Alyssa Rapp: Hacking Your Life






   “Dictionaries define hacking as cutting off branches or breaking into computers. To me hacking should be thought of as shortcuts, work-arounds or work-throughs so that you will feel confident and empowered.” —Alyssa Rapp, author of Leadership & Life Hacks.



That Winnetka entrepreneur and CEO Alyssa Rapp knows time management skills shone clear as we talked on her ride in from O’Hare to a business meeting this week, with conversations on either side of ours. What most impressed me was her focus, her ability to be totally present in our conversation despite her schedule, showing the “episodic balance” which she practices.

   “One of the best pieces of advice I’ve ever received came from Joel Peterson, my mentor at the Stanford Business School and Chairman of JetBlue, was to look for episodic balance not daily balance.  What it means to me is that there are going to be times I spend a lot of time with my husband and our kids and fill up that well with love and experience and connection. During those times my career takes a backseat. Work doesn’t go away completely but it gets compressed like a toothpaste tube.  And then there are many days when work takes the driver’s seat.  When I fly often weekly for work, day trips are my favorite: taking the 6 am flight out to see a client or potential client, then right back home. You simply can’t serve all the stockholders all the time.”

The New Trier graduate says that she is “scheduled to a T”. “I schedule everything so that I get maximum time out of every day.”


Alyssa Rapp and her daughter Audrey apple picking.

“Time with my girls is sacred.  My husband Hal and I love taking them on adventures to the Brookfield Zoo or cultural spots. If there were 366 days this year, I would use that extra day for a trip to New York to see the ballet or the US Open as we did this year.”


Rapp’s husband Hal with their daughter Henriette.

    “I love being a CEO and am very proud to bring value and impact to my field.  What is the one quality that you need to start a new business?  It is grit, most definitely, and then the ability to work as a part of a team.”

In 2018, Chicago-based private equity firm Sterling Partners hired Rapp to be the CEO of Surgical Solutions, a healthcare services portfolio company with 200 employees. In less than six months in healthcare, Rapp was recognized as a leader in the field. She also serves as the Managing Partner of the strategic advisory firm AJR Ventures serving primarily family offices and private equity firms on their portfolio companies in need of guidance on their e-commerce, digital media, content and AJR Ventures Rapp also makes.

Her own parents taught her much about balance:

    “I always knew I wanted to be a mother because I’d grown up with a world-class mother myself. Former US Ambassador Fay Hartog-Levin, aka Madame Ambassador, taught me many crucial life lessons but perhaps paramount was that family matters. She shows extraordinary dedication to her career, her health and her closest friends. She served as a big-firm attorney, as vice president of external affairs for the Field Museum, as a crisis-management strategist at Res Publica, all before becoming US Ambassador to the Netherlands under President Obama.

   “Her youth had been less than idyllic.  She lost her own mother when she was just 16 and had to apply to college and get herself there on her own.”


Rapp’s daughters holding her book.

We couldn’t wait to learn more from Rapp about hacking.  Leadership & Life Hacks, which comes out on October 29th, reveals not only how to create a terrific new business, lead business teams, and mentor new leaders but also offers insight into entertaining and child rearing.  Rapp will share hacking tips at the Book Stall in Winnetka November 3 at 2 pm as part of the Book Stall Talks Business series.

Here are some of the tips this management and organizational specialist describes in her book to reconcile conflicts between work and home life schedules and responsibilities.


Life Hack 93:  Tape your favorite quote to the bottom of your laptop:

   “That way, every time you pack up your laptop you will feel inspired.  Mine is from my friend Jacki Rigoni, a world-class copywriter and marketer:  “You are one decision away from the life you want.  To me it means that every day is an opportunity to make a small decision to live your best life.”

Life Hack 74:  As long as you know the rules, they can be broken.

   “Once you’ve achieved a certain level of competence, trust your own instincts on how best to break them.”

Life Hack 68:  Multi-tasking is not a choice; it is a necessity.

   “For me, multitasking does not mean writing an email for work while my kids are standing around trying to talk with me.  Multitasking is showing them it’s healthy for me to work out every morning, and ask them if they want to work out, too.  Another was is to enlist your children’s help, letting them invest as co-creators in the time you spend together.”

Rapp also recommends when hosting a party to create ways for children help prep, including doing place cards.

Leadership Hack 45: Clarify what you are looking for in a mentorship.

   “What you have in mind may be totally different that what they have in mind.  Do you want advice or hands-on guidance, encouragement or brainstorming sessions? For a mentorship to thrive you also want to give the mentor what they need.”

And her Life Hack Postscript:  Eat more quinoa–her favorite snack, and a boost of energy for a busy day.


Liza Yntema, founder of the Dance Data Project, described her close friend:

“Alyssa is not just a supremely successful woman, she is an admirable person. She has zero space for pettiness or backbiting, truly helping everyone around her to achieve and be happy. Her daughters are growing up with a marvelous example of ethical leadership, zest for life and a truly wicked sense of humor. She is a shot in the arm and just a ton of fun to be around.”

Alyssa told us about her pivotal moment:

    “When I was 17, I went sea kayaking with Outward Bound near the Boundary Waters of Minnesota.  A fundamental part was of the adventure is ‘solo camping’—24 hours with no food, just water, tarp, some string with which to tie it up, and a plethora of pen and paper. 

   “I put pen to paper to good use.  It was a seminal moment. I realized that my identity as a human being had been wrapped up in being a gymnast, a dancer, a student, a sister and a daughter.  At that point gymnast was most dominant. What I gleamed was I was who I was because of what I was from within.  When I stripped away positive messages from coaches and good grades, the core values would still be there.”    

In 2014, Rapp became a lecturer-in-management at Stanford University’s Graduate School of Business. She 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 in 2005. At Yale, she earned the Frank M. Patterson prize for the best essay on the American political system for her senior thesis on public housing reform in Chicago.

Rapp’s first startup was Bottlenotes, a subscription service based on a wine club concept.

    “After two years at Stanford, I’d come to realize there were three things I loved—Hal, entrepreneurship and wine.  Long before Blue Apron and Plated popularized the subscription model of food and wine at home, we built out ours.  We had a clever twist, zero inventory carrying costs.  Our original model was simple, sending our customers wine tailored to their personal tastes while using technology.”

Rapp loves to ride her Peloton bike, run track, do yoga, ski fast, and try as hard as possible to decipher a slider from a curve ball from her husband, fellow Stanford GSB alum and 1990 MLB World Series champion, Hal Morris.

One of her favorite quotes comes from Alex Toussaint, Peloton’s senior instructor.

   “There’s no elevator to success, everyone’s got to take the stairs.”

Rapp’s hacks definitely will guide you several flights up.