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“Why you should Celebrate the wins with arms held high.” With Beau Henderson & Alyssa Rapp

In this time of crisis, the need for healthcare workers to work collaboratively is more apparent than ever — with the state and federal government, with the private sector and with other hospitals As part of our series about ‘5 Steps That Each Of Us Can Take To Proactively Help Heal Our Country’, I had […]

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In this time of crisis, the need for healthcare workers to work collaboratively is more apparent than ever — with the state and federal government, with the private sector and with other hospitals


As part of our series about ‘5 Steps That Each Of Us Can Take To Proactively Help Heal Our Country’, 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 doing this with us! Before we dig in, our readers would like to get to know you. Can you tell us a bit about how you grew up?

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 , ages 17–21) who went on to study politics and art history at Yale. I then channeled my love of athletics and the arts into the sport of politics post-college by serving as Congresswoman Jan Schakowksy’s national finance director. After 2.5 years in politics, I wanted to make a run at life as an entrepreneur. So off to Stanford Business School I went, where I met my now-husband, Hal Morris. While at the GSB, I started an e-commerce company called Bottlenotes, striving to be the “Netflix for wine,” that ultimately pivoted to become one of the leading digital media companies in the US wine industry. Post-Bottlenotes and following the birth of our second daugher, I chose to take a couple of years to teach at Stanford Business School and start my own advisory firm, AJR. Ventures (2015–2017). Having enjoyed the private equity advisory work I did the most, when Hal and I decided to move back to Chicago (where we both grew up) in 2017, I then ended up being offered the opportunity to take the helm of a private-equity-backed surgical services company called Surgical Solutions, where I still serve as CEO.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Ayn Rand’s Atlas Shrugged, Andre Agasi’s Open, Katherine Graham’s Personal History, are just some of my favorites. I included a more detailed version of my reading list at the end of my my book Leadership and Life Hacks: Insights from a Mom, Wine, Entrepreneur and Executive.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

To quote my great husband Hal, effort is all you can control. And to quote/paraphrase Maya Angelou and Gandhi, “Be the change…”

How do you define “Leadership”? Can you explain what you mean or give an example?

I am a big believer in “walk around management” through direct and indirect observation — a leadership style I learned from my stepfather, Daniel Levin, one of Chicago’s most pioneering real-estate developers. (Dan has led the development of affordable housing and mixed-income housing throughout Chicagoland area for the past fifty years in his role as Founder and Chairman of The Habitat Company.) He also has shown me time and time again that breaking bread matters: When you’re sharing a meal, you’re connecting on a real, human level. Hosting people at your home for dinner can be a way to fast-track relationships built on trust and mutual understanding.

Ok, thank you for all that. Now let’s move to the main focus of our interview. The United States is currently facing a series of unprecedented crises. So many of us see the news and ask how we can help. We’d love to talk about the steps that each of us can take to help heal our county, in our own way. Which particular crisis would you like to discuss with us today? Why does that resonate with you so much?

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?

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.

I’m a firm believer in the value of over communicating 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) 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 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 value proposition would be just as relevant on the other side of Covid-19, if not more so.

Can you tell our readers a bit about your experience either working on this cause or your experience being impacted by it? Can you share a story with us?

In this time of crisis, the need for healthcare workers to work collaboratively is more apparent than ever — with the state and federal government, with the private sector and with other hospitals. Over the past two years, we at Surgical Solutions have worked to help hospitals 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 care systems. 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. Here is the main question of our discussion. Can you please share your “5 Steps That Each Of Us Can Take To Proactively Help Heal Our Country”. Kindly share a story or example for each.

  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.

We are going through a rough period now. Are you optimistic that this issue can eventually be resolved? Can you explain?

As I shared with my inaugural class on Women as CEOs, Entrepreneurs, Investors, Executives & Directors at the University of Chicago Booth School of Business, I have the greatest hope and expectation that the themes of diversity and inclusion, equality will shape young people’s choices and actions. My wish is that my students and their peers are inspired and motivated by the various crises we face now to “be the change” they expect to see in the world (to paraphrase Maya Angelou). I hope that they live and work in — but, more importantly, create — environments where values-based leadership prevail.

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

One of my mentors Valerie Jarrett reminds me often that “the tone starts at the top.” She suggested adding language and clauses to contracts to ensure everyone is treated with respect. Add it to your own employment agreements even if your employers don’t. Start the conversation, at work, in the classroom, in the boardroom. Get commitments to change in writing and hold others (and yourself) accountable.

How can our readers follow you online?

Instagram: @alyssajrapp

Twitter: @AlyssaRapp

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

This was very meaningful, thank you so much. We wish you only continued success on your great work!

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