In this episode, Big Mike welcomes Dave Seymour, retired firefighter, real estate expert, and star of A&E’s Flipping Boston. From battling fires in Boston to leading multimillion-dollar private equity deals at Freedom Venture Investments, Dave’s story is one of grit, faith, and relentless reinvention.
He opens up about his journey from financial hardship to becoming a trusted investor and educator in commercial real estate. Dave shares his insights on navigating today’s distressed market, building trust through transparency, and helping professionals generate cash flow and equity through his Legacy Alliance Masterclass. With honesty and humor, this conversation dives into the realities of investing during challenging cycles—and the importance of integrity in wealth building.
About the Guest
Dave Seymour is a retired firefighter turned real estate investor, educator, and entrepreneur. He is the CEO of Freedom Venture Investments and founder of Legacy Alliance Masterclass, an educational platform empowering investors to create wealth through commercial real estate. Known for his dynamic presence as the star of A&E’s Flipping Boston and frequent appearances on CBS, CNBC, Fox, and ABC, Dave brings years of hands-on investing experience and candid perspective to every conversation.
HIGHLIGHTS OF THE EPISODE
00:19 – Welcome to the BigMikeFund Podcast
00:53 – Boston vs. Brooklyn banter and the firefighter-to-investor story
02:27 – Immigrating from London and the working-class mindset
03:17 – Financial struggles and faith during the 2008 market crash
04:12 – Discovering real estate education and mentorship as a way out
05:05 – Becoming one of Massachusetts’ top distressed asset investors
05:49 – Landing Flipping Boston and the power of perceived expertise
06:54 – Building a multifamily and lending portfolio across the U.S.
07:39 – Transitioning to private equity and investor partnerships
07:56 – “Stay alive in ’25, fix it in ’26”: navigating today’s market reset
08:54 – Distressed deals ahead: $1+ trillion in multifamily opportunities
09:56 – Educating deal finders through the Legacy Alliance Masterclass
12:00 – Helping professionals boost retirement through real estate
13:15 – Why thriving beats surviving in retirement planning
14:00 – Real estate as a team sport and the power of community
15:03 – Raising capital through transparency and early honesty
16:16 – Handling trapped capital and maintaining investor trust
17:20 – Turning education into deal flow: Legacy Alliance’s model
18:01 – Lessons in transparency, humility, and resilience
20:00 – The truth about risk, responsibility, and investor expectations
21:25 – Real estate vs. stocks: long-term conviction despite setbacks
22:05 – How to connect with Dave Seymour
If you found this episode substantial and want to dig deeper into real estate, or maybe you want to discover better investment opportunities, be sure to check out www.tempofunding.com.
CONNECT WITH US:
Website: www.tempofunding.com
Youtube: https://www.youtube.com/channel/UCnJkdVoOsUy85ydkmot9iVA
LinkedIn: https://www.linkedin.com/in/mzlotnik/
Facebook: https://web.facebook.com/TFmanagementgroup/?_rdc=1&_rdr
X: https://twitter.com/management_tf
CONNECT WITH THE GUEST
Education: legacywealthmasterclass.com
Website: freedomventure.com
LinkedIn: http://www.linkedin.com/in/daveseymour343
Full Transcript:
Mike Zlotnik: Welcome to the BigMikeFund Podcast. I’m the Big Mike, Mike Zlotnik, and today it is my pleasure and a privilege to welcome David Seymour. Hey Dave.
Dave Seymour: Hey Mike. How are you buddy?
Mike Zlotnik: Great to have you. I know you hail from Boston. I’m in Brooklyn. I’ve been in Boston many times, kind of northeast is so cool. I love Boston. Yeah, the winter’s just little tougher. But beyond that, it’s a great city.
Dave Seymour: Yeah. It’s the only time the Yankees and the Red Sox can have a good conversation is when we’re doing it over a podcast like this.
Mike Zlotnik: For the record, I’m Buffalo Bills fan. I’m not really a baseball fan, so I’ll take a step back.
Dave Seymour: How about that? So, here you go. I’m sorry. Okay, Mike? I’m sorry. That’s all I gotta say for you.
Mike Zlotnik: Listen, that rivalry goes back many years and it’s a friendly rivalry, so, yeah, it’s good. Alright, lemme introduce you.
Dave is a retired fire fighter. Thank you for your service. Became a top real estate instructor during the last market crash. He’s an expert in commercial real estate, multifamily in ground up construction development transactions. Dave, SE start on A and E flipping Boston as well as on CBSA, BCC, NBC, Fox News, you know, wonderful resume.
It helps both new and large investor groups through complex deals at Freedom Venture Investments. That’s your company? And you have a Legacy Alliance is his educational outlet showing busy professionals how to master investing for cash flow and equity. Welcome.
Dave Seymour: Well done, well done. Every time I hear that read, I think to myself, they gotta shorten it up, number one.
And number two, I look over my shoulder and I say, who is that guy? It’s been a heck of a journey to be where I was, to where I am. You know, you, one minute I’m running into burning buildings. Next minute I’mrunning a private equity company. So it’s, how did this reopen happen? How, how did it happen?
Yeah. Long, long story short, I, I’m an immigrant to this country. I was born in London, England. I immigrated in 1986. Just a young kid, working class background. You know, I don’t, I don’t come from Yale or jail. thank the Lord. thank God. But, you know, I fo look Mike, I followed a plan that, that I think many folks, especially in the US and also back in the uk where my, my roots is.
You know this, this emphasis and reemphasis on working class, right? Trading 40, 60, 80 hours a week for somebody else’s money. And I, I followed that plan. It was given to me by my father. It was given to him by his father. So there’s no, there’s no mystery to it. but when I came to the States, America’s kind of unique in the sense that you can actually spend more money than you earn.
And I was incredibly good at that. you know, you’re carrying debt, the, the struggles of debt. And during the market crash 2005 through to 2009 10, it, it really brutalized me as a man. I’ll be frank with you. I was losing a primary residence. I was losing, my family. It was a very bad time for me. I am a man of faith.
I’m praying to my big guy and I’m like, I need some answers. I’m not hearing him direct. I expected him to send me a text or an email, tell me what to do, but he didn’t. but what he did do was, was I, I turned on the radio in my pickup truck and there was a commercial on there and it was, teach me foreclosure, a free one and a half hour seminar coming in your neck of the woods.
Learn how to do real estate, no money down. So I’m a product of that educational environment and I think the difference between myself and maybe some of my peer group was. Is I, I entered real estate and real estate investing. Mike, with the same mentality that I fought fires. I found mentorship and guidance.
I found a team. I never gave up. there was always an eye on the prize. work ethic was never a challenge, right? It, it’s not always how hard you work, it’s how smart you work and do. If you look to your left and your right, is there trust, right? If I, if I’m going into a building, I gotta trust that the guy going with me is gonna.
Watch my back and I bought, I look, I know it sounds so rudimentary, but I bought that with me, brother. I really did. I bought that with me into real estate. And, you know, we got some trajectory. I became known as the, one of the top, distressed single family asset investors in Massachusetts. I worked alongside the, I worked alongside the state.
The attorney general’s office had a couple of, programs for taking back properties from the banks who had abandoned these assets. And, you know, we got ’em fixed up, we got ’em back on the market. So once you can align yourself with, with state and local government, and you’re known as one of the good guys, that also opens doors.
landed me an opportunity to do the reality TV show, which you mentioned there. Flipping Boston. I’m the a and e network, and that was just, that was just, like a third party experience, like an out of body experience. One minute I’m sitting in a firehouse watching these shows, and the next minute I’m actually on these shows.
But the real, the real value in that was the perception of expertise, right? the look, the internet, the, the social media marketing, business awareness. It, it’s such a crowded world out there. We can see anything and everything within seconds. So how do you separate yourself from the rest of the rest of the cloud, crowd.
And, and I was blessed that the TV show did that for me. Oh, that’s Dave from flipping Boston. I’ll talk to him or I’ll invite him in. I’ll take his meeting, I’ll listen to what he has to say. And that just moved us along the, along the learning curve to, you know, being multifamily owners, you know, duplexes, triplexes, 6, 10, 12 plex properties.
I’ve owned assets in BC neighborhoods. I’ve owned assets in CD neighborhoods. Right. Is this all in Boston or you, you No, across, no, across the country. Mike. I, my, the portfolio that was, you know, hardcore property management was, in, Maine, up in the main markets. And there’s, you know, there’s a lot of, there’s a lot of poverty in that market, man.
But if you’ve got the right team, once again, you can go in there and, and earn a good living and be a good service. So. You know, I, I own those. I liquidated those. I’ve been on the lending side hard money lending, private lending. and then during COVID, we transitioned into where we are today, more of a private equity company just hunting and picking Delta in, in various markets throughout the US for our investors, primarily high net worth individuals, accredited investors.
And, you know, they put capital with us with an expectation of, you know, minimum of 21 to 25% IRR. We want ’em to feel good about an 8% pref. If we put it on the, pro forma. we want them to feel good and understand that, you know, we show maybe a two x or a three equity multiple on an asset, that we can achieve those things.
So, you know, that’s, that’s where we work. and, primarily in southwest Florida. And, we’re we, you know, we’re taking some hits right now. Be frank with you. Florida market’s kind of interesting. It’s. It’s kind of like the redheaded stepchild at times. It takes the beaten first, you know what I mean?
And, but if, if you, if we, if you buy right, if you, if you make sensible, underwriting, you stay conservative, stress test the performers, you know, it gives us, it gives us confidence that we’ll get through Stay Alive in 25 and start the fix in 26. That’s our, that’s our company motto right now. So we’re working
Mike Zlotnik: out.
Yeah. Yeah. I, I’ve heard these stories and it’s, by the way, it’s, it’s, it’s, it’s. The issue is brought around the country. I mean, for sure, having an open, honest conversation. The market reset in a huge way. Yeah. When the rates spiked and, lots of his Es SSP also became, well it, it turned out to be more difficult to operate than people thought.
Mm-hmm. Mm-hmm. And you said Southwest Florida, I assume it’s somewhere what? Between Naples and Tampa and that arrange Yeah. In that, yeah. Yeah, the I four corridor. Yeah. So what are you doing today? So it’s kind of one of those things where all these pro performance projections, these high IRRs that were all paper guesstimates and turn out to be, if you can get people their money back or even a portion of their money back today, that’s already a pretty good outcome.
Yeah. What are you doing now? Obviously existing assets. It’s a survival, it’s a battle to survive. new assets. It, it’s a great time to buy. Are you buying today? Are you finding these great deals from distressed sellers? Yeah, it’s back to 2008, 2009 days when the market reset. And you can get these things at a deep discount, right?
Dave Seymour: Yeah, yeah, yeah. So look, you’re, you’re right on the money. So what we are doing is, is focusing on how to capitalize on exactly what you talk about, the distressed market. I don’t know the exact numbers. Our team pulled them up, but there’s something like 1.2 billion in, distressed commercial multifamily, paper.
that’s coming into the market.
Mike Zlotnik: It’s a trillion, not billion. It’s trillion. It’s a trillion. The number is, there you go. The the number is, is, is, is,
Dave Seymour: it’s ridiculous. Whatever that number is, it’s not comprehensible to either you or I. Right? It’s, it’s zeros on a piece of paper, but you and I both know also that’s opportunity.
So how do you capitalize on something like that? Well, if I can just capitalize on, you know, 25 bips of that marketplace, that’s a pretty good, that’s a pretty good payday. So how do you do that? how do you scale on a, on a number like that? And we stepped back and we looked at it, and if I could, right, imagine a qualified team of of deal finders for want of a better term, who are experts in an analysis, underwriting, communication, et cetera, et cetera.
If we could send those, those team members out into the marketplace. show them where we see opportunities, you know, the, the, the, the, the macro pockets within each, each market. What would it be, like we said, as a company? What would it be like if they could bring that deal flow back to us? Obviously criteria, 50 to a hundred units, we wanna see the opportunity for, repositioning and increasing NOI can we buy at pennies on the dollar.
All all of the stuff that we know about. And we said, yeah, we can do that, but we can only do it through education. Just because somebody says they know something and can do something. You know, I’ve found in my career, maybe you have as well. It doesn’t always mean that, that that’s truth. But if I’ve trained them, if they’ve gone through almost a, a mini collegiate experience with us.
then I have a higher level of confidence that what they’re doing and what they’re saying has credibility to it. So that’s what we’re doing with Legacy Alliance Masterclass. We’re putting these people through this program. They’ll invest a small amount of money in that program. It’s just our, our cost to carry that program through you.
And then they qualified to actually do some business with us. Sorry, Mike.
Mike Zlotnik: Yeah, I’m, so that Mastermind is, is, is, is catered towards, smaller entrepreneurs who wanna find these type of deals. So you, you basically Yeah, absolutely. You’re finding these, these jockeys who you think they’re worth, doing business with and you’re teaching them how to do it.
Mm-hmm. That’s basically, yeah, absolutely. That’s what your mastermind,
Dave Seymour: yeah. If you look at, say you take the average American corporate. Individual, right? Maybe they’re earning, I dunno, 2 50, 300 a year. that’s a nice, that’s a nice paycheck. Maybe a little bit more, maybe a little bit less whatever, but they’re also paying into 401k systems and, and, and pension plans.
which when you do a deeper dive on, on those numbers, and where we’re going, even in a, an inflationary environment that, is maybe not as, not as truthful as we are led to believe. when you start looking at the, the, the cost of inflation. You know, a lot of these long-term, retirement plans, yeah, you can survive, but we don’t work, you know, 25, 30, 40 years to survive.
I, I hope where our plan is to thrive in, into retirement. So we look at those individuals and we say, can you carve off five, 10 hours a week? After being shown how to get into this game, this multi-family investing game, can you carve that time out and walk away from your, your corporate job, keep on working, all of those things over there.
But what if we can boost, right? Boost it. What, what if you’ve got an extra 15,000 a month coming in, you know, in cash flow off of, off of a, off of an asset portfolio, you know, what does retirement look like 10, 20 years down the line? And the sad thing is, is so much of these, these, the, these models that retirement companies use.
They just don’t take into consideration the fact that we’re living longer and longer and longer. They don’t take that into consideration, right? You’d retire at 55, you die at 65. That was the, that was the, the, the cut and paste plan. Well, today we know we, we we’re kicking around in our early nineties, some of us, and I don’t want to be laying in a cot in my, my kids’ basement because that’s all I can afford at the end of the day.
So without getting too sidetracked on it, that’s who we focus on. We focus on folks who wanna ize their retirement accounts. they wanna follow our plan. I’m not, I’m not interested in opinions. I’ll be frank and I, I hope I don’t, I don’t care if I hurt anyone’s feelings. We’ve made all of our own mistakes, so we don’t need to entertain anybody else’s, follow the plan and, you know, it’s, it we’re beginning to see some nice traction.
So that’s, that’s where we’re spending that time today. Mike.
Mike Zlotnik: Yeah. Yeah. I appreciate it. So you, that mastermind teaches people how to do it. Makes a lot of sense. I, I go to multiple masterminds, and I can tell you that yeah, it’s, it’s always good to be part of a strong community Yeah. And follow a well developed, system, so for sure.
Mm-hmm. Mm-hmm. Mm-hmm. And multifamily, any commercial real estate is a team sport. Yeah, for sure. Far more than resi residential. Mm-hmm. You could do a lot of projects, you know, you can buy an apartment or small apartment building and run it yourself, but the, the, in general, any kind of scale, it’s absolutely a team sport.
So let’s continue. how are you doing capital raising today? So, on a deal flow front, it’s kind of one of those things where deal flow is, is, I don’t wanna call it easy, but it’s gotten way better. Yeah. And the deals are steeper discounts, and it’s not volume, but it’s a, it’s a precision. You can find individual motivated seller situation, you can find a great deal.
You’re not looking to do 10 deals, you’re looking to do one great deal, right? So I think, but that, that’s easier to find, especially multifamily today. And as, as, as time passes, more pressure builds up. It’s kind of like the feds started to cut, but the, the too little, too late per se, so for sure agreed, on a capital front.
Well, we see, and you probably see the same thing, a lot of investors wrote their checks in 20 20, 21, 22. Mm-hmm. That money is stuck or lost. Mm-hmm. Right. Whichever is, is whichever is better. Getting new checks is not easy either, for sure. You gotta get new investors, or you gotta get people who still have fresh capital flowing in.
Mm-hmm. I’m just curious if you have any, any interesting observations on this front.
Dave Seymour: I do. I do. And, and maybe you’ll appreciate this, Good news travels. Go travels slow. Bad news travels fast. Right? We know that. So what we found is, is, is, and we made a decision with this early on, is to to be 100% transparent 100% of the time.
rather than just sitting in and, and waiting for, for an uncomfortable conversation, have it earlier rather than later. And, you know, your framework and and context was, you know. Money that’s trapped, or money that unfortunately could be lost. And I, I had one of those conversations recently with an investor, and just to give you a, a big scope on it, the money’s, the money’s trapped.
It was supposed to be out in three to five. It looks like it’s gonna be out in five to 10. Right? it’s not lost. It’s still in, it’s still working. We’re doing our very best. We’re fighting some forces beyond our control, but we do the best that we can. And there’s nothing more refreshing to have that conversation with an investor and them say, okay, well what else do you have?
And I think the only reason that they can then ask that question and us give them an opportunity to come into some other project because we’re we’re working other projects, is because of the transparency on the way through. And, anybody who’s in this business as an owner, operator, as the GP in any scenario, I, I beg of you to, to just be an open book with your investors. I beg of you to do that. it’s, it’s not pleasant. Let’s just be frank. It’s not pleasant. There’s a lot of egos in finance. We can be frank about that as well. Right? the gold makes the rules. I mean, I can’t tell you how many times I’ve, I’ve heard that, and yet I would then say to them, well, why is your gold in the bank instead of out in the street working?
I, I get it. I get it. So having uncomfortable conversations when they need to be had and, and doing your very best to not avoid those. creates that true transparency and and honesty that, that, that we have. And yes, we are always looking for new investors, right? So part of the, part of the Legacy Alliance education system is not only to educate, but there’s also people in there with capital.
So I might educate somebody, Mike. They’re all, you know, piss and vinegar and they love this thing and they wanna, they wanna be multifamily owners. And then they go, wow, that looks like a way too much work. Hey Dave, you got anything? Right? And they become, they become an accredited investor. So it’s, it’s a Trojan horse at the same time.
Mike Zlotnik: Yeah. so everything you said, I really love, I mean, honestly, kind of great minds think alike and people with integrity behave, Through good times and bad times and Yeah. It’s kind of funny that you say all these things ’cause we, we deal with this every day too. We’ve had these conversations. Yeah.
I’ve had these conversations and yeah. All you can do is be open and transparent. Mm-hmm. And, mm-hmm. Mm-hmm. Some folks, I correct this joke. I’ve had people who yell at me say, Mike is smart guy, but you’re also such an, such an idiot. Yeah. You should have seen I said, yes. What, what should I have seen?
Yeah. Well, the Fed could have hiked interest rates. They kept the interest rates at erp. They gave people cocaine called Zer, zero interest rate policy for 20 years. And suddenly you expect to withdraw cocaine and all these addicts are sort of having really difficult time. That’s what happened. Yeah, yeah.
And can you prepare for this? So long story short. Still market cycle, steal all these things, and we all learn and Yeah. But these conversations are definitely transparent. They, they’re open, transparent. I, I
Dave Seymour: had a, I had a call to people, attorney and some people will not. So what can you do about it? You just keep going.
What do you do? You keep going. I don’t know about you, my friend. I don’t think from, from meeting you on this, this podcast, I don’t think you’re in this game for the long, for the short run. Right. We’re in this for the long run and we’ll, exactly. We’ll ride, we’ll ride the cycles. you know, I was talking to, to my attorney, this morning, Tony Rosenberg up here in, in the Boston Market, and I’m like, Dave, you know, blah, blah, blah, blah, blah.
And I give him the scenario on, on some deal challenges and he’s, and, and I love. I’m an emotional guy. You know, when somebody says to me, Dave, I’m betting on you. The jockey, not the horse. I take that personally, but my attorney doesn’t. He doesn’t take anything personally, and he says to me, Dave, you did your due diligence to the best of your ability.
You talk, you walk through the pro forma, you stress test the pro forma. You did everything that you were supposed to do. You shared that with your investors. Your investors noted that they were accredited. They read the PPM, they read the. The, the, the offer in memorandums, they, they signed that paperwork.
You never told ’em there was a guarantee, right? Never. You can lose every single penny when you invest with guys like us, ladies and gentlemen. Or you can double, triple your money in three to five years with us. Ladies and gentlemen, you decide, here’s the information. so it’s great that he, he can be that way, but it doesn’t always feel that way for me as an individual because I too have a family.
I too have, you know, dreams, hopes, and aspirations. So it’s, it’s not a business for, for the, for the, for the lighter heart, right? You gotta, you gotta be able to stand, stand in your own shoes. Guy says to me one time, welcome to the big leagues kid. I come from like the single family stuff. He said, it’s time to take off your short pants and put on your long pants.
Here we go. I’m like, I get it.
Mike Zlotnik: Yeah. Dave, I appreciate that. Again, the words otherwise that everything you’re saying so re resonates so, you know, such a truth and, and, and an openness. And that’s the reality. I, had exactly the same conversations and, and, you know, attorneys will always be, you know, legal protection and if you’re using good attorneys, you’ll, you’ll have the right paperwork and.
But at the same time, still losing money even for the forces outside of your control, blame the fed or blame what you know, it doesn’t help. So folks, the worst part is this, and we probably have to wrap up, is Yeah. The crazy part is this long term, I believe real estate beats stock market, agreed. Every, you know, day, every day of the week, except for when it doesn’t, right?
And we, we saw a period of time when the stocks have have done remarkably well. Well, real estate market has had a very massive reset. So it’s a little bit of that difficulty where people, you know, sell the 401k, sell the stocks, put the money in real estate, and now they get a 50% haircut and they could have doubled their money.
So the feeling is very, is very, I mean, one of these people who sold some stocks that quadrupled in that time. Yeah. And if I get them half the money back, I, I’ll be pretty happy how, how crazy it is. Yeah. Yeah. So how will folks reach out to you? What’s the best way? What’s the website?
Dave Seymour: Look, if you’re interested in an alliance with us and actually a partnership type relationship, then go to legacywealthmasterclass.com.
Go on there, punch in your information, do your research. I mean, you know, I hate to say this, but it’s not for everybody. It’s only for a select few, you know, we’re very, we’re very particular on who we bring into that inner circle, but you can go there. I think my team will send you a couple of links as well, Mike, that you can put in any kind of show notes.
If you wanna reach out to me directly, just find me on LinkedIn. Dave Seymour, S-E-Y-M-O-U-R on LinkedIn. you’ll see my beautiful face. It’s actually an AI bot. I look a lot better in the AI photographs than I do, in my own photographs. But, you can find us and then Freedom Venture Investments, freedom venture.com, freedom venture.com.
You can find us there and see what we, see what we have going on.
Mike Zlotnik: Thank you Dave. Appreciate you sharing, lots of great conversation. I really enjoyed it. And good luck, with your journey on a forward basis. I’m sure you’re gonna do well. Appreciate you.
Dave Seymour: You too, man. Thank you.
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