Beyond the Deal

Building Wealth, Giving Back, and Finding Purpose with Alan Underwood

• Michael Wagman

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In this episode of the Beyond the Deal podcast, host Michael Wagman dives deep with Alan Underwood, a visionary real estate developer and charity leader in San Diego, California. Alan shares his extraordinary story of turning unimaginable loss into a purpose-driven life. From navigating profound grief to leading Angel Flight West—a charitable aviation organization—and transforming single-family homes into lucrative multifamily properties, his journey is nothing short of inspiring.

Discover how Alan’s reflections on time, self-love, and vision fueled his transformation into a successful entrepreneur and compassionate leader. Whether you’re a real estate investor, an entrepreneur, or someone seeking personal growth, this episode provides actionable strategies and hope.

Key Takeaways:
✅ Embracing brokenness to heal and thrive in business and life
✅ Powerful practices like meditation, vision boards, and self-empowerment
✅ Real estate strategies: turning single-family homes into multifamily investments in San Diego

Tune in to learn how resilience and reinvention lead to lasting success with Alan Underwood.

Timestamps:

00:00:00 Introduction to Beyond the Deal Podcast

00:02:21 Flying Adventures and Angel Flight West  

00:04:41 Life-Altering Events and Embracing Change  

00:07:22 Overcoming a Loss of Joy and Purpose

00:09:50 Transformative Power of Self-Love and Meditation

00:12:17 San Diego Real Estate: Transforming Single Family Homes into Multi-Family Properties

00:14:47 Prioritizing Family Time: Vision Board and Goal Setting  

00:17:09 Power of Identity and Affirmations  

00:19:25 Achieving Explosive Financial Growth  



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Welcome to Beyond the Deal, a podcast where we go deeper than the numbers and discuss the stories and practices that lead to success in life and business. I'm your host, Michael Wagmann. I've been able to raise millions of dollars for real estate while traveling around the world and living a lifestyle of freedom. Today on the show, my guest is Mr. Alan Underwood. Alan, thank you so much for being here. Michael, it's good to see you again and I'm excited for our conversation. I'm very happy to have you here. You're one of the most interesting people I've ever met. We've been friends now for a couple years and I've I've really watched you do some awesome things in that time. So we'll get to kind of the story of how we met and everything like that. But first, why don't you tell our listeners just a little about what you have going on in your life at this time? Well, I think probably the most important thing for me is family. I just became a grandpa, which sounds really weird to say that, but it also has been one of the most enjoyable things. Probably second to that is I lead an aviation charity where we do free flights for people in need of medical care far from home. So that's my passion project. And thirdly, I guess on the professional side, like you, I'm involved heavily in real estate. I develop real estate in San Diego and invite investors to build momentum in their portfolio by investing with us and what we're doing out there. Very cool. And we we will certainly get to the real estate thing in a minute, but I have to say one of the coolest things I've ever done in my life was fly up in that little plane with you. You know or five-seater plane and and you let me take the wheels or or the the handlebars, so to speak, for a little bit there and then you also pretended to crash us. I know I've seen plenty of videos of you doing that freaking out everybody who gets to ride with you, right? So tell our listeners just a little bit more about what you're doing with Angel Flight West because I think it's one of the most admirable things of anyone I know doing. So a couple of years ago, I got involved with Angel Flight West and what Angel Flight West has been doing for 40 years is providing free non-emergency medical care by air for people in need of medical care far from home. We also do free flights for active duty and retired military personnel. We do free flights for victims of domestic violence and abuse. We do free flights for people traveling to be with a loved one who's going through a difficult medical situation. And about a year ago, I was invited to lead the Arizona wing of Angel Flight West, it's about 200 volunteers, and I love the opportunity I have to fly with these men and women, and and also the opportunity that I get to know the passengers and people that we're serving, the other nonprofits that we work with. So it's been a great couple of years doing something, using something that I love flying to provide a really meaningful service for people that need it. So your background is not in real estate, correct? You were a car dealership guy for a long time, is that right? Yeah, I've done a lot of different things. I used to think that I had like business ADD. So I would start a business and once it was kind of up and running, it would get boring to me. So I would do something else. My first business was actually a pizza restaurant. So I did that when I was 22 years old. Sold that when I was, I don't know, probably 25 or 26, got into the car I've decided that I didn't like being an employee in the car business, so I started a car dealership and did that for 13 years and sold it in 2020 and that's really when I went full-time into real estate. I kind of dabbled before that, made some money, lost some money, but the last four years or so is really when it's become full-time and most definitely what I'll be doing probably for the rest of my life. Yeah, and can you sort of share a pivotal experience or a defining moment that kind of led you you into full-time real estate thing? Yeah, it's funny. I I did it because I had to or I wanted to because I had to. And the pivotal experience and you and I have talked about this was really a series of events that first I would say completely shattered me and then led to what has been several of the most growth oriented change related years of my life. So in 2018, we found out that my mother-in-law had cancer and we lost her a week later. And 13 months after that, we lost my father-in-law to cancer. And 13 months after that, my dad, who was only 66 at the time, had a massive stroke and passed away. And those three events completely shattered me and also caused me a lot of reflection. My dad being 66 was, you know, 23 years older than I was at the time. I was 43 and I looked up up and wondered, wow, if there's only 20 more of these rotations around the sun, you know, that's 20 more summers, 20 more Christmases, 20 more birthdays, 20 more anniversaries, whatever. That's not that much. And I realized that there were a lot of my own dreams that I had put on hold for whatever reason, not giving myself permission and maybe not believing that I could do it. But also I'd spent a lot of time building a business and not being home with my family. And I didn't want the next 20 years to look like that. So made the decision to sell the business and and trying to figure out what the next 20 years would look like. And I think I've figured that out now, that can always change, but that those were the sets of circumstances that forced me to become different. So in the wake of all that grief and loss, was there any sort of habits or, you know, what, how did you overcome that? What did you do in your life to move on from those, from that loss? Well, initially I didn't. So, you know, the first part was just, and anybody that's gone through a significant loss, divorce, death, you know, loss of a job, whatever, the, I like to say like the impact point of that, which really, and kind of the the straw that that broke me was my dad's death. And for several months, I didn't I didn't even want to live. And in fact, in a few days, I'll be sharing this story with a church group. But I can remember very distinctly sitting in my truck looking at the gun that was in the in the console of the truck and just thinking it would be so easy just to not do this anymore. And I don't know i don't know that I ever wanted to die, but I didn't want to live anymore. I had completely lost happiness and joy and none of it seemed worth it. And, you know, there there were a series of things that happened after that to help, but initially, you know, I didn't get out of bed. I really lost all control on who I was, what I was doing, and I just didn't care. So like the first part was just not pretty. There were never really any like super destructive habits or anything, but I I also just stopped really caring. I didn't really take great care of myself, put on a lot of weight, spent probably an inordinate amount of time, you know, watching movies online and stuff. It's just lost. And there were some very specific things that have happened in the last few years to help with that recovery that we can certainly go into. But you know the first part of it was just a complete and utter mess. And if if there's anyone listening who's there right now, I would just say, that's okay. It's okay to be broken. And even the things that you're doing just to cope, it's okay. You're just doing the best that you can. And I would also add there's hope for it to be a lot better and your life can change very rapidly. But from where you're at right now, you're just broken and you just need to heal. You know I remember when I first met you, it was pretty fresh still in the wake of all happening a couple years ago. We were really on the up path, but still not quite where you are today. Can you talk us through a little bit of joining GoBundance even and the impact that that's made in your life and how you got into these kinds of real estate deals that you're doing now? Yeah, great question. GoBundance has been transformational. Some of that has just been being in close association with other people who have also failed in spectacular ways and then and they've also come back and are now succeeding in spectacular ways. So it gave me hope that regardless of where I was, that it could be better. Also conversations where people were willing to see where I was and invite me to a higher place. You know, one of those conversations was, you know, a question that totally changed my life and still does. It's still something that I practice. And the question just was, on a scale of zero to five, how much do you love yourself? And when that question was asked, I wasn't at zero. Zero was sitting in the truck and looking at the gun. I was probably at a two. And the invitation that followed was, well, when you get to a five, everything that you want in life will come to you. And I didn't know how to move the needle. And so I spent a lot of time thinking about that question, is how do I learn how to love myself? and eventually developed a meditation practice where I would visualize walking up to the version of myself that I wasn't proud of, that I was ashamed of, that maybe even I wanted to forget and telling myself, Alan, I love you just the way that you are and I want you to come with me into our future. And I would look at myself as who I had been, who I was and who I wanted to be and express love for that person. I did that every day and eventually through that practice learned how to love every part of me. good, bad, ugly, the parts that I used to be ashamed of, the things that I was afraid of, but also the victories and the big wins and you know the guy that had been everything that he wanted to be in that moment. And so that was that was one of the most transformational conversations I've ever had and continues to inform a lot of the things that I do on a daily basis. I learned how to do breath work from somebody in Gobundance, Ryan Kennedy. That practice led me to creating a vision board and affirmation statements and you know the Probably 30 months of having a vision board and and after some nation statements that support that have completely changed my life. There are things that have had. happened over the last year and that will happen over the next year that would have seemed impossible three years ago, four years ago. When you and I met, I was I was a different person mentally, physically, emotionally, and that continues to be true. I want to live in a state of positive momentum and change, and I feel like life is accelerating in that direction. It would not have been possible just 12 or 18 months ago. I love everything about that. I mean, I'm a big proponent of what is possible when you start believing in yourself. I think I try to you know embody that as much as I can in myself. And when I meet other people, you are the perfect example of really going from the lowest of lows to, in quite a short amount of time, adopting practices and habits and all sorts of things that allowed you to get to where you are now. Can you tell us a little bit about the real estate deals that you're doing now in San Diego? Yeah, so probably most people listening will never have heard of what we're doing because it's It's not storage. It's not multifamily. Yeah It's not RV parks, which seems to be what most people are into. We purchase single-family homes and leveraging the ADU legislation or the additional dwelling unit legislation that exists in California, and particularly in San Diego, we convert single-family homes into multifamily investment properties. And the real tailwind, the power that we have in that is that we are vertically integrated. We have a brokerage property management construction company. So from the time that a deal lands in our lap until we disposition it, we control the entire process and the costs associated. And so we can acquire and build a property for around $350 a square foot and anticipate exits at $700 to $1,000 a square foot on the backside. So it's a very powerful equity play. It's not a cash flow opportunity, but if you're wanting to build momentum and equity in your investment portfolio, it's one of the best solutions. solutions that I've seen. Yeah, I mean, I've looked at your packages and your returns and it's very appealing, I have to say. Very awesome that you have all that going on. Now, you are also a father of many children, not just a few, right? So, and now grandchildren as well, right? So what sort of things are you doing to balance? I know you mentioned earlier how you you know were at work all the time at your lowest point and you missed all these years with your children, so now as an entrepreneur and a successful real estate developer at that. How are you balancing life and work and spending time with your family? Yeah, so to clarify, I like to tell people I only have eight kids when they ask. We have one grandson, we have a granddaughter on the way, and you know, that shocks people. I can't imagine life without any of them. And I did a very poor job of being present for the first 20 years. I would say it was a solid F in the the dad grade book. And I've had to have those difficult conversations with my older kids and we have had those. So, you know, the the first thing is being willing to own what you could own and being willing to apologize. And I've had those conversations with my adult kids and saying, you know, I I was doing the best that I knew how to do and I wouldn't do it the same now. And I'm just sorry that I missed so much. That's not how I want the rest of our relationship to be. And if you'll work with me on that, we'll try and make it better. And it's still a process Us of improvement on my vision board for this year is a picture of a dad with a kid and in the background is a calendar. I want to make sure that time with my kids gets on my calendar because no matter what you say, if you say you have a goal to go to the gym or spend time with your family and it's not on your calendar, you're just lying to yourself and everyone else. And so it it has to be on the calendar. And so I am intentional about putting date nights with my wife on the calendar and putting time with each of my kids on the calendar. I gamify it with my habit tracker, where I have a habit tracker alarm every week to call or text my adult kids that don't live at home. And I have a goal around that, that I want 300 out of 365 days, I want to have been in contact with them in some way. And so I track that. So I I set the intention, I monitor the action, and I hold myself accountable for getting the result that I want. Absolutely love that, and I love that you gamified it, but that is the world that we live in nowadays. right? With everyone's attention span being what it is, I think that if it works for you and if it's a hack, you know it will probably help somebody else as well. All of that being said, you know if somebody was trying to emulate sort of where you've ended up in life with real estate developments or even the family or or anything like that, you know what kind of advice, what piece of advice do you have somebody who's looking to get into doing what you do? Be more kind to yourself. So as I as i train people now, as I coach people on vision and identity, what I teach is the first thing is learning how to love yourself. I think that happiness is the key to success and the key to happiness is learning how to love yourself. And so that for me is the foundation, is learn how to love yourself, every version of yourself, even the dark, ugly, scary parts that you don't want anyone else to see, you need to learn to love that version of you be grateful for the experiences that made you into that person. It's possible and it's sometimes difficult to do that. It's still something that I work on. Beyond that, it's deciding what you want your identity to be. I am very passionate about I am statements and affirmations and I don't think you can outperform your identity and so you need to decide what your identity is going to be and wrap some really positive visualization and I am's around that. I'm on a health journey That health journey for me is on my vision board, but it's also something I tell myself every day. I am healthy. I am choosing to track what I eat. I choose to go to the gym every day. So that's the next thing is your identity and then your choices and then how do you feel about those things. And if you can be really intentional about deciding who you want to be, what you want to do and how you feel about it, I think you can accomplish anything. And and so that would be the last piece is learning to believe in yourself and trust your intuition. If you feel called to going into real estate or multifamily or. you know farming, or whatever the thing is you're called to do, you need to be able to trust that intuition and just go for it with all your heart, mind, and soul. And I don't think there's anything that you can't accomplish. Just go for it, believe in yourself. Most people never believe in themselves enough to just take that first step, take that real action, but if you just start, you will end up there. So what do you have as far as future outlook? What are the the next plans, what does the future look like for Mr. Allen Underwood? Well, I can just walk you through my vision board for what that looks like. So the first part is that on a daily basis, I am centered. I am. Taking time to be in the moment and live in the moment. I practice some form of meditation every single day so that I can be present with myself and connected to what's going on around me. The very next thing is relationship with my wife. I want this year to be the very best year that we've ever had. We've been married for 25 years and I just see exponential growth there. So I have some goals around how I can improve, which will help to improve our relationship. Primarily that's around communication. I don't do a great job of communicating verbally with her. And so that's something I want to improve. My health is next. I have goals wrapped around that. I envision myself as a keynote speaker and coaching high-performance individuals to higher levels of achievement. So that's something I'm working on and accepting invitations to do. Also, explosive exponential financial growth. This will be the best year financially of my career, of my life. Part of that is connected with our capital company. Our goal is to raise $20 million million dollars and get to 150 million dollars of assets under management. That's aggressive and it's exciting and it's also achievable with the right team, the right people, the right connections. And so we're working on that and then spending intentional time with my family, with my kids, having many adventures with them. We plan on seeing Sequoia National Park and Yosemite and taking everybody to Banff this year. So there's some great things ahead. I I think the future is bright and exciting. I'm excited for the opportunities that there are. And I think if we take time to pause and reflect and really look at the world, there are, regardless of what the economy does, what politics does, there are opportunities out there for people to thrive. Last question for you. Do you have any books or podcasts, tools profoundly impacted you that you just feel the need you have to tell others about? There are several books that I love, some that I revisit. A classic is Think and Grow Rich. I'm learning to love that all over again right now. Another one that I've loved that teaches similar principles is The Wealthy Gardener. And one that I've read recently that was really impactful was Yes, Yes, Yes Hell No. And it creates a, provides a framework for making important decisions. Impactful right now, again, I do a lot of reading, so the impactful one right now that I'm reading is Buy Back Your Time by Dan Martel and learning how to implement those practices so that I can achieve my other goals without sacrificing progress professionally by bringing in the right team to support me in the things that they should be doing and allowing me to do the things that I want to do. 100%, that's pretty much my whole thesis in life, buy back your time. make some money and spend it to do all the things that you don't want to do, have other people do those things. So I love that. And Alan, thank you so much for being on the podcast. Where can the people find more out about you? Pretty easy to find, LinkedIn or Instagram, The Alan Underwood. I think that's true for Facebook, LinkedIn and Instagram. Momentum Capital Group, you can find us online there. You can Google me. I enjoy being on podcasts and I've had the privilege of being on some really great people like yourself. And I'm pretty easy to find I think if you can't catch me on the ground then you just have to look up I'm probably flying over you somewhere thanks so much all right thanks Michael