Scaling as an outsider (w/ CEOs of Calendly, Ellevest & MetricStream) | Masters of Scale Summit '22

From the Masters of Scale Summit stage in 2022, three trailblazing leaders — Sallie Krawcheck, Tope Awotona, and Shellye Archambeau — share their experiences of navigating the challenges of leadership from the perspective of outsiders. In conversation with ‪@RapidResponseShow‬ host Bob Safian, they explore how embracing outsider status can fuel innovation, drive success, and shape distinctive leadership styles. Sallie Krawcheck discusses her journey from Wall Street to founding Ellevest, a financial company built by and for women, highlighting the importance of questioning conventional wisdom. Tope Awotona, founder of Calendly, reflects on how his nontraditional background led him to bootstrap his company into a global success. Shellye Archambeau shares her story of pivoting MetricStream, a failing company, into a market leader, emphasizing the importance of falling in love with the market rather than the product. Together, they provide a compelling discussion on how to leverage outsider thinking to scale businesses and lead effectively in any industry. Chapters: 00:00 Introducing our panel of outsiders 02:10 Sallie Krawcheck’s outsider approach to investing 09:53 Why Tope Awotona leaned into his outsider status 15:59 Shellye Archambeau: Listen like an outsider 22:28 Integrating outsider thinking amongst a team 27:06 The challenges of being an outsider 📫 THE MASTERS OF SCALE NEWSLETTER 35,000+ read our free weekly newsletter packed with insights from the world’s most iconic business leaders. Sign up: https://hubs.la/Q01RPQH-0 🎧 LISTEN TO THE PODCAST Apple Podcasts: https://mastersofscale.com/ApplePodcasts Spotify: https://mastersofscale.com/Spotify 💻 LEARN MORE Our website: https://mastersofscale.com 🚀 JOIN OUR COMMUNITY LinkedIn:   / 11096326   Facebook:   / mastersofscale   Instagram:   / mastersofscale   X/Twitter:   / mastersofscale   TikTok:   / mastersofscale   💡ABOUT US On Masters of Scale, iconic business leaders share lessons and strategies that have helped them grow the world's most fascinating companies. Founders, CEOs, and dynamic innovators (from companies like Uber, Airbnb, Apple, and Disney) join candid conversations about their triumphs and challenges with a set of luminary hosts, including founding host Reid Hoffman — LinkedIn co-founder and Greylock partner. From navigating early prototypes to expanding brands globally, Masters of Scale provides priceless insights to help anyone grow their dream enterprise. #entrepreneur #entrepreneurship #businesslessons #business #businessleadership #mastersofscale #summit #leadership #leadershiplessons #outsider #scalingup #scalingyourbusiness #bobsafian #topeawotona #salliekrawcheck #shellyearchambeau #founder #founderstory