In the green room at Phocuswright with... Sam Shank

Sam Shank, HotelTonight/Airbnb

Sam Shank sold HotelTonight, which he co-founded in 2010, to Airbnb earlier this year for a rumored $500 million. At The Phocuswright Conference, he will take part in an executive roundtable on the future of the funnel.

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

Do you think startups in travel right now are at risk of being overvalued?

As is the case with many industries, there are companies that seem overvalued now but will grow into their valuation. In the travel space, there’s clearly an opportunity to build massive companies given the size of the industry.

However, it often takes much longer than people expect, given the low frequency of purchase and challenges getting customers or hotels to try new services.

What are the gaps in your experience and knowledge of the industry?

I’ve never worked in a hotel, so am less seasoned on hotel operations. Because of this, I love spending time with the frontline hotel staff and hearing feedback on what is working for them and what could be made easier.

Think back to five years ago. Did you envision this is where you would be?

Definitely not - I feel incredibly fortunate to be where I am! HotelTonight has been quite a journey and Chapter One couldn’t have ended any better. It’s a privilege to help people have some of their best moments through travel. I take the responsibility seriously and it’s what fuels me to continue building great products with the team.

Who is the person you most admire within the industry?

A few people stand out - one is Ian Shrager - a pioneer in the industry, inventing a new category of hotel, which is not an easy feat given how massive the industry is. It’s also a category that I and HotelTonight have a strong affinity toward - boutique and design hotels.

Who uses your product in ways that you never expected?

Golf caddies - which I could not have anticipated yet makes perfect sense. They are constantly on the road and in need of an affordable place to stay, often at a moment’s notice (when their pro makes the Friday cut!), which lends itself well to using HotelTonight.

In addition to the traditional small business traveler, we tend to also attract this type of non-traditional road warrior - like the golf caddy, tattoo artist, fashion designer, chef, etc. The spontaneity and unpredictability of their schedule makes HotelTonight a perfect fit.

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

I’ve always been driven by the desire to create a product that people love and makes their lives more fun. With HotelTonight, I believe we’ve accomplished that and made the world a more exciting, spontaneous place. Even my parents who are incessant planners have become more spontaneous.

Looking ahead, I’m really energized by what we’re building for hotels and guests on Airbnb. Lots of work to do - can’t wait to see it come to life.

What question would you not want to be asked in an interview?

What my favorite hotel is - there’s too many incredible ones to possibly choose just one!

What can be done to make the travel industry more diverse in terms of race and gender in senior positions?

It’s such an important topic and there’s clearly a lot of proactive work that needs to be done. I feel fortunate to be at a company that takes it so seriously and is making commitments to building a more diverse and welcoming company, and in doing so, also influencing the industry at large.

There are teams and initiatives at Airbnb solely devoted to the mission of diversity, including affinity groups that are employee-led, focused on creating more awareness and advocacy around the issues employees value and that help guide the company’s diversity initiatives in recruitment, leadership, product development and community outreach.

Airbnb’s mission is to create a world where anyone can belong anywhere and this extends to the workplace as well - creating a place where everyone feels welcome and all voices are hard. I’m excited to be part of this important, invigorating work.

What's your morning routine?

I get up around 5:30 a.m. to beat the traffic into San Francisco. I listen to Audible during my commute, alternating between escapist fiction and a business book. Right now I am listening to Everything Store about Amazon.com’s by Brad Stone, for the second time as a lot of the Airbnb senior executive team is from Amazon.com.

Once I get to the city, I do a group fitness class at 6:30 a.m. and then head into the office.

What's your one travel hack everyone should know?

ClassPass! [Editor's note: This is also a favorite of senior reporter Mitra Sorrells on the road.] I use it to find great new workouts when on the road. They have a great selection in most major cities around the world, and it’s a fun way to workout with locals and experience a workout that’s locally inspired. I’m about to do a kickboxing class in Singapore.

What's your must-have app?

I use Snapchat to keep up with our 14-year-old son - our Snapstreak is over 100!

Describe your desk and working environment

I sit in an open floor workspace and desk, alongside colleagues at both HotelTonight and Airbnb. I split my time between the two offices, working three days at Airbnb and two at HotelTonight. I don’t keep much at my desks as I’m always moving around. My happy place is with the team brainstorming in front of a whiteboard.