Jerry Skillett of SPACES: “People always underestimate how difficult it’s going to be”

The main factors that distinguish successful startups from unsuccessful ones are conviction and commitment. The highly successful startups are ones who put their own resources at risk. I’ve put it all on the line 8 or 9 times in my career. They weren’t all successful but even the failures led me to another piece of […]

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The main factors that distinguish successful startups from unsuccessful ones are conviction and commitment. The highly successful startups are ones who put their own resources at risk. I’ve put it all on the line 8 or 9 times in my career. They weren’t all successful but even the failures led me to another piece of knowledge for the next venture that I could harvest into something even bigger.


Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and even bigger obstacles.

Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup.

I had the pleasure of interviewing Jerry Skillett, Executive Chairman and Co-Founder of SPACES, a revolutionary technology services company that enables parking facilities to serve as innovative commercial transportation centers. With more than 35 years of experience as an industry executive and innovator, Skillett provides SPACES with strategic guidance and visionary leadership. His business expertise extends well beyond parking. He was Founder and CEO of M/One, which launched multiple award-winning technology companies including SmartSound, Vicious Fishes Software, DVC Direct and 24–7 Digital, as well as product companies Stopain and Highlander Direct.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I grew up in the small town of Le Roy, Kansas with a population of 625. The furthest thing from my mind at the time was parking. I had no idea that even existed because when you live on a farm, you’re not really concerned about parking. Having a small-town experience and then going into a city benefitted me because you have a natural curiosity to all the things you’ve never been exposed to. So, that curiosity has always served me well.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

The aha moment that led to our current company came when I purchased Lanier Parking, which is the first company we bought under the Citizens Parking Corporation. When we went to look at all the locations in Atlanta, the General Manager who showed us around had set up the locations on Waze by dropping pins at all the locations. He navigated to each one through the app and when I asked him if he knew how to get to the locations without Waze or Google Maps he chuckled and simply said “No, I don’t.” That triggered my curiosity. I grew up in a generation of not only using physical maps but generally knowing your directions. You had a natural idea of where things were but now it was clear that had changed. Now everyone was navigating to their destinations utilizing their mobile phones. They didn’t even attempt to find the locations without it. It was a clear behavior had changed. Which was the aha moment for me.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

My father was an innovator, in his own way. He was from a very poor family and he happened to be an incredible athlete. With his own father having passed away due to injuries sustained in WWII, the teachers in his high school surrounded and mentored him primarily because they wanted him to stay eligible to play sports. This created a deep respect for the teaching profession. He eventually was able to attend college and would go on to become a teacher, then a principal, then a superintendent, then a professor and finally the Dean of Education at a major university. His whole life surrounded education. Which is even more incredible considering no other family member had even completed high school and he ended up with a doctorate degree. He was a living example of how anything was possible and he passed that onto me and my siblings. My two younger sisters and I have all been successful and led astonishing lives and we know it all comes from him instilling this sense of possibility in us.

What do you think makes your company stand out? Can you share a story?

The biggest thing that makes SPACES stand out is that we simplified a very complicated process. You can now park, pay and exit any gated parking facility by simply dialing a mobile number. The platform enables parking companies to offer their customers a simple, nationwide parking solution, while unlocking substantial financial value from their user bases. This creates new avenues of monetization for channel partners and parking facility owners and operators, and at the same time provides a superior consumer experience. We have simplified the parking experience anywhere in the world.

How have you used your success to bring goodness to the world?

The biggest thing that we do to bring goodness into the world is with a group called Avail in New York. It is a deeply personal for me because I’m the product of an unexpected pregnancy to two unmarried teenagers. Thankfully my grandparents were so phenomenal about the situation. My grandparents believed a birth was abundance and being a farmer, a birth of crops, cattle, horses, everything meant abundance. With a child this also meant another worker on the farm. My grandparents surrounded my parents with love and encouragement. They were thrilled for the family to be expanding and it changed the trajectory of my life, as well as my parent’s lives. My mother has two Master’s Degrees and my father has a Doctorate Degree. They never missed a beat, what could have been a negative turned into a launching pad for an outstanding life. Avail is all about helping individuals navigate unplanned pregnancies and surrounding these young men and women with unconditional love no matter their choice. It is deeply personal to me having been the product of such a situation and finding that unconditional love made all the difference.

You are a successful business leader. Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Honesty, integrity in what you’re doing and love. There isn’t a person in this world that I hate. I’ve had a lot of enemies, but I don’t have hate in my heart. Those three things are huge and they’re traits that when I hire people, if they don’t have them, they are probably not going to work out no matter how great they are because those traits are hard to teach later in life. We view ourselves as having a god given talent for parking. With that in mind, we try to help the parking company or garage owner make more money, with a high expectation that we can help them be successful. We give first before we get and concentrate on putting ourselves in situations where we can help.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I’ve started a lot of companies, but any time I started one to make a lot of money it never turned out well. When I started a company based on the passion I felt, then I made a lot of money. Everyone around me would tell me it’s a great idea and I would make a lot of money, but really any time I followed my passion is when the money actually followed.

Can you tell us a story about the hard times that you faced when you first started your journey?

At the beginning you feel under resourced. As I’ve done this journey for many years as an entrepreneur, I find that you’re really not stretching unless you’re “dangling off the edge of god.” I like to put myself into situations that are basically impossible. That’s when I know I’m in the right place. It’s a very difficult position to be in but you’re not reaching your full potential as a business unless you do that. Over the course of my career, I have found myself in that situation 8 or 9 times and always found success overcoming it.

Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

I learned perseverance through mountain climbing. I’ve climbed some of the tallest mountains in the world. Some that would take 3 or 4 weeks to summit. The thing that you learn is that at the beginning you can see the summit and even though it seems a long way away, you can still see it. But once you get on the mountain you can’t see the summit. It can be very discouraging when you no longer can see the end result. So, most people (90%) quit on that journey because they lose the vision of what it would be like to be on top. It’s more difficult than you planned, the food is terrible, you’re sick to your stomach, the weather is bad, but you learn to focus one step at a time. You realize that you’re making progress and you will find yourself on the top after 3 weeks of hard work. You got there by persevering one step at a time blocking out all of the other things. The summit is amazing, and the journey is extraordinary, and business is the same way. I’ve never met anyone who jumped peak to peak. They always summit, go back down to the valley, and then do their next climb. The process repeats over and over, and you get stronger, can get higher, and handle more difficulties because you’ve trained yourself to do it. The technique is taking one day at a time, making progress every day. Over 4 or 5 years, you’ve been able to do the impossible.

The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

I’ve learned to have incredible joy in being really uncomfortable. The more uncomfortable, the happier I am. I’ve traded a negative so instead of ‘this,’ I’m going to feel ‘this’ instead. That mindset is exciting because the moment that you train yourself in that manner, you are prepared so that every set back and failure is leading you to the celebrations, thrills, and joys of success. They go hand in hand. Once you understand that and see the challenges, you want them to be major. You want this because you realize the outcome is equal to the challenge.

Let’s imagine that a young founder comes to you and asks your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

Bootstrapping at the beginning is always the best choice. What you’re doing is building conviction. To be successful as a founder you have to have conviction. Once you have it and have proven the product with a pathway to profitability, you are able to eliminate the questions that you started with. Then you raise the money for your venture. This is critical. I see many people who’ve raised the money but don’t have the conviction because they have plenty of money to experiment. But you want to eliminate as many risks as possible before you raise the money. The money will always be there. Conviction is the real key to success. If you put everything on the line in the beginning, you’ll find the solutions.

Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”? If you can, please share a story or an example for each.

The main factors that distinguish successful startups from unsuccessful ones are conviction and commitment. The highly successful startups are ones who put their own resources at risk. I’ve put it all on the line 8 or 9 times in my career. They weren’t all successful but even the failures led me to another piece of knowledge for the next venture that I could harvest into something even bigger. But I didn’t lose other people’s money. I lost all my own first. I was always all in. That is the biggest thing. I don’t see a lot of people who are willing to do that. The older they get the less risk they take which doesn’t make sense to me because they have more knowledge and should put it to work. When combining those two things together you receive remarkable outcomes. You have to be willing to take the risk though.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

People always underestimate how difficult it’s going to be. I build three failures into the process and I build in twice as much time as I originally expect. That expectation is a mindset so when you do have your first failure in the journey you easily except it and tell yourself it’s no problem. You still have two more to go. Then the second failure, or you change the plan, but you still expect it. The third failure always makes me really excited because it means the answer is just around the corner. So, I build in these failures. The fact is that those failures require resources. I plan for that too. The biggest mistakes are when people don’t build in time and resources for failures. They utilize all their assets just to get to the first failure, they fail, and they have nothing left to help them keep going from there, so they fold up shop without ever getting the opportunity to harvest the experience of each one of those failures to get to that final answer. No one ever gets it right at the beginning. No ones that smart.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

It took me 12 years to qualify for the Iron Man World Championship in Hawaii. During those 12 years, I was running my own companies. What it taught me was that you need the same level of disciple necessary to become a world champion Iron Man as you do to run your business. It’s possible to raise a son, have a great marriage, be a great athlete, and run a business while being active in your community. It may seem impossible, but it’s not because it’s all about discipline. The discipline of training leads to a discipline in business, marriage, fatherhood, and everything. If you’re cheating on any of that, then you’re not fulfilling all that you can be in those areas. I think it’s critical. I have always remained disciplined when it comes to finding time to exercise. My workouts have been the mental health aspect of being able to deal with the rest of it. If you’re not in good health and good shape, it’s difficult to take on all the other things stress wise and still have enough energy to do it all. You can’t cheat on that.

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. 🙂

There are actually two things that I would focus on to bring the most amount of good to others. The first is to treat other people how you would like to be treated no matter what. There are amazing things that happen when you treat people with respect, and I think there is a real lack of that at the moment. There is a lot of selfishness out there and changing that would be incredible. The second would be focus on the idea to give and it will be given unto you. While both of these are based on biblical principles, the fact of it is, if you give first, it’s just the way the world works. Not only do you get what you give, you get it back overflowing. And that’s addictive because giving and having a heart for giving in every circumstance is an astonishing life to live particularly in business where everyone is always acting like they will not give an idea first or help someone first. But if you are able to step up and do that without knowing what you’re going to get in return, the results are always overwhelming because you get back an overabundance.

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

While unfortunately he won’ t be reading this but if there was someone in history that I would like to have breakfast or lunch with, it would be John D Rockefeller. Not because he was probably the wealthiest man ever, at one point he did have about 3% of the GNP of the United States. But he was a very disciplined and principled person. He led an amazing life well above his upbringing. After he became the wealthiest man in the world, he tried to give it all away. All these years later, his family is still giving and it’s seemingly impossible for him to give away everything, but they continue to try. His perseverance, discipline and business principles would make it an amazing lunch because I certainly would have a lot of questions.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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