Go Big Once: The Mindset Behind Building Generational Wealth with John Pennington

Summary

The $100M Entrepreneur Podcast

Episode: Go Big Once: The Mindset Behind Building Generational Wealth with John Pennington

Host: Brad Sugars
Guest: John Pennington
Date: February 11, 2026

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Main Theme

In this episode, Brad Sugars sits down with John Pennington, a prolific entrepreneur who started 14 businesses before building a multi-billion-dollar fund. They explore the crucial mindset, strategies, and structures required to create generational wealth and scale a business from millions to hundreds of millions—highlighting the necessity of going big, attracting top talent, raising capital, and architecting companies for eventual sale or succession.

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Key Discussion Points & Insights

1. The Power of Structure & Mindset in Scaling (00:00–05:40)

• Early Ambition: John describes a formative moment at age 17, realizing his core fear was "being old and poor at the same time." This fear drove his desire to build something truly big.

  • “John, you’re not afraid of being poor. John, you’re not afraid of being old. John, you’re just afraid of being old and poor at the same time.” – John Pennington (00:13)

• Choosing the Right Vehicle: After starting 13 companies (some successful, some not), John’s 14th business was a fund—a structure he saw as inherently scalable and shielded from typical corporate pitfalls (like getting ousted by shareholders).

  • He tells the story of Steve Jobs being fired from Apple, emphasizing why he preferred the general partnership/limited partnership model, where the general partner—in this case, him—cannot be voted out except in cases of fraud. (01:40)

• Snowball Effect: Once John's team mastered the fund structure, scaling became exponential, primarily by tweaking the asset classes (“I couldn’t stop it from scaling. It was just snowballed…” – 03:30).

2. Talent: From Employees to Equity Partners (05:40–07:19)

• Finding Better Talent: John realized to scale exponentially, he needed partners who were true experts, not just employees.
  • “You and I aren’t smart enough to run a big company. We gotta find better talent, smarter guys than us.” – John Pennington (00:28 and 15:36)
• Ownership Mindset: He offered equity in the general partnership rather than just salaries—particularly targeting people who’d never had equity, but had huge, specialized experience (e.g., underwriting massive apartment complexes).
• Timing Opportunity: The 2008–2009 financial crisis made experienced talent more open to risk and ownership, allowing him to “acquire partners” he otherwise couldn’t.

3. What The First 13 Businesses Taught Him (07:45–08:45)

• Failure as Tuition: John insists he wouldn’t erase his failures, as the lessons from struggling businesses (“how can I make payroll by Friday?”) directly enabled his later success.
  • "Those learning losers... I use that skill set when I started that first fund in 2004.” – John Pennington (08:12)

4. Deciding When to Go Big (08:51–11:58)

• Life Timing: At age 40, John made a conscious decision—if he wanted to build something huge, he had to start then, since a large-scale venture could take 5–6 years to even know if it would succeed.
• Fear & Motivation: He returned to that original fear (“old and poor at the same time”) repeatedly as motivation.
• Conservatism Amid Success: Even as his AUM ballooned from $100M to $8B, he was “conservative,” focusing on never being poor again and protecting wealth, rather than endlessly risking it.
  • “Once you see people get rich and they’re broke...they risk too much. You get rich once, and you kind of have to change the game.” – John Pennington (11:38)

5. Exit and Scalability Strategies (13:05–16:00)

• Designing for Exit: Unlike entrepreneurs who build themselves into a business “job,” John structured his fund so it could run without him—true business owner independence.
  • “If I have to go in and run everything every day, it’s not a business. It’s a job.” – John Pennington (13:38)
• The Myth of Family Succession: Most entrepreneurs say they’ll pass the business to their kids. Brad and John agree that’s rarely realistic.

6. Professionalizing Management for Scale (15:08–16:01)

• From Startup Rockstar to Professional Leader: Both men emphasize the need for professional management and a leadership team to reach $100M+.
• Equity, Not Just Salary: Equity was the key to attracting and retaining partners with the right “owner” mindset.

7. Raising Capital and Institutionalization (16:07–23:49)

• Different Skills, Different Money Sources: Raising from high-net-worth individuals, family offices, and institutions all require distinct personalities and approaches.
  • "Institutions…they don’t even come out to see you unless they can write you a $30 million check." – John Pennington (17:43)
• Preparation for Institutional Investors: John’s team had to “become what institutions want”—investing in big-four auditors, compliance, and infrastructure years before attracting a large investor.
  • “We have to become a company worthy of an institution before the institution comes.” – John Pennington (18:34)

8. Fund Structures, Regulations, and the Economics of Scale (23:49–29:00)

• Legal Frameworks: John discusses private placement exemptions (506B 3C1, etc.) and fund documentation costs—underscoring the scale required to justify the legal and compliance investments.
• Equity Compensation: Breaking down the classic “2 and 20” fee structure and why he wanted to be a general partner versus a broker or agent.

9. Wealth, Frugality, and Lifestyle (29:00–30:53)

• Living Under the Radar: Even as he built generational wealth, John drove old cars and lived modestly—reinforcing the principle of investing windfalls rather than upgrading lifestyle prematurely.
• Wealth Mindsets:
  • “Rich people: ‘How can this money make me more money?’ Middle class: ‘This money can help me get a bigger house...’ Poor: ‘This money can help me eat today.’” – John Pennington (27:15)

10. The Mindset Shift from $1M to $100M (30:53–33:16)

• The Trade-Off: John observes that some business owners (the successful dentist, for example) may have no desire to risk their comfortable life for generational wealth. For those who do, it’s more about internal drive than any single tactic.
  • “Just once in my life I want to go for it all. I want to go large...I want to see what can I do in this life?” – John Pennington (31:38)
• Permission to Fail: He notes the value in the ability to try and fail, “can you imagine you lived a life where you couldn’t fail at anything? It’d be boring.”

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Notable Quotes & Memorable Moments

• On Fear and Motivation:
  • “John, you’re not afraid of being poor...you’re just afraid of being old and poor at the same time." – John Pennington (00:13, 10:04)
• On Going Big:
  • “Just once in my life, I want to go for it all...I want to see what can I do in this life?” – John Pennington (31:38)
• On Structure and Ownership:
  • “If I have to go in and run everything every day, it’s not a business. It’s a job.” – John Pennington (13:38)
  • “We have to become a company worthy of an institution before the institution comes.” – John Pennington (18:34)
• On Raising Capital:
  • “There’s a personality for raising from individuals, a personality for family offices, and a personality for institutions.” – John Pennington (16:35)
• On Wealth Mentality:
  • “Rich people: ‘How can this money make me more money?’ ...Middle mentality: ‘How can this money get me more in debt but a better lifestyle?’ ...Poor: ‘This money can help me eat today.’” – John Pennington (27:15)
• On Role of Partners:
  • “You and I aren’t smart enough to run a big company. We gotta find smarter guys than us.” – John Pennington (00:28, repeated 15:36)
• On Exit Planning:
  • “You will have an exit in your business… pine box, shut it down, or actual sell.” – Brad Sugars (12:26)

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Timestamps for Key Segments

• 00:00–01:40: John’s motivation, earliest ambitions, and initial realization about fund management structures.
• 03:30–05:40: The exponential scaling achieved with fund structure and the role of bringing in superior partners.
• 08:12: The value of learning from failures in early businesses.
• 10:04–11:58: The personal calculus and mindset required to risk going big with a business.
• 13:38: Defining what makes a “real business” versus a job.
• 15:36: Leveraging equity for talent.
• 16:35–19:22: The multiple personalities required in capital raising, and gearing up a company for institutional investment.
• 27:15: The three-tier mindset about money and wealth.
• 31:38: The internal drive to “go big once.”
• 32:40–33:16: Embracing the possibility—and value—of failure.

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Conclusion

This wide-ranging, candid episode traces John Pennington’s journey from early ambition to generational wealth, emphasizing the necessity of picking scalable structures (like funds), attracting and partnering with the best talent, intentional preparation for scale (especially in compliance and capital raising), and the vital difference between growing rich and merely looking rich. The central lesson for listeners: building the foundation and mindset for $100M+ success takes hard-won lessons, the humility to bring in smarter partners, and the courage to “go big once” even when familiar success is comfortable.

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If you’re at $1M and looking up, this episode shows both the magnitude of the mindset and the level of action required to move toward generational wealth—underscored by readiness for risk, relentless preparation, and the willingness to scale with the right people, systems, and vision.

Transcript

[John Pennington]

Stockbrokers make 1.5%. A mortgage broker makes 1%. A general partner makes 20% of the profits. I want to be one of those guys. When I was 17, I looked into the mirror and I don't know why I said this, but I said, john, you're not afraid of being poor. John, you're not afraid of being old. John, you're just afraid of being old and poor at the same time. I was like, dude, I want to run a huge, huge company. I would look at him and laugh. I'd say, you know, you and I aren't smart enough to run a big company. We gotta find better talent, smarter guys than us.

[Podcast Host]

So, John, let's talk about big success, big scale. Latest business number 14 boomed. How. What? Hundreds of millions is not a thing that most people get to.

[John Pennington]

Yeah, true. So I started 14 business in my lifetime. Three I lost money on, three I made money on, obviously. This one I made a lot of money on. And then ones in the middle, you know, you kind of make some money on them, right? Yeah. But the other 13, you got them to, you know, you get them to a certain size, and they just won't scale. I mean, they. It. Well, they will. This is hard. It's difficult, right? But the 14th was a fund structure, and I learned about funds in 1999, and I was watching this newscaster vilify fund managers on. You know, these are villains. They. They pay low, low taxes. They make a lot of money. And I'm like, I want to be one of those guys. So in 2000, it took me five years to get the gumption and the confidence and all the knowledge to launch my first fund. It's a general partnership, limited partnership structure. And I learned that, you know, Steve Jobs went public New York Stock Exchange as an Inc. And every year, an Inc. The shareholders vote on who runs the company. But in a general partnership, limited partnership, the shareholders, the people have the money, never vote on who runs the company unless the general partner commits fraud. And I thought, you know what? I don't want to build a nice big company and then have someone say, you know what, John, we really appreciate that, but now I want my son to run it. I never want that, John. We fire. Yeah, yeah, yeah, yeah. So Steve Jobs got fired from his own company, and Steve Schwarzman of Blackstone went public in a general partnership, limited partnership structure. Same thing. The shareholders do not vote on who runs the company. So. But a fun structure was a. The 14th business, you know, that I ever started, and I did it with some Great partners. I had brilliant business partners, but it just, I couldn't stop it from scaling. Yeah, it was, it was so, just snowballed when you started the first one. Oh, I got the first fund down. Now let's go to the second one and the third one and the fourth one. And really you just tweak the asset class. And so the first fund I ever started, we lent money on real estate. And then the third fund we started was we bought large apartment complexes. And then the fourth, fifth fund was, it was senior assisted living for that fund. And the next fund was office buildings, and the next fund was industrial. You know, it just, it just was just separate funds and they, it just scaled like, I couldn't stop it from scaling. It was, once you got, once you got the formula down. And so the structure, really, really, if I Look at the 14 businesses, the structure was really kind of the key, but you still had to attract great talent. And so, like, for instance, when we started purchasing apartments in 2008, 2008 was a bad time. Oh, yeah. And I, I knew how to underwrite a 200, a 20 unit apartment complex. I can do it, but I needed someone who could underwrite a 1200 unit apartment complex. I don't know how to do that. So I'm, I have to find people with much, much greater talent in certain areas that I have. And so I, you know, I would lay in bed imagining at night there's, there's some dude or some lady, she's been working at Wells Fargo for 15, 16 years and they been doing loans on 1200 apartment complexes for, and they know how to underwrite it. And I imagine this person driving to work every day going, one day I'm going to quit my job and start my own fund. And I'm going, I got to find that person. I know they exist, right? And so when I found those, that person, I was like, you know, I don't want you to be an employee, I want you to be an owner of the general partnership. I want you to come in and own it. Now, listen, you're going to, we have some money, cash flow, you're gonna, your salary is gonna go down, but if this works, you're gonna make way more money than you ever imagined running a fund, right? And, you know, we found, you know, my original partner, we found two gentlemen who had been doing real estate for, I don't know how many years. It was like gazillion years. And they were just experts in large real estate, and we were experts in funds, right? So the two of us, boom. We knew how to run funds, they knew how to run real estate. And it was. And then we just jumped, jumped and brought in more partners that even. And it just snowballed. And you know, 16, 17 years later, we go public on the New York Stock exchange. We're managing $28 billion of asset or management and we have employees, we have thousands of employees in 33 states. Right. I had many, many jobs at that point. When we retired, I, I was the president of over 100 corporations in Delaware. I was a signer. I was a signer on 1200 bank accounts at 19 different banks. I was. Yeah, yeah. Not 120, 1200.

[Podcast Host]

Just scale.

[John Pennington]

Yes, yes. I was the anti money laundering officer for eight of our Cayman island feeder funds. That was a job, man. I did compliance, SEC compliance and all SEC issues for all of our employees in the 33 states. You know, I had many, many more jobs than that. Right, but.

[Podcast Host]

And we wonder why you were tied.

[John Pennington]

Yeah, yeah, exactly, exactly. Yeah, yeah. We went public and I was like, you know what, I'm good. And so my partners took off and they've done even incredible job. I'm still a large shareholder, but they've done incredible job going forward and they've even raised more money, got bigger and bigger and they run the company way better than I did, you know, and we ran it together. I had pieces, but like I said, you had to find talent in specific areas to go large. And what we used was ownership in the general partner are. We believed. And I believed from the first I was looking for people who didn't want to be employees. I was looking for the mindset. They wanted to be a entrepreneur, they wanted equity. And some people had never had equity. They had huge jobs over here, never equity. And I wanted, I wanted someone that wanted. And in 2008, 2009, people were willing to take a chance and I was able to gobble. I shouldn't say gobble. I was able to acquire partners that would have never been my partner. If it wasn't 2008, 2009, if it.

[Podcast Host]

Was like 2004 when everything was booming, everybody's.

[John Pennington]

They would have never been my partner. Yeah, there was a. Nah, Johnson. No, I don't want to be a part. No, no, no, no. But 0909 right there we got some. And then they came in and they were equity owners and the company just went.

[Podcast Host]

So two things out of that then. Firstly, you got the strategy correct. And secondly you got the talent, let's go strategy. What was the difference in strategy of this one versus the previous ones, how did they almost, I guess, teach you? Because I define scalability as the next sale costs less and is easier, you know, so it got easier as you got bigger in this one. The strategy was on point.

[John Pennington]

Yeah.

[Podcast Host]

What did the first 13 teach you that led you to that thinking?

[John Pennington]

So I just answer that in a kind of a, just a holistic. Right. People say if you can go back in time when you're changing thing. No, because I, the three, the three companies I lost money on, if I wouldn't have lost money on those companies, I would not know I would have lost on this company. Right. So I learned these things way back when lose. So I would not go back and tell myself, don't do this, don't do that. Because those learning losers. You wake up on some Monday mornings and you're like, how can I make payroll by Friday? You know, and you're like scrambling and you're learning how to, how to, how to solve, solve problems. And I use that skill set when I, when I started that first fund in 2004, you know, so it's just, I don't know if I go into details there in time. We have, but it's just a, it's a process through life where people want to go back and change their past. But that means you'd be different today. Yeah. Right. So, yeah.

[Podcast Host]

So the people thing did. Is that something you had to learn over time or were you always find the best people type guy?

[John Pennington]

No, it wasn't always. I. Earlier businesses, I was just wanting to hire employees. I wanted to hire good employees. But this is what happened. I'll give you the strategy here. So I'm 40 years old when I start my first fund. Okay. And I played my life game out. And I always said to myself, I want, I want. Once in my life, I want to go huge, I want to go for the stars. Right. And if you go for the stars and fail, well, you know, so usually what I do, you know, it takes a year or two to see if a business will work. And then if it fails, you've lost a lot of money. And then you take another year to find another business. So now you're four years into a smaller business, but a really, really big business. It's going to take you five to six years to see if it really works or not. And if it fails, you've lost six years and a lot of money and you're going to have. So if I'm 40, I was like, well, John if you wait till you're 50 and you go, and you go big, you'll be 56 and you'll be, that's square one. You don't have enough time to recover and retire. So, John, if you don't go try to go big at 40, you're never going to do it because you're a conservative dude, you know, you're not going to risk your family. That's just the way you think. You look in the mirror and you think this, right? And when I was 17, I looked into the mirror and I don't know why I said this, but I said, john, you're not afraid of being poor, John, you're not afraid of being old, John, you're just afraid of being old and poor at the same time.

[Podcast Host]

How did your 17 year old. I don't know.

[John Pennington]

I don't know. I don't know how I did that, but I was, I was, you know, you're 17, you're thinking, what am I going to do in life? How am I going to make money, right? And I just kept narrowing it down to what is it really? What's really in there, right? And I, I was afraid, right? I was seriously afraid of not being able to figure out in life which, whatever. So that, that mirror, I, I said it to myself for years and that drove me through the companies I failed at. And the ones that did okay, and the ones, it was just, John, John. And so by the time 2015 rolled around, we're managing 8 billion. And I knew at that point, I'm never going to be poor again, right? Yeah, yeah, yeah. So I'm conservative. I'm conservative, right? So when we were managing 100 million, I went, how much? We managed 100 million. And then someone says, we're managing 500 million. I went, what? And then when someone said, we're managing the first billion, I was like, no, no, it can't be a billion. So I got my calculator out and I'm like, how, how, how much is a billion seconds? Yeah, yeah, it's 31.7 years, right? I said, wait, a billion seconds is there? And we, we're managing a billion. And then like a year and a half later, we were like, 3 billion. I was like, what? And then we, when he's six or. I was like, okay, I'm never going to be poor again in my life if I, if I choose to be right. And Warren Buffett always says this, you'll have to get rich in, in the United States. Once you see people get Rich and they're broke. Rich and broke. They're idiots, right? I think they risk too much. You get rich once, and you kind of have to change the game, right? It's like if you're ahead in a game by a lot of points, you play differently, right?

[Podcast Host]

They all protect.

[John Pennington]

Yes, yes. And I'm like, you know what? I'm going to protect it.

[Podcast Host]

You know the crazy thing. And you know, coming from Vegas, people don't take their money off the table in business either. They. They keep running that thing.

[John Pennington]

And I wonder why they do that. I.

[Podcast Host]

You know what? I think that's very few people, John. They learn how to sell their business. Very few people. I literally say to every business owner, you will have an exit in your business. You get to choose pine box, shut it down, or actual sell. Now, if you want to sell it for value, it's going to take us two to three years of planning to sell that thing for value. And most like, you look at the baby boomers right now, holy heck, you got like, across the US right now, we got just under 40% of businesses are owned by baby boomers who got 5 to at most 10 before they got to be out. There's a massive transfer of wealth coming. And I don't think. Think that. That they understand it. But I, I sit with most people and I ask them, you know, like, a simple dumb question is, have you trained your managers? And they look at me like, no. And then a super dumb question is, well, what's your business worth and what do you want to sell it for?

[John Pennington]

Right?

[Podcast Host]

And they look me and I go, I'm going to pass it on to my kids. No, you're not. Your kids don't want your business. So it's interesting that, you know, in your business, you almost, from day one, built the sell strategy into the business. Talk more about that. Building the sales strategy in.

[John Pennington]

Yeah, so it's. It's. It's. It's the mentality of sub. I've seen. I have friends that have this. They run their own businesses and they go to work and they want to handle everything. And I was the opposite. I wanted people to. I wanted to be able to leave my business. And that's a true business. If I have to go in and I have to run everything every day, if it doesn't run, it's not a bad business, really. It's a. It's. It's. It's a. It's. It's a job.

[Podcast Host]

And you learn for an age.

[John Pennington]

That's right. You work for yourself. You work yourself, but it's a job. So if you can, if you can leave your business for weeks at a time and it runs, maybe doesn't run exactly as right, but it still runs, you have a real business. And that's the underlying goal of a entrepreneur is I want to create a real business where I'm not running it every day. I'm the present CEO. I'm visualizing where this business is going to be in two or three years and I'm creating contacts or relationships with customers or wholesalers that is going to expand or acquisitions that's going to expand this business. Right. So that's the kind of the vision that I had when I said I want to go big at 40. Yeah.

[Podcast Host]

Your buddies that are the bottleneck of their own business. You know, it's, it's great to be the rock star on your way to a million dollar a year business. Yes, you should be, but you, you can't be the rock star at 100 million.

[John Pennington]

And this is why I think your company, your product is because a lot of entrepreneurs get to a certain size and they can't figure out how to make that transition from. I'm intricate in the business, but that's not really my role anymore. It was when you started it.

[Podcast Host]

Yeah. How do you build the managers and the management team to get the 10 million then how do you build the leadership team to get 100 million and beyond? And I think that goes back to your point of hiring great people. At some point you got to professionalize management of the organization or professionalize lead leadership of the organization to get it.

[John Pennington]

And, and we used equity rather than a high salary and bonuses. We used equity to find that type of person. I just explained to attract the talent.

[Podcast Host]

That's right.

[John Pennington]

That's right. Because our, my goal was look in the beginning my, my first me and my first partner, I was like dude, I want to run a huge, huge company. And I would look at him in laugh and we, I'd say, you know, you and I aren't smart enough to run a big company. We gotta find really big, better talent, smarter guys than us. And, and we did, we did. We found part that were smarter, way smarter than us and, and just took, took it to heights that I never could have imagined.

[Podcast Host]

Yeah, yeah. I think that's the thing. But let's go flip it over a second scale requires capital.

[John Pennington]

Yes.

[Podcast Host]

You want to scale exponentially grow a business, you require capital. One of your key skills has been raising capital. Tell me more about how that works. Why it works and why were you damn good at it?

[John Pennington]

Yeah, I'm a good capital raiser. I'm not a great capital raiser. And so I had to find, again, people who were great capital raisers. And what I found over the years was there are three really different personalities in raising capital. We found that there's a personality that can raise capital from high net worth individuals. There's a middle personality that can raise capital from family offices and banks and stuff like that. And there's a third personality that can raise capital from institutions. And so usually up the scale, your first couple years, it's high net worth, High net worth, high net worth. Then you try to go to the family offices, and it takes you a few years to get into institutions, because institutions, they don't even come out to see you unless they can write you a $30 million check. And they won't even fly out to see you. And they don't want to be 30% of your fund. They want to be like less than 15% of your fund, but they want to write you. They want you at least a $30 million check. And they do question. They ask you questions, do due diligence, that you have no idea how inclusive it is. So it takes you years of being like one of my partners, early partners. We had an audit. We had. All of our funds were always audited. But in our town, we had. There was an auditing firm. They were 50, man ish. They were local, they were good. I'd used them for two decades. And when we started our third fund in 2008, he goes, we can't use them anymore. Why? And he said, we need the big accounting firms. I said, why? And he goes, because when an institution three years from now flies from Boston to come see us, they're going to want to know who your auditors are. And you need to have the big four. And when you tell them one of the big four names, Deloitte and Touche, right, they're gonna go, okay, go the check box, check the box. If you tell them ab work. Yeah. If they do say ABC Company, it's all. I said, they're gonna go, what? You know, so he. And I said, but they're triple expense. He goes, exactly. John. We have to become a company worthy of an institution before the institution comes. We can't wait to them come out and say, oh, we'll change. No, no, that doesn't work that way. They're coming up. You. You already have to be. So we had to become things that we didn't want to be yet. We had to become a registered investment advisor. We had to become, we, we had to use the big four, right. We had to have SOC 2 type 1 audits before we were asked to do them. Right. So our vision was always, we're going bigger and better. And so. And once you get to that level, for instance, let's see, my first fund was 2004. We got our first institution in 2010. Six years to attract that institution to actually write us a check. But after you got that first one. Yeah, it was like, you get, it was like a snowball. It is, it's a long term plan. People want to go after institutions now. Listen, I've seen people, their first fund get an institution. I don't know how they did it. Probably relationships maybe, but it takes years and years of prepping your team, training your team, getting your team to act and talk like an institutional worthy investment.

[Podcast Host]

That's an interesting thing because I don't think most people understand how much you have to grow into your goals and businesses have to do that the same way humans do. So how did, did that strategy just be something natural to you or did you have to learn that? Where did that come up for you?

[John Pennington]

No, and that was one of my partners. He, he was, we hired, we hired him as an employee, as an operation officer. We said, you know, used to work at big, the big financial firms. Can you make us more institutionalized? Okay. And within a year he was a partner. Right? Because we couldn't, we couldn't let him go. We, we had to have him. And he convinced us we have to spend the money now, triple the audit cost to become. And that got us into that mode of spending the money now we have to, we have to keep our salaries low, spend the money now, invest in our company. Because this is, could be huge and I want to be huge. Right?

[Podcast Host]

Let's go back to the raising capital and average business owner where, where can they start learning the raise capital thing? Where does the. Because they're going to have to do it. And they're probably not getting debt money, you know, probably not getting debt.

[John Pennington]

If they can get debt money, you go get it because it's cheap. It's cheapest, right? It's cheapest. Investor money is more expensive. But there's no payment every month, right? Debt money you get, it's cheap, but you have a payment you got to make, right? So we, you know, most of our funds were, hey, we're going to get investor money, we're going to Pool 99 investors into one pool called a limited partnership. And we would file under a 506B 3C1. And that allows you 100 investor, 99 investors of accredited investors, 35 non accredited investors. Then above that, there's a 500A 3C7, and 3C7 allows you 2,000 investors. But they have to be qualified purchasers, all of them. A qualified purchaser, a quality purchaser, is someone who has a $5 million net worth. A qualified client is someone has $2.1 million net worth and an accredited investor has a million dollar net worth. Or now if you're in a lawyer, if you're a, if you have financial licenses, you can be a credit investor. And there's a couple of exceptions there. In a 506B3C1 you can have investors 35 can be non accredited. This is a fund structure. A lot of people, they're not large enough to become funds because funds are kind of expensive to get into the game. If you're going to raise and do big things. A lot of people are, you know, they want to raise $3 million, $6 million. They're not really big enough yet to be a fund. So they're kind of a limited liability company. But I would say when you write your limited liability company documents, you need to write them kind of like a fund where the passive investors don't vote every year to take the president out, right? So you have to kind of mirror fund documents. Because most funds out of New York and Boston are called 2 and 20s. They're 2% management fee, 20% of the profits. And I gotta tell you, when I learned in 1999, I was like, wait a minute. Real estate agents make 3%, okay? Stockbrokers make 1 1/2 percent. A mortgage broker makes 1%. A general partner makes 20% of the profits. I want to be one of those guys, right? I was like, you know, over, there's always a minimum. You have to make a minimum, like a prep for your, for investors. But over the minimum, if you hit the minimum, you get 20%. I was like, I'm in. That's, that's what I want to do.

[Podcast Host]

I want to stretch out listeners thinking just for a second, because you're right. Most people go the private placement memorandum, they only want to raise a small amount to run this one business. What if we stretch their thing and say, well, what would you have to do to need a fund? How many companies would you have to be buying? Because I don't think people realize that it's Cheaper to buy a company than start one. It's cheaper to buy a company than buy customers. Even, like, marketing is more expensive than buying a company. And the time to do it and buying a company is equity deployment, not expense deployment. And so when we look at that and it's like, what would you have to do to go, okay, how many do I need to buy in order for it to be worth doing a fund? I mean, I know when me and Doug came to you guys and started learning this stuff, we're like, holy, we need to start our own fund and go and buy a bunch of, you.

[John Pennington]

Know, okay, so my first fund, the fund documents, the legal documents cost me about 35, $30,000. Okay. So. And we were lending on real estate. Okay. So my third fund costs the same documents cost a quarter million dollars. Okay. Now, so, so you asking, well, how big would you have to be to have a quarter? So the, the third fund, we were raising money from Australia, from Hong Kong, from France. And so what you're doing is in one document, you're combining the IRS of Australia and New Zealand and the US and France and Hong Kong all in one document. And you're combining the SEC regulations and the SEC of Australia. That's an expensive document if you want to raise money for a real estate fund overseas at US Real estate fund. But the first fund, we weren't raising money internationally. We were raising money in five states and we were doing loans in five states. So it really comes down to, I think, the upfront costs. How big, big would the, would the capital raise have to be to justify a quarter million dollar piece of paper with a bunch of papers with ink on it? Right?

[Podcast Host]

Yeah.

[John Pennington]

And so that's kind of how you have to, you know, think, think, think about it. But my first fund with, with $30,000 of the upfront cost and then putting it into place, I personally, my partner, we had to go like 14 months without a paycheck. Yeah. Now we had two other guys, two friends of ours that wanted to become. They couldn't do it. They had lived their lives where, you know, they had car payments and house payments and second mortgages and stuff. But they were great guys. They just couldn't go 14 months, 15 months without a paycheck. And then the two of me and another guy could. So we did. And then after about that year, year and a half, we brought in two more partners. And those, those, those guys were the big boys in the real estate industry. And we were already cash flowing by that time. Right. And so I guess in the roundabout way, that's kind of what I'm saying. It's kind of like, how big is your room right now? Why could I go 14 months without a paycheck? The reason is I looked in the mirror when I was young and said, I don't want to be old and poor at the same time. So all my businesses, I was like, I have to. When I. When the years are good, I can't go buy a new car. I have to put that in the war chest because I might get a bad year. And that's why I said, when we finally hit in 2015, the 8 billion, I was like, I don't need a war chest anymore. I'm good. We're making so much money, I'm never going to. But all my 14 businesses, every time it was going good, the years, I just lived the same life. And a lot of people, and I think you coach this way, a lot of people, when they start making a lot of money, they start spending a lot of money. There's three different levels of wealth. Rich people, they view money, you give them money, you know what they think, how can this money make me more money? Now the middle class person, they get more money and they go, okay, this money can help me get a bigger house with a bigger payment. This money can help me. This salary can help me get a bigger car with a nicer car. That's how they think. And poor people think, this money can help me eat today so I can eat. That's one mentality. Middle mentality is, this money can get me more in debt, but I get to live a better life. And rich people are like, I just want this money to figure out how to make more money. That's the three different. So if you're in the middle and you're thinking, how can this money make me more money? That's how I thought I got this extra money. I'm making good money. Oh, I got to put this away. I got to save this. I got to invest this. I can't go buy another car. My boys tell me it's a great story too. My son, they'll tell us on stage. My sons are on stage a lot and they do presentations and they'll say, yeah, my dad, he was driving a car with 200,000 miles on a dent in the door, right? And he has my. One of his business partners agreed to be a mentor to one of my sons. So he goes up there, you know, to this guy's house, and he goes, I go through these private gates I drive through this beautiful rolling hills. I come to this cul de sac. There's a house, a white house. I knock on the door, I think there's gonna be a butler. Go away. You know, he walks, he goes, there's beautiful white couches. There's an indoor basketball court. There's an outdoor pool. There's a view off the deck of the whole valley. It's gorgeous, right? He's got sports cars in the. In the garage. And he says, he says, I want you to be my son's my son. He says, I want you to be my mentor. And he goes, let me tell you a secret. You know, rich families send their kids to Ivy League schools, then to Wall street, and they come home and run their family fund, right? The family office. And he goes, I know, that's why I'm here. I want you to teach me how to do funds. He goes, your dad knows more about funds than I do. We're partners, but he knows more about funds than I do. And he goes, but you're vastly more successful than my dad. I want you to teach me any. He goes, let me tell you a secret. Me and your dad make the exact same amount of money. And my son, he goes, I looked at the ceiling, I looked down and I said, I gotta go. And he drove home. I remember I was sitting in the living room watching football. It was a Saturday afternoon. And I heard the door slam. Bam. Dad, what is going on? And the next two months, I mean, I mean, so my wife got a new Range Rover. Yeah. I bought a Tesla. I bought my test, my dad a Tesla for his birthday. My dad, My kids got new cars. My father in law, mother got a new car. I spent like a half a million dollars the next month. Two months in cars, right? So the bag was out of the bag. I wish I could have stayed under the radar for about five more. Five more years. But he goes, my dad was. We're living a normal home. And he was 200,000 miles on a dent in the door. And my partner had sports cars and all this stuff, and it was. But anyway, that was years ago. So.

[Podcast Host]

Yeah, you know, it's really interesting is, you know, I remember, first time I filled my own bucket and, you know, I had all the things that were on my bucket list sort of thing, and the dream chart. And then it was like, maybe it's a bigger bucket. You know, instead of one nice car, let's get multiple. And maybe it's not just one nice house, it's two nice houses. And that Sort of stuff. And eventually, and I think that was a part of me being first time rich to, you know, that I don't know, wanting to look rich more than be rich type thing.

[John Pennington]

That's human nature, right?

[Podcast Host]

For me, I don't deny myself that stuff because I'd worked my tail off to do it. Nowadays though, I see doing these podcasts is more important and giving back and teaching others to me is more important than doing that stuff. But you know, it, I think we all have to get there. So let me just finish this up with one very simple question that's not that simple. All right. Person sitting on a million bucks a year now, or a million dollar a year business, what's the two or three mindset shifts they've got to make to go for the hundred million to go for the exponential and the scale?

[John Pennington]

So, yeah, so, you know, let's just say, let's just take a dentist, okay? They make really good money. They work three days a week after they got their business up. They're all four days and they work three days. I've seen this over and over, right? And they make a real, they have a really good life. So you're going to talk this person out of that really good life so they can have a generational wealth, okay? They have plenty of money for them and their family. And so that's a, you know, a kind of a decision the person needs to kind of make because they're going to have to risk, you know, they're going to have to risk a lot to go big. So would that dentist decide, you know, what I'm going to do? I'm going to drill teeth three days a week and two and a half days a week that I used to not work. I'm going to try to build a fund or investors and go buy more dental offices. And in 16 years from now, I'm going to have 45 dental offices, all working in these five states. And then I'm going to retire because I wanted to go big and I think it's a personal thing. These people have worked hard. They have a great life. Who's going to talk about the great life? There are some people though, and I was when I was 40. Just once in my life I want to go for it all. I want to go large. I don't want to start a business and make it work. I want to go for and see if I can, what, what can I do in this life? And so I don't know how you would talk. I think it's Just a mental desire in someone that just wants to try to go big once in their life. And that dentist has the ability, he has the time and the money to do it. If he learns how to raise capital, investors and how to duplicate himself, which you can do 16 years from now, you could have 45 dental locations and you could be generationally wealthy. Not just wealthy. Right. So I. That's kind of the roundabout. So I don't know how to answer that, except for I got to find the right person who really believes and wants to try it once. Now they might fail at it. This is the problem. This is the problem. And the great thing, you get to fail at stuff. Right. Can you imagine you lived in a life where nothing, you couldn't fail anything. It'd be boring. Right. And. But, you know, say it'd be safe but boring. But. So I, I don't know how to, yes, properly answer your question, but that's.

[Podcast Host]

The old saying of if you knew you were going to succeed.

[John Pennington]

Yeah.

[Podcast Host]

What would you start? And I think that, you know, very bluntly, most dreams die on the never started list rather than on the actually failed list. So. John Pennington, thank you. $100 million. Let's go. Thanks for joining me on the $100 million podcast. If you've got value from today's episode, make sure you've subscribed and check. Share this with all of your friends. Never miss a strategy that could change your business and your life. And remember, the fastest way to scale is to learn from those who've done it. That's what this show is all about. See you on the next episode.