Alyssa Rapp: “You were meant for this type of leadership”

I wholeheartedly believe in the power of mentorship. I have never shied away from asking for help and advice at important decision-making junctures in my professional life — and I’m happy to be able to give help and advice to others who ask for it. Simply put, no matter where you are in your career, […]

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I wholeheartedly believe in the power of mentorship. I have never shied away from asking for help and advice at important decision-making junctures in my professional life — and I’m happy to be able to give help and advice to others who ask for it. Simply put, no matter where you are in your career, you don’t need to go it alone.


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 busy women leaders are addressing these new needs, I had the pleasure of interviewing Alyssa Rapp.

Alyssa Rapp was named the CEO of Surgical Solutions by private equity firm Sterling Partners in January 2018 and, within six months, was named one of Crain’s Chicago’s “Notable Women in Health Care” — a title she earned for a second year in a row in 2019. From 2005–2015, Alyssa spent a decade in the Silicon Valley as the founder & CEO of Bottlenotes, Inc., a leading interactive media company in the U.S. wine, craft beer, and artisanal spirit industries. In addition to being an entrepreneur and executive, Alyssa is also a civic leader, a lecturer at Stanford University and University of Chicago business schools, a published author of Leadership and Life Hacks and Hacks for the New World, a wife to 1990 MLB World Series champion Hal Morris, and mom to Audrey (7) and Henriette Morris (5).


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 Solutions in January 2018.

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

As I wrote in the Chicago Daily Herald back in April, the need for healthcare workers to work collaboratively (with the state and federal government, the private sector, and other hospitals) is apparent more than ever in this time of crisis. 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 are able to save.

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? Can you share a story about that?

I wholeheartedly believe in the power of mentorship. I have never shied away from asking for help and advice at important decision-making junctures in my professional life — and I’m happy to be able to give help and advice to others who ask for it. Simply put, no matter where you are in your career, you don’t need to go it alone.

As a mentee, I have benefitted from the deep experience of people who have made a personal funding in my career. I’m lucky to count Marissa Mayer, the iconic Google engineer and former Yahoo! CEO, as one of my dear friends and mentors. When I was faced with the decision about walking in to lead a firm that someone else had founded in an industry brand new to me, Marissa’s guidance was hugely instrumental.

Christie Hefner is one of my most cherished mentors, for several reasons. She’s brilliant, strategic, civically and politically engaged, and extremely knowledgeable about media and business — not to mention a pioneer of women’s rights. When we meet every few months, I share my goals, ask for her input and advice, and benefit from her introductions and feedback. I feel fortunate to count her as one of my mentors, not just because she is a great leader, but also because she is always emotionally available and present when we meet.

Another of my favorite mentors and trusted advisors is one of my professors from business school, Joel Peterson. Whenever I have faced a fork in the road that involved any one of those areas, Joel has delivered sound advice. When I am not in a period of acute decision-making, I check in every six months to keep him informed about how my career is progressing. Most importantly, I let him know how his advice and perspective have impacted my career, as they invariably have for the better. Ultimately, Joel’s advice helped me decide when to exit a professional opportunity, while Christie’s counsel helped me decide to take my current role as CEO. Sometimes it’s not so much about specific advice as it is about having a wise and trusted sounding board to think through an opportunity in the context of one’s career arc and long-term goals. I credit Joel with inspiring me to examine my value system and how it marries (or does not) with that of various business colleagues. I credit Christie with encouraging me to venture into new territory and new industries and stretch myself professionally.

The Covid-19 pandemic has affected nearly every aspect of our lives today. Can you articulate to our readers what are the biggest family related challenges you are facing as a woman business leader during this pandemic?

Hal and I are the proud parents of Audrey (7) and Henriette (5). 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 helpful tool has been creating new/dedicated workspaces for each of them in this sheltering in place era. Creating new workspaces does not have to mean converting a room in your house into the children’s learning center (though that might actually be a good idea if space permits). Creating a designated workspace for your child enables them to think about “going to school” for eLearning in a separate space from where they normally live, eat, and play. This physical separation helped Audrey shift her focus and intention: when she is at her desk, with her Chromebook, workbook, physical books, etc., it is time for “school.”

It also helped Henriette start her eLearning from home with her French School Pre-K class, which toggles between one-hour sessions on Zoom with the entire class, and one-hour independent work sessions/breaks, three times throughout each day. A new “set-up” for eLearning helped literally and figuratively set the stage for the girls to be “going to school” from home. We even have Henriette continue to put on her school uniform. It’s all part of the psychological transition: today is a school day, we go to our desk, it’s time to work. With any luck, we’ll have planted the seeds for middle schoolers with decent study habits (one can pray).

Can you share the biggest work related challenges you are facing as a woman in business 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 over communicating versus under communicating, 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.

In order to maintain transparency and timeliness in order to instill confidence, 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 not more 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 over communicate 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?

While sheltering-at-home requires us all to hunker down to “flatten the curve” of COVID-19 transmission, 15–20 minutes of fresh air and sunshine per day are crucial for our health (vitamin D) and sanity. So, provided you are maintaining a safe social distance and observing rigorous hand washing before and after, COVID-19 can be a great excuse to get outside and learn about one’s immediate surroundings. Our daughters have made it a daily ritual to bike ride with Yoda the Bernedoodle, our dog. They have also picked some bulbs from our garden to observe how they grow indoors. A weekly favorite includes going to our local beach to pick up rocks to paint, thanks to the recommendation of my cousin Jocelyn Stanton, a star educator who has started her own rock family.

Other friends are planting vegetable seeds in their backyards and labeling them to start vegetable gardens; urbanite friends are even cutting off the tops of green onions and potato eyes and planting them in pots to let them grow on their windowsills.

Any excuse to explore our surroundings with a more attentive eye, appreciate what is around us, and to find beauty in the mundane is, well, the perfect way to make lemonade out of lemons in this sheltering-at-home era.

Can you share your strategies about how to stay sane and serene while sheltering in place, or simply staying inside, 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.

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 one can use to effectively offer support to their family and loved ones who are feeling anxious? Can you explain?

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?

My husband Hal knows a thing or two about baseball. So it’s no surprise he instilled in me one of the greatest life lessons of all time: “Until it’s the ninth inning and the third out, keep swinging.” Life will throw you no end of curveballs. That’s what life does. When the ball is spiraling toward you at breakneck pace, it’s normal to feel stunned. You didn’t see it coming. If you did, it wouldn’t be a curveball (or perhaps a slider). The challenging part is to not be reactive when you’re still in shock. To live in that uncertain place for a moment without letting it overtake you. To acknowledge the fear, thank it, and send it on its way. To take a deep breath — then pivot.

You can’t avoid the curveballs.The truth is, I love curveballs, because each one comes with a question: What are you going to do about it? My answer probably won’t surprise you. Keep swinging.

How can our readers follow you online?

Instagram: @alyssajrapp

Twitter: @AlyssaRapp

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

Thank you so much for sharing these important insights. We wish you continued success and good health!

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