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

It is also no secret that entrepreneurs are capable of adapting with lightning speed, pivoting strategies as needed, and frankly doing whatever it takes to survive. For this reason, Covid-19 might provide the greatest opportunity for economic disruption to start-ups across America, greater than they have ever seen — and greater than they might ever […]

It is also no secret that entrepreneurs are capable of adapting with lightning speed, pivoting strategies as needed, and frankly doing whatever it takes to survive. For this reason, Covid-19 might provide the greatest opportunity for economic disruption to start-ups across America, greater than they have ever seen — and greater than they might ever see again. As businesses are essentially forced to stop their races dead in their tracks, everyone will have to return to the starting blocks post Covid-19.


As part of my series about the “How Business Leaders Plan To Rebuild In The Post COVID Economy”, 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 named one of the Top 100 Healthcare Leaders by the International Forum on Advancements in Healthcare in 2019. In February 2020, Alyssa helped shepherd a transaction of Surgical Solutions to a private equity-backed, global strategic player in the healthcare services space, Grupo Vitalmex. Alyssa was retained by Grupo Vitalmex as the CEO of the Company’s U.S. Subsidiary post-transaction. Starting in 2014, Alyssa joined the ranks as a lecturer-in-management at Stanford University’s Graduate School of Business. She was also named an Adjunct Professor of Entrepreneurship at the University of Chicago’s Booth Business School, commencing April 2020, to create and 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 shifted to primarily angel/seed stage investing. 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 March 2020, Governor Rauner’s Successor, Governor JB Pritzker, appointed Alyssa to the Illinois Humanities Council. 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. In May 2020, Alyssa offered a companion edition, Hacks for the New World: How to LIve and Lead in the Age of Sheltering at Home- and Beyond. 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 your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

After graduating from Stanford Business School, I spent the better part of the decade running an e-commerce company called Bottlenotes. In 2008, due to a major regulatory shift, Bottlenotes pivoted, transforming into a leading digital media company for 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 my husband Hal and I decided to move home to Chicago with our two little girls to be closer to our families. I had thoroughly enjoyed my advisory work with private equity firms in the AJR Ventures years; as such, as I thought about transitioning back to CEO life in concert with our geographic move, 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.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

In one of my first hospital site visits, I showed up right from a red eye, in high heels and with a roller bag in tow. I did not realize that I would be donning full scrubs and would need to shove my roller bag into the lockers in the changing room for the women nurses/doctors. I learned to (a) ask for a detailed agenda for my field visits prior to my arrival to arrive better equipped (+ sneakers, — roller bag, etc.) AND to be patient with myself as I learned a brand new industry.

Is there a particular book that you read, or podcast you listened to, that really helped you in your career? Can you explain?

Yes! There is even a reading list at the end of my book, Leadership and Life Hacks!

The reading list is:

Atlas Shrugged by Ayn Rand

Becoming by Michelle Obama

Fair Game by Valerie Plame Wilson

Finding My Voice by Valerie Jarrett

From the Ground Up by Howard Schultz

My Life So Far by Jane Fonda

Open: An Autobiography by Andre Agassi

The Algebra of Happiness by Scott Galloway

The First 90 Days by Michael Watkins

The Jewelers’ Jeweler by Oscar Heyman, Yvonne Markowitz, and Elizabet Hamiltoin

You’re in Charge, Now What? The 8 Point Plan by Thomas Neff and James Citrin

Extensive research suggests that “purpose driven business” are more successful in many areas. When you started your company what was your vision, your purpose?

Do you have a “number one principle” that guides you through the ups and downs of running a business?

Be honest, be direct, be transparent, and work your tail off.

Thank you for all that. The Covid-19 pandemic has affected nearly every aspect of our lives today. For the benefit of empowering our readers, can you share with our readers a few of the personal and family related challenges you faced during this crisis? Can you share what you’ve done to address those challenges?

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.

Life Hack #1 during the Sheltering at Home Era for us has been “Create new workspaces for our children.” as I discuss in my brand new book, Hacks for the New World: How to Live and work in the Age of Sheltering-at-Home and Beyond.

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 desk new to her, with a computer screen new to her, and a new “set-up” for eLearning helped literally and figuratively set the stage for the girls to be “going to school” from. 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).

When the girls take breaks for snacks, lunch, or kinetic wellness (KW), they leave their workspaces for a physical and mental break from their academic subjects.

[P.S. For kinetic wellness — formerly known as physical education or P.E. — we either follow the school’s routine of jumping jacks/pushups/sit-ups/etc., or DIY with a 20-minute light treadmill workout, DIY obstacle course inside or outside, or 20-minute outdoor bike ride. Physical movement is crucial to keeping the girls focused, just like it is for adults, needless to say.]

Creating new physical spaces for Audrey and Henriette’s eLearning has helped us all set up new routines for success.

Can you share a few of the biggest work related challenges you are facing during this pandemic? Can you share what you’ve done to address those challenges?

We as a firm have 200+ frontline healthcare workers operating in 30 hospitals in 9 states. Many experiences the natural fears of entering those hospitals as Covid-19 was on the first rise, especially our 70 team members in the eye of the storm in New York City. Others had equally natural fears about how their income would be impacted as they watched elective surgery volumes drop.

Fortunately, 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 undercommunicating (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) companywide 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 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 overcommunicate versus undercommunicate through the same channels as we eventually pull out of this crisis, perhaps becoming even busier than we were before.

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. What are a few ideas that you have used to offer support to your family and loved ones who were feeling anxious? Can you explain?

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.

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.

Obviously we can’t know for certain what the Post-Covid economy will look like. But we can of course try our best to be prepared. We can reasonably assume that the Post-Covid economy will be a trying time for many people across the globe. Yet at the same time the Post-Covid growth can be a time of opportunity. Can you share a few of the opportunities that you anticipate in the Post-Covid economy?

In my new book, Hacks for the New World: How to Live and Work in the Age of Sheltering-at-Home — and Beyond, I included the following Leadership Hack #5: Think and act entrepreneurially.

There is no question in my mind that there will be great winners and great losers in businesses as a result of Covid-19. The tourism industry will take a long time to rebound. Medical supply companies stand to be big winners, as do on-demand athletic companies like Peloton and ecommerce giants like Amazon. And there are countless in between.

It is also no secret that entrepreneurs are capable of adapting with lightning speed, pivoting strategies as needed, and frankly doing whatever it takes to survive. For this reason, Covid-19 might provide the greatest opportunity for economic disruption to start-ups across America, greater than they have ever seen — and greater than they might ever see again. As businesses are essentially forced to stop their races dead in their tracks, everyone will have to return to the starting blocks post Covid-19.

With this unanticipated global economic reset, the fastest, speediest, and hungriest to win have the fastest starts out of the starting blocks. To quote Abdul Sillah, while it is not how you start a race but how you finish it that determines greatness, those start-ups that are nimble, agile, and speedy will have an unprecedented opportunity to get going and get going quickly — provided their unique solution to a problem is relevant and vital during the age of Covid-19. They will certainly have an opportunity to battle the greats faster and more furiously than they would have otherwise.

So if you are an established organization, it’s time to think entrepreneurially in order to stay afloat and thrive during and post Covid-19. And if you are an entrepreneur: lace up, prepare, and get ready to fly. This could be your time.

Considering the potential challenges and opportunities in the Post-Covid economy, what do you personally plan to do to rebuild and grow your business or organization in the Post-Covid Economy?

Seeking episodic versus daily balance might be the most important hack to me personally in Leadership and Life Hacks. But I have found that its application to business life is even more relevant when coping with Covid-19.

This is not a time when we can seek perfect balance, or daily balance, in our work lives. Our frontline healthcare workers are putting in 14-to-20-hour days to address this crisis. For HR teams managing their teams through these crises, it’s the same story. My endless gratitude goes out to both of these groups on my own team. I’m sure all other healthcare CEOs would agree.

Similarly, what would you encourage others to do?

This is a perfect time to retool strategic plans. Found time can be used to turbo-charge digital lead generation activities; dust off a strategic initiative that had been previously shelved and turn it into a go-to-market plan more quickly than anticipated. It can be a time to explore partnerships that were previously not top-priority, leverage team members capable of X for Y, and so much more. As the adage goes, necessity is the mother of invention. And there is no question that Covid-19 has created the necessity for most small- and medium-size businesses in America to retool their strategic plans.

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

To quote my dear friend and now world-famous athletic coach, Abdul Sillah, “Start strong, finish stronger.” Such is true in athletics and in life. It’s not how you start a race that matters, but how you finish it.

How can our readers further follow your work?

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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