Alyssa Rapp

Alyssa Rapp

Founder & CEO, Bottlenotes

In the great debate of what to do next after graduating form Yale, Alyssa knew she wanted to take the road less traveled by chasing her childhood ambition to be the first female president. Several political campaigns and one Standford Wine Circle later, Alyssa found the intersection of her interests by creating a community for READ MORE »

  • ON Journey

    Q: Please share with us the story of how your professional journey began and has brought you to where you are today.

    A: My professional journey formally began immediately upon my graduation from Yale in spring 2000. In the great debate of what to do next, I knew that I wanted to take the road less traveled (I guess I always have and always will), but I also felt it was the right time and place to “test drive” one of my childhood career ambitions: to be the first female president. So I decided that the best way to gain experience that would be relevant to that end-game would be to work on the country’s most exciting political campaign that election cycle, which happened to be Hillary Clinton’s (first) Senate race, in my estimation. So I moved to New York for the summer, schlepped across town on blistering summer days by foot and subway, and began my professional journey as unpaid slave labor as a summer intern on the “Hillary for New York Senate” national finance team.

    My early successes there (I quickly sold two $10,000 contributions- a hefty sum then and now- to Chicagoans who were thrilled to support both Hillary and get their photographs taken by Annie Lebovitz) showed me that I liked fundraising more than I anticipated. The world being the place it is, word on the street in Chicago was that I was in political fundraising now, so when the finance director for a liberal US Congresswoman, Jan Schakowsky from the north side of Chicago was gearing up to go to law school, and needed a replacement, my name was recommended. One thing lead to another, and I ended up having the privilege and pleasure of serving as Jan’s national finance director from Fall 2000-Spring 2003, where I created the Ultimate Women’s Power Lunch, now in its 10th year and running (with over 2000 women attendees annually); I also helped her spearhead the Women LEAD program through the Democratic Congressional Campaign Committee (a group that endeavored to raise money from female donors to benefit female candidates).

    As much as I loved the political race, I realized in those three years that I didn’t dream of staying in that game as a staffer, but rather, if I were to return to politics, it would be as a candidate someday. What I did learn was that I loved running “small businesses” and “start-ups” that are US political campaigns- and my dreams of entrepreneurship in the business world inspired me to apply to the most entrepreneurial of graduate schools, Stanford University’s Graduate School of Business (“GSB”).

    While at Stanford, I co-presided over the GSB’s “Wine Circle,” a wine club with hundreds of members. We organized multiple events each month, where wine experts would come and share their wine and wine knowledge with us.

    The idea for Bottlenotes was an outgrowth of these experiences. While running the Wine Circle, I was struck by how my well-educated, well-traveled peers were surprisingly intimidated by wine. I was also impressed by how “thirsty” some of the great wine brands were to market their products to this “Millennial Generation” audience. Bottlenotes was born out of the desire to demystify the world of wine for new to intermediate wine enthusiasts, and to continue to help find creative ways to help brands gain access to this booming audience, leveraging technology and content.

    Gone are the days where Millennial Generation (20-29) and Generation X wine enthusiasts look to “dead” scores with no personal relevance to figure out which wines to try. In are the days where new wine enthusiasts look to a trusted source for wine recommendations, whether an expert “friend” or resource or to the most knowledge wine friends in their social circle. The problem was that Millennial Generation and Generation X wine enthusiasts lacked a fresh, contemporary, unpretentious, and social-media savvy resource and community to turn to.

    Today, Bottlenotes, Inc. is the leading new media company in the wine space dedicated to educating and entertaining wine enthusiasts via four primary channels: The Daily Sip™ email newsletter (received daily by over 135,000 wine enthusiasts nationwide), Around the World in 80 Sips™ national event series, Bottlenotes Social (leveraging a 50,000+ person audience on Facebook & Twitter, and of course the community on, and Bottlenotes Mobile, the company’s Webby-honored iPhone app. For our combination of online editorial content, large-scale consumer wine tastings, comprehensive online community via the website and social media platforms, and newly launched iPhone application, industry insiders and consumers alike consider Bottlenotes the wine and lifestyle guide for the next generation.

    As we continue to stamp out our domain in wine, we are also beginning to look to adjacent verticals in which to expand our new media model (email/social/mobile/interactive events), betting big that these platforms for education and entertainment will be of interest to enthusiasts in other categories even beyond wine.

  • ON Leadership

    Q: What are 3 characteristics that you believe define great leadership?

    A: Vision, Perseverance, Resilience

    And in terms of tactics:

    Hire passionate, driven, smart, capable, young people- give them clear goals and directions- and get out of their way as they execute these goals.

    If you have to make the choice of someone extremely passionate and hard working who would be a great cultural fit for your organization with less domain expertise vs. someone with simply more domain expertise, hire the hungry young person every time. Skills can be taught; drive cannot.

    Surround yourself with absolutely phenomenal mentors who will help maximize your own leadership potential.  My business partner and I feel strongly that we would have never come as far as we have without the tremendous support and coaching from our board of directors and advisors, with whom I feel it is a true privilege to work on an ongoing basis. (Complete list available at <>)

  • ON Innovation

    Q: If a business has several, viable ways to grow and innovate, how do you pick the best road to take?

    A: In terms of which products or services to innovative, the question is one that’s easily answered, in my humble opinion: innovation is almost always the result of finding a solution to a problem (e.g. I feel intimidated by/want to learn more about wine; I need a trusted source of information to “guide” me through the process, like a French tutor if I want to learn French). Such solutions come from listening to a customer’s needs, being the customer yourself and knowing what’s missing in the marketplace to meet those needs, and devising a product or product set that meets those needs. Innovation is “problem solving.” It often also comes organically as an “extension” of an earlier idea—a solution to a “new problem” you find along the journey.

    For example, our original wine club business model enabled us to serve as a “personalized” sommelier service for individuals around the country. Once some of those customers started using us as a resource for personalized recommendations in their day-to-day lives, they wanted to use us a similar type of resource when starting their first “cellar” when getting married. Hence the idea for the Bottlenotes Wine Registry was born. Today, it still exists, powered by Sherry-Lehmann! (You can find it at <>).

    More broadly, I am an innovator leading a team of innovators. We’re innovating day-in, day-out, as to what defines a “new media” company, having added social media marketing services, for example, to our suite of services at the request of our brands in the last three months alone.

    Going back to the beginning, when making our shift from e-commerce to a media company, simply staking the claim that one could create an entirely email-based, digital “magazine” in an industry as stodgy as wine—positioning The Daily Sip™ as the “Daily Candy” of wine—was and is innovative. Having done so, we have garnered a circulation from 30,000 to 140,000 in less than two years, one that is almost on par with that of Food & Wine’s email newsletter already.

    In addition, our Around the World in 80 Sips™ national event series is clearly innovative in the wine space, a business model Claudia and Shecky’s know well. The goal of our wine events is to provide cool, hip, fun, approachable and sophisticated environments in which consumers can taste over 80 wines from around the world in one evening, in stark departure from competitors’ stuffier, stodgier, more elitist wine events. The proof is in the pudding here too: we expanded from three cities (New York, Chicago, and San Francisco) in 2009, to now six in 2011, and will continue doubling in size to 12 events in 2012.

    We’re only at the tip of the iceberg with respect to innovation surrounding problems and solutions via mobile devices. We’re continuing to help come up with ways that enable users to better remember the wines that they try and share these wines with their friends.

    Similarly, with respect to innovation, its cycle and process never ends: this year we have also piloted a “restaurant week for wine,” in partnership with, one that after its three-city pilot could roll out nationally in 2012.

    The ongoing innovation of new products and services in a given category day-in, day-out, has unequivocally been our greatest strength as a business. The path that one decides to pursue with what has been innovated must start from a place where you’re solving a compelling solution for a consumer, but a solution that is simultaneously marketable, profitable, timely, and scalable.

    In sum, in terms of which road to take in the innovation journey, in part, the answer is driven by necessity (which path or product will drive me to profitability the most rapidly?), part out of serendipity- but always, in either context, providing a solution to some compelling problem that the consumer (or business) has.


  • ON Entrepreneurship

    Q: What’s your best advice for an entrepreneur in an early/bootstrapping phase? Or in a growth/need to ‘now scale’ phase?

    A: Dogged determination and perseverance are absolutely necessary, although insufficient, for success. The number of times I have had to stare fear right in the eye, acknowledge it, be motivated by it, but ultimately, just push it aside to continue the proverbial uphill climb, often without the requisite “nourishment” (aka: working capital), I can hardly count. But particularly early on, you have to “want it” more than you “fear it.” You have to be willing to give up almost everything else to achieve your said goal too. Also, I have been reminded time and time again that, as one of my closest friends and advisors, venture capitalist Emily Melton (formerly with DFJ & Mayfield Capital) poignantly states, “You have to be present to win.” In short, hang on as long as possible in life and business, and often times, just when you think you can’t hang on any longer, the tide often turns.  Or, to quote Winston Churchill, “Never, ever, ever, ever, ever, ever give up.”

    Most important, it’s not how well you start, but it is how well you finish it by which the race is measured. Start strong, finish stronger, is a lesson of which I’ve been continually reminded as an entrepreneur. So for boostrappers, raise enough capital to get you through to a prototype, and keep pushing the envelope in terms of customers and revenues all the way through the finish line (next financing, profitability, M&A, etc.).

    You’re only as strong as your weakest link- team member, vendor, balance sheet, etc. Start the race with as many strong links as possible- and if at all possible, 2x the invested capital that you think you’ll need. As hard as it seems, it’s always easier to sell a dream on a piece of paper than an early stage business. Worst case scenario, you’ll end up with a cash buffer—which  you can use to accelerate your growth if things are really exceeding your expectations—and that can only be a good thing.


  • ON Vision

    Q: I love the quote “the bigger the vision, the smaller the first step”. Right now, what is the big vision you have for your career?

    A: Whether in a small company or eventually a large, public one, in a for-profit environment or a non-profit environment, I hope to always inspire and maintain a sense of culture that parallels those of the teams with whom I’ve climbed major mountains: tight-knit, highly interdependent, together conquering some big, hairy, audacious goal, where each individual is responsible for a specific functional role (or three), but ultimately, the success of the team is tied to everyone moving in the same direction, steadily climbing until arriving at the summit.

    As for my career, I hope that Bottlenotes will not only evolve into the “Wine Spectator” for the next generation, but that when it does, it will find a happy home in a larger media company, so it continue to grow and expand as rapidly as possible.

    Thereafter, whether I would stay with the company/concept internally to a larger media company, head back to the trenches to start a new company, or do something unforeseen, we’ll see. Someday, I hope to be able to look back and see and say that I started and ran many companies, was top-tier manager and leader, wrote books that inspired and helped people along their own entrepreneurial journeys, was a civic activist and philanthropist and leader on causes about which I care deeply on the side, and someone who dedicates a period of my life to serve publicly. When, where, how – remain to be seen. But these are my goals professionally speaking.

  • ON Branding

    Q: What do you feel separates your brand from your competitors?

    A: That we are cool, hip, fun, and approachable, while sophisticated. Neither stodgy and pretentious, nor purely vapid and flimsy.  That the products and services we offer are discoverable and actionable.

  • ON Perseverance

    Q: What or who in your life gives you the strength to persevere?

    A: Inner voice. The one that encourages me to keep on pushing. And my athletic coaches in life have constantly reminded me to tap into my inner strength and persevere, childhood through present. And my fiancé, Hal Morris. Hal has had the luxury of the perspective of having been a professional baseball player. As such, he is highly versed in perseverance, thus consistently reminding me that so long as you have another at-bat, the opportunity to hit a home run, it doesn’t matter how many strikes or outs there are in the count, it is your job to focus and keep swinging to the best of your ability.

    And of course my family members who are close friends, and close friends who are like family to me.

  • ON Happiness

    Q: What simple things in life today bring you joy?

    A: Health. Friendship. Loyalty. Love. Homemade pasta. A hike in a beautiful setting. A great glass of wine in great company. A heartfelt conversation. Helping to bring out the best in someone else—child, family, friend, team member. Travel. Agadashi tofu, brown rice, vegetables, and well-made sushi. Ongoing exploration. Sencha green tea. Striving for new goals; achieving them; setting new goals; never giving up on them. Accomplishing something that scared me originally. Proving that people were wise to believe in me.

  • ON Perseverance

    Q: Life is full of setbacks. Can you share an experience of one, and how you were able to bounce back?

    A: There are too many to count. I sometimes feel like I face a new setback every day and am continually bouncing back. Life is a like a trampoline in my world these days.

    More specifically, we have come close to a major strategic partnership on two different accounts at the Company, both of which seemed to be heading in the right direction until the 11th hour.

    When those two deals did not consummate, I was seriously disappointed, to say the least. But I looked myself in the mirror, reminded myself that the test of character is not measured by how hard you fall, but by how resilient you are/how high you bounce back- and that success is not determined by how easily it is achieved, but who wants it the most. So I keep fighting.

  • ON Giving Back

    Q: What cause(s) have you chosen to support and why does it resonate with you?

    A: As a former contemporary dancer and choreographer, it’s no surprise that the first board of trustees that I’ve joined is for Hubbard Street Dance Chicago (< >) arguably the United State’s leading contemporary dance company. As such, I co-chair an annual wine event that raises >$50,000 for the non-profit annually (as of 2006). I love keeping the love of dance and choreography alive in my life through my work for Hubbard Street.

    In early 2010, I also founded the Coalition of Consumer Rights, a 501-c-4 organization that I started in response to the about-face policy reversal by the California Alcohol Bureau of Control, a reversal whose net effect greatly restricts consumers’ ability to purchase wine online. The non-profit’s advocacy work continues and has becoming influential to the new administration of California ABC leaders as they currently revise their policies about “Third Party Marketing Firms” (e-commerce companies) in the space, making them more consumer and small-business friendly. It feels good to be helping shape policy on issues with which I’ve been involved so intimately as a businessperson for a half-decade.

    Finally, as of 2010, I joined the Advisory Board for Spark’s Chicago chapter, a non-profit that matches inner-city, underprivileged students with apprenticeships in San Francisco, Los Angeles, and now Chicago. As an advisory board member, I am helping this non-profit build a footprint in and network of donors, other board members, and activists in Chicago (


  • ON

    Q: In the world, what are your three favorite cities?

    A: Chicago, New York, Paris

  • ON

    Q: In the world, what are your three favorite places to get lost?

    A: Jackson Hole, Napa Valley, Italy

  • ON

    Q: In the world, what are your three favorite places to shop?

    A: Bergdorf Goodman, Romi’s of Palo Alto,

  • ON

    Q: In the world, what are your three favorite restaurants?

    A: The French Laundry, The French Laundry, The French Laundry.

  • ON

    Q: If you were stranded on an island and could have an unlimited source of 3 foods (and calories were not a concern), what would they be?

    A: Wine, cheese, pasta.  Back here in reality, eggs, coconut water, and green tea.

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