Alyssa Rapp



Yale University, BA, Art History and Political Science

Stanford University, MBA

As founder and CEO of Bottlenotes, an interactive media company in the United States wine and craft beer industries, Alyssa Rapp is fiercely dedicated to educating a new generation on the finer points of a good drink. With an eye for making the often complex world of beer and wine hip, fun and approachable, Alyssa is all about removing the sometimes pretentious tilt of the industry with democratic education.

Combining a personal interest in the world of wine with a fierce entrepreneurial spirit Alyssa has built an empire beginning with her website and building to books and national events. And even with a totally hectic schedule she’s doing a good job: Alyssa has been recognized by both Inc. and Playboy magazines as one of America’s most innovative entrepreneurs. 

Uncork a favorite Malbec – or perhaps Alyssa would recommend a glass of something sweet and white – sit back and read about how wine and business make the perfect pair.

Give life the best you have, and the best will come back to you.

What makes Bottlenotes different from other sites that cover wine and craft beer?

We target an audience of new to intermediate wine enthusiasts, craft beer enthusiasts, and recently, also cocktail enthusiasts. Our goal is to educate and entertain our audience with relevant, discoverable and actionable “bite-sized” amounts of content. I think our cool, fun, hip and approachable voice is a major differentiation, as is our general goal to “demystify” these products for our target audiences.

How did you evolve Bottlenotes from an idea to a full-scale business?

Bottlenotes started as a third-party marketing firm, and more tangibly, as the “Netflix of Wine,” endeavoring to deliver wine via wine clubs using patent-pending matching technology to consumers in 26/50 states. Due to a major regulatory shift in the category, we had to pivot our business model to a new media company – educating and entertaining our audience via content and live events. But our goals to help the next generation of wine (and now beverage enthusiasts) feel empowered to try and buy products that they like, and to be able to share consumer information about them in new, relevant ways, has remained constant since inception.

What does a day in your life entail? How do you organize your day?

While the time varies from 1 a.m. to 2 a.m. or 5 a.m. to 6 a.m., I make sure I triage my email inbox. Then, I connect remotely with my team members by phone anywhere from 8 a.m. to 10 a.m. The next chunk of my day is dedicated to cash flow analysis and scheduled calls and meetings. Just before lunch, I am on scheduled calls and team meetings, work on client/sales presentation prep, financial modeling, etc. I usually have a working lunch. If I’m at my desk it’s concurrent with ongoing client/sales presentation prep and financial modeling. The first part of my afternoon is devoted to scheduled calls or internal and external meetings. Before the end of the day I follow up on deliverables and find myself in more internal meetings or presentation prep. And before bed, I’m again tackling my email inbox.

What is your favorite aspect of your job?

The diversity of experience, the never-ending learning and the interactions with great people (team members, investors, board members, clients, etc.) are all the favorite aspects of my role as a startup CEO. The range and variation in collaborations with internal team members, in addition to relationship development with external clients, marketing partners and most other key stakeholders provides a healthy balance of management challenges.

What career challenges are on your radar?

How to manage life as a working mom with a 2-and-a-half-year-old and an infant (due 3/16/15)!

Is work-life balance ever a problem for you? If so, what is one no-fail tactic you use to create balance?

My secret to work-life balance is daily workouts, as described in an article I wrote for Forbes that you can read here.

What are some of the rules you live by?

Give life the best you have, and the best will come back to you.

What advice would you share with a younger version of yourself?

The world is not solely filled with benevolent actors — but you will find a way to deal with all of them. Seek the most loyal team member possible (see reasons enumerated in an article I wrote on leadership and loyalty for Forbes).

What is one of your most memorable career accomplishments?

Pivoting the enterprise from an ecommerce play to an interactive media company as a result of a major regulatory shift in the category, all during the Great Recession of 2008-2009, is something I’m proud of. I described that experience at Tony Hsieh’s Catalyst Week.

What qualities does it take to be a successful entrepreneur?

It takes determination, stick-to-it-ness, confidence and true grit.