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5 Business Lessons Learned from the “School of Hard Knocks”, with Alyssa J. Rapp

“Speak up about sexism in Silicon Valley when you face it. Gretchen Carlson is my my hero in this regard.”
I had the pleasure of interviewing Alyssa J. Rapp. Alyssa is the Managing Partner at AJR Ventures, a strategic advisory firm for Fortune 500, $100MM+ privately-held companies, and private equity firms on their e-commerce, digital media, social media, and entrepreneurial strategies. Starting in 2014, Alyssa joined the ranks as a lecturer-in-management at Stanford University’s Graduate School of Business teaching a course on the Global Dynamics of the Wine Industry. She was re-appointed to a new three-year term in June 2017.
Alyssa was named in Inc. Magazine’s “30 Under 30” coolest entrepreneurs in America (September 2008)” . She is honored to have been appointed by Illinois Governor Bruce Rauner to serve on the board of the Illinois Housing Development Authority.
When not immersed in business and civic life, Alyssa loves to run track, do yoga, ski fast, and try as hard as possible to decipher a slider from a curve ball from her husband, 1990 MLB World Series champion.

Yitzi: Thank you so much for doing this with us! What is your “backstory”?

I was a childhood athlete (gymnast first- 3 hours/day, 6x/week, from 7–17 years of age), then a serious contemporary dancer (30–40 hours /week 17–21), who channeled her love of athletics and the arts into the sport of politics post-college by serving as Congresswoman Jan Schakowksy’s national finance director. (My claim to fame there was creating the Ultimate Women’s Power Lunch, now in its 15th year, and one that has been adopted by numerous organizations and candidates in the Democratic Party). After 2.5 years in politics, I realized I’d love to go back as the candidate some day- but in the interim, I wanted to make a run at life as an entrepreneur. So off to Stanford Business School I sent, where I met my now-husband, Hal Morris (see bio below). While at the GSB, I started an e-commerce company called Bottlenotes, striving to be the “Netflix for wine.” We enjoyed great early traction when a regulatory shift by the California Alcohol Bureau of Control about “Third-Party Marketing Firms” like ours (temporarily) rendered our business model obsolete. Forced to put up the white flag or pivot, I chose to pivot- and we turned into the leading digital media company for wine, and later, multiple beverage categories, through digital newsletters and large-scale interactive events. Bottlenotes eventually landed with PEAK6 Investments of Chicago. Post-Bottlenotes, I chose to take a couple of years to teach at Stanford Business School and start AJR Ventures, which has served as an advisor to two family offices and two private equity firms in Chicago and the Bay Area. What comes next: time will tell! :-)

AJR Ventures is a strategic advisory firm for Fortune 500, $100MM+ privately-held companies, and private equity firms on their e-commerce, digital media, social media, and entrepreneurial strategies. I help big companies launch new products, expand their digital footprint, and drive revenue and gross margin via e-commerce and omni-channel channels.

Yitzi: Can you share the funniest or most interesting story that happened to you since you began leading your company?

The most interesting aspect of the work we have done at AJR Ventures is how organically the projects have arrived and how beautifully they have “built upon each other.” From business plan creation to e-commerce channel expansion, and much in between, each step has been instructive, fun, flexible, and satisfying- which made it perfect for the past couple years with now 5-year old, and 2.5-year old daughters.

Credit Blanchard Photography

Yitzi: What do you think makes your company stand out? Can you share a story?

When companies are at scale, they are necessarily focused on daily operations and processes to keep a wheel that big turning. It is superbly fun to work with these organizations in bringing an entrepreneurial approach to a division or distribution channel- and to hear the feedback “we have been talking about this for months and didn’t know how to implement it. Thank you!”

Yitzi: None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are?

I am grateful to countless people- but at AJR Ventures, I am particularly grateful to my friend and advisor, Tracy Wan. She was the President of The Sharper Image and Cycle Gear, and her experience and perspective and go-getter attitude are second to none.

Yitzi: How have you used your success to bring goodness to the world?

I think it’s safe to say that every non-profit or civic board that I am on benefits by a) my willingness to always underwrite the wine donations for major fundraising events, and b) my zealousness about their need to iinvest in digital technologies and infrastructure. I also love to “give back” or share a decade+ of hard-knocks experience and relationships to the table as a Lecturer-in-Management at Stanford’s Graduate School of Business.

Yitzi: What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why.

1) Speak up about sexism in Silicon Valley when you face it. (Gretchen Carlson is my my hero in this regard.)

2) Hire as many people with deep domain expertise as early as you can in a start-up

3) Know thy value: investors and board members need you as much as a CEO as you need them

4) It’s not how many great ideas that you have that matters but how well you execute a select few of them.

5) Seek as many great women mentors as you can

Yitzi: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this :-)

I would love to have breakfast with Ariana Huffington now or in the near future. Thrive is an inspiration.