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If I Knew Then: Serial Entrepreneur Reveals Why Second Place Isn't Good Enough

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Sam Shank has a career path that's a little bit more eclectic than some in Silicon Valley. The co-founder of San Francisco-based HotelTonight, a mobile app that allows users to reserve rooms at the last minute, decided he didn't want to start his entrepreneurial journey working for another startup or a mega software corporation. Instead, he tried to make it in Hollywood, where he served as the assistant to Wes Craven in the box office hit Scream.

Figuring Hollywood glamor wasn't for him, the travel-obsessed Shank then dipped his toes into entrepreneurship with the launch of hotel-review site TravelPost and later was the CEO and co-founder of DealBase, a travel search engine.

Now, Shank is giving consumers a lot to scream about with his latest startup HotelTonight. The company recently announced it raised an additional $45 million in a Series D round, bringing the startups total raised capital to more than $80 million. We chatted with Shank what he has learned along the way.

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Q: How did you go from working on movies to launching a mobile app for travelers?

A: I come from a long line of entrepreneurs, so it was always very natural for me to think about starting my own business and something I wanted to do. I was attracted to technology but was equally interested in filmmaking. I knew I wanted to get some additional experience and exposure in those industries before I started a company, so I could find the area I was passionate about.

With film, I had a great time working in Hollywood for a year, but decided it wasn’t the right place for me to start a business -- the distribution of film was so controlled and constrained it made it hard for people to be entrepreneurial in Hollywood.

I decided the internet business was more interesting for me as a platform and to build a business in. After launching travel-deal search engine Dealbase, I got a lot of familiarity with travel deals and the mentality of people looking for deals.

When I started to think about mobile and HotelTonight, I was well-positioned in terms of my knowledge of the hotel industry and mentality of value-seeking hotel shoppers.

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Q: Knowing what you know now, what would you have done differently?

A: With my first two businesses, we were trying to do something better than something else that already existed. With HotelTonight, we were identifying a new category and being the best.

Even though there were other companies selling hotels, we were the first to focus on making it easy and convenient to book a last-minute hotel on a mobile device. It created a new use case around people being spontaneous.

Both approaches -- doing something better or creating something new -- requires roughly the same amount of work. Yet, the benefit of being No. 1 in a category is so much more rewarding.

My recommendation, especially for first-time entrepreneurs, is really think how you can be best and not just better.

Q: What do you think would have been different if you had this knowledge about being best versus better?

A: I probably wouldn’t have started Dealbase, or if I started it, I would have worked on making it more differentiated than it was. But hindsight is always 20/20. If I hadn’t done Dealbase, I wouldn’t have had the knowledge around the space to spot the opportunity with HotelTonight. It’s not that I would have done it better, but it would have looked more like HotelTonight than Dealbase. Still, I have no regrets.

Related: How a New App Is Helping Hotels Fill Rooms

Q: How do you think entrepreneurs can benefit from this knowledge?

A: I think young entrepreneurs should be very honest with themselves about how different their service is. It’s important for entrepreneurs to think about how they can make their ideas more revolutionary, not just incrementally better.

Q: Besides inventing a time machine, how might they realize these sorts of helpful pearls of wisdom sooner?

A: I think it is very hard to get that level of strength and knowledge before you actually do it yourself. Go into your entrepreneurial endeavor knowing you’re going to learn a lot and realizing you don't have all the answers. Make sure you have a good group of trusted advisers, ones that are neutral, want to help you succeed and help you through challenges.

Q: What are you glad that you didn’t know then that you know now?

A: I didn’t know how hard it would be to recruit a great team. If I had known, it might have scared me off.

Q: Can you offer some advice to aspiring entrepreneurs?

A: You’re only going to learn how to climb the mountain by climbing the mountain. If you really want to learn how to be an entrepreneur, start a business.

What do you know now that you wish you would have known then? Let us know in the comments below.


Lyneka Little

Written By

Is a freelance writer in New York. She's written about personal finance and small business for such publications as The Wall Street Journal, MainStreet.com, Walletpop.com, People magazine. She also works as a freelance producer covering money at ABCNews.com. Little attended Howard University where she studied journalism. She loves drinking wine and tweeting, preferably at the same time. Follow Little on Twitter @Lyneka.