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Peter Drexler: I'm a risk reward guy. Is the reward commensurate with the risk? Some people like to ride motorcycles. For me, it's not worth the risk. If that entails for you, your makeup, like taking nervous risks, going hella skiing, skydiving, riding motorcycles, then so be it. "If long as you're off autopilot and you've thought it through, then that's fine," he says.

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Bill Perkins is one of the world’s most successful hedge fund managers and entrepreneurs, and the author of the bestseller, Die With Zero. In this episode, Bill unpacks the Die With Zero philosophy which challenges conventional thinking related to the balance between health, wealth, and time—the three variables important for fulfillment. Bill makes the case that we should strive for maximum net fulfillment rather than net worth (or even health). He argues that we need to optimize our life to have memorable experiences before it’s too late and that most people are over-saving and under-living. Bill also explains how one can apply the principles in Die With Zero to break out of “autopilot” and optimize their life to achieve maximum net fulfillment.

We discuss:

Bill’s upbringing, background, and first job on Wall Street [3:15];
A missed experience and feeling of regret that shaped Bill’s thinking [14:15];
Thinking in terms of time, and the relationship between money, time, and health [17:00];
Solving for net fulfillment and allocating your time based on the seasons of life [27:15];
How Bill thinks about risk, opportunity costs, and the difference between fear and risk tolerance [35:30];
Optimizing for fulfillment, finding purpose outside of work, and more [41:45];
Thinking about the order of experiences you want to have based on seasons of life [50:00];
Bill’s unique perspective on philanthropy and a more impactful way to give money away [54:45];
Applying the principles in ‘Die With Zero’ to maximize fulfillment [1:04:00];
How to break out of living life on autopilot [1:14:30];
When should your net worth peak? [1:18:00];
Taking calculated risks [1:21:30];
Bill shares a lesson from his incredible birthday [1:25:15];
How Bill’s philosophy has evolved since writing Die With Zero [1:34:00]; and
More.