THE BLOG
09/05/2014 12:35 pm ET Updated Nov 05, 2014

Women in Business: Q&A with Alyssa Rapp, Founder & CEO of Bottlenotes, Inc.

Alyssa J. Rapp is the Founder & CEO of Bottlenotes, Inc., the leading interactive media company in the U.S. wine and craft beer industries. Bottlenotes is dedicated to educating and entertaining consumers via four primary channels: (1) email newsletters (The Daily Sip®, received daily by over 350,000 wine enthusiasts by email and 265,000+ on Facebook, and the Weekly Pint, with over 150,000 subscribers both on email and via Facebook), (2) large-scale interactive events (Around the World in 80 Sips, Taste Around Town, and iBev, the leading social and digital media conference for the beverage industry), (3) social media platforms, and as of 2014, video content.

Alyssa was named in Inc. Magazine's "30 Under 30" coolest entrepreneurs in America, one of Playboy.com's "10 Sexiest CEOs in America," and one of the wine industry's 100 most influential people by Intowine.com in both 2012 and 2013. Most recently, Alyssa accepted two awards on the company's behalf at the Empact 100, featuring the top 100 companies with a founder under 35: both the People's Choice Award and the Top Advertising and Marketing Company award.

Alyssa is the author of Bottlenotes Guide to Wine: Around the World in 80 Sips® (Adam's Media, October 2008) and frequently appears on national television as an expert on wine and entrepreneurship. Alyssa earned a B.A. in Political Science and the History of Art from Yale University in 2000 and an M.B.A. from Stanford University's Graduate School of Business (GSB) in 2005; she is proud to join the GSB as an appointed lecturer on the Global Dynamics of the Wine Industry as of Spring 2014.

Alyssa serves on the Board of Trustees for Hubbard Street Dance Chicago, the country's preeminent contemporary dance company, and on the Executive Board of Spark Program, a national non-profit that provides transformative apprenticeships for at-risk middle school students.

How has your life experience made you the leader you are today?
I believe that the role models in leaders shape one's leadership style; as such, I have clearly been deeply influenced by role modeling providing by my mother and step-father in leadership since my youth, and over the past ten years, in the leadership style that I've observed in my husband (which is very different than my own, but a great point of reference). My experiences in athletics and dance as a child/teenager/young adult, in addition to my experiences as a working professional in politics/business, and my ongoing interactions with a peer group of leaders in my fellow Stanford GSB alumni, all have shaped the person, thus leader, that I am today.

In terms of athletics, I was a serious gymnast from 7-17, and a contemporary dancer from 16-21. Both experiences shaped my leadership style from an early age.

My experiences as a gymnast taught me to conquer my fears, and that the greatest battle one often faces is in one's mind/having the self-confidence to believe that you can achieve your dreams, no matter how big, audacious, or scary that they seem, so long as you work extremely hard toward them. During my gymnastics days, I woke up every day prepared to work on mastering a new trick on the balance beam or uneven parallel bars, for example, pushing my body to achieve a goal or dream set by my mind, in spite of the inherent risk and challenge in so doing. So much of my experience as an entrepreneur has drawn upon these same techniques of goal-setting, fear management, and unwavering commitment to achieve a goal, that without my training as a gymnast, I don't know if I would have cultivated the "true grit" required of entrepreneurs.

As a contemporary dancer and choreographer, I enjoyed a different leadership challenge: that of communicating a creative vision (of movement, and movement sometimes set to complex scores of classical music) to a diverse group of people, both clearly enough to translate my vision into their movement and with enough flexibility to enable those dancers to make the choreography "their own." Choreography required showing up to the rehearsal with a game plan, while also being open to serendipity and organic evolution of the piece. The experiences I had as a contemporary dancer/choreographer -in inspiring a group of people to follow one's vision while being open to and capitalizing upon a team's creativity and unique personal strengths- indelibly shaped my approach to leadership today.

There is no doubt, however, that who I am today was profoundly shaped by my parents, Fay and Daniel Levin, who's individual and shared public record for leadership speaks for itself (she the former US Ambassador to the Netherlands amongst so many other extraordinary leadership roles, he the Chairman of The Habitat Company and Managing Partner of the East Bank Club, and they together, so many things philanthropic).

Similarly, I count my lucky stars every day for the leadership training that I received at Stanford University's Graduate School of Business from numerous academic stars, and for the global leaders in professors and fellow alumni that I have befriended throughout my time at the GSB as a student, as an alumna, and in the most recent few months, as a guest lecturer at the school.

Whether familial or professional, I think it is safe to say that my leadership style has been shaped by my parents, my athletic coaches, my mentors, my colleagues, and my friends. Most recently, my leadership ability has been challenged by our toddler, Audrey.

How has your previous employment experience aided your position at Bottlenotes?
My work as a political fundraiser for U.S. Congresswoman Jan Schakowsky post-college, pre-business school, afforded me the opportunity to work with a political leader by definition, but more, a woman whose hands-off leadership style greatly impacted my own. Jan taught me that if you hire people whom you trust, no matter how young, you should get out of their way/let them run hard on your behalf when managing whatever program or product or project that they have been assigned. Jan gave me an incredibly opportunity to bring a brand new program that I had envisioned to life in the Ultimate Women's Power Lunch (now attended by over 2,000 Chicago women annually for over 13 years), in spite of having been only 22 years old at the time. Based upon this experience, I now hire people in their early 20's who are equally hungry, and equally ambitious- and when I do, like Jan, I do my darnedest to stay out of their way and let them run toward the goals that we set together for themselves and the company.

What have the highlights and challenges been during your tenure at Bottlenotes?
The highlights and challenges have been almost too numerous to count- and often, intertwined. Having the strength and conviction as a team to pivot from an e-commerce concept to an interactive media company, in the midst of the economic crisis, and to make it out the other end, is clearly one of the biggest challenges we have faced, and our survival in 2008-2009 one of the highlights.

To now have attracted a world-class board of directors and advisors, loyal and talented team members, to have scaled to a degree that we have attracted best-in-class strategic partners like Condé Nast Enterprises, marketing partners like Opentable.com, and most important, a loyal and vast audience of highly engaged consumers- to whom we can connect our fabulous client and brand partners- these are all highlights.

How is Bottlenotes changing the US wine and beer industries?
Our goal at Bottlenotes is to make wine and craft beer cool, fun, hip, and approachable. We like to demystify the products that we write about /that our audience tastes at our events. Our goal is to provide content that is "discoverable and actionable" and create live experiences that bring the product to life (literally) to our community of tasters.

In short, we are democratizing and U.S. wine and beer industries, making them less pretentious or opaque, more accessible, enabling wine and craft beer to become increasingly consumed as "daily luxuries." We strive to expand the pie (in MBA speak) of both wine, craft beer, and frankly any passionate audience whom we strive to serve in the beverage industry moving forward.

What advice can you offer women who want to start their own business?
Hire great women, reel in great women as board members and advisors, and lean on your network of fellow women investors and entrepreneurs throughout your years as an entrepreneur.

How do you maintain a work/life balance?
Daily workouts are pretty crucial to my ability to achieve work-life balance. Starting my day with 60 minutes to myself clears my head and enables me to hit "reset" before I conquer the day's events. Working out with a great athletic coach (Abdul Sillah) has brought me back to my athletic roots, reminding me to dig deep and fight through the finish line with each activity. (Working out with a great group of morning zealots has also kept me coming out to workout, rain or shine, and keeps working out fun and social.)

Spending quality time with my husband, Hal, and our daughter, Audrey, is also crucial to my work-life balance, particularly on the weekends. Quiet dinners, hanging out, just reconnecting with each other as a family after a crazy week is absolutely crucial to my feeling balanced.

What do you think is the biggest issue for women in the workplace?
The gender inequity is still real in terms of women in leadership in the business world; the most recent article that I read in the Harvard Business Review that venture capitalists more frequently fund "attractive men" than women was particularly chilling.

More women in leadership is probably the biggest issue in the workplace. I'm doing my part with a team that's filled with 80% women and a handful of very secure men, and more women in leadership will continue to support, and mentor, great women.

How has mentorship made a difference in your professional and personal life?
Mentorship has made a massive difference to me personally and professionally. Mentors of mine in sports and school helped me to push myself to new heights; e.g. a close friend in college pushed me to seek research funding for my senior thesis as a sophomore, which I did, and that alone laid the foundation for my receiving a prize on the Best Essay on the American Political System from Yale, which is one of the awards that I have received about which I am most proud.

Similarly, a Bottlenotes board member thought I should try to get on national television, which now has happened numerous times with great brand-building effects for the company; I probably wouldn't have sought that without her encouragement.

For these reasons, I now serve on the board of Spark, a national non-profit organization whose sole purpose is to help create life-changing apprenticeships for middle schoolers by pairing them with mentors. The reason I give time and resources to the organization is now only is it led by phenomenal people, but I believe that the sooner mentorship begins in a student's life, the better the outcome for the student, and the mentor.

I believe in the Buddhist philosophy, grossly paraphrased, that if you want to learn, teach.

Which other female leaders do you admire and why?
I am privileged to count Marissa Mayer as a personal friend, and I probably admire her more than any other female CEO today. She is thoughtful, tireless, creative, and brilliant, and her willingness to take on new challenges, be generous, while maintaining her own work-life balance is truly impressive.

I also admire my mother. As US Ambassador to the Netherlands, she did such an exemplary job representing our country and its interests in Europe- that I wish there were more women in diplomacy like her.

Similarly, I admire Valerie Jarrett, who has worked tirelessly on behalf of President Obama and the country, I admire the great photographer Cindy Sherman for her creative genius and willingness to break boundaries through her work, Karen MacNeil, author of the Wine Bible, for her ability to become the living wine encyclopedia in a field dominated by men, and too many more to itemize. But these are the list of the first few that come to mind.

What do you want Bottlenotes to accomplish in the next five years?
It is my hope and dream that Bottlenotes becomes a household name & brand over the next five years, known as the go-to resource for education and entertainment for wine, craft beer, spirit, perhaps other beverages. That means that our Daily Sip, Weekly Pint, and future email newsletters would grow to millions of readers vs. several hundred thousand, that we would end up building the most watched video channel(s) in the beverage category, that our Around the World in 80 Sips® and Taste Around Town live events would expand from dozens to hundreds of US cities, that our iBev conference would become the defacto for industry leaders to attend, that our social media presences would outshine that of our competitors. Bottom line, Bottlenotes would be the leader in content creation and interactive experiences in the U.S. beverage industry.

And that we would have a ton of fun evolving into that company.