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Dana Robinson & Nate Broughton: The Opt Out Life

Rethinking What Success Looks Like

You are in for a special episode because you are going to get introduced to the Opt Out lifestyle. There are two special individuals that are leading this movement.

Our first guest is an internet marketing veteran for years. He specializes in lead generation and client acquisition. He's built and sold four companies. He has been involved in several acquisitions with private equity firms. His name is Nate Broughton.

Our second guest is an attorney, entrepreneur, law professor and LinkedIn Learning educator. His entrepreneurial ventures began when he was a kid selling the family chicken eggs to neighbors, mowing lawns and making hair clips he sold to girls in middle school. He's dabbled in real estate and many others. He's an attorney, but we're not going to hold that against him here. His name is Dana Robinson. We're going to talk about the Opt Out lifestyle.

This is based on a book called Opt Out: Rethink Success. Reinvent Rich. Realize the Life You Want.

We’ll also talk about a fun thing I like to share on the show, which is exiting. How can you successfully build a business to sell it? What does that look like if both of these individuals haven’t done that in some form or fashion? We’ll also talk about networking and how to properly do this. How to build your network? When you reinvent, when you go on to the next business, maybe you're in business right now and you need some assistance. How do you build that powerful network? We’ll also get into the number one tell, something that you can ask somebody in an interview to test their character and meddle. If you're going to be a successful entrepreneur or building successful teams, you definitely are going to want to read this blog. We’ll talk a little bit about traveling, all in the conversation of opting out and rethinking what success looks like to you and living the life you want. With that said, let's get to it.

Dustin
Dana, before opting out, you filed bankruptcy in 1993. You had brain surgery in 1997. In 2008, your net worth dropped from $5 million to negative $2 million. I’ve got to tell you, those aren't experiences that I want to have. How did you get through these things? What's the story behind these crazy incidences?
Nate & Dana
Part of it is living life. The realization in looking back is that there's a lot of luck and bad luck. If you're going to have success in business, you have to make big bets. Back in 1990, I started a landscape business that grew at employees. I thought, “This is cool. I can do more.” I opened a coffee house. By the time we liquidated both of those, we didn't have any resources had left. We probably needed to file bankruptcy, but in my early 20s, having owned and sold two businesses, it felt like a clean slate. I don't know if I have regrets other than my wife will tell me, “You shouldn't have started the coffee house.”
The brain surgery is life dishes stuff out. You wake up in the hospital. In fact, your studio is across the street from the hospital. I woke up that night. Back in the ‘90s, I was a law student and had a grand mal seizure. Luckily, I was married, my wife was there to see it. She made sure I didn't choke on my pillow, which is a real thing. It turned out that I had a lesion on my brain. I had to take a spring break off for brain surgery during law school. By the time we got to the real estate boom, I had thought I was being a smart real estate investor and it turns out I was. I didn't have enough liquidity. I barely survived the downturn. I had both my big properties in escrow entitled to a high rise in 2007 and the market flattened.
It was before 2008. We didn't know what was coming. The market suddenly dried up. I think the smart money was suddenly on the sidelines. We were in escrow two properties that we had paid a total of $3.5 million for about $13 million. My partner was about to split the proceeds of that. He had already been through that cycle. He wasn't quite as excited as I was because he already had some money then it went flat. We dropped the price. In 2008, it melted down. We threw our hands up and went, “We're in this for the long haul.” Things are out of your control. If the market had sustained for another year, I'd have cashed out. I probably would have written a book about what a smart person I was. With the book that I did write, someone accused me of humble bragging once. I'm telling you all the shit that happens, good, bad, ugly. If you're going to try to be an entrepreneur and invest in real estate, you're going to take some chances that bad stuff happens. You hope that if you keep playing the game and some chips at the table, that you'll be able to sustain it. Luckily, we have, that's the meltdown inverting our net worth. We survived it.
Dustin
All three of these incidences were not fun. What's your advice for someone? It's easy when you're not in any of these to say, “Those are life occurrences.” However, when you're in it and you are desperate or you're clinging on, what's the advice you give them to get through that?
Nate & Dana
It's good to hear stories from people that are not the gurus of success. To be honest, that's my story. There are many other stories we have on our own show. It's the idea that the only path is not this big trajectory for entrepreneurs. Many people think that raising money and success is based on whether you get money and then build a giant business and exit. You're taking that giant exit. The reality is most people don't get there that way. You're going to have some failures along the way. You have to be prepared for that. When those happen, listen to the voices of people that have had the failures. Get your mojo back. Get back in the game. If that means getting a clean slate and starting again, then do it, fail. I know a guy who was bankrupt in 2003. He is dealing with $100 million-plus loans now and making tens of millions of dollars a year. Your failure in the past is not an indication of your future. If you're in the middle of a failure, you could have an amazing trajectory still ahead. You have to get back in the game and play.
Dustin
One of those pivots for you is in 2015. You moved to Bali on a one-way ticket. How did you come to choose Bali? What's the story behind this epic journey that you went on?
Nate & Dana
Choosing Bali was serendipity. My wife and I were barflies after our daughter was out of school. Once a week, we'd go hit those local bars in La Jolla. The bartender one day said, “Why don't you come to see me this weekend? It'll be the last time I'm here.” We said, “What are you doing?” He goes, “I'm going to Bali.” We're like, “When are you coming back?” He goes, “I'm not. I'm moving to Bali.” We go, “What? How do you do that?” It piqued our interest. He told us that he was going to go live on savings. It's cheap to live there. If he ran out of money, he'd go work in Australia. Months later, I had a day where I felt that I’ve been juggling between the businesses, the real estate, all of the things that I had been in.
I'd never tried to figure a way out. I was holding on to too many things, holding on maybe for dear life and having survived the crash continuing to juggle. It was exhausting. I said to my wife on a whim, “Maybe we should sell everything and move to Bali.” She said, “I was thinking about it.” We hadn't talked at all. There was no conversation. This was somehow floating around in our heads and in minds. We had a serious talk about it. We thought it was maybe a way to force us, but mostly me to discipline the investments I had, get things under control, take that E-Myth approach to get out of the business and to let other people do things.
I talked to the few people that worked for my law practice and said, “I can liquidate and get you guys jobs.” They said, “No. Let us run it. We can get by on an hour a day of your time.” It enabled me to say, “I think between my side gig income and a little bit of the income, I'd pull from continuing to let myself have this law practice that I didn't have to run, I would make few thousand dollars a month.” I figured that I could survive. We bought one-way tickets. We did have an estate sale. We sold everything as someone died. We sold our cars and put them in the heirlooms in a 10x10 storage and prepaid for a year. We got on a plane. We picked Bali because we knew it was cheap and full of ex-pats. That was it. We didn't know quite what to expect. We didn't know when we got there it would be a little more of a wild, dirty ride like an India style streets with crowds and traffic.
Dustin
It wasn't like in magazines or on TV.
Nate & Dana
It is not like the Instagram pictures of the model's posts or the surfer's posts. Definitely, there are those scenes, but you have to go find them. Amidst all of that, it's six million people crowded onto a small amount of space, going very fast on scooters and beat-up cars. It was not what we expected, but it turned into the right choice. If we'd done research, we might not have picked it.
Dustin
Nate, I want to get you in this conversation here. You opted out of a previous life. You walked away from a job that paid you more in a month than most people make in a year. I'm curious, what job was it? What was your turning point to walk away?
Nate & Dana
The job itself, I was the CMO of a mortgage bank that I helped start. It was mostly coming through on W2 and profit-sharing. I was a marketing student in college. I worked as an intern and the marketing director for a couple of guys who were a few years older in a ticket brokerage. They grew that and that was in 2000. They started in 1997. I was there from 2001 to 2005. It was an earlier generation of the internet. If you can think back to mom-and-pop had a better chance, especially in any industry. Tickets were one of the ones that got caught up with eBay acquiring StubHub. TicketsNow was another big platform that came in and ended up acquiring us in 2005. It was a Wild West days of the internet. I learned a lot about internet marketing there. I was with that whole group from the time I was eighteen years old until the time that we talked about me opting out. We'd switched over into the mortgage industry after the ticket business. It had taken off. That company, when I was walking in here I was like, “There are many employees.” At this point, it's being out here in San Diego. We don't have anybody. I remember those days. We had 500 or 600 or 700 employees by the time I was departing. That's what it was. It was a big mortgage bank that may sound like high finance fancy, but it was run like an internet company.
I've never worn anything other than flip flops to work. Especially being on the marketing side, we lived the internet lifestyle even though we had a mortgage bank that was licensed nationwide. It is a cool experience. You're asking what the turning point or the genesis of it was. A lot of it was meeting people like Dana and yourself. It was over the years getting out and going to conferences and meeting other people who had the same skillset but had a totally different lifestyle. It was this innate desire to get out and travel and experience something different. That came to a boiling point by the time I was in my mid-20s. I never studied abroad. I'd sit there and watch Anthony Bourdain shows and be like, “I want to go to that place so bad.”
People would come back to the company. There was a guy who is also an executive at our mortgage bank who was the chief operating officer. He had taken a year-and-a-half and lived in Spain in college. He would regale me with tales of that. I was like, “I fucked up. You're back here, we’re the same position and you got to do that.” A lot of the wanderlust and the desire to get out and also to meet more people who I felt were my peers, my friends. People who I felt like I could be on their level and would inspire me to come out here and meet people in San Diego who were growing businesses are people all around the country. I was in Chicago and I was there for a day-and-a-half. I caught up with four different entrepreneurs, all of whom I had met in 2008, 2009 and 2010 at the events. They were all people that were like, “I could get out there and do something on my own. I'll be okay if I break free and go give this a shot.” I took the opportunity to say, “I'm 27. I don't have kids. I've got this opportunity. I have a skillset and a network and cash to go have fun. Hopefully, I land in a safe place and still have momentum if I opt out.”
Dustin
I want to get more into it, but you've got some secret sauce that I definitely want to tap into. You mentioned Show-Me Tickets, which you were behind the scenes helping grow it, but you've got LakeRentals.com, Plus 1 Marketing, Surety Bonds, on and on. It seems to me that you either know how to put yourself in the environment or start and create the environment yourself to create a successful exit. What's the secret? How do you pick these winners?
Nate & Dana
A lot of persistence, banging my head against the wall. A lot of talking to people and friends. The idea is they spark over conversations like this. It was one of the reasons why we started the podcast. We would always go out and have coffee and beers. We would throw events here in San Diego and ask people, “What are you working on? That's interesting. Here's an idea for that.” A lot of it was the genesis of running into people and having a network and having them bring something up that sparked an idea or saying they had a pain point. We had another business called Spread Effect that was launched purely off. One of my friends said he hated his link vendor for his SEO for his agency and telling me the budget he was spending and me saying, “Can I have it instead?”
That grew to a decent-sized business in a pretty short amount of time. There's been that end of it where it's constantly talking with other like-minded people. People who are excited, who are curious where ideas are sparked. They are looking at the Inc. 500 list and trying to decide, “How can I spin one of these businesses up that isn't maybe one of these categories?” There's an old-fashioned place. That's where the Surety Bonds idea came from. Also, interacting a lot with the colleges and university interns. We go back to my story. I was an eighteen-year-old college student working on an entrepreneurial endeavor which has given a lot of free reigns and a lot of run with it, Nate. I've tried to pay that back. That also allows you to kickstart ventures when you can ride the backs of smart, interested, hardworking people who are 21 years old, 22 years old and having them help power your venture. Staying involved with those groups in those universities usually leads to exciting ideas or people you can partner with.
Dustin
Is that why you taught at UCSD?
Nate & Dana
Yes, that's where it came from for sure. Dana teaches there real stuff. I talked about marketing, but that's definitely why I still go down to SDSU and UCSD and speak at business classes and entrepreneurs’ society and why I do mentorship stuff with people back in Missouri. Dana and I went to a wedding of a former student who I went to and spoke at his class years ago. He became an intern, then he moved out here. He ended up running our business. Now, he owns his own business in that same industry. He is 28 years old and marrying a girl from San Diego. Those types of stories are cool to be a part of, but it shows the formula so to speak.
Dustin
How did you guys meet? What was that first magical moment?
Nate & Dana
It's a good story. There was an event being held by a former chiropractor named David Klein. Everyone knows him as DK. DK was a chiropractor who had figured out how to use internet marketing for his chiropractic practice. He found himself around a bunch of internet marketers. He decided to create this networking event that was similar to Elite Retreat. They invited a bunch of the same people from Elite Retreat. Nate was coming out for that. I lived on the route between the airport and where the destination was. Unrelated to Nate, a guy was hosting food, a thing he had created called the Bacon Explosion. This internet marketer named Aaron Chronister was around since the beginning of the internet marketing days. He was dropping off Bacon Explosions for me to hold in my freezer for the next day. Nate used Twitter. This was probably the first year Twitter was even round and said, “Anyone going to ThinkTank?” They connected. Nate hitched a ride with the guy, ended up at my house with Bacon Explosion guy having a beer on my patio.
This guy lived on Camino La Costa, which is the street of dreams in La Jolla. It was everything that I had thought that I wanted. I was like, “This guy's doing it. He's in the place that I want to be.” His wife, Heather, was there. They were so cool and welcoming. I was sold right away on whatever this guy's doing. I want to do it too. We hit it off then a very romantic evening there in La Jolla. That house became the place where we hosted a lot of our early events that we started here in San Diego. We were saying like, “Let's keep this going. Let's have other people meet.”
Nate ended that event and said, “I'm going to move here. It'll probably be a year or more. Let's do something that we can collaborate with. I want to meet people in San Diego. Why don't you reach out to however many people you think would be cool to hang out with? I'll do the same. We'll have dinner.” We created this networking event that still exists now. We had three events in 2019, probably have another one. That’s the list of well-curated on San Diego entrepreneurs is about 175 people. We have 50 show up at any given time and hang out and be together. That was Nate's idea. We picked the people we wanted to be with. It was our way of letting them know real networking and say, “We'll do our thing. Let's hang out with people we want to hang out with.”
We started doing that even before you moved. When Nate would be out, we'd schedule one of these dinners and draw together what would become our crew of people that we were selfishly learning from. We get around people like that and you ask, “What do you do? How do you make $10,000 a month and not do anything but go ski a lot?” A lot of that turned into us learning like, “What are people doing to opt out? What are people doing this entrepreneurship in real estate that gives them power over their time in ways?” They're not out there announcing how they live their life. We learned a lot from those friendships and we're outing them all one person at a time on the show.
Dustin
Nate, had you already made up in your mind that you're moving to San Diego? Do you feel like having a Bacon Explosion and starting these dinners and networking group was a pulling force for you or were you already there?
Nate & Dana
I was already there. I was going to do it regardless. I knew that San Diego was an internet marketing haven. If you could live anywhere, where would you choose? It's proven itself out over the last years. That list of people, many people moved to San Diego and up on our list. There are guys and girls new to San Diego. She's here for whatever reason. I was drawn to it. From the time I was eighteen or nineteen, it's what made it more than a fling. It made it more than all this coming in for years. It made it like, “No, this is a place to build a life where you can be surrounded by a lot of people that can inspire you. You can become friends and also share a lot of projects and things like that. This is a great place for our style entrepreneur.”
Dustin
It's funny. I always consider myself an East Coast guy having grown up in Florida, in Tampa, in St. Petersburg. I was like, “It's either going to be Austin or it's going to be San Diego in my next thing.” Here I am in San Diego. I’m happy to be part of the crew. We've been throwing this term opt out around a lot and you guys define it in many different ways. I think we ought to define it. What does it mean to opt out of the lifestyle? Does this burn the bridge or chuck Corporate America behind and do it? Is this start a big enterprise that turns into a unicorn? What does it mean to opt out?
Nate & Dana
The term came out of a book I was writing. The book I wrote was originally called Reinventing Rich. It was my way of saying like, “I'm still rich, even though I didn't take that big exit.” I started fleshing out what the things that made my life feel rich were. Some of it was like the house that Nate met me at. It was a multimillion-dollar Spanish mansion on the coast. I had nice cars, but I hadn't done anything the right way. I hadn't had a big exit. I didn't have businesses with investors. I'd had failures, but I had cobbled together a lifestyle that was sustainable and gave me time and still nice things. I put this book together at some point. I was in Bali writing it while I was generating money from these businesses. I thought, “What is it I'm doing differently? I'm not dropping out, but I’ve definitely opted out.” I'm opting out of the rat race. I don’t buy getting an MBA is going to get you more money. I'm opting out of the educational system, the social norms, the expectation. For example, that you should live in the house you own. I have nine doors worth $5 million. I rented the house I live in. That's a big opt out mentality because a lot of people think that they're a schmuck if they pay rent and rent a house. Opt out became a theme, I guess, the glue that held the book together. When I came back from Bali, I threw the book at Nate. He was like, “That's a cool name.”
Dustin
Did you had Opt Out or was it Reinventing Rich?
Nate & Dana
I renamed it while in Bali. I don't like Reinventing Rich. I tested it on people. I asked my friends and family. They do what you did now, which is to give a little scrunchy face. That doesn't tell me enough. I threw Opt Out around with some of the people. I had been paying a friend who was a professional editor. People would nod at that instead of the scrunchy face. I was like, “I get it. I like it.” I came back with a draft written probably a few months away from publishing it. I gave it to Nate. I was like, “Can you read it and give me some feedback?” He was like, “I love it. It definitely speaks to our approach to life in business.” We threw together a concept of a podcast around it. Some educational products that we could use to help people get their version of the Opt Out Life. That's what we're doing for the last months.
Dustin
Nate, what are the things you've worked with? You've got the podcast. You've got an amazing platform. People taking courses and they're coming to you. You're getting this feedback loop. What are the biggest challenges or obstacles preventing people from opting out? Is it a mindset? Is it a lack of discipline? Everyone would like to opt out, but why don't people ever get there?
Nate & Dana
You're right that everyone would like to do that. I think that people like the name. It is almost good that you're like, “That's great. I want to do that. What is it? How can I define it for myself?” It's almost like a problem as much as a challenge for us to try to answer some of those questions. We get the whole spectrum. Dana knows. We get emails every day. Some of the people that we've worked more closely with or maybe perhaps better examples. We've worked with a lot of people who are in jobs who want to get out and also people who are already out and are wanting to scale that. Mostly, it is a combination of mental hurdles and a lack of someone to bounce something off of that pushes you forward.
We find ourselves being like coaches in a way, but intelligent coaches. Whether we're talking about someone who's gotten to the point where they want to create a landing page or they're creating a landing page. They want to push it out there to get some traffic and a test audience. Every time we have a conversation for seven minutes and we say one thing. They're like, “That's it. That's what I needed to hear and I'm off and running.” A lot of people lack a sounding board, a coach to push them over the edge. Whether it's a mental hurdle, something more practical, like one of those website questions, which is something that we had happened. A lot of it is more mental and awareness.
Before I moved out here, when I met all those people, I started to gain confidence because I saw other examples of this happening. Hopefully, what we're doing with the podcast is showing the huge array of ways that you can opt out. All these people are pulling it off whether it's being a digital nomad and living in Bali and making money off of freelance work. It's someone who has a job but considers themselves opted out because of the way that they approach their job and the way that they use it to travel and to fund other real estate investments which are going to be their path out down the line. It’s their long-term wealth building. I've been amazed at how different people can approach it. It's almost hard to have a good answer because it's everything.
If you were to say what's the most common obstacle to somebody getting out that life who has a job, it's the idea that they need to start a business that's no one's done before. They watch Shark Tank. They think they get the big idea myth. They think I need this big massive idea that's novel, that's going to shake the earth. The reality is those are stupid ideas that you'll waste all your money on. You're probably going to lose. People who should make bets on that or venture capitalists, Silicon Valley VCs that have taken exits or entrepreneurs who have made $100 million. Let them do the crazy wonky idea that no one's ever tried. What people don't realize is what they're doing is something that probably can be turned into a business. That’s a skillset. They are gaining. They don't realize how close they are to be able to turn that into a business that gives them control over their time. They focused on this gyration with their friends or family. At the office, “I’ve got a new idea.” New ideas aren't going to work. That to me is the biggest hurdle.
Along with that, there's maybe a failure to realize or a lack of understanding of what it's like for people like us who are often using one of those skills. Whether it's law or marketing, to allow ourselves to have the freedom to take shots to be an entrepreneur, to take a chance on something that gets big and maybe it doesn't. You live to fight another day by leveraging yourself as a lawyer. Well-enough, opted out, not working for a law firm, but doing it on your own to have the opportunity to do all the things.
The good way to say it is once you have a business that is pretty boring, it's a platform for you to fish for some big game. Hunt for the big game. It's a chip on the table. Nate and I have seen this repeatedly. We've made bets with some of our money, our time or both on some of those crazy ideas, but those crazy ideas you're not betting your life on them. That's what people think in a job is that it's all or nothing. If they could get out and have a baseline platform as we call it a boring business, then you're free to get around some cool people and throw a little money behind a venture that might make you millions.
I think it's hard too, if you're working 9 to 5 or 8 to 5, to then find the time to push out of it. That's a very common thing too. I'm exhausted at the end of the day. We try to coach these people through these programs. They're consuming some of our content. They're starting to do outreach to and starting to build a website. They putter out because I would too. That's hard. What works is if you cannot sell your time in that traditional fashion, do something. Whether that's selling your skill as a consultant more often than not for smaller chunks of time so you can have your afternoons open to going fishing. I find that even being back in Chicago, friends who have sold for eight figures and seven figures, they end up back in the same place eventually, too. I'm piecing some stuff together and then going out and going fishing again. It's hard to do that if you're employee number 47.
Dustin
We're all moved by the stories. You even said that having a podcast to give examples gives you confidence. What are some of the more fascinating stories that you guys have from the community? Either the youngest member, the oldest member of the tribe or maybe somebody that made the jump into a weird or unique business or side hustle. What comes to mind?
Nate & Dana
There are many. We've done 80 interviews.
Even people that are in the tribe.
We did that interview with Parand Tony Darugar. He is a smart San Diego-based entrepreneur. He had been with a business that had been VC-funded and poured in the midnight hours. He saw the thing. He had an offer to buy that the managers declined. A couple of years later, after a split sweat and tears, they sell for a fraction. No one makes anything. He’s been through these cycles. He finally decided he was going to do a lopped out business. He was like, “I'm going to do a little receipt app. I want to take a picture of a receipt and have it log that and tracking my expenses for the business.” He hunkered down with a one-man that's when Nate met him. He has a one-man office in Del Mar living his life where you could walk to the beach. That thing turned into a big thing that got bought by a big company that went public. I like the story because he let go of that myth of the, “I need to have that exit.” He built a life around the lifestyle business. It did turn out. To me, the real story of success is that there's so much serendipity. You have to avoid bad luck and those black swans that are negative. You've got to have a black Swan that is positive. In some event that's often out of your control, but you need to be out there, plan to have that come to you. I like those stories.
There are many, especially the consumer product ones stand out because they're tangible. When you can look at those and you’ll say, “There was nothing clever about that idea other than deciding to do it.” We've had Knockaround sunglasses and Dr. Squatch soap and Keeney bands and all these San Diego brands have done well online with some creative marketing on a pedestrian product. There are always a couple of points of audacity to reach out to a potential investor or to try to sell something or to walk in the door and try to sell something to a store or a buyer or to throw up an ad on Facebook. It's always inspiring to me to see those things and those things that turn into real businesses. Part of the reason those have stood out as well is that you get through the pain points. You’re in there like, “We might do $10 million this year.” I think a lot is approachable for people too. They're like, “I like sunglasses. I like shoes. I like soap.” I like those stories because even though it's not real estate investing, it sometimes puts people to sleep, digital marketing campaigns sometimes sound too far field. Some of the other stories we've had where the people are moving abroad. That's too crazy, but if you looked at this and said, “This is the thing I'm going to do.” We've heard many stories of that working out.
Salty Cali, it's a great story because they are a couple of San Diego girls. One worked at a surf shop. They made some jewelry together that they thought they might like for themselves. They thought, “Maybe we could sell it a street fair.” One of them, she had a friend at a surf shop. She worked at a surf shop. She put it on the counter. People bought it and she was like, “We sold all that jewelry.” They created a point of purchase display with some jewelry on it. They walked into a surf shop audaciously like, “If we made this, would you buy it?” The guy's like, “Can I buy it? Sell me that right here, the whole thing.” They're like, “We have to keep making these displays loaded with jewelry and show up at a surf shop and they'll buy it.” In fact, that's grown crazy. They find that trade shows works. They show up at trade shows. They ran out of purchase orders in their first trade show. These girls are a couple of Salty Cali girls. Salty San Diego girls decided to give it a try. That business is growing.
Dustin
I love that audacity of just walking in and selling it like, “What have you got to lose?” Sometimes the mindset stuff keeps us back. That's very inspiring. What has surprised you in building this tribe? This community? This business? Whatever you want to call it. What has surprised you the most?
Nate & Dana
There are multiple layers of the tribe. As we looked at the people we've interviewed, we're looking for entrepreneurs that have done things, what we'd say non-conventionally, but an Opt Out way. They're not like, “I took a business loan and I bought a franchisor. I went to venture capital and I raised some money and then I sold” Those are stories for Inc. Magazine. We're looking for alternatives, but what I've realized that it's the most interesting is how many consistent themes there are through those stories.
Dustin
What do you mean by themes?
Nate & Dana
One of them Nate coined early called the audacity to reach out, which is the thinking, “What's the worst can happen if I walk up to that person and say, ‘I'm Nate. I know you're this entrepreneur person. Can I ask you a question?’”
I might even add to that the audacity to show up because a lot of them we've put into that category are like, “I didn't want to go to this thing. I don't even know why I was going. I don't belong there. I went and I met my investor.” You get the sexy audacious stories as like, “We're going to fly to Western Samoa and pit the king.” This is the story of the show. That's pretty audacious. You sit there for five days and he finally talks to you and it all works out. Love that, but the audacity to show up as well, whether that was inadvertent or advertent. It’s something where whether it was an investor event or pitching at a competition or a kid's birthday party and bringing something up and being willing to ask questions or to show some curiosity. The audacity to be curious. There's curiosity about reaching out.
I was going to say that maybe the most surprising thing to me is the universal struggle of entrepreneurs, which I've known is there. You can see it spelled out every story. Maybe I was at a point where I wasn't happy. I knew I wanted to go do something else and I had the audacity and something started. Inevitably, down we go into this place. It can be a little bit early. It can be later. It can be when the company's doing $10 million in revenue. It can be at the point where you're running out of money. That is what is always there. Sometimes, it's real dollars and cents. Sometimes, it's a mental struggle with the entrepreneur themselves.
Maybe they don't have a partner to bounce stuff off of. Maybe they're distracted. Maybe the business is getting away from them for whatever reason it is. Universally, this thing is always a battle. It's inspiring and interesting to hear. I feel that there's more for us to uncover with that. There's probably more to pull out somehow, somewhere. Listen to most podcasts. You listen to and you read them. This is like group therapy and telling me about the problems that you went through. The podcast platform and the medium have allowed for so much more of that to come out. I think it's also a very human thing. It's something we relate to in the story, but it is there every single time.
Dustin
I feel like entrepreneurship or starting a business is the ultimate personal growth. I've never put this out there, but you're put into many situations, there’s struggle, money, sales, you've got to talk to people. Do you feel this way?
Nate & Dana
Yes. Most of us have to face our demons. If you don't, then you're going to end up with some bigger struggles.
You go back to the other side, where we're choosing to opt out means you're choosing that these struggles are going to be there. You're going to have to push through them. If you want to press the easy button and go back to working for someone else and in this context, that's what you're doing. I think it's part of it. This is why we signed up.
Entrepreneurs are typically voraciously reading. Most entrepreneurs make the mistake of letting the networking slide because they forget that networking isn't about selling. It's about connecting. They lose the therapy that you get from being around other people who are going to say, “I've totally gone through that already. Here's what I did. I empathize with you. It's going to suck for a little while.” All of those things. The other thing is you're going to fail. It takes ten ventures to have one that makes you millions and that means several. If you had success right away, then hold onto as much of that money as you can. The next venture might bounce back out of your pocket. Definitely, it's a self-help venture.
I think listening to our podcast and coming to any of our events is an exercise and therapy. It's therapeutic. You walk away from listening to it or coming to those events feeling better about what you're doing. Even if that hasn't given you a practical tip to apply to your business. I feel better after them because I feel that there's a tribe. There's a community. I realized there are other people doing it. It also gets you out of your own head. You read too much. You think too much. You put too much shit on the whiteboard. That isn't good for anybody.
Dustin
Dana, you've got some chops. Both of you have amazing chops in terms of building businesses or investing in businesses and exiting. How do you look at Opt Out as a business or business model? Is this more of a lifestyle? Is this your legacy giving back? Do you think about profitability? What's the long-term play with this?
Nate & Dana
It's funny. For a couple of smart business people, we haven't been very business-minded about how we've taken this on. We started with the experiment that we liked the idea of doing a podcast. We used the friends' equipment and did a test podcast. We're like, “This is fun. Can we do this even if we're not making any money?” We nodded. We thought, “Let's do the podcast and then see where it goes.” As it's evolved, we'd like to make money from it, a substantial amount of money. I don't think there's any reason we can't be like any other wildly successful online entrepreneur, educational platform. We've spent a lot of time experimenting with that. At this point, we're like, “Learn to teach.” We're learning things that we didn't know we didn't know. We are trying to figure out how do you scale, but stay true to the message.
For us, it is. We want people to get this, to connect with it because I'll tell you from having not had to take a W2 paycheck for years, it's cool on this site. If I can get people over here, I'd like to get them over here. I'm not selling them snake oil, but I do have to sell. I do have to find how do I productize? How do I communicate? How to deliver something that succeeds at getting you over here? If I can do that and make great money at it, then I'm fulfilling my mission. Several months in, to be honest, we're still tinkering. We're still playing. We've got three info products. We're still trying to figure out how to funnel those and not have people feel that they're being funneled and sold. You want people to want it. It's tricky marketing when you're trying to say like, “We're not slick salespeople trying to get you to give us your money. We're trying to get you to give us your money because we think you could use this stuff.”
It's TBD in practical terms. We hosted an event that was paid that went well. We've put out some courses. We've hosted. We've done a monthly membership training program. We've done a couple of other coaching products. We've been playing around, experimenting a lot and run the grand scheme of things several months since I have a business. That is not very long. We barely figured it out anyway. It's been interesting and hard. I joked about opt out. You want to do it before you even know what it is. It means something different to everyone. There are a lot of different components inside Dana's book, which is the initial blueprint for getting out of your job and selling that as a skill as a consultant breaking free.
There are doing online marketing. Dana has a pretty successful little online business he's had for a long time. There's the real estate investing. Some people fall into some of these categories of interests. Some don't. It's a complicated thing to productize. Sometimes it doesn't feel good to try to productize this, which is also a bit of a conflict as well. We love talking to people one on one in group settings, hosting our events, talking about this shit, but getting online and trying to put it into this checkout now thing is hard. In some ways, it's like, “I wish you didn't have to be. I wish we could always do it for free.” We'll see what the runway is for that. We know we have to figure something out.
Dustin
How do you stay true to the message, but also battle what every entrepreneur does, which is create? We want to create. We want to get involved in opportunities, in potential deals. What's your check and balance? What's your system to make sure you don't try to go start the next Facebook? The next big thing that's going to take you away from the lifestyle that maybe is going to put 500 people employees in a building. How do you keep yourself from going down that or are you great at that?
Nate & Dana
I had an event. It is like a website. We had a call center for a while. We ended up closing our call center. We kept growing the website. We ultimately exited the site after two years because it was at the point was like, “We got to do that or we get out now? That was a conscious decision to say. Do I want to hire 5,000 people? Do I want to raise a little bit more money and go after it? We have the marketing machine to make that a reality. It was certainly a conscious decision to say like, “I don't want. San Diego is deep inside me now. I don't want to get a big office and have a bunch of people in these problems.” I want to keep it lean, especially at the time when I have young kids. I like having that flexibility. I think right now there are points where you can try and make a conscious decision. Even if you have something that is successful. You can say, “Let's go out and try to exit this thing right now as opposed to digging in deeper.” Then going back to the drawing board and trying to figure out something else. There's one example of saying, “This is not the right time for me to go off and do that.”
Dustin
Do you have partners in that deal? It's easy if you're solo, you can make that call. You’ve got partners in there. Maybe they're older. Maybe they don't have kids. How did you guys come to a consensus? Did you know going in?
Nate & Dana
Maybe. It is luck in that situation. They're also fairly entrepreneurial guys as well. This wasn't their first one. There were going to be others as well. We lucked out on the timing. That's a good question though because we get a lot of questions about choosing partners as well. That insinuates what situation you're jumping yourself into when you're starting a new business. I got lucky on that one. I would be conscious of that early on when jumping into a partnership. We've had so many conversations about choosing partners and how and when that certainly can matter.
To your question, how do you not get sucked in? I remember a point where my brother made me list all the things I was involved with. It was eighteen different things like the branches, a trade show, an import-export business, a shoe company, a wine barrel business, three or four software ventures, a law practice, property management company, 100 doors of real estate with its own property management business. That's what I can rattle off. There were more. That taught me to be careful about how many hands you can play at the table. You can play more than one hand, but you've got to play one strong one that you play close and careful. The others have to be a couple of things. You dabble on side gigs that might scale. If they don't, sell them or you shut them down. I'm way more cautious. I've let go of the dream of, not that this was my dream, but many entrepreneurs that they would build a company in their county and their employees like, “We're up to 40. We're up to 90.” We even invested, Nate and I, with a business. The guy leaving to found the business was like, “We have a business that I only owned a little bit of. It had 90 employees.” He's like, “I don't even know why we have 90 employees.” I think it's the owner's ego.
They want to grow a business. That turned out to be bad because when the revenue dropped and they had 90 employees. We've seen too many of those stories. I'm cautious. I wouldn't mind having more staff. I think Nate and I look at each other when we look at our to-do list. We're like, “Two or three people would be amazing.” It would be exponentially better than us doing the things that we often do that we could delegate. We’re trying to build a business. We’re trying to figure out where you make money before you go spending it. No ambition for me to build something big, but definitely a caution to anyone who thinks that more ventures are better.
Dustin
You guys have tremendous background experience in this. Do you have a process for vetting or looking at deals aside from what's the time commitment? I know you've been in all different industries, both of you. How do you look at it? Am I going to get into this business? Am I going to invest? Am I going to donate some time? Am I going to mentor? How do you go through that in your head while still having the quality of life? How do you look at deals that way?
Nate & Dana
I'll tell you what I've been doing. I am quantifying my time.
Dustin
What does that mean?
Nate & Dana
I value my time. As a lawyer, at least I'm used to this. I can save my time for $500 an hour. If I'm going to get into a venture, I want at least that value in equity. I can say to somebody that, “I'll give you 100 hours for $50,000 worth of equity.” That's an easier way to ensure that I'm betting I'm still throwing in what could be money. I'm trading something of unequal value by doing that because it costs me less than $500. As long as I have some bandwidth. By doing that, they're going to be more cautious with how they use my time because they'll realize that everything takes twice as long and cost twice as much as you think it does. If you're going to have a lawyer, business advisor involved in the business, you only have 100 hours. You use those wisely. Don't burn them all up in the first three months.
That's a way to create a governor on projects. It ensures that I have some control over my time. I had ventures early on where I was like, “I'll take 5% of the company and worked crazy.” Years later, you're like, “How do I stop this hamster wheel?” That's one of my processes. The other is I’m cautious about the business and the people because what I've learned from watching successful VCs is they bet on people more than ideas. When someone's like, “This idea's amazing.” I don't care. I wonder, is the person going to be working hard to make this thing a success?
Dustin
How do you qualify that person’s past entrepreneurial experience?
Nate & Dana
Past experience. You hope that you have some relationship. You want integrity. You want to look at their life and say like, “Are they the kind of person that steps up when the going gets tough?” What have they done? Does that show some tenacity? Are they doing the things we know are good for business networking, being generous and curious and audacious?
How do they describe past failures in a very easy way to decide if it is someone you want to work with or not. Do they take ownership of it? Have them tell the story of what happened in the last place or it comes up inevitably.
It's okay if they have a narrative they've told on their resume that is shiny. They're willing to share with you the sad heart story that matters.
Who was responsible? Where are you the victim of something? I'm quickly turned off of people who were like, “Everybody's screwed me over.” I'm going to be the next one. That's one I always watch out for from experience as well. I did some private equity stuff. There is an infamous article that the founder, that private equity firm was do they treat their waiter well? It was popular across Canada because he's from Canada. That was his bellwether. It was having to deal with them. How do they treat people who are not important to that moment right there? That's a good one I think as well as evaluating things. That's tied to the opportunities because it doesn't matter how great the idea is. If the person that alongside it doesn't treat their waiter well or badmouths previous partners. I think more than anything I’m going to say no to stuff.
I always like to have a balance of a couple of ones that are long shots. I have a couple of websites that would definitely be described as that. They're taking advantage of a skillset I have where I feel like we have an unfair advantage. That's another thing I tend to bring up a lot like, “What's our unfair advantage? Is it our marketing ability? Is it our connections to people in the space? Is it something we know that other people don't yet know?” Having a few of those as flyers that might take off is always something I like to have. Otherwise, beyond that, it's more like, “Is this fun and interesting? Can I make a little money at it to bide my time to keep fishing?” That with the governor of like, “I don't want to spend too much time right now. When I have young kids, I want to spend time with them.” Balancing all that at once. You've got a mix of all three of those. This is how I approach it right now.
Dustin
That’s solid advice. I want to touch on networking. We've talked about it. You guys have invited me. I'm coming to one. Where do a lot of people drop the ball when it comes to networking? Aside from business card guy that walks in and forces, where do people drop the ball? How can we be better networkers?
Nate & Dana
You got to show up and be curious. You got to act like you're building friendships and that any conversation can end up being the valuable one. That's insinuating business card guy screwing up. Definitely, coming into it and we've said this so many times. Dana can probably go into his diatribe about it as well. Being curious about others like, “What are you working on? That's interesting. Tell me more. How can I help?” Being generous in that regard, but opening up conversations with like, “What are you working on right now? What do you see out there?” People that are going to enjoy talking about that.
Not what are you selling or what do you do? It’s what are you working on is great.
What do you see out there that's working right now? That kicks off conversations in the right way. I think not focusing on getting something specific out of the conversation or the event itself, forcing yourself to be there, having those conversations and enjoying it. At the events, if you show up, you're like, “This sucks.” You should have a different strategy. We've all been at events that suck. What's your strategy to get through an event that sucks? Is it to find someone that looks like you and walks over to them and asks that question, “What are you working on?” Is it to jokingly talk about how the event sucks? See how people react to that and then take them outside. We have a show on this coming up where we had some guests from the Opt Out Life ask us this question. We had them come on. We told them all of our stuff. One of the things I was like, “It used to be like when a lot of people smoke cigarettes.” I was like, “I wish I was a smoker because that was a point to go outside and hang out with people and have those conversations.” I've sat out there with them and smelled like smoke. I’m hacking it a little bit that way. Definitely, generosity and curiosity, the same things that inequalities that drive entrepreneurship and all this stuff.
In terms of a hack and all of that is everything we've been talking about. The hacking other events, look for what we call lobbycon. Look for the lobby where people you see a few badges and then you're with the smokers, you're like, “You still got your badge, John. You should hide that thing, Joe.” A lot of real networking like Nate and I have been to conferences where we have never registered at all. You're not giving $3,000 for a trade show you hate, but there are cool people there so you schedule it and then you ask people, “What's going on tonight?” You'll find out there's a private party, but it's not so private because someone who you met, Joe, is going to bring you to the party. Look for lobbycon and wherever you're going, look for how do you build real connections because you're not trying to sell anyone anything.
You can't network to sell. Sales is a marketing function. This is why we don't like the people in front of Whole Foods trying to talk to us. This is not how we do things. Networking events are an assault on your senses if they're there to pass out business cards and not there to build friendship and community. Look for ways to build community. What we talk a lot about is, at some point, build your own. Invite twenty people to dinner. Tell them, it's a pay your own way and hangs out and set the tone. Whether it's like, “I'm going to introduce everybody,” then you all hang out or let's do a quick like, “I got a problem in my life and my business.” One person solves it. Any way you do that, you're creating yourself as a bridge between a bunch of people with real connections.
That's an important point because you're going to be more strategic about it. We're saying cool stuff you can do. If you do want to be like, “If I go there and do that. What happens after?” I have to follow up with people. If you want a non-salesy leave behind, it can be. My buddy and I throw events, “They're not like this. They're more people hanging out. There are some like-minded people. You seem cool. Can I throw you on the list?” That was my leave behind for years. Now it's like, “Do you want to be on my podcast?” That's another thing that you can have as well. Throwing your own events sounds too hard. Starting a podcast sounds too foolish. You can figure out whatever that thing is. That's a strategic leave behind. It can be grabbing lunch too, for sure. Some people say yes and they don't mean it. Figure out what that thing is. Definitely, that will 10X your networking.
Dustin
One of the questions that I like to ask, which is good and it's good practice, what are you guys working on now? What are you most excited about putting on Opt Out now?
Nate & Dana
Opt Out, we’re continuing to do this for sure. Seeing where the journey takes us. Starting any business, you get through the first couple of years and then you figure out who you want to be. I am excited to see where that goes. It's always fun doing stuff with Dana. I am excited about that. Of course, we always have our side ventures. I have a couple of websites I mentioned. One is in IVF, fertility space, the other one is in DNA and genetics. Both of those are interesting spaces where there's growing consumer awareness. We've got some head starts and some advantages with the websites we've built. I'm curious to see where those go because those could end up being future exit opportunities for me.
For me, Nate and I launched a thing through Opt Out. It had a lot of mentoring and we were trying to sell for quite a bit of money. Running it taught us a lot about what we can deliver. We're going to re-spin that. It's called the exit plan. It's how to go from employee to entrepreneur. You're going to re-spin that as an info product at a lower price point with group calls instead of the personal one-on-one. We’ll see if we can get a larger group. I did this as an overview of the content for LinkedIn Learning. It launched months ago. It's had 6,000 views. In a month, that's a lot of learning people. I am getting some emails that are like, “This is cool. Thank you.”
That's a good indication that this exit planting is the right message. This is the right method. We have to finish building the funnels and these good marketers and get it out there and get people to understand why they need to give us some of their money to get access to the plan. I have a preview of their members of LinkedIn Learning. Check it out. I'm excited about it because it's resonating the message, the method, and all of that. Other than that, I have someone that might endorse my book that would give me a reason to spin it back out with a bigger name as a foreword. I am excited about that and negotiating the terms of that with a famous person who cannot be named.
Dustin
I appreciate that. For folks that want to follow you and Opt Out or at least learn about opting out, they can do it at OptOutLife.com. That's one of the best places. What about the good old socials? Where's the best place for folks to reach you?
Nate & Dana
We're on Instagram, but we have been lazy. We post once a week to remind people who are on our show. At some point, if we'd get our wives who were very good at posting onto their stories to post to the Opt Out story, you'd get a better snapshot of us living out that life. We're on Instagram and Facebook, Opt Out Life. We've got a Facebook group with a couple of hundred people in it. Probably more than that. I think it's cool because we react. People post stuff. We jump in and go, “People are asking questions, we're here.” It's a free way to interact with other people that have been on the show and with us. There's a bunch of smart people that take the lead and answer them.
Our most viral interaction goes through email. People want to tell us their stories. A lot of like, “I want to talk with Dana, Nate. I might have a specific question related to some of these concepts or I might want to talk about where I'm at with my life and where I might go next.” Dana@OptOutLife.com is a great email address to email.
I want to hear the stories. We have a spreadsheet of things that we can take from those emails to put on some future AMA show. We're going to say we got some cool questions. We're going to answer them as the podcast. We're going to experiment with that format.
Dustin
I appreciate you guys coming on down to the studio. I appreciate connecting with you. I'm looking forward to coming out to one of the shindigs and to mingle. I want to acknowledge you for putting forth the message. It's one thing to opt out yourself, but to put it into a book and then build a podcast helps people. That is a big undertaking and a big thing. Thanks for what you guys are up to in the world
Nate & Dana
Thanks.
You're welcome and thank you.

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