Jack Corrigan - Redefining Real Estate Lending & Investing
Jack Corrigan is an accomplished real estate investment professional with deep experience in private equity, capital markets, and financial modeling. As Investor Relations & Fund Associate at The Lucky Group, Jack plays a key role in capital raising, investor communications, and fund operations—helping bridge the gap between strategy and execution. Jack’s career includes time at Greysteel and Stablewood Properties, where he supported underwriting, acquisitions, and investment sales. With over $80M in transactions underwritten, Jack brings a proven track record of evaluating opportunities and creating value.
Jack also leverages AI and advanced analytics to enhance portfolio decision-making—giving investors a competitive edge in today’s market. A graduate of the University of Texas at Austin with a BBA in Finance and Real Estate, Jack combines sharp financial expertise with strong relationship-building skills to drive investor engagement and capital strategy. If you’re interested in real estate investing, private equity strategies, capital raising, or how AI is shaping the future of real estate, this episode delivers insights you won’t want to miss.
In this episode, you will be able to:
- Discover how real estate investing can unlock true financial freedom even when your income comes from gig work.
- Learn how to smoothly shift from a W2 job to entrepreneurship without losing your mortgage eligibility.
- Explore unique mortgage solutions designed specifically to help gig economy workers secure home loans.
- Uncover strategies for expanding your real estate portfolio into new markets while managing income unpredictability.
- Build powerful investor relationships in real estate startups that can fuel your growth and open doors to new opportunities.
The key moments in this episode are:
00:00:00 - Innovative Homeownership Model for Gig Economy Workers
00:01:27 - Introduction to Jack Corrigan and His Real Estate Journey
00:03:22 - Entrepreneurial Mindset and Early Influences in Real Estate
00:08:30 - Challenges for Gig Economy Workers in Qualifying for Mortgages
00:16:09 - Formation and Growth of The Lucky Group LLC
00:18:15 - Loan Process for Non-Traditional Income Borrowers
00:20:26 - Investor Opportunities and Geographic Expansion Plans
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Full Transcript:
Jack Corrigan
These people can still afford homes. Their income verifies it. They've had really strong income over the course of the last 12 to 24 months. As long as we can qualify them for the ability to repay, we understand where they're at in terms of their income and we have a strong feeling that they will be able to repay us because we're going to give them a house. We'll go in, buy the house on their behalf, sell it back to them the same day, and then initiate a mortgage once they've given us a home buyer down payment. It's a very unique model that I've never really seen before.
Mike Swenson
Welcome to the Real Freedom Show. We inspire you to pursue your passion to gain time and financial freedom through opportunities in real estate. I'm your host, Mike Swenson.
Jack Corrigan
Let's get some real freedom together.
Mike Swenson
Hello, everybody. Welcome to another episode of Real Freedom Real Estate Leveraged Freedom, where we highlight people building time and financial freedom through different opportunities in real estate. I'm your host, Mike Swenson. And if you want to get started on your real estate investing journey or learn more about how you can get involved in real estate, check out our website, Freedom through Real Estate dot com. We always have great content, our interviews, blog posts, you name it. To help you with the goal, really to inspire you to get into real estate if you're not in real estate or if you are, maybe help guide your path to figure out where you're going to land to ultimately be in this awesome entrepreneurial playground that is the real estate industry. So today, excited to share with you, we've got Jack Corrigan. Jack is investor relations and fund associate at the Lucky Group. Comes from a background outside of real estate, has been and worked in real estate, has a lot of experience. And so just like all of our episodes, we love telling great stories. The goal is for you to, you know, find something that you connect with, whether it's the background, whether it's why real estate, whether it's a story, whether it's the asset class that we highlight, whatever it might be. And so excited to have Jack on the show and share your story. So welcome.
Jack Corrigan
Thanks, Mike. So happy to be here.
Mike Swenson
Just go ahead, give us a little bit of background about you and we'll go from there.
Jack Corrigan
Feel like I have a pretty diversified background coming out of college, graduated from the University of Texas, Hookham Horns. That was my dream school. Absolutely loved my time in college and kind of fell into real estate after going to as many events as I possibly could, but definitely found that Passion when I was still in school, got my agent's license and hunted with a brokerage shop as an intern. Just wanted to get more experience and learn. My full time background, like you mentioned, is not in real estate, it's actually in bartending where my mom and dad were bartenders in Manhattan, New York. They own bar. Fast forward about 20 years later, my dad is working for the UN and my mom was a lawyer. And you know, the story keeps writing itself. But since coming out of school, I've closed, give or take about 120 million in transactions, underwritten a lot more than that. And I'm currently capitalizing for our firm, the Lucky Group. We're a little bit more on the startup side right now where, you know, we see massive growth potential over the course of the coming years once we actually get more capital people, more capital intensive units. Still some things that we're figuring out on the front end and back end. That's part of the beauty of being a startup. But really, really excited for all the people that have partnered with us and obviously excited for future partnerships as well. Happy to dig into all of that. And again Mike, just really happy to be here with you today.
Mike Swenson
Now with your background being kind of entrepreneurial, you were exposed to that at an early age. That contrasts for me, I was kind of instructed, work at a W2, save for your 401k, everything's going to be safe, stable, you can count on it. And the way that that worked out for me was, you know, both of my parents were actually let go from their jobs shortly before retirement age. And so I got a chance to see that not work out all the way to completion. Now for me, they were close enough where they were able to make it work. So it wasn't kind of a tragic ending there, but it could have been. And so it took me a while to kind of take the turn on the entrepreneurial route. Actually got a degree in entrepreneurship, but. But for you, talk about growing up in kind of that entrepreneurial environment or even just the maybe less consistent environment. Consistent is probably not the right word, but talk about kind of your upbringing and mindset as it related to W2 versus entrepreneurship and then two kind of what attracted you to getting into real estate?
Jack Corrigan
Great question. I feel like I'll probably answer both of them a little bit more as well down the line. But I guess let me give you and some of your listeners some background on me. Grew up in Manhattan, New York, born and raised for 20 years. Mom and dad are bartenders in Manhattan. That's how they met and ended up owning a bar. Did that for about five or so years. That whole entrepreneurial experience completely. Mom was a history major from Baylor, moved from Waco all the way to Manhattan chasing her cousin. My uncle ended up meeting my dad, an Irish immigrant from Dublin who at the time was, you know, working doorman jobs, working as a bartender, trying to get his foot in the door at certain companies like the United nations, where he ended up working for the better part of 20 years. Always entrepreneurial minded, always thinking, what's next? Always thinking, where can I go to go find that opportunity? Where can I go meet someone? I'd always say that I'm grounded in my entrepreneurship in terms of understanding, you know, what's the opportunity cost, what's the sunk cost, what happens if you do this or that? I think that's also a really big important part of entrepreneurship that sometimes doesn't really get laid down in foundations where those are important. You need to understand what is my overall income, what's my cost of living, what can I save on, how can I cut down expenses? All of that. Definitely learned that in the bartending industry after about six years doing inventory, leading people, training new bartenders can also get in a little bit to my, I guess officiating background as well, where I will tell you, I officiate high school football here in Texas. So being a part of a team that's really, really, really, really connected, being able to talk over the phone, give a signal like, hey, this doesn't look right. All of it relates, I guess, digging in a little bit more on why real estate or how I found it. It's funny, I think it's a little bit of a mix of bartending in college and officiating high school football and obviously my background' finance. That's where I got my degree. I love underwriting and understanding certain financial metrics. I think that irrs are the beauty of finance and at the very least understanding your investment opportunities can get into that, of course, if we'd like to. But again, fell into real estate. Thought it was a great intersection between finance, our tending and that teamwork that I get in officiating. But always looking to meet new people, like I mentioned, I guess before this interview started. Always trying to call new people, always trying to get on cold calls, always DMing random people on LinkedIn, just asking for quick, you know, five minutes, 60 seconds, whatever you got time for. Would love to know how we can work together now or in the future. And I think that that's the Beauty of this business, you never know when you're going to meet someone at the right time. Maybe now's the wrong time, but that doesn't mean it will be in the future. It's always about keeping an open mind, being transparent, and being honest with yourself that you're not going to take up someone's time for, you know, all of 60 seconds.
Mike Swenson
I think back to, you know, when I first got into real estate. So I got into real estate on the admin side and, you know, hearing my boss, who grew up entrepreneurial the entire time, didn't have a job, didn't really even understand kind of what a W2 even looked like or how that worked. You know, he'd asked me these questions and I was like, how do you not know the answer to this? But he just. Because he grew up on the entrepreneurship side and really opened my mind to the unlimited possibilities that being in real estate can have. Even as we're talking about, you know, I started on the residential real estate side. So if you think about, you know, know, agents slinging homes and things like that, it's like, you know, there's. There's no limit. You could have two closings a year, 20, 100, a thousand. You can have as many as you want. And so for me, kind of in this W2 mindset, I kind of had maybe a little bit of a cap on the top of, you know, thinking what's possible. And that's what I love about real estate is, yeah, you may not end where you started in terms of kind of which path in real estate, but there is unlimited potential. There's so many cool things that you can do, so many great connections. And for you, just being able to meet different people, connect, there's a world of possibilities between now and the rest of your life.
Jack Corrigan
Completely agreed. And I think that's also a great segue into what we do at the Lucky Group. And I do want to get into that, but I can completely relate to you and I guess more along how the lines of you grew up, you know, in W2 versus 1099 space. I'll go back to just a second here for bartending and I guess without trying to get too political, the big beautiful bill that Trump's already passed, no tax on tips. I think that we can all agree that is phenomenal. That should have been passed long, long time ago when my mom and dad were working, may have gotten them another bar or two. But again, bartenders, service industry workers, as we all know, they're some of the lowest Paid people on the planet, they get somewhere between two to five dollars an hour and then the rest is just tips. Those are all W2 jobs, even though in reality it's all performance based. Right? You don't make a sale. You don't necessarily. Maybe there's an autograd or something like that, bars and restaurants, but everything that you do, tips. Everything that you make, tips. I've been fortunate enough that, you know, I'm a decent bartender and have been tipped very handsomely at times. And maybe some of that's charm, maybe some of that's work ethic. I think that all of those go hand in hand in entrepreneurship. At the end of the day. And to your point about really unleashing yourself and others in the 1099 space, you eat what you kill. If you're a killer, go be one. That is a little bit more of what I guess we'll get into at the lucky group in that we're not killers, we're actually assisters. So think of people like, you know, me in a past life, Mike, whether I was a bartender, an Uber driver, a sports official, you name it. People with 1099 contractor income that they can make money, but they're unqualified through banks. A lot of that's due to 2008 and the conventional lending system. And total kudos to the banks that did tighten up because again, there was a lot of stuff happening in 08 that was not very great. However, because of those, let's say, malfunctions of the financial system back then, we're in today's current economy where we have an amazing gig economy. 20 to 30% of the current workforce is gig economy. We expect that to continue to grow by 2035. However, because they're contractors, they cannot be qualified by banks for mortgages. That's kind of where the lucky group can go in and assist people. And I'd love to, I guess, dig into that a little bit more if I can right now.
Mike Swenson
Yeah, yeah, for sure. Go ahead.
Jack Corrigan
So again, like I mentioned, these people have strong income. Maybe they have a lower credit score because of outstanding student debt. Maybe they're close to paying it off. Maybe they've been late on a mortgage payment, maybe they've been late on credit cards. There's a lot of things that go into FICO scores that I can segue to potential people that are interested on another call. But these people can still afford homes. Their income verifies it. They've had really strong income over the course of the last 12 to 24 months. As long as we can qualify them for the ability to repay. We understand where they're at in terms of their income and we have a strong feeling that they will be able to repay us because we're going to give them a house. We'll go in, buy the house on their behalf, sell it back to them the same day, and then initiate a mortgage once they've given us a homebuyer down payment. It's a very unique model that I've never really seen before outside of this company. And again, I think it positions us really well for long term growth and that we don't have any holding costs. We only have so much of a lockup period. Again, we are in expansion mode right now, which means that we got to be really careful with how we're spending our money and the clients that we're taking in. But at the same time, we're really excited about the prospects and continuing to help others. We have about 50 or so people that are currently lined up just here in Texas for our mortgages and now it's just about continuing to get them into the homes that they they want, making sure that themselves and their families are well taken care of from both a home equity standpoint and a mortgage standpoint. Last thing that we want to do is hurt anyone with our loans. Best thing that we can do is unlock HELOCs for them and continue their family continued stewardship. Just be honest, good business people.
Mike Swenson
That was a bit of a moment of awakening for me, leaving my W2 and choosing to go full time into real estate. That happened right around Covid. And I remember we had just recently moved to a house, which thank God that we did because I didn't even really think about that at the time, like, okay, we've got the house. I did think about it when it came time to having the home equity line, probably could have refied for a little bit lower. But then all of a sudden, now I'm entrepreneur and you know, having conversations with our lenders and it's like, well, you're not in a W2 anymore, so we need at least two years of tax returns. And I was thinking, shoot, what happens if, you know, what happens if life changed and I had to move somewhere else or do something else? I was kind of stuck. And so we're fortunate to be in a home that we want be in for a while, but not everybody has that opportunity and life happens and stuff happens. And yeah, traditional banks can work well for some people, but yeah, there's a whole group of people that doesn't quite fit what that need is.
Jack Corrigan
And we think that that's a really, really strong untapped market. We've actually internally underwritten that market to be, give or take, about $170 billion. The mortgage industry itself is worth 2 or 3 trillion. I'm blanking on it off the top of my head. But that untapped percentage again, Mike, to your point, these people that have qualified income, they're making strong returns on their money. They clearly have a great job going for them. That's how we were able to qualify them. But they should be able to qualify for mortgages. And to your point, again, a lot of people don't really understand that when they do leave their W2 job, that's something that we're trying to fix with our company. And who knows, maybe later down the line. Banks do cater to people like that with contract work. Maybe they're not just looking at tax returns, but we have a strong underwriting system in place where we have guidelines, we have underwrites that can qualify people currently working a few things in there between a fintech platform and emerging market technology. Happy to go into that a little bit more, but there is some stuff that I can't fully disclose at this time, but cannot agree with you more that 1099 is the way to go. I mean, some of the most successful people that I know have been 1099 workers and not gone to college. That is not me saying don't go to college, please go to college, get your degree if you can. But for those that can't or they just don't think it's for them. Nothing wrong with working your tail off to get to where you need to go and obviously even asking for support along the way. I always tell people to reach out to mentors, always reach out to new people, expand that network and meet new friends. Who knows, maybe your best friend that you're gonna start your later firm or company with is on the other end of a LinkedIn DM on a Wednesday. You have no idea.
Mike Swenson
Are you looking to get started or scale in real estate investing but don't know your next step? Are you overwhelmed thinking about finding deals, analyzing deals, doing due diligence and managing properties on top of it? Go ahead and push the easy button and invest with us. Real estate investing is what we do full time. We've done dozens of deals with hundreds of doors. We have the knowledge and experience to hand pick the best deals that most investors can't find. We've got large off market deals all the time where you can hopefully find returns and economies of scale that you just can't find on your own. The best thing is it's 100% passive to you for less capital than you put down trying to acquire a property on your own. Don't let this year go by where you don't make the leap add to your portfolio or you just sit in analysis by paralysis. To find out more, visit freedomthroughrealestate.com and click on Invest. You can book a call and learn more there. So get to scaling your portfolio Portfolio now with us by your side, talk about a little bit of how the Lucky Group got started. I'd love to kind of hear what caused the it to form and kind of how did it come to be.
Jack Corrigan
Definitely. So company was formed in 2023 before my time. It was originally more of a consulting program than an actual company, but the Lucky Group LLC was the name of the game. Upon, I want to say 17 originated transactions over the course of the first year they got 17 people into homes. They realized the capital request, they got those returns back to investors that were very strong, about 20% IRRs at this time. That's been changed a little bit so that we can actually make it into a fund structure. We can continue the mission of helping people get into homes while still making strong returns. It's just that at this point, now that it's going to be a fund, those aren't 20 or so percent. It's a 10% pref return with a 12% target IRR, which I will tell people we're happily making at this point. We are still looking for more investors to obviously continue our pipeline, expanded to new markets, find new territories and help people. But it all comes with time. Patience is a virtue. Meeting people and getting on podcasts and making new friends, like you and I are doing right now, Mike, is hopefully exactly what we're supposed to be doing in order to keep growing.
Mike Swenson
So essentially you're kind of creating a bucket of money, right? So you've got the investors coming in, putting money into something that's going to give them a great return and then you're funding the other side or helping the other side of the people that need these loans that can't necessarily get those loans or have a hard time qualifying for those loans. So you're kind of helping two people at the same time and creating an investment vehicle that meets in the middle and works for both sides.
Jack Corrigan
Exactly. And we're always telling people we want to be win, win, win for Everyone. We never want to hurt anybody in the process of investors, clients, ourselves. The only way that we originate mortgages is once they're qualified. We've known them for X amount of time, we see their income verified and then we'll help them. But to your point again, Mike, we always aim for the win, win, win. I think that that's the beauty of real estate. That's what you always want to aim for. And if you can continue to do so, you're going to have a great career.
Mike Swenson
So touch on the lendy side. Right. So I'm looking for a home. You've kind of already touched on this, right? I've got a job that doesn't necessarily have the traditional requirements for a loan. So what does that process look like for me talking with you guys?
Jack Corrigan
Definitely. So you have to give us a minimum 10% of a down payment, right? Let's say that the home is worth $330,000. Give us 33,000, we'll lend you the rest and that'll be your mortgage Note fixed over 30 years. We only do 30 year amps. We only fix those schedules. We don't have any adjustable rate mortgages. That's what a lot of 2008 was. We felt like that wouldn't go over too well in 2025 with, you know, 1099 contractors. It's contract work. We want this to be very easy, clean, simple for everyone, such as a lendy like you, Mike. So again, you want a home, $330,000. You give us 33 grand, we will lend you the rest and make that a fixed note to essentially take an interest income over the next 30 years. All of those funds go back to investors. The last thing that we want to do is give you the highest rate possible. We do charge a premium once we go through the resale process. But the only reason that we do that is so that we can get those returns for our investors. We disclose that up front to people so that they know, look, the reason that you could get this loan is because these investors are believing in the mission that we are doing. Our operating company and the founders involved. If you want us to help you, you need to help us and sign up for this. And we always try to make that very clear up front. I will say that since, you know, our team has been assembled, we have not had any defaulted mortgages. We've done about 30 or so loans since 2023 and like I mentioned, are looking to expand on that into hopefully the next 50 or so clients, just here in Texas and then again, continue to build that pipeline in more states, but really happy with our current progress in terms of where we're at. We do have an open house actually at the end of the month. So if any of your listeners want to maybe meet us face to face, happy to connect on LinkedIn, shoot me a DM and, you know, would love to meet you guys. Like I mentioned, we're in Austin, Texas, so shout out Austin. Welcome.
Mike Swenson
Awesome. So that's what kind of happens on the. On the lendy side. So. Yeah. Then on the lender side, you know, you mentioned about starting a fund or having a fund. So if somebody's interested in that, what does that look like?
Jack Corrigan
So just for my own clarification, are you asking if somebody wanted to invest in our company?
Mike Swenson
Yeah.
Jack Corrigan
So we have two different raises. One is an LP raise, which that requires an NDA, and I don't necessarily can go into that right now, but there's also the LP raise. So if you're looking for passive investment opportunities where hopefully this is where you and I can start smiling a lot. Mike, you invest with us. I want to say that the minimum is about $50,000 credited investors, only 506c offering. You invest with us, we'll take that money. It'll go into purchasing homes in which we'll unlock that equity, taking out a first lien, then we sell it back to our home buyer on that end, giving them the mortgage and then taking those proceeds to return to investors. That process is very repeatable, and it makes it really easy to recycle capital without getting too messy or too frictional. At the end of the day, we obviously need one in order to get to the other. We need really smart people that want to believe in us and believe in the mission. And, you know, some of that comes from venture capitalists, some of it comes from private equity, some of it comes from commercial real estate. People that I've worked with in the past. And even if they're not necessarily wanting to invest, I always try to ask, what are you currently working on? How can we work in the future if it's not. Yes, today? Would it be something that you might look at in a year? Some of that is, you guys are so young, you're two years old. Well, at the same time, when are you actually going to invest? And again, not trying to pressure anyone to invest with us, that's the last thing that we want to do. It's just a calm conversation of, okay, I totally respect that decision. How can we work together?
Mike Swenson
So you guys are in Austin now. Is most of your lending in the Austin area? Just Texas in general. And then what does that look like for your your possible expansion into other states?
Jack Corrigan
So most of our current property or most of our current borrowers are here in Texas. We are expanded into three states at this point between Texas, Florida and Tennessee. We're looking to expand into more markets, I would say give or take 10 by the next quarter. Not Q4 but Q1 of next year. We'll see how far we get in those expansion plans. We are a smaller team right now. We're always looking at new ways to implement AI and enhance efficiencies within our workflows, be on top of things from a communication standpoint and work around everyone's schedule. Again, we're lean and green ESG friendly and very, very intensely communicating with both our borrowers and investors. We have our head of Relationship management, Justin. That kind of works a little bit more with the investor pool. I'm more on the sourcing side, getting in touch with people, getting on podcasts, getting on webinars, SDRAs, you name it. Again, always just looking to continue the mission and meet new people.
Mike Swenson
Well, thank you so much Jack for coming in and sharing just a great story. And yeah, you're helping multiple people. For people that want to reach out, both as a borrower and as a a lender, how can they do that?
Jack Corrigan
You guys can reach me at my email Jackeluckygroupinc.com or look me up on LinkedIn. I'm slowly becoming LinkedIn popular. I think I have like 8, 000 followers or something like that. Full disclosure, I DM as many people as I can, so it doesn't super surprise me. But you know, when you look at the numbers, it's like, wow, that's not bad.
Mike Swenson
Awesome. Well, thank you so much for coming on and sharing, Jack. Love what you guys are doing. Obviously meeting a great need, providing a great investment vehicle for investors as well and excited to see where you guys take things in the future.
Jack Corrigan
Thanks so much Mike. So appreciate your time. Looking forward to staying in touch and feel free to give me a call anytime. Would love to do this again.
