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- [00:00]
Host/Advertiser
The number one thing I hear from founders isn't AI, it's hiring A players are rare and expensive. That's why Smart founders and CEOs are using near to hire top tier offshore talent in Latin America. Over 700 companies like Function, Health, Expensify and Deal use NEAR to build their teams and save hundreds of thousands in overhead. From senior engineers to heads of accounting to growth marketers. If it can be done remotely, near can find you the right person. You'll save up to 70% compared to US hires, but the real win is the quality. These aren't freelancers. They're loyal long term team members who actually care about your business. Near moves fast. You'll get resumes in three days and fill most roles in under three weeks. And you don't pay a dime until you make a hire. One of near's founders is a Hampton member and plenty of others already use them. So if you're ready to hire the best talent in Latin America, you go to hirewithnear.com moneywise. That's hirewith n e a r.com moneywise to get 5% off your first hire.
- [01:10]
Jackie Lamport
Building a business and selling it for tens of millions of dollars is one way to make a lot of money. But it's not the only way. And our founders have actually made some good money on the side as well, which is what this list is about. Like somebody who wrote a $10,000 seemingly forget a check and it turned into 1.2 million. A guy who was currently worth about $100 million but actually made his first million from his basement before he'd actually even started his business. And another guy who 3x his wealth overnight without actually investing in anything. And this list isn't going to be about the safe stuff like index funds and bonds, which I know Sampar touts a lot because I mean it should be an important part of your investment strategy. This is the more fun stuff, the riskier stuff that have actually paid off for a lot of our founders. With specific examples. This is money wise, a show for founders who have already seen some success and are in the stage of figuring out what to do with it. And I'm Jackie Lamport, the producer and sometimes host who happens to have stumped a lot of you in the comments. When it comes to my age and gender, which it's very funny to me, so keep guessing. Also, I'm a little bit sick. But we'll go on. So. So let's do that. Let's go on. We'll start with one of My favorites. The best $10,000 Jacqueline Johnson has ever spent.
- [02:24]
Jacqueline Johnson
My first ever angel investment was into away luggage. It was the friends and family round. I wrote like a $10,000, I think check and did not have $10,000, nor was I an accredited investor at the time. I was like, just like, I remember my mom being like, what is this check? And I was like, just let it go. You know, I'm helping a friend out and like, she helped me out and like, whatever. And cut to, I don't even know how many years later, maybe like seven, eight years later, you know, was able to be bought out of that investment for close to $1.2 million.
- [02:52]
Jackie Lamport
That makes this first item on the list angel investing. And if you're thinking, hey, yeah, but that's not a great example because she kind of just got lucky there. I mean, it is kind of how it works. But also, you're right. And she does acknowledge that.
- [03:04]
Jacqueline Johnson
Obviously I was like, angel investing is the best. I was like, that is not normal. I'm like, no, I know, but like, here's what I'll say. I think the beauty of angel investing is. So I have 25 different companies now in my portfolio and I think of it as my own personal venture fund in a lot of ways, right? Like where I can kind of think about one, like, it's always founder first for me to how do I diversify? Three, how do I help sell this company? Like, I've been through it now a few different times. I've also seen companies go through it. It's not formulaic in a way, but it is. There is like a way to kind of get there, right? And I think being able to support and help other companies do that now feels exciting and rewarding. Of the 25, I think three have exited successfully where I've made a return, obviously none at the level of away. And maybe two have like, you know, completely gone under and all the rest are kind of still in play.
- [03:54]
Jackie Lamport
There are a few downsides to angel investing. One, it could be a really long time before you actually see any return. Two, you might not see any return at all because it is quite risky. And three, it can be kind of boring if you're just sitting around and writing checks. The people who we've talked to who have actually had the best experience with it are the people who are in it for more than just the money. For instance, in Jacqueline's case, she is primarily supporting women owned businesses and helping them grow because, I mean, it's kind of her thing. Vinay Hormath has a similar angle on it.
- [04:23]
Andrew Wilkinson
Like 5% of my net worth is like active investments that I make, like angel investments. And that's like the most fun to me. That's like, okay, I get to invest in these founders. They hit me up, they need help, like on like 11pm calls with like 2 founders who are like fighting about something. It's like actually being involved as like an angel who is like an operator is really fun.
- [04:44]
Jackie Lamport
So angel investing can be a nice way to kind of stay in the game without being the CEO or the full owner of something. Also to be a part of the success journey for some up and coming founders, which is rewarding. You might also be financially rewarded or not at all. But if you do want to throw your hat in the ring for a $10,000 check to turn into $1.2 million or something like that, here are some tips for angel investing based on the strategies that our founders have shared with us. First, cap the percentage allocation in your portfolio and stick to it. Don't make exceptions. Second, see it as kind of play money, not a sure thing or retirement plan. Because yeah, it may or may not work out and if it does, that's great. If it doesn't, yeah, you don't want it to not work out if you're expecting it to. And third, stick to the spaces and the founders and the models that you already know or understand. Also, Oren Hoffman is a really big angel guy and he actually came on, talked all about that and shared all of his personal finances. I will link that episode in the description of this video if you're curious. Next up, let's talk about a beach house. What's interesting about this one is that unlike a lot of real estate investments, it was immediately profitable and it resulted in quite a big payout relatively quickly. This one comes from Ann Maloom.
- [05:55]
Ann Maloom
On the second deal that I did, which I took 9 million, I bought a house in the Dominican Republic like two months after for 3.6 million. And then I sold that 18 months later to Albert Pujols for 5.6 million. And I rented that out along the way. So it was, it was a cash flowing property.
- [06:16]
Jackie Lamport
So $3.6 million in, $5.6 million out, that's $2 million profit, not including the cash flow along the way in just around 18 months, which is pretty substantial. But this is not Anne Marloon's only real estate investment. Far from it. In fact, it's actually a pretty big part of her Strategy.
- [06:32]
Ann Maloom
I've done 20 to 22% in real estate.
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Sponsor Representative
Is that real estate? Cash flowing real estate?
- [06:38]
Ann Maloom
Yeah. It's not cash flowing real estate. So I'll tell you again, and I've done really well in real estate, and I've done cash flow real estate in the past. But for where we are, like, we have a place in Miami, our primary house. This is public, and I have no problem talking about, we bought this house for $12 million. We got a crazy deal on it. It was in probate, fully furnished. Two million bucks. We use it all the time when we go play volleyball. And I have a place in New York that I bought back in 2018, which we also use. And I'm there for work, you know, quite often. And then I bought my dad a house back in 2015. He still lives there. That's pretty much paid off. And then I bought a house that my brother and his wife and the kids live in back in Bismarck. And it's. That's sort of part of my gifting, is that real estate. And then I just put down a deposit on a $14 million condo in sunny Isles called the St. Regis. And that is an investment. I will sell that over. It's not. It doesn't finish till 2029. At some point over from now until then, before the 50% of the payment is due, I will sell that property.
- [07:42]
Sponsor Representative
And so does that mean something like $25 million in real estate?
- [07:47]
Ann Maloom
Well, yes, it is. I have about 20, 22 million dollars in real estate.
- [07:54]
Sponsor Representative
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- [09:05]
Jackie Lamport
We've actually had a bunch of founders on who have talked about real estate not just as a long term asset strategy, but also as a cash flow strategy. Jeff was one of those people.
- [09:15]
Guest Founder
The real estate that I own today is cash flowing real estate that brings in about 2 million a year, 2 1/2 million a year with the three main projects I have.
- [09:23]
Jackie Lamport
And obviously not everything has to be as sexy as a beach house in the Dominican. Take it from Rajeev Ganesha.
- [09:28]
Guest Founder
One of the great things, you know, I bought a mobile home park, what is it, 12, 13 years ago. That's done really well. That's a great investment, by the way. So that's done quite well.
- [09:38]
Jackie Lamport
The downside to real estate is that it is illiquid. So if you do need the money overnight, yeah, obviously that's going to be difficult also, as much as it is a passive thing, it also also does require active participation. Things break, tenants leave, property managers can make mistakes or also leave. And so, yeah, you will need to put some effort into that. However, as a wealth preservation strategy and as a passive income strategy, it's kind of hard to beat, which is why it's so popular and why it's on this list. And now for an entry that you guys have every right to argue with me in the comments about, because this is about the guy 3x his wealth without actually technically investing in anything. He just moved.
- [10:18]
Guest Founder
If I stay in Colombia, I can jump ahead in life financially, lifestyle wise, like 10 years.
- [10:26]
Jackie Lamport
Rob Hoffman grew up in cold suburban Canada, and privilege wise, it's a great place to come from and a great place to live. However, as someone who grew up only an hour away from him and knows his town quite well, I can confirm that if it's not the lifestyle for you, it can be boring. It can be really boring. But instead of moving to the city, which would be Toronto in this case, or even to an American hub like Austin or New York, he decided to move somewhere that was exciting and would also give him some financial Runway Medellin, Colombia at the time that we interviewed him, his net worth was about 1 million USD, which with conversion turned it into about 3.2. But this isn't just about a one time conversion. He's also lowering his housing costs, his day to day expenses, he's keeping his earning power and he, he's letting that gap compound. He says it's geo arbitrage. Listen, there's a lot to say about this one and we did say a lot actually in the episode that we had with him, which I will also link to in the description of this video. But there's a couple things that I just want to say really quick. When he first got there, he had $10,000 Canadian in savings. And the goal was to make that last for an entire year so that he could give his business a shot. Which also means that he was spending as little as possible, which means that he was living in an apartment that was $50 a month in rent in a not great neighborhood. And he had some interesting stories. But the most important is that his goal is not to exploit the community or the currency. He genuinely loves it and so he learned the language, he ingrained himself in the culture, he uses his money to give back to the community and he plans to stay. So yeah, this isn't about just taking advantage of a currency and then pulling out once you've had the advantage. But for founders, especially those who are post exit or who are running businesses that can be run remotely, this is a cool lever because you can do what Rob describes as jumping forward financially, lifestyle wise. Ten years, you can have your Runway go further. So if you have money that you want to make last. Yep, there you go. And also you can free up cash to put into safer investments. Speaking of safer investments, love it or hate it, this next entry has been a pretty successful one for a lot of our founders. So let's talk about that founder who was worth a hundred million, but actually made his first million. Roman's basement, long before he had started his business. Also, he actually didn't realize that he had made his first million when he did it. You can probably see where this one is going, Bitcoin. However, this wasn't somebody who just invested and put it in his wallet or something. This is a guy who got in very early.
- [12:54]
Guest Founder
I've always been what I tell people as subject matter enthusiast. And so in the libertarian subreddit early days, like 2013, I started mining bitcoin and that's actually where I made my first million.
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Sponsor Representative
Didn't you forget that you had done that?
- [13:09]
Guest Founder
I did, yeah. And so there's a lot of people that will claim to, oh, I used to do that and I lost the hard drives or whatever. Well, I actually have about 300 hard drives that I just. I never throw anything away. And 20 years of creating media and all these other different things, I just completely forgot where it was at. So I hired a company to catalog one of my company's media storage and everything onto a server. And I was like, hey, could you do this for me personally? And do it chronologically by year? Because I knew approximately when I was mining and they did and I didn't tell them exactly what I was looking for. And I was able to find it based off of that.
- [13:49]
Sponsor Representative
And at this point it's. We're in March, I think it's like, I don't pay attention to bitcoin. It's an all time high though.
- [13:55]
Guest Founder
It is.
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Sponsor Representative
Surely you've done well, right?
- [13:58]
Guest Founder
Yeah, yeah.
- [13:59]
Jackie Lamport
So, yes, sorry to say, but you can't really repeat that one. However, crypto still is a part of a lot of the portfolios that we've broken down on this show. The thing is though, when people talk about it is it's either just a little or they refer to it as a bit of a gamble. In fact, Chris Cook literally said it's like playing at the casino. And Rob Walling's problem with it is, well, that he made too much.
- [14:21]
Host/Advertiser
I tell you what, there's more in
- [14:22]
Jackie Lamport
crypto than I would like because it went up so much.
- [14:24]
Host/Advertiser
It's one of those weird things where it's like, I'm going to put 3%
- [14:26]
Jackie Lamport
of my net worth and then you
- [14:27]
Host/Advertiser
look and you're like, oh, 30% of
- [14:28]
Jackie Lamport
my net worth is now in this super volatile thing.
- [14:31]
Guest Founder
Right.
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Host/Advertiser
So I've obviously been selling a bit
- [14:33]
Jackie Lamport
of that over the years. Oh, and the other thing that I've noticed about the people on the show who have been successful with crypto or happy with it, they sold it. And that's not to say that crypto is a dead opportunity. It's more just to say that you got to know when to get out. Because the point of it is to make money and it is a gamble. So, yeah, take it all in all, it can be a crazy return, but it's also a bit of a ride and it can be pretty unpredictable. So have fun and be safe and have fun.
- [15:02]
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- [16:35]
Jackie Lamport
This next item is kind of ironic because we're talking about founders who have sold their successful businesses because this next item is buying successful businesses. This is kind of Andrew Wilkinson's whole thing.
- [16:45]
Andrew Wilkinson
I decided that I wanted to start investing and I basically copied Warren Buffett and started buying small tech companies and just growing them over time and holding them. I remember in 2021, we had grown a ton and the business was doing tens of millions of dollars of profit. And we also took a business public. And I remember looking in my trading account and seeing my stock portfolio and suddenly this previously private business, which I owned, but I didn't really know what it was worth, was worth hundreds of millions of dollars.
- [17:25]
Jackie Lamport
Oh, and whether or not you actually plan for this strategy, you might end up doing it anyway. Like Alex Hormozi.
- [17:31]
Guest Founder
Then all I thought was like, well, shoot, now I got to take this cash and go buy that amount of cash flow.
- [17:35]
Jackie Lamport
This can also just be your entire business strategy. Like Corey Mitchell.
- [17:39]
Corey Mitchell
We were buying little, little businesses originally in cash. You know, with whatever cash we we made that year, we reinvested and we bought a demolition business in Iowa. It was a $3 million revenue business. We added environmental service lines to it, gave that team confidence, we gave them a little bit of a balance sheet and that business grew to 24 million organically over the next three years.
- [18:03]
Jackie Lamport
But of course this is another one where you do need to know what you're doing. So here are some tips based on our guests experiences, starting with something that you might have noticed. Andrew Wilkinson is a tech guy and he buys tech businesses. Corey Mitchell is a blue collar services guy and he buy blue collar services businesses. So I don't know if you're sensing a pattern here. Yeah, buy what you know other than that by simple profitable businesses where the revenue margins, customers, that kind of stuff is already there to have a plan for the business before going into it. So if, yeah, if you want to grow it or continue that cash flow, just think about it before you actually pay for it. And lastly, don't think of it as a passive thing. This is going to be an active investment now because yeah, you have stakes so you're going to act like it. So yeah, number five is buying cash flowing businesses so that you don't have to start one from scratch to get there again. I swear you're the gold. I've been running like I woke up and won the top with that list wrapped. Let's point out a few recurring themes here. First, these are all sized and concentrated appropriately so they're big enough where you could see a nice return potentially. But also if it doesn't work out well, it's not going to be the end of the world because yeah, you don't want that to be the case. Second, they're all utilizing pre existing skill sets so you're not jumping into something new, expecting it to just kind of happen to work that you understand what's going on. Yeah, do things that you already think you can do. And third, they're built on top of safer things which we didn't really get into here, but every single person that we've spoken to has that safe bed of index funds, ETFs, those like boring things where their money is safe. Yeah, that's important. And if you do want to get an in depth look at some of those portfolios that I mentioned, I've linked all of the episodes that we talked about in the show in the show notes, so check that out. Also, this podcast is made for the Hampton community. As you probably have heard, it's a community for high net worth founders and a lot of the people that we speak to on the show are in that community. So if you're looking for some more advice or just to connect with other founders on stuff to do with your business or your personal life or whatever, your founder doing at least $3 million in revenue, you should check that out@joinhampton.com Also, if you want a podcast like this one, which is pretty cool, I must say, you can check out Lowerstreak Co, because that's where I work and we made this. So if you want one, go check it out. I'm Jackie Lamport. This is money wise. And I'll see you.
- [20:36]
Jacqueline Johnson
See you soon.