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Bill Herp of Linear Air: “Business and leisure travel will increasingly blend together”

The lines will continue to blur between traditional types of travel. Business and leisure travel will increasingly blend together. Airline business travel will come back, but many remote work situations created during the pandemic will become permanent. Travel and hospitality companies will play an important role in helping the post-pandemic workforce achieve work/life balance. As […]

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The lines will continue to blur between traditional types of travel. Business and leisure travel will increasingly blend together. Airline business travel will come back, but many remote work situations created during the pandemic will become permanent. Travel and hospitality companies will play an important role in helping the post-pandemic workforce achieve work/life balance.


As part of my series about “exciting developments in the travel industry over the next five years”, I had the pleasure of interviewing William Herp.

Bill started Linear Air to bring his understanding of the value of private aviation to more travelers like himself. He became a pilot in between startup ventures in the mid-nineties and came to understand the value of private charter as founder of eDialog, a pioneer in digital marketing with clients located far and wide. Linear Air makes it easy to book a charter aircraft online by providing access to the full range of options for a traveler’s itinerary, all priced and available for purchase seamlessly online.

Bill has been building and investing in technology-enabled startups and disrupting markets by utilizing direct and internet marketing since earning his MBA from Harvard Business School. Bill holds an FAA Airline Transport Pilot certificate and is a graduate of the University of Notre Dame.


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

It started with my participation in Junior Achievement in high school. That experience gave me a window into what it takes to start and run a company. I discovered that it was doable and thought, “why couldn’t I be an entrepreneur?” This helped me focus on what I wanted to study in college. I earned a business degree in Accounting from Notre Dame, figuring that accounting is the language of business and I wanted to be fluent. I then went on to receive an MBA from Harvard Business School and, from there, set my sights on becoming an entrepreneur focused on disrupting markets with new technology.

Can you share the most interesting story that happened to you since you started your career?

Many years ago, I co-founded a start-up that wasn’t getting a lot of initial interest from venture capital firms. My co-founder had a connection who was able to get us on the calendar of a Boston-based venture capitalist. Since this guy was basically meeting with us as a favor to someone else, we had to be at his office in the city at 7:30am before his real day began. As we were making our pitch, he literally fell asleep and spilled his coffee on his shirt. He then jumped up, ran out and never returned. After about 20 minutes, we realized it was time to leave as he was nowhere to be found and no one else was in the office yet. A few months later, that same venture capitalist gave us a term sheet after the industry sector we were in heated up and one of our competitors received funding. So, I guess the moral of the story is that you just never know what twists and turns your entrepreneurial journey may take so keep believing and working hard and good things will happen.

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?

I was invited to golf at an exclusive country club by the investment bankers who had recently taken public the company at which I was the chief financial officer. Everyone in the foursome was a member of the club, except for me. I was, and am still to this day, not much of a golfer. On the 10th tee, in front of the clubhouse, I took a huge divot out of the tee box with my driver while missing the ball entirely. On my second try, I sliced the ball so hard I think it went onto the adjacent tennis courts. What did I learn? I have realized over the years, through this experience and many others, that it’s important not to take the way you look (or think you look) to others too seriously. At the time, I was mortified. Now, 25 years later, I can look back on that experience and laugh at myself.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”? Can you share a story about that?

Try to remember your passion and remind yourself of the reasons why you first started doing what you are doing. Schedule time for self-care activities to keep yourself in shape and maintain good relationships. I have found daily meditation to be a great way to start my day in the right frame of mind.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My friend John Tipton, who I grew up with in Louisville, Kentucky. He was often my sounding board, patiently listening to me complain about the challenges and frustrations of getting my entrepreneurial engine started. One day John, who was in Boston attending Harvard Law School, suggested that I apply to Harvard Business School. In fact, not only did he suggest it, but he actually walked across the Charles River bridge from Boston to Cambridge and had them mail me an application. John is still a great friend and I am forever grateful that he pushed me to take a critical step in my development as an entrepreneur.

Thank you for that. Let’s jump to the core of our discussion. Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?

Linear Air is bringing unprecedented consumer access to private air charter travel. We’ve built the only platform in the industry that provides all available charter options for any flight in North America. Consumers can, for the first time, choose from more than 4000 aircraft operated by FAA-approved commercial charter operators to quickly and easily schedule their flight either directly through our website or via Kayak, SABRE Amadeus and Worldspan travel agents.

Which “pain point” are you trying to address by introducing this innovation?

There are several key points of pain that we address. The first is access. Historically, the process of booking a charter flight has not been easy or consumer-friendly. The booking process has been confusing and hard to navigate resulting in too much broker control and a lack of transparency with regards to flight options and pricing. By giving consumers access to all the possible options in a ‘click-to-buy’ online marketplace, we make the booking process easy and transparent. Consumers can now purchase a private charter flight with the same level of confidence they have when booking a flight on one of the large commercial carriers.

By making charter air travel an accessible option for a greater number of travelers, we are also alleviating many of the pain points associated with traditional air travel. We cater to you in ways that commercial air travel cannot. We do this by giving you the freedom to choose your personal flight schedule, the type of aircraft you’ll fly on, the passengers you’ll fly with, and which airports are most convenient for you. We deliver all the safety, service, comfort and convenience that makes flying fun again but with none of the hassles and unpredictability that are all too common with the large commercial flights. With easy parking and pilot escort for security, check-in, and boarding, you can arrive at the local airport of your choice just minutes before your flight. No expensive parking fees. No shuttles to your terminal. No long TSA lines. No missed flights. No stress. Just a better flying experience.

How do you envision that this might disrupt the status quo?

For travelers who already have experience using charter air travel, we’ve made the experience much easier, more transparent and less expensive. You no longer need to spend tens of thousands of dollars upfront to purchase a fractional share of an aircraft or pre-purchase a jet card to access charter travel. This is a real game-changer for anyone who knows how opaque, frustrating and expensive it can be to book a private charter flight.

For travelers new to charter, when they see the options they will be surprised at how affordable certain trips can be, especially those with a small group or family traveling together. By offering charter flights as a booking option in the online places where travelers are already searching for flights, we believe travelers will increasingly consider charter as a viable, and preferred alternative to flying commercial, especially during the COVD-19 era.

As you know, COVID19 changed the world as we know it. Can you share 5 examples of how travel and hospitality companies will be adjusting over the next five years to the new ways that consumers will prefer to travel?

  1. Enhanced travel safety and sanitation protocols are here to stay.
  2. Consumers will continue to demand more personalized travel experiences and more control over their travel options.
  3. The lines will continue to blur between traditional types of travel. Business and leisure travel will increasingly blend together. Airline business travel will come back, but many remote work situations created during the pandemic will become permanent. Travel and hospitality companies will play an important role in helping the post-pandemic workforce achieve work/life balance.
  4. Private charter travel will become better understood, and increasingly in demand, as an option to driving or flying on the big commercial airlines. Increased awareness and access will drive growth in charter operations.
  5. Technology advances will continue to improve aviation safety, increase consumer choice and drive down cost. Innovations such as electric aircraft and urban air mobility vehicles are not that far around the corner.

You are a “travel insider”. How would you describe your “perfect vacation experience”?

The perfect vacation for me involves cultural adventure. My wife and I really enjoy traveling to new places, meeting people who live there and taking in the sights and experiences. Because vacation time is so scarce and precious, I am always striving to improve the ‘fun time ratio’. Too often, so much time is spent on the logistics of vacationing such as traveling to and from the airport, standing in lines, waiting for flights, driving long distances from the airport to your destination. Maximizing the fun time is part of Linear Air’s mission. We offer a better way to fly that eliminates many of the time-consuming logistical activities that can consume far too much of our finite vacation time, especially if there are delays or cancellations. We’ve all heard the horror stories from people whose dream vacations were ruined due to flight delays, missed connections or cancellations. Using Linear Air to fly charter gives travelers the ability to have more control over their travel logistics so they can maximize the fun time. Time is our most valuable commodity in life. We recognize that and have built our business model around overall value. We’ll never be the lowest priced option but, I believe, we will always offer the highest value.

Can you share with our readers how have you used your success to bring goodness to the world?

As a serial entrepreneur, I am proud of the hundreds of jobs I’ve helped create that have challenged people to grow, be better, do better and pay it forward. More recently, I am extremely gratified that Linear Air has been able to provide a safe travel option during the pandemic. There are still many important reasons — both professional and personal — that people need access to air travel right now. Being able to offer a high level of safety, comfort, convenience and peace of mind to these travelers makes us feel good about the services we offer.

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. 🙂

I would love to see the message of Junior Achievement reach more young people today in the same way it reached me many years ago. I want them to have the same chance to realize their potential and to think to themselves, “Why not me? Why can’t I be an entrepreneur and be creative and drive my values out into the world?” As a volunteer for my local Junior Achievement of New England chapter, I have seen firsthand the powerful impact of this message.

How can our readers follow you on social media?

Linkedin

Twitter

Facebook

Instagram

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