The Entrepreneurial Journey to Forever Passive Income with Josh Cantwell – EP 221

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As I was taking my daughter to school for her first day of 6th grade, I couldn’t help but think about the differences between where my family was financially when I was her age compared to where we are now.

To tell the story, you have to know that I grew up in a lower-middle class family on a ranch in Ohio. My father went the traditional route, attended Ohio State University, got his masters degree and started climbing the corporate ladder at Sherwin-Williams. 

Things were very traditional at home in our Irish Catholic family. My parents never cursed around us, we ate our meals together and talked about how our days went—at least they tried to get us to talk about our days.

Things were fine, until they weren’t! Dad ended up losing his job and eventually had to declare bankruptcy. The upside was that it forced him into entrepreneurship. 

His path was very different from mine, but in the end, we both achieved the success and freedom that we always wanted. 

In this episode, I’m going to share two very different entrepreneurial journeys, and the lessons I learned from my Dad that allowed me to fast-track my success in life. I hope these lessons will help you too! 

Key Takeaways with Josh Cantwell

  • How Josh’s father went the traditional route in the corporate world and experienced greater success when he pivoted to entrepreneurship in his 50’s.
  • How his father took over a business and increased his net worth by millions of dollars in 6 short years.
  • Why bankruptcy eventually led his father to his greatest successes and forever passive income.
  • The wild parallels between Josh and his father, and why Josh got into financial planning after college instead of getting into the corporate world.
  • How Josh was able to leapfrog some of the challenges that his father had gone through by learning from those experiences and realizing what worked, and what didn’t.
  • How Josh and his father essentially became colleagues later in life, going on father and son retreats and talking about business, life and success as equals.
  • It’s okay to start small as an entrepreneur. Start small and then grow big.
  • Sometimes the chaos in life can lead you to breakthrough decisions.
  • Level up with commercial deals as quickly as possible.
  • What Josh learned about forever passive income from his father and how they achieved it from different types of businesses.
  • Pay attention to those who have been there and done it. Whether they are coaches or mastermind members, these are the people that you will learn from the most.

Josh Cantwell Tweetables

“There's no better way to learn from someone that's been there, done that.” - Josh Cantwell


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Josh Cantwell: So, hey, guys, welcome back. Hey, it’s Josh. Welcome back to Accelerated Real Estate Investor. And today, I wanted to talk to you for a quick minute about mindset about bankruptcy versus $300 million in assets under management. The reason why I bring that up is because I was thinking today, my kids went back to school, and as I was in the gym this morning, it dawned on me that my middle daughter Alessandra is in sixth grade.


When I was in sixth grade, my father and mother filed for bankruptcy. My dad at probably around 40 years old. I’m 45 as I record this. My dad was probably around 40 years old, 41, 42. He had gone the very traditional route of going to college, getting a job. He went to Youngstown State University. He went to Ohio State. He got his master’s degree from Baldwin Wallace University, which is where I ended up graduating from undergrad. And he got a job at Sherwin-Williams. My dad ended up going through various corporate jobs, kind of working his way up the corporate ladder, ended up getting laid off like a lot of people, especially around this time of COVID, these last two years. And he started and tried to get into the insurance business, tried to get into the insurance business as an individual broker, got his life and health license. That did not take off like my father had hoped.


And I remember we lived in a 1,200-, 1,300-, 1,400-square-foot ranch in Brunswick, Ohio, with an unfinished basement, and no air conditioning. I shared a room with my brother Mark. I would often complain just enough that I would get switched where I could have my own room and forced my two older brothers to share their room. Or my older brother Matt would take me into his room for a minute, we would bunk up. And when I was in sixth grade, just like my Alessandra, who’s now in sixth grade, she literally started sixth grade a few hours ago, my father filed for bankruptcy.


So, I started thinking about the difference between them and the difference in the mindset between where we were at when I was 11 years old and where we’re at today when my kids are 11 years old. And I started thinking a little bit about my own journey as an entrepreneur. My dad really didn’t become an entrepreneur until he was well into his 50s. My dad became an entrepreneur when I was actually in college. My dad became an entrepreneur when he took over an employee benefits company, partnered up with his former partner, a guy named George Dadas. And my dad bought out George when I was just in my early 20s.


And so, from the time my dad took over that business to the time that my dad bought out his partner and my dad was worth millions of dollars was just a few short years from the time I was about 18 to the time I was about 24, it’s about six years, I remember all of a sudden, my parents buying a bigger house. I remember my father buying a third car. He was so proud of the Thunderbird that he bought. He was so proud of the condo that they bought down in Hilton Head. They had a second home. They had a third car. They had a beautiful house on two acres of land. And all of this happened when I was in sixth grade.


Fast forward through seventh and eighth grade, high school, I got into college, it was only about six to eight years later that my dad became an entrepreneur. And during that time, from the time he became an entrepreneur to the time that I was in my early 20s, I remember having lunch with my dad when I was a financial advisor, I was now about 24 years old. I was working downtown. I was selling financial products to people that were three times my age. I was 24, my clients were like 60 and 70 and 75 years old. And I really didn’t know anything. I really didn’t know shit. And I remember getting with my dad, and my dad talking about how he was buying out his partner and he had landed a new client. And that client was allowing him to pay off the note to his former business partner at 3x the pace, three times the pace. So, whatever the payment was on a monthly basis, my dad was making three times the payments to pay off his former employer, former partner, that he ended up buying out. And my dad was so proud of that. The third car, the house in Hilton Head, and all those kind of things.


And I started thinking about the difference between my dad’s mindset when we were in sixth grade and my dad’s mindset when I was 19, 20 years old, and then my mindset today. And I started to think through those comparisons. And when I was in sixth grade, first of all, I was so proud and so happy to learn that my parents even filed for bankruptcy. I wasn’t proud that they filed for bankruptcy, but I was proud because they never even told me. My parents were adults. And I think one of the problems today with adults is that they talk about adult things with their minor children, the air things out on Facebook, the air things out in public, everyone seems to forget what it’s like to be respectful and not have a potty mouth. Everybody, all the adults like to drop F-bombs and swear and talk about adult things in front of their minor children. I’m so proud of my parents that they never did that. Like, I didn’t know that we filed for bankruptcy until probably 10 years after it actually happened. I didn’t know when I was outside playing with my buddies when I was in sixth grade in the backyard, on the swings, playing football, playing kill the carrier, playing baseball. I had no idea why my father was home from work that day, why my dad wasn’t on the job. He didn’t bring it up. We didn’t talk about it. He just went on about his business of filing for bankruptcy, working things out, and then going on to restart his career.


But what got my dad into trouble was the mindset of get a job, save and slave, slave at work. My dad has a master’s degree. My dad was an intelligent guy, really smart. He was actually like the salutatorian in high school. He was like second in his class, but my dad had relied on the corporate job at Sherwin-Williams, the other corporate jobs to pay the bills, and when that didn’t work out and he got laid off and he couldn’t get another job, this was in the 80s when interest rates were kind of coming down from the 70s, this was around 1987, and my dad had trouble finding work. And I remember thinking, like when I found out my dad filed for bankruptcy, just how cool it was that my dad never told us, number 1. And number 2, we were actually that broke. I do remember looking back at my closet, I remember vividly my brother’s closet, and we didn’t have like 47 t-shirts and 37 pairs of shorts and 18 pairs of shoes like kids do today. I had like 10 t-shirts, maybe two nice t-shirts, like one nice pair of pants, maybe two pairs of shoes, it was very, very lower middle class.


And I remember we used to hang out in my parents’ basement all the time, unfinished, would hang out down there with my buddies. We thought it was the coolest thing ever. We didn’t care that it was finished or not finished. My parents would have parties and would have friends over. They didn’t care that it was unfinished. That was just how it was. But the mindset of my father that got him in trouble was the mindset that he was going to rely on somebody else, he was going to rely on a corporate job. He was going to go to work 50 hours a week. He was going to leave at 7:00 in the morning, was going to come home at 7:00 at night, was very traditional. My parents were very traditional Irish Catholic, Irish, Slovak, and Catholic that my dad would get home, there’d be food on the table. We would eat dinner as a family.


My parents would always ask us, like, “How was your day?” And my brothers would say, “It was fine.” The conversation would end, and my parents would look to us, “What was fine about it?”Just like I had to dig with my kids today, but very traditional lower-middle class, but what got my dad into trouble was the concept of, I’m going to work for someone else. And then when my dad bettering himself just a short six to eight years later after filing for bankruptcy, all of a sudden, my dad took a business that was again in the insurance business. And I think here’s one of the lessons I want to give back to you is the thing that my father got him into trouble, was losing a job and starting his own insurance agency and he was basically like an individual broker producer, didn’t really have a lot of leadership, didn’t really have a lot of connections, was kind of trying to do things on his own.


So, the first mistake I think he made was relying on someone else in a corporate job. The second mistake I think he made was the fact that when he started his insurance business, he did it all by himself. He did not have a corporate structure. He did not have training. He did not have leadership, but all of that led to the springboard of him learning the insurance business, getting into the commercial insurance business, and ultimately, into employee benefits, where his company was insuring companies that had 50, 100, 500 employees. They were doing all their benefits planning, health insurance, life insurance, disability insurance, eye, dental, vision, all that kind of stuff. And all of a sudden, my dad found his niche and my dad got really good at it.


So, it was ultimately part of the failure of trying the insurance business that led him to go into the commercial insurance business, that ultimately led him to basically taking over the employee benefits part of the business, growing that to 40 employees, buying out his former boss and his now partner, and then ultimately owning and running that business on his own. Ultimately, that led to the third car, the second home. My dad, when I was in high school, college, him never missing a football game, him never missing a baseball game, him never missing a basketball game because he had the freedom to come and go as he pleased, but my dad passed away this past November. If I could have a conversation with my dad now, he probably would say that bankruptcy and the forced entrepreneurship of bankruptcy, forced entrepreneurship of him to start his own insurance agency is what ultimately led him to the success that he had, so ultimately, what led him to the second home, the third car, etc., etc.


And so, I’ve been very fortunate to have witnessed this in my own home. Sorry if I get emotional here, but very fortunate to witness this in my own home, watching my own father go through these struggles, successes, failures, and then when my dad was retiring, I got to do a number of retreats with my dad where we would just meet up once a month and we would just talk. We would pray, we would reflect. We would journal. We would read passages in the Bible. We would think about success and just kind of talk back and forth, father and son. And at this point, we were kind of like colleagues, at this point, even in my own real estate businesses, we were making half a million to a million bucks a year. I was maybe even making more money than my dad was, but now, I felt like I had a lot to contribute, not just listen, but also to give back to my dad because of all the lessons that I learned from him. And so, we did these retreats. And I kept thinking about my dad’s mindset now that he was exiting the business, selling the business, and winding things down.


And a lot of the things that my father went through are exactly almost a mirror image of what I’ve gone through. So, if you think about it, I got out of college, I did not go into the corporate world. I went immediately to financial planning because I noticed my dad from his success in the insurance business. I wanted to bet on myself. So, I was able to leapfrog the first 20 to 25 years of struggle that my father went through, leapfrog the bankruptcy that he filed when he was 42. And I was able to get into the insurance and financial service businesses right away. I was given a lot of success with that, six-figure income when I was 24 years old. And that’s what led me into real estate, learning and networking with people.


If I reflect back, I think one of the other things I think my dad probably wishes he had done differently was wishing he had networked better or networked more. My dad was not a super outgoing guy. He was not like one of those guys who just go get beers, have cigars, golf. Forgive the recording, the cleaning lady is here, she’s upstairs. So, I think that’s the vacuum, if you hear that in the background, I apologize, but should end here in a second. But my dad would probably say he wished he had spent more time out. He wished he had spent more time with clients. He wished he kind of schmoozed more, networked more, spent more time with other people that would have led to more clients, more revenue, more business.


And so, when I look at my path, I was able to leapfrog a lot of the early struggles that my father had, then I got into real estate. And real estate was very good to us. Very early, we made a lot of money, not only from flipping homes, but we got really good at short sales and pre-foreclosures. We got really good at hosting seminars. We made a lot of money from all of that, but just like my dad filing for bankruptcy, I experienced my own financial challenges and personal challenges by being diagnosed with cancer when I was 35. So, my dad’s bankruptcy at 42, it kind of mirrors my cancer survival at age 35. At 35, all of a sudden, my bank account was dwindling fast. I wasn’t able to work. I was out of work for basically nine months before my surgery, after my surgery, through the diagnosis, the recovery, my son being born, my son having surgery, all those kinds of things.


And that same mirrored lesson of my father going through bankruptcy, I learned by going through cancer, and that I realized that I was going to pivot now, just like my dad was going to pivot into entrepreneurship, he was going to pivot into the insurance business and ultimately commercial insurance, we began to pivot into larger real estate deals and ultimately raising private money, creating a private equity fund, getting into commercial investing and lending all the way back in 2015, and then ultimately, investing as a general partner or limited partner in apartments, and that’s what basically set us on fire, created significant net worth, created significant cash flow, and created ultimately the ability for us to own over 3,000 units in a $300 million portfolio.


And again, I always say this on all my recordings. I don’t own the whole 300, did I say 300,000? $300 million portfolios. So, I don’t own it all. We have limited partners. We have partners in deals, but I am the CEO. I own a huge chunk of it. So, there you go. And I reflect on the mirror image of my father making the decision to start with smaller deals, smaller insurance deals, and ultimately leveling up into the commercial insurance space to then finding his niche in the employee benefits. For me, nearly identical, getting into residential deals, smaller deals, high volume, lots of deals, experiencing cancer, reevaluating, getting into larger deals and getting into commercial deals in 2015, building our private equity fund, and then ultimately our apartment portfolio, getting into commercial real estate of apartments is what’s ultimately set us on fire and allowed us to leapfrog and create this forever passive income.


And so, I look back and I thought, man, this morning when I was at the gym, I thought about the comparison between the two. I’m like, I cannot believe what a parallel there is between my father’s journey and my own, but because I had a mentor because I had someone I could look up to, happened to be my own dad, if you don’t have someone like that in your life, then I would just encourage you to think about, well, where can you go to find a mentor, to find other colleagues, to find people in a mastermind group that you can share with. And I think about at 45 now for me, this is about the same time that my dad was filed for bankruptcy and starting over, but for me, I’m able to get this done probably 20 years before my father did because of the mentorship and the experience and the mindset that my father was able to pass along to me.


My dad was never a super outgoing guy. He was never like a guy that would just constantly be showering me with advice, but I knew my dad was super intelligent. So, when my dad did speak up, I shut the hell up and I listened. And when he said things like, I listened, I took action because I knew he was coming from a position of strength, I knew he was coming from a position of leadership, and I knew he loved me. I knew he cared. And so, those are some of the mindset shifts and some of the mindsets, first of all, I think some of the things to reflect on as far as takeaways. Number 1 is it’s okay to start small. My dad did. I did. Number 2, we both had some pretty significant upheaval, some chaos, some negative situation, him bankruptcy, being laid off, me cancer, that forced us to rethink where we were going. Number 3, my dad created forever passive income because as an insurance broker, he would land a client. The client would pay the premium. The premium would be paid monthly. Am I dead booked that income into his life for the next year or two years, five years, however long he had that client? It’s no different than us owning an apartment building and having a resident move in. They pay the rent. We book that income for the next year, two years, five years, however long that they stay. My dad created forever passive income. I’ve created forever passive income.


And so, I also think about my dad leveling up into the commercial insurance business, and me leveling up into commercial apartments, very similar. My dad’s life, the second home, the third car, the extra time with his kids, the extra vacations every year to Mexico, Hawaii, Europe, California. I was laughing this past weekend– so another parallel that made me think about some of this. This past weekend, I was at my niece’s wedding, and my niece is 27 years old. She got married. We checked into the Marriott at Key Tower. They screwed up my hotel reservation. And since our hotel reservation was goofed up, they upgraded us for free to the presidential suite.


It’s interesting because back when I was in college when we could finally afford to start going on the nicer vacations, my parents took us to California, we went to Dana Point, we went to Laguna Beach. And when we were in Laguna Beach, I remember us checking into the DoubleTree, which was right one block from the beach. They screwed up my dad’s hotel reservation. And it was me and my brother Mark and my parents, my brother Matt had recently been married, so he didn’t go on the trip, and we checked in to the DoubleTree at Dana Point. We were going to go to Laguna Beach, check out the Archos. We’re going to go to Santa Monica Pier. We were going to do the California kind of touristy stuff. And you know what happened? They screwed up our hotel reservation and they put us in the presidential suite, and that was like a 3,000 square foot, massive, like four couches, a kitchen, like three bathrooms, like just ridiculous.


And so, all these parallels are just wild. And I think a lot of them happening is by accident. It’s God’s grace, it’s luck, it’s being blessed. And also, it’s because I paid attention. Like, I paid attention to the leadership, I paid attention to the mentorship, I paid attention to the details, the nitty-gritty, the little stuff. And I tried to leapfrog and bypass the mistakes that my father made. I tried to leapfrog and bypass the things that he did wrong, and I tried to do them just as good, if not better. So, I want to thank my dad, even though he’s in heaven right now, thank him for his leadership, his impact, his grace, his lessons, and those lessons that I could pass along to you.


So, in summary, number 1, it’s okay to start small. Number 2, sometimes it’s the chaos of life that leads you to the breakthrough decisions. Number 3, level up to the commercial deals as fast as possible. Number 4, pay attention to your leaders, your mastermind members, your coaches, people that have been there, done that. If they come from a place of authenticity, they come from a place of transparency, there’s no better way to learn that from someone that’s been there, done that. And listen, along the way, I think one of the great graces, one of the great lessons is confidence. Nobody gives you confidence. Nobody just hands it to you. Nobody gives you self-esteem. You have to manufacture it yourself. You have to create it. You have to talk yourself into it.


And I always thought of my dad as a super, like, quiet confidence. I am certainly not quiet. My wife is super confident. She’s not quiet either, so much so that sometimes we fight just because we both like to talk so much, but it’s confidence no matter how you look back, my dad, and one of the lessons I want to tell you is that as you build your $300 million assets under management, as you build to your 3,000 units, as you build to the next level of your life, as you build to forever passive income, sometimes you just have to manufacture confidence. You have to get into a deal, get into a situation, make an offer, act like you know what you’re doing even when you don’t, and then it comes off as confidence, it comes off as self-esteem. And at the end, you might tell yourself, holy shit, I don’t know how that worked out.


Everybody, believe me. We bought the deal. We raised all kinds of money. I cannot believe that that just happened because you manufactured your self-confidence. Those are some of the significant differences today versus bankruptcy when I was in sixth grade. So, take those away, instill those into your life. And I hope it helps you along your journey. Thank you so much for being here with me today. I just have such a blast sharing the stuff with you. If this resonates with you, let us know. Leave us a comment, leave us a rating, leave us a review. Don’t forget to subscribe. We’ll see you next time.


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