Richard Jardine: “Your words don’t need to be complicated or quoteworthy”

…The movement I would inspire would be one where people all around the world shared encouragement, advice, and wisdom with loved ones throughout their lives and beyond the grave. I’d make it so nobody had to live with the same void that I have without words or pictures from my father. I had the pleasure to […]

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…The movement I would inspire would be one where people all around the world shared encouragement, advice, and wisdom with loved ones throughout their lives and beyond the grave. I’d make it so nobody had to live with the same void that I have without words or pictures from my father.

I had the pleasure to interview Richard Jardine.

Richard was raised in a multicultural family in Massachusetts public housing. Although his childhood was plagued by systemic poverty and inequity, he was determined to build a better life and help others do the same. To start, he enlisted in the US Army National Guard where he graduated top of his class in avionics school.

Since graduating aviation school, Richard has built several successful businesses. In 2002, for example, Richard founded the Beverly Hills-based Clear Media. Clear Media initially focused on creating viral brand awareness for sports and entertainment professionals. Over time, it expanded into putting together several successful investment opportunities for private equity firms, hedge funds, and high-net-worth individuals.

Richard never lost his desire to help underprivileged families find safe, affordable places to live. Because of this, he was inspired to build a portfolio of properties in the Midwest, which he operates using a neighborly, service-oriented approach. In an industry rife with adversarial landlord–tenant relationships, Richard’s approach put people over profits and has developed mutually beneficial relationships with his tenants.

With everything he does, Richard’s goal is to leave the world a better place than he found it:

“If I’m unable to inspire and help people to join me in leaving this world a better place than when I entered it, I was never a success at all; I was just another guy who died with more money than I was born with.”

Richard’s latest project, Skypod, continues this mission. Skypod uses patent-pending technology that empowers people to create digital time capsules containing photos, memories, messages and other important information for the people they love. These digital time capsules are encrypted, delivered immediately, then made viewable to loved ones up to five years in the future.

Each recipient keeps the Skypod in their possession and can see the time and date the sender set for them to access it. This doesn’t just help people leave a legacy that reaches beyond their physical location and living years. It also helps build anticipation and excitement as recipients eagerly await the date they can access the digital time capsule created by their loved ones.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

My biological father died when I was a young child and not a day has gone by when I haven’t wondered about him. I’ve wondered how he felt about me. I’ve wondered what he looked like, what his voice sounded like, and what advice he would have given me during tough times in my life.

My biological parents weren’t on great terms when I was young, so my mother never told me much about him. I don’t have a single picture or letter from him. I know very little about him. My entire life, I’ve gone without a single piece of life advice or fond memory of him, so I’ve always felt like a piece of me was missing.

I spent years looking for ways to overcome that feeling. I became obsessed with achieving business success, thinking if I made it out of poverty, I’d find meaning that would help fill that void. But no matter how well I did in business or how many cars or watches I collected, the empty feeling never went away. It just made me look successful on the outside. Inside, the void was still there.

Eventually, I realized the deficiency had nothing to do with money. It was a lack of meaning and connection. When my biological father died, he left me nothing. What if I died? What would I leave for my family? A few watches? A car or two? What kind of legacy is that? It’s not. I had no deep meaning in my life and no connection to an important figure from my past, my father.

If I continued doing what I had been doing, I risked leaving the same lack of meaning to my kids when I ultimately died. So, I decided to dedicate my life to meaning over money, to people over profits, to legacy over luxuries. My mind raced. I needed to build a better legacy to pass along. And what if I could help others do the same? What if I could help other people make sure no family member lived with the same void with which I’ve lived for so many years?

And that’s when Skypod was birthed. I thought if I could help people send pictures, videos, and messages to loved ones that could help them as they navigated childhood and adulthood, I could help people fill the hole I’ve been unable to fill my whole life.

Can you share the most interesting story that happened to you since you began leading your company or organization?

The most interesting part of building Skypod occurred when the business took on a life of its own and started helping more categories of people than we ever dreamed of. Skypod started as a passion project to help people avoid feeling the same void I felt by not knowing my father.

We anticipated it would be well received by elderly parents, the terminally ill, or people in high-risk professions because people in each of those categories think regularly about a future without them. So we celebrated when these categories of people started creating digital time capsules for their families.

But the most interesting part of growing Skypod was watching it help categories of people far beyond our imagination. Being a technology company, we knew digital media gave us a lot of good opportunities to reach people. We had promoted it to the categories of people we believed would be receptive to it, such as people receiving services through a hospice organization, people who were putting their affairs in order, and the elderly in general.

We did not expect the volume of first responders, military personnel, and others who wanted to create digital time capsules. The loving anticipation of knowing a family member recorded something for you to open up weeks, months, or even years later made recording messages in Skypod a lasting act of love.

We had anticipated Skypod digital time capsules would be created in one direction — from the elderly to the young, the high-risk to their families, or from the terminally ill to their surviving loved ones. We were very pleasantly surprised at how many families were sending them in both directions.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Unfortunately, my best lessons have tended to come from my most embarrassing failures. And the best lesson I’ve learned in business came from a big, dumb, and, yes, funny mistake I made early on in business.

I was in my twenties and had just started making decent money from a software company that aggregated content and distributed it to hundreds of websites. It was working well and serving a lot of sites that needed quality content. In my mind, I thought I had built the next Google.

My landlord at the time was a very successful guy. We had spoken about my business, and he was always supportive. One day, I asked him to introduce me to friends of his who were involved in raising money for software companies. To my excitement, he agreed to set up a meeting for me with some investment firms, one of which was Bain Capital. (I had no idea who they were at the time.)

Had I gone to an Ivy League school — or any university for that matter — I likely would have approached things differently. But because of my public housing and military background, I had developed my entire vision of what these types of meetings involved entirely from movies and the internet.

I knew my product. I was passionate about it. And I knew the problem it could solve for many websites. But that’s about it. I assumed my knowledge and passion for my product would be all I needed to leave the meeting with a big check.

Boy was I wrong. I showed up to the meeting embarrassingly underprepared. I had no business plan and couldn’t answer most of their questions. All I could talk about was what our product did. I could only talk about me, my product, and my company.

I can only imagine what they were thinking during that meeting. They controlled millions of dollars and were actively looking to deploy that capital. In walks a guy introduced to them by a friend, and he had a product that could help a lot of people. It had all the ingredients for a successful meeting.

And then I blew it. Needless to say, I walked out of that meeting without a check; however, the lessons I learned from blowing that meeting have paid off tremendously in the long term. As I licked my wounds, I realized I blew the meeting long before I ever walked into the room by basing my entire pitch around my product, my company, and what I could do with their investment. Instead, I should have thought more about them, what they were concerned with, and how investing in me and my company could create mutually beneficial results.

I learned many lessons that day, but perhaps the most important one was about value. We must understand what is important to the other people around the table and demonstrate that value to them before asking for anything in return.

With Skypod, for example, our entire business is based on maximizing the value our users and their loved ones receive from creating digital time capsules for each other. Our entire team is focused on maximizing the user experience in a way that makes them want to create time capsules for even more loved ones.

From a financial perspective, we know that our ability to serve more people depends on our working from a solid financial model. This way, we can continue to support our users and additional users in the future. Our entire model is based on lasting stability for the company to allow users to create lasting legacies for their families.

Can you describe how you or your organization is making a significant social impact?

Skypod’s entire business is based on social impact. It is the core of what we do. In our case, we do it in two ways: with the core functionality of our product, and through company initiatives, such as how we dedicated 3 Million dollars in Skypod credits to help Covid-19 patients and first responders.

Regarding the core functionality of our product itself, our digital time capsules help people build deeper, longer-lasting connections with loved ones.

Recipients feel more loved even if they can no longer be with the sender. Skypod recipients look forward to opening their messages. They can see them in their inbox each with a special and unique “open date.” They can see a list of five, ten, or even dozens of messages and the date when they can access each one. This brings hope and excitement to many. So many of us have lost someone and think how special it would be to have just one more conversation with them. With Skypod, they can receive new messages of love, bits of advice, or anything else the sender chooses.

Senders get to tell their stories their way, and on their terms, to loved ones. They can be a part of every holiday, birthday, or special event, even if they can’t physically be there. They do this by setting the dates and times their messages can be accessed by the recipient, up to five years in the future. This allows them to send age-appropriate messages and set them to be opened when a child hits a certain age. Giving senders tremendous peace of mind that they can make an impact on people they care about months or even years into the future.

Additionally, as a company, Skypod is committed to using our product to support the people who support others, especially during trying times. That’s why we launched what we call the Skypod Challenge to spread the word about the 3 Million dollars in Skypod credits we’ve dedicated to frontline workers, first responders, and patients with Covid-19.

Can you tell us a story about a particular individual who was impacted or helped by your cause?

One of the best things about Skypod is that our entire business is about impact. That makes every user’s story unique and inspirational. One Skypod user whose story always inspires me is a 91-year-old woman named Shirley. Shirley documented her life story by collecting old photos, documents, and audio, which she plans to share with her grandchildren.

Imagine being Shirley’s grandchild knowing you get to hear her life story in her words, her voice. How special would it be for you to know your grandmother cared so much about you that she wanted to share photos, documents, and audio detailing her life with you so you always had that connection to her and your past?

Shirley’s story reminds me of something I saw on TV several years ago that has had a major impact on my life. In 2016, Anderson Cooper and his mother, Gloria Vanderbilt, were on CBS News discussing the release of their memoir, The Rainbow Comes and Goes.

Anderson’s dad died when he was just 10 years old. On the show, Anderson shared that he clung to the fantasy that one day he’d discover a surprise letter from his father that, in his words, “would show up one day, telling me all the things I didn’t know about him and all the things he wanted for my life.” “Of course,” he continued, “there was no letter.” Just like with my dad and me.

But there will be for Shirley’s grandchildren because she created digital time capsules with Skypod.

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

Unfortunately, the inability to communicate beyond the grave is the root of the problem Skypod solves. There’s nothing that can fix death.

But there are things we can do to address some of the things Skypod helps resolve.

First, we can build the strongest relationships we can while we are here. We can tell our family members we love them while we are here. We can share words of advice, love, and support. While we are here, we can let them know they are special.

Second, we can send messages of hope, advice, and inspiration to our loved ones, like Shirley did for her grandchildren. Take it from a guy who has lived four decades with a void left from a dad I never knew: even a single message from a lost loved one could have a big impact on the life of someone you love.

Third, you could encourage others to do the same. If you’re talking with a friend, encourage them to build stronger relationships with their loved ones. Inspire them to take action and share words of advice, love, and support with the people who matter most to them. And if they want to make a longer-lasting impact, tell them about Skypod and Shirley’s story, tell them my story, and encourage them that they can do the same.

Your words don’t need to be complicated or quoteworthy. Simple expressions of words of love or lessons from your life experiences can go a long way and lead to a better society today and in the future.

How do you define “leadership”? Can you explain what you mean or give an example?

I’ve always kept it simple when it comes to leadership and viewed leadership as the willingness to fully commit and put your heart and soul into moving an entire team toward a common goal.

The best leaders are fully committed to an important goal. And they know the best way to achieve it is to surround themselves with people who share that goal and help each person contribute to achieving it together. They know they can achieve more as a team than they can as an individual.

Leadership is not about inspirational speeches, flashy rewards, or motivating posters. And you don’t need to be outgoing, bold, or charismatic. You don’t need a fancy degree or certification. Anyone who is willing to put their full heart and soul into leading a team toward a common goal can be a leader.

For years, I let my humble upbringing and lack of advanced degrees make me question my ability to “be a leader.” I don’t have an MBA or a PhD. But while I lacked all the things you’d expect to see on the resume of a corporate CEO, I made up for it by being passionate about Skypod and surrounding myself with partners and team members who share my passion for helping people share comforting messages to loved ones through digital time capsules. I then work hard to empower them to work together.

That last part is hard. I’ve made many mistakes along the way. But all the best leaders do. The key is to learn from those mistakes and avoid making the same mistakes over and over again.

My partners and I at Skypod have worked hard to ensure the value of our team’s work is greater than the sum of each individual’s contribution. Because of that, the company, our team members, and the people whose lives we touch all benefit.

What are your “five things I wish someone told me when I first started” and why? Please share a story or example for each.

You’re good enough.

I spent too many years thinking I wasn’t good enough to succeed in business. That false belief about myself came from many places. People told me, “They will never accept you” and “You don’t understand how business works.” Even as I found success, comments like those lingered in my head and made me second-guess myself.

Imagine if those same people told me I was good enough. Imagine if those people told me I could build a business that made a difference in the world. What thoughts would have lingered in my head instead of second-guessing myself? Maybe I would have helped a lot more people.

And the truth is, I was good enough. If you’re reading this, I know you are, too, because you’re willing to invest in good “brain food.” So, let me be the first one to tell you: you’re good enough.

Avoid the naysayers.

Naysayers are everywhere, and they love to keep good people down. They’re in our families. They’re our friends. And they’re our coworkers.

You know you’re with a naysayer because they will tell you why nothing will work. Have an idea for a product? They’ll tell you ten reasons it won’t work. Want to improve your career? They’ll tell you why it’s a bad idea.

The worst part about naysayers is they think they’re doing you a favor by helping you avoid challenges. But the truth is naysayers often project what they believe about themselves onto you. They believe they can’t improve their life, so they tell you that you can’t improve yours either.

If you listen to them, your dreams will die inside you. Avoid them. And if you can’t, don’t let their negativity stop you. Instead, fully dissect your idea, look for obstacles along the way, make a plan, and take small, smart steps forward.

It’s not about the money.

Many young business owners make two mistakes when it comes to money. First, they try to build the business that will make them the most money. Second, they try too hard to pinch pennies as they grow. Both of those mistakes can be very costly.

If you build the business that will make you the most money, you will make choices based on dollars not passion. I’ve learned the hard way that money isn’t an adequate motivator. Instead, build the business you’re most passionate about, then develop a profitable business plan for it. Your business will benefit greatly from it, and so will your heart and soul.

And trying too hard to pinch pennies ends up costing you a lot more in the long run. Invest in talent. Invest in quality. Surround yourself with the right people, not the cheapest people. Make the best investment that you can with the money you have available. And be willing to invest your own money to do so. If you do, others will be much more willing to invest in you, too.

Don’t run from your past.

I struggled with this for years, worrying that I’d be “exposed” as a fraud. What if people found out I came from poverty and was not highly educated? What if they learned about my past business mistakes and personal losses?

I promise you, nobody is perfect. But what happened in our past doesn’t determine the future. It just led you to where you are today. Your future will be determined by what you do today. So, embrace the past. Be thankful that it got you here. Then make a new plan — a better plan — and move forward to a brighter future.

The right time is right now.

If you wait for the right time to improve your life, you never will. The economy will never be perfect. You’ll never have enough in savings. You’ll never have the right experience. The list goes on.

There are thousands of reasons to push your dreams aside and wait for “the right time.” But if you’ve done your due diligence and are passionate about making your dream a reality, roll up your sleeves and get started. You can figure out the details as you go. The right time to start is right now.

Be bold and unafraid to ask for help.

You’d be surprised how many successful people are willing to give free advice. Free help. All you need to do is be bold and ask.

And, yes, this was a sixth thing I wish someone told me when I got started. The seventh thing I would have listed was to not be afraid to be different — such as listing six pieces of advice in response to a request for five . . .

You are a person of enormous influence. If you could inspire 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. 🙂

The movement I would inspire would be one where people all around the world shared encouragement, advice, and wisdom with loved ones throughout their lives and beyond the grave. I’d make it so nobody had to live with the same void that I have without words or pictures from my father.

And that’s exactly why we created the Skypod Challenge and dedicated 3 Million dollars in Skypod credits for first responders and patients with Covid-19. These free credits are helping up to 30,000 families create digital time capsules for their loved ones.

So, I would encourage everyone reading this to participate in the Skypod Challenge. Please share a photo on social media of someone you’ve lost and wish you could hear from today. Add the hashtags #SkypodChallenge and #SkypodTogether to your post. Then nominate three people to do the same. Finally, post the message below to let others know about the challenge:

By honoring our lost loved ones in this way, we are sharing an important piece of our lives, thoughts, and hearts. This allows others to learn from our experiences. The Skypod Challenge is meant to create awareness and spread the word to our first responders including police, doctors, nurses, healthcare workers and their patients — that Skypod has dedicated 3 Million dollars in Skypod credits to help up to 30,000 families create digital time capsules for their loved ones. Each new account is being given 100 dollars in free credits which is enough to create and share multiple digital memories and messages with their loved ones. More details at

Together, we can impact millions of people’s lives for the better and replace the negativity that plagues many timelines on social media with messages of love and hope.

Can you please give us your favorite “life lesson quote”? Can you share how that was relevant to you in your life?

“The people who are crazy enough to think they can change the world are the ones who do.” — Steve Jobs

This quote by Steve Jobs encourages me to never be afraid of trying new things and continues to help me push forward with Skypod.

Skypod created an entirely new industry. In business, many people would tell you that trying to create an entire new industry is “crazy.” You need to educate people on what you do and why it’s important. You have no “best practices” to learn from others in the industry. You have no “industry experts” to lean on for advice.

Additionally, giving away 3 Million dollars in Skypod credits would be considered crazy by many people. But we know it’s the right thing to do because these important groups of people have been separated from their families to protect us and avoid getting other people sick.

I spent my whole childhood wishing for a “normal life” out of public housing. And I spent a lot of my adult life desperately trying to fit in regarding the world of business. Neither of those efforts led to me achieving much of anything.

This quote by Steve Jobs inspires me to not only accept that I’m a bit crazy, but to embrace it. Maybe the crazy idea of starting a new industry and then giving away 3 Million dollars worth of Skypod’s credits to the people who need it most is just crazy enough to change the world.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

This one’s easy. Oprah.

I love her “give give give” way to “live live live.” She’s not only influential but genuine. And she’s overcome tremendous hardships throughout her life and has been underestimated countless times. Yet she persevered.

To this day, she still focusses on helping people and has remained authentic and true to herself despite her tremendous success.

How can our readers follow you on social media?

Connect with me on LinkedIn. And follow Skypod on Facebook, Instagram, LinkedIn, YouTube, and Twitter.

This was very meaningful, thank you so much. We wish you only continued success on your great work!

Thank you!

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