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  • Writer's pictureYaakov Citron

Flying With Sim Shain: The Business of Transporting You Where You Need To Be

Updated: Jan 18

Welcome to another edition of Solo2CEO. Our guest today is a paramedic who has been in the business of flying patients and organs for more than a decade. Let’s meet Sim Shain.

Sim Shain, tell me what you do.

I am a paramedic, and I do private and corporate aviation for medical, business, and corporate travelers.

What is Paraflight?

Paraflight is an aviation company that specializes in medical transports, corporate executive transports, organ transports, urgent transports, and anything where you can utilize aviation. 

Paraflight is strictly brokerage, called Asset Light. As a technology company, we built special apps that are able to communicate with operators all around the country and the world.

When was the beginning of Paraflight? What inspired you to establish this company? 

Paraflight started as an air ambulance company in 2014. We did air ambulance, flew medical teams and patients everywhere, and had an opportunity to get into organ flights. What we actually did was to provide the aircraft for hospitals. In that way, we were able to save lives.

I had a close relationship with my mentor, Steve Zakheim, who passed away in 2013. He owned an aircraft that he used to send patients wherever. He used it for kindness and charity work to be able to help people.

I have been flying with him since 2008. After his exposure on 9/11, he got sick. He called me into his hospital room and told me to take his jet and go change the world. I didn't take his jet because it was very overwhelming for me after he passed away and it's also very expensive to maintain. 

I told his family to sell the jet and I'll figure something out. I had wanted to open up an air ambulance company, and include the charity component of giving back. 

Steve taught me that it is very easy to say no when somebody needs help because you can say no and move on. But you should always be able to say yes, which is much harder. If it's difficult, do it; and if it's impossible, try harder. That was how he lived his life, and I try to live with that as well. 

What assets do you have for Paraflight?

We have our ground transport, our staff, and our technology. We do not deal with aircraft payments, pilots, and maintenance. We just get the job done, and we pay for other people to handle the large assets for us.

None of the planes have the Paraflight logo or sticker on them, but a few cars have them. We use these mostly for organ trips, medical trips, and some crew trips. We usually carry organ boxes or organ transplant teams. We take surgical teams to airports for their flight, and pick them up after a couple of hours.

Some trips are short and do not require a jet or a helicopter. We just use land vehicles to take a medical team or to carry organs. 

How many people do you have at Paraflight?

We are a group of about 60 people, full-time and per diem. Mostly we are based in the East Coast, but we have a West Coast division that stays up later at night. We have a team in Los Angeles.

The majority of our employees are drivers, paramedics, nurses, physicians, and flight coordinators. The bulk of the work falls on our ten flight coordinators, who work during the week, weekends, and night shifts. Likewise, the majority of our drivers and paramedics are per diem.

Most of our work involves coordination. With Asset Light, I believe that scaling with technology makes it much easier and more cost-effective for us.

Does each of these jobs cost more?

More or less, because there are many operators who don’t make money. Management companies make money. Aircraft operators and owners do not necessarily make money. Many of the operators do not make money because they have to deal with maintenance issues, mechanical issues, and routing aircraft. 

For our business model to scale across the country and across the world, we need technology, like Uber. Uber is the largest taxi company in the world, yet it doesn’t own even a single taxi. So we became the Uber for flights.

Tell me about this flight app you developed for your company. 

We built an Uber-type app for the organ flights division which gives us the ability to reach out to more than 80 operators representing a few hundred aircraft. 

We just launched another app, Urgent Flights, because we recognized that emergencies also happen outside of medical matters, such as family or business emergencies. We built this Urgent Flights app with the same technology used to build the Organ Flights app to respond within a short period of time. 

How does your app work?

It works in two ways. 

One is when somebody needs to get somewhere quickly for various reasons. Once he contacts us, we will post in our app to let our member-operators make quotations. We’ll select the most reliable and most responsible quotations and present them for the client to decide.

The other one is through operators who are signed up for our app. The client can send a request that he is within the vicinity and can take the trip. Sometimes these operators have a mechanical issue, so they go within the app itself and make the inquiry and booking for the client.

What are the key differences between Paraflight and Urgent flight?

Paraflight arranges for medical corporate organ flights. We have people who book Paraflight, typically anywhere between a couple of weeks and maybe a month or two. Booking slots within a considerable time in advance is needed especially on dates near holidays or big events. 

Urgent Flights is a division of Paraflight. We arrange our flights when we need to fly as soon as possible. Whenever someone needs urgent flights, they can book through the app.

We do not charge an additional markup for urgent flights. We recognize an emergency and they get the same price as the advance booking. 

Why would people book flights in advance?

Booking flights in advance will make them get the aircraft of their choice, making them not dependent on what is readily available. It's that level of comfort knowing that they’re much better off booking in advance because you have a much larger pool of availability. 

When you are booking because of urgent matters, you are limited by what is available or what can get here right now. And there's a possibility that you're going to pay more because now you just need a one-way trip as opposed to a round trip.

Depending on how the aircraft is set up, you might have to pay more because the aircraft would need to reposition. Is this correct? 

Yes. Sometimes they have to reposition. If you set that up a month in advance, the operator has to figure out how to position themselves. However, if you have to go to a different airport because of a canceled flight, and you have no aircraft available, you need to pay a repositioning charge to get an aircraft for that flight.

Can clients choose what is on the menu? 

On a regular flight, they can pick anything they want. But on organ flights, it depends on the time of day. With our attention to details, we keep track of what our client likes and dislikes. 

It is important to give clients a better flight experience. The key is to listen and remember to listen. We ask them about any dietary restrictions, such as allergies to certain types of food. We want to make sure that we are taking care of them.

Did you have your own flying license?

I don't have a flying license. I really wanted to be a helicopter pilot, which is more dangerous, more complex, and more time needed to make it happen. I never dreamt of being a pilot, although one day, I would probably be one. Right now I am more focused on the growth and scaling of our business because I need to set the goal without compromising it. 

Do you have international operations for Paraflight and Urgent Flights? How much do these flights cost?

We have international operations, but we discourage doing it. Some people call us for our services, and we ask them to fly business class because it will cost them much more money. But then I realized that these people needed to get more time by using our services.

If you wanted to fly out of the closest airport from Lakewood to Miami, a one-way trip using the smallest aircraft to a round-trip on a heavy aircraft would cost about $20,000 to $60,000. The costs also depend on timing, holidays or big events, and aircraft repositioning. 

From the year you started your business in 2014, how did you scale your business?

It was just me in 2014. Though I have been flying for a number of years, I knew very little about aviation, and I did not know anything about charter flights. I had to learn about licensing, flying rules, taxes, and all the nuances.

I realized that it was too much work for me alone, so I built up a solid team of honest and ethical people who are great to work with. The most important thing is to develop a team of people who trust and believe in me. I needed to trust my personnel because our clients trusted us, too.

The first thing I look at in a worker is honesty, before looking at his experience. He needs to be able to work under pressure. Anything can go wrong with logistics, and you have to think quickly and look for various options. Not everything goes smoothly and you have to manage those details to make sure that we are ahead of the game for anything that can potentially go wrong.

How do you deal with pressure in the business?

It is definitely a lot less pressure. We have drivers, doctors, medics, and flight coordinators. People, 60 of them, work in shifts to make sure that everything is running smoothly. I check everything as soon as I land. I have a very solid team and they are tremendously trustworthy.


What was the most impactful hire that you made in the last 10 years?

Hiring my coordinators was the most impactful because each of them brings another value to their experience in aviation or organ transplant.  These people understand every aspect of aviation, cargo, and some luxury flights and aircraft brokerage. You pay a premium for hiring these people with extensive experience of at least five to ten years. Additionally, it would take at least two or more years to train someone to understand aviation and to work faster and efficiently in the field.

Your story about two approaches to hiring- “Batteries Not Included and Batteries Included” is very interesting. Can you tell me more about it?

“Batteries not included” refer to people you hire who are cheaper to train, and are loyal to you, while those “batteries included” are more expensive because they are experienced and are more likely to jump ship. Training an employee is a risk because there is a possibility that they might leave the company and become your competitor the next day.

To handle this situation, what we can do is to give these people a good work environment and to appreciate them. Whether they want to go or stay with you, you have to let that happen. 

Being a CEO or being an entrepreneur is not as easy as it looks. Some people don’t know the struggles that he went through to be the person he is today. 

Have you had people who helped you in the business?

I have a number of friends who helped me in the business. I have a close friend who gave me an insurance card when I needed to book a flight, other friends chipped in their money, helped me get a credit line, and endorsed me to a bank. A friend also hired a business coach for me.

Family and friends provided support and finances and helped me grow my business. 

What are some measures you are taking to ensure that your clients are happy?

We make sure that clients are able to close their eyes and know that everything is being taken care of for them. They can focus on their business and other essential matters and not worry about the jet, the ground transport, or food. 

We live by transparency and loyalty. Our business is very expensive, so we make sure that clients trust us with their money by presenting the best price we can offer. We thank every client after every trip and we appreciate them for using our service. We thank our vendors, too, for the service that they do for us. 

As a CEO, do you have to know every detail of your business?

It is very important to become an expert in your field. For me, I know how our computer systems, our technology, and our phone systems work. We have people to take care of our business, but if they are unavailable, I can step in and do that if I have to. 

It is a cliche when we say “You focus on your business and we’ll focus on your flights.” We will take care of it, so you don’t have to worry about your flight.

Did you start this company alone, or did you have partners?

I started on my own and had a partner for a while, but it did not work out. I felt it would be best to do it by myself. 

Some partnerships work and some do not. If you pick a partner, make sure that you can trust him with everything. You have to bring more to the table than just money. It is better to find a partner who is not like you. Find someone who you enjoy spending time with, somebody you're comfortable with, and somebody whom you trust. My weaknesses will play off his strengths and my strengths will play off his weaknesses. So this way everybody has a job that they know what to do.

What would you advise a beginner in business to choose between getting a loan as a single proprietor and a partnership where the other person provides the funding?

As someone who decided to go on his own, it would be better not to start with taking cash advances and getting so mired in debt. Understand the business and slowly grow organically. Try to get a mentor or a business coach who understands and has no personal interest in your endeavors.

Know what your vision is. Project where you will be within this span of time and be conservative about it.  Don't be aggressive. In the beginning, a lot of money can really bankrupt your entire business. Start off slowly because you make mistakes that can cost you a lot of money. 

Be very hesitant about taking a partner if you can do it on your own. But if you take a partner, there’s a possibility that you could be spending more time with them than your family or friends. You will have to trust each other with uncounted money. You need to have loyalty, transparency, and honesty. 

What are some of the challenges you encountered in the last ten years?

I started very lean and did not have many resources for my business operations. It took a lot of time to do my own accounting. Two years later, I hired a bookkeeper firm that cost me about $4,000 a month. They took care of everything: recovering lost money, going after a client for non-payment, sending extra payments, and other financial aspects of the business.

If you want to grow your small business, hire bookkeepers. Pay for insurance to ensure that you are protected. These things—insurance, and bookkeeping—keep your business in order.

How do you advertise or market Paraflight, and which do you think is the most effective?

In the beginning, I had no money for marketing. I used my phone to call people who know me to help me find clients. Confidentiality is important so we never disclose their identity and flight schedule.

Consequently, we hired marketing companies. We advertised through some news articles, podcasts, TV shows, newspapers, and articles about our charity work. Over the years we also utilized word-of-mouth.

We do some branding by jet magazines, although we seldom do it because it is very expensive. We also make use of social media marketing which is quicker and cheaper to reach the target market.

I believe the most effective form of advertising is social media and TV/radio spots. It is a big difference when people understand what we offer over social media marketing.

How do you put educational content or paid ads in your social media marketing? 

We use Instagram, Facebook, and LinkedIn. Interactions, writing, and posting articles are very helpful in making us somewhat of an expert in our field. We don’t use paid ads on social media. 

Do you use video for your marketing?

Yes, we've done it sometimes on trade shows. Video productions are expensive, but they absolutely go a long way. And compared to print-outs, they really get your message across. An engaging video is a way to send your message in a very short form - in less than a minute.

How do we get in touch with Paraflight or Urgentflights?

You can easily contact us through our websites:,, 

Additionally, you can follow our social media accounts on LinkedIn and Instagram. 

Our toll free number is 844 538 1911.

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