In this episode, we talk to Bob Kelly, one of the few people in the world who has worked with all three CEOs of Microsoft, but he’s also a renaissance man, venture capitalist, marketer, and most importantly, family man.

Bob shared his natural gift of storytelling to walk us thought the early days of Microsoft, detailing the many wins (and few missteps) of the tech giant. Later, we follow him as he makes his way into the world of venture capitalism, and he provides a few tips on how to navigate the science and art of making a wise investment. Finally, we talk a lot about the future of the technology industry and how the new generation of tech leaders are making an impact.

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(01:20) - Bob's Background (Living in East Coast & Europe, Father’s Antique business)

(08:55) - Free-Flowing Ideas and Education (Educational Excellence & tradition, Shakespeare)

(15:00) - The MRI Leadership Principle (Choosing mercy, MRI in Large Organizations)

(19:37) - The Accidental Career (Marketing for Microsoft, Positioning to Enterprise customers)

(36:43) - Leadership & the Four As (Success & Tradeoffs)

(40:25) - Changes at Microsoft (Stages of Leadership, Open Source, Focusing on Windows)

(50:43) - Customer-focused Approach (Providing Delight, Being available for your team)

(1:07:59) - The Move to Venture Capital (Vital Partnerships at Microsoft, leaving Microsoft)

(1:16:04) - The Art and Science of Investing (Where to invest vs. Navigating Ecosystems, Betting on the person vs. The idea)

(1:25:16) - Feedback and Iterative Loops (Feedback in relation to customer engagement)

(1:28:05) - Taking a Seat on the Board (Shifting strategies, Protecting the investment)

(1:35:00) - The Challenges of Venture Capitalism (addressing the criticism, working with startups)

(1:39:55) - Predicting the Future (Government regulation, Apple in the News, tech and societal impact)

(1:57:26) - A New Generation of Tech Leaders (Gen Z business leaders)

(1:59: 19) - Looking Back on a Career (Wins and Losses, A bright future ahead)

(2:05:26) - Closing thoughts (The Life of a True Challenger)