In the green room at Phocuswright with... Brad Handler

Brad Handler, founder and chairman, Inspirato

Brad Handler, formerly of eBay and Apple, leads corporate finance and strategic initiatives at Inspirato, a luxury hospitality company. At The Phocuswright Conference, he will take part in an executive roundtable on short-term rentals.

In a series of interviews with executives participating at the event in Florida in November, PhocusWire finds out what makes them tick...

Does the industry or do travelers drive change?

Travelers drive change. Everyone in the industry travels, and every unhappy experience is a stepping stone to change. We founded Inspirato as travelers who wanted to change the way people spend time with family and friends.

What travel industry development or brand do you wish you'd thought of first?

One of the Sea Island hotels had a nightly service where you could select the type of cookie and the type of milk you wanted delivered that evening between 7 and 10 p.m. That was awesome. Not sure if they still do it.

Do you agree with the often‐used phrase, "travel planning is broken”?

I do not. If it is broken for you, however, then you must find a better solution. Fantastic solutions are out there at every price point. You just need to find them.

Tell us about your favorite vacation.

My wife and I love Florence, Italy. We love to go off–season and combine four or five days around Florence with another European destination. That way, we get to try new experiences and enjoy our favorite place in the same trip.

How do you stay inspired?

I read the emails our members and Inspirato Passholders send us about the Inspirato experience, both the good and the bad. The good are inspiring for obvious reasons. However, the bad inspire us to find better ways to meet and exceed their expectations.

How do you book your travel?

I am very particular, so I do it myself. Flight times and seat assignments are important to me. I like certain airports for connections and will avoid some at all costs.

What's your one travel hack everyone should know?

Be nice to the person on the other end of the phone or to whomever you are talking to in person. It costs nothing and you can reap enormous rewards.

How do you define success and how do you measure up to your own definition?

Constant innovation is success for me. Stagnation would be failure. I think we have done a good job of innovation over the past 20 years in this industry.

What was the best part about a previous job that you had?

I was eBay’s first lawyer. As a result, I was part of defining the rules of the road for all e-commerce. That was incredible experience. However, in high school I worked at a gelato store and got all the gelato I wanted for free. At the time, that was pretty cool.

What book do you recommend to others and why?

Milton Steinberg wrote a book called As a Driven Leaf. The main message of the book is that no matter what is going on around you, if you stay true to your beliefs you remain a person of honor.