Ryan Sullivan – CEO and Co-Founder of ParkiFi

It is critical that we continue to learn from our customers, competitors, and the market as a whole if we are going to be the best at what we do.

As the CEO and Co-Founder of Parkifi, Ryan Sullivan works with companies to solve the world’s parking challenges. His core belief that we should know where available parking spaces are, in real time, and not spend 15 minutes or more driving around aimlessly looking for a parking spot is changing the way the world sees parking. From his consulting days at Accenture to his technical work at Microsoft and beyond, Mr. Sullivan has always been at the forefront of next generation technologies. Long before Ryan became an Agile Coach, he understood the role flexibility in customer-driven solutions, which has brought him to where he is today. Parkifi is Ryan’s second startup, where he unites clarity and technology to solve real life problems. His first startup, Teegwen, developed mobile applications in Objective-C and full feature web-based applications with the LAMP tech stack. As a Co-Founder of Parkifi, Ryan is at the forefront of finding ways to use technology to make our roads safer and to understand the real value of our parking spaces nationwide. Parkifi’s real time solutions are enabling smart cities in ways we never thought possible. Ryan holds a B.S. in Computer Science from Syracuse University.

Where did the idea for ParkiFi come from?

While I was running late to a meeting and frustrated searching for a parking spot with no luck, I asked myself, “Why isn’t there an easier way to find parking?” After looking into why this wasn’t already solved, I talked with my friend Rishi Malik and we decided that we would be the ones to remove this hassle from city life, so we founded ParkiFi.

What does your typical day look like and how do you make it productive?

I do not really have a typical day anymore. As CEO, I transition between manager, fundraiser, sales person, product manager, corporate strategist, etc. on an hourly basis. The only thing typical about my day is that I always go where I am needed the most at any given time. It is one of the things I love most about leading ParkiFi.

How do you bring ideas to life?

I rely on my team to take my big ideas, that are often times not grounded in reality yet, and turn them into something real. They are the ones that make my ideas happen, I just am the one dreaming up more things for them to solve.

What’s one trend that really excites you?

I am really excited about the increasing adoption of mobile phones as a central computing device for your life. Rather than relying on a car, or laptop, or desktop, we can build functionality into a phone and reach nearly everyone.

What is one habit of yours that makes you more productive as an entrepreneur?

I get extremely laser focused and committed to things once I dive in. This allows me to push through long days, weeks, and months without breaks, and I thrive on it. Normally this kind of endless day-to-day work would drain people of energy, but it energizes me more.

What was the worst job you ever had and what did you learn from it?

I have been incredibly fortunate and have not had a job that I truly hated. I have learned things I like and don’t like from every job, but they have all lead me to where I am today.

If you were to start again, what would you do differently?

I would make sure that we had a hardware expert as part of the ParkiFi founding team since we have a hardware product. In general I would make sure that the founding team had all the skills required to develop the first MVP version of our product.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I am constantly adding to my peer network of CEOs. I can not express how critical those relations are for me as I continue to grow the company and myself. Those peers help me talk through concerns and issues that are often unique to the CEO role and that are not easy to discuss with people inside the company. I would never be able to do this without that support group.

What is one strategy that has helped you grow your business? Please explain how.

At our core we are always questioning our ideas and assumptions. We never believe that our product or solution is perfect for the market. We are always keeping our eyes and ears open for more information to refine our products. It is critical that we continue to learn from our customers, competitors, and the market as a whole if we are going to be the best at what we do.

What is one failure you had as an entrepreneur, and how did you overcome it?

My biggest learning experience thus far and the hardest thing for me to do has been relinquishing control of every detail and no longer involving myself in every step. As an entrepreneur you start out having to do everything or you simply will never get off the ground. However, it is just as vital to rely on your team and let them do what they are hired to be great at. I’ve taken too long to learn to trust the amazing team I have and let them do their jobs without me always involved.

What is one business idea that you’re willing to give away to our readers?

Something I have been wanting to look at perusing is a way to fix the professional review and recommendation process. Currently we do annual, or more frequent, reviews with our managers. We ask for feedback to get advice on how we are doing in our jobs, how we can progress in our careers, and what our strengths and weaknesses are. However, when we leave a job that track record is left behind. We can’t offer a new potential employer that information to show them how we have grown and succeeded in our career, so we have to rely on letters of recommendation that are often hard to get because of legal concerns or because you choose to leave a job before your boss wants you to. I would love to see a system that can outlive your current job and follow you as a resume of your past growth and accomplishments that is verifiable by potential employers.

What is the best $100 you recently spent? What and why?

A battery pack case for my phone that lets it last all day while I travel. Game changer.

What software and web services do you use? What do you love about them?

We use Slack, Google Docs, Dropbox, etc. Basically if it is not built from the ground up to enable collaboration and sharing then I do not want to use it.

What is the one book that you recommend our community should read and why?

Good to Great, by Jim Collins, hands down.

What people have influenced your thinking and might be of interest to others?

I read Elon Musk’s biography in the early days of starting ParkiFi and his journey completely changed my view of successful entrepreneurs. We naturally assume, or at least I did, that the people we see as successful — Elon Musk, Mark Zuckerburg, Steve Jobs — had a path to success. To hear how hard those paths were and how many times they could have failed but didn’t, motivated me more than anything else has before. It gave me the courage to push through the doubt and always believe success is mine for the taking.


Ryan on Linkedin: https://www.linkedin.com/in/ryanparkifi

Ryan on Twitter: @rysulliv

ParkiFi on Twitter: @parkifi

Parkifi on Facebook: https://www.facebook.com/parkifi/