Rick Libby – Founder of Traveling Vineyard

We also live what we call “the 5Fs,” which are fun, friendship, flexibility, fulfillment, and financial reward.

With more than 30 years’ experience working at consumer-based companies in an entrepreneurial role, Rick Libby oversees the day-to-day operations of Traveling Vineyard, where his official title is Chief Grape Stomper. Libby launched today’s Traveling Vineyard (previously known as The Traveling Vineyard) in 2010. Traveling Vineyard is a direct selling organization that first introduced the concept of in-home wine tastings to market its exclusive Traveling Vineyard wines—which are opportunistically sourced from high-quality vineyards worldwide and regularly earn Gold and Silver medals from Tastings World Wine Championships®. Under Libby’s leadership, Traveling Vineyard has grown from hundreds of Wine Guides to now over 5,000 across the United States.

Prior to Traveling Vineyard, Libby served as the Managing Director for a business unit of Roper Industries (NYSE:ROP) overseeing the rapid growth of a leading college and university payment and discount platform, Student Advantage. Before working at Student Advantage, Libby founded and served as President of The Traveling Vineyard, America’s largest home wine tasting company (and the predecessor to Traveling Vineyard). Libby has also served as President of MoveCentral, Inc. Under his leadership, the company made the Inc. 500 Fastest Growing Companies list twice and was acquired by Monster.com in June 2000. During a tenure as senior executive at Cendant Corporation, he developed new products across the travel, real estate and membership businesses of the company. Libby honed his general management, sales and marketing skills in the hospitality industry with Marriott. Libby is a graduate of Southern New Hampshire University and resides with his family in Ipswich, Mass.

Where did the idea for (your business) come from?

I had joined Geerlings & Wade in 2001, which at the time was a direct-to-consumer wine company selling wine via catalog. My job was to build a strategy to increase sales. Coincidentally, a conversation with a good friend planted the seed for a whole new approach to direct-to-consumer wine selling. My friend’s wife was a successful Pampered Chef consultant and he wondered aloud to me, “What if you sold wine like that?” I thought it was innovative—a “try before you buy” opportunity via casual in-home wine tastings, all guided by a wine consultant—which we now call Wine Guides. At Geerlings & Wade, we launched the concept immediately—our first party was in November 2001—and within the first month, sales started to grow. That’s how the Traveling Vineyard concept was born.

What does your typical day look like and how do you make it productive?

Each year, we are guided by 6 to 10 high-level strategic objectives. About half of my day is spent working toward these objectives, and the other half is spent on day-to-day operations. It’s important to me that I connect with Wine Guides and our team on a personal level each day, too.

How do you bring ideas to life?

We have an idea culture and a strong team of people who make a practice of thinking outside the box—particularly my partner, Huib Geerlings. Each year, Traveling Vineyard has launched something innovative to drive the business forward. One year, soon after I took over the organization, it was rebranding and modernizing Traveling Vineyard. Then, we launched “Sommology,” our proprietary wine tasting and food pairing methodology used exclusively by our Wine Guides. Another year, it was our Awesomm app, designed to help Wine Guides manage their businesses with ease and reliability, from anywhere. This year, it’s a new feature of the Awesomm app that will enhance the way our Wine Guides present our wines at tastings. We have a general drive to always be aware of, and never fall behind, the competition. We want to be a leader in the industry—from the way we buy our wine, to the way we package our wine, to the way we build our infrastructure.

What’s one trend that excites you?

Consumption of wine in the U.S. is growing and becoming even broader than ever, and that bodes well for business.

What is one habit of yours that makes you more productive as an entrepreneur?

I am competitive from the perspective that I want Traveling Vineyard to be a leader—that’s always been a habit of mine. We want to be at the forefront of everything. I am also adventurous and willing to try new things, which is a habit of mine in both my professional and my personal life—from motorcycling and challenging myself at CrossFit to sailing and scuba diving.

What was the worst job you ever had and what did you learn from it?

This is a story about a challenge more so than a “worst job,” but it represents a lesson I learned … While I was working for Geerlings & Wade, before I took over the business, we had brought in a new CEO. He had a different view on cultural standards than I did, and in working through that, I learned a lot about myself. I learned that I was willing to put it all on the line to preserve the values the company was built on: to support our Wine Guides and help them become successful entrepreneurs, rather than treat them as employees. For me, Traveling Vineyard is a company that pulls people up and inspires them to achieve great things for themselves, on their own terms. I ended up leaving the company based on this disagreement in 2005. And when they filed Chapter 7 in 2010, I put all my savings into buying Traveling Vineyard, relaunching the company, and staying true to what I believe makes our company successful and unique.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Stay healthy!

What is one strategy that has helped you grow your business? Please explain how.

Being innovative and living the brand battle cry, “hip, fun and sassy.” We have a brand that is human and that cares. Everyone in the organization lives it every day—we can’t be superficial. We also live what we call “the 5Fs,” which are fun, friendship, flexibility, fulfillment, and financial reward. At any given moment, one of our 5Fs is making a difference in someone’s life. I think this impacts our growth quite a bit. People feel that they are in good hands with Traveling Vineyard and that they matter—because they are and they do. They are Traveling Vineyard.

What is one failure you had as an entrepreneur, and how did you overcome it?

In the 80s, I helped start a company, but we were under-capitalized—it always takes much longer and it’s always more expensive than you think to get a company up and running, and make it successful. Rocket-ship stories are few and far between. It was a good reminder that you need to have a long runway.

What is the best $100 you recently spent? What and why?

A pass to an airport club room. When I have long stretches of travel, it’s nice to grab some solitude, particularly in an airport setting!

What software and web services do you use? What do you love about them?

I love Zoom which is a conference/meeting app, because it’s reliable, intuitive and easy to use end-to-end. I also like HubSpot for CRM, lead scoring and nurturing. It’s sophisticated and it’s allowing us to nurture each lead throughout the life cycle of the lead.

What is the one book that you recommend our community should read and why?

The Advantage: Why Organizational Health Trumps Everything Else in Business” by
Patrick Lencioni

It’s a great book. Although, no matter how many books you read on team culture it all comes down to intuition and treating people with respect. My dad taught me to work hard; my mom taught me to be kind. It’s that simple.


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