A Journey Through Entrepreneurship: The Story of Apptio's Growth and Transformation

During Madrona's 2024 Annual Meeting, Matt McIlwain and Steve Singh sat down with Sunny Gupta, co-founder & former CEO of @Apptio, to share his remarkable journey in the tech industry. The discussion spans from Sunny's early life in India, his move to the U.S. for education, to the inception, growth, and eventual sale of his startups Performant, iConclude, and Apptio. Key highlights include the strategic decisions and partnerships that led to the acquisition of these companies by major corporations, Apptio's navigation through the challenges of going public, its acquisition by Vista Equity Partners, and Sunny's insights on entrepreneurship, the value of long-term investment, and the future of tech companies in both private and public markets. Read more about Madrona's long-term commitment to our founders here: https://www.madrona.com/madrona-long-term-venture-investing/ 00:00 Introduction 02:07 Sunny Gupta's Journey from India to the U.S. 04:18 The Founding of iConclude and Lessons in Fundraising 08:02 The Birth of Apptio and the Power of SaaS 13:16 Creating a New Category: The Rise of TBM 16:07 The Challenges and Triumphs of Going Public 21:32 The Transition to Private Equity with Vista 25:44 Future Perspectives and Advice for Entrepreneurs 30:56 Madrona's influence