What does it take to scale a company from an idea to a $13B industry leader? In my latest episode, Okta CEO Todd McKinnon dives into the essential lessons he’s learned on high-stakes decision-making, managing up to the board, and competing against tech giants like Microsoft.

Todd also reflects on his journey to founding Okta, his bold choice to team up with a co-founder he hardly knew, and the motivations that have fueled him for over seven years as a public company CEO. Some key takeaways…

[0:00] Intro[0:33] Todd McKinnon's Early Career and Founding Okta[1:38] Challenges and Psychological Shifts in Leadership[2:49] Decision Making and Company Culture[6:10] Milestones and Early Successes[18:03] The Importance of Market Timing[30:34] Hiring and Building a Strong Team[39:22] Setting Expectations with Board Members[40:50] The Shift in Board Dynamics[41:41] Maintaining Context and Strategic Input[43:15] Navigating Public Company Governance[45:21] Trusting Instincts and Founder Mode[47:11] Breaking Out of the Echo Chamber[51:00] The Importance of Prioritization[53:05] The Loneliness of Innovation[1:05:33] The Role of a CEO in Decision Making[1:18:17] The Journey to IPO and Beyond

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing and editing: Sam Dewees and JR Bohannon

Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA

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About the Show

Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.