Masters of Scale
Think like an outsider, w/Shellye Archambeau, Ellevest’s Sallie Krawcheck, and Calendly’s Tope Awotona
Aug 22, 2023
Shellye Archambeau, former CEO of MetricStream known for transforming tech firms, joins Sallie Krawcheck, founder of Ellevest and Wall Street pioneer, and Tope Awotona, the founder of Calendly. They explore how to turn challenges into strengths by adopting an outsider's perspective. The conversation dives into the benefits of questioning norms, cultivating diverse teams, and the importance of authenticity in leadership. Their unique journeys provide valuable insights for both emerging entrepreneurs and seasoned executives looking to innovate.
25:16
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Quick takeaways
- Embrace disadvantages and turn them into advantages by focusing on building a great product and serving customers.
- Challenge stereotypes and biases by recognizing underserved markets and building human-centric products.
Deep dives
Thinking Like an Outsider
Tope Aotona, Shelley R. Shambo, and Sally Krawchak, three successful leaders, share their stories of thinking like outsiders and how it propelled their success. Tope, the founder of Calendly, faced challenges being based in Atlanta and having no successful track record as an entrepreneur. He embraced his disadvantages and adopted a freemium business model, a low-cost growth strategy. Sally challenged the financial industry's narrative that women are risk-averse and built Ellevest, a wealth tech company, centered on what women are looking for. Shelley, who grew up as an outsider, learned to embrace her experiences and used her outsider perspective to pivot a failing tech company and turn it into a global market leader.
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