Dana Robinson – Co-Host and Mentor to All Mankind – Opt Out

Dana Robinson – Co-Host and Mentor to All Mankind

6 months ago · 1 minute read

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Who is Dana Robinson? Well, in the world of the Opt Out Life, he needs little introduction. He is the founder of this movement, the author of the book Opt Out, and the “most interesting man in the world.”

For our 19th episode, we’ve turned the tables to feature the deep-voiced co-host of the podcast. Ready to hear the stories of how Dana built his own life of freedom of time and income? How he was worth millions (on paper) before the real estate crash? Or how he went to Bible College long before he was tattooed and renting a villa in Bali?

With his decades of experience from practicing law, investing in real estate, and running or owning a dozen businesses, Dana Robinson is the most qualified person on the planet to serve as the “Mentor to All Mankind.”

Listen to Dana’s story now.


Nate Broughton:                 00:00:02               This episode of the Opt Out Life Podcast from the Opt Out Media Network was recorded here in San Diego and is the Opt Out life story of Dana Robinson.

Dana Robinson:                   00:00:14               Welcome to the Opt Out Life Podcast, the no BS guide to living the modern, good life. Hosted by subversive millionaires Dana Robinson and Nate Broughton, the Opt Out Life Podcast explains exactly how creative hustlers are turning side gigs into real income and taking back control of their time. From their studio in sunny San Diego, the Opt Out Life welcomes guests who are solopreneurs, entrepreneurs, travelers, and creatives who are proof you can choose a lifestyle over money but still make money too.

Dana Robinson:                   00:00:43               If you feel like you’ve been chasing your tail, running the rat race, or stuck in a system that’s rigged against you, we’d like to offer you an alternative here, on the Opt Out Life Podcast.

Nate Broughton:                 00:00:56               Precise setting is never revealed. He performs feats of strength, like freeing an angry bear from a trap, shooting a cue ball out of the mouth of a man lying on a pool table, winning an arm wrestling match in Bali after surfing a killer wave, and bench pressing two young women, each seated in a chair as a cocktail party crowd cheers him on.

Nate Broughton:                 00:01:14               He is the most interesting man in the world.

Laura Maly:                            00:01:16               Our guest is Dana Robinson. He is the cohost of this podcast, author of the book Opt Out, and the real life version of that most interesting man in the world. Dana’s life story includes stints as a pastor, a lawn boy, an attorney, a property manager, a published author, and a full blooded entrepreneur who’s seen inside the stories of businesses as varied as you can imagine.

Laura Maly:                            00:01:38               High end fashion, check. Wine barrels, check. Christian audio books, check. As you’ll hear, we’re only scratching the surface of the man, the myth, the legend.

Nate Broughton:                 00:01:48               I feel like the right time to turn the tables with this episode and let everyone hear about who my sage cohost with that deep voice that makes your body purr actually is and how he managed to go from bible college to being the founder of the modern Opt Out Life. I’ve known Dana for years and benefited from his experience, his friendship, and his mentorship.

Nate Broughton:                 00:02:07               But this podcast, and our growing community with the Opt Out Life is your chance to gain access to a guy whose mission has become one of helping people break free from the life they’ve been sold and to live the life they choose. To help bring you this story, I’m joined by our friend, Laura Maly.

Laura Maly:                            00:02:07               Hi Nate.

Nate Broughton:                 00:02:23               Hi Laura. You want to bring us home?

Laura Maly:                            00:02:25               So how does a guy go from studying and working to be a pastor, to tattooed and living in Bali, working on his book in a year long adventure with his beautiful wife of 20 plus years?

Laura Maly:                            00:02:34               What was his Opt Out, and where’d it all come from? There’s a story here. In fact, there’s a lot of stories here. We’ll do our best to get you behind the scenes, and remember, stay thirsty my friends. Here’s Dana.

Nate Broughton:                 00:02:49               Today on the Opt Out Life, my partner in crime is becoming the criminal. Is that right?

Dana Robinson:                   00:02:55               Where were you on the night of the 23rd?

Nate Broughton:                 00:02:57               Am I mixing my metaphors wrong? What I mean to say, is Dana is gonna be the guest. I’m going to cohost with our friend Laura from episode 17.

Laura Maly:                            00:03:08               Yes.

Nate Broughton:                 00:03:09               She’s back. We’re turning the tables on Dana and we’re just gonna see how this goes. People seem to want to know more about us and we spend all that time shooting those fancy videos and it’s just not enough.

Dana Robinson:                   00:03:21               More. More.

Nate Broughton:                 00:03:21               More.

Dana Robinson:                   00:03:22               Of Nate and Dana.

Nate Broughton:                 00:03:23               I can understand why you wanna know more about Dana. So here’s what we’re gonna do. I’m gonna kick this off Dana. You have a very long resume, we’ll say, in the sense that there is many job titles that you have had that could be applied to you.

Nate Broughton:                 00:03:38               You’ve been a pastor, is that right? Or a minister?

Dana Robinson:                   00:03:41               Yep.

Nate Broughton:                 00:03:41               Okay.

Dana Robinson:                   00:03:42               A pastor. Same.

Nate Broughton:                 00:03:42               You’ve been a pastor, you’ve been an attorney, you’ve owned a lawn business, you’ve owned a property management business, you’ve owned part of an audio book business, you’ve owned part of a shoe company, I don’t know if there’s titles for all these things. Some of them have titles. If you had to pick one to engrave on your tombstone, what would it be?

Dana Robinson:                   00:04:03               That’s so meta.

Nate Broughton:                 00:04:08               This can’t be like a quote or anything. It’s gotta be a title, a trade, something like that.

Dana Robinson:                   00:04:15               I don’t know if there’s a right word for it, but I think the role I’ve played is probably mentor in most of those. As a pastor, I helped people. I was a mentor. As a lawyer, I’m really not there just to prep your legal documents. I’m there to think about the forest for the trees and things you can’t see.

Dana Robinson:                   00:04:38               As a partner in a shoe business, all I could do was bring my knowledge to bear. I’m not a designer and as much as I want to be involved with the designs, George won’t let me.

Nate Broughton:                 00:04:49               Right.

Dana Robinson:                   00:04:49               When I comes to wine barrels, all I can bring to bear what I know and be a mentor to the partner who knows so much more than me about so many other things. And, I guess, what did I do with the Opt Out book was kind of got tired of people asking me, “How do you live this crazy life when you keep saying you’re not lucky and you’re not rich.” It’s my gift right? I’m just mentoring people.

Dana Robinson:                   00:05:12               I’m saying, “Here’s what I’ve done. I’ll just be honest about it and maybe you can do something with it.” And it’s what we’re doing with the Opt Out Life Podcast, I guess.

Nate Broughton:                 00:05:19               That’s right. Dana Robinson, mentor to all of mankind. I can see it now, engraved into eternity. I like it. I like it. Okay, well, Laura, since you’re here to take the pressure off me-

Laura Maly:                            00:05:37               Oh man.

Nate Broughton:                 00:05:38               I know you’ve read Dana’s book.

Laura Maly:                            00:05:40               Yep.

Nate Broughton:                 00:05:40               You’ve been a guest on this podcast. You’ve been a listener of the podcast. I think you’re a very appropriate person to have here as we turn the tables. I know you’ve got your list there resting on your knee.

Laura Maly:                            00:05:52               Always. Always prepared with a list.

Nate Broughton:                 00:05:54               Do you want to jump in or you want me to keep going? Cause I could go all day with this guy.

Laura Maly:                            00:06:00               I guess, I would be curious to know when you sort of feel like you shifted … You’re a mentor, certainly so, but when did you feel like you were shifting from either being a part of more traditional lifestyle or transitioning more into a more entrepreneurial role of things? Was there sort of a shift in your life that took place that that was like, “Oh yes, I can point back to that and say my eyes opened wide then”?

Dana Robinson:                   00:06:26               that’s a great question, and yeah, there are a couple of moments that coalesced I think. When I went to law school, I didn’t go with the mission to become a lawyer, I went with a mission to get a secular degree that would help me to have some value for my time. I was professionally trained with two degrees in theology, so I had no qualifications other than being a pastor, but I had owned a couple of small businesses.

Dana Robinson:                   00:06:48               When I was in college I started a coffee shop and I started a landscape business, but these didn’t qualify me as a business person. I really didn’t have the skill at that point to really think of myself as an entrepreneur. So going to law school I thought would be efficient, it’d be smart to make my time worth something, then regardless of what I was doing as a business person or a lawyer, I would do better.

Dana Robinson:                   00:07:10               I kind of did well in law school and got a decent job, but I was at that job and the partner that had retired was still there. He was this cool guy, sitting in the corner office. It didn’t do much but mentor people. So he was easy to get to know. He wasn’t as busy as everybody else. And, that guy was an entrepreneur. He liked the lawyer label of all things.

Dana Robinson:                   00:07:31               He like that that was sort of his calling card. He owned one of the first wildly successful night clubs in Las Vegas, was a real estate developer, had been a joint venture partner in several very, very large scale businesses and was good at both big ideas and managing entrepreneurial adventures and made venture to guest 10s of millions of dollars, but still liked to be the lawyer guy.

Dana Robinson:                   00:07:57               But I realized in looking at his life that I didn’t have to just be the lawyer guy. He liked that and I didn’t think I would still be calling myself a lawyer at this point, to be honest, because once I kind of caught that, I realized, “Hey, I’d been a little bit of an entrepreneur and now this guy is sort of shedding light on the fact you can be a lawyer by trade, but then make a lot of money in business.”

Dana Robinson:                   00:08:22               That kind of lit a spark and I was at a little enough firm that I could dabble a little bit. There was no prohibition on dabbling in business. The partner who owned the firm actually warned me that it’s dangerous because he had dabbled and had some pretty hard business, I wouldn’t call it failures, but some businesses he had gotten in that had cost him more than he made.

Dana Robinson:                   00:08:42               So I guess, in some sense of failure. But he was a wildly successful attorney, so he knew I was dabbling and he just said, “You know, I’ve dabbled, and just know that you might take some lumps and have to work harder as a lawyer to recover from those.” So I had these two voices in my ear.

Dana Robinson:                   00:08:59               But there was a point where I felt like the firm was going through some transitions and I had to envision myself being there a long time at that point. I was either gonna double down and be part of regrowing this firm through some transitions, which could be rewarding, and it would’ve been, I mean the firm eventually merged with the fourth largest firm in the world and I would’ve been a partner in that firm.

Dana Robinson:                   00:09:23               Or, strike out on my own and through a deal I talk about in the book with the nursery that I had helped a client liquidate, I had a little bit of cash for the first time, ever really, in my life to play with and also simultaneously ran across a business for sale in San Diego.

Dana Robinson:                   00:09:40               So, I just made the decision that it was now or never. I asked one of my other mentors, the woman who’d been my boss what she thought and I said, “You know, am I gonna ruin my career as a lawyer if I go try and be a business guy?” And she said, “No.” She said, “The deeper you go as a lawyer and the longer you’re in there, the harder it’s gonna be to make the leap and it’s perfectly easy to go out, try your hand at business. If you fail, you’ve got the skills still. You’ve got the experience and the skill. You can always go back holding your hat in your hand and become lawyer guy again. The firms are always there waiting to hire good lawyers.”

Nate Broughton:                 00:10:15               It’s interesting that she told you that. Good on her, for one. But I’m liking this line of questioning and this story because, Laura is right to kind of insinuate that you always seem to be the sagest man in the room. I have trouble thinking of you as a foolish 20 something, let alone a foolish anything.

Nate Broughton:                 00:10:35               So that first fore into business, well that first fore into business after you had become an attorney, or maybe a different story, tell me about a time when you were just winging it and had no idea what you were doing and maybe it worked out and maybe it didn’t.

Dana Robinson:                   00:10:51               Yeah. I mean, my first business, I totally winged it. It was a landscape business. I had really no money. I was in college, second year in college. Married. Married young. And, basically said, “Heather, you can come move to LA if you want or we can just get married and move with me.”

Dana Robinson:                   00:11:06               She’s like, “I’m down. Let’s do it.” And while there, I worked for a year at that job that wasn’t so great and thought, “I mowed lawns as a kid. I could probably do better by just mowing some lawns.” So I started passing out fliers. I had Volkswagen Golf with like a Sears lawnmower that you had to breakdown to put in the back of the hatchback to drive it around to mow lawns.

Dana Robinson:                   00:11:29               That business grew really quickly and then I ended up acquiring another guy’s business so it grew even more quickly and I was still a full time student. In fact, I was taking extra units so I could finish in less time. I didn’t want to be in school longer.

Dana Robinson:                   00:11:42               And, that business grew in the hands of a 20 and 21 year old who didn’t know what the hell he was doing. I had employees, I was trying to figure out how to pay them. I bounced checks constantly because I’d be waiting for the city to issue a check for a landscape I did for the City of Orange. I’d go pick the checks up in person. Walked into the bank and then hoped the payroll hadn’t cleared. I mean, completely winging it.

Dana Robinson:                   00:12:09               And yeah, at one point, a girlfriend of one of my employees lectured me about how horrible I was because I bounced Todd’s paycheck three times in six months or something like that.

Laura Maly:                            00:12:19               Oh no.

Dana Robinson:                   00:12:20               And I always scrambled to pay his late fees and apologize, but I was completely winging it. No sense of budget or really how to run a business. It was just like, think of it as an entrepreneur raised by wolves. I was just the kid who mowed lawns as a kid, doing it as an adult.

Nate Broughton:                 00:12:38               All right Laura, breaking in for the first time to Dana’s story, fun to have you here with me doing Dana’s role and the voice over side.

Laura Maly:                            00:12:46               High pressure.

Nate Broughton:                 00:12:46               Yes.

Laura Maly:                            00:12:47               My voice isn’t as calming.

Nate Broughton:                 00:12:49               That’s true. This is the patented break of the Opt Out Life where we kind of bring people along with the story and what I’ve liked so far is we’ve established what people have probably already known that Dana is the mentor to all of mankind. That he is often the smartest guy in the room. I’ve been in business with him outside of the Opt Out Life stuff and been on a lot of conference calls and then cases and he’s always the guy that you’re happy is there on the other line, or on the line.

Nate Broughton:                 00:13:17               Especially when he’s on your team because you know that if you get to a point where you don’t know what to say or it’s outside of anything you’ve ever experienced, he definitely has something he’s been like, “Well, this happened to me once and I know exactly what to say.”

Nate Broughton:                 00:13:32               He’s paternal. He’s mentor like in that way. And I loved having him around in my life, so I think it was important to establish that point, even though I think it’s pretty obvious from anyone who’s listened to this podcast.

Laura Maly:                            00:13:45               Yeah. I mean, as I’m getting to know you guys better and the first time I met you guys and came in here, it’s very apparent, Dana’s grounded, paternal presence, it definitely fills a room and you can sense it about him and he’s very measured when he speaks. He thinks about what he’s gonna say before he says it, so there’s never any un-meaningful disconnects happening in the conversation.

Nate Broughton:                 00:14:09               And that comes across as very genuine and caring, I think, in the way that he is. But yeah, the background, we got a little bit of his early years in law school and becoming a lawyer. I think we were trying to pick at to see if there was anyone who set him off in the path of … he’s clearly not just an attorney today and I don’t know if he ever just was an attorney even though he worked for a few years in a law firm and was going down that path.

Nate Broughton:                 00:14:31               But he’s told us that there was a few older people in the firm. One guy in particular who did a lot outside of law. Owned businesses, owned night clubs, it’s definitely something you could see Dana doing today, and I think that guy was inspiring. And he also had people telling him that it would be risky to dabble outside of law. To pursue that passion he would be risking time and money.

Nate Broughton:                 00:14:51               And those people that told him that are probably the ones that are still at the firm. I had to ask him if there was ever a point in his life, given what we said now, if he was ever just winging it ’cause it never seems like his, right? He gives this little landscape story, right?

Laura Maly:                            00:14:51               Yes.

Nate Broughton:                 00:15:04               That was cool.

Laura Maly:                            00:15:05               Yeah.

Nate Broughton:                 00:15:05               About bouncing checks and riding around in a Volkswagen Golf. I wish I could’ve met him at that time, just to see him in that state because it’s no the Dana we know today, although those experiences are natural for someone, I guess, who’s come to the point where he’s been a part of every type of business you could imagine and has this experiential framework to draw on.

Laura Maly:                            00:15:23               Yeah.

Nate Broughton:                 00:15:23               Started as a hustler mowing lawns.

Laura Maly:                            00:15:25               Yeah, well, I think the thing that’s most surprising about it, is the age he was for that lawn care business, or the lawn mowing business. He was quite young, still in his early 20s, and that’s an experience that you would assume somebody is going through maybe in their later 20s, mid to later 20s, and based on his, obviously, entrepreneurial spirit, he had something in him that drove him to do it.

Laura Maly:                            00:15:46               Hearing about his learning experience through the bouncing of checks and riding around town in his golf, it was very interesting to realize that he was actually in his very early 20s when he was going through that, which seems something that would be set for somebody a little bit older.

Nate Broughton:                 00:15:58               Sure. Sure. And it illustrates a bit that we all have to start somewhere. And the whole point of this Opt Out Life thing is to make these stories of success as accessible ones that people can start down, no matter where they are in life, no matter how old they are, no matter what skill set they have. It’s a bit instructive there.

Nate Broughton:                 00:16:14               Now, let’s hear a little bit more about how Dana spends his day to day today.

Laura Maly:                            00:16:18               So, are you practicing law now? Do you practice law?

Dana Robinson:                   00:16:22               Yes. I own the law practice. I’m the partner, and I have an associate attorney that’s been with me for five years that does the heavy lifting. So I’m … we allocate work between us.

Laura Maly:                            00:16:35               And between all of the balls that you have in the air, if your life was a pie, how do you slice up your time, or your work time I guess I should say?

Dana Robinson:                   00:16:44               Right. Since … In Bali I sliced it 90 percent me, life, writing, but that was intentionally planned and I spent about an hour a day doing what I needed to keep the law practice going. Since being back, I think of the law practice is my business. I’ve got say, three or four side gigs that are fairly efficiently managed now. They don’t take a lot of time, if any. And then real estate.

Dana Robinson:                   00:17:09               So I’d have say 50 percent on the law side, that’s my business. Quarter or less on side gigs. And the rest of sort of, I call it my economic time in real estate.

Laura Maly:                            00:17:21               Got it.

Dana Robinson:                   00:17:22               And real estate doesn’t actually take a lot of time once you own it, but I’ve been active in the acquisitions. So, it’s been time consuming when you’re acquiring and financing properties, they become very noisy for months at a time while you’re going through due diligence, doing the deal, and then financing. Then refinancing.

Nate Broughton:                 00:17:40               Yeah, a lot of fire alarms. Not just the acquisition financing side, but also early on in construction, in leasing, in things like that. I mean, you just gotta deal with those things that come and they come fast, early on in the deals. And especially the way that you like to do them where you’re getting fences off Craigslist and installing them yourself.

Nate Broughton:                 00:17:59               Dealing with the tenants and getting to know them, that very hands on approach that you take, which benefits you on the bottom line and probably in some other ways, certainly requires some time and attention early one.

Dana Robinson:                   00:18:09               Yeah. So I guess my current time allocation and in the next year, to be honest, Opt Out Life will become my business and the law practice will become a side gig. I mean, the staff I have are perfectly capable of managing more and more of that.

Laura Maly:                            00:18:09               Right.

Dana Robinson:                   00:18:26               So I will bill and make less from it. For example, this year I’ve put dozens, hundreds of hours probably into the Opt Out Life and to building content, podcasting, and promotion and all of that.

Laura Maly:                            00:18:38               So, it seems to me, and this is just perceived, but, both of you kind of have more lone wolf approaches to things as opposed to what Michael and I do, where we have a big team below us and working with us, and on a bunch of different stuff. Do you prefer it this way? Is there elements of it that you like or dislike?

Laura Maly:                            00:18:56               Cause it seems like at some point you’ve had probably a consistent team working with you and things like that. I’m just curious to know.

Dana Robinson:                   00:19:02               Yeah. For the law practice, right after I got back from Bali, I added two lawyers. So I had three lawyers, five law clerks, and a full time paralegal and I made 20 percent less than when I was in Bali with one lawyer and one paralegal and was working one hour a day.

Laura Maly:                            00:19:20               Wow.

Dana Robinson:                   00:19:22               Then we went through one more year of that because I had two very big cases and performed about 10 percent less than that even with my biggest staffing year. From a law practice standpoint, my type of practice is difficult to scale, and I don’t want to build a big partnership with a bunch of lawyers and then add on a bunch of associates and staff under them because the law practices, they’re very difficult to run the Opt Out way.

Laura Maly:                            00:19:22               Sure.

Dana Robinson:                   00:19:52               If you have a lot of layers of staff. Because, when they call the lawyers, that’s with a lot of billing businesses producers, so you need producers, and if I’m one of the producers, I can’t really be an entrepreneur.

Laura Maly:                            00:20:04               Yep.

Nate Broughton:                 00:20:04               A lot of people know you as a lawyer, though. A lot of people in our network know you as an attorney. You’ve done good work for many of them, and I think you’ve done some interesting work out of our friends, out of our shared network, and out of your own network. That network’s not going away, so you’re gonna get a lot of phone calls over the years for people that you probably want to help.

Nate Broughton:                 00:20:24               What do you think your approach will be as time passes, is just to be hand off player to everyone else that’s still left at the firm or picking shoes and maybe jump at a few opportunities?

Dana Robinson:                   00:20:36               Yeah. No, I think that the … Ultimately what I do as a lawyer isn’t far different from what I did as a pastor. You’re helping people one at a time and I think I’m hitting the 20th year, next year, as a practicing attorney. I’m at a point where one of my … my mission with Opt Out Life is to pass on everything I pass on to individual clients every day en mass.

Dana Robinson:                   00:21:02               If I can hand that off to 1000 people or 100 thousand people, or a million people with economies of scale, not as their lawyer, but what most people need from me isn’t me drafting a contract, right? Lots of lawyers can draft and NDA for you for less than I would charge you to do it. What people want from me is the reflection on my life experiences and the collective experiences of all of those clients.

Dana Robinson:                   00:21:28               That’s the benefit that I bring to my clients is, combination of this sort of like life experiences of my own with my 20 years of practicing law, and the fact that every client whose business I’ve touched add to this sort of library of mine that I draw from. And so, as we design, say, courses, I want to find ways to pass that along to people in bite sized pieces and give them what I know most people need when they come to a lawyer.

Dana Robinson:                   00:21:59               It’s not really that they need a lawyer to draft something for them, and if I can provide that, then the law practice, I’ll retire. I’ll essentially hand it off for those that work for me and some probably others and hopefully have mentored them to know what I know and approach things my way and people come. I will hand them off and will not be able to be their lawyer.

Laura Maly:                            00:22:20               So, one of the things that I’m sort of subtly hearing through this is I think Opt Out Life is a lot about money, business, family, transitioning your life so that you can have the flexibility to live it the way you would like to. But one of the threads that I’m hearing in here is like helping people. Right?

Laura Maly:                            00:22:36               Is that something you’re doing consciously? Or is that something that you’re like, “Oh, this is a business opportunity, we should explore this”? Or is this something like, “Oh man, this is just innate to who I am to help other people”?

Dana Robinson:                   00:22:46               Yeah. It’s just how I function, and it’s good and bad. It’s difficult to put a governor on that because anyone who calls, you wanna help them, whether you charge them or not.

Laura Maly:                            00:22:46               Sure.

Dana Robinson:                   00:22:55               You just feel a sense of, “I can help, I should.” That is, I don’t know, probably part of what puts people like me into ministry. It’s part of what puts people like me into jobs that are mentor oriented. It’s a good combination of skills if you have a skill to help people and this sort of innate desire to help.

Laura Maly:                            00:22:55               Yep.

Dana Robinson:                   00:23:17               I don’t know where it comes from. I mean, I’m not, I guess, I don’t know. I’m not inherently altruistic, I’m kind of selfish and care about me. I’ve got an ego and all of that. I want to make a lot of money. I don’t want to be ashamed about that.

Dana Robinson:                   00:23:32               But I was a middle child, so maybe I’m just happiest when people are happy around me. But also, I don’t know. I like when I’ve accomplished things my way. I get a little boost of payout from that and then when people are like, “How do you do that?” I wanna give them the same.

Laura Maly:                            00:23:50               Sure.

Dana Robinson:                   00:23:50               I get a little free ride on theirs if they can do the same thing. In that sense, maybe it’s not altruistic at all. The more people who say, “Wow, I did what you said, and it made me work, it made me improve my life,” that’s a pretty big pay off, even if it’s not financial.

Laura Maly:                            00:24:09               Yeah. I agree.

Nate Broughton:                 00:24:09               You’re getting me more excited about Opt Out Life as you talk. I’m glad we have this recorded. I hope Dan from Moostache is listening, because there’s a lot we can do with that audio.

Nate Broughton:                 00:24:20               But yeah, it’s cool to hear kind of the unvarnished responses to why you’re doing this, why you do what you do, and why you’re the perfect fit to be the guy to give that advice, because you’ve had not only the stories of your own business that have been so varied and across a long timeline, but you got the stories of so many cool clients and businesses that you’ve owned part of as the kind of attorney, investor, equity guy to draw from.

Nate Broughton:                 00:24:50               I think there are very few people on the planet that have that varied experience plus your personality and interest and altruism in helping people. I think it’s special. And that’s why I’m excited for you, me aside, to be doing this. I think it’s cool. It’s right. It feels right.

Dana Robinson:                   00:25:10               It feels right for me. I mean, in some sense, I don’t know. I think, I’ve been involved in a lot of ventures, and for every one, I’ve hoped for the home run. I mean, I talk about base hits, triples, and doubles matter because maybe I have to feel that way ’cause that’s how it’s worked for me.

Dana Robinson:                   00:25:29               But I don’t know, had I 10 plus million dollar home run, would I have settled into the complacency of the next venture of my life? Maybe being in the position that I’m in, which is, I control my time, I’ve got enough, I’ve got the right investments. If things just went the way they were going, I would retire just fine. But, I’m still ambition and I’m pouring my ambition into this.

Dana Robinson:                   00:25:58               So, I don’t know. I’ve grumbled sometimes about some of those ventures that almost went big. Some of the ones that I’m involved with have still … We just got an investment in the shoe business that valued at double the last time. That’s cool on paper, but it’s not putting millions in my pocket. I don’t know. It’s fun to do this, in a sense, while I’m still experiencing the things I’m telling people to do.

Dana Robinson:                   00:26:27               I’m not retired from it, completely cashed out. You’re hearing it while I’m living it.

Nate Broughton:                 00:26:34               Okay, Laura, we’re getting a little further along with Dana. He’s told us a little bit more about his mission at this point in life, and it’s cool because it’s giving people more of a look behind the scenes of the Opt Out Life, maybe explaining a bit of what we want to do here. And a lot of what we’re doing together is driven by Dana’s passion to help people, to spread his knowledges and experience to more people than he can at a law firm.

Nate Broughton:                 00:27:01               I think that’s part of the reason why he wrote the Opt Out book, and I think he kind of said this us was, because people are always asking him, “How do you do this stuff? How did you get this life? Are you lucky? Are you rich?” No. And also, he finds himself in a profession where people are paying for his time one on one to get advice more than you’re paying to get a legal document.

Nate Broughton:                 00:27:22               I think he truly does want to be the person who can make a difference in people’s lives by saying, “Here’s how I’ve done it. Here’s the vast library of stories that I have from all these businesses that I’ve been around.” And the Opt Out Life is his chance to do that now. It’s the right time in his life to do it. I think it’s the right medium to do it and what else can I say about how great this Opt Out Life thing is?

Nate Broughton:                 00:27:43               I’m running out of superlatives.

Laura Maly:                            00:27:44               Well, I think what’s interesting is he mentions helping one person to one person. He felt like he was helping one person a year as a pastor, one person a year as an attorney, and I think what’s interesting about Opt Out Life, is it really puts him in a position to share that passion for mentorship, that passion to help others and do it on a very scalable way so that we can reach, or you can reach, as many people as possible.

Nate Broughton:                 00:28:05               Yeah. I feel almost lucky to have … I’ve mentioned earlier that I feel lucky to have had him on my side, in my court on calls in the past for business. He’s been someone that I’ve been able to go to for 10 years for this sort of advice, and doing this podcast got me straight up excited about what we’re doing in a new way because I’m excited for people to get access to him and their getting that through the podcast, but this other stuff that we’re working on, spending a lot of time building our first course, which is called the Opt Out Life Blueprint.

Nate Broughton:                 00:28:33               We are launching a membership for the Opt Out Life on a monthly basis where you can get direct access to Dana and I through webinars, through office hours, through other content that will not be accessible to non members, and there’s actually a high value to that I think. You’re talking about a guy that charges several hundred dollars an hour for his time as an attorney and you’re actually getting something more broad across his entire life experience with what we want to do with people in the membership.

Laura Maly:                            00:29:00               Yeah. I mean, I can’t tell you just in running our business day to day, our businesses day to day how often I would like to have somebody to reflect ideas off of or to look at in decision making and bounce a couple things off of, so that accessibility and sort of this life blueprint is gonna be very, very cool.

Nate Broughton:                 00:29:16               And, let’s not forget that earlier since the last break he’s told us about his time in Bali and that he actually found that he made more money with his law practice with his scaled down version working less than an hour a day than he did when he came back and had like three attorneys, and five paralegals, and whatever.

Nate Broughton:                 00:29:32               And that’s actually something that happens to a lot of entrepreneurs. I think that’s just a nice example of something that could be a thing that someone who is pretty far along as an entrepreneur and living their version of the Opt Out Life, that they may not be keeping tabs on and it’s hopefully something that the stories on our podcast can bring to light and types of things that you’re talking about where having a sounding board, having someone you can talk to, whether it’s your friend down the street, someone in EO or a networking group near you, or through a platform like Opt Out Life can bring to bear.

Laura Maly:                            00:30:02               Yep.

Nate Broughton:                 00:30:03               You’ve had a lot of paper millions in your pockets, right? I think that as someone who has also felt that at certain points in time, “Oh, I missed that opportunity to make 10 million dollars, or five million dollars, or whatever. If things had only gone this way or if I’d made this investment instead of that one, I’d be so much more well off.”

Nate Broughton:                 00:30:23               If that’s happened to you, you can get kind of lost in that and feeling like you’re such an idiot. You’re the only one that’s ever done that. You can kind of forget that even people who are close to you have those stories just as much or even more.

Nate Broughton:                 00:30:37               What are some of those paper million stories? You don’t have to go too deep, but even a bulleted list, I think people might be surprised.

Dana Robinson:                   00:30:46               Yeah. I mean, the real estate was the biggest because I had invested in a couple of properties with a partner and we had entitled them for high rise before, I guess in ’05 and ’06. There was some frothiness in the market, but it wasn’t as frenetic as when it really peaked in ’07. And we had a sense that we needed to move on those, so we put them on the market and had two properties entitled for high rise in escrow with a buyer who was backed by a pension fund, so a legitimate buyer with resources.

Dana Robinson:                   00:31:18               And on paper, we were taking out 13 million dollars with an underlying cost and loans to pay off of a little over three million. So we’re about split a net of 10 million dollars on a 60 day escrow in the summer of ’07.

Laura Maly:                            00:31:35               Oh no.

Nate Broughton:                 00:31:36               So, you’re what? Late 30s at this point.

Dana Robinson:                   00:31:38               Yeah. So, yep. Late 30s and thinking there it is. I’d spent 10 years sort of hopping from the … Made 10 thousand on this and flipped that and made 30 thousand on that and got into this and made a couple hundred on that. And kind of slowly growing my asset base from literally like 10 thousand dollars I got from hosting a garage sale for my mentor.

Dana Robinson:                   00:32:03               And then, we thought we were done. Thought that kind of cash out is meaningful. That’s … Anything, I guess what I’m trying to teach people in the book is like, “Look, all those other things built up to that and those are meaningful,” and so, when the market, they were about to go hard on a million dollars, they only had 10 thousand hard for the first 10 days, and they maybe sensed something was wrong and they were about to go hard on the million per property.

Dana Robinson:                   00:32:29               They pulled out. Lost their 20 grand and we quickly dropped the price, ’cause we just thought, “Well, that buyer’s out? What can we do next?” So we dropped the price by a lot, dropped it one more time, then we realized the market was crickets. It was just the commercial and multiunit complex market was just, everyone skittish.

Dana Robinson:                   00:32:51               No one knew … You don’t know what a deal is anymore when there’s nothing moving. So yeah, there was a loss in five million dollars in paper profit, and then the market actually bottomed out in about 2012 or 13 and we reassessed all of our holdings and I was holding like two million dollars in property with three and a half million dollars in debt. I was in my net worth gone from a positive say six and a half, seven million to a negative mil and a half.

Dana Robinson:                   00:33:24               You feel like you’re poorer than someone who’s poor ’cause you actually have zero minus what you oh.

Laura Maly:                            00:33:32               Yikes. Can I shift a little bit?

Nate Broughton:                 00:33:35               Yep.

Laura Maly:                            00:33:35               Yeah. I was just gonna ask, and you maybe alluded to what I might anticipate your answer being, but I don’t wanna assume that I guess. What do you think is one of the biggest misconceptions about you? Either from a listener perspective, or from your peer group.

Dana Robinson:                   00:33:49               I don’t know what people perceive about me. I think before I started writing the book, even when we were living in Comida de la Costa, the perception was just that, I had a lot of money and was really lucky, which was the impotence for the first draft of what became Opt Out, ’cause I thought, “Well, I’m not. I’ve done all these cool hacks to get here.” So even though I had some money and some assets, it wasn’t like, I’m lucky or you’re a lawyer so therefore you’re rich.

Laura Maly:                            00:34:17               Right.

Dana Robinson:                   00:34:18               Lawyers can make a lot of money, but that’s a perception. That’s not reality. I’ve chosen to make a lot less than I would at my career level as a lawyer that I can be free to be investing in business and real estate and writing and doing the life that I want. I’m paying for that.

Dana Robinson:                   00:34:37               If I was a full time lawyer, I’d be paying for that in a different way. I’d be working 60 hours a week and probably making 600 thousand dollars a year.

Laura Maly:                            00:34:46               And I’m not sure where that shift in your personal life from doing the law thing to living the Opt Out Life happened in relation to a family. How has that impacted the way that you live your life with your family?

Dana Robinson:                   00:34:59               I guess, I didn’t completely answer your question of when the Opt Out even happened. At the point where I knew I was gonna take and run that business, I delivered notice to the firm and had the boss try and talk me out of it. And in an empty, climatic, random day on my last day, I took a file box with my stuff in it and walked out the back door, out of the firm, and down the elevator and into my beat up Volvo and drove home.

Laura Maly:                            00:35:29               What were you feeling like at that point?

Dana Robinson:                   00:35:30               I felt amazing. A tingle. A tingle on the back of my neck. And then from there it was maybe three or four months where I had managed to have a couple of clients pay me and I was working on the shoe business, helping my wife with her property management business, and I was walking the block that we lived at the beach in a funky little apartment.

Dana Robinson:                   00:35:54               The office was at the beach as well. I was walking across this sort of one block down the alley and it sort of hit me. Oh, I’ve done it. If all I do is this, it’s enough. I’ve got the life that I wanted now. I’m like, funky office that’s mine, I go when I want and I leave when I want. Dumpy apartment that’s affordable based on what we’re making. No car payments. Free to do whatever I want with the rest of my life. That was the moment where I realized, this is the way to Opt Out.

Laura Maly:                            00:36:28               Interesting. And then the next thought, at least in my own head, so you can see where I’m at, is like, “Now I need to push. Let me push forward. Let me do more. More, more, more.” And that can be business, that could be personal life, that could be my own personal endeavors. Whatever it might be, do you get that feeling at all? Did that come later with the wave of, “Oh, shit,” or was there never that wave? Was there any panic? I’m just curious.

Dana Robinson:                   00:36:54               No. At the time, what I wanted was a balance where I did just enough help with my wife’s business to be sure that I was fulfilling kind of my skills, I was the broker for a property management business and that wasn’t really hard. And then just enough law to cover my share of the nut.

Dana Robinson:                   00:37:10               At that point, my only real venture was a shoe business and I was driving up to Orange County twice a week and going to trade shows four times a year. So for two years, that was it, and I was. It was like having a good time. I didn’t need to make a paycheck from the show business. In fact, I was paying in. I was paying the rent on our warehouse out of my law practice to just be sure that we could function as a shoe business.

Dana Robinson:                   00:37:32               The shoe business for a couple of years was that thing that I poured a lot into and I didn’t need anything else. I think that was kind of like a pretty good balance ’cause I had this base business that paid the bills, this venture that I’m investing my time in, and then, little bit of my expertise going to my wife’s business to kind of keep it flourishing.

Nate Broughton:                 00:37:51               Let’s talk about your curiosity, because, you just mentioned the shoe business. You own part of the wine business, the Modern Cooperage Barrels. We flew up and met with John. There’s probably a few other ones in there that I would qualify as sexy.

Nate Broughton:                 00:38:10               I know opportunities come your way all the time. Seems to me a bit that you would choose the shoe company because of not only your curiosity, but some of the potential ancillary benefits of it, not just saying like, having dinner with Tommy Hilfiger is the ancillary benefit, but-

Dana Robinson:                   00:38:10               It was.

Nate Broughton:                 00:38:27               There’s something … Going to fashion week and getting the front row seat sort of thing. Those are ancillary benefits, but maybe even more what I mean is there’s a story there. This isn’t just another run of the mill business. And I think you’ve chosen some, potentially just because they interest you in a way, whether it’s a personal interest or it’s like, “I want to go along for this ride.”

Dana Robinson:                   00:38:52               Yeah. Yeah. It’s just a mix of things. For the shoes it was, I really … I thought George was meritorious. I liked his story and then as we became friends, you love this person and you want the business to succeed for them. I felt like, I’ll make my own success and yes, it’d be great if I benefit from this thing that I’m helping with this business, but I really wanted that to flourish for him at some point.

Dana Robinson:                   00:39:20               And I still do. I’m still involved at this point because of that. But, yes, the ancillary benefits, you’re in a business that’s kind of sexy. Shoes. I like shoes. I like fashion. I care about how I look. I’m kind of like, not arrogant, but-

Nate Broughton:                 00:39:35               Vain?

Dana Robinson:                   00:39:36               Vain. Thank you. Yes. I’m vain enough to care about my wardrobe, get really excited about 1000 dollar shoes. I love the partner, I love the business, along the way you get cool swag that you trade too, so then you’re around other fashion and you end up with more than just cool shoes. You end up with a cool watch and some cool clothes and you end up bowling with Emma Stone and you end up at dinner sitting next to Tommy Hilfiger and chatting about shoes for two hours.

Dana Robinson:                   00:40:04               Ancillary benefits, for sure. I made a few early mistakes in terms of how I invested my time in projects that sucked. So I got a little more choosy about that, and that’s either the people sucked or the business itself sucked. By the time I got together with George, I was getting better. I still had a few ventures after that that were unsuccessful because it was either a bad business idea or the people involved weren’t the people you should be partnering with.

Dana Robinson:                   00:40:33               Yeah, you get a little bit more protective and greedy with your time and resources once you’ve made some mistakes. It’s same as investing. If you’re an angel investor, you’re gonna be throwing 50 grand here and 50 grand there and you’ll learn your lesson pretty fast because of the discipline that comes from money.

Dana Robinson:                   00:40:51               And in some sense, it’s even harder to lose on a venture because it’s your time because I think it costs more than money, in a way. I mean, it’s a commodity that you have more of when you’re poor, or when you’re struggling, or when you’re trying to grow your asset base.

Dana Robinson:                   00:41:06               But in some ways, if you’ve got a bunch of money and you lose 50 thousand dollars, it’s smart when you invest 50 grand and your time in something and it turns out to be a waste.

Nate Broughton:                 00:41:15               You can actually feel that one.

Dana Robinson:                   00:41:17               Yes. Yeah, absolutely.

Laura Maly:                            00:41:19               So with that, that might be a good segway to what is something you would’ve told your younger self knowing what you know now?

Dana Robinson:                   00:41:28               I mean, besides sell before the crash?

Nate Broughton:                 00:41:31               Buy more Apple stock. Hold the Apple stock.

Dana Robinson:                   00:41:34               Yeah. Oh yeah. The Apple stock’s a great one. I owned Apple stock, 100 shares in ’96 and I sold in ’99. And I had 100 shares in 2006 and I sold in like 2009. Doubled my money both times. If I’d held on to either, I think it’d be a million dollars now. Just either time.

Dana Robinson:                   00:41:52               I had two opportunities to own and hold Apple stock and didn’t. But, so many things I would tell my younger self.

Nate Broughton:                 00:42:00               Maybe a book.

Dana Robinson:                   00:42:01               Maybe I would write a book.

Nate Broughton:                 00:42:02               Yeah. No, maybe you should write a book to your younger self.

Dana Robinson:                   00:42:05               I probably would tell my younger self to have thrown myself deeper into one of my ventures earlier. I think I’ve held onto my law practice as a safety net for too long and I probably was ready when, right before the crash happened. But, the leap of faith, in a sense I made it to when I left the firm to go solo, but at heart, if I was an entrepreneur, I think my entrepreneurial vein deserved more of my attention than the law piece would give it.

Dana Robinson:                   00:42:48               So, maybe it would’ve been to have had the confidence, and I heard a podcast actually, about the founder of Slack, and when they made a pivot, he said their policy was to burn the village.

Laura Maly:                            00:43:01               One of the questions that I had asked Dana was that if he could tell his younger self something, what would it be? And he said that he wished he had jumped more head first into his entrepreneurial adventures. And it was funny reflecting on that because, the perception of Dana is that owning a lawn care business at 21-22, you can’t dive any deeper than that.

Laura Maly:                            00:43:23               So I thought that was fairly humorous. It’s like, “How could he have dove deeper into his entrepreneurial ventures considering where he came from?”

Nate Broughton:                 00:43:29               Right. And I mean, we know that before he went to Bali he said he was juggling six different businesses. He’s still juggling several side gigs. Real estate, his law practice, the Opt Out Life. He is so deep in entrepreneurship that you’d be hard pressed to find someone who is comparable. And it also goes back to how much experience he’s had. He’s such a valuable mind and a valuable mentor because he’s had so many experiences in so many different industries.

Nate Broughton:                 00:43:55               So yes, it is straight comical for him to say he wishes he would’ve went deeper, but it’s also interesting to me that he would ever have anything nagging him in the back of his mind, because, he doesn’t come across as someone that has ever made a decision in life, at least as long as I’ve known him, which has been a pretty long time, and I know most of his story.

Nate Broughton:                 00:44:15               That was like, anything other than, “This is what I want to do. I’m gonna go full bore into this. There’s no reason to hold back, and I’m gonna do it.” That sounds like what he’s always done. He’s always said yes to opportunity. He’s always pursued things that interest him.

Nate Broughton:                 00:44:31               I just … It’s just funny. I can’t imagine him sitting around in the back yard being like, “Fuck. What is wrong with me? Should’ve gone harder.”

Laura Maly:                            00:44:39               He does do that, ’cause we know he thinks about thinking.

Nate Broughton:                 00:44:41               That’s true, he does think about thinking as we established, I think a little bit later here in the story. But you’re right. I guess I get it where it’s like, he’s an attorney. That’s his honey pot in a way. He knows he can always go back to that and if he knows he can always go back to that, maybe he’s a little too attached to the tit every month where he’s maybe got a dollar figure in his mind where he’s like, “As long as I can make my nut from law, then everything else, I can be the guy I wanna be and do all the things that I wanna do and put on this persona, say yes to opportunities.”

Nate Broughton:                 00:45:11               But he’s still maybe clinging a little bit to that amount that comes from the law firm. I get it a little bit.

Laura Maly:                            00:45:17               Yeah, that makes sense.

Nate Broughton:                 00:45:17               Okay. All right, well, let’s jump into some thing fun. We’re gonna hear about Dana’s tattoos and also a little bit more about his fores into religion.

Nate Broughton:                 00:45:25               Let’s talk about tattoos for a second. How many tattoos do you have?

Dana Robinson:                   00:45:29               I don’t know. I haven’t counted them. Let’s see. One, two, three-

Nate Broughton:                 00:45:29               You can count them.

Laura Maly:                            00:45:29               You don’t know how many tattoos you have?

Nate Broughton:                 00:45:29               I know.

Dana Robinson:                   00:45:33               Four, five, six, this on one, seven.

Nate Broughton:                 00:45:36               Seven?

Dana Robinson:                   00:45:36               I think seven.

Nate Broughton:                 00:45:37               Nice.

Laura Maly:                            00:45:38               How many tattoos do you have?

Nate Broughton:                 00:45:39               One. I got more time to catch up. I gotta catch up.

Laura Maly:                            00:45:44               You got more canvas.

Nate Broughton:                 00:45:45               I’m trying to catch up. Yeah.

Dana Robinson:                   00:45:46               I started six years ago. You’ve got … If you wanna start when I started, then you’ve got five more years, six more years, something like that.

Nate Broughton:                 00:45:53               Right. Have some time. Seven years. Yeah.

Dana Robinson:                   00:45:55               We can talk about the religion. You want to bring it up?

Nate Broughton:                 00:45:57               You went to theology school, am I calling it the right thing? Theology school.

Dana Robinson:                   00:46:02               Yeah. I went to Bible College, which is a four year degree program where the only thing you can study is some sort of biblical study.

Nate Broughton:                 00:46:10               So that was your college.

Dana Robinson:                   00:46:11               That was college.

Nate Broughton:                 00:46:12               You didn’t join the frat and go to the dorm and …

Dana Robinson:                   00:46:15               There were no frats.

Nate Broughton:                 00:46:16               … do keg stands and other things that you do in college.

Dana Robinson:                   00:46:20               No drinking, chewing tobacco, smoking, dancing.

Nate Broughton:                 00:46:24               Have you been chewing tobacco with those college kids? Okay. So you went to Bible College. That’s lame.

Dana Robinson:                   00:46:31               And then seminary is the graduate school that you do for theological studies.

Nate Broughton:                 00:46:36               Right. So, you don’t seem to fit that, I’d say, my friend. Both in appearance in personality. Maybe a little bit in personality the whole mentor, help people thing. The sage advisor with the soft hands leading you down the path of life. That fits. But it doesn’t seem to fit much else about you.

Dana Robinson:                   00:46:57               Yeah, I don’t have a collar.

Nate Broughton:                 00:47:04               Yeah, well, for one.

Dana Robinson:                   00:47:04               I went to Bible College, because that’s just what I felt called to do when I was a kid. The only person I knew with a college degree was my youth pastor, and I was like, “How did you end up here?” And he’s like, “I went to Bible College.” And so, I went to a year of junior college to get all the secular units I could for cheap and then went to Bible College, which turns out to be wildly cheap as well.

Dana Robinson:                   00:47:26               It didn’t feel cheap at the time, but I mean, I have no student loans from it and I think I was paying 1500 bucks a semester for school in … technically it’s a private institution. And then finished that and went to study … I was running a second business, the coffee house and thought, “Well, I should do more of this ’cause I still feel like I don’t know much.” I was technically a pastor.

Dana Robinson:                   00:47:48               I enrolled in seminary, which is the graduate school of theological studies. But, all of that put me around different thought. People who were, I guess I could trust in my mind because they were also Christian or religious.

Dana Robinson:                   00:48:03               And then from there I spent four years as a pastor at a big church and processing all of what I learned. And I think a lot of Christians don’t do that. They sort of embrace the dogma, and they want the simplest thing to hold onto and to sort of form their beliefs around. And, I know, I was starting to think, “Well, there’s a lot of different approaches to religion.”

Dana Robinson:                   00:48:27               What I didn’t like was that my job involved kind of involved running the country club. I thought in the course of each year, I probably helped like one group, one family, one couple, one person. And, I started to think, “Man, if I had a real job, I could probably still help one person a year with their lives just like, that would be easy.”

Dana Robinson:                   00:48:48               And, “All I’m doing here is kind of running programs.” I was a dean of a bible college on this campus. A pastor on staff at this big church that was all part of the same compound and vice principal at the elementary school. I was just running around running programs all day long.

Nate Broughton:                 00:49:02               Did you have to stand up and give sermons?

Dana Robinson:                   00:49:05               I did. Yeah. I did. I gave sermons, I did four weddings, three funerals, so some formal ceremonial things, went to visited some people in the hospital. So yeah. Some of that.

Nate Broughton:                 00:49:18               All at a young age. This is in your 20s.

Dana Robinson:                   00:49:20               All before I was 24.

Nate Broughton:                 00:49:22               Yeah.

Dana Robinson:                   00:49:22               Wait, 26 is when I left. So from 22 to 26.

Laura Maly:                            00:49:27               That’s like a whole life lived in four years.

Nate Broughton:                 00:49:28               I know, yeah. That’s not what a lot of people are doing at that age either. People that are in that profession, yes, but it’s interesting to think about what most people, at least I know, most people who I age, what they were doing, you’re not partying up in PB and you’re 23.

Dana Robinson:                   00:49:47               Now you know why when we first met I was hosting those epic parties at the mansion, right?

Nate Broughton:                 00:49:52               Yeah. I was gonna say, all this …

Dana Robinson:                   00:49:52               The Halloween parties?

Nate Broughton:                 00:49:55               Mm-hmm (affirmative). Mm-hmm (affirmative). Pent up.

Dana Robinson:                   00:49:56               Pent up party.

Nate Broughton:                 00:49:58               Pentagostals. I’ve got the title for this.

Dana Robinson:                   00:50:01               I’ll tell you this … you got this. Partying at 40 is probably way more fun than partying at 20, I’ll tell you that.

Nate Broughton:                 00:50:06               I mean yeah, it’s certainly a lot more intriguing. You stand out a bit.

Laura Maly:                            00:50:10               A less keystone light in [crosstalk 00:50:15].

Nate Broughton:                 00:50:14               Yeah. He’s a fun guy to be around. He’s still doing it. I think it’s made you the role model for a whole generation of 20 something’s out there.

Dana Robinson:                   00:50:14               Yeah.

Nate Broughton:                 00:50:22               This time you spent in your early 20s doing something quite different. When you had your chastity belt on, we’ll say. The chastity belt years of Dana Robinson have led to a fruitful 40s for many of us, not just him.

Laura Maly:                            00:50:37               So, we’ve heard about Dana’s history and going to bible college and seminary and we’ve heard about his tattoos, but I think I’m gonna turn this section over to you, Nate, so that you can share a couple anecdotes I know are on your mind.

Nate Broughton:                 00:50:48               Yes. I feel it’s an appropriate time in the podcast and since we’re doing this podcast where I get to talk about Dana as he’s the guest, to mention what all his background and his color on his story as a young man means to me and makes me think of, because when I met Dana he was 39 years old. His daughter was in high school and in some of those early years and he was living in a very sexy home on a very cool street in La Jolla and I walked into his door and we had wine and snacks as we’ve talked about and later cigars and scotch and he was as the intro says, the most interesting man in the world to me.

Nate Broughton:                 00:51:24               Someone who was at that age that was very far from run down. Stylish. Energetic. Liked cool music. Went to shows. Liked to party. Loved entrepreneurship. Loved meeting people. He was just full of life at an age where not everyone’s like that. And he’d been raising a daughter who was now in high school. He lived a different side of life and it was cool to know him at that time and now I understand about why he had parties at his house.

Nate Broughton:                 00:51:50               Things happened that we probably shouldn’t talk about, things that reminded me of things that happened when I was 20 and 21 that apparently he missed out on when he was at bible college or was a young father. I can understand having a lot of pent up frustration from the non partying with the Pentecostals, we’ll say. I joked with him about removing his chastity belt in his late 30s and him and Heather really were kind of the hip, cool couple, that not only I looked up to, me and my wife, but everybody in our social circle.

Nate Broughton:                 00:52:20               In a lot of the younger people around me, too. I mean, Dana is really good friends with a lot of good people that I brought out to San Diego that were 20 years old when he met them and he can identify with those people. He’s fun to be around. And there’s a lot more to the man than even all this coll entrepreneurial background, sage advisor stuff.

Nate Broughton:                 00:52:36               He’s a fun guy to be around and hopefully that comes through and now we get a little bit more understanding as to why.

Dana Robinson:                   00:52:42               All right, so got a lot of stuff that I could probably talk about religion, but what a lot of people wanna know is, when, how, why did I leave? Even when I was at law school they’re like, “Pastors can’t become lawyers. Lawyers are evil and pastors are somehow good people,” or something like that. I know what the perception was, but it was always surprising for people to think pastor and correlate that somehow with lawyer.

Dana Robinson:                   00:53:05               But at the point I was going through a good, natural existential crisis, which you should go through if you’re philosophizing, if you’re a religion student, you should be thinking about this stuff, not just memorizing it. So, after several years of studying and thinking about it, I actually had a phone call from a girl who was graduating from the high school group. I wasn’t youth pastor, but she knew I was … I at least had a graduate degree.

Dana Robinson:                   00:53:29               A lot of pastors don’t have any degrees. And so she called me. She’s like, “So, I’m thinking about going to bible college.” She was graduating valedictorian, wanted to be a doctor, had all the options in the world open to her and gone up to camp or something and gotten all fired up on Jesus and decided she was gonna go to bible college, so she’s calling me maybe expecting for some good advice.

Dana Robinson:                   00:53:50               And I found myself, I was gentle, I think, but I said, “You could be a youth pastor with no degree. You’re smart and you’ve got the world open to you. You should take that and go get a great college degree and go to medical school. And you’re gonna go out there in the world and engage culture and do good stuff and be a positive impact on the world. That’s what you should do.”

Dana Robinson:                   00:54:14               And then, she’s like, I think taken back. We had a little conversation, hung up, and then I was sitting in my back yard looking up at the stars and I kind of had this, “oh shit” moment where I realized I was talking to myself and started to process that. I told my wife that I was having these thoughts, it’s career suicide thoughts.

Dana Robinson:                   00:54:35               And she was so thankful. She was like, she had been done with church for many months, maybe longer, and certainly not over the existential. For me, I processed it slowly and thoughtfully. Heather processed it one Sunday when she looked in her wardrobe and said, “I have nothing to wear to church. Why do I even have to wear something churchish to church? I don’t think I like church.”

Dana Robinson:                   00:54:57               She just went through it very, very quick. Very, very quick processing where she disposed of the need for church entirely, almost revolutionized her whole religious view instantaneously, and has been a free thinker and agnostic, I guess, ever since.

Dana Robinson:                   00:55:14               For me, I was really slow and deliberate, needed to have a lot of conversations around the fireplace. But that was the beginning and I found myself needing a real job and a real career knowing I was gonna leave ministry and probably not go back to church.

Dana Robinson:                   00:55:26               I went to law school.

Nate Broughton:                 00:55:27               Let’s not talk about that. No wants to hear about law school though. I like Heather’s story. That’s pretty funny. Sounds like her.

Dana Robinson:                   00:55:37               Yeah. It’s funny because I don’t think I realized until the last few years that we both process things this way all the time. I process things in sort of this existential way. I think about the how and the why and I’m not really thinking down on boots on the ground mechanics and it takes me a while to get down there.

Dana Robinson:                   00:55:57               Have to sort that out in the head first. Then I’m okay getting down to the mechanics and Heather just goes straight for that and doesn’t really need to process the existential reasons for things. It’s kind of cool to realize that with your friends, your partners. I think that people that I have been friends with are similar and I don’t know.

Dana Robinson:                   00:56:19               It’s revolutionary for me to think about how I think and realize it’s not the way that everybody thinks.

Nate Broughton:                 00:56:26               Yeah. Not a lot of people think about thinking. I don’t know if that’s a trade of the Opt Out Life, maybe it’s a small trait of someone who has it, but it certainly makes for more interesting people and ideas and thoughts, if you can take a moment, sit in the back yard, look up at the stars and think about what you think about.

Nate Broughton:                 00:56:42               That’s a rare trait. But I was gonna say about Heather and actually we’ve had Laura Story as well with her husband, they are business partners. Good partners in crime. I’m using that again, but they have a good partnership.

Nate Broughton:                 00:56:54               You have a good partnership with your wife as well. You wouldn’t get to do all the cool shit that you do or be who you are if she wasn’t who she was. Or I guess you guys would have to go your separate ways or something if you couldn’t be you. It’s worked out really well, I think a lot of people in our social group look at your relationship with some envy and think, “There’s two people who are doing it right,” we’ll say.

Nate Broughton:                 00:57:15               How has she allowed you to get to this point and be Dana Robinson?

Dana Robinson:                   00:57:22               I think she came into the marriage in love with that part of me. That sort of independent character that would just do stuff like say, “Hey, I’m going to college. You wanna come with me? I’m moving to LA, no resources. I’m gonna start a business, can I borrow your Volkswagen Golf to run my lawn mower around?”

Dana Robinson:                   00:57:43               So she came into it I think with some expectation of that and in many ways embraced it as my partner throughout. In fact, the landscape business, she was at a job she hated when we got a couple of big accounts and she was really didn’t want to go to work. She wasn’t at that point going to college any longer and she wanted to mow lawns with me.

Dana Robinson:                   00:58:03               She did. For about six months before we could hire … we had one employee and I didn’t have enough money to hire another. She’s like, “Well, if I quit my job, will we make enough from me helping you?”

Dana Robinson:                   00:58:14               I’m like, “Probably.” I mean, I didn’t do the math, another novice move. But I’m like, “Sure.” So we drove around in our Ford Courier that had been hand painted with a roller, speed up, $700 truck and at one point it would have like me, this employee, Todd, who I always bounced paychecks and Heather sitting in the middle and we drove around and mowed lawns together.

Dana Robinson:                   00:58:40               She was good with the early version of the Opt Out Life, kind of living my way. I think we went south a little on following Dana’s path with the coffee house. She was shaking her head the whole time. It was my wild idea and I knew it was gonna be amazing. We made some mistakes, we were uncapitalized, it was a lot of work, and then she got pregnant. We sold that, wrapped it up, and got out of it with the skin of our teeth.

Dana Robinson:                   00:59:06               At that point, I think she thought, “Well, Dana’s not that magical. Not everything he does seeds.” She was still down for the adventure of kind of what I was charging at and I think our best partnership in terms of business that we really did do together was her property management business. I needed to be the broker, I’m licensed, and she knows how to do that vacation rental business.

Dana Robinson:                   00:59:28               She got to apply her skill, doing what she’s good at, with the support of me doing what I was good at at high level, and my law office was in her office. Two and a half days a week, I was around to be sure things got done and we got to go have a beer in the middle of the day on Wednesdays and talk about each of our businesses. I was involved with hers enough helping her, that she felt like my support, she was helping me with mine.

Dana Robinson:                   00:59:54               I think everybody’s relationship is different. I don’t think any of us necessarily needs to be the boss. We just need to know who’s the boss at the time. We like to cook together. Sometimes we like to cook. We should start there. Sometimes we’re completely lazy. We’re on a Thistle kick right now where we get this pre made vegan food that’s amazing and you don’t have to cook.

Dana Robinson:                   01:00:12               But when we cook, there’s only really one question is, who’s the chef and who’s the sous chef. I don’t really care if I’m the sous chef, I just need to know.

Nate Broughton:                 01:00:20               Right.

Dana Robinson:                   01:00:21               And I will do that. And if I’m the chef, don’t get in my way. Don’t usurp my chefness.

Nate Broughton:                 01:00:29               All right Laura, last voiceover here on Dana’s podcast. You are getting some stories from him about working and being with Heather his wife. I know they’ve owned businesses together, not only the business of doing business, but the business of their lives. You can tell that they’re partners in crime. He’s told us a story about they get along really well even when they’re cooking, as long as it’s established who’s the chef and who’s the sous chef.

Nate Broughton:                 01:00:53               And, like I’ve said, I’ve always admired their relationship. I look to it for inspiration for my own and it’s cool to hear about how he thinks about that and how they’ve made it all work because not everyone, and dare I say, very few people could work with their spouse. And that’s an interesting thing to bring up, because you, in fact, are business partners with your spouse and it seems to go very well as we’ve heard in your podcast.

Laura Maly:                            01:01:15               Yeah. I mean, not every day’s a walk in the park.

Nate Broughton:                 01:01:17               Right.

Laura Maly:                            01:01:17               But, for the most part, I think we get along really great. We have a very organic ability to figure out where our place is in any given project or task at hand. And so, I think that’s a really natural fit. The thing I really identified with and what Dana was saying about him and Heather is that they seem to have a very mutual respect, but also a very mutual expectation setting that happens both in their business life and their personal life and so, I think I really took something out of that was, it’s all about setting expectations.

Laura Maly:                            01:01:49               And I think when I really boil it down for Michael and I too, I think we see our most successful moments when we’ve set good expectations about A, what my responsibilities are, what his responsibilities are, and then what we want the outcome to be for whatever we do. And I really heard that translate in what he was talking about with Heather and him as well.

Nate Broughton:                 01:02:05               Where do you think people mess up with that? Because, I agree. I think a lot of people just slip into a point where they aren’t vocalizing their expectations. Is it laziness? Is it tiredness? Is it lack of awareness, mindset? Where do people mess up with that? Because, there’s no question that if all of us talked about that on a daily basis with our partners, I think we’d be better off.

Nate Broughton:                 01:02:29               Why do you think people fuck it up?

Laura Maly:                            01:02:31               So, that’s a great question. I don’t think it’s laziness necessarily. I think it’s just nature to assume that your partner knows what you want. And so, when you go about saying it directly, it kind of just gives people opportunity to react and settle in the information.

Laura Maly:                            01:02:47               The other thing is I think, you kind of have to give your partner, or your business partner, or your spouse the space to be a human being and have the space for them to not always react the way that you want them to and figure out how to find a center in that.

Nate Broughton:                 01:03:00               Do you mean, being forgiving when they’re not up to speed on the expectation, or is it giving them the physical space to, like Dana tells us, he lets Heather go off and play tennis and that’s her thing.

Nate Broughton:                 01:03:10               I know that contributes to a good relationship, but is that what you’re talking about, or is it something else?

Laura Maly:                            01:03:14               I think it’s a bunch of stuff. I think it’s physical space, I think it’s space to be forgiving, but I also think it’s space to find compromise and perhaps it’s not in a more traditional sense of compromising. Perhaps it’s taking time away from a decision to come back to it later, or think of new ideas to approach it.

Laura Maly:                            01:03:28               Yeah, I think a couple of ways.

Nate Broughton:                 01:03:29               And all in all, if you don’t get these things right, it’s a lot harder to live the Opt Out Life, whether that’s business or personal, right?

Laura Maly:                            01:03:29               Yes.

Nate Broughton:                 01:03:36               Yes. All right. Well, we’re getting in on some fun stuff, because I know you and Dana have both spent a decent amount of time in Bali, so we’ll get a few stories there, and let me just say thank you for co hosting on this episode. We’re glad to have you around.

Laura Maly:                            01:03:50               My pleasure.

Nate Broughton:                 01:03:52               All right cool.

Dana Robinson:                   01:03:52               So, I think we’re good at that collaboration because we got married young and she’s been involved with all of the ups and downs of all the businesses. She’s always been in the loop with everything. And that’s a blessing and a curse, I think.

Dana Robinson:                   01:04:05               It’s been good and bad for both of us. For me it’s good because she knows the drama. The last four months we’ve been trying to close on a four-plex and she knows why I’m awake in the middle of the night. But, she’s stressing. So, from her side, she gets the benefit of being in it, but the stress of having to sort of ride along with it.

Dana Robinson:                   01:04:25               Then from my side, the same thing. I know it’s a burden for her sometimes to have to be involved in my stress and she shouldn’t have to be. But she is and I like it because it supports me in those times when it’s the hardest.

Dana Robinson:                   01:04:38               And I think when things are going great and she gets to celebrate and feel deeper ownership of the things that maybe I’ve done with her knowledge and support, but not necessarily a lot of her time. She still gets to feel like a winning member of the team ’cause she is.

Nate Broughton:                 01:04:53               Yeah, she is. You want in on something fun, you got any ideas?

Laura Maly:                            01:04:58               What did you like most about your time in Bali?

Dana Robinson:                   01:05:02               I liked a lot about Bali. Okay. I’ll give you the most practical. I liked that … I described it as a vacation from money.

Laura Maly:                            01:05:11               Yeah.

Dana Robinson:                   01:05:12               So having been an entrepreneur all of my life from the time I was 19 with that landscape business, scrapping around, being sure I don’t bounce checks on payroll, all the way up until the moment I left for Bali, fight, fight, fight. Just fight for money, fight to pay the bills, fight to keep the balls in the air, this sort of juggling act.

Dana Robinson:                   01:05:32               And my housekeeper cost 100 bucks a month and I was overpaying her. In fact, I think I paid her 120. It didn’t matter. It was sort of like, whatever. She showed up at 11 and cooked my lunch, and cleaned my house, and did the laundry, and then cleaned up after lunch, and then prepped something for dinner and brought cookies to the pool for 100 dollars a month.

Dana Robinson:                   01:05:51               So my villa was like 1100 a month and it was lavish. I went overboard on that. I could’ve been paying half. It was just this great vacation and that gave me some mind share I didn’t realize was important that comes from the money juggle. The money juggle isn’t really about the amount, it’s just that that’s part of the entrepreneurial game.

Dana Robinson:                   01:06:15               I mean, my problems are not much different than someone who’s where I was 20 years ago, I just got more zeros on it. When I think of other entrepreneurs that I know, I have clients that are 10 times the net worth I have, and they have the same problems. We were just up talking to, I think you talked about it, so I can mention it here, that my wine barrel partner, he’s got three major projects in place. He’s got money going out and at this point, none coming in.

Dana Robinson:                   01:06:43               So he’s doing the money juggle with a lot more zeros on each of his businesses. He’s got wine, the land development, and a wine barrel business. That game is fine for a certain amount of time, but it was wonderful to have a break from it, where I knew for that year I wasn’t gonna have to really think that much about how much anything was and what it cost and that was cool.

Dana Robinson:                   01:07:07               The other thing I really loved was the sort of physical distance from the balls that I juggle. That also came with a time differential. That gave me this time warp, I felt like I’d taken a time machine and I lived in the future and I would only visit your timezone for one hour every day. Then that gave me that freedom I also hadn’t had for … since the innovation of email at least.

Dana Robinson:                   01:07:31               I hadn’t had that kind of freedom to just be at the beach with no phone, have a boat drop you off in the middle of the ocean while you surf for a couple of hours and not be thinking about what time it is, what you’re gonna have to do when you get back.

Nate Broughton:                 01:07:47               If you hadn’t gone to Bali, what would’ve happened? Because, we wouldn’t be doing this, for one.

Dana Robinson:                   01:07:56               Nope. No we wouldn’t of.

Nate Broughton:                 01:07:58               And this is just one small component, it sounds like. Maybe what would’ve happened. You ever think about that?

Dana Robinson:                   01:08:02               Yeah. Yeah. I mean, I was at a point where I could’ve merged my practice with a larger firm had I gone deeper and bigger on law. And that would’ve been an Opt In.

Dana Robinson:                   01:08:13               It’s easy for me to look back and say, “Well, I’ve always had sort of an Opt Out strategy to things, but you reach a point where when I went to Bali where you’re kind of approaching various angles of burn out, that it’s easy to retreat to that one thing, maybe that safety net. Probably would’ve down scaled in some way anyway.

Dana Robinson:                   01:08:31               I think I had built a bigger life than I needed and my daughter was now out of the house, and so, I hadn’t really reevaluated that, that sort of space cost needs of the Robinson household. But yeah, I knew I needed to write and I had all these unfinished things and the first thing I finished was actually the religion book, because I had started it earlier and it was more closer to finished.

Dana Robinson:                   01:08:55               But it gave me a chance to reflect on writing, get low, improve it a little bit. Then I dug in on this one and fell into a groove.

Nate Broughton:                 01:09:05               So really, there was no choice, basically.

Dana Robinson:                   01:09:05               Yeah.

Nate Broughton:                 01:09:08               You basically said this had to happen.

Dana Robinson:                   01:09:10               Yeah. There’s no way I would’ve had the mind share in any choice I would’ve made here to finish the book with the clarity that I did.

Nate Broughton:                 01:09:19               Right.

Dana Robinson:                   01:09:19               I’ve got three others fleshed out and it’s some version between 70 and 90 percent done. That’s a lot of writing and a lot of mental clarity that I couldn’t have gotten in 14 months anywhere, and I had years and years of tinkering on these chapters in each of these books that you need that kind of absolute clarity and time where time doesn’t matter.

Dana Robinson:                   01:09:44               Time and money didn’t matter. I guess that’s a good way to put my experience in Bali.

Nate Broughton:                 01:09:49               Well, I’m glad you did it. I’m glad you are finishing some of those other books. I’m glad the Opt Out book is done, it’s real, we can hold it, we can touch it.

Dana Robinson:                   01:09:49               Yes.

Nate Broughton:                 01:09:57               It must be a good feeling. I’m happy for you …

Dana Robinson:                   01:09:57               Thank you.

Nate Broughton:                 01:09:59               … to have it. And thanks for doing this. Hopefully everybody enjoyed hearing a little bit more about Dana. Laura thanks for co hosting.

Dana Robinson:                   01:10:06               Thanks Laura.

Laura Maly:                            01:10:07               My pleasure.

Nate Broughton:                 01:10:09               All right guys, I’ll see you later.

Nate Broughton:                 01:10:12               Thanks again for listening to the Opt Out Life Podcast. If you liked this episode, or any of our episodes, we’d love to have you as a subscriber. Click the subscribe button on iTunes or wherever you get your podcast. Then, head over to optoutlife.com, there you can enter an email address to get on our email list, so you’ll be the first to know about new podcast episodes as they come out, including hand picked highlights, links to resources we mention, and top quotes from each episode.

Nate Broughton:                 01:10:38               Dana and I are also publishing new articles on site, including how to guides and blueprints for you to use to find your next side gig, or find a creative idea to help you live the Opt Out Life.

Nate Broughton:                 01:10:48               Opt Out Life email subscribers also will be the first to get access to upcoming video content, which includes a short documentary we shot recently here in San Diego, as well as opportunities to interact with us and our growing community through the Opt Out Life premium membership.

Nate Broughton:                 01:11:03               All that and more starts by heading to optoutlife.com and entering your email. If that’s not enough, you can follow us on Instagram at Opt Out Life. Give us a shout out or ask a question about your business, your travel plans, or anything we might be able to help you with. We’ll talk to you soon, Opt Out out.


Our Guest

Name Dana Robinson
Website optoutlife.com
Instagram danarobinsonx

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