Upside: Alyssa Rapp

Throughout her career, Alyssa Rapp has not been afraid to ask, Now what? From training as a competitive gymnast to advising startups and running companies, she has always been used to working her tail off and looking ahead. By the time she added parenthood to the list, she quickly discovered the need to “hack” the system – find ways to work more efficiently, productively, and achieving at least episodic balance. Alyssa fell in love with her first entrepreneurial idea while studying at Stanford Business School, and, for the better part of the next decade, ran 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. Alyssa advised startups and private equity-backed companies alike through AJR Ventures; she also taught a course at Stanford’s Graduate School of Business on the Global Dynamics of the Wine Industry. In 2017, Alyssa and her family decided to move to Chicago where, as of 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” and made the list for a second year in a row in 2019. Within the same year the company made the 2019 Top 50 Healthcare Companies and Top 100 Leaders in Healthcare. Alyssa continues to teach at Stanford Business School and has recently been named Adjunct Professor of Entrepreneurship at the University of Chicago’s Booth Business School. She also serves as a gubernatorial appointee to the Illinois Housing Development Authority board. When not immersed in business and civic life, Alyssa loves to run track, do yoga, ski fast, and spend time with her family. Her second book, Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur and Executive was just released last year.