Serial Entrepreneurship | Alyssa Rapp

Serial entrepreneur Alyssa Rapp currently serves as the Managing Partner of AJR Ventures, a firm providing strategic advisory services to both start-ups and Fortune 500 companies in the technology, beverage and luxury goods categories.

Prior to AJR Ventures, Alyssa founded Bottlenotes, Inc., a media company rooted in the U.S. wine industry. She is also the author of Bottlenotes Guide to Wine: Around the World in 80 Sips.

Alyssa’s experience in the wine industry has earned her a spot among other lecturers at Stanford’s Graduate School of Business where she has taught a course on the global dynamics of the wine industry since 2014.

Named among the 30 Under 30: Coolest Entrepreneurs in America by Inc. Magazine, Alyssa has also been named one of the wine industry’s top 100 Most Influential People by

Career Success Q&A

What do you like most about your work?

Creating something from nothing. Envisioning products and services that will impact peoples’ daily lives for the better.


What level of education have you had?

In wine, none; in life, BA from Yale, MBA from Stanford, and I currently teach a class at Stanford business school on the dynamics of the global wine industry.


What kind of experience did you have before you began your current role?

I was a national finance director for U.S. Congresswoman, Jan Schakowsky.


Do you have a mission statement or a guiding philosophy for your career?

Work with and get mentored by extraordinary people.


What excites you about the future of your career?

The possibility of building a company that transforms the lives of those who work there and/or are touched by our products.


What do you consider to be your greatest career accomplishment so far?

Perseverance in the face of adversity.


How often do you read outside of work?

Not enough lately, but something daily.


Would you say reading has had a significant impact on your career?

Without question it has. Reading periodicals like The New York Times and the New Yorker pushes me to think bigger, more broadly, and in a global context.

[Similarly], the work I do as a lecturer in management at the Stanford Graduate School of Business helps me to keep a 50,000-foot view on an industry in which I’ve been operating for a decade. [It] has been extraordinarily valuable.


What books do you most frequently gift or recommend to others?

I do love Atlas Shrugged, and my go-to gift otherwise is a moleskin journal for interns to use for capturing their own entrepreneurial thoughts as they leave my organization and continue into their daily life.


Is there one kind of media you consume most regularly as a means of continuing your on-going professional education?

Lately, I have been really enjoying and leveraging on-demand alerts from some of my favorite publications via their apps. I get the breaking news from the New York Times app, I get real-time activity from the MLB app (my husband Hal Morris is director of pro scouting for the Los Angeles Angels), so lately alerts from media apps have been my way of keeping up to date on news in real time.


What role has mentorship had in your professional development?

An enormous role. So much so in fact that I joined the board of Spark Program, a nonprofit organization dedicated to providing mentorship to middle schoolers in San Francisco, Los Angeles, Chicago, and Philadelphia.


Who are your most influential mentors?

There are so many women I admire as mentors, but to name just a few:

My mother Fay Levin who was U.S. ambassador to the Netherlands. [She] has given [countless] speeches about how building a great career doesn’t always have to follow a linear path.

Christie Hefner, whom I met early in my career as a political fundraiser. [She] continues to advise me on an almost quarterly basis on my career objectives and path.

My friend Marissa Mayer who is as extraordinary of a mother as she is a CEO and thoughtful and generous friend.

What has been the biggest challenge you’ve had to overcome in your career so far?

The biggest challenge I faced in my first company, Bottlenotes, was a regulatory shift that rendered our original business model obsolete. I had to make a choice of whether to put up the white flag or pivot our business model and strategy. We chose to pivot and survived as a result.

What have you found to work really well for fostering your own professional growth?

Working out every morning during the work week.

[You can read more about why Alyssa thinks working out is so crucial to her career success in an article she wrote, published by The Secret To Work-Life Balance As An Entrepreneur: Athletics.]


What do you believe has made the greatest contribution to your career successes to date?

Work ethic.


What are a few of your short-term and long-term career goals?

Short-term: build a world-class company.

Long-term: leave an indelible impact on society through acts of service—charitable or otherwise.


Has writing or journaling had an impact your life or career?

I absolutely love writing and journaling. Which in the modern era can simply be digital note taking.

I have jotted down notes/informal business plans for a retail concept my husband and I have been kicking around for years; when we return to the concept, the notes are a great way to revisit ideas already discussed and continue fleshing them out.

The same has held true about ideas for a second idea on wine. Those notes turned into a prospectus. I’ll start shopping it to publishers when I actually have the time to write the manuscript.

I believe writing is incredibly important to finding balance in my life, and I don’t mean writing the obligatory 400 daily emails.


Are you a proponent of learning by doing? Has trial-and-error or experimentation had a place in your professional development?

Yes and yes.

I am a firm believer in using ‘role play’ as a method of preparing for difficult conversations. This trial-and-error approach to preparation was one I first learned as a [graduate] student in courses entitled Managing Growing Enterprises and High-Performance Leadership.

It is amazing how much practicing these conversations- running into potholes in test runs – helps avoid them in the conversation itself. My husband and classmate (Hal Morris) is the person with whom I do this kind of prep on an ongoing basis.


What is the best career advice you’ve ever received?

If you want to build a Fortune 500 company, start by building a Fortune 500 board.


Do you have a regular routine or set of fundamental principles you follow as a conscious way of ensuring you’re always improving yourself as a professional?

I do believe in 360-degree reviews. I used them at my first and second company. They’re not fun, but they’re super useful.


What should ambitious professionals keep in mind in over the years of their career?  

Yes begets yes. Most things in life you get because you work hard, not just because you were lucky or smart.

Taking time to acknowledge a job well done -whether a team lunch, toast, or dinner, whether an excursion or offsite- is extremely important.

We live such busy lives, making sure to treat ourselves with a reward after a job well done is crucial to self-directed gratitude. I say do whatever it is that helps you relax and feel most celebrated- something that is both restorative and gratifying.

I am a big believer in acknowledging birthdays and the wrap-up of a major project or product launch via team gatherings – meals, events, etc. – and major work anniversaries with hand-written cards and meaningful gifts.

These ‘timeouts’ from the standard work day help a team member feel celebrated- and are perfect opportunities for the team to connect outside of the standard work environment or flow.

I also believe heartily in gifts for no reason when someone is really performing. A bottle of wine, a gift certificate, anything that signals ‘thank you for your hard work’ is a great way to inspire it to continue.

Serial Entrepreneurship Alyssa Rapp

You can lean more about the professional development of Alyssa Rapp and other successful women by reading The 5 Professional Development Pillars of Real-Life Career Girls.

Have questions about your own professional development or the details of Alyssa’s career success? 

Ask your questions in the comments below and we’ll be sure to help in anyway we can!

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Brendan Alan Barrett

Brendan Alan Barrett is a top sales producer who has generated millions of dollars in revenue.

In addition to running his own sales organization in the civil engineering and construction industry, Brendan provides coaching and training to sales teams and business owners. His practice focuses on identifying, prioritizing, and winning the attention of prospects that can be turned into sales quickly.

In doing so, Brendan helps his clients to generate revenue and customer testimonials that fuel more scalable and less labor intensive business development efforts for year-over-year growth.

As the founder of and host of The Business of Family and Selling podcast Brendan interviews moms, dads, husbands, and wives who work in sales or run their own businesses. Each interview unpacks the very best in strategies and tactics family-first sellers can use to grow their books of business without losing their status as a rock stars at home.

While originally from the Chicagoland area, Brendan started his sales and marketing career in Southern California before relocating to Arizona.

2 thoughts on “Serial Entrepreneurship | Alyssa Rapp

    • May 15, 2017 at 11:41 pm

      Thanks – Glad you think so!


      – Brendan


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