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Going Against the Flow: Eric Grosse, CEO and Cofounder of Chairish

03/04/2016 12:39 am ET | Updated Mar 04, 2016

Eric co-Founded Chairish, the world's first online consignment marketplace for design-obsessed people to buy and sell exceptional pre-owned home furnishings. Previously, he co-founded Hotwire and was President at Expedia Worldwide, CEO at TaskRabbit, and Executive in Residence at Matrix Partners. His specialties include general management, strategy, financial and business operations, product development and marketing. Eric is a Harvard Business School graduate, and currently lives in San Francisco with his family.

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Eric Grosse

What does entrepreneurship mean to you, and what underlying characteristics do you see in successful entrepreneurs?

Eric: I've found that starting a new company is the ultimate test of passion, determination and persistence. Passion is an especially important energy source to get you through the rough and tumble early days when so much is at stake, such as honing the core concept and attracting a founding team, investors, press and industry supporters. If you're not really, really, really into your idea, no one else will be either.

Creating something new is the core of entrepreneurship. We live in a culture that loves shiny new objects and glorifies successful outcomes but not necessarily the sweat, doubt and countless mistakes that often make a successful end result possible. Most entrepreneurs I know have tremendous respect for the company building process. Like Teddy Roosevelt, they give "full credit to those actually in the arena, who strive valiantly, who err but know great enthusiasms, who at best know the triumph of high achievement and at worst fail, but at least fail while daring greatly."

What are you most proud of in your professional career?

Eric: I'm proud of helping start two companies that have passionate and loyal customer followings. Travel is expensive, so it is very gratifying to hear stories from customers who were able to go on vacation or attend weddings thanks to Hotwire. Similarly, Chairish has a similar ambition to make an inherently expensive product - quality furniture and decor - more accessible to more people who share an appreciation for fine design and craftsmanship.

As an entrepreneur, I'm also proud of starting and growing companies that create exciting professional opportunities. Successful companies provide opportunity for colleagues to pursue and realize their own ambitions within a shared, common objective. Company events are an especially tangible reminder of all the people who signed on for the ride to build something great together.

If you could do something over in your life, what would it be?

Eric: I'm not a "woulda shoulda coulda" kind of guy. If life were a river with many off-shooting streams, I'd rather continue to move downstream and make the best of a tough situation versus rowing backwards and trying to start over. For example, I was absolutely crushed by the loss of my father at a formative time in my life, but losing him early has made me more self reliant and willing to try something new, like moving West soon after finishing graduate school. In retrospect, San Francisco has been a blessing, but I doubt I would have switched coasts if my father hadn't suddenly passed, a traumatic event that I would have done anything to change at the time.

More recently, I sometimes find it harder to watch others navigate their own river compared to dealing with the ups and downs of my own journey. Especially as a father, I find that the hardest challenge is learning when to step in versus standing back and letting the river provide lessons through direct experience.

Tell us about an instance where you had to go against the flow to realize your goal.

Eric: I find raising capital to be an exercise in going against the flow. I've been in situations where many say no before some say yes. In these cases, remaining positive when surrounded with so much rejection is easy to say, but hard to do. I've also found the inverse to be true, as it is tempting to ramp up spending and kowtow to investor growth demands if capital comes cheap and easy. In easy money situations, it takes discipline to build a high growth and capital efficient business that endures for the long haul.

What challenges in the furniture and decor category are you solving with Chairish?

Eric: Buying and selling quality vintage furniture should be fun and easy, but it isn't. Sifting through pages of schlock on Craigslist is an uninspiring pain, pricing is a mystery, and there's always the question of how to arrange for big, bulky items to be delivered to your door. Prior to Chairish, no marketplace yet existed that focused exclusively on addressing the curatorial, pricing and fulfillment challenges unique to furniture, which is kind of surprising considering the category is expected to reach $300 billion over the next decade in the US alone. Additionally, the fact that quality furniture is built to last decades, but Americans move on average 11+ times in their lifetimes, also points to the need for a new solution like Chairish.

We screen all items prior to acceptance to ensure a high quality experience for both the sellers and buyers. All the other challenging aspects of selling online - listing, marketing, delivery services, etc - are also taken care of by Chairish. Once items are accepted, sellers can just sit back and collect a check, while buyers can shop 75k+ items with the confidence of easy delivery and a 48-hour return policy. What's not to like!

What drives you? How do you measure success for yourself?

Eric: As I get older, I find myself increasingly motivated by a desire to help others. At Chairish, I always try to put my colleagues in situations where they can succeed, as well as step in to help when things don't go as planned. I also work with our executive team to ensure resources are allocated in a way that helps our customers and builds marketplace loyalty. As a startup with limited resources, there are always things I wish we could do but can't, but like a M.A.S.H. unit we always work to take care of the important stuff.

In terms of how I measure success, at Chairish we keep it simple with Net Promotor Scores (NPS) and other customer surveys. As a small company, we keep tabs on employee satisfaction with all-hands meetings, quarterly events and regular 1-1 meetings with managers. At home, the look my wife gives me usually tells me all I need to know about how well I'm supporting her and the kids!

If you were to give advice to your 22-year old self, what would it be?

Eric: I'd encourage my younger self to develop a broad set of interests and pursue them continuously and enthusiastically, even if there may not be any logic that ties them all together. The larger the set of experiences, the more opportunities to bring them together and create something exciting and new. I took classes in a broad variety of fields while in college, interspersing traditional subjects like history, calculus and economics with creative classes like sculpture, music and art history. When I graduated college at 22 and embarked upon my professional career, I became at times more intellectually cautious and preoccupied with fitting in with my new work environment. Only later did I gain a greater appreciation for the benefits that come from a broad set of experiences beyond a traditional work environment.

Follow Eric Grosse at @ericgrosse5, check out the other interviews in Going Against the Flow series at http://www.huffingtonpost.com/charu-sharma/ and join this movement to empower 1 million female entrepreneurs on goagainsttheflow.com.

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