make sure it fits you and personal finance is personal as you guys said earlier.

Rebie: I like you kind of threw in there that you at least look at it. You don’t always have to do the thing. I think that’s a great point.

Sharing Financial Numbers (55:33)

Brian: Hey, do you share your numbers? Because I mean we take some flak is that I don’t share my income. I don’t share my net worth completely. I’m not so transparent.

Humphrey: I stopped sharing?

Brian: And I’m like, do you not have relatives? I had people coming up to me like, “Oh, how’s your Palantir position doing?” I’m like, “I just want to—”

Humphrey: Yeah. That’s funny.

Too Many Individual Stocks (55:59)

Rebie: All right. I’ve got another one queued up from Mr. Quest. It says, “Can you be too diversified with individual stocks? I’ll hear a new stock and invest in it, but feel like my money’s spread too thin. Would it be better to focus on a few strong stocks instead of many?”

Bo: I’ve got very strong feelings.

Brian: We’re going to let Humphrey—I knew you guys would, having watched enough of Humphrey’s content. I know we’re going to differ a little bit.

Humphrey: I think if it’s held within a Roth account, you know, I’m loving the few strong stocks instead of many. But, you know, I think I have more of an aggressive approach to things. I don’t know how many individual stocks this person has, but I do think that if you’re going to be diversified with 60 individual stocks, you might as well just buy an ETF at that point.

Bo: I love that. I love that so much. That’s my take.

Humphrey: I personally like to have a few strong stocks in my Roth IRA in addition to an index fund and I like the aggressive approach that I take and the fact that oh maybe I can have a lot of tax-free gains. But that’s personally what I do. Would I say that that’s what everyone should do? Probably not. I think again at the beginning of this live stream I said it’s probably better to just set it and forget it and not look at it. I probably would have been way better off right.

Rebie: What do you think of how he said, “I’ll hear a new stock and then invest in it.” Because I know Brian and I are gonna say something about it. So, I’m curious what you think about that.

Humphrey: I think that you should probably be doing at least 30 hours of research before you buy a new stock. Just don’t, you know, if your mom says to buy a new stock, you just go for it. I’m curious to know what he hears about.

Bo: Oh, I heard that this one made 20% last year. I need to buy that. That’s the way that I base my investment decision making.

Brian: Okay, I’m just going to say I don’t love individual stocks now because look here’s the reality of the situation is when you start having some success and then you start having a growing family, time is just something I don’t have a lot of anymore. So when to hear Humphrey say you got to invest 30 hours to buy a stock, I would end up with just a portfolio of cash because I would have nothing because I don’t have 30 hours to go find the next stock to do it. So, I have to create things, the behaviors that will force it. And that’s what I always, I just hung out with a buddy of mine who moved back to Chicago and we were talking. He’s like, “Man, I am so much better off since you got me buying index funds.” He goes because, when people find out you do finance, they think that the first thing, what stock are you doing? I’m like, I don’t know. I’m buying an S&P. I’m buying an index fund for myself. And so he would tell me, I remember we used to have so many conversations about Fitbit and all these other things and finally I was like, what are you doing? I mean, you’re successful, you have, you’re doing all these things, just buy the index fund. When we were on this trip recently, he’s like, you know, I’m so much better off. He goes, when I look at how my index funds are performing, and I don’t have to put any effort into it whatsoever, it just, I feel like I got time back. I got emotional value back. I mean, there’s just a lot of things. So I look, I think it’s like most things on your maturity with something. This makes me sound like an old man on a porch too is that when you find a new concept, if you come from humble beginnings and you just now understand about investing, you’re going to be just so fascinated with the process that I get it because it’s a new hobby, it’s a new thing. But I’m just saying when the practicality of it because you look at the SPIVA research and everything else, the index funds outperform the active managers and you’re more than likely not going to do better than the active managers yourself. So if you’re thinking about this is actual eating money, this is going to be your retirement money, then I like index funds, ETFs, mutual funds, you choose your delivery method. If this is fun because you truly do get so much value out of it, treat it like a hobby, but don’t let that be the vacation money versus the eating money and automate the behavior.

Bo: You know, I have a good buddy, he’s been in the industry. He’s a very successful financial adviser, has been in the industry for a long time now, but when he first became a financial adviser, he was early on trying to figure out how this all worked. And his dad let him take over a portfolio for him, right, because dad wanted to support him, whatever. And one of the very early things he did is he was able to sell SMAs, like these separate account managers who were selling individual stocks.

Brian: Oh gosh, he’s talking about me. Keep going. I was doing so good. Keep going.

Bo: Thank you for hearing this thing. I’m going to have this separate account manager going to buy all these individual stocks and stuff, right? Well, what ended up happening inside of this advisor’s father’s portfolio is he’d be like, “Son, why do I own $7 worth of this? And why do I have $9 worth of this? And why is my mailbox just full?” Or today it’d be why is my inbox just full of all these prospectuses. It was not adding a ton of value. And frankly, managing a large stock portfolio is pretty difficult. I mean, if you’re someone who does direct indexing, it’s a difficult thing to manage that well and to make sure that you’re not getting off on tracking and that sort of thing. And so, it’s hard. So, before you do it, understand why you’re doing it and make sure that it’s worth it. Because this same advisor I’m talking about, he was also an accountant. And so, he did a ton of tax returns. He said one of the most annoying things in the world is when he’d have one of his stock-picking clients that’s a trader that would have 500, 600, 800 transactions throughout the course of the year and every single one of those had to show up on his tax return, right? And you’re talking about buying, selling, buying, selling, and it was just an absolute nightmare. So, a lot of times, make sure when you implement these types of strategies, is the juice actually worth the squeeze that it’s going to take?

Humphrey: I saw a really funny post on the internet yesterday on social media and the title of the post was, “Do you think my accountant will be mad at me?” And the screenshot was 5,523 trades, profit and loss, $80.

Bo: Yes, your accountant will be mad at you.

Brian: Well, fortunately, everything’s automated now, so you can upload that stuff a lot easier. So, you save yourself tons of money. But I want to give some context because I think a lot of you, I want to save you the journey I was on because mine was, there’s a purist of thought on this is that when I started working, the second firm I worked at, super high net worth individuals, a lot of Fortune 500 founders, a lot of professional athletes, celebrities and others. We were managing the money for them and when I found out I could get access to these separate account management accounts that such wealthy people were using and my dad’s, I mean it was barely over $100,000. But that was the minimum to get access to these managers. I was like, I’m going to do my father a solid because we don’t come from money. I’m going to get him into this stuff because this is what rich people get. So, if it’s good enough for the rich people, it’s probably going to be better. And then because I was new to this whole process too, even though I’m managing money, working as an associate adviser at this large firm that’s doing all these celebrities and Fortune 500 people, I quickly realized, oh my gosh, this thing, it’s more about the sizzle than the practicality of it. It just wasn’t as good as what the brochure said. Now it’s fun to market this stuff because you’re stroking the ego of rich people telling them we’re going to give you something that the general public doesn’t get and we’re going to lock you up for seven to 10 years while we do it. You don’t say that part out loud, but this is what you get when you do these type of structures. And I thought I was doing my dad a solid, but then I quickly saw the warts on this thing. And that’s why even with our wealth management business, we run billions of dollars here. I don’t do a lot of the private deals because I saw that and like I said, it’s back to the no hypocrisy policy. I try to treat your money like if it was my money and I learned something very valuable by seeing, doing what rich people do is sometimes more about the brochure and the sizzle than it is about actually the result that you’re getting at the end of the day. So I didn’t want y’all to think that I was out there doing, I mean this is my heart really is trying to, but I learned something by putting my own father in that stuff and I was like gosh what am I doing?

Rebie: No, I think the three of you gave a good picture of the places where some version of this strategy might be really good, but you have to know yourself. Personal finance is personal like you’re saying and there’s reasons that we talk about some of the more automated things because that is going to set a lot more people up for success than some of the really specialized complicated things. So I loved that. Mr. Quest, thank you for the question and thank you to everyone who joined us for this special live stream with Humphrey.

Closing (1:04:50)

Bo: Is that it? We’re already out of time. We’re out of time.

Brian: Oh my gosh, Humphrey, you’re the secret sauce. I feel like the time just moved. It was a blink of the eye.

Bo: What are you saying on the normal show? I know. I’m like now I see the timer up there. I’m like, how did an hour pass?

Humphrey: I’ll send you an invoice. Okay.

Rebie: That was lovely. And even though we’re turning off the cameras right now, we’re going to record even more awesome content all together. So, be sure to subscribe to Humphrey Yang’s channel and the Money Guy Show channel because there will be videos featuring all three of these wonderful gentlemen coming out soon.

Brian: You’re on our platform right now. Is it live stream? Anything you want to share with the audience? Anything you’ve got something that you want them to know about?

Humphrey: No, I mean I’ve learned a lot from you guys and I appreciate you guys having me on and I’m excited to use the collab feature on YouTube which is brand new. So basically it means we can post together. So I’ll have a video on my channel, these guys will have a video on your channel and you’ll get to see more content. Thank you for tuning into the live stream. Is there anything else we need to say?

Brian: Well, I don’t mind sharing because I know when we had Aaron come on, people in the comments they beat us up like why didn’t you guys do more than just that with Aaron? We have more stuff we’re going to be doing, too. So, there’s more to come. This thing, I just got attacked by the microphone. We have more that’s going to be coming your way. So, we’re not going to be squandering this great opportunity because we know what a special thing it is to have Humphrey in studio today.

Bo: Yeah. And so, more to come.

Brian: Thank you. Thank you for joining us. I’m your host, Brian. God, this thing keeps coming at me. Joined by Mr. Bo Hansen and of course, Humphrey Yang. Money Guy Team out.