Lessons to Learn from a $28B Real Estate Empire

What can a retired real estate mogul with $28 billion in AUM teach us about building enduring wealth, navigating downturns, and staying relevant in a digital world?
In this episode of REady2Scale, we sit down with John S. Pennington, Jr., co-founder of Bridge Investment Group, who led the firm from its inception through an IPO and managed over 100 funds before retiring in 2021. He shares the hard-earned lessons of building a real estate empire, the value of long-term thinking, and how digital assets like Bitcoin could reshape the future of alternative investments. With a candid mix of storytelling and strategic insight, John breaks down the realities of fund structuring, economic cycles, succession planning, and risk.
Key Takeaways:
- The fund structure that allowed Bridge to scale and why general partnerships offer more control than public corporations.
- Why 2008 was the best buying opportunity of his lifetime and how they positioned themselves early to take advantage.
- How John evaluates risk today and why experienced managers with personal capital in the fund matter.
- A comparison of 2025's macro landscape to past crisis years, and what it might signal for investors.
- A primer on tokenization, Eurodollars, and the long-term challenge digital assets pose to traditional finance.
- Succession planning insights from someone who transitioned out with intention and impact.
- How personal discipline, family focus, and resisting lifestyle inflation created long-term security.
- Why he still keeps 90% of his wealth in real estate-backed assets and the balance he strikes with Bitcoin and gold.
- This conversation is a masterclass in how real estate, economics, and disciplined investing intersect and what it really takes to build something that lasts.
Guest Info
John S. Pennington, Jr.
Co-Founder, Bridge Investment Group (Retired)
Author of Dollars, Gold & Bitcoin: A Guide to Value in a Changing World
LinkedIn: John S. Pennington, Jr.
Website: www.johnspenningtonjr.com
Timestamps
00:00 Introduction and Guest Background
01:37 John's Journey and Key Lessons
11:48 Navigating Financial Crises and Future Outlook
21:55 The Eurodollar System and Global Currency Dynamics
22:23 Balancing Real Estate and Digital Assets
24:47 Succession Planning and Retirement Insights
Are you REady2Scale Your Multifamily Investments?
Learn more about growing your wealth, strengthening your portfolio, and scaling to the next level at www.bluelake-capital.com.
Credits
Producer: Blue Lake Capital
Strategist: Syed Mahmood
Editor: Emma Walker
Opening music: Pomplamoose
*𝘉𝘭𝘶𝘦 𝘓𝘢𝘬𝘦 𝘊𝘢𝘱𝘪𝘵𝘢𝘭 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘰𝘱𝘱𝘰𝘳𝘵𝘶𝘯𝘪𝘵𝘪𝘦𝘴 𝘢𝘳𝘦 𝘰𝘱𝘦𝘯 𝘵𝘰 𝘢𝘤𝘤𝘳𝘦𝘥𝘪𝘵𝘦𝘥 𝘪𝘯𝘷𝘦𝘴𝘵𝘰𝘳𝘴 𝘰𝘯𝘭𝘺. 𝘛𝘩𝘪𝘴 𝘪𝘴 𝘯𝘰𝘵 𝘢𝘯 𝘰𝘧𝘧𝘦𝘳𝘪𝘯𝘨 𝘵𝘰 𝘴𝘦𝘭𝘭 𝘢 𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺 𝘰𝘳 𝘢 𝘴𝘰𝘭𝘪𝘤𝘪𝘵𝘢𝘵𝘪𝘰𝘯 𝘵𝘰 𝘴𝘦𝘭𝘭 𝘢 𝘴𝘦𝘤𝘶𝘳𝘪𝘵𝘺. 𝘗𝘭𝘦𝘢𝘴𝘦 𝘤𝘰𝘯𝘴𝘶𝘭𝘵 𝘸𝘪𝘵𝘩 𝘺𝘰𝘶𝘳 𝘊𝘗𝘈, 𝘢𝘵𝘵𝘰𝘳𝘯𝘦𝘺, 𝘢𝘯𝘥/𝘰𝘳 𝘱𝘳𝘰𝘧𝘦𝘴𝘴𝘪𝘰𝘯𝘢𝘭 𝘧𝘪𝘯𝘢𝘯𝘤𝘪𝘢𝘭 𝘢𝘥𝘷𝘪𝘴𝘰𝘳 𝘳𝘦𝘨𝘢𝘳𝘥𝘪𝘯𝘨 𝘵𝘩𝘦 𝘴𝘶𝘪𝘵𝘢𝘣𝘪𝘭𝘪𝘵𝘺 𝘰𝘧 𝘢𝘯 𝘪𝘯𝘷𝘦𝘴𝘵𝘮𝘦𝘯𝘵 𝘣𝘺 𝘺𝘰𝘶.
Episode Transcript:
So a lot of times you hear the saying that real estate investing is not rocket science, and it's true, it's not. But every once in a while, thanks to this show, I'm fortunate to get to talk to some people that have been incredibly successful. So we have a treat for you today. Let's get ready to scale out.
Hey guys. My name is Jeanette Friedrich, director of Investor Relations here at Blue Lake Capital. Joining me today is John S. Pennington, Jr. Who retired as the co-founder of Bridge Investment Group with over 114 funds valued at the time at $28 billion in asset under management back in 2021 a month.
Prior to that, I. John was part of taking the company public on the New York Stock Exchange. He's had an incredible career starting back in 1989 when he co-founded his very first company that was focused on exporting. And then through 20 through 2004. All the way through to essentially 2009. He co-founded multiple Bridge Loan Capital funds that ultimately culminated to become Bridge Investment Group in 2009.
And then again, he got to retire in 2021. And in 2023 he also wrote a book. Called Dollars, gold and Bitcoin. That's available today on Amazon and audible.com. John has a Bachelor's of Science in Economics from the University of Utah, and he's joining us today from Sandy, Utah. So John, welcome to the show.
Thanks, Jeannette. Thanks for having me. I'm fun to be here. Yeah.
Oh, I'm thrilled to talk to you. First of all, John, do you wanna just share with us kind of your story about how it is that you have arrived here? It's a huge goal for a lot of people.
Yeah. Just a quick, a quick summary.
I just always knew I couldn't make it in corporate America. I couldn't, I didn't have that personality, so I always knew that I had to start my own stuff and then let those things grow and grow. So I started 14 businesses in my lifetime. Three has, ma three have made a lot of money, and obviously my last one made a lot of money, and three, I lost money on, and the rest of 'em in the middle.
They all, they all made some good money and those are the hardest ones to do because you don't know, should I go one more year and make it really good? The ones that are losing money easy. Just cut 'em off. But the ones in the middle. So I just knew that I had to keep going and people ask me if I'd go back and change anything, and I would say no because the ones that failed, I.
I learned, if I wouldn't have had those that failed when I got to my big deals, I would've probably made those mistakes again. So I made the mistakes in these other ones. What's really hard to go through when you're making the mistakes and it's really hard to see the big picture, but looking back on it.
I'm glad I made those mistakes and pushed through them to get to where we eventually got in the real estate funds. Like I said, we had 114 limited partnerships when I retired. And I was a signer on over 1200 bank accounts at 19 different banks. We were managing about $28 billion asset, our management.
And I always, when I give these presentations, I always, you know. Because people overuse the, they misuse the word billion all the time. They'll go, John, I was just outside and I saw a, there's a big flock of birds. There must have been a billion flock of birds, billion birds. And I go, no, there hasn't.
'cause I've done the math look a billion, if I give you a dollar a second and I never sleep and I never go to the bathroom, I never, I just keep 1, 2, 3, a billion seconds is 31.7 years. Wow. For you to spend a billion dollars a dollar a second, it's gonna take you 31.7 years to spend 1 billion. And I remember when we hit 1 billion as in management, I did the math and I go, and that can't be right.
I kept doing it and doing it. So when I say, $28 billion in our management when I retired. And now the company, I've been retired for three and a half years-ish, and since we went to New York Stock Exchange it's a lot easier to raise capital. We're 49 billion assets in our management today in real estate, all across basic verticals.
We do large apartments. Multifamily. We do large industrial, large office buildings, large senior assisted, and then we have opportunity zone funds, and then we have also real estate debt funds that we do mortgages and we buy mortgage pools and stuff like that. But it's all boring real estate. It's all, I call it boring real estate.
It's long term, long, long term real estate that some people just pass up because it's not as exciting. It doesn't go up and down the volatility and stuff. But in, in the long run, it's just. It, it works. People, some people like just consistency and so that's when we started and my first fund was in 2004, but I think before the show started, you asked me about a pivotal point, yeah. I wanted
to know. Yeah. And I've been
thinking about that since you asked me right before the show. I'm going, was a pivot. Yeah. I'm thinking.
It was
1999.
Yeah. Just let me, okay,
sorry. Sorry, I don't wanna Jo, jump ahead. Go ahead.
No. That's okay. But I just wanna, I wanna loop the listeners in.
So yeah, what I had teased the question with before we started recording was if there was any type of pivotal dill or moment where you feel like you learned more about navigating risk from that experience than you ever did in a textbook and what, how you were able to learn from that lesson and then, put it into a repeatable playbook essentially.
Yeah it wasn't a deal. It was, I was wa 1999, I was in between businesses trying to figure out where I'm gonna go in life and I'd sold my one business right outta college. Not sold it, but we closed it down. It was a really good run for about nine years in exporting. And I watched this news reporter on television vilify fund managers in New York.
They were making all kinds of money and they were paying really small taxes. And this, she was like, vilifying them. And I was like I wanna be one of those guys, right? I want, I'm like, we don't wanna get, I wanna learn how that, and there were, back then, there's no textbooks on how to be a fund manager.
But I
said, I want to be one of those. And it took me five years. I didn't launch my first fund until 2004. And so during those five years, I got my series seven license. I sold mortgages. I during, eventually got a series 65 license and I read ppms and LPAs and ppms and LPAs, private placement memorandums.
And
limited partnership agreements over and over again. And finally in 2004, we launched our first fund just me and another guy, and it was called Bridge Loan Capital Fund, which we were doing bridge loans. Loans one to six months. And it's basically you have a builder. He has enough money to build 10 houses, but he doesn't.
He builds 14. I don't know why they do this, but they do. And then some point they get in a financial crunch where they're gonna miss payroll two weeks from now and they need a loan to get through payroll. And so they would come to us and they need a quick loan and for 90 days or something or and we would say do you have a piece of real estate?
And so we would. Put a first lien of trust on that real estate. Give them a loan and they could then go and. Pay their payroll and then eventually sell some property and then pay us back off the real estate. They give us the first deal trust or someone who makes widgets for Walmart or Costco and they have a net 90, same thing.
They're just behind. They need to hit payroll and this guy that runs this widget company. He has a piece of real estate somewhere and we put a loan on that for four months and we give them the money and they meet payroll, and then they finally get paid from their big box retailer, and then they pay us off.
So that's how we first started in the first fund. And then a few years later we launched the second fund and had added some more partners in real estate. And then in 2009 or oh 8 0 9, we a added a we joined with another company that, that did property management had been doing it for years, and that kind of just took off.
But that was 1999 was when I said I, I'm, and I didn't tell anybody that I wanted to be a real estate fund manager. I didn't tell 'em. They, I think they would've laughed. I just kept it to myself. But everything I did like my series seven, my series 65 and selling mortgages and I was just learning the whole thing so that when I launched, I would have the confidence to really, really do it right.
Now back to risk. And it's a good question. I really like the question about when I figured out how to mitigate risk, a fund model. Let me, lemme say this everyone knows Steve Jobs of Apple. He took his company public in an ink structure. There's incorporation, they have shareholders, they have the board of directors, they have presidents, and every year the shareholders get together and vote on who runs the company.
That wasn't gonna work for me because I figured I was gonna make a huge company and I didn't want one day. The shareholders voting me out of my own company.
Right?
And then when I found out about funds, a general partnership, a limited partnership or limited partners. Limited partners can have billions of dollars here in the fund and we can be investing and they cannot vote the.
General partner out unless the general partner commits fraud and I'm never gonna commit fraud, so I was safe. So you take Steve Schwartzman of Blackstone, they went public, but they went public in a general partner limited partnership structure.
So Steve.
Jobs got voted out of his own company and Steve Schwartzman can never be voted out.
And so when I found out about funds, I thought what a great structure to build and bring in more talent. 'cause I knew, me and my first partner, we always joked each other. We said, we want to big build a big, huge real estate company. And we just looked at Gerald the whole time. You and me we're not smart enough to run a big company.
We need to premium. We need to bring in way better talent than us. And we were able to do that. We brought in some incredible partners over time that were specialists in different things and we focused, we had these verticals of multifamily and industrial and office buildings and seniors living and lending on real estate, and they're just absolutely brilliant partners of mine, mine that took our company to heights that I never even imagined.
Yeah.
Fascinating. So my takeaway from that is, the best way to navigate risk is to really bring in very skilled talent that has a very very sharp focus and discipline in kind of their particular area in order to best navigate risk. Is that basically a good way to summarize that? I love,
I love it.
And so to the investor, I know your audience are mostly passive investors to the investor, if you go into a new fund and this fund manager has two or three years experience in that asset class, okay, that's pretty good. But if that, that you have a group of fund manager, let's say you have three or four fund managers that have 15 to 20 years in that asset class.
They've gone the ups and downs of, they know all the tricks, right? They know all the all the things that can go bad. And if those fund managers also are limited partners. Right alongside the investors' money.
So they have 15, 20 years, they're investing their personal money into the fund, and they're asking you to invest.
Your personal money into the fund right alongside their money at the same risk. So that's one way. There's lots of ways to mitigate risk, but that's one way. 'cause I've met fund managers that run funds out of New York. They have none of their own money in their own fund. I.
Yeah, huge. And I
just can't, I don't understand why, how they even raised capital.
Yeah. Agreed. Agreed. I always consider that a red flag. Now, you talked about downturns and, earlier you mentioned, actually starting a fund in oh eight, right? So we're talking in the middle of the great financial crisis, yeah. So how did you steer bridge through, the different parts of the cycles, booms and bust?
Did you use any type of counterintuitive strategy? How did you lead your company through those hard times? Rather we're talking the great financial crisis. Yeah. Even COVID, some people thought COVID was gonna be a huge thing. Yeah,
yeah.
I I'll go back to my partners.
I, I had brilliant partners and so by 2008. We had two lending funds. We were lending on real estate. Okay. Mainly in the Western United States, just the western states. And I we brought in a ploy that eventually became partner. He was brilliant. And he forecasted this is, middle 2007 'cause we.
We actually saw the banks all freeze up in August, 2007.
That's when everything froze. Yeah. Didn't, everything didn't hit the fan until the fall of 2008. And he told us, we, we sat down with him in his office and he was like, we're in really trouble. And I said, we, knowing the country is in real trouble, he had four, he worked for a big firm out of salton brothers and he forecasted the, I think 1998 crash of the. Asian market. He forecasted like nine months before. Wow. And so we said, what do we have to do to get through this? And he said, we've gotta stop lending. So we gotta pull, start pulling our horns in and we gotta get ready to start buying properties in 2009, 10, and 11.
And so we got our PP, we started a third fund in 2008. Got their ppms and LPAs all going and ready, start starting to raise capital to start calling banks and buying property from them. They foreclosed on 'cause it's gonna be really cheap and it was already really cheap. It's gonna be even cheaper and.
During that time, right about December, we were about to raise our first capital. We were looking for a company in New York or LA or San Francisco that would, could manage the properties we're gonna buy. And lo and behold, we found a group right here in Salt Lake City right down the street from us and.
They were brilliant guys and they'd been doing it for years. The multi-family managing and buying and, but they were laying people off 'cause it was real estate and it was 2008. And we basically said, let's stop real estate. All you guys need is a really good fund to bring in great capital 'cause there's, 'cause it's the best time to buy.
And I actually had a few of my friends call me up, John, how you doing? I'm good. Why? Why? Why are you calling? We know you're in real estate. And we know this is a really bad time for real estate. It's 2008 and I just said, I was on the phone, I remember saying this, are you out of your mind?
It was the best time ever.
This is
2008. This is the best time to be in real estate. And they go, what are you talking about guys? This only comes around every 80 years.
You can't buy stuff this cheap ever. And so about at least three or four of those guys that called me. They eventually became my investors. They were calling to feel sorry for me. And back to your, back to risk and stuff, 2009, we were just telling everyone, look you're thinking wrong. You're thinking, you're not thinking like an entrepreneur. You have to buy in 2009, 10, 11, 12. And so that's what we did. We launched that third fund with a new group of guys and their team, and they were brilliant.
And and that really took the company from, really low a or zero zero asset under management. To, in 2021, we had 28 billion assets in our management with, I think thousands of employees in 33 states. And we were able to go public on New York Stock Exchange. And so back to your question how do you guide it through?
You gotta have some vision. You gotta have entrepreneurialism. You gotta understand where you're at. At the time, and you need brilliant people around you, and we had brilliant partners. It was fantastic.
Interesting. And now, looking at the market today how much would you say you, how much correlation do you see between that time back in, let's say oh 8, 0 9, to where we are in the market today?
Because at least when it comes to multifamily, which is what we focus on here we haven't seen pricing this low in a decade.
Yeah, it's been a while. Yeah. Yeah. So I'll give you, I'll give you a kind of a macro thing. In 1971 when we went off the gold standard for the dollar.
If you keep going a little bit about every 10 years, you get these huge, something huge happens.
In 80, 88, 87, 88, the Soviet Union collapsed.
And we had a big fin. We had a big stock market crash. Okay. So that was opportunity in 19, 88 in 1999, 2000, we had the.com bubble and the crash in 2008, nine, we had the global financial crisis in 2000, 20, 19 and 20 we had the COVID. And so we're due for another, I think you're seeing inklings of that 10 year cycle kind of thing.
And and so I would say, with the increased the thing is with my economics degree, I talk about economics to my friends a lot. I love talking economics, but right now it's difficult to forecast because there are a few things are going on that has never gone on before.
A country has never been able to spend $1 trillion every a hundred days and keep doing it. No one's ever been able to do that. So when you put that much money into an economy, it's really hard to have a recession. There's just. A trillion every a hundred days boom. We don't, we never had Bitcoin before.
And so there there's some things, and we got AI now at cusp being at a lot of things and in the job market. So I. Forecasting based upon past charts and now forecasting. And everyone always says it's different this time, but I think a trillion dollars every a hundred days and ai and having cryptocurrencies, those things are different and they tend to not confused, that's not the right word, but have the economists of the world and forecasters of the world running probabilities.
They're all conflicted.
Yeah, people
say it's gonna go down. It's gonna go up. No, it's gonna go down, it's gonna go flat, gonna go whatever. And. And it used to be a better consensus years ago, but now I just see it's all over the place. Yeah,
yeah, of course. And then throw in, the tremendous amount of uncertainty with the current administration tariffs.
It's very difficult to be able to really forecast with confidence because it's so many variables can shift at any moment. And all of them have a different. Impact and interplay yeah. Within the economy. Yeah. And I'm glad you actually touched also on Bitcoin, because I wanted to talk about your book.
In your book, dollars, gold and Bitcoin, you're basically exploring three distinct stores of value, right? And so after you've spent, decades managing real estate investments and growing, bridge to the extent that you have, I'm just. Curious, what do you think now of tokenization and digital assets and how that's gonna reshape alternative investments?
Yeah the digital asset, digitizing in a Coinbase, let's say there's, some buildings behind you in LA over there, and if one of those buildings was digitized, rather than having a title and title, insurance, stuff like that, if it was digitized on a blockchain and there were a million coins on that building, and you could buy 1000000th of that.
For, I don't know how much money, let's say a dollar, let's say it was a million dollar building, and you could buy a dollar, and that was so easy to distribute profits every month just by a push of a button, a CH. That efficiency seems like you're going to eventually get it because people tend to, in technology, tend to move to efficiency now in the same manner.
People who control power, don't like to give up power, right? So the stock exchanges, New York Stock Exchange, nasdaq, they have power. They make fees as you go, as you transfer to fees, and they make a lot of money off that, and they have a power. So giving up that to a digital building behind you is gonna be a fight.
And so it's this kind of the same thing that I gave in my book about the brick stallers your clients. You're writing something about bricks, Brazil, Russia, India China and Saudi Arabia. And there's a couple of companies that's the bricks. Nations have been floating for about 15 years. A new bricks dollar that would be commodity based.
If you have a barrel of oil, you get so many bricks dollars. If you have a bar of gold, you get so many bricks dollars to combat the US dollar as a fiat currency. This is the bricks dollar. The problem is the US dollar is. Is the very best product a mankind has ever invented.
You make trillions of these things and people will lie, cheat, and steal to get 'em and people like me and you'll work 80 hours a week to get 'em. Then they'll make trillions more off, off their assembly line. There's another trillion and people will lie, cheat and steal to get cheat to get 'em and me.
And you'll work 80 hours a week to get 'em.
Yep.
It doesn't matter how many they make. We still want, it's the greatest marketing you've ever seen. Look, we, lemme just go really quick into a little bit economics, because your question is more, about the digital and going into digital dollar and such.
And I think it's eventual that they will eventually do it. But it's gonna be a fight. Because we look, we bought tech, we bought Alaska for $7.2 million. An incredible real estate deal.
Yeah.
Then we bought the Louisiana purchase for 4 cents an acre.
Those are incredible deals.
Those are probably the best deals in real estate ever made. However, there is one deal that is far better. It's called the Euro dollar Now. It's not the euro. The Euro is the dollar that the European countries, and people mix this all the time, the Euro on the Euro dollar are two different things.
The Eurodollar is the US dollars outside the Federal Reserve system. So when like Saudi Arabia lends to Turkey, 16 billion US dollars from Saudi Arabia to Turkey, that's a Euro dollar. And they believe there's over 30 trillion Euro dollars in the world, like Indonesia's buying stuff. 30 trillion, right?
And it's really hard for our country to get off that system. It's a crack addict trying to get off crack, right? You've been using it. And so after World War ii, they in introduced the Eurodollar system and so many people use, you can get off the Euro, you can get off the US dollar.
It's just gonna take decades and decades and decades. And it's gonna be a big fight.
You're
not gonna just, that's a great idea. We should just switch because you can't, it's just, you can't get off it because when Tur Turkey has to go find. 6 billion US dollars to pay off Saudi Arabia.
And that creates demand for the US dollar. So anyway, I, that's part of my book a little bit.
Yeah. And I'm just curious for investors or even family offices that are listening today, where's that sweet spot when it comes to their own portfolio between, having say real estate backed to assets versus digitally backed to assets?
Yeah. The risk. The risk right now that they're talking about is quantum computing in digital assets. As far as I know, IBM claims to have a quantum computer, but that computer is so fast, I just don't think the public's ever gonna be able to get to it. And I think the US government is going to pull it up because it's too far advanced.
Like right now, when I see, if I send you a wire transfer, you know it's encrypted. And if I had a laptop or a computer, I could break that encryption in about, I don't know, three or four oh years. My, my computer could do it, right? But a quantum computer could break it in minutes, right? And therefore, the, this theore theorized that a quantum computer could break the the blockchain and infiltrate the blockchain.
But that's, this is all theory but right now, blockchain, the Bitcoin it's the greatest idea I've ever heard. I'd love the, I love I own Bitcoin and I own some crypto and but 90% of my wealth is in real estate or real estate backed companies. And it's the long game and I, but I wanna have some exposure to the crypto as it comes along and the blockchain, because it's a fantastic idea.
The, it's a, it's the best idea ever heard. And the only reason it's not worth more than now is because the nanosecond, it was invented. It has to go up against the biggest, baddest opponent. On the planet, the Federal Reserve, the IRS, the SEC, the the US government, the US President you have those are, they control the US dollar and their number one job, their number one job.
The federal's number one job is to protect and promote the US dollar. People think no, their job is inflation or, unemployment. Those are a few of their jobs. What they don't, what they don't tell you is, as long as everyone in the world accepts US dollars. Jeanette, me and you, when we fly around the world, we hand out a US dollar and they take it.
That's not true for other countries. You don't just fly around the world and you have your own currency and try to buy stuff. And so anyway that's the balance. And so anyway, like I said, 90% I'm still in real estate. And I have some gold but not physical, digital gold.
And then I have, a small, a percentage of my portfolio in crypto is in Bitcoin. Yeah.
Interesting. All right before we go to what I call the lightning round questions, I have one last question that I wanna talk to you about because I think it's very applicable, especially to anyone that's in a role of leadership, or especially as a founder.
So when you retired, how did you go about planning your succession? It's become a big thing, right? Everyone loves the show succession now. But the reality is that it's very critical when you have such a key role and you try to make an exit for investors to still have confidence.
Yeah. And hopefully for, your memory and the culture that you've created to remain intact, within that, that, that institution. So what advice do you have for somebody that is focused or maybe getting to that season of their life where succession planning is very important for them?
Yeah, so I, I think it was a over a year, maybe a year, almost a year and a half that I told my partners I was gonna retire. It's a long runway kind of thing. The bad thing to do is say, Hey, I'm decide to retire, and I'm gonna retire in three weeks's. That's not a good thing.
And me being a, a significant shareholder. I don't wanna hurt my company, I want my company to blossom. And keep going even after. So I think that's the key, to have confidence in your position and confidence in your partners and people that are gonna, succeed. And like I said, we had a great group of guys that were partners and, went to them and, basically said, I think I'm done and I'll be done in six months or a year or maybe 18 months, whenever we can find the right time and the right.
Person to take over. Now, right about then though, what happened was about a few months into that I got wind that my partners were thinking about going public on New York Stock Exchange. And I was going, whoa. I said, okay look, any kid that graduates from business school in college. Their dream is to go public on New York Stock Exchange.
And I said, look, I'm gonna look, I wanna slow down and bring the person and train the person, but I always want to hang on until the last few months. We go public and I'll retire the next month. So I had a lot of time to look and help my succession and plan it out all out. And and then help the person that came in to, to take over my position and they hired a few more people.
I, I had a lot of hats. I just didn't do one hat as a what hat tell you what happens as a co-founder in my scenario when you're small company. You have 17 different hats, okay? And you grow a little bit, and then they hire someone to take these two responsibilities away from you.
And those two responsibilities get done better than you were doing it. 'cause that's all they, this person only does those two. You were doing 17. Okay? But what happens over years and years and years, and if you grow like we did from zero to 28 billion and. And the thousand employees. What happened to me was I got stuck with all the boring stuff that no one wanted.
Okay. So I'm like, yeah, maybe I should retire, but un entrepreneur. 'cause when you go public on a public stage, you're doing a lot of reports. Report, weekly, monthly, and that's the. Antithesis of being an entrepreneur, reporting to people. What you're doing is anti entrepreneur, right?
And so it was my personality was time to to go anyway. And I wanted to retire anyway. I was done. So anyway, I long answer to your question is give yourself a long runway. Have confidence in the people that are there, that they understand and that you're there. You and I told 'em, I saw I'll be here six months, nine months, a year until it's right.
I don't have a deadline. And it even went 6, 7, 8 months and then I extended because of the, and that. And when you go public in exchange, people want to see the consistency that no one just left the company. So it helped a little bit, not a ton, but it helped me a little bit that I was, been there from the beginning and I was still there when the company went public.
Yeah.
How did you adjust to retirement? Did you find yourself, absolutely bored outta your mind? Six weeks later? No.
People ask me that all the time. Are you bored? No. I live in the United States of America. This is the greatest place in the world. I do fun stuff ever like this.
I do fun stuff every day. And yeah, I am, I have friends though. I do have friends that are retired and they're thinking about going back to corporate Americas 'cause they're bored. Tried them a little bit, and I say, do you live in the same country that I live in? I don't get it. But anyway that's, you teaches his own yeah.
Yeah. All right. Good. John, we've arrived at what I call the lightning round questions and these Okay. Five fun little questions that I ask all of the guests on the show. So are you ready?
I'm ready. I'll get ready. Yeah.
All right. And you're gonna have to expand upon your last answer there, because basically I was gonna ask, what do you actually do for fun?
I offroad motorcycle ride. I write some books, which is fun. It's, it is not a, it's not a, it's not a thing for money, it's just fun. I mentor a bunch of people, a lot of my son's friends and and nephews and stuff and probably 30 mentoring over the phone and over Zoom calls.
I speak at friends events, they had the mastermind events. I'll go speak and do a slide slideshow on dollars, golden Bitcoin, and I promote my book and I've got my grandkids that are all live within a few miles of me and. They come swimming and we go boating and yeah. So I've got a lot of things to do.
Yeah. Yeah.
Nice. Nice. Very good. All right. Now this one is probably gonna be a little challenging 'cause you have been out and in front of, people from years and years. What is something interesting about you that most people don't know?
Oh man. That they don't know about
me. Yeah.
Let's circle back and come back. Lemme think about that for a minute. I think people know a lot about me, so I don't know what they Exactly. They, exactly. Okay. Alright.
It could be anything, really weird you can raise, alternating eyebrows at a rapid pace.
Just something quirky.
Oh. I've got one. I, yeah. It. I'm 61 years old and I swim in the Huntsman, senior World Senior games.
Oh, wow.
And I swim the butterfly, the breaststroke, and the freestyle. And I'm a sprinter. I'm not a long distance sprinter. And I won a gold medal last year in the a hundred meter.
Breaststroke a hundred meters. I did it in one minute, 27 seconds. Wow. In my, and I got a gold. So that was, that's pretty fun that I can still swim pretty fast for an old guy, so that's fun. Yeah.
Yeah. That's super cool. All right, good. All right. Now what about as far as books or podcast?
Now, obviously you have your own book, which we would recommend people take a look at, but is there any other book or podcast that you just really found to be instrumental in your own? Development towards achieving all of your success?
I don't, I wouldn't say that I never had a mentor or anything like that.
I I've told my boys, that's one advice I give to my sons. When they were in college, I said, look, you're not gonna do it like me. I had to work 40 hours a week in college. I dug trenches and put sprinkling systems in people's yards, and then went to school nights. If I can go back in time, I would've taken out loans and I would've done internships.
I would've done, I'd worked for free for a bank or something. I would've been learning. And I, so my sons and stuff I've said, look, you're not gonna do what I did. You're, I'm gonna, we're gonna, whatever. You're going to do internships at different companies and you're gonna do, and so that's my advice to the younger crowd that's in college.
Is take out some loans. Don't waste that time. I know you gotta make money, but there's some, a balance there that there's, that's a time in your life when you're just sucking up all the great stuff out there. But afterwards, in the last few years, I think in real estate, I.
A guy named Jason Hartman, who I've met a couple times and he endorsed my book. He does a great podcast. I think your podcast is fantastic too. Jason Hartman does a real estate podcast, I think two or three times a week for investors and real estate stuff. So that's one of in the real estate world that I would say that I really enjoy.
Jason Hartman. Yeah.
Nice. Excellent. All right. And then, one of the other things too that we'd like to always draw attention to is, yeah, we all wanna make good money. We wanna have some nice returns. That's all fantastic. But the point is about really being able to live and build extraordinary lives.
And so what is your advice to someone that is focusing on that?
Okay. I know this guy named Bud. He's 77 years old and he's got 61 grandkids, great grandkids and kids, and he brings 'em together. This is a true story. They were they went to this resort outside of Las Vegas, it's got pools and houses and stuff, and he invited one of his friends that's about his same age in Las Vegas that never was married, never had kids, and came to this whole family reunion thing, and the guy basically said to my friend, bud.
You and this guy's very wealthy, okay? Both of 'em are very wealthy and he said, look at this. You have something that can't be purchased. You have something that takes decades to build. And a lot of people, even if they try for it, can't get it right. I know some people can't have children or whatever.
I know some people don't get married. I get it. But he was just elaborating that this is fantastic. And you go, the guy goes, I can't purchase it even though I have all the money in the world. You have to start when you're young and you have to build with a long-term goal. And I think that is where I derive the vast majority of my success and happiness is family and having family close and having people that there's always people that in their, in your family, that are lost their way for a little bit or not doing what it, it's all good as long as you stay together.
And I would say. As far as building your real estate empire or your company empire or whatever you're trying to build, I would say that keeping the team together rather than ex, pushing people away, even though sometimes you have to take, you have to do things you, you normally wouldn't do, but you accept and just keep the team together is very important for longevity and in, in reality as people know that you accept them.
It all works out in the end. And it's a great thing because. You cannot buy it, you can, it, it just takes a long time to build it, and it takes a long time to put it together, and it doesn't always work out perfect, and it probably never will work out perfect. But it's a it's fantastic.
It's fantastic.
Love it. Love it. Yes. It's something that I say often that it's the people in your life that make it what it is. Yeah. Very much nice. All right, and then last but not least, John, if folks wanna get in touch with you, how can they find you?
LinkedIn, John S. Pennington, Jr. And there's one thing before, yeah, LinkedIn is the best play.
John S. Pennington Jr. LinkedIn and, or you can go to John S. Pennington jr.com. But it's one thing I wanna leave with you that changed my life when I was 17 years old. A little quote. And I remember looking into the mirror, I was 17 and I knew, like I told you before, when we first started, I couldn't do corporate America.
And I said these words and I, and these words, I've said over and over to myself over my career. And I looked in the mirror and I said, John, you're not afraid of being poor and you're not afraid of being old. You're just afraid of being old and poor at the same time. And so over the years when I could buy a really nice sports car.
And I didn't, I, I kept the, the Ford Expedition with the dent in the door when I could. And I, that was always in the back of my mind. I'd never want to be old and pour at the same time. So I kept using my dollars. I. To reinvest in long-term things, real estate, which is it, which is it's a long term.
A lot long term. So I would encourage people and my people that want me to mentor them, I say, listen, once or twice a year, look in the mirror and say, I'm not afraid of being poor. I'm not afraid of being old. I'm just afraid of being old and poor at the same time. And it will change the way you think about here in America is the greatest country.
Crazy for an entrepreneur. I'm not, I don't know if we're the best at math. I don't know if we're the best at, English. I don't know what I don't know. But I do know if you're an entrepreneur, this is the best place in the world to be. Do we have financing? We have ev, we have everything you need as an entrepreneur to be here.
And all you gotta do is wake up every day and try and if you're an entrepreneur and you gotta stay healthy. Wake up every day and try eventually you'll succeed. And like I said, I had 14 businesses in my lifetime. Three lost money, three made a ton of money, and the middle ones did great.
And so that's what I've told my boys and people I mentor. Don't be old and pork at the same time. And there's so much money here if you can resist the Lamborghini. I shouldn't say that because I don't have some founder just bought Lamborghinis. But what my point is if you can redu, if you can resist the, the short term things for long term I believe that has been my secret power over my years of entrepreneurialism is I always had a war chest and when, and I always knew if this company fails, how long can I go without having to go get a job? And it's all based upon how much I saved in the good times.
And over this. And then finally the last one, 2004 on it was like after about two, 2009, 10, 11, 12. It was so large. The company was so large, it didn't matter anymore. And I'll tell you a quick story. I know. We're outta time. No worries. My my family didn't know how wealthy we were. And my son started five businesses right outta college.
He was a Chinese tutoring and building websites. And I said, look, why don't you go to my partner? I talked to him. He's gonna be your mentor or whatever. Go see him. So my son tells this story on stage. He drives to this beautiful neighborhood private community, knocks on the door. My partner comes to the door, brings him in the house, has sports cars in the garage.
A indoor basketball court pool. In the back, off the deck, you could see the 20 miles view, right? And they sit down on these big white couches and they talk, talking about whatever. And my partner says, look, start your own investment fund. That's what me and your dad did. And he goes, yeah, I know.
I want you to be my be my my son goes, I want you to be my mentor. And he goes, your dad knows more about funds, real estate funds than I do. I want, don't you to go ask him. He goes you're obviously way more successful than my dad. And he goes, and he left the Be out. He says, lemme tell you a secret.
Me and your dad make the exact same amount of money. And at the time I'm driving a expedition with a dent in the door. And living in a regular house. So my son comes home anyway, the cat's out of the bag. I thought I could stay under the radar for about five more years before, but I was using all my money to reinvest into my own funds.
I'd get a little, I'd get the big bonus check and I would reinvest into the multifamily fund, this owner check re reinvested in the senior living fund. I was building more, down the road anyway, that month. I got a Tesla. I bought my dad a Tesla for his birthday. My wife got a Range Rover.
My boys got new cars. My father-in-law got a car. I probably spent a half a million dollars in cars in the next couple months or whatever. Anyway, but I'm saying, what I'm trying to say is it was my mental all the way back when I was young. I don't wanna be old and poor at the same time.
And that's what drove me. To start businesses and keep going and, do it better and faster and cheaper than anyone else and bootstrap it. That's what it really was. And I repeated that thing in the mirror to myself probably three or four times a year through 40 years.
I.
Wow. Very interesting. John, this has been very inspiring interesting and even funny you're a great storyteller so I really appreciate you taking some time to just come and share with yourself and your life, with us today. So thank you so much.
I, it's been a fun and interview and thank you.
Thank you very much and good luck on your success.
Ah, thank you for those of you that invested your time with us today. Thank you. Please make sure to leave us some comments. Let us know anything else you want us to dig into, and in the meantime, be bold, be extraordinary, and keep moving forward. I.
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