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09 April 2025200 min

How to Invest After Selling a Business (Without Losing It All)

with Ben Fraser, Aspen Funds

You built the business. You cashed out. Now what?

Most founders think they need to “reinvest everything” or go chase the next big thing. But in this episode of Beyond 8 Figures, I sit down with Ben Fraser of Aspen Funds to break down how to invest after selling a business — the right way.

Ben’s been inside this game since the last recession. He watched his father build Aspen Funds from scratch after the 2008 crash, and he’s since helped scale it into a multi-million-dollar platform that helps entrepreneurs invest passively (and intelligently).

We talk about why entrepreneurs make terrible investors, how billionaires actually diversify, and the overlooked tax strategy that could save you six figures. If you’re still betting everything on your business — or worse, sitting on cash and hoping for the best — this episode will shift your mindset.

Key Takeaways & Timestamps:

  • [05:37] The One-Liner That Changes Everything – “Wealth is created through concentration, but preserved through diversification.”
  • [06:38] How Billionaires Really Diversify – Ben reveals the Tiger 21 portfolio breakdown and how to use it.
  • [14:35] Unlocking Tax Loopholes Most Entrepreneurs Miss – What happens when your spouse qualifies as a real estate professional.
  • [15:36] Why One Founder Quit a 6-Figure Job to Save More – Ben shares a story that’ll make you rethink W-2s.
  • [19:47] Where the Smart Money Is Moving in 2025 – Ben’s macro-driven view of real estate (and what KKR just did).

Ben Fraser is the Chief Investment Officer at Aspen Funds and co-host of the Invest Like a Billionaire podcast, where he helps high-performing entrepreneurs grow and protect their wealth through smarter, passive investments. With a background in commercial lending and institutional asset management, Ben has overseen $125M+ in real estate and business loans. Today, he specializes in guiding business owners toward alternative investment strategies that prioritize stability, cash flow, and long-term growth—without adding complexity to their lives.

The next big move in your business might start with a conversation.

If you’ve been thinking about leveling up, shifting directions, or preparing for a future exit, A.J. offers strategic support for entrepreneurs at a crossroads. No pitch—just a chance to explore what’s possible.

Key Quotes:

  • “Wealth is created through concentration. But it’s preserved through diversification.”
  • “Entrepreneurs make terrible investors… because we’re wired to take risk, not preserve what we’ve built.
  • “You don’t need to earn more. You need to invest smarter.”

Episode highlights:

  • Don’t just reinvest everything into your business — you’re exposed.
  • Real diversification starts when you stop chasing control.
  • Use tax law to your advantage (especially with a strategic spouse).
  • Billionaires don’t try to time the market — they plan across decades.
Connect with Ben Fraser:

Transcript

[Intro]

A.J. Lawrence:
Hey everyone. Welcome back to another episode. Please, as my team keeps reminding me, if you’re enjoying the show, please go to the website and sign up for our newsletter. That way, whenever we have another cool guest like today’s guest, and when we dive into a really cool subject that I think a lot of entrepreneurs would like to learn more about, you’ll be the first to know. So please go to beyond8figures.com and sign up for our newsletter. So today we have Ben Fraser on the show and I’ve been going through a lot of your material, going through your podcast going on and stuff. And I’m really excited to kind of get in because Aspen Fund, I’ve been looking at, as an entrepreneur, how to invest my money that I’m making both from after sales I’ve had from business, but also just like on the ongoing basis of running my business. And everyone keeps talking about real estate, real estate, real estate. But every time I’ve tried to look at my own properties or stuff, I’m like, all right, there’s a lot of work and a lot of complexity. And while that’s all good and I know there’s a lot of profits to be made, I’m a little more worried about building my own agency here, my own company, rather than adding additional complexity in my life. So I’m excited to kind of dive into this. Ben, thank you so much for coming on the show.

Ben Fraser:
Thanks for having me, A.J. Looking forward to chatting.

A.J. Lawrence:
What was your journey kind of getting into real estate and into Aspen Funds?

Ben Fraser:
So it’s kind of a meandering journey. And it’s interesting because I think we were talking about before the show, a lot of people I think get into real estate because of the sexy factor or the allure of building millions of dollars with buying a few properties or whatever. I never really had the itch, so to speak. It kind of ended up in this space, but have now been in real estate for nearly a decade, is something I’ve fallen in love with. But starting out I was definitely more on the finance side. I’ve always loved numbers. Most of my career kind of early on was spent in commercial banking. So I was an underwriter, a commercial banker for many years before having the opportunity to jump into the private equity side of things with Aspen. And so one of the cool things which a lot of people don’t know is my father was one of the founders of Aspen. He started at about 12 years ago, I joined about seven years ago. That’s been a pretty fun thing as well to grow a business that when he started it, it was kind of hey, there’s an opportunity here in the market coming out of the great financial crisis. He actually was a tech entrepreneur and so probably relates to a lot of your listeners. Saw really opportunity to take advantage of what the market was doing but then really became much bigger opportunity than just a one off kind of deal. And so it’s been fun to scale that together with some other partners. A lot of your questions I can resonate with, right? Cause I have the same conversations with a lot of people that are in that same boat. And honestly a lot of our clients are entrepreneurs because it actually fits a really good balance of you’re really good at making money. And what I find a lot of times for entrepreneurs is you take extreme levels of risk, concentration of risk, right in one business. And the success or failure of that business basically determines if you’re going to go bankrupt, if you’re going to be a multimillionaire. And you have to take that type of risk many times to achieve the level of success that a lot of entrepreneurs do. The challenge with that is from a preservation standpoint of wealth taking that same level of risk, you have to kind of shift your mentality a little bit. And it’s funny because I actually had a-one of our guests on our show a little while back was Michael Sonnenfeldt. He’s the founder of Tiger 21, which is this kind of global group of ultra wealthy, high net worth investors. Most entrepreneurs and you know, they have to have I think it’s 20 million liquid or something to join the group. So pretty significant success. One of his comments, he says entrepreneurs make terrible investors because the risk tolerance is skewed from what should be normal for an investment approach. All that to say, it’s been interesting. There’s a lot of benefits of investing in real estate and there’s a lot of ways you can do it where you don’t have to be the landlord yourself. I think that’s for a lot of people get stuck, myself included. I don’t want to be a landlord, but there’s a lot of benefits and ways to do it. You don’t have to be.

A.J. Lawrence:
I forgot to mention to the audience, you have your own podcast, Think Like Millionaire. You have amazing guests. Had some similar guests like Walker Deibel and a few other people. Back to that point, I agree. We do make bad investors. Either I know people, some really successful entrepreneurs who’ve built these amazing super companies and they’re like the most basic, simple, like just give me safety. And then I know people maybe like myself who maybe went through the late knots or the late teens with a lot of ICOs and other stupid crypto stuff where it’s like, okay, I made money, but wow, did I really? Just pure luck, whatever I made. How do you discuss with entrepreneurs, real estate investments, how does that fit into their overall sort of approach to investing?

Ben Fraser:
Yeah. I mean, I think in a broader conversation around investing in general real estate, I view as one component of it. And one idiom that I always love to go back to is wealth is created through concentration, but it’s preserved through diversification. So it’s the idea, we’re just talking about where to create wealth. Many times you have to get very concentrated. You focus on one thing and you do that better than anybody. And that creates the value which creates wealth. But then to preserve it, you can’t-if you go exit a business, you have 20 million bucks liquid now you can’t go invest that all into a preseed startup and that would be a good financial plan. Right? And so whether you have exited a business or not, I think it’s important to take chips off the table. Even if you have an exit, you’re making money now as an entrepreneur, you don’t want to sell in the short term. I think taking chips off the table instead of reinvesting everything back into the business, start to create some diversified investments and income streams and build some of that external stability to help. Because it’s unknown what happens to whatever industry you’re in or the business transaction marketplace in general. To your specific question on real estate, I’m a proponent where a lot of people in the real estate space might say real estate or bust, all or nothing, stock market bad. From my study and our show is called Invest like a Billionaire like you mentioned. And the goal is to emulate what the ultra wealthy, the multi-generational family wealth, the billionaires, the endowments, the foundations, high level investors, what are they doing? And from my study, what most do is have a pretty balanced portfolio, right? Tiger 21 is a great example. They published their data quarterly on average across their several thousand members. About 25% have investments in stocks of their portfolio, another 25% in private equity. So that would be businesses either they own and run and or invest passively. And then the other 25% is in real estate and then kind of the rest, the other 25% is just a smattering of lots of different things like commodities, crypto, cash, et cetera, et cetera, et cetera. But those kind of three make up a core part of most portfolios. And so I view real estate as not the end all, be all. But there’s some significant advantages to real estate investing that you can get even as a passive investor. Meaning, you don’t have to actually be the landlord that owns the single family rentals or the Airbnbs or the multifamily apartments. You can get a lot of those benefits that real estate investors tout while still being a passive investor. And so I think that’s one big reason. The other is lack of volatility. In the private markets you can generally get higher risk adjusted returns if you do it right than the rollercoaster of the stock market.

A.J. Lawrence:
I was mentioning sort of the overhead of the mental and not understanding and looking at real estate, not knowing quite what to do, having to start in learn all this. What are sort of the trade offs of looking at something like Aspen Funds versus doing it yourselves? Are there tax efficiency benefits that change between the two? What are you looking at between the difference besides the learning curve of having to do it yourself?

Ben Fraser:
I don’t think one’s necessarily better than the other. It’s what do you value, right? Do you value control? And I think a lot of entrepreneurs struggle with that, where they want to control everything. And there’s a certain degree of where control is important. But I also think there’s value in leveraging experts that are good at something that would take a long time for you to become an expert at, leveraging other people’s expertise. If you go become a direct owner of real estate where you go buy an apartment building or something, that necessitates a pretty big learning curve amount of time you’re now responsible for, those midnight calls when the furnaces go out or there’s a flood or whatever. And so I think you are trading for that control. You’re trading kind of time, energy, big learning curve where I think you can leverage other people’s expertise in an area and you can spread out your cash amongst several different operators, investors, investment firms, asset classes, geographies. You can actually create a pretty diversified portfolio with not a whole lot and you are reducing some of those idiosyncratic risks pretty substantially very quickly. And you don’t have to get the dirt under your fingernails right? For me, which is funny, being in real estate, I don’t like being a landlord. I have teams that manage all that. I manage it from a high level, but I’m not getting any calls and I don’t ever want to take my own cash personally and go buy my own properties because that’s just not my strength. I’m not handy. I don’t want to get those calls as a landlord. I want to leverage it through the teams, the systems, the platforms that we have and expertise of other people in those areas to benefit me. Now from a tax standpoint, we could talk about pros and cons there, but at a high level that’s what I think about. There’s trade offs in everything. If you don’t want to give up control, well then you’re by default going to be taking on more stress. Things you have to manage that you wouldn’t have to if you leverage other people.

A.J. Lawrence:
It’s the same as running a business. If you really just want to be involved in business, you can buy equity, you can buy stocks and done. But other than that, you take on the additional risk and the additional potential from that. Let’s just talk about investing in a fund because I think there’s a lot of people that talk about the tax benefits of real estate from personal investment. But like are there tax benefits from investing in like an Aspen Funds for an entrepreneur?

Ben Fraser:
Yeah, sure. So at a high level, there’s kind of two big fancy words that we use in the private markets here. We have syndications and we have funds. So a lot of people might be familiar with those terms, if they’re not, most of the time what you see are syndications. So basically a sponsor group, an investment firm is raising money to go purchase a single asset and do some type of business plan to improve the value of it. And they have some type of planned exit that which they can realize that value. That’s what’s most common. The difference between a fund and a syndication is a syndication is a single asset. A fund generally is a pool of a variety of assets. And so that can be, I mean really whatever you want. You have multi-asset class funds, they target different asset classes. You can have single asset class funds, funds focus on different geographies, different strategies. So the world is wide open as far as that goes. But at a high level, syndication versus a fund, all that means is the number of assets within it. In a fund you have different types of funds. You have kind of a closed end fund, open end fund. We manage both. What we do right now predominantly is our open end funds. And so these are funds that have existing assets in them. And then investors can invest into those funds to get direct ownership, pro rata of those particular assets. And then we’re generally adding assets to the funds over time to continue to grow it, diversify the income base, geographic risk, et cetera. As far as tax benefits go, the great thing with a lot of these private market investments, whether it be a syndication or a fund, is you do get the direct tax benefits. And whether it’s a fund or syndication, it doesn’t really change that. And basically the losses that are generated at the asset level, whether they’re true losses, because you’re improving a property and you’re spending a lot of capex and that’s creating a loss, or their paper losses because of depreciation, which the IRS graciously grants to owners of real estate. Those can be passed directly on to all the owners of those funds or syndications. And then as investors you can use that against, if you’re not a real estate professional, which we could talk about, but most people aren’t, you can use those against other passive gains that you have from other investments and that can offset potentially those gains to reduce or defer your taxes.

A.J. Lawrence:
So that’s being able to write off against, how about just like business income? You hear a lot like, oh, if you have income in your business, you do this and you write off. If you’re doing it this way, it’s only for other investments.

Ben Fraser:
Exactly. So that is where the tax code kind of creates some limitations. This was, I think, a very relevant discussion talking about real estate professional status because you mentioned off air, we had a friend that did this and it seems complicated, but it’s not terribly complicated. Usually the trade off and benefit is insanely positive and I’ll give you some examples. But before we go there, if you are just investing, say you’re a business owner, you’re doing that your primary occupation, you’re investing cash into some type of real estate investment, you get some losses. A lot of times you can accelerate depreciation, you can squeeze more depreciation on the front end of the investment and that can offset other passive income. So if you have say a gain where another investment of yours sells in a given year and they’re in the same calendar year, the losses from that one investment can actually offset the tax liability from the one that just sold. Right? So there is some benefit there. It doesn’t flow through to your business income. So you have limitations on how much that impacts or how much of those losses you can take. The good thing is they do carry forward. Meaning if you can’t use all the losses in that given year, they carry forward until you can use them, they don’t go away. But here’s where it gets really, really interesting where I’ve seen several people do this, it’s been pretty significant where if you are married and you file your taxes jointly, only one of the spouses need to be a real estate professional, which is a qualification designated through the IRS. And basically what that means is that individual spends most of their time on real estate activities. And I think the break even point is 750 hours in a year. So it’s about 20 hours a week. And it has to be the main thing they’re doing now. There’s a lot of ways you can kind of not game the system so to speak, because you do have to actually do the work. But there’s a lot of hacks you can do where I actually this would, in my opinion, be a reason to get some type of rental, either single family, potentially even a short term rental that you manage as a vacation home. And what happens is if you can meet the qualifications, all of a sudden all those losses that are kind of locked up to only be used against passive gains or passive income basically get unlocked to be used against any income, business income, W2 income. It basically opens up the whole thing. So I had a friend whose wife was an entrepreneur that run a very successful bridal shop. He was working full time a job he loved, but they actually ran the math and he was pretty high salaried guy, kind of mid upper level management. And based on some of the investments they had made, it made more sense for them for him to quit his job entirely and work a few hours a week on some of their rentals where they’re actually going to take home more income by him actually leaving his job to do this. That’s a reality for a lot of people. Now, some spouses don’t want to do that. That’s totally fine and there’s still some benefits but I want to make that point because there’s a lot of people in that kind of world that this could be massively transformational for.

A.J. Lawrence:
I think just like running a good business, a lot of times we all have goals and we all have desires, but until you actually do the math and figure out what the pathway is, you have to understand it before you actually do it. Like, let’s see what this is. So I like this idea of like, hey, look at this. You have these investments, you have this cash flow, look at the benefit, the trade offs, you have this. There is the risk adjustment and then this actual taxing depending upon what you’re doing. That’s a great way of thinking about it. What I wanted to go back to, and I know this is in the market 24/7. We just came through a period where everyone is waiting. I’m a New Yorker, even though I don’t live in New York City anymore, where it’s like 30, 40% on occupancy, commercial real estate, specifically office space, is way underutilized. Everyone’s waiting for the shoe to drop. When you’re looking at real estate, is it now a good time to go in? Is it just a fund? What are you looking at when you’re looking at this sort of economy and what we’re looking at in real estate? Housing prices are still going up, but there’s not as much sales because of the interest rates. What are you seeing and how does that impact as someone looks to invest here?

Ben Fraser:
Great question. And you know, to take one little quick step back because our two founders, one of them who is my father and the other is Jim Maffuccio, one of our partners, they’ve both been through multiple cycles. They’re both got the gray hairs, got a lot of battle scars through investment cycles. And Jim, he was a real estate developer through the heyday of the early 2000s in California and went through a pretty brutal reset with the great recession that we had in 08-09. And then my father, like I mentioned, he was a tech entrepreneur and very, very successful tech company, had 300 employees, won E&Y Entrepreneur of the Year award in 2000, about to go IPO. And then the tech bubble burst and he had lost control of the board in his last round of fundraising. And they said, hey, we’re going to liquidate the whole company because the internet’s a scam and it’s all worthless. So the point is there’s cycles, right? And there’s economic cycles and there’s business cycles. And intuitively, as entrepreneurs, we’ll get this right where there’s better times to be in certain places than others. And what’s really kind of at the foundation of how we operate and where we look for opportunities is what we kind of call macro first. So we call macro driven alternative investments. Because what we believe is that understanding the macro picture. The bigger term trends that are going on are way more important on identifying your investment strategy than the actual deal itself. Now the deal is very, very important but if you got a good deal in a bad market, it doesn’t matter how good that deal is. It’s capped at how valuable it can be, right? But conversely, if you have a pretty good deal in a growing market, the rising tide lifts all boats. And so there’s, from our standpoint, the kind of top down first analysis is really, really important to understand where is the best opportunity right now? Because as you’re mentioning, we’ve had some seismic shifts in the world with interest rates going up and with all the stimulus that’s been printed and some pretty big roadblocks and challenges ahead for several asset classes in commercial real estate. So to get to your question, the opportunity set is it’s not one simple answer, but at a high level, office is in my opinion still a knife that’s falling and we don’t know where that’s going to land. I think there’s been a fundamental shift post Covid that I think was already in play. This hybrid work, this remote work that was already moving.

A.J. Lawrence:
Was already global, 10 plus years.

Ben Fraser:
Yeah. But Covid just accelerated it and then just everything changed overnight. I think how employers think about their workforce and building teams has really changed a lot. And then it’s interesting because a lot of office space, at least class A office space, is economically the economic occupancy, which means how many signed leases they have is still pretty high. But physical occupancy, which means how many bodies are actually in the buildings, is very, very low. And so there’s this kind of disconnect and part of it is the way that leases are signing off. It’s usually on a seven to ten year cycle. So a lot of these company signed leases a few years ago. To me, the big shift will happen in office probably over the next four to five years. We’ll start to see how that plays out as these leases start coming due and firms may or may not renew. Or maybe they might consolidate some of their space. So all that to say that’s one example where people talk about commercial real estate’s in trouble. And what most people mean is office and I would agree offices is challenged because hey, if you got a 50% drop in occupancy and you have a 5x increase in your debt service cost because of interest rates, those numbers don’t work very well and it’s hard to know where that lands. Now as far as other asset classes, we talk a lot about in our podcast these kind of macro trends going on and one of them that’s happened is in housing, right? So housing is probably the largest asset class in real estate, probably behind office, specifically multifamily. It’s had a really unique kind of mini cycle, so to speak. There’s been a, three plus years ago, a huge development boom with interest rates so, so low. Really supply being pretty constrained. For a long time it’s been an under supply of housing. It causes huge development boom, especially in kind of the Sun Belt markets where a lot of the population growth has migrated to. Now what’s happened is a lot of those deals were either purchased with bridge debt, existing properties and then the new developments are now hitting the market. So what’s happened is it’s created this actually supply glut where there’s a huge amount of supply that’s hitting the market. You know, meanwhile you have higher operating costs with insurance going through the roof. You have interest carry costs going through the roof with interest rates going up. And so there’s been a lot of turmoil within multifamily. Now we’ve already kind of seen prices start to reset about 20 to 25% in multifamily. The problem is that most sellers don’t want to sell because they don’t want to realize a loss. They’re kind of hoping they can ride it out till the kind of rebound of the cycle. The challenge is going to be there a lot of distressed sellers and a lot of distress situations because like I mentioned, a lot of these properties were purchased with bridge debt. And how bridge debt works is one, they’re floating rate interest rates. So they are getting hit really hard with the interest rates. And two, they usually have a three year term and then they have to either refinance, get new debt or they have to sell. And right now, by a lot of estimates, somewhere between 25 to 40% of current deals are personal in the last few years, are not cash flowing and would not meet qualifications to refinance. So what does that mean? Either lenders are going to what we call extend and pretend they’re going to just extend the loan, kind of kick the can down the road and hope the problem gets solved, or they’re going to start foreclosure. And I think that will potentially create a really interesting buying opportunity. Now one more little aside here. This might be getting too much in the weeds for you but there is a massive amount of capital sitting on the sidelines that’s waiting for these deals. And so the question is, well, I’m just going to sit back and wait for the next big buying opportunity like we had in post 08-09. The challenge is because there’s so much liquidity in the system, I think the actual deals are going to happen inked up before they even get too far into the system and into the kind of retail investors inbox And I mean we just saw an example on Wall Street Journal. KKR just purchased, I think it was 20,000 units, multifamily units, $2.1 billion, making a pretty big kind of move into this space. And they purchased it at pretty insane values. Still, they’re buying it yesterday’s prices and their whole thesis is long term they’re still under supply. We can be long term holders. So we’re willing to kind of come in and maybe it’s not the bottom of the market, but it’s definitely been an adjustment and long term are going to be rewarded for that. I do think there is a good time right now. I think we’ll even have a better time over the next 12 months because prices are resetting and all of a sudden as prices are resetting, all the numbers look good again. Right? And then as we kind of come out of this interest rate cycle, that will improve values, it’ll improve activity, it will help beneficiaries of real estate owners. So a little more into the weeds maybe than you wanted but I think there is opportunity right now in real estate and it’s office, I would say not looking there, there’s definitely some opportunities.

A.J. Lawrence:
Yeah, it’s funny, I think it lends to what you were saying earlier as a risk diversification. I remember being in New York and New York was a very small tech scene back in the day. It’s getting bigger and bigger and becoming more. But back in the early knots, I had a lot of friends in real estate and I knew older people who had gone through a few cycles and they were complaining. You were talking about all the investment opportunities after 2008-09, and they were complaining that it was nothing like the savings and loan debacle. They had said, oh my God, you could just like shoot fish in a barrel. We were buying stuff, pennies on the dollar, here we are. And yet because of the amount of capital in the market and like you’re saying, the realization that macroly you’re looking at something long term, this is still going to be needed. I think there’s less of that blood in the water. As an entrepreneur, this is not a get rich quick, this is a diversification long play. Each cycle seems to be less, maybe more of a blow up, but at the same time there’s less of that quick money approach to it as each cycle goes through.

Ben Fraser:
I think it’s funny too because a lot of times hindsight’s 20-20. And so it’s like, oh man, I just wish I would have bought so much more real estate come out of the great financial crisis. But at that point no one wanted to buy it because it was not the darling anymore. And same thing with tech stocks back in 2001, 2002. The challenge as an investor is the good buying opportunities. You usually have to be somewhat contrarian. And it’s difficult to be contrarian when everyone else is saying something else. Now I don’t think we’re going to have as deep of a recession as we’ve had before. I do think it’s going to be a slower kind of bleed out because of all the stimulus has been pumped into the economy and how lenders are really not wanting to pull the trigger quickly in foreclosure, which can create a domino effect like we’ve had in past crises. So I do think it’s going to be almost a slower bleed out. But I do think over the next 12 months it’s going to be be good times to be picking up positions in these types of investments. What we’re doing right now is really interesting is we’re kind of playing what’s called a kind of preferred equity play in a lot of these deals. Where we see opportunity is we can come in because right now it’s really hard to raise equity because a lot of investors are spooked. And then conversely, the lenders are very reticent to lend because for two reasons. One, they’re very risk averse and two, all these loans that they were expecting to pay off, they’re not paying off because they’re extending them and they’re kind of kicking the can down the road. And so that’s reducing their ability to actually lend new capital because they rely on those payoffs to fund new loans. So there’s a pretty big gap where a lot of good deals that are new deals being purchased right now need more capital. And we’re kind of coming in where we sit, what we call the middle of the capital stack so we’re behind the senior lender, but we’re in priority to all the common equity. And so we can come in with pretty attractive rates of return for our investors. We have capital protection where our capital has to get paid back first before all the common equity. And we also have control rights to where we can take over deals if needed to protect our position. We have we think a great opportunity right now over the next several years to kind of come in because there’s a pretty big gap in the market for capital. We can, what we believe, achieve pretty high risk adjusted returns by doing that.

A.J. Lawrence:
Let’s go out a little further. Let’s say someone is looking at about 10, 20, 30 years now, 20, 25, we’ll keep it to that because that’s like the typical entrepreneur. How are you looking at the space? You’re seeing positivity over the next year for acquisition, then benefit over the next seven as you said, how are you looking at it let’s say 10 and then 20 years from now?

Ben Fraser:
Like I said before, real estate’s probably the core part of our investment portfolio we have right now. We also are very bullish on oil and gas. So we have quite a significant oil and gas holdings. Very bullish there for different reasons, but at a high level I think one, there’s a huge, pretty big significant movement of capital coming from we call Wall street to Main street where it’s investment capital is on average being moved from public markets to private markets. And I think private markets are going to become more developed. There’s a lot of new technologies, new platforms that are creating more transparency, more liquidity. So I think there’s going to be a huge continual movement towards investment in private markets. I think that’s going to be really investment in real estate, oil and gas, other types of private equity type business strategies for real estate specifically. I think the great thing with real estate is it’s proven over the past hundred years to be probably the most highly correlated asset class to inflation of any other asset class. And if you think about like right now, it’s challenging because interest rates being higher. There’s kind of an inverse correlation with interest rates to value. So higher interest rates reduce the value, but the interest rates are higher because we have higher inflation. And higher inflation, on average, over the long term massively benefits real estate owners. And so from my position, we have these kind of cycles, these ebbs and flows. And if I believe inflation is going to be higher for longer, which I do and we could talk about that if you want, but I think it’s going to be a massive benefit to owners of real estate owners of really assets in general, any kind of asset. Inflation is generally going to inflate values over time. You know, I look out five years from now, 10 years from now, 20 years from now, I think the opportunity set will be different. Because that will kind of go in short cycles. But I do think at a high level, assets are going to be much more valuable than they are today.

A.J. Lawrence:
Yeah, durable. I could see that very much. I agree. We’re looking at an approach that is going to be inflationary just with a tax policy. There’s going to be an aggressive tax policy. I think we can almost place, what did I see the odds at 70% Trump. It’s just some insane thing. It’s like, okay, the vote base won’t change that much, but the little bit that did change from last week, 3 to 5%, just probably permanently changed, which is going to lead to that. So, yeah, I think you’re right. Looking at this, it’s like, all right, what does that do? I think it gives us a nice stimulus, but then we’re going to have to pay for this. And that’s where real estate could be pretty good because there is limited. And no matter what, people are always going to need places to live. Well, usually I ask how people define their personal success from their business. You have four young children, what are you looking at as sort of your way of preparing them for the long term?

Ben Fraser:
Great question. I think legacy’s already on my mind. I got young kids, my oldest is only 11. I want them to be set up. And I don’t want to just give handouts. I don’t want to create entitled kids. And I think that’s the challenge of any entrepreneur or anyone that’s had success more than maybe they grew up with. It’s hard not to create entitled kids. And so I think we’re very intentional with it. I’m always trying to have conversations about teaching them about money principles, teaching them about investing, and I’ll go around and show them some of the properties that we own and say here, how’s this work? These people pay us money and that money pays back the bank and then whatever’s left over, we can kind of reinvest other things. And so always having them understand money principles. There’s a fixed amount that you can’t just spend whatever you want. You have to earn it. You have to create value. And I think for me, I want to create value added citizen. I want to create givers, people that are going to contribute to the economy, not just take from the economy. And I think the more that we can do that for the next generation, that’s going to sustain, create a great legacy for our country as well. Because if I think out really long term, there’s some pretty challenging demographic trends that really globally are in front of us. America is probably the most well positioned of any, but we still have some pretty big challenges in front of us. With the baby boomer generation retiring, even the next generation retiring after that, and the amount of just entitlement mentality that I’m seeing of younger generations to where we’re headed if things don’t course correct pretty significantly, we’re headed for some very challenging realizations here. So I’m hoping my kids will be contrarians in that regard.

A.J. Lawrence:
At least contributors, not utilizers. It’s an interesting looking at this, but also looking at technological. AI can do all sorts of things, can create a living space. But everything around it, we’re looking at global population of educated, trained people are dropping significantly. Different parts of the world are growing in population while others are shrinking. Environmental issues, wherever you land on that, there are changes happening short term or permanent. So trying to grow your children so they’re adapting and contributing to the change, I think is a cool way of approaching it.

Ben Fraser:
Absolutely.

A.J. Lawrence:
Ben, how can people learn more about Aspen Funds and then whether it’s a good investment or how to approach it as looking at investment for themselves?

Ben Fraser:
Yeah. Feel free. You can check out our website, it’s Aspen Funds. We also have our podcast, which you mentioned, Invest like a Billionaire, and our goal is really to help people become better investors. So we bring on a lot of different experts from different realms to help people. Because to me the biggest gap is education. And I’m not a financial advisor. I can’t give advice. And so if you come and say, hey, which should I do? I can’t actually tell you. You have to make that decision for yourself. We try and give you all the information to help you make that decision. But I think it’s really important as entrepreneurs, as investors in general, to level up your education, right? And I think one thing I always say on my podcast, I find so many people spend so much time from going to school, getting an education, building a business to create wealth, to make money, and they spend almost no time learning how to grow that money, preserve that money, invest that money, and they just hand it off to some other person that a lot of times doesn’t have their best interest in mind. And so I’m seeing a huge rise of what I’ll call DIY investors-of people that want to take more control back of their money. They’re realizing, hey, I spent a lot of hard time earning this money, I want to make it work for me. I’m not a dummy. Right? And it’s not that complicated. There’s some basic things you got to learn and experience is a great teacher as well. But it’s important, I think, just from a mindset standpoint to take a higher level of control in your investment decisions of how you’re building a portfolio, of how you’re going to grow and preserve. And so those are things we’re trying to do on our podcast is help people feel confident to take that control.

A.J. Lawrence:
Yeah, I think that’s a wonderful kind of approach of figuring out how to do it yourself. As I’ve gone through looking after I sold my last company to like the private banker situation was like after a while you’re realizing, all right, 1% for below market return on really expensive funds and everything. I was like, wait, I’m getting screwed left, right and center. I’m just a revenue source versus even a simple diversification and self-run. But I do like the approach of looking at, yes, you gotta diverse and you gotta find the right great partners. And I think that’s the interesting part. It’s like, look, there’s so much you can do yourself. There are ways of doing this that aren’t going to make you a revenue source while finding diversification in the market. Well, Ben, I really do appreciate you coming on the show today. This was a lot of fun.

Ben Fraser:
I agree. This is great. Thanks for having me on.

A.J. Lawrence:
Hey everyone. Make sure you go check out Ben’s show, Invest like a Billionaire. It’s on all the cool podcast hosting platforms. I think you’ll learn a lot. And like I said earlier, there’s a lot of cool people on there. Thank you so much for listening today, I really appreciate it and I’ll talk with you soon. Goodbye everyone.

Beyond 8 Figures
How to Invest After Selling a Business (Without Losing It All) with Ben Fraser of Aspen Funds
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      Seamless Process Automation for Smarter Business Growth With Neeti Mehta Shukla, Automation Anywhere

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      30:29

      What if Your Business Was Your Joy Box? With Amy Ransdell, REVA Global

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      42:22

      Your Business Needs You To Go On Vacation with A.J. Lawrence, Beyond 8 Figures

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      30:49

      What Does It Mean to Build an Intention-led Business with A.J. Lawrence, Beyond 8 Figures

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      52:11

      Establishing Financial Well-Being as an Entrepreneur with Henry Daas, FQ: Financial Intelligence

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      1:06:09

      Building A Stronger Business By Doing Less With Pete Martin, AskMyBoard

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      41:46

      Building a First to Market Business with Marcello Leone, Bevcanna

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      44:50

      Turning Leads into Customers with Shaun Clark, High Level

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      53:09

      Hack Business Growth By Building a Product You Would Use with Jeff Epstein, Onboard.io

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      38:50

      How Being Flexible Can Trigger Business Growth with A.J. Lawrence

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      49:24

      Building a People-First Company with Natalie Nagele, Wildbit

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      46:54

      Ending Poverty Through Entrepreneurship with Dr. Velma Trayham, Thinkzilla

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      26:27

      Build a Better Business Using Psychology with Aaron Hurst, Imperative

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      40:42

      What Does the Future of Work Look Like with Stephanie Nadi Olson

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      44:25

      Making the Most of Your Entrepreneurial Journey with A.J. Lawrence

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      30:13

      Sell More While Spending Less Through Channels with Stewart Townsend

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      1:05:26

      This episode is about YOU (a 5-minute update)

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      6:11

      Make Acquisition A Part Of Your Strategy with Walker Deibel

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      38:27

      Why Outsourcing Work Will Help Grow Your Business with Kevin Ashcroft

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      43:13

      How To 7X Your Business’ Value with John Warrillow

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      35:29

      Build an Exit Strategy Mindset Today with Mac Lackey

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      40:07

      The Rise of Acquisition Entrepreneurship with Parham Parastaran

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      57:27

      Gaining Clarity as an Entrepreneur with Matthew Korban

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      59:38

      How to Delegate Work and Hire Effectively with Nathan Hirsch

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      40:03

      How to Have a Happy Life as an Entrepreneur with Will Moore

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      44:02

      Creating Owner Independence with David Finkel

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      1:08:13

      Creating an 8-figure Business in the Renewable Energy Industry with Marek Zmyslowski

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      1:19:06

      How to Grow and Scale Your Business with Chris Guerriero

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      1:17:03

      Share What You Know With the World with Mitch Russo

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      58:19

      It Starts Inside You with Adam Hergenrother

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      1:13:19

      Experience Outweighs Enthusiasm Every Time with Steven Sashen, Xero Shoes

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      1:33:13

      Get a Clear Picture of What You Actually Do with Jonny Cooper

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      35:41

      Use Consumer Accessibility to Your Advantage with David Schottenstein

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      35:40

      Scale Your Business by Knowing the “Why” with Diane Prince

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      52:39

      Our Vision For Beyond 8 Figures

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      30:11

      We Bought B8F!

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      31:01

      8 Figures with Matthew Korban from protecting his house with a rifle in Lebanon to an award winning business

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      27:24

      $321 Million Dollar Exit From Restaurant Delivery, Will Moore CEO of Moore Momentum

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      59:52

      $300M+ Houston Curtis, The Billion Dollar Hollywood Heist

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      1:08:39

      $100 Million Business | Marek Zmyslowski, Investing in Africa

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      59:13

      $10M+ | Mac Lackey Started, Scaled & Sold 6 Businesses and Raised Over $75 Million in Capital

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      1:03:51

      $10M+ 2 Businesses – Susie Carder, CEO | SD Consulting

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      1:00:32

      $10M+ Annual Revenue – Annie Hyman Pratt, CEO | Executive Consultant Leading Edge Teams |The Coffee Bean & Tea Leaf Family

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      53:36

      $10+ Million in Annual Revenue – Rich Schefren, Strategic Profits

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      53:38

      $10+ Million in Annual Revenue – Rod Khleif, Lifetime Cash Flow Podcast

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      53:16

      $11.5 Million Annual Revenue – Nick Bogacz, Caliente Pizza & Drafthouse

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      53:17

      $18M Exit, Chris Guerriero, Executive Fitness Club

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      52:04

      $10M+ Exits – David Finkel, Multiple Companies

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      53:17

      $100M+ Exit – Minnie Ingersoll, Shift

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      53:57

      Rebecca Costa, Dazai Advertising Inc.

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      54:07

      $10M in Annual Revenue – TK Kader, ToutApp

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      54:15

      Recapping the Quarter

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      24:08

      Steve Olsher, Liquor.com

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      25:58

      $140M in Revenue – Dave Woodward, ClickFunnels

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      54:17

      $100M Exits – Kevin Harrington, several companies

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      54:18

      $200M+ Annually – Chris Cicchinelli, Pure Romance

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      53:41

      $20M Annually – Dr. Angela Lauria, The Author Incubator

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      54:11

      $50M Exit – David Schottenstein, Astor & Black

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      54:16

      $13M in Annual Revenue – Steven Sashen, Xero Shoes

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      54:18

      $37M+ in Revenue – Adam Hergenrother, Adam Hergenrother Companies

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      54:23

      $16M+ in Revenue – Doug Morneau, Real Marketing Real Fast

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      54:17

      $100M+ in Annual Revenue – Klee Irwin, Irwin Naturals

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      54:19

      $50M+ in Annual Revenue – Dr. Lori Barr, The Doctor’s Mentor

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      54:18

      $100M+ Exits and IPOs – Kenneth Aldrich, multiple companies

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      54:17

      $2.5B+ in Assets – Dwayne Clark, Aegis Living

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      54:18

      $300M+ in Revenue – Cameron Mitchell, Cameron Mitchell Restaurants

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      54:17

      $1B+ in Assets – Andres Pira, Blue Horizon Developments

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      54:14

      $20M+ in Annual Revenue – Steve Gray, Primal Labs

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      54:16

      $5B Exits – Jeff Saling, Exited 3 Companies

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      54:16

      $10M+ in Annual Revenue – Aaron Young Runs Multiple Companies

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      54:18

      $80M+ Exit – Michael Coles, Great American Cookie Company

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      36:56

      $10M+ in Annual Revenue – Nathan Hirsch, Freee Up

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      39:57

      $10M+ Exit – Mark Timm Exited 7 Businesses

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      49:13

      $10M+ in annual revenue – Chalene Johnson

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      50:58

      Being resourceful with Michael Houlihan, Barefoot Wines

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      54:16

      $10M+ in annual revenue – Ryan Levesque, ASK Method

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      54:16

      $40M+ in annual revenue – Tony Falkenstein, Just Water Intl.

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      54:18

      $25M in annual revenue – Kisha Mays, Just Fearless

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      54:18

      $40M Exit – Frank Shamrock, Strike Force

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      54:17

      $10M+ in annual revenue – Jonathan Cronstedt Runs Kajabi

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      54:17

      $10M+ in annual revenue – Garrett White Runs Wake Up Warrior Which Generates

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      54:17

      $30M in annual revenue – Mark Evans, American Wealth Builders, Cash Flow Lead Gen

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      54:42

      $30M in annual revenue – Mike O’Hagan, MiniMovers, Shore360, and MikesBusinessTours

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      54:41

      $10M in annual revenue – Lee Richter, Richter Communication & Design Group

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      54:41

      $10M in annual revenue – Nyasha Gwatidzo, Banya

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      30:35

      $10M+ Exit –  Parham Parastaran, Car-X Tire and Auto

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      54:19

      $10M Exit – Björn Öste, Dynasoft

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      54:16

      $2B Exit – Stuart Taylor, Taylor Nelson and Associates

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      54:17

      $10M+ Exit – Chip Conley, Joie de Vivre Hospitality

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      54:19

      $50M in annual revenue – Mike McDerment, Freshbooks

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      54:40

      $10M+ in annual revenue- Sabri Suby, King Kong

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      54:41

      $36M in annual revenue- Marx Acosta-Rubio, Onestop

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      54:40

      $83M Exit- Sharran Srivatsaa, Teles

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      54:38

      $30M in annual revenue- Colin Wayne, Redline Steel

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      54:40

      $50M in revenue- Steve Layton, Layton Groups

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      54:38

      Multiple 8 and 9 Figure Exits – Roland Frasier

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      54:39

      $10+ M Exit- Dan Kuschell

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      54:29

      $10+ M Exit- Melissa Krivachek, Melissa Krivachek Companies

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      54:29

      $11M Exit- Viki Winterton, Expert Insights Publishing

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      41:29

      $10.5M Exit- Mitch Russo, Timeslips Corporation

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      54:28

      £11.2M Exit- Jonny Cooper, Money Desk

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      54:37

      $4.5B Exit- Christopher Lochhead, Mercury Interactive

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      54:26

      $100M in Annual Revenue – Reid Tracy, Hay House, Inc.

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      54:32

      $20M in Annual Revenue – Anik Singal, Lurn

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      54:37

      Billionaire Naveen Jain, Viome

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      54:40

      Brian Smith | UGG Australia

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      54:29

      Introducing Beyond 8 Figures

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      11:37