John Assaraf reflects on lessons from his 30s, mixing autobiographical stories with practical takeaways. He describes building ReMax of Indiana (mid-1980s to mid-1990s), experiencing health issues in his 20s (ulcerative colitis he credits to mental/emotional factors), two amiable divorces while raising two sons, and a later relocation to Vancouver tied to a business deal that failed due to insufficient due diligence. The central lesson: learn to ask yourself and others hard questions, communicate authentically and confidently, and do rigorous due diligence in business and relationships to avoid costly emotional and practical consequences.
Questions this video answers
March 1, 2023
From 1986 to about 1995 (roughly nine years).
About 85 offices, ~1,200 people, and ~$4.5 billion annual revenue (as stated).
Chapters
Get comfortable asking yourself difficult questions. Get comfortable going deeper. Get comfortable becoming a better communicator. What do I really, really, really feel? What do I really, really, really need to know? What do I really, really want, you know, to find out about? Alright, so do you want some key lessons from my 30s? Here are a few things that I know will help transform your Life. In my 20s I worked my little ass seraph off and it was all about hard work. Of course I was learning, I was upgrading my knowledge and my skills and reading a ton of books, listening to a lot of back then cassette tapes. Like the equivalent of podcasts today are the equivalent of going to a live event. I was learning, learning, learning, learning, learning, learning and working really hard. And as you probably if you watched my last video on my timeline of 20 years old, I ended up sick with ulcerative colitis. Got that under control by controlling my mind. All good, right? Okay. In my 30s, specifically mid-30s, I built ReMax of Indiana from 1986 to 1995 or so, nine years. I built an 85 office, 1200 person, four and a half billion dollar a year company. And I mean learned so much. But I needed to take some time off. So I took a little bit of time off because in that time frame, 1995ish or so, my son Keenan was born and I wanted to be a great dad. If you see behind me, you see my book here called Having it All. I really want to focus on having it all, you know, having money, travel, fun experiences, a great relationship, being a great dad, a philanthropist, a contributor, somebody has know a great life. And I wanted to be extraordinary instead of ordinary. And I knew that I had to put in that little extra. But after I built my first company, I was exhausted. I got into real estate when I was 19. I worked for, you know, almost 20 years or maybe you know, 17 years non stop. Of course I took some vacations, but I decided to take some time off and just be with my, with my son. And so I took a little bit of time off and traveled. And here's the thing that I learned about time. It was great at the beginning and it was like lots of fun. Let's go here, let's go there. With one exception. I was divorced and I had to do it by myself. And I would have to, I wouldn't have to, but I invited my friends, I would pay for my friends to go on vacation with me because you know, I was in my, in my 30s and they had jobs, they had careers, they couldn't just leave. So I would entice them by saying, hey, want to go on vacation with me? I'll pay for your airfare and I'll pay for your hotel. And I did that just so that I wouldn't do it alone. But here's something that was really important by taking some time off to be with my first son. And then I did the same thing again to be with my second son when he was born. Just about 19 months later, I've gotten a divorce for the second time. And here I was, you know, financially successful and pretty much set for the rest of my life because of what I had built with ReMax. And there was an area in my life that I was failing at, right? Two divorces. So I was at the scene of both of those crimes. So I couldn't just keep saying, it's her, right? So I had to, like, really reflect and go, hey, with your business partners, you communicate, you get along great. You make plans, you get shit done, and things are going great. Like, how come you're getting divorced for the second time? Both great girls, by the way. First one, I got married because I moved from Toronto to Indianapolis, and she couldn't work in Indianapolis when I was starting ReMax of Indiana. And it was just challenging because I was out building a company for six, seven days a week. When I got home, I was exhausted. Couldn't give her the time that she wanted to, you know, she wanted to. We were young, you know, I was building something, but she wanted to have companionship. And when I got home, I was exhausted, and I couldn't give more because I gave it all, you know, to Billy, my company. And so we ended up getting divorced. I met another wonderful gal who became the mother of my two amazing sons now. And we got along great, and we decided that we just weren't meant to be married, but we want to raise our children together. And so we decided to have an amiable divorce. Both divorces were amiable. And we did it out of love and respect. And, you know, I think they call it conscious uncoupling now. We just said, like, shit, let's just be fine human beings and love our children and be mature about it and say that this relationship isn't meant to be. To go longer than it has right now. And let's be mature about it. Let's take the high road and respect and love each other, which we have. I've had a phenomenal relationship with my former wife, Stephanie, the mother of my two children, Keenan and Noah. But that was out of a conscious decision to be great parents and co parent and love and respect each other. And so that was that. But what I really want to share with you is when I, when I got divorced, as much as I could spend time with my kids, one son first and the two kids, there was a lack of purpose, you know, for the rest of the time because then they were going to school. And so like my biggest decisions, like where am I going to eat today, what gym am I going to go to, what exercise am I going to do? Can I work out twice today? And there was a, a good feeling about that, that I had that freedom, but I wasn't trading my life for what I wanted, my love, you know, I wasn't contributing in a way. And so I ended up doing a business deal that caused me to move and take my, you know, I moved with my former wife and our two kids to do a business. And the lesson that I want to share with you is I didn't do my due diligence on this deal. I didn't look deep into all of the nooks and crannies of this business deal. And I moved my family from at the time Indianapolis to Vancouver. And I was there for about 10 months only to make a decision that this wasn't the right place for us. Vancouver's beautiful, by the way, but it wasn't the right place for us because the deal that I was going to be the CEO of a company called the founders, just were doing some things that, let's just put it this way, were shady. And I could have found out about that had I been more responsible in my due diligence, asking the deep, hard questions, but I didn't know how to communicate and ask the personal questions to show me evidence of, you know, the bank accounts, the trademarks, the patents and all the stuff that I was told that they had. And they were doing some things that I think were illegal, don't know for certain, but I think we're illegal. And on the surface, everything they said seemed great. And I got so excited in the deal, emotional in the deal, that I stopped thinking, you know, to show the evidence. Now why am I sharing with you the story between the divorce, you know, and the business deal? Remember I said I was at the scene of both of the crimes. One of the things I had a hard time doing when I was younger, 20s and 30s, is really going deep and learning how to communicate authentically, confidently, with certainty, without feeling insecure, thinking that, well, what if she, you know, feels this or says this or what if he or they feel this or say that? And I did that because I was insecure. But I also not confident enough to ask some of the tough questions or have some of the tough discussions that needed to be had in my relationship or with these potential business people. That's my responsibility. Right, it's your responsibility is to be able to have those tough discussions with yourself, to look at yourself in the mirror and ask yourself, you know, what do I really, really, really feel? What do I really, really, really need to know? What do I really, really want, you know, to find out about? Like, what is that? I didn't feel comfortable and confident in myself. I didn't know. I was never taught the art of communication, of authentically expressing and feeling my way through that. So you know what I did? I suppressed my thoughts. I suppressed my emotions. And if you watched the last video, do you remember I shared I had ulcerative colitis in my 20s? Suppression is caused when you don't express. When you suppress, you depress. When you depress, you disintegrate. When you disintegrate, that's your path to death. And us human beings, we must express. That's the nature of our spirit. And when you say and ask authentically, with confidence and certainty, in a kind, loving way, things that you need to say, you ask the questions you need to ask. Then there's this essence of truth and harmony and clarity and consistency, and things just seem to flow. So here's your lesson. Get comfortable asking yourself difficult questions. Get comfortable going deeper. Okay. On, what is it that you're really, really feeling? What is it you're really, really thinking? Get comfortable becoming a better communicator with love, care, kindness, empathy, diplomacy. That's a skill, by the way. That's a skill that I had to learn after the pain that I went through, after some of the failures, after some of the judgment errors that I made. So there's your session for today, and there'll be more packed in my next video what I discovered in my 40s, 50s, and what I'm discovering in my 60s now. Hey, this is John, and if you like that video, watch the next video because it is packed with things that you can do right now to achieve success way faster than ever before.
