Hacks Newsletter Week 205: Insights from Iconic Leader Christie Hefner


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Insights from Iconic Leader Christie Hefner: “Culture Eats Strategy for Breakfast”

Christie Hefner Guest Lecturer, University of Chicago Booth Business School, January 2024

In this week’s course on Women as Investors, Directors, CEOs and Executives at the University of Chicago’s Booth Business School, we discussed the strategic perils and opportunities in the media industry via the Bonnier News case. This case was paired with a guest lecture from my friend, mentor, and extraordinary CEO and Director, Christie Hefner. Her famous line to me that  “you want to end up Netflix, not Blockbuster.”  The question is of course how? Christie continued, “To do so, you need to create a culture of where the best people want to come to do their best work. If you do this with the right strategy, it will be very hard to fail.”

Christie discussed how to think about new challenges and new opportunities offered by strategic evolution in industries, such as the imperative of print media to evolve into the digital media world. “At Playboy, we recognized that we were not a print publisher, but a multimedia distributor of branded content. I wonder what outcome Sports Illustrated would have had (just this week) if it had thought about itself not as a magazine company but as a deliverer of a specific type of branded content?”

“No matter the industry, the more successful you are, the harder it is to disrupt yourself. Kodak had invented digital film but ‘put it away’ at risk of cannibalizing the print business. But it was put away. “It is easier to disrupt yourself vs. get disrupted by someone else.”

In the end, Christie reminded us that in business you are “either you are growing or you are dying.”  On the most important skills of leaders and teams?  “Communication is key skill -as is writing well- but active listening the most important, and perhaps hardest, skill of all. Hire for intellectual agility.”

You can learn more about Christie and her extraordinary life experience in this recent article, and her extraordinary insights on why the 1st Amendment matters in her Tedx Talk here.

Have friends or family members who would enjoy #HackstheNewsletter? Refer them here.



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There will be no end to the curveballs that life throws. As soon as you feel comfortable, another setback or new challenge will arise. Alyssa Rapp is driven to help people like her—the doers, those who keep swinging—seek to succeed in both life and career. Every challenge is an opportunity, are you making the most of yours?

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