“You have this amazing power to take invisible ideas and make them a reality”, with Dana Robinson.

“Your eventual success will be the culmination of many little successes and a couple of big failures."

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

I recently had a great time learning more about Dana Robinson and his growing following of individuals living life in a particularly interesting way.

Dana and his business partner Nate have created a community of entrepreneurs and individuals who live their life based on life style, without ever sacrificing their ability to earn an income.

Below is a glimpse into the mindset of the man behind the life style choice of Opting Out.

What is your elevator speech on your professional career: who are you, what have you done and how does that translate into value for your customers?

“To many people, I’m a corporate and intellectual property attorney. But, the truth is that I’ve spent my adult life being an entrepreneur. I started a landscape company when I was 19, and grew it for four years and sold it when I opened a coffeehouse at age 23. Since then, I’ve owned or co-founded a dozen different ventures, including a shoe company, a wine barrel business, a trade show, two property management companies, software ventures, and an audiobook business that sold to a private equity group. I’ve owned 90 units of apartment complexes, and now run a scaled-down real estate portfolio. But, my success isn’t taking a big exit from my ventures; it’s in finding a way to live the life I want.

“I reached a point where I realized that I wasn’t going to cash in on a big home run and decided to reorganize my life so I could move to Bali for a year or more. I extracted from American life, kept my business investments going and became a sort of “digital nomad.” While living in Bali, I wrote a book about my experiences, entitled Opt Out. It has my formula for an alternative type of success that doesn’t require the constant grind, or working for years with the hope of taking a big exit. I partnered with Nate Broughton to launch the Opt Out Life podcast, where we interview entrepreneurs who have found a way to live the life they want through business and side gigs and alternative approaches to business, life and money. We connect with the Opt Out community through a Facebook Group and through our own platform at

Let’s show everyone you’re a normal human being. What’s your personality, hobbies, favorite places to visit, pet peeve? Tell us about YOU.

“I’m a surfer at heart, although with waves close to my home, I find myself not surfing unless the sun is out and water is warm. Travel is my hobby. In 2018, I’ve been on a half-dozen trips: Bali, France, Denmark, Sweden, Hong Kong, Portland, Las Vegas, and more. I paint oil-on-canvas, although don’t have much time to spend on it these days. I don’t have any pet peeves, but I don’t like arrogant people.

“I’ve raised a daughter who is now 24 years old and done with college. With parenting in the rear-view-mirror, I spend a lot of my time mentoring. I cofounded the IP Law Clinic at University of San Diego School of Law several years ago, and I teach trademark law at California Western School of Law. I speak and teach on legal and business subjects and as a panelist whenever I can.”

What is something about you that most people don’t know that would surprise them?

“Many people don’t know that I was once a pastor. I have a B.A. as well as a M.A. degree in theological studies. I’m free of church now, but have respect for people of faith. I can talk about religion openly and sometimes that surprises people.

“Another thing people may not know is that I’m mechanically inclined. I can build things (woodwork, for example), and work on cars. I still do the brakes on my own cars, although with my Mercedes SL500, there are limits on what I can do.”

What are two examples of how you consistently work outside of your comfort zone and how has that impacted your personal and professional growth?

“If you are going to succeed, you have to do things that have risk. And, by doing things that have risk, it is a natural reaction to be in “fight or flight” mode. It’s our instinct to be ready to run when a tiger chases us, or fight when that’s no other option. But, that “fight or flight” mode creates a type of stress that we don’t want (or need). The challenge for most entrepreneurs is how to be constantly “at risk” of failure, without triggering the stress response that is natural to our instinct.

“The key, in my view, is summed up in a lesson I learned in motorcycle training. To keep safe on a motorcycle, you have to avoid going into fight-or-flight mode. You do this by relying on your knowledge and training. It seems like I am always outside of my comfort zone in some way, and that creates the natural inclination to stress-out (fight or flight mode). To move out of that mode, I remain conscious that my life is not in danger (the tigers are made of paper). I then rely on my knowledge and training to push through the discomfort and make smart decisions that aren’t driven by the wrong instinct.”

Many people say success correlates with the people you meet in your life. Describe two that most impacted your success?

“Success does correlate with the people you know. However, many people make the mistake of trying to expand their network through “networking” in ways that doesn’t necessarily translate to success. I’m big on networking, but not necessarily going to an event, wearing a badge and passing out business cards. My best networking has been finding ways to get around cool people and just have regular conversations. No selling. Often no handing out cards. I go to events to be curious and ask questions so that I can learn. I also go to be generous, offering my knowledge and experience to anyone who I think I can help. The combination of curiosity and generosity will always bring you into positive relationships. And, most of the great opportunities in my life have been based on those relationships. Co-founders, investors, vendors, mentors, mentees, all have come from putting myself out there with curiosity and generosity.”

Discuss one of the lowest points in your life personally or professionally and how it helped you get where you are today?

“I think the lowest point in my life was when the real estate market went flat in mid-2007. I had two large projects in escrow (as the seller). I was going to take a very large exit if the properties sold. Then the buyer dropped out and the market went silent. We couldn’t shed the projects and in 2008, when the entire market went south, I was holding properties that dropped in value from a total of about $15 million to a total of just about $2 million. I couldn’t escape it and was paralyzed as I watched my net worth go from a positive $5 million to a negative. I owed more than I owned…by millions.

“I was determined to survive the downturn. I held all but one property, and emerged from the losses in 2014, recovering enough to keep my seat at the table. Having lived through this season, I have rethought life, entrepreneurship, real estate and just about everything else. I don’t think I would have the perspective that I have now if I had just cashed out. I may have even just put that profit into something else that could have gone downhill in the end. I wouldn’t have gone to Bali. I wouldn’t have the Opt Out life that I have now.”

All entrepreneurs have sleepless nights. We have a term we use with our clients called the “2 a.m. moment.” It’s when you’re wide awake and thinking not-so-positive thoughts about your business choices and future. Describe a 2 a.m. moment (or moments) you’ve had and how you overcame the challenges.

“Entrepreneurs are always going to have those 2 a.m. moments. I’ve discovered a few unique hacks that can help make them more tolerable. First, I once heard that the emotional response to anxiety is very close to the physiological response to excitement. There are times when you just have to trick your brain by looking at the “thing” as an exciting opportunity. You just re-frame it as something that you are excited to resolve. And, in many cases, your brain might just be trying to resolve it for you when you are in that wakeful theta brain wave state.

“Here’s another cool hack. You have to remind yourself that you have already faced similar problems and solved them. You can solve THIS one because you’ve always solved every other problem before. If you were able to step into the future after it is resolved, you’d say “hey, I DO solve this in the future…so there’s no need for me to stress over it now.” I described it this way to one of my law school classes: Young Harry Potter is always stressed out about why he can’t cast a patronus…until he uses a time-turner to go into the future and he sees himself cast a patronus…then when he’s back into the “now” time, he realizes that he CAN cast a patronus because he just peaked into the future and saw himself do it. Life is like that. You can do it. If you embrace that, it’ll take some of the edge out of your 2 a.m. challenges.”

The concept of mind over matter has been around for years. A contemporary description of this is having mental toughness. Give us an example (or two) of obstacles you’ve overcome by getting your mind in the right place (some might call this reframing the situation).

“Napoleon Hill taught that Thoughts are Things in his ever-popular book Think and Grow Rich. He had a very mystical view of this and believed that there was a type of energy that transmitted between people’s minds and the divine. If you thought something, you could bring it into reality. In my experience, there is truth to the idea that “thoughts are things.” But, I don’t think we need to look to the divine or mysticize the concept. There is a truism that needs no spiritual explanation. If you have a thought, you make it a thing. If you put your mind to any task, you naturally DO that task. Your invisible thought becomes a reality.

“Many people don’t realize that this principal is operative all the time. And, it becomes a problem for highly creative entrepreneurs because they have too many ideas, and therefore they bring too many things into reality. That’s right. We create our own problems by underestimating our capacity to create things. How many entrepreneurs do you know that have too many irons in the fire? Most. They are their own worst enemies because they have brilliant thoughts that they bring into reality without considering the consequences on their time and energy. My principle is to keep my projects to a minimum so that I don’t dilute the good ventures with “good ideas” that will take my time and attention away from what really matters.

“Remember that you have this amazing power to take invisible ideas and make them a reality. And, avoid bringing too many new babies into the world. Focus on raising the children you have! Channel that creative energy toward building and growing the ventures you already have, and not on giving birth to new ideas that you accidentally bring into reality.”

What is the best lesson you learned from your worst boss?

“Make people feel great about what they are doing. Give them credit (and compensation) that you would want in their position. The best people need to feel empowered to build a future for themselves. That means sharing power, profit, and credit for what they are doing.”

What are your “3 Lessons I Learned from My Most Memorable Failure”?

“One of my ventures that failed provided many great lessons. I don’t even need to go into the weeds to explain the business because the lessons apply universally:

“Lesson One: Don’t chase shiny new objects. New ideas are amazing and trigger hope and optimism and energy like nothing else. But, once the dust settles, you realize how much work there is to bring that idea all of the way through to profitability.

“Lesson Two: People matter. Your partners are going to make or break your venture. If you partner with someone that doesn’t pull their weight, it’ll doom the business.

“Lesson Three: Money matters. You need to consider the investment ahead. You need enough runway to go twice as long as you expect.”

What unfiltered advice do you have for aspiring entrepreneurs or business owners looking to catch their big opportunity?

“Your eventual success will be the culmination of many little successes and a couple of big failures. Be ready for things to go moderately well, but not be home runs. Make those base hits count. Learn from the base hits, and if you get a chance for a small payout, take it. Then also be ready for something to fail hard, and pick yourself up and go at it again. Five or 10 years later, you’ll be an “overnight” success. Just keep forging ahead through the things that don’t quite make it, and persevere in the things that could take you down.

“While you are doing your adventures and misadventures, do two things: 1.) build real relationships with good people; and 2.) learn like crazy. You’ll find that all of those relationships get you through the tough times and one of them will probably be your home run partner, or make that connection for you. You’ll also find that you need the wisdom of all that you’ll be learning in order to make that big opportunity work.”

Looking back, what was the most non-conventional way you landed a memorable deal that made your success turn in the right direction?

“I was at a local bar having a drink and ended up having a conversation with a small group of people. It turned out that one was Dan Caldwell, the famous founder of Tapout apparel.

“He and the others were in town for an event for public speakers. He invited me, got me a discount and I attended.

“I can remember at that event realizing that I needed to focus my path on speaking, finish my book and move in a new direction. It all started by just being friendly at the local watering hole when some out-of-towners rolled in and started chatting.”

What is your favorite podcast(s) you’re listening to currently and why?

“The Opt Out Life which I host has been fun because I’m learning from my guests. Other than that, I love How I Built This with Guy Raz.”

What is one “efficiency hack” you use consistently in your life to keep your time and mind free to focus on your strengths and passions?

“I have my staff organize my emails so that I can only “react” to urgent emails and spend less time on email “tennis.””

What are you currently working on now?

“I’m working on building a membership program for entrepreneurs who want to “opt out” and create a business that gives them freedom. My business partner Nathaniel Broughton is a serial entrepreneur like me. We’ve both been through every business cycle, from founding to sale, and virtually every obstacle to success. We’ve also learned to maximize our side hustles so they give us more free time, rather than becoming distractions.

“We are bringing our members a variety of resources. We have “ask me anything” sessions, weekly office hours for direct consulting, monthly “legal questions” webinars, and a host of elearning that comes with the membership. We also have a high-touch service where Nate and I bring ourselves into the life of an entrepreneur for three months and help them transform their business into an Opt Out lifestyle business.

“We hope to launch local regional meetup groups where other Opt Outers can connect and network with other like-minded people.

“And, we’ll be launching a second podcast in 2019 focusing on the things entrepreneurs can do to get off the hamster wheel, grow their business and work less.

“We encourage people to email us directly, but the easiest way to stay abreast of everything is to sign up for the email list:

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...


Creating “Bottomless Wonders” For Communities

by Alexandria Cannito

Monica Williams and Dana Roberts: “To empower every girl. From the inside out”

by Ben Ari

“Have short term, not just long term goals”, With filmmaker and actress Dana Marisa Schoenfeld

by Yitzi Weiner
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.