In this episode...

  • Navigating the 2000 Dot-Com crash and the 2008 Global Financial Crisis.
  • The "arcade game" methodology of hitting startup milestones.
  • Why self-directed IRAs are essential for investing in precious metals, crypto, and real estate.
  • How a first-generation upbringing creates a bulletproof entrepreneurial mindset.

In this episode, Tarek sits down with serial fintech founder Henry Yoshida. From surviving the dot-com crash at Merrill Lynch to selling his startup to Goldman Sachs, Henry shares the tactical playbook he used to work around Wall Street’s gatekeepers. They dive deep into the structural limitations of modern retirement accounts, why the public stock market is shrinking, and how Rocket Dollar is helping regular investors use their IRAs to buy real estate, startups, and precious metals.

Key Takeaways

  • Find the Corporate Blind Spot: At Merrill Lynch, Henry survived a 90% washout rate by targeting a market the firm had ignored: small-business 401(k)s. By building a shadow sales force of payroll reps, he created a bulletproof book of business while his peers cold-called millionaires.

  • The Sir Mix-A-Lot Strategy: How do you get VC funding without a pitch deck? You manufacture hype. Henry rented out a canceled VIP room at SXSW, hired Sir Mix-A-Lot to perform, and drew the attention of top-tier investors to seed his company, Honest Dollar.

  • The Public Market is Shrinking: Twenty years ago, companies like Amazon went public with revenue of under $30 million, allowing retail investors to capture massive upside. Today, companies stay private until they hit multi-billion-dollar valuations. Henry argues that if your IRA isn’t accessing private alternative assets, you are missing today’s growth engine.

  • Fail Into an Acquisition: Sometimes the best exit isn’t an IPO. Henry candidly discusses how Honest Dollar hit a funding wall, prompting a strategic pivot and the sale of its highly valuable IP to Goldman Sachs (which became Marcus Invest).

  • Embrace the Risk: Growing up as the child of working-class immigrants gave Henry a distinct advantage: he wasn’t afraid of being broke. Escaping the “golden handcuffs” of corporate finance is easier when you realize you can always survive the fall.

Notable Quotes

“I learned in about the third hour of the second day that this is not a finance job. This is actually a sales job… Everything is tied to marketing, advertising, and sales.” — Henry Yoshida

“We actually failed into an acquisition by Goldman Sachs… but that’s a good thing. People made money, we returned money to the shareholders. We took a shot at building something.” — Henry Yoshida

“The Amazon of tomorrow is not currently trading on the Russell 3000 index today because they don’t go public. They have private capital to stay private.” — Henry Yoshida

Mentioned Resources

Concept: The Regret Minimization Framework (Jeff Bezos)

Company: Rocket Dollar

Financial Strategy: Self-Directed IRAs / Solo 401(k)s


0:00 - 0:18

Henry: I think that the only way you can win is to be a continual investor. The one thing I might shift is that since now just public market securities represent a subset of the overall investable marketplace. I think that the investor of today just needs to expand what they can do with that money.

0:19 - 0:28

Tarek: Welcome to Y'all Street. Today, we speak with Henry Yoshida, a serial entrepreneur and the founder of rocketdollar.com. Henry, would you like a cup of coffee?

0:29 - 0:30

Henry: I'd love a cup of coffee.

0:31 - 0:42

Tarek: I, uh, I got you this special rocket fuel coffee mug because of your company, Rocket Dollar. And it has the added bonus of having a nice reference to the state of Texas with NASA.

0:42 - 0:43

Henry: Okay.

0:43 - 0:45

Tarek: So there you go. Nice and black for you.

0:46 - 0:48

Henry: I'm a Dallas kid. I've actually never been to NASA.

0:49 - 0:50

Tarek: Well, now you had a reason.

0:50 - 0:53

Henry: Now I'm closer in Austin and you'd get down there to the kids.

0:55 - 0:58

Tarek: So Henry, you're born and raised in Texas.

0:58 - 1:06

Henry: I am. So, um, I guess people would see me, they hear me. They don't think I'm a native Texan, but, uh, yeah, born and raised Dallas, Texas.

1:06 - 1:06

Tarek: Where's your accent?

1:08 - 1:20

Henry: So, um, both my parents are Japanese, but they met here in America. And by the time my brother and I were born, they just happened to be in Northeast Dallas. I was in an area called Garland. So close to Richardson, Plano area.

1:20 - 1:21

Tarek: What brought them there?

1:22 - 1:27

Henry: Uh, you know, it was just kind of moving across the country. I ended up settling there.

1:27 - 1:29

Tarek: It wasn't like a job or anything.

1:29 - 1:45

Henry: It wasn't a job or anything. They actually ended up, uh, like a lot of, a lot of kids in my area that were Asian American, they, they came there. They were part of that restaurant industry. So my parents actually growing up, uh, uh, I fulfilled their wishes. Cause the only thing they wanted me to do was just to grow up and not work in a restaurant essentially.

1:45 - 1:56

Tarek: So my background is the restaurant business as well. My, my mom and dad were both in the restaurant business and I spent a lot of time hanging coats and, you know, running, running tables and all that kind of stuff.

1:56 - 2:15

Henry: So I never had to work cause my, um, actually made me think a little bit about business because my mother spent her entire working time working at a Benihana. So that was like business at the time and we would go there. So the only thing we did, we never had to work there. But, uh, my brother and I used to see how long we could drink out of a soda gun directly.

2:15 - 2:16

Tarek: Oh my gosh.

2:16 - 2:19

Henry: Either we didn't trouble or we create a mess. That Neil one was good.

2:20 - 2:48

Tarek: My, uh, growing up in the eighties after school, uh, elementary school, I would go over to my dad's restaurant and the restaurant had this gigantic bar and, uh, I would sit at the bar and they would have those little like cocktail swords for the Shirley temples that were just like completely filled with sugar. And I would sit there and drop back like six Shirley temples at the bar as a six, seven year old while, you know, waiting for dad or waiting for mom to pick me up.

2:48 - 2:52

Henry: So when you're in a Japanese restaurant, you have those little mini umbrellas with the toothpicks.

2:52 - 2:53

Tarek: That's right.

2:53 - 2:56

Henry: As the umbrella stem. So those are really fun to give out in school.

2:56 - 2:57

Tarek: So you still have family in Japan?

2:57 - 4:00

Henry: Uh, so all of our families in Japan. So when my parents came over, they actually got kind of, uh, um, lost contact with a lot of the folks in Japan. So we weren't really close. We couldn't really afford to go visit them. They were far away. And, uh, at the time in the, when they first came to America in the 1970s, and I just read this in a book too, but, um, it was not a great time to leave Japan because it looked like Japan was going to take over the world, right? So they were a little bit ostracized from the family and then due to financial reasons and working in the restaurant business, you don't get any days off. So we were a pretty small nuclear family only in the Dallas, Texas area. So not a lot of extended family, just my brother, myself, my mom and dad, and they're both passed. But, uh, so now it's just my brother and I, but you've been back to Japan since. We've been back, but not necessarily to go see that part of the family. So I say it's ready to go. We went back there a couple of times to spread ashes and so forth, but not to reconnect with that family because we never knew them growing up. So it didn't really add anything for me personally.

4:00 - 4:21

Tarek: So, so growing up then, um, you're in Garland, Texas and what was, what were you thinking as a young man, like what you wanted to do? Did you have ambitions, goals, dreams, hopes? Did you play sports? Well, what was life like,

4:21 - 5:04

Henry: Uh, played a lot of sports, but, uh, never really organized through the school or clubs like they have now for, for my kids. Uh, everything we played was at the rec center that we could walk to because our parents worked all the time. So yeah, we were limited to the sports that were there. So that was a lot of basketball, ping pong, and tennis were kind of the things. And you played ping pong where you're waiting for your turn in the basketball courts. We got pretty good at those sports. Um, and then growing up just seeing them in the restaurant business, it was more just deciding that, Hey, school was a path out and not wanting to do that. So maybe that's pretty typical of that. Maybe Asian American children of immigrants, but because they didn't have any exposure to the world, you know, they didn't really fit into, they didn't come to the United States to go to college and so forth and work at a, at a company. So there was no framework for them to talk to us about, uh, you should probably study this or that.

5:04 - 5:17

Tarek: Uh, so same for me being first generation, you know, from a Lebanese immigrant and my mom was first generation herself. So yeah, kind of coming up through that immigrant culture is, is a challenge because you just don't have a lot of mentorship necessarily.

5:18 - 5:54

Henry: Right. And you don't know, for example, right. We're able to tell our children that, you know, you should maybe think about doing this or studying that, or let me help you understand the programs. And, uh, you know, myself and my brother navigating, that was very, no, no guidance, no understanding trailblazing yourself. Right. And probably quite frankly wasted a lot of time because you didn't know. All right. Uh, and so forth, but that was the upbringing, but it was, it was great. You know, I think the one thing that did rub off was that you saw them work really hard and they didn't want you to have to work that hard for not as much reward or security or safety or future.

5:54 - 6:07

Tarek: Yeah. But you do certainly appreciate the work ethic and yeah, I'm sure as we'll get into here, I guess on, on this pod, I certainly, it looks from the outside and that, that that was pretty heavily instilled in you about your parents.

6:08 - 6:40

Henry: It was. And then, you know, the other part too was maybe not necessarily needing to just be comfortable at the time either. Cause I think that's what it takes. If you break out from, let's say the corporate job, which you did too and go and start a business and so forth, like you have to be a certain type of mentality to want to go take that chance. And the people that are willing to take that chance are the ones who realize that, I mean, don't really need a safety net. Cause didn't have that growing up. So like, you know, to, to get knocked off the horse, you've been there and done that. Cause you started on the ground. You didn't start on the horse. Like some people.

6:41 - 6:49

Tarek: No, that's a great point. And I, I feel that myself. And even in my own story, just the highs and the lows. And it's like, well, I've been here before. I've, I've had no money before.

6:49 - 6:50

Henry: Exactly.

6:50 - 6:51

Tarek: Not a big deal.

6:51 - 6:51

Henry: Right. Right.

6:51 - 6:54

Tarek: Um, so where did you, where'd you end up going to school?

6:54 - 7:32

Henry: Well, you know, like a lot of kids, uh, I wanted to go to school, like, you know, with the brand name schools, the fancy ones go out of state. But, uh, at the time you, you know, when I was in school, I had gotten a letter. I was an automatic acceptance with a partial academic scholarship to the University of Texas. My brother was only 22 months behind. So we pretty much had no choice, but to take that deal. It was the best deal then. Um, and when you say automatic acceptance to these University of Texas back then the state universities, and this was now 25 years ago, but they would just send you a letter to say you're accepted. You all, you had to do a send an administration check for like 50 bucks back and you already have a spot.

7:32 - 7:33

Tarek: No way.

7:33 - 7:37

Henry: Uh, so at that point I could spend the,

7:37 - 7:43

Tarek: That's not the case now though, right? Because you have to be at like, you know, top of your class, like top 10% of your class or something like that to get an automatic.

7:43 - 8:09

Henry: They change it now. They take, it started at 10 in Texas went to seven and now it's at five. So gosh, it's, it's even more competitive. But, uh, but I think it was a different era then and just pretty much made every other choice irrelevant from a cost standpoint, but the cost of going out of state. But you know, in hindsight, I never had gone to Austin at all growing up. Uh, I had no concept of college cause either one of my parents went to college, but yeah, it was a great experience and taught me a lot.

8:09 - 8:15

Tarek: And well, it's like going with foreign country when you're in Texas and you go to Austin, that's, it's a completely different culture.

8:15 - 8:34

Henry: It really was. I mean, cause even then it was still 30 some odd thousand students. Now it's in the mid fifties, I think second only to Ohio state university, um, in terms of enrollment. But first time I'd met people, I remember I, I have first year, I lived in a Jewish dorm, so I had Jewish booze. I didn't really experience any of that growing up in the area I grew up in in Texas.

8:34 - 8:36

Tarek: Yeah. And I'm sure they didn't spend a lot of time with Japanese.

8:36 - 8:48

Henry: No, I'm not where they were from. But even being Japanese, it was unusual too, because where I grew up, we were the, my brother and I were the only Japanese American. We was a heavy Vietnamese American population or Vietnamese population.

8:48 - 8:48

Tarek: I remember that.

8:49 - 8:58

Henry: So there were one third of my schools growing up were Vietnamese and we were the only Japanese. There were very few, you know, Chinese and almost no Japanese and so forth.

8:59 - 9:21

Tarek: So yeah, I say I remember that because I spent five years in Forest Lane with a Texas Instruments. So yeah, on and off, because I had gone to Silicon Valley for a little bit. And, uh, I spent a lot of time in Japan because, uh, Osaka and Tokyo is where a lot of our engineers there and we go back and forth. But, uh, to your point, it was a heavily Vietnamese area, not so much, uh, you know, Japanese or Chinese area.

9:21 - 9:51

Henry: Exactly. Yeah. So in a way it was a little bit of being in, I don't know if it was necessarily an outsider, but ironically enough, I felt like I actually fit in more with, uh, just more Americanized kids growing up because I was able to talk exactly like them and don't really have the Texas accent, but I don't have an accent from a, from a foreign country either. So yeah, it's just kind of stuck with me. So I've been good at fitting into those traditional molds and I probably took that into the working world to going into financial services or seeing if I wanted to get into government and so forth.

9:52 - 9:59

Tarek: Yeah. So that's what I was going to ask next. So you get to college and you're thinking to yourself, man, I'm passionate about retirement accounts.

10:00 - 10:29

Henry: No, not at all. So again, when you have parents that don't work at a company of any sort with no retirement plan, um, I didn't even have a concept of what those were. So after college I actually wanted to go into law school, but couldn't afford to go. So I had to get a job for a little while. That job I took was at, uh, at Merrill Lynch. So the idea for me was to work for a couple of years, try to save some money, um, pay off some of the debt from undergrad and then go to law school and try to become a lawyer.

10:30 - 10:35

Tarek: But, uh, now did you go, you went straight from UT directly to Merrill Lynch?

10:35 - 10:46

Henry: I did. Yeah. So I worked at another small place first just to get licensed. And then I used that to actually leverage getting the interview and getting again at Merrill Lynch and in the year 2000.

10:46 - 10:51

Tarek: Okay. At what point I thought I read that you'd been in Washington DC as well.

10:52 - 11:56

Henry: I was, uh, so in terms of trying to build that college resume while I was at the University of Texas up for getting into law school, uh, I did internships. So I grew up in Texas. Uh, we never really traveled as a kid. So I'd never been out of the state. Uh, and then going to Austin was the first time I'd never been out of the state. I went to Japan for family purposes, but that was just to go visit family members that couldn't communicate with, uh, when big family milestones happened. But I grew up not really, uh, with, with great feelings towards them. Right. Cause I almost felt like they kicked my parents out of the family. So I didn't really have much interest in talking to them. But other than that, we didn't do the road trips or go to New York city. Yeah. I never did those things. So finally in college was when I decided that doing an internship or doing internships and leaving school for one year, uh, while trying to build up my resume was a way for me to see another part of the country. And so I picked, there were trimesters, spring, fall, and summer. And I applied for a bunch of internships. And I thought I would just accept the ones that were in the same city and try to get a lease or a sublease on an apartment for a year. And that happened to be in DC for a year.

11:56 - 11:57

Tarek: And where in DC did you work?

11:58 - 12:08

Henry: So I worked, uh, I did two consecutive, I did the White House. And then I worked for, uh, what's called the public defender service. So that's the, uh, Miranda rights. If you can't afford an attorney, one will be appointed to you.

12:08 - 12:09

Tarek: Oh goodness.

12:09 - 12:31

Henry: But in the Washington DC, it's a district, not a state or municipality. So the attorneys on the prosecution side are us attorneys appointed by the president. So the defense side, the ones that even come for free, actually have to be pretty high level of people. So it turned out to be a great internship. I wanted to be an attorney. And so got into some competitive internships at the white house and this one.

12:32 - 12:36

Tarek: And what was it like working at the White House? What was that experience like? Well, and what, and what year was this?

12:37 - 12:42

Henry: So this was 98 99 timeframe. So it was the middle part of the second term of Bill Clinton's presidency.

12:42 - 12:45

Tarek: This is like right around the Monica Lewinsky time.

12:46 - 12:55

Henry: Right after. So we were after, so everything had already happened and we were getting scrutinized. So it was probably weirder to be the after because you were constant.

12:55 - 12:56

Tarek: Did you ever meet Monica Lewinsky?

12:57 - 13:32

Henry: Uh, one time. Yeah. So they, they do like little receptions where you meet the old classes because the old interns teach the jobs that they were doing to the new, is that kind of awkward or, uh, a little bit awkward. Yeah. So, but the, the thing is that she was, uh, just one of maybe there were 250 of us and they came from all these schools. A lot of elite schools, a lot of them were pretty well to do, well connected families and so forth. So there were a lot of interesting, interesting people, you know, children of movie stars, children of us senators or nephews of someone. So CEO and so forth.

13:32 - 13:35

Tarek: So, so is it highly competitive to, to get into those internship programs?

13:35 - 14:08

Henry: It was competitive. Uh, you, so I'm not still actually, I'm quite sure how I got into those things, but, uh, it, it was super, super competitive, but it was a great experience because there's a portion of the folks that get this internship actually work in the White House. So there's two buildings there. There's an office building that's inside the gates, but it's not the White House. It sits next door. And then there's the White House. So when you get there, there's 250 of you and a hundred of the 250 who actually had jobs inside the White House. The other 150 will work, uh, uh, outside. I say of it next door.

14:08 - 14:20

Tarek: And what were your parents thinking? You know, here their son, first generation that moved to the United States and their son is working in the White House. Was that, was that special for them? Did they ever talk to you about that?

14:20 - 14:46

Henry: Uh, they did, but I don't know that they really had a concept. I mean, just he, for, for better or worse, I would say that they had trouble assimilating into the culture here, the United States. So, I mean, this, this is true. I don't know if a lot of people that aren't the children of immigrants understand this, but, uh, there's those people they'll come here and they'll be here for 40 years, but they find these pockets. And in this case it was the restaurant community, which were the other Japanese people that they knew. None of which lived in the same area, Dallas as me.

14:46 - 14:46

Tarek: Yeah.

14:46 - 15:12

Henry: But that allowed them to never have to like really try to full on become a part of American society or like fully learn the language yet still function as a green card holding citizen, uh, with all the rights of the natural born citizen. So even some of those things that didn't really dawn on them, like what we were doing, like everything we did, my brother and I was probably more based on what we'd read about, what friends of ours had done and so forth. So.

15:13 - 16:06

Tarek: Language is a real barrier. And, uh, when I lived in South America, I moved down there and I didn't speak a lick of Spanish at all. And what inevitably happens is, you know, you run into the store, you hear somebody speaking English and they're another expat and they become friends and that's your community. Those are people that you're hanging out with because you can, you, you can really have shared experiences and communicate well. And I, I think, you know, to some extent it really slowed down the, you know, my, my learning with respect to Spanish because I had this sort of safety matcher. And so it's hard, it really is I think hard for a lot of people who are native to the United States to really understand what it's like being an immigrant or a stranger in a strange land. And, you know, sometimes, you know, if you, if you marry somebody who's from that country that will fast track you to assimilation, right? When you don't have that, when you have two parents from the same country, it can be very difficult.

16:06 - 16:36

Henry: So I don't know that they really understood a lot of those things. Uh, you know, friends and friends, parents understood it, but it was a cool thing. Uh, because one, if they came to visit, which they did, but my parents couldn't really afford to get away, I could basically give them a tour of the White House. Yeah. Well the White House tour was a public one. And then you're able to do it publicly. You can't now, now you get special tickets and you know, and so forth. But back then it was public, but I could take them into the non East wing side of the White House, which is where the working stuff happens.

16:37 - 17:02

Tarek: Yeah. It's, it's interesting. So you were talking about, after you graduate, you immediately start working for Merrill Lynch. And it's interesting that the timing of it is 2000, 2001. And that's when the security around the country changed when the, you know, touring the White House changed, get to go into the airport, right. So everything changed around this time. So I am interested in this transition. So you, you, you go through UT, you get hired by Merrill, the year is 2000.

17:03 - 17:03

Henry: Right.

17:04 - 17:05

Tarek: And, and what month in 2000?

17:06 - 18:13

Henry: So you graduate, so it's May. I think we were starting in like August. So by then, you know, we were full on into this internet bubble bursting. So it was hard because, and mind you, when I started working at Merrill Lynch, I guess it was a very famous, well-heeled finance company. And I thought it was going to be a finance job. I thought they're going to learn business. That was one of the, maybe the first realities of the real world where I pretty much learned in about the third hour of the second day that this is not a finance job. This is actually a sales job. Your job is to go try to get clients and get them to give the firm money, not for you to be, you know, these, a fancy hands portfolio manager and manage money for folks like they actually, we didn't have any experience to do that. So I learned it was a sales job. And I think that realization hit me that almost everything that you might do in a work capacity has some component of sales. And I really don't care what your job is. And I use this example when I talk to, when I talk to other folks, but just think the last time you went to the dentist, they're, they're dentists. So they view themselves as medical professionals, doctors, but end of the day, they are always trying to sell you stuff.

18:13 - 18:13

Tarek: Absolutely.

18:14 - 18:26

Henry: And then that same day, same week, you decided to go get your oil change. They're trying to upsell you on other services that your car may or may not need. It exists in every job, whether you're a dentist or you work at a Jiffy Lube, right?

18:26 - 18:28

Tarek: Cause everything is tied to my, everything is tied to money.

18:29 - 18:48

Henry: Everything is tied to marketing, advertising and sales. And that, that finance job actually made me sort of realize that, okay, the only way to actually make this thing work is to go sell clients on becoming customers of Merrill Lynch. And then Merrill Lynch has a product suite that would cater to whatever their financial actual product needs. Or that wasn't my job. My job was just to get them a door.

18:48 - 18:51

Tarek: So how did you feel about becoming a salesman?

18:51 - 19:00

Henry: It was hard cause I'd never done it before, but I realized that, uh, you know, going through the trials and tribulations of becoming a salesman seemed a lot better than being broke and fired.

19:00 - 19:05

Tarek: So would you say that that's something that doesn't come naturally to you? You consider yourself an introvert extrovert?

19:06 - 19:25

Henry: Well, I, I guess, uh, I've been asked this question a lot before, so I'm probably like an extroverted introvert, uh, in a sense. So I come across jovial, nominative, um, uh, and open, but yeah, at the end of the day, I'm also still shy and would prefer a lot of times to spend time by myself and think about more than anything else.

19:26 - 19:40

Tarek: And so you're this young college kid, you're 22 years old and you've been hired by this major firm. This is a, this is a great opportunity for you, a leg up, you know, as a first generation and transition into the world of finance in the United States. And now you're in a sales job.

19:41 - 20:40

Henry: Exactly. Yeah. Because I didn't know to study business. There's my undergrad, right. I was trying to do pre-law and some things to cry law school and so forth. So I didn't know that there was a track because you know, if you had parents that had been through the college system, they'd probably be able to tell you that, Hey, at a major university, they would have an undergraduate business school and you could get into that track. You don't need the MBA, but that would allow you to get into a more traditional finance type role. I didn't know that. Um, and so I was working at a finance company, but it wasn't in a finance type role. It was a more sales role and business development type role. And it was a tough time in the economy. I was working in Austin, Texas, and I basically had to figure out a way to, to pass the sales program and not get fired because the numbers were typically about, you know, 10% would make it through and most of them made it through by virtue of being swooped into a team inside of Merrill, an existing one, not getting new clients into the door. They would just get transitioned accounts from an existing financial.

20:40 - 20:52

Tarek: So that, that whole period of time. So just to, to, to bring people back to it. So August of 2000 stock market has been, it's sort of running on fumes from the peak of the.com boom.

20:52 - 20:53

Henry: Right.

20:53 - 21:18

Tarek: Um, by, by March of 2001, it's warning signs everywhere. And then by September of 2001 it's 9-11 and it's just right. Whammy after whammy after whammy. And now you are in a sales role where you have to, you know, increase revenue for the company. So how, how do you, how did you handle that? What did you do? Well, were you nervous?

21:18 - 21:24

Henry: Uh, well, I didn't have anything to lose, so I don't know if I was nervous. I just kind of nervous in the sense.

21:24 - 21:24

Tarek: If you lose your job.

21:25 - 23:08

Henry: Yeah. But 90% of the people that are in my program are going to lose their job anyway. So, um, so that was kind of an expected, you know, the methodology done was to kind of just put a bunch of people into the program and see who passes and so forth. But for me it was very difficult to go get high net worth individuals to open an account with an inexperienced, uh, new employee who had no background in financial services, trying to talk to let's say single digit and a millionaires to open up account brokerage accounts at Merrill Lynch. So I, with a lot of people, I think that the easiest thing to do is start to look at the rule book and figure out a different way to play the game. So they had provisions and rules and regulations for the sales program. And it turned out that, um, it wasn't a hack, but it's what changed the course of work. Maybe it started the course of my career, but I figured out that a small business retiring plans counted. And that was a little bit less of a trying to convince one wealthy individual to work with you and in this inexperienced young recent college graduate, but you could help them set up a 401k plan for their small business through the payroll provider. And I'd never even talked to those people individually. So we talked about this a little bit before in the prep for this, but I just learned that I could basically talk to the representatives who are also recent college graduates of the payroll companies and tell them that I was an advisor at Merrill Lynch. And if they ended up selling payroll services to a small business, let's say 15 employees and under was typically their market. Cause they were the recent young college graduates that if they wanted a 401k, if they actually put my name and ID number, then I would be the financial advisor on that 401k plan. So, uh, I did that and passed the program of flying colors instead.

23:08 - 23:13

Tarek: And you're offering your buddy Spiffs on, on,

23:13 - 24:20

Henry: I gave him a hundred bucks in cash. So nice. And probably bottom beers. So that's what I did. And they would just know my little six digit ID number. And I became the, so you created your own sales force essentially, essentially, but if it didn't mean anything to them, it was an investment product. So they couldn't get paid for it anyway, but it meant a lot to me. And so by the end of that 2000, 2001, those two 24 months, which it was a two year program, uh, I'd been the manager of about 95 to 105 small business 401k plans all between Austin and San Antonio, all businesses under 10 employees. And that was the start. And then the realization hit me that I have parents who have no retirement savings cause they work in the restaurant industry. Um, so I didn't grow up in a household knowing about IRAs and 401ks, I better get smart on this stuff and become an expert on it. So then that became the learning curve. And over the course of 10 years of Merrill Lynch, I became very well known for how to sell this type of business, how to manage that type of business, um, and how to position these 401k plans. I just became this 401k guy.

24:21 - 24:31

Tarek: What, what was your, you know, your primary message internally and externally during this time over, over 10 years, what was your message about 401ks and IRAs and retirement?

24:31 - 26:02

Henry: Well, and this is a message that's more related to personal finance, but the thing I loved about it was that the firm itself wanted you to go work with people who are already wealthy, right? So that was one of the things about financial services that you learned was that one, it was a sales job. And two, you really were working in an industry that already catered to people that had money. The thing I loved about 401k plans, it kind of aligned with my background personally and growing up, which was it was a way to help people with their money that satisfied the requirements of a Merrill Lynch, a well-heeled financial services company, but actually be able to talk to regular people and make a real difference. So I used to give a lot of presentations. So the joke was that, you know, these a hundred companies over time. And then I got more after that, uh, put me in a position to where I was intimately aware of the lunchrooms and break rooms of most midsize companies in the corridor between Houston, Austin, and San Antonio. I've been in all of them because I give these 401k enrollment meetings. And I always told them that there's going to be a few of you in this room that will never remember who I am, but you're going to sign up for this 401k plan and put some percentage, maybe like seven, eight, nine, 10, 12% of your salary. And you're going to be in your early part of your career. And you're just going to get used to it. You're just going to get used to living without that money. Just like people are used to getting a chunk of their money taken out for tax withholding. And in 25 years, it'll be the single best decision you've ever made in your life from a money standpoint. And you'll have no idea that you started it in a break room over, like I said,

26:02 - 26:03

Tarek: You're like, so here's my business card. You call me in 25 years.

26:03 - 26:17

Henry: So when you want to send me my 2% side, uh, uh, for giving it this like sage advice, you know, here's how you can find me. I'm pretty certain that I'll keep my email addresses. My first name, last name at so-and-so.com. So it should work 20 years from now.

26:17 - 26:18

Tarek: Oh, that's great.

26:18 - 26:35

Henry: And so forth. So that was the main thing. I love that I figured out a way to help and be impactful to main street, normal working individuals, you know, people that probably it would have changed the course of my parents' lives. Had they met someone like that, but still do it within this Wall Street firm.

26:36 - 26:40

Tarek: Yeah. You found a niche part of the, the overall umbrella.

26:40 - 26:48

Henry: Yeah. And I loved it. I thought that these retirement plans were basically the way that, you know, Americans build wealth, um, from a money standpoint.

26:48 - 26:54

Tarek: Yeah. And the vast majority of, of wealth, if I'm not mistaken, is in retirement plans of some sort. Isn't that right?

26:54 - 27:12

Henry: Well, the current numbers today, you know, um, I work in the IRA industry. Now I've worked in the retirement and IRA account industry for now, ever since those days in Merrill, but there's about $34 trillion in retirement accounts and these are US retirement accounts. So that's IRAs 401ks pensions. So this is a large, large chunk.

27:12 - 27:16

Tarek: And what percentage of the total invested assets is that do you think estimates?

27:16 - 27:41

Henry: So it's probably about, you know, one fifth, but the part that's held outside is held by wealthier individuals because there's caps on what they can put into retirement plans. But if you talk about, let's say, I think the better way to look at is if you talk about, um, middle-class and working America, it is their number one vehicle now, right? It's what they rely on for their savings because also in 2025, they're, they're very unlikely to have corporate pensions for themselves.

27:42 - 28:05

Tarek: So it's 2003, 2004, you start building this unique business within Merrill and things are progressing. Things are moving along and we're coming right up on the heels of yet another major financial crisis seven years later. Um, well, what was it like living through that? And obviously Merrill Lynch factors pretty heavily into the events of that time.

28:05 - 29:23

Henry: Sure. Um, well, and this one was broader. I w I would actually argue that I happen to be in Austin. So that was a town that was maybe over indexed to getting affected by internet bubble bursting. Cause a lot of people worked in technology, um, at that time. So it affected them maybe more than it might have the broader economy. But in 2008, I would say it affected everybody. Um, that was a much bigger crisis that hit more broadly. But you know, the funny thing was that the part of business that I've built up actually was very insulated against this because it was, it did all the things that you probably should do in your own personal investing and savings, which was a set amount as a percentage of your salary on a set biweekly weekly or monthly basis. And no matter what's actually happening in the markets, if you're going to, if you're going to bet that at some point the global economy or the global GDP is going to be larger at some point in the intermediate to longterm future than it is today, then it's a solid bet to keep doing these incremental timed interval investments at a certain amount all the time going forward. Um, and the reality is if you don't think the answer, the answer to that question, what I disposed is no, then whatever money you'd have in the bank isn't going to matter anyway. You should be like canning water and living in a bunker or something worse.

29:23 - 29:24

Tarek: Do you think it's that extreme?

29:24 - 29:35

Henry: Well, I'm just saying that it's, you know, obviously I'm being sarcastic, but the thing is that if your bet is that the world is going to be terrible 20 years from now, there's no point in investing in saving for anything.

29:35 - 30:05

Tarek: Well, even you can even make the argument that let's say over the next 20 years, the stock market doesn't go up like it has over the last 35 years. Even if the stock market is flat, right? You can make the argument that you're still, you know, stocking away money. You know, it's not earning you a return necessarily, but the savings aspect of the principle behind putting money into into retirement is still there. So the, if you're capping what the downside risk is relative to the outside, obviously everybody knows the compounding value at the upside of a retirement account.

30:05 - 30:05

Henry: Right, right.

30:06 - 30:10

Tarek: But the downside is minimal unless, as you're saying, it's an apocalyptic scenario, right?

30:10 - 31:22

Henry: And there've been periods, but I mean, really, you know, by and large, uh, even if you're taking a one point in time measurement and another point in time measurement, 20 years down the road, that doesn't mean that there were movements up and down a lot of way. It just might've been like some sort of peak up and down. So it doesn't mean that people couldn't have lived off of those. And, um, but you know, the reality is that now that the retirement industry has shifted to where the responsibilities on the individual is saved for that, that's what, you know, really motivates me to stay in this industry thinking that, okay, now effectively companies, governments have put the onus on the individual to save a portion of their salary to be able to live and sustain themselves in retirement. Well, that's a pretty noble calling to, to kind of build everything that I the industry I've stayed in over my career. And I love that part. I still feel like I'm always talking to people about the benefits of that. And it's almost auto saving, pay yourself first. You think about the future and put away a dime of every dollar, you know, kind of the richest man in Babylon type of mentality. If you've ever read that book, sure. Buy it for your kids. You know, it's, it's all the 56 pages paid them 25 bucks to read it. Like I did for my kids.

31:22 - 31:33

Tarek: So picking it back up, it's 2008, 2009 things are, are wild. Um, what is it? What is the experience like at the company? People frightened?

31:33 - 32:21

Henry: Well, so first of all, no one knew. Uh, I remember the exact weekend that everything sort of fell apart and all the financial services. So this is like Lehman going away, Merrill Lynch going away. Um, you know, Washington Mutual, all these companies, Bear Stearns, all of them actually went away in the same weekend. So I was actually at a work training conference in New York for Merrill Lynch the Thursday before. And you know, they, you know, we're just a group within Merrill Lynch, but they get the senior, we're talking like exec execs, right? Like the Chief Operating Officer, the fern comes in, uh, you know, kind of gives the hurrah talks to us in New York City or he shows up for 10 minutes and leaves. But I'm just thinking that considering Sunday, uh, I flew from there to then go get prepared to talk at a conference in Orlando. So I didn't even come back to Texas. I was on the plane.

32:22 - 32:23

Tarek: What is your position at this point?

32:23 - 33:10

Henry: So at that time I was just running my own group with a partner, but I'd had this side gig inside where I did do training internally to teach people how to develop as a time and play business from there. Let's say CFO and CEO clients that they already had just a way to sort of get additional business for the firm. So I did that on the side, but I stayed in New York and then decided to fly to Florida as opposed to coming back. And I remember, you know, kind of coming down on Saturday, Sunday, the conference was going to start on Sunday night. By the time I landed, you know, the notifications that come out that the firm had been acquired is now part of Bank of America. And I had just seen maybe two of the top five executives. I mean, it wasn't a meeting that I have them, but I saw him speak and I'm thinking that there's no way they would have been there doing this three days before they knew.

33:10 - 33:13

Tarek: So I'm guessing it was like being a professional athlete and getting traded.

33:14 - 33:35

Henry: Yeah. So when I spoke at that panel conference, right, I wasn't technically sure, you know, what company I worked for like Bank of America or Merrill Lynch. So I just introduced myself as Henry Yoshida of Merrill of America. You know, I said, there's a joke, you know, you think a long time ago someone told me you should start with a little icebreaker joke. We had giving a public talk. And so I just made up a new company name and just went with it to that panel discussion.

33:35 - 33:38

Tarek: But surely thereafter you start your own company. Isn't that right?

33:39 - 34:32

Henry: Well, uh, it was a couple of years later. So, um, you know, we geared up to where now was a part of Bank of America. We had all corporate clients, my team and I. So it, quite frankly, it became a little bit of a conflict because Bank of America was so huge that they had a lot of corporate banking and business banking business with the same clients that I had companies I had clients. So giving investment advice on one side was perceived as somewhat of a conflict when you're also providing banking and lending services to that same company. So there was a plan that sort of unwind ourselves of it, you know, split some of the clients up and just go and become an independent registered investment advisory firm. So we did that in 2010. So about two years after, and at that point, you know, I think they almost fully gotten rid of the, the name and the brand, but so it was a good time to transition. It was the right time to start an RIA. It allowed me to continue doing that retirement plan consulting business, uh, and to keep growing on that part.

34:32 - 34:35

Tarek: And what a great time we get into wealth management coming right off of the lows.

34:35 - 34:35

Henry: Right.

34:36 - 34:39

Tarek: Yeah. Moving, moving into a, a nice little tailwind and equities.

34:39 - 35:08

Henry: That's right. And then there was also big too, for that was a big period where a lot of people were leaving the big brokerage houses and then taking some portion of their client base and starting independent firms. And that oddly enough, that seemed like an unusual thing. Like it seemed better to be at the big firms. But now I think there's more people that would be in the audience listening to the podcast. If they work with a full service financial advisor, odds are now they work with an independent person who uses a back office clearing of one of the big, of a big name, but I'm not someone who's captive at a big firm.

35:08 - 35:08

Tarek: That's right.

35:08 - 35:10

Henry: It was the complete opposite pre 2010.

35:11 - 35:11

Tarek: Okay.

35:11 - 35:12

Henry: So.

35:12 - 35:22

Tarek: Interesting. And so, uh, so you're running this RIA, you're, you're getting clients, you're working with a partner here. And then how, how does the first startup come about?

35:22 - 35:49

Henry: Well, it, the, the RIA grew pretty big. So it was just that it was kind of the same thing. And, uh, maybe for me, I go back to the, Hey, it's worth taking a chance. And I wasn't sure that that being an advisor for the rest of my career, um, was something that was going to be super fulfilling. I mean, it was mid thirties and thought that if I was going to make a move and I'm young enough to do this, now I'm a little bit of security. Now's the time to take a chance.

35:49 - 35:52

Tarek: You'd been doing pretty well financially at this point. So you had security.

35:53 - 36:20

Henry: And so I wanted to, and then I thought about that what's another way to be impactful in this retirement industry. So that was what, what really drove me. So came up with the concept and teamed up with a, with a co-founder, um, had, I'm not even sure I'd call it like a pitch deck, uh, per se, but maybe just an idea. And, uh, we, we got qualifier where you got offered venture funding to start this idea. There was effectively like a mobile app based small business retirement plan.

36:20 - 36:27

Tarek: So, so I'm not interested in this. How did, so you're saying you don't have a pitch deck, but you, you get approach for funding. Like what?

36:27 - 36:29

Henry: Well, we approach the people.

36:29 - 36:30

Tarek: So you approach the PR base.

36:30 - 36:37

Henry: We have a word out there that we were, you know, seeking out and that, Hey, there's this thing called venture funding.

36:37 - 36:47

Tarek: Who are you, who are you saying this out to? What is, what is the pitch process like? How quickly do you get the money? I mean, there are a lot of entrepreneurs that listen in to this podcast. They want to know the details, the dirty details.

36:47 - 38:03

Henry: We lived in Austin, Texas. Um, I'd had, you know, the consulting business, the RIA, I sold my stake, uh, in it. My partner at the time he had sold his stake in a mobile app development agency to big firm as well. So we, we were known in our town and there's a big conference there called South by Southwest. They have a component of depth for interactive, where there are a lot of investors that come in. So we, you kind of have to wave your hands in a way. And let's say digital way, they'd get people's attention that you have this new business or you have this new concept. So the way we did it was that we looked at the, the agenda for the conference and there's a startup pitch competition. Um, we were too late. We didn't enter the startup pitch competition, by the way, but we noticed that one of the celebrity judges, um, or two of them, one was Elijah Wood, who actually is a DJ. So really, yeah. And, uh, and then another one of the judges was Sir Mix-a-Lot. So two people you wouldn't expect to be in the same panel, probably not the most qualified people to judge startups. But, um, we decided that we would actually do this dumb idea to throw a, a party and see if we could hire one of those two to basically just play a couple of songs out of it. Like maybe we can get them on the cheap. They're already in town.

38:03 - 38:03

Tarek: Yeah.

38:04 - 38:25

Henry: Um, so that's what we did. We basically just threw a quasi launch party for a company that we didn't have, but just to get attention. And so we did that. Sir Mix-A-Lot said he would play. So he played, a lot of people found out that we were starting this company, had a decently cool name and we own the domain called Honest Dollar. And then that set us up to go get meetings with folks.

38:25 - 38:32

Tarek: So you got Sir Mix-A-Lot to play a private party for a launch for a company that you had not yet started.

38:33 - 39:11

Henry: It was, it was one of the bars at the bottom of the W Hotel. If you've ever been in and the way we got that on the cheap was that we found out that there were big companies that were renting the space before. But at South by they sell these in three hour blocks and they realized that the two big tech companies are arch rival nemesis. Uh, and they didn't want to have adjacent blocks. So they were willing to just walk away from their deposits and go somewhere else. So we were able to pick it up for just the other half crazy. And then just convince, uh, I remember, you know, at the time, emailing a getting at the W-2 form or W-9 from Sir Mix-a-Lot.

39:11 - 39:13

Tarek: It's not weird. Hilarious, you should have that framed.

39:13 - 39:20

Henry: They're like, yeah, sure. You know, they, they literally have a W-9. He's, you know, you should get paid on. So it was like, this guy has a W-9, but on him.

39:20 - 39:26

Tarek: So, so what was the result of the party? So Mix-a-Lot's playing. You got a company that, yeah, it was a little bit.

39:26 - 40:04

Henry: I mean, if it's only all of 10 minutes, because all you had to do was come downstairs, still gonna go back out, but got the attention we wanted, set up some meetings. And lo and behold, we got offered like the seat capital to get the business started. Nice. And got it up and running. Uh, have the concept, got the money to build the platform and get that launch, but not enough to like really go to market and go get customers. So the IP was valuable and it made the evaluation that we were a little bit late in getting that up and running, but the IP and the licenses that we had were valuable. So there were potential suitors and acquirers for that versus going, getting another round.

40:04 - 40:04

Tarek: So, yeah.

40:05 - 41:41

Henry: Um, you know, for those in the audience that are, that are aspiring entrepreneurs, especially on this venture capital side, it, this is a weird analogy about how this game works, but the, it works very similar to those, uh, those car racing video games that we used to play when we were kids, like the ones that would actually built a car. So you start the race and you get the allotted time and you have to get the checkpoints and that's the only way you get additional time. Um, but the, when you get to that checkpoint, the more time you have hitting that checkpoint gives you a better chance of going into that next stage. So like, it's the same thing with venture funding. So if you get a couple million dollars or a million dollars or 500,000 to start or 5 million, depending on the business, the quicker you can get to a milestone or a checkpoint of that business to get to that next level for a C plus around the series A or series B, the more money you have left or the more momentum you have heading into that checkpoint and you get a new allotment of either capital or resources and so forth, the better your odds are of hitting that third checkpoint. But if you are barely getting across a one second, uh, and my favorite game as a kid was outrun. So if you remember that one, sure. Right. The, the red car, uh, the red convertible Ferrari. If you got to that checkpoint with only one second, the odds of you making it to the next checkpoint are very low. But if you hit that checkpoint with 18 seconds, you had a very good chance to get to the next one because you had 18 plus the new time. And for us, there wasn't a lot of resources when we got to that checkpoint. So it just, the business decision was better to start looking at the potential acquisition. So that's what we did. And there were suitors because we had one milestone accomplished that was going to save time.

41:42 - 42:11

Tarek: So I want to hear how, how you approach the suitors. But before that, this is a big transition for you because you have all of the backing of this gigantic company behind you, Bank of America. Um, and you spent your whole entire career at these massive organizations, but now you have a startup and so you need IP and you need to develop some technology and a website. What was that process like for you? We did you, was it a divide and conquer with you and your business partner? Or was this an area that you had to really dive into and learn? Or have you always been technological, uh, by nature?

42:11 - 43:50

Henry: We weren't, I wasn't the technical side, but it was more, uh, understanding the product, understanding the nuances and like knowing the retirement market and then finding out like, where's there a gap? Where's there a place where existing incumbents didn't really want to build a product, right? So the one thing I like doing small business retirement plans is that when I started doing it way back in the early days of Merrill, these were gigantic fortune 100 payroll companies like paychecks and ADP publicly traded triple a credit ratings. And they had to work with small businesses because small businesses also needed payroll because there was no online platform like QuickBooks online in the early two thousands. Um, but they didn't really want that business. It wasn't very profitable. They wanted to go get, you know, Texas Instruments or where you worked, for example, the big, big companies. Um, so same thing with the retirement plans, all these big insurance and investment companies didn't really want the small business one. So it was developing a product that sort of fit into that. Um, and seeing if you could fill that gap because quite frankly, the big incumbents don't care. So if you think about business, right, if you nibble away at a piece that no one cares about in the incumbent space, you have a chance to like, you know, grow and expand. I mean, at the end of the day, the great companies of today, they kind of started that way. Right. And I mean, I am just thinking that that the blockbusters of the world and the movie studios didn't think anything about Netflix when they were first starting. And now look, right. Uh, it's completely flipped, right. It's because they were able to sort of get critical mass and size and get started or get started, then get size and then get critical mass before the incumbents even realized that the market had shifted on them. Right. Um, because truth be told human nature is that things are going great. You have a very big interest in incentive to not change anything.

43:51 - 44:09

Tarek: So you had some really great IP that was set to transform this section of the industry. And you realize that you weren't really in a position, you were a little bit late, the timing wasn't right. And you said, let's, let's go ahead and sell this while we can and while we can still get max dollar for it. Is that right?

44:10 - 46:11

Henry: It was the best way to get returns for everyone that was involved. And it was a small group at the time. So we didn't have a wide list of stakeholders, right? We had some small, you know, venture capitalists and a couple of angel checks. So it wasn't like we had to get the approval of a large group of folks to do something like you would in the public markets with a major corporation. Um, it was just economically the right thing to do. So we made that decision and ended up being a very large suitor. So that turned out well, but it was Goldman Sachs. Yeah. So it wasn't Goldman Sachs. Um, but you know, I do tell people and to be real transparent and honest though, it's funny that, uh, uh, I look back on that experience and think that we actually failed into an acquisition by Goldman Sachs, but that's a good thing, right? Like, uh, people made money. Uh, we returned money to the shareholders. We took a shot at building something. It didn't work out. And had I never left that corporate world, you, I, I wouldn't know, but I left that corporate world because I thought to myself that, well, I could always go back to it. If I really wanted to start an RIA, I get offers to start or join RIAs today, like the investment firms, uh, and then go try to build a new client base. Even though I don't currently have one, I guess they figured that I can go develop one pretty quickly based on what I've done in the past. And that, that part's always there. If I wanted to go back to that and, you know, I'll go back to what you said that the part of Merrill Lynch, I worked at, I talked about this early on that it's a sales job. Um, um, what people don't realize is inside of those organizations, you're actually running in building your own business underneath the umbrella of a big company. So we actually competed against the same people that were down the hallway from us in the same office. Because if I got some multimillionaire client in a well to do part of the city where my office is based, that means that someone else down the hall in my own company also did not get that client the same way that the person across the street at another brokerage firm also did not get that client. Right. So it's not, we didn't work on this one large team.

46:11 - 46:14

Tarek: Yeah. Uh, we are cannibalizing each other's businesses.

46:14 - 46:36

Henry: We effectively built little small businesses within, which is exactly why you could, you saw the big brokerage houses see a mass exodus for people building independent firms, because the individuals who worked with these big firms develop relationships directly with the clients, right? If they could leave and throw up their own shingle and get the back office services provided, the relationship was one that they had not preferred.

46:36 - 46:41

Tarek: Right. And that was the rise of all the TAMPs that came up to support all of those. All those RIAs.

46:41 - 47:02

Henry: Exactly. Yeah. So that, that stands for turnkey asset management program. But, uh, I tell people when I look back on it and say that actually, you know, my business card may have said that I worked for a big company, but I almost feel like that actually taught me how to be an entrepreneur within my company because everyone's building their own individual book and, and, and so forth. So, and I think that that exists in more companies that people realize.

47:02 - 47:12

Tarek: And so you had some, I'm, first of all, I'm really interested in how you got connected to Goldman Sachs in the first place. Were you, were you working with an intermediary, an MNA firm or?

47:12 - 48:35

Henry: No, we were, we were way, way too small. Um, they were actually just building a consumer platform, uh, in private. You know, they, they obviously were working at the very high end in investment banking, super high net worth individuals. So not beyond high, high net worth, but, um, they were launching this platform at the time. It was called Marcus. Uh, they since renamed that. Yep. But, um, and they had a list of things they want on their platform. One of which was going to be investments. That was an ancillary thing. The one they started with was, uh, signature loans is what they call it to compete against, you know, Sofi as initial primary business at the time. And then a high yield savings account came after that. So today the high yield savings account is what they had, but they had envisions for this entire platform to capture that, that sort of like new generation of wealth. And at the time, this was 10 to 12 years ago. So this was when millennials first got tagged as millennials. I mean, yeah, I mean, you know, again, I've done four instances in this recording where I'm kind of aging myself, but I think to myself now that the, uh, that the oldest millennials are now 44 years old. So again, kind of blows your mind to think about that. But, you know, 10, 15 years ago when they were coining this term, you know, that was like the new emergent wealth. The idea was that they had these high paying jobs at big tech companies, plus they were potentially, some of them were going to inherit money from aging boomer parents.

48:35 - 48:43

Tarek: And that was Goldman's focus. So you, you kind of fell right into their lap. And that was an opportunity for them to, well, and it applies on, on that market.

48:43 - 50:01

Henry: It was. And, uh, you know, for us, we, we had to do some sort of transaction because there wasn't additional capital at the time. So it just kind of worked out in both sides. I mean, they were probably like a very opportunist opportunistic acquirer, but the timing was right. The deal was good and so forth. And it just cemented for me that, um, that although there's uncertainty in being an entrepreneur, I like the idea of taking that chance. Like I always go back to, to maybe like one of the greatest of all time. It's like a Jeff Bezos, right. And very famously, you know, he had at the time inflation adjusted in the late nine, in the late nineties, mid like, mid, late nineties, right. He was working at D E Shaw like as a, in the finance world. So it wasn't an engineer as a finance guy. Brilliant. But you know, his own boss, D E Shaw himself, a very famous like Wall Street legend person actually talked to him and said, why would you leave this high paying, you know, high potential trajectory, uh, income job to go do what you're doing. And he said, you know, the only thing for me is that when I'm 80 years old, I don't want to sit there and say that I never tried. So I'm quitting and I'm going to sell books online. And remember the term online probably wasn't really well known. So I was like, what do you mean online? Like, you know, people can buy books through a computer on this thing called the internet.

50:01 - 50:01

Tarek: Right.

50:02 - 50:10

Henry: Uh, and you know, he took that chance, but he was smart enough to where if he completely failed at that, he probably could have gone back and gotten a job in banking.

50:10 - 50:42

Tarek: And, and you know, we, we talked internally a lot about just behavioral biases and change is very difficult for a lot of people. And the safety net of working at a large company is sometime a magnet that's too attractive to, to pull away from. And here you, you started your first company, you had a positive exit. You went through the, the, the, the beginning, middle and end stage of it. And certainly I'm sure learned a lot. And that was probably the setup for round two for the next company.

50:42 - 50:42

Henry: Right.

50:43 - 50:43

Tarek: Which was what.

50:44 - 52:58

Henry: Well, so, you know, round two, uh, after that startup was okay. Think of things differently. It actually made me think about the market and who the end customer was. Cause the problem was that, um, Honest Dollar was going after a market that probably wasn't attractive enough to these like big companies. So what's a way to stay within the retirement space, fulfill a need that the traditional incumbent. So you got to think about, it's like a, not a squat analysis, uh, which is like the strength, weaknesses, opportunities and threats. But I think about it differently, which is the, where can you position yourself in this market to begin? So you think you're, you think that where someplace in the existing industry that none of the major players care about right now, um, what's part, what's another, what's could also benefit from maybe being modernized and digitized and what caters to a customer base that if you could cater to them and acquire them is attractive to just generally a lot of people, whatever that industry is. So that for me became owning private and alternative investments in an IRA, because those were typically held by higher net worth, higher investable asset people. They were private and alternative investments. So none of the traditional broker just cared about that because they made a lot more money packaging, uh, uh, public equities and stocks and bonds into like manufactured products in the form of mutual funds and selling those down to their clients and so forth. And because of that, they just didn't care and it presented that opportunity. So it was attractive customer base for any industry, right? So I, I think about it that the people who buy self-directed IRAs are the people who spend $400 on a Sunday afternoon at Costco. They have some sort of status at Marriott Bomboy and can basically take a vacation once a year to someplace out of the country. That's an attractive customer base, like to Nordstrom, to Tiffany, to Marriott, to Southwest Airlines, to Costco and so forth. High, middle, middle, high Americans in above, uh, traditional brokerages don't care because they are making so much money doing the traditional stuff. And there's no digitization or modernization. We talked about this too, that the existing self-directed IRA providers are antiquated. Well, they're a little more than like a website with all paper processes on the backend.

52:59 - 52:59

Tarek: Right.

52:59 - 55:27

Henry: And so forth. So I looked at it as an opportunity that, Hey, I could go into that space, create a business, um, and basically make it just as easy to buy private and alternative investments in an IRA as it is to go by Tesla and meta platform stock in an IRA at Fidelity or through your financial advisor at Merrill Lynch. So that was the vision for the company and the value proposition of the market. It's just in the value proposition and thinking that the shift is going to happen to where in this shift was happening prior to when I started working in finance. But the reality is, and this is to go back to that other Amazon example, I've talked about this in a lot of interviews that, that Amazon went public when they did sub $30 million in revenue, um, less than 25 years ago. So that means that had you known about the company, you could have purchased that stock and people did, but actually looked like it was going to go bankrupt. If you look at a lot of finance books and Wall Street Journal articles from the early two thousands, every analyst on Wall Street was actually picking the eBay would win because they were just selling other people's existing stuff and had no cost of carry. Amazon's going to go bankrupt. Right now you flip back. It's one of the largest companies in United States history, but it was available to anybody with a brokerage account at sub $30 million in revenue. But what's happened since then is now companies because of private access to private capital do not go public until they do hundreds of millions in revenue and have billions of dollars in valuation. So I think like anyone on your podcast, unless they're, let's say some connected BC invested in open AI, SpaceX Star Link Uber, uh, it was public now, but all I'm saying is that none of these companies go public. So the number of public companies that are available to invest in is actually a fraction of what it was 20 years ago, even though the markets are there. So thinking for me is that someone has to figure out a way to allow private investment, uh, uh, investment money to go into private investments in an easy way. And we talked about this about 15 minutes ago, which is that the large majority of middle America's money from an investment standpoint actually sits in retirement accounts. So 34 trillion overall in retirement accounts, 16 and a half trillion of that is an IRAs and another seven and a half is in 401ks and 401ks typically you're rolled into IRAs. So now you're talking 23, $24 trillion effectively only investing in the same S & P 500 companies, of which the top eight make up 30% of an index currently.

55:27 - 55:37

Tarek: Right. Yeah. I think I just heard a statistic that something like 68% of companies in the S & P 500 actually trail the index in terms of overall performance.

55:37 - 55:47

Henry: Right. And then if you look another, like, uh, usually every maybe decade or so about 10 to 15% of them actually just completely go away. So we're not talking about getting kicked off the index. We're talking about literally disappeared.

55:48 - 55:58

Tarek: That's right. So yeah, actually it's, you know, one of the reasons why we met and we were talking about precious metals and how precious metals are becoming a big part of people's IRAs.

55:58 - 55:58

Henry: And right.

55:59 - 56:12

Tarek: You know, when we look at the price of gold, let's say from the over the last 25 years from 2001 to present, the return is 1,137%. Whereas the S & P 500 inclusive of dividends is about 570%.

56:12 - 56:13

Henry: Right.

56:13 - 56:28

Tarek: And a lot of people are not aware of that. And so giving access to people to diversify their retirement or to some alternative assets or, or different vehicles or private placements, like you're saying different companies or entities or who are out of you is I think a tremendous value.

56:29 - 57:46

Henry: Correct. Did you got to think outside of this a 60% stock 40% bond framework that might've worked decades ago? And, and personally I'm a very traditional investor and maybe that's because in my professional life, I'm a little bit over indexed to alternatives and so forth and private companies. So in my own personal investments, I've probably over indexed the balance overall out into public security. But I think that people need to understand that there's a different framework now that maybe there needs to be an allocation into things that are private and alternative investments, which would include precious metals. And I've given a lot of interviews talking about that. Hey, people should think about having a maybe initiate a position of low single digits if you've never gotten into that. And if you're going to own it for purposes of investment, this is different than owning it for purposes of owning jewelry, for example, to wear that it's more efficient to maybe do that inside of an IRA because you're viewing this as an investment holding, maybe some sort of digital, digital asset currency, and then just something private because private markets today don't just represent non correlated things to the stock market. They actually also represent the versions of small cap and micro cap stocks that you could purchase 20 years ago that are not publicly available today because the Amazon of tomorrow is not currently trading on the Russell 3000 index today because they own go public. They have private capital to stay private.

57:47 - 58:05

Tarek: Right. And, and I think that's when I, when I was mentioning Uber, all of the, the biggest companies that do come to market, it seems like they're coming to market as $10 billion companies or $50 billion companies right out of the gate. So so much of the return is already baked into that asset by the time that it hits, hits the market.

58:06 - 58:06

Henry: Right.

58:06 - 58:07

Tarek: So it's, it's, it's a real challenge.

58:07 - 58:12

Henry: You got these companies, they date you, they're already in the S & P 500 by market cap size.

58:12 - 58:24

Tarek: So it's a, you don't get to grow with the company. Very few, a very small sub segment of investors get to enjoy all of that growth. And that's the Sequoias and you know, the big VCs and Silicon Valley.

58:25 - 58:50

Henry: And the limited partners who go into them, because remember a lot of people use our IRAs to become a limited partner in these venture funds. So yes, you're talking about the partners on Sequoia, the equity partners of a venture firm. But but those people also raise capital in the form of limited partners and limited partners. Those are private investments and they, we have a lot of IRA holders who do limited partner investments into structured venture and private equity funds.

58:50 - 58:53

Tarek: So the website is rocketdollar.com.

58:53 - 58:53

Henry: Yes.

58:54 - 59:02

Tarek: And for people who are looking for more information, they can, they can just go there, sign up, talk to someone. What is the process?

59:02 - 59:40

Henry: Yeah. So yeah, rocketdollar.com. There's a, there's a pretty expensive knowledge base database. There's lots of questions you can get answered. As a matter of fact, when you go to the site, one of the things you can sign up for is actually like a little online seven part course of just over a understanding self-directed IRAs or private investments in IRAs. But also there's a, there's a phone number too. So we have a one eight, eight, eight number. So it's one eight, eight, eight rocket D. And we answer that phone during business hours, central time, because we're a Texas based company. We roll up to a West coast based parent, but, but we answer that phone and we can answer those questions for people on that one, eight, eight rocket D.

59:40 - 59:47

Tarek: And you say, so you roll up to a, a parent. So you had another exit. It seems like with, with Rocket Dollar, you're still involved with Rocket Dollar.

59:47 - 59:48

Henry: Yeah.

59:48 - 59:50

Tarek: You merged with another firm.

59:50 - 1:00:29

Henry: We did. So we merged with the company that actually owns our trust platform. So we, to do IRAs, you have to work hand in hand with a custodian company. So the owners of our custodian and Rocket Dollar joined forces with them. So now we operate under a parent company brand called retired.com. So a lot of the stuff I've been doing, just sharing thought leadership thoughts on precious metals prices or retirement trends and so forth have been under that retired.com name, but, but I'm still fully involved in running the Rocket Dollar division of it, which is a alternatives capable IRA. So you can go to either one. I don't want to lead you back to rock.

1:00:29 - 1:01:02

Tarek: Sure. But, uh, and so what, what opinions do you have as we kind of wrap up this interview? What is your view on the market? So there's so much happening. It seems like there, there, there are a global brush fire wars. There's talk of tariffs. There's a lot of questions about the strength of the U S dollar, the polarity in the world with China and Russia, the U S I mean, it's just like countless number of topics that are affecting, um, you know, people's fear and, and concerns about what's going to happen with equities. What, what view do you have?

1:01:03 - 1:02:54

Henry: I mean, again, I'm going to, I'm maybe a long-term optimist on the markets. Uh, but short-term pessimists. So like this stuff has been moving. I mean, the funny thing for me is that I have a lot of friends who don't pay too much attention to their accounts on the market. And then I have people who watch friends who watch news all day long. And those people that actually haven't paid attention to their brokerage accounts, except for the quarterly statements on their IRAs and 401ks, actually have no idea that liberation day took their stock investments down by 10 to 15%, only to get back to exactly where they were last Friday, as we sit here today. So to them, nothing's actually happened, but in the short term, the people that are clued to that news have seen a lot of turmoil, but I would argue that you might be able to interchange the names of the political figures, the names of the countries and just keep the rest of the headline the same. And it's probably no different than the same ones that came out in the seventies, the eighties, the nineties, the 2000s, 2010s in the 1950s and the 1960s. I'll go ahead and throw that in there. So I think that the only way you can win is to be a continual investor. The one thing I might shift is that since now just public market securities represent a subset of the overall investable marketplace. I think that the investor of today just needs to expand what they can do with that money. And right now those products are available. I would just argue that what we're trying to solve at Rocket Dollar is to make the capital that sits inside of these captive retirement accounts, which encompass 16 to $17 trillion. You add 401ks, we're talking another like six, seven, $8 trillion on top of that. It's difficult to get that money into investments that aren't that small subset of public equities. And that's the problem we're trying to solve in the marketplace. Just make it easier to let people take existing monies that they already have to go into investments that typically were only accessible by a very small subset of investors.

1:02:55 - 1:03:09

Tarek: What you've done is so impressive. Love the website, love the company. I think you are just a great role model for any entrepreneur who is hungry and wants to start a company. Thanks for joining us.

1:03:09 - 1:03:34

Henry: Thank you very much. And you know, it's probably not going to work out on the first few businesses. You mentioned Uber a couple of times. I mean, I remember reading that Travis Kalanick had started somewhere in the range of 10 to 15 companies. And he's very public with about saying that eight to 11 of them failed. One of them was a modest success for a couple hundred million dollars. And then that gave him the guts, freedom, and probably swagger and confidence to start what became Uber.

1:03:34 - 1:03:55

Tarek: The only way to be a successful entrepreneur is to get comfortable with failure. You have to be able to take, you know, shots at the, at the dar board and, and you know, some are going to stick, some are going to be bad, bad shots, but that's okay. That's, it's all part of a learning, um, a library of learning that you can take to your next venture.

1:03:55 - 1:04:16

Henry: Exactly. You have to do that. So you have to be willing to, to, you have to be willing to take the losses and learn from them to actually build the big successes. Right? So, I mean, at the end of the day, Michael Jordan has probably a couple dozen to a few dozen game winning shots over the course of his career. He's made thousands of shots overall, but he's missed thousands of shots as well.

1:04:16 - 1:04:16

Tarek: That's right.

1:04:17 - 1:04:19

Henry: I mean, people only remember maybe the 28 times he had a game winner.

1:04:19 - 1:04:21

Tarek: You only make the shots you take, right?

1:04:21 - 1:04:32

Henry: But those 28 shots are not just those 28. They're, they're basically built on the foundation of the overall 10,000 shots he took in a career of which he missed 50%.

1:04:32 - 1:04:36

Tarek: So, so what's the message there? Go for it.

1:04:36 - 1:04:45

Henry: I mean, the message is to try because probably you don't want to be sit there, sit there at 80 and just regret that you didn't try anything and just did the same thing for, for the long haul.

1:04:46 - 1:04:47

Tarek: Great way to close.

1:04:47 - 1:04:48

Henry: Yeah. Thanks.

1:04:48 - 1:04:48

Tarek: Thank you.