Mark Switaj on Overcoming the Fear of Failure, and Growing as a Startup CEO

5 min readSep 12, 2018


Mark Switaj is the founder and CEO of RoundTrip, where he and his team provide on-demand medical transportation, and where he learned to turn his fear of failure from an obstacle to a constant source of insight and growth.

What sparked the idea for your company?
I worked in the medical transportation space first as an EMT. I worked in an ambulance so I saw firsthand from the transport side what the problem was. I’ve had family members that are personally affected. There isn’t a conversation that I don’t walk into where somebody isn’t telling me about a transportation issue for an aging parent, for a loved one, or for a patient that they’re taking care of. Knowing that we’re solving a real problem is what motivates me every day. That’s what got me into the space.

Did you have any fears in founding RoundTrip?
Especially in the very beginning. I’m not a serial entrepreneur so this was my first rodeo in terms of starting a business. My fear was that we’d fail. Failure is a fear. There’s so many people who have said to me, “Failure is something that you need to embrace. Take it from a fear and make it as a positive.” So we fail all the time. We learn from it then we move on

But there are days every day where I get up and I’m like, “I’m not sure we’re going to make it.” It’s an unrealistic fear. And I think we are going to celebrate our wins more and more often.

That is the biggest piece of advice that I try and absorb, and that is we don’t celebrate 90 percent of our wins but we seem to focus on the 10 percent we lose or the 10 percent we fail. And that’s something that I encourage every entrepreneur to do is to celebrate your wins. Learn from your failures but celebrate your wins every day that you can.

What has been your greatest struggle?
Initially it was rejection. Rejection is never easy for anyone, right? You have to have a thick skin as an entrepreneur. Everybody’s got a critique of what you’re doing. Everybody says that somebody else can do what you’re doing better, faster, cheaper. We’re no different. We’ve got a lot of people that are quick to say we can’t do what we’re doing. And they may be right. There may be things we need to evolve.

What has been your greatest triumph in your founder’s journey thus far?
The people who we have on our team. It is not signing another account or a contract.

I remember one Friday, clear as day, having someone we offered a job give us a rejection. It was a massive blow. And it was just luck that I think we reposted, and I’ll never forget when [my co-worker] Lindsay turned to me and she goes, “[The new person] is better than the person we initially made the offer to.”

It’s funny how life works out. Things work out for a reason, and I do believe that. There’s a time you get rejected and you get rejected for a reason. You learn from it. And there’s a time when you don’t.

What has been your biggest sacrifice?
I work a lot, so I sacrifice personal time. I’ve sacrificed money. But it is a sacrifice? Sacrifice, what does that mean? To give up something, in a way? I go to the religious context. So like when you sacrifice food during fasting, you learn a lot.

Not to get philosophical, but I’ve sacrificed money and as a result I’ve had to do things with less money that has generated experiences that have made me a better person. So like, when I go to New York I take the Chinatown bus. And maybe before I would have taken Amtrak or whatever. But I’ll be taking the Chinatown bus, and I’ll be laughing the whole way, ’cause like this is the most ridiculous experience of my life. But I do it all the time. I love it. If I had stayed with my last position and maybe made more money, I’d be sacrificing a level of joy. I have much more joy in what we’re doing now than what I ever did before.

Did anyone in your life try to dissuade you from becoming an entrepreneur?
I got rejected on the investors front. When I was trying to raise money, I had investors look at me and say, “I don’t think your business model make sense.”

In terms of dissuading me, just the opposite. That’s where I saw the American spirit come through. When I was telling people that I was going to be making that jump and trying to start a business, the reception from people was, “Go for it. Just do it.”

And they didn’t really understand what I was even talking about or what I wanted to do, but they would say, “Oh, I had an idea back when and I never did it. Absolutely, you should do it.”

Did you ever come close to giving up?
The third day. I’d gone home and bawled my eyes out. In the very beginning it was just me. I was trying to take an idea and meet with a software developer, and I knew nothing about software development. I had never done this before and I was being taken advantage of. I felt helpless.

At that moment, I called [my friend] Rohit and I said, “I can’t do this anymore.” And he’s like, “Give me 20 minutes.” And Ro works in banking. He does not work in startups. He doesn’t understand this space. He called his network, and from there it just started.

I panic that we raised $2 million. I panic because over half of that came from people I directly know or have known a good portion of my life. So there’s nothing like being reminded at a social event that I owe them a million and a half dollars. Oh, and plus they want a lot of return on their money. No, but they’re very encouraging.

What lessons have you learned as an entrepreneur?
People hang on every word you say. That’s something that I had a former boss tell me that I am constantly reminded of. It’s the nature of the role. People will say things that I have said, and that reminds me that I have to be very careful of what I say even when I’m exhausted or whatever. If there’s any sense of doubt from me, people in company will have doubt.

People think you make a lot of money, which is not the case. At least not in my case. That’s not easy, but the grass is greener. A lot of people think, “Oh gosh, I wish I had done what you did and left my corporate job and became a startup CEO.”

Life is hard regardless of what position or role you’re in, whether you’re a nurse, a doctor, a Lyft driver, CEO, work in marketing, or do what you do. It’s hard. Everybody has their own struggles.

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