The Mello Millionaire with Tommy Mello

Fail Forward: Ari Rastegar on Lessons That Built an Empire in Austin

26 min
Oct 3, 20257 months ago
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Summary

Ari Rastegar, founder and CEO of Rastegar Capital, discusses his journey from humble beginnings to building a billion-dollar real estate portfolio in Austin. The episode explores his philosophy on failure as a learning tool, relationship-building strategies, and his investment approach focused on recession-resilient assets and sustainable growth rather than chasing maximum returns.

Insights
  • Failure is a prerequisite for success—reframing setbacks as learning opportunities compounds over time into exponential growth
  • Authentic relationship-building through genuine questions and personal vulnerability creates stronger networks than transactional networking
  • Real estate success depends on understanding human behavior patterns and demographic migration trends rather than predicting unpredictable markets
  • Building business value should precede personal wealth extraction; generational wealth comes from company valuation, not annual draws
  • AI will become ubiquitous infrastructure (like electricity) enabling productivity across all sectors, not a standalone technology trend
Trends
Sunbelt population migration driven by lifestyle values (water, nature, live music) and physiological/spiritual attraction to coastal regionsShift from high-risk, high-return investment strategies to singles-and-doubles approach with superior downside protection in uncertain marketsReal estate cycles becoming more predictable and timing-able through debt cycle analysis and historical pattern recognitionIntegration of AI as foundational infrastructure across real estate operations and business processes rather than standalone toolEmphasis on community-building and mixed-use development over pure asset accumulation in real estate investment thesisCoastal cities maintaining long-term value advantage over inland markets due to physiological human attraction to water and salt environmentsSeven to nine-year real estate fund cycles creating strategic windows for Sunbelt investment positioningVoracious reading of literary classics over personal development books as superior method for expanding possibility-thinking and vision
Topics
Multifamily residential real estate investment and developmentRecession-resilient asset classes (multifamily, office, industrial, self-storage)Real estate portfolio diversification across 38 cities and 13 statesCold calling and relationship-building sales strategiesInternal rate of return (IRR) targeting and downside risk protectionAustin real estate market dynamics and growth catalystsFailure as a learning mechanism and business philosophyAuthentic relationship development and networking strategiesGenerational wealth building through company valuation vs. income extractionAI as foundational infrastructure and productivity catalystPopulation migration trends and demographic analysisSunbelt vs. coastal city investment positioningReading and personal development through literatureTime management and strategic delegation in scaling businessesCommunity-focused development and mixed-use real estate projects
Companies
Rastegar Capital
Ari Rastegar's private investment firm with billion-dollar portfolio across multifamily, office, industrial, and mixe...
KPMG
Downtown Dallas office building (former headquarters) that Rastegar invested in and used for cold-calling financial a...
People
Ari Rastegar
Founder/CEO of Rastegar Capital, dubbed 'Oracle of Austin,' built billion-dollar real estate portfolio from $3,500 in...
Tommy Mello
Host of The Mello Millionaire podcast conducting interview with Ari Rastegar about real estate and wealth creation
Warren Buffett
Referenced as example of compounding wealth over time; made 99.9% of wealth after age 70
Gabriel García Márquez
Author of 'One Hundred Years of Solitude' recommended by Rastegar as essential novel for expanding possibility-thinking
Fyodor Dostoevsky
Author of 'Crime and Punishment' and 'The Idiot' recommended as foundational literary works for personal development
Charles Dickens
Author of 'Bleak House' cited as example of how great novels teach history, psychology, and human relationships
Robert Kiyosaki
Author of 'Rich Dad Poor Dad,' foundational book that shaped Rastegar's understanding of making money work for you
Napoleon Hill
Author of 'Thinking Grow Rich,' given to Rastegar at age 14-15 as foundational personal development text
Peter Diamandis
Referenced regarding AI and technological disruption trends in conversation about future of work
Bill Gates
Quoted prediction that people will decide whether to work in ten years due to AI advancement
Elon Musk
Referenced for developing humanoid robots for household tasks as example of AI application
Nikola Tesla
Historical figure in electricity/power distribution wars; example of innovation being suppressed by capital interests
Thomas Edison
Historical figure in electricity wars; competed with Tesla and Westinghouse for power distribution dominance
John D. Rockefeller
Referenced as historical figure in electricity/power distribution competition during industrial revolution
John P. Morgan
Historical figure who shorted Tesla's stock and bought trade barriers in electricity distribution wars
George Westinghouse
Historical figure who partnered with Tesla on AC current technology in electricity distribution competition
Quotes
"The only thing that I've got really good at at this point in my life is failing and I promised myself that if I ever got to the other side I would tell the truth"
Ari Rastegar
"Real estate at the end of the day is about people"
Ari Rastegar
"Money is a tool and it matters who's holding it and how that's actually facilitated"
Ari Rastegar
"Reading the greatest novels in the world expand your possibilities. You're not just reading a book, you're studying a time in history, social commentary, vernacular, psychology, and relationships"
Ari Rastegar
"Build a business that's worth a lot of money. Don't think about getting rich every year based on the draws you're taking from the business"
Tommy Mello
Full Transcript
The only thing that I've got really good at at this point in my life is failing and I promised myself, you know at Johnny Rock It's one day that if I ever got to the other side I would tell the truth and the truth of the matter is this Experiment experience, which is this life that we're in now the other side of the coin is failure Contrarian resilient trailblazing Our guest today is known as the Oracle of Austin for his bold approach to real estate and wealth creation All success is about inertia is about action Ari Rastigar is the founder and CEO of Rastigar Capital a private investment firm with a portfolio built around Recession resilient assets including multifamily office and industrial properties to me failure is learning how to win his career path has been anything But ordinary he went from flipping burgers to becoming a lawyer to launching his first real estate investment firm while still in law school in 2006 today He's built a reputation for spotting opportunities and scaling them into long-term success You know real estate at the end of the day is about people while some investors chase trends He focuses on assets built to weather downturns and thrive when the market gets tough. This is Sustainable growth based upon solid fundamental economics Ari believes that the greatest returns come from thinking differently and playing the long game Get ready this conversation will change how you think about risk resilience and rewriting your own path to wealth Okay Guys welcome back to the mellow millionaire today I'm in Austin traveling actually for work and going on a hunting trip and Ari was nice enough Rastigar to be on the podcast So Ari is the visionary founder of Rastigar property company a real estate investment firm redefining how people live work and thrive Dubbed the Oracle of Austin he built a billion dollar portfolio spending from multifamily Office and mixed bases with a focus on innovation and sustainability So you are born and raised here you started out with the three thousand dollar loan Ten years ago, and you built just a massive real estate portfolio. Tell us a little bit about the story I'm an attorney by trade, you know, but it took me a while to to get to that I didn't want to even go to college between you and I and my dad said, you know being an Iranian immigrant and having the Dictatorial typical Iranian father said after you become a lawyer you can be an exotic dancer for all I care Didn't do too well in middle school or high school at a terrible speech impediment and kind of uncomfortable in my own skin and Had to go to a couple community colleges before Texas A&M was kind of dumb enough to let me in but I graduated number one in my class and Delivered pizzas all through college and was you know, trying to trying to get it together and then And then while I was in law school, I was Building single-family homes like in between, you know in between classes and little houses that I used my scholarship money to buy a little lot for 3500 bucks and met a local builder and you know, he built it and helped me get a loan and I was on the construction sites in the morning and in class in the afternoons and It was something and now Where are you at today? What are you looking forward to doing? Well? Real estate is about people and that's really what I love. You know as a corporate litigator Before and just seeing people on the worst day of their lives every day wasn't You know wasn't something that that interested me too much But building community is really what is really what I love But we're we designed this beautiful futuristic multi-family Single-family home little Texas Town Square new elementary school that actually just opened in August And just how there's this 60 acre of green space That really holds that community together Is the thing is that we really really love and you know, we we've built a lot of different stuff from industrial facilities To apartment complexes. We've owned apartment office self-storage. I'm pretty sure we've invested in 38 cities 13 states and just about every asset class and I guess if you build If you build everything that we own today meaning on the hundreds of acres of land and if you build all of it It's worth a little over 10 billion. Wow, and I own a hundred percent of the company and never took corporate capital at the corporate level There's like this unspoken rule that nobody will give you a billion dollars in equity To start and so we just passed our 10 year in business mark in February And so over the next six to nine months, we're gonna start having some dialogues to To go do something fun. So what kind of internal rate of return do you try to shoot for? We're we're singles and doubles guys, you know We're we're not shooting for the moon and the downside risk protection is way better Yeah, is what we look for and so if I can make you know between a 16 to an 18 IRR and effectively what that means to your point is the average return that you make on a yearly basis, okay? And if you look at our audited track record We've been able to do that in some very difficult markets I mean cove it a bunch of stuff that people can complain about but therein lies the opportunity so to speak But we're not looking to make huge Returns because making huge returns means you took huge amount of risk 100% so in the beginning you didn't have access to none of this stuff and you made a lot of cold calls What's one cold call that changed everything for you? I made so sitting in an office great question So I had invested in an office building in downtown Dallas Through another operator and that's really as I said we started in the business I knew a bunch of great real estate guys for my time in New York City and I was fortunate enough for them to give me allocations and the stuff whether the apartments they were doing storage They were doing office. They were doing So we took a sliver of this building that used to be KPMG's Headquarters a big accounting firm. I basically made a list of all the financial advisors They were in the Dallas area and I was you know calling, you know 50 60 70 a day and we you know kind of branched out and You know there's a lot of Lot of long long long phone calls that lasted, you know three to five seconds and then something very interesting happened after about six weeks of making hundreds of dials a day that the rest is history So how did you get in the right rooms when no one knew your name? I mean is that just grit? Yes, yeah, and I would go in New York City to this Italian restaurant called Il Milino I got to know the bartender his name is Elvis and I'd go sit up there and Being a big tipper goes a long way and Whenever wealthy people would show up they'd call me and I'd go up and I'd sit at the table and it would be these these Situations that were curated that seemed to be serendipitous and seemed to be Happenstance, but they were cultivated and so they were cultivated you got to meet them talk with them and getting to know All the people at these places you become a regular and when those people start to like you and then other people there start to like you Something happens when you create an aura in a situation where several people like you Strangers very quickly alchemize it to friends and if you can create a situation where you're around people that genuinely love you and They're gonna go tell all the thing all you have to do is not in smile So how do when friends influence people let the people talk more smile more be there for them How do you feel like you're able to really develop a relationship? Because that's a lot of people say I got a lot of friends and it's very hard once you get over like 20 I don't have that many friends and all my best friend is in the other room We've been friends in seventh grade and he's the chief of staff of our firm But there's a big difference between friends acquaintances There's buckets of how those work asking genuine questions about people that I could potentially have a commonality with Is how you create and build a friendship or build a relationship? But it starts by asking a meaningful question and When they give you a meaningful answer Dovetailing that with sharing something personal and that compounds over the course of 30 minutes 45 minutes an hour You do that four five six seven times You start having commonality and once you have commonality you have empathy and when you have empathy you have everything I love it. You know, there's two guys that come to mind John rule and roll giftology passed away Steve Sims just passed away wrote a book called blue fishing at both these guys We're really good at building relationships And it's just these little touch points that I'm trying to get better at with the people if you intentional with your relationships It all been so many doors building really authentic relationships is a text message a couple times a week of hey, bro What's going on? You know, what's the latest or something versus some grandiose? Jester we know once a quarter or some, you know, some, you know, sterile Impedant email to all of the people well, you know, the real deal is I catch up with buddies Sometimes I Unfortunately go a year without talking to him and when we get together I tell my friends look I'm busy. You're busy I had one of my best friends in my backyard recently This was like in the last year that we grew up together and I showed him my schedule and he's like dude Fuck that. He's like, are you kidding me? And I'm like, this is the way I like things because some of the things are like do a hundred push-ups call your mom read this book There's so many different elements than just money Yeah, money is on its face is not interesting money is a tool money is a catalyst money and on its own is Absolutely worthless. I've made I've made money. I've lost money But the point is money itself is not a thing. It's an illusion that it's a thing It's a tool and it matters who's holding it and how that's actually facilitated I've had billions and billions of dollars go through my hands throughout my career And I'm just getting started between you and between you and I but it's also like you said like everything in nature is Busy everything the birds the bees the plants the trees everything is busy So not being busy with some sort of action You're neglecting your part in the whole I always see readers are leaders when I was Starting my business when I was 22 I met this CPA that only worked with 10 clients very wealthy clients and he's like dude I like you he's like I'm gonna give you tips along the way He's like I might even work with you. He's like but you got to do me a favor He's like, what's the last book you read? I was like kill a mockingbird I think in 11th grade and he's like well, listen, this is called the emith revisited go read this hit And then he gave me the richest man in Babylon and then I went back two days later And he gave me the ultimate sales machine by chat homes and those were the first three books It got me obsessed with reading it. I was like, I didn't know books like this existed So I'll tell you a story my daughter when she was in kindergarten my oldest daughter They were had that point in the class when they say so, you know, what does your mommy do? What does your dad do and they'd go up and you know, I know the teacher obviously very well and she goes up there and very proud Said my daddy is a reader So it became this thing I am a voracious reader and There's no limit to the amounts that I read but I'll tell you something as a Lifelong personal development, you know a guy like you because I'm a nobody from nowhere like whatever I am I I built this guy out of nothing and there wasn't much to work with between you and I But what I can tell you is as an English literature major, okay? Reading the greatest books in the world was my profession effectively And I have found there to be more substance and more expansion in reading the best novels in the world Than reading any of the personal development books, for example Give me give me your time three. Oh another well I'll tell you if there anybody is listening to this that has not read hundred years of solitude by Gabriel Garcia Marquez Or if you're in America and have a red Moby Dick Dostoevsky crime and punishment the idiot check off Dickens You're you're doing yourself an injustice and the reason I say that is reading the the greatest novels in the world Expand your possibilities. What do I mean by that? If you study if you read Dickens you read Bleakhouse as an example You're not just reading a book. You're studying a time in history when it was written. You're seeing a social commentary You're reading a vernacular from a particular city country state. So you're getting a history lesson You're getting a human psychology lesson. You're learning about relationships and by digesting that deep in your subconscious You're expanding your ability to dream. I want to ask you three questions that are repeats I got a million questions here. So we're we're gonna go over time a little bit What's one piece of game-changing advice you wish you knew in your 20s? I'd be telling myself that in this particular's Time space time is much more limited than Then I treated it at the time at that age I Thought that I had all the time in the world and I thought time was moving slow I went to I went to classes I came back and I found myself sitting around a lot even though I was working in those I was studying And going back and looking at the things that could have been done with a little bit more intention I Would have compounded into something even more profound you look at Warren Buffett that has the All the accolades and then just the name itself creates something he wasn't a billionaire to his 65 years old He's made 99.9% of his wealth after 70 the greatest thing he ever did is live to 95 Well, it's true people underestimate what they could do in 10 years But they all estimate what they could do in a year I think so much of the very hard work that I that I have done in my life And I'm no stranger to sleeping in my office for days at a time, you know when my kids were young I would Go home at some point and be out at the office and not see them awake for days at a time You know working those frenetic hours is very much in my DNA But looking back seeing how bad of a strategy that was in in hindsight If I would have started a little bit earlier the smaller little bits of the effort My own work so to speak could have turned into and could have turned into strategic delegation much earlier If you were to start over tomorrow with 10 million bucks, what would you do with it start over with 10 million bucks tomorrow? I would spend at least a year Traveling the world and during that one year I would spend a year planning the next 10 years and I would do that in a capacity in different cultures different climates eating different foods experiencing different body movements and I would go and use that time to Really really plan feel emotionally spiritually physically things that I had not felt before To awaken parts within me that had not been awakened and then from that place be comfortable walking into the unknown and letting the plan on the 366 day dictate what I was gonna do It's very interesting. I love that I think a lot of people you get caught in this trap of comparison and just a lot of people and If you get on social media, which I do it's probably a mistake, but I got a post all the time This is kind of nature the beast, but This can't believe how many people just have nothing better to do than insult other people and get into debates with people They've never met only only miserable people do that 100% only miserable people do that and at this point in my life finding a place of Actual love for those situations really changed the way that I look at my life and for most of my life I would consider myself a pretty angry person. Yeah. Yes Mad at myself mad at the world feeling entitled Something was owed to me my family in Iran were Very powerful to say that the absolute least and came over and started over we weren't Muslim They killed our whole family And so there's a and is the story of a lot of Iranian Americans That are here in Texas, California You kind of knew that Austin was gonna be explode. You also knew in 2006 that Storage was gonna be a good industry. You kind of are able to see things before they happen. What do you think? What are the signs? Austin is a town on steroids. It's not a city grew up living in Dallas Going to law school in San Antonio. We don't say the H were these are metropolis. Okay, they're built with infrastructure highways They're expansive Austin has real geographical barriers You know It was a little sleepy hippie town It was music, you know music hippie town nobody really dissipated Austin I Know in hindsight there have been some very Flattering things that people have said about our thesis. I wish I could tell you I was as clairvoyant then As it has appeared to be But the truth the matter is people have certain core Values that make them spend money Water is one of them nature is one of them and live music So meaning there's these tribal things With this two million year old reptilian brain that sits up here and the behavioral aspect of humans as unique and interesting as we all like to believe that we are We're not we're amazingly similar and amazingly repetitive and amazingly predictable If you look at the the cycles that go through real estate Look at the debt cycles that happen through global economies you can almost time them to the day Of how they will repeat themselves keeping things as simple as possible But no simpler has been our guiding our guiding principle along along the way But what are your thoughts with AI is? Probably I mean, I don't know if you know Peter de Amontez and what's going on or just this idea But I do believe Bill Gates. I mean he said in ten years you're gonna decide if you even want to work Next year Elon Musk is coming out with his robots. That'll do cooking walk the dogs simple things around the house And you talk a lot about technology your big fan you told Forbes you embrace technology because you're a hybrid What do you think we're going? the way that I've been Taught about artificial intelligence an example is the same way you would look at electricity Meaning it's not a separate thing the right now. It's being one-dimensional eyes as a thing artificial intelligence is over here, but in fact it's gonna become the underpinning and an activation catalyst point for all the other things as an underpinning not unlike electricity electricity turns on these lights turns on these things so we don't think of electricity as much as its own Thing because it is now become ubiquitous through everything that we do that's the place where AI is coming So in this fourth industrial revolution, it's the equivalent electricity Just so you know was like the Facebook of its day It was a fight between you know between Cornelius Vanderbilt between JP Morgan between Nikola Tesla and Edison John Westinghouse who is actually the one that had AC current with Tesla before JP Morgan shorted the stock and bought all the trade bar is fine. It's again not its own thing as much as it is a Catalyzing piece that everything else is gonna sit on sit on top of to enhance its productivity And as that productivity hybrid changes things things were evolved just like there's no yellow pages anymore There'll be something else that'll that'll come that'll come beyond that so I believe this is the most interesting and exciting time To ever be alive for so so many reasons But technology I think at its best is an extension of humanity I'm gonna go through a rapid fire Questions here. What's the first real estate book every entrepreneur should read or book in general? If you're if you're listening to this podcast and you're starting your entrepreneurial journey in real estate Is something that you find to be interesting? I love the first rich dad poor dad. I read it the first time when it's a you know, 13 year old boy You know reading that book the first time Just putting it in a perspective That I could digest I could visualize I could see the difference between making money work for you versus working for money And then when my father gave me thinking grow rich at about 14 or 15 years old that foundational piece Drew the thing Drew it all together, but I think anybody that is on this journey and has an Appetite back to that word of hunger, whatever that means spending time Reading the best novels in the world pick one go back to Huckleberry Finn I does it in any book that you that is a book. I believe will expand Your capacity What's the most expensive lesson you've learned that I learned was the Astronomical price of procrastination Last question before we close out the Sunbelts or coastal cities. Where's the smarter bet right now? so the Sunbelt as a region has population Migration trends on its side for now People will migrate to beaches as they have for a variety There's energetic reasons even having your bare feet in sand has a grounding mechanic that you know Actually heals your body and there's a certain part of us being salt water and The way that the waves in the ocean move is by following the moon because it's the largest closest thing to it So waves follow the circle the moon. That's what the ocean exists. You are a salt water being the whole Universe and this is what I tell people stop acting so small the whole universe is inside of you quite literally So because of that there is a gravitational pull quite literally to the coast why say the framework matters most real estate investment funds Are on seven-year cycles and with two one-year extensions seven to nine years in the seven to nine year The only place to be is in the Sunbelt Period hard stop if we had this question on the on the larger debt cycle People are gonna be right on the coast and they're just gonna be there the social issues California, New York Mamdani is irrelevant because the gravitational physiological Spiritual pull that we have to oceans will make coastal cities valuable across the world to the end of time. I love it What's your book called the gift of failure? The first line of the book is I hope you fail. I hope you fail a lot That's all I've known how to do the only thing that I've got really good at at this point in my life is failing And I promise myself, you know what Johnny Rock is one day that if I ever got to the other side I would tell the truth and the truth the matter is that this this life this Experiment experience which is this life that we're in now The other side of the coin this failure I Always say when I get on stage, I'm probably the biggest failure in this room I just fall forward a lot and I embrace it. I'm gonna have you close this out on anything You want to talk about to finish a sub Right now at this moment, there's so many things that are going on in the world that are forcing people either to wait because of uncertainty Whether economic uncertainty global uncertainty. There's so many reasons right now if you read the You know read the the headlines which are only designed to draw attention. That's all headlines and all the the the Media I should say is designed to do tick-tock. It they're buying attention now There's an algorithm for how much your attention costs quite literally I Would take a moment To close your eyes and sit in silence to close your eyes for a second and sit in that divine silence and listen All right, you're the man. This has been a pleasure. I need to go sit down and Close my eyes more Thanks so much for listening to this episode like always We're gonna close it out with the Tommy truth Which is a little slice of wisdom for me to you that can help guide you in whatever you're striving towards right now One of the biggest mistakes I see with young entrepreneurs is they're trying to grow a business into a lifestyle business What happens is a lot of the people say I want these things now. I want to buy a nice house So I got a larger mortgage. I want this nice car So I got a bigger lease or rent payment and that's a mistake. You should be thinking about the outcome of the company That's where true generational wealth comes from that's where your mindset should be not how much money can I extract from this business today? SW2 income so just remember build a business that's worth a lot of money Don't think about getting rich every year based on the draws you're taking from the business and that's it guys We'll talk to you next week