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David Duley of PlanGap: “Live a simple life full of experiences, not things”

Realize you can always get back in the working game if you like! It’s important to recognize that retirement doesn’t have to be permanent. Continuing to update your skill set after you retire will enable you to jump back in the game if that’s what you want to do, even if it’s mentoring others, volunteering […]

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Realize you can always get back in the working game if you like! It’s important to recognize that retirement doesn’t have to be permanent. Continuing to update your skill set after you retire will enable you to jump back in the game if that’s what you want to do, even if it’s mentoring others, volunteering or serving in an advisory role.


As a part of my series about the “5 Things You Should Do to Optimize Your Wellness After Retirement” I had the pleasure of interviewing David Duley.

David Duley is the founder and CEO of PlanGap, a product innovation company creating a new class of financial solutions — retirement insurance — a suite of “trigger-based” annuity and life insurance products that solve fundamental financial issues for retirees. The company empowers people to insure themselves against disruptions to their retirement income, providing solutions for those worried institutions have made financial promises they cannot, or will not, keep. David lives in Atlanta, where he graduated from Emory University’s Goizueta Business School.


Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share the most interesting story that happened to you since you started your career?

A few years back, I was told I would be meeting a business legend I had read about for years and who was involved in some of the most consequential financial decisions our nation and the world have made over the past few decades. The purpose of the meeting was to get feedback on my current company and its feasibility.

In a not-so-genius move to prepare for this meeting, my right-hand-man suggested I watch a movie in which an actor played the role of the gentleman I was about to meet. As it happened, the portrayal of this person by the actor made me exceptionally nervous. There were times while watching the movie where I would look at my colleague and say, “I am going to walk in a room with this guy and expect to survive?!” I didn’t sleep well that night as I contemplated meeting this titan of industry.

While my team and I rode the elevator up to the meeting, I remember telling them there is a 95 percent chance that on the elevator ride down we will be out of business because our “big idea” will have been shredded for reasons we don’t know or haven’t contemplated.

I recall walking into the room and seeing him stand up, come over, shake my hand and say, “This big idea of yours has me intrigued, let’s dive in.” He broke out a printed copy of our presentation that was fully marked up. We began answering his questions for the next hour and a half. Ten minutes in, I remember thinking to myself — I’m still alive, still presenting and actually have good answers to the questions being asked.

As the conversation came to an end, one of our advisors who helped arrange the meeting asked this gentleman point blank: Can this idea be done? After sitting in silence for what seemed like five minutes — it was probably more like 10 seconds — he said, “Yes, I think it can be done and understand why people would want it.”

I thanked him for his time, feedback and the work he did to prepare for our meeting. His preparation was exceptional and showed he cared to figure how to do it rather than give all the reasons why it couldn’t be done.

Later that night, I sent a thank you email and asked if I could keep him in the loop from time-to-time. To my surprise, I received back a long, thoughtful email in which he thanked me for challenging the status quo and coming up with something truly unique. He asked me to not only stay in touch, but offered to be a sounding board/advisor as we worked to bring it to market.

Today, I would call him not only an advisor to the company but also a friend. It is one of the most surreal outcomes of my entrepreneurial career, and I feel lucky to have had that experience and his friendship.

Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or take-away did you learn from that?

As an entrepreneur, you often have to move fast. Many years ago, I planned a trip to New York City to attend a dinner an advisor had arranged because he thought those attending would be good resources for me and my burgeoning company. My conversations with this particular advisor are always quick and efficient, so I booked my flight and hotel as soon as he told me the date.

I arrived at the dinner location about 15 minutes early (primarily because I am not very good at getting around New York City) and waited for the group to arrive. The time for the dinner came and went, and I hadn’t heard from my advisor. He, too, often arrives early, but I thought he must have gotten caught in traffic.

By 7:45 p.m., I texted my advisor and asked if everything was okay. He said yes, he had just finished dinner at his home. I replied, “We have dinner tonight planned with your friends in NYC.” He calmly told me, “Dave, that dinner is for next month on the 22nd. Enjoy NYC, I have to get back to the family.”

Needless to say, I just heard the word “22nd” and completely missed the month (no doubt I was multitasking). This incident proved to me that I was a terrible multi-tasker. In fact, I think most people are. I am most productive when I take one issue at a time and work until it’s completed — or until other feedback is needed — and then move onto the next problem/issue or opportunity.

But the dinner alone at the bar was nice…

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I started my first company when I was 23 years old. For a variety of reasons, I shut it down at age 25. It was one of the first true failures of my life, and I had a really hard time understanding how some issues, especially those outside of my control — like the dot com crash — could lead to so much damage for me, my investors and advisors. One of my advisors, with whom I would meet once a quarter for breakfast, reached out after we decided to close the business and asked if he could see me.

I met him at our normal breakfast spot. I was fully prepared to hear about all the things I could have done better (there were a lot!). Instead, the first question he asked me was, “How are you doing?” (like, personally). I told him what I was struggling with, especially the idea of letting him and others down and losing their money; that I couldn’t believe what was happening and didn’t know what to do to move forward. In my young eyes, I was a failure since I didn’t turn that company into a success. I felt like I had broken promises, and that really bothered and affected me.

I told him I needed time to think so I was returning home to Michigan. At that moment he said, “But you are coming back to Atlanta, correct?” I told him I thought so but wasn’t sure. In my head I was thinking, “Dave, you have no money — actually less than zero because of credit card debt — and it’s going to be a long time before you can afford to get back on your feet.”

He must have been reading my mind. As those thoughts went through my head, he reached into his wallet and handed me a check for 10,000 dollars and said, “I know you would never ask me for this, but I know you need it. This is not a gift, but there is no timeline to pay it back. Get back on your feet, come back to Atlanta after you’ve had time to think, and continue to do great things. I believe in you.”

This was one of the greatest gifts I received in my entire life. It wasn’t just the money but the affirmation that I wasn’t done, that I had more to do and there were people who, despite this setback, still believed in me.

I came back to Atlanta after three months and started the next phase of my life. I paid back my friend within a year. A few years later I started another company, and a few years after that I sold it.

My friend loved to travel and, because I’m from Michigan, we would always talk about how much he and his wife loved the movie Somewhere in Time. Filmed on Mackinaw Island, it’s a magical place in the summer in Michigan. A year or so after selling the company, my friend became ill. When I learned about it, I knew I had to do something: Create a magical experience to not only thank him for believing in me but also to spend another unforgettable moment together.

That summer I took him and his wife to the Grand Hotel on Mackinaw island. We did everything first class. He told me at the end of the trip it was one of the best trips of his lifetime (and this guy traveled a lot!). A year later my friend died. I look back at the decision to “thank him” for believing in me as one of the greatest moments of my life. I felt lucky I was able to create that memory together, and I still miss him today.

What advice would you suggest to your colleagues in your industry to thrive and avoid burnout?

I have a painting in my house of a man next to his boat that is stuck in the mud near the shore as the tide rolls out. He has a rope in his hand, and you can look at the painting and imagine his thoughts: “Do I try to pull this boat out of the mud right now or do I just wait for the tide to come back in tomorrow?”

Trying to pull this boat out of the mud, by himself, is nearly impossible. Waiting for the tide to come back in tomorrow will certainly get the boat out of the mud.

So many of us think we can change massive forces, like the tide, in our own business and life. I still struggle with this today. So it is important for me to step back from time-to-time and assess whether or not I am fighting the tide or acknowledge where the tide is, what it is doing and make the best decisions to wait or work.

As an impatient CEO, this lesson has been, and still is, one of the hardest for me to follow. But when I make business and personal plans based on the laws of nature and business, not by changing them — but instead understanding them — it sure seems a heck of a lot easier to get my boat unstuck.

What advice would you give to other leaders about how to create a fantastic work culture?

I think it is becoming harder and harder for leaders to create great work cultures because of the trend of the current American culture.

In my experience, finding a breakthrough in innovation means challenging people’s beliefs, how they arrive at solutions and how they see the world. There is no right or wrong answer, there is just a process by which we can break things apart and then build them back up better.

In our world today, asking people to challenge each other is becoming harder and harder. People are more easily offended, on a personal level, when discussing their work, ideas and outcomes. I believe this culture and value shift in America is stifling our ability to create new technology, innovation and products. People are too afraid to speak up for fear of offending someone. People would rather just stay quiet, which constrains the spirit of innovation.

My job is to create a place where virtually anything can be discussed. That’s why, during the brainstorming and solving modes of my company, there are no bad ideas. There can be many wrong ideas, but that doesn’t make them bad. The more wrong ideas we discover, the closer we are to the right ideas.

As leaders, we have to create places where people are able to share crazy ideas, defend those ideas and see what sticks. I would much rather have ten bad ideas shared than a culture in which people are too scared to voice their thoughts because they think they may make others uncomfortable.

It’s amazing what you can learn about people, both the yin and yang, if they feel like they are in an “idea safe space.”

Ok thank you for all that. Now let’s move to the main focus of our interview. Retirement is a dramatic ‘life course transition’ that can impact one’s health. In some cases, retirement can reduce health, and in others it can improve health. From your point of view or experience, what are a few of the reasons that retirement can reduce one’s health?

I think there are a few key reasons people’s health may suffer in retirement:

  • Lost sense of purpose. So many people are wrapped up and see their identity in careers, jobs and titles. Often, it makes people act like they no longer know who they are. Because of this, I think it’s important for people to think of retirement as a “next chapter” and give some thought to what they want to accomplish.
  • Money might be tighter. More people than ever are entering retirement with debt and other cash flow obligations. Often, people are on a “fixed budget,” and that constraint might feel like a prison.
  • Broken promises. So many people count on “other institutions” to provide for their retirement security, whether that is Social Security, pensions, deferred compensation or the performance of Wall Street. As those institutions become more volatile, people who count on these institutions — and the vast majority of us do — feel like they are no longer in control of what their retirement years will look like. These concerns led to the creation of my company, PlanGap.
  • Loss of relationships and friendships: My uncle lived to be 93 years old, and I vividly remember him telling me about all the funerals of lifelong friends and family he attended over the last 20 years of his life. He never contemplated life without those people around. I think one of the absolute keys to health in retirement is continuing to build, nurture and foster relationships with people.

Can you share with our readers 5 things that one should do to optimize mental wellness after retirement? Please share a story or an example for each.

  1. Realize you can always get back in the working game if you like! It’s important to recognize that retirement doesn’t have to be permanent. Continuing to update your skill set after you retire will enable you to jump back in the game if that’s what you want to do, even if it’s mentoring others, volunteering or serving in an advisory role.
  2. Don’t do or buy anything extravagant during the first six months of retirement. Ease into it and then decide what you need and where you want to go. For example, downsizing your home at a time when you’re suddenly spending much more time at home is a decision you might want to make after easing into retirement for several months.
  3. Exercise and meditate (check out Ziva Meditation…Emily is a rock star). Getting the blood pumping helps clear the brain and gets the right chemicals going through the body. Meditation helps get the mind right for the adventure of the day.
  4. Find something new to learn and embrace the struggle of learning. Research consistently shows the immense benefits of exercising your mind as you age. While many people think of taking up a musical instrument or learning a new language, which are great ideas, there are also a host of rigorous online courses offered by top universities that help you cultivate an entirely new skill set related to your past career. If you think you might want to dabble in the work world at some point, these courses are a great way to stay sharp.
  5. Live a simple life full of experiences, not things. This never ceases to be true, even in retirement. Acquiring things tends to come with additional costs, but experiences can be enjoyed for the rest of your life without having to live with additional financial — and mental — burdens. Today’s rental economy makes it easier than ever to enjoy a variety of pursuits without owning all the toys and gear.

In your experience, what are 3 or 4 things that people wish someone told them before they retired?

  1. If you retire young and have a lot of friends your age, you aren’t going to have many people to hang out with during the day. They are still working!
  2. Be prepared for a new type of work. Doing something meaningful always involves “work,” but retirement affords you the opportunity to do the kind of work that energizes you the most. Don’t ever stop learning and finding ways to put those skills to good use.
  3. Always create new friendships. A business leader that I respect once said the two things that help him learn the most are books and new relationships. The latter is harder to do in retirement but more important than ever.

Is there a particular book that made a significant impact on you? Can you share a story?

Zero to One by Peter Thiel and Blake Masters.

As an entrepreneur, I think this book is one of the most well written and powerful books on innovation. After selling my last company, I searched for years trying to figure out what I was going to do next. After reading this book, I committed to myself, and told others, that I was waiting to come up with a “zero to one” idea. Most people thought I was crazy. Maybe the jury is still out on that.

This book provided a roadmap for me to look at new ideas, companies and investments and measure them up to the “zero to one” standards.

I met regularly with a group of five entrepreneurs and shared my intention, based on this book, to wait and look for a “zero to one” idea. They encouraged me to get a job while I figured it out because the task seemed too daunting. It took a couple of years of exploration and looking at companies and investments until I had the idea for PlanGap, the first company pioneering a new category of insurance called “retirement insurance.” We’re starting with products that help people protect their promised Social Security benefits from potential government reductions.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

After I sold my last company, I was getting off a plane in my hometown of Flint, Michigan and saw the headline of the newspaper at the airport: “Flint #1 again in violent crime and arson.” I thought to myself, “How in the world did a city among the top five in per capita income 60 years ago fall so far?”

This set in motion what would eventually become a book I wrote called, “I Can Fix America: 52 ways you can make the United States great again.” Yes, I was ahead of my time with that slogan!

I was (and still am) frustrated by the state of our country and the finger pointing that accompanies almost every major issue we as Americans face. Instead of people looking inward to fix issues, we have gotten into a habit of blaming others.

The purpose of my book and subsequent podcast with New York Times bestselling author Robb Wolf — The Controversial Truth — was to show people that they have an amazing ability to control many of the issues they worry about in their own lives and communities. Instead of getting online to argue with people, my book gives you concrete ideas that you can put into action today to positively affect the outcome of the issue you are worrying about.

It is an anti-bitching, get-to-work coffee table-style book designed to inspire and challenge people to take action, not just talk.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

Before I make any major purchase, I think of a great quote in one of the best movies of all time: Fight Club. The quote is, “the things you own end up owning you.” I am extremely careful never to buy anything that could somehow “own” my decisions or make me do things (or work somewhere) because I have to pay a bill. So many people I know, mostly the “successful ones,” buy things that just keep them locked into a job or career they might not love. They can’t leave because of the mortgage, car payment, benefits, golf club fees, etc. That doesn’t sound like freedom to me.

I make it a point to never own anything that can own me or my decisions. By sticking to that formula, I ultimately have the freedom to wait, assess and do the things I truly love doing because I want to do them, not have to do them. And, because I love doing them, I am often good at them.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Yes, in 2012, my then girlfriend bought me tickets to Tony Robbins’s Unleash the Power Within seminar as a birthday present. I thought, “Ugh. What am I going to learn in a room full of thousands of people for four days?!” I truly thought this was something that my girlfriend wanted to do disguised as a gift for me. So, I went along.

Thank God I did. My work with Tony Robbins has been some of the most game changing investments I have ever made. I remember coming back from the weekend energized, inspired and clear about what I needed to do, change and execute to live my life to its potential. I literally see the world differently because of what I’ve learned about myself and the human condition through Tony’s work.

Since then, I have attended and taken probably close to 50 people to various events. In fact, I have a deal I offer to them that is very simple: “I will pay for your trip. If you don’t like it then you owe me nothing. However, if you do like it you owe me double what I paid.” To date everyone has liked it, and no one let me pay. But the offer still stands.

I would love to meet Tony some day and thank him in person.

What is the best way our readers can follow you on social media?

https://www.linkedin.com/in/david-duley-ab7528/ or email me at [email protected]

Thank you for these fantastic insights. We wish you only continued success in your great work!

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