38: Navigating Entrepreneurship: Insights from Jai Shekhawat's Journey

The Indian American Experience Podcast

Jai Shekhawat is the Chairman, Technology Advisory Board, Madison Dearborn Partners, LLC. He was the Founder and former CEO of SAP Fieldglass, maker of the world’s most widely used Cloud platform for the procurement of contract labor and services. Under his leadership, the Fieldglass platform grew globally with users in 120 countries, multiple languages and currencies and over $50 billion in annual spend. Fieldglass was acquired by SAP in 2014.
He is Ernst &Young’s 2012 Midwest “Entrepreneur of the Year” as well as a recipient of the Peter Yessne Staffing Innovator Award, recognized for pioneering the Vendor Management Software space. Jai has held various civic and board positions including serving on the Mayor’s Council of Technology Advisors (MCTA) for the City of Chicago, the Membership Committee of the Economic Club of Chicago and the board of TiE Midwest. He serves on the boards of FourKites, Fleet Complete, BlueCat Networks, HealthEngine and SomruS. He also serves on the Board of Trustees of the Field Museum of Chicago, the Harris Theater for Music and Dance and 1871, one of the largest technology incubators in the world. He is an Advisor to Madison Dearborn Partners, Starvest Partners and Chicago Ventures. He is a founding member of the Firestarter Fund, which mentors and invests in Chicago start-ups.
More about Jai at https://bit.ly/Jai-Shekhawat-LinkedIn
In this special episode, one of my previous guests, Suren Pai, who the regular listeners must have listened to in Episode 30 of this podcast, agreed to my request to co-host, leading to a remarkably engaging, informative, inspiring and valuable account of the tenets of entrepreneurship, the guiding principles of a fulfilled life, and also an eloquent take on parenting.
Jai shares his journey from his early days in a military family in India to his success in the tech industry in the U.S. recalling his transition from corporate roles to entrepreneurship, highlighting the challenges, key decisions, and philosophies that guided him. He reflects on the importance of addressing substantial, recurring problems, and building a purposeful culture within startups. After Fieldglass was acquired by SAP, he embraced a 'portfolio life,' involving philanthropy, investments, and civic engagements. His insights on balancing professional and personal growth, as well as his advice on parenting and community involvement, provide valuable lessons for aspiring entrepreneurs and leaders.
Connect with our Guest Interviewer Suren Pai: LinkedIn/in/SurenPai
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