Community//

“Celebrate the wins with arms held high.” With Penny Bauder & Alyssa Rapp

These are strange times. It’s a roller coaster ride — like so much of life. The best lesson I have learned on any roller coaster ride is to buckle up and try to take the peaks and valleys in stride. The Covid-19 pandemic has affected nearly every aspect of our lives today. Many of us […]

These are strange times. It’s a roller coaster ride — like so much of life. The best lesson I have learned on any roller coaster ride is to buckle up and try to take the peaks and valleys in stride.


The Covid-19 pandemic has affected nearly every aspect of our lives today. Many of us now have new challenges that come with working from home, homeschooling, and sheltering in place.

As a part of my series about how women leaders in tech and STEM are addressing these new needs, I had the pleasure of interviewing Alyssa Rapp.

As of January 2018, Alyssa was named the CEO of Surgical Solutions by private equity firm Sterling Partners. Within six months, she was named one of Crain’s Chicago’s “Notable Women in Health Care” (June 2018), and made the list for a second year in a row in 2019. She was also been named one of the Top 100 Healthcare Leaders by the International Forum on Advancements in Healthcare in 2019. In February 2020, Alyssa successfully completed a transaction of Surgical Solutions to a private equity-backed, global strategic player in the healthcare services space. Alyssa was retained by the buyer as the CEO of the Company’s U.S. Subsidiary concurrently in February 2020.

Starting in 2014, Alyssa joined the ranks as a lecturer-in-management at Stanford University’s Graduate School of Business teaching a sold-out class annually on the Dynamics of the Global Wine Industry. She was also named an Adjunct Professor of Entrepreneurship at the University of Chicago’s Booth Business School, commencing April 2020, to teach a course on Women as CEOs, Investors, Directors, and Executives.

From 2005–2015, Alyssa served as the founder & CEO of Bottlenotes, Inc., the leading interactive media company in the U.S. wine, craft beer, and artisanal spirit industries. During the Bottlenotes years, Alyssa was named one of Inc. Magazine’s “30 Under 30” coolest entrepreneurs in America (September 2008) and routinely one of the wine industry’s top 25 of 100 most influential people by Intowine.com (2012 onward). Bottlenotes also received the “Best Advertising and Marketing Company” and the “People’s Choice Award” at the Empact 100 in September 2013 at the United Nations, honoring the top 100 companies with founders under 35.

Starting in 2015, Alyssa also served as the Managing Partner at AJR Ventures, a strategic advisory firm for Fortune 500, $500MM+ privately-held companies, and private equity firms on their new business unit/new market development, digital and e-commerce strategies. As of 2018, her activities via AJR Ventures are primarily angel investing/seed stage investing in nature.

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 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.

Alyssa was honored to have been appointed by Illinois Governor Bruce Rauner in 2015 to serve a four-year term on the board of directors of the Illinois Housing Development Authority. She served on the organization’s audit committee during her tenure, auditing $1B of assets and $100MM operating expenses in partnership with KPMG.

In November 2019, ForbesBooks released Alyssa’s second book entitled Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur, and Executive. It hit the Amazon bestseller list in business management in January 2020.

When not immersed in business and civic life, Alyssa loves to Peloton, 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 and current partner at X10 Capital, Hal Morris. Alyssa and Hal are the proud parents of Audrey Margaret Morris and Henriette Daniella Morris.


Thank you so much for doing this with us! Before we dig in, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

After graduating from Stanford Business School, I spent the better part of the decade running an e-commerce business called Bottlenotes. Partway through the journey, Bottlenotes pivoted, transforming into a leading digital media company in the US wine industry. From 2015–2017, I advised startups and private equity-backed companies alike through AJR Ventures and also taught a course at Stanford’s Graduate School of Business on the Global Dynamics of the Wine Industry.

In 2017, my father-in-law passed away unexpectedly, and we decided to move to Chicago (we’re both from the Midwest and wanted to be closer to our families). I knew that I didn’t want to create something from scratch at that moment. A startup is like a baby, and I already had two human babies — I wasn’t ready for a third. As I thought about how to transition back to CEO life, I started having conversations with several private equity firms in Chicago. Those conversations eventually led me to Sterling Partners, a private equity firm in Chicago who named me CEO of Surgical Solution in January 2018.

Are you working on any exciting new projects now? How do you think that will help people?

In this time of crisis, the need for healthcare workers to work collaboratively is apparent more than ever — with the state and federal government, with the private sector and with other hospitals. Over the past two years, I’ve worked to help hospitals across the Midwest to coordinate resources more efficiently, and I know there are important synergies and efficiencies we can harvest if we join the dots in our regional health system. That might mean sharing scarce ventilators, masks or swabs; it might mean sharing nurses, support staff or simply knowledge. Ultimately, how well we work together will determine how many lives we’re able to save.

Ok, thank you for all that. Now let’s move to the main focus of our interview. The Covid-19 pandemic has affected nearly every aspect of our lives today. Can you articulate to our readers the biggest family related challenges you are facing as a woman in STEM during this pandemic?

Hal and I are the proud parents of Audrey (seven) and Henriette (five). They are opposites in hair color, personality, and style. They are classic sisters: bimodal in their relationship, loving each other/playing beautifully — or fighting like cats and dogs. Calm stasis is the least frequent setting on their shared channel. Surviving/managing life with your eager young learners who are now forced to also “work from home,” instead of bounding off to school with their friends and teachers, is an unprecedented challenge.

Can you share what you’ve done to address those challenges?

One of my favorite leadership hacks from Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur and Executive is Life Hack #94: Schedule everything. We have found that this leadership hack applied to home life has helped us in the first weeks of eLearning/sheltering-at-home.

As it relates to our girls, we have found they thrive with standard daily routines more than down-to-the-minute schedules. In these days of eLearning, we’ve set up new routines. So far, we have kept consistent with some of our “normal” routines already in place: start each day with coloring/stickering/painting/playing in the kitchen while I make breakfast, followed by them getting ready for the day while I work out, followed by a transition to “school.”

That transition involves:

(1) Preparing for the day’s eLearning activities by printing all required documents for that day, pulling up each required platform or application in the browser so the kid can navigate there with a simple “click,” and ensuring all materials required for any non-computer/non-paper assignments (e.g., science experiments, Spanish flashcards, board games) are out and ready to be used that day;

(2) Having the child go to her new dedicated eLearning workspace at roughly the same time each day (8:45 am in our world).

Can you share with our readers what are the biggest work related challenges you are facing as a woman in STEM during this pandemic?

As the days of Covid-19 commenced, I sensed natural fears in our team out in the field. Would their hospitals be impacted to the degree of those in New York City? Would their elective surgeries be cancelled, as had the surgeries at many of the coastal hospitals they’d seen on TV?

Can you share what you’ve done to address those challenges?

We have very good habits and cadence for communicating with our senior leadership team, our field leadership team, and our team as a whole through email, Slack, and as of January 2020, Town Halls.

Those of you who read my first book know I’m a firm believer in the value of overcommunicating versus under communicating (Leadership Hack #42), and this is never truer than in a time of crisis. Hence why we stepped up our game during the days and weeks leading up to the peak of Covid-19:

· HR sent weekly (if not more frequent) company wide emails on the fast-changing federal regulations that would impact (benefit) worker forces like that of Surgical Solutions;

· I personally conducted weekly 30-minute Town Halls open to the entire company for the three weeks in March leading up to the introduction of Federal Benefits (April 1, 2020) to elucidate our strategies and answer any live questions from our team in the field;

· We created a new Slack channel on Covid-19 and encouraged ongoing questions and answers from the team that all could see.

I believe that transparency and timeliness instill confidence, even if the news isn’t ideal. For this reason, I addressed the team live, shared how we were planning to navigate through these choppy waters, and why our business strategy and purpose would be just as valued on the other side of Covid-19, if notmore so.

The responses I received buoyed me. “You were meant for this type of leadership,” one team member wrote. “I cannot thank you enough for having the courage to tell it to us straight, even if the truth isn’t ideal,” wrote another. There is no question in my mind that this was the right approach — and I have every expectation of continuing to overcommunicate versus under communicate through the same channels as we eventually pull out of this crisis, perhaps becoming even busier than we were before.

Can you share your advice about how to best work from home, while balancing the needs of homeschooling or the needs of a family?

One of my favorite hacks from Leadership and Life Hacks is Life Hacks #94: Schedule everything. Let’s call a spade a spade: staying on task while working from home is harder than at an office. There are distractions (e.g., children, dogs, spouses, noises outside your window) and temptations (television on in the background without sound, the snack cupboard being just thirty steps away, etc.). Schedule every call, every individual deliverable that requires a 15-to-60-minute focused work session — everything. By scheduling external and internal meetings, focused time frames to knock out X deliverable, and even breaks, it is far easier to stay on task than when operating in a sea of distraction.

Can you share your strategies about how to stay sane and serene while sheltering in place for long periods with your family?

In Leadership and Life Hacks, I talk about putting on your own oxygen mask first each and every day. In other words, do something to take care of yourself. This holds true as much as ever in the sheltering-at-home age.

Thank goodness for virtual workouts. Whether you are a Peloton devotee (bike/Tread/yoga classes) or can take advantage of your local gym’s online offerings, there is an endless array of athletic content to enjoy digitally. My friend and frequent collaborator Bree Barton is offering her weekly “Rock ’n’ Write” dance/writing class for free on Zoom. Perhaps this is the time to try something new and get out of your comfort zone — all from the comfort of your own home. All you need is motivation.

The tools exist for your athletic life to stay on track — if not thrive — while sheltering-at-home. Heck, even our daughters have started to look forward to almost daily sessions of YogaKids on YouTube and in running at the park or on the treadmill at home. If you weren’t already, the Covid-19 era is the PERFECT TIME to start or continue to do something for yourself daily.

Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty, fear, and loneliness. From your perspective can you help our readers to see the “Light at the End of the Tunnel”? Can you share your “5 Reasons To Be Hopeful During this Corona Crisis”? If you can, please share a story or example for each.

These are strange times. It’s a rollercoaster ride — like so much of life. The best lesson I have learned on any rollercoaster ride is to buckle up and try to take the peaks and valleys in stride.

  1. Celebrate the wins with arms held high.
  2. Breathe through the lows. So long as the coaster stays on the track, you are winning.
  3. To the degree that you can, find ways to enjoy the ride.
  4. Summon valor in the journey.
  5. Discover small tokens of gratitude for the little gifts life is bringing in spite of the madness.

As for stories, I don’t know if I’ve seen a more inspiring and reassuring example of how adaptable humans (especially children) are than watching my daughter Audrey take virtual piano lessons during Covid-19. At first, it simply seemed like she was practicing. Then when the song finished, with a slight turn of the head to the left, she watched her attentive teacher on FaceTime. He corrected pacing, hand placement, and more. I got choked up watching that moment — not because it was as momentous as other parenting moments, but because of the wonder of how adaptable children are. It gave me faith that the power of technology can bridge us through these strange and uncertain times.

My wish for you is that small but bright moments like these can buoy you on this winding journey as much as they have for me.

From your experience, what are a few ideas that we can use to effectively offer support to our family and loved ones who are feeling anxious? Can you explain?

One of my favorite assignments our daughter received this week was to write a letter to a family member. Audrey picked her brand-new baby cousin. She shared with him what is happening in her world currently, and asked about his. Best of all, we were able to work on her spelling and grammar through the process (ha).

Audrey recently had an assignment to write a letter to her new in-class pen pal. She wrote the letter, sharing what eLearning from home has been like for her, then asking what it’s been like for him. We then recorded a video of her reading the letter to share with her pen pal in addition to sending the handwritten letter.

In Leadership and Life Hacks, I shared Hack #83: Write love letters. In the age of Covid-19, we’ve simply adapted this to write more letters, period. Additional ideas could include writing letters to local hospitals to thank the nurses and doctors for their service, or leaving a small Post-It note on your front door for the postal worker, FedEx, or UPS delivery person to say thank you for their ongoing service.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Success in the Covid-19 era in my mind is defined by attitude and effort. Did I give a certain activity my all? Did I give a certain obligation my all? Or did I realize it wasn’t crucial and then chose to leave it on the field? If the answer is yes, then, to quote my great husband Hal, effort is all you can control.

How can our readers follow you online?

Instagram: @alyssajrapp

Twitter: @AlyssaRapp

Facebook: Alyssa Rapp https://www.facebook.com/alyssarapp

The Thrive Global Community welcomes voices from many spheres. We publish pieces written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Learn more or join us as a community member!
Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Alyssa Rapp: “Pivoting strategies as needed” with Charlie Katz

by Charlie Katz
Community//

Female Disruptors: Alyssa Rapp is making the surgical process more efficient

by Erika Couto

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

- MARCUS AURELIUS

We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.