This week on Slay The Gatekeeper, I sit down with Bill Perkins, investor, author of Die With Zero, and one of the most interesting thinkers on risk, courage, and intentional living.
Bill has spent decades around millionaires, billionaires, and people who take massive bets in life and business. In this conversation, he shares the success pattern he sees over and over again at the top: agency, speed, and the courage to move.
We talk about why ideas fail, how ego keeps people small, and why most adults fear looking foolish more than they fear wasting their entire life. Bill also shares the “minimize regret” framework he uses to make big decisions, the habit ultra-successful people rely on to stay in motion, and why he thinks you should spend money when the memory value is highest, not when your bank account looks the best.
If you’ve ever found yourself stuck, overthinking, or dipping your toe instead of going all in, this conversation is a wake-up call to bet on yourself while you still have time left on the clock.
02:10 The success pattern Bill sees in every millionaire: agency, speed, and action
04:40 Why ideas fail: the people who win are the ones who move
08:05 Toe-dippers vs. all-in people — the courage gap
10:45 Ego risk: the real reason people stay small
14:20 Bill’s “future self” test for making hard decisions
17:55 Starting from zero: what Bill would do at 25 with $500
24:30 Why people secretly love failure (and how it validates their own fear)
33:50 Thinking about death as a tool for intentional living
53:05 Memory dividends: spend money when the value is highest
59:20 The fear of wasting your life vs. the fear of running out of money
About Bill Perkins
Bill Perkins is an investor, entrepreneur, and author best known for his book Die With Zero and his unconventional approach to money, risk, and fulfillment. Nicknamed the “Natural Gas King” and “Cowboy of Wall Street,” Bill built his career trading energy markets and is the founder and managing partner of Skylar Capital.
He’s also backed and built companies across tech and media, including SkyFi and SynMax, and has produced several feature films. Beyond business, Bill is heavily involved in philanthropy and lives in Texas with his wife, Lara, and his daughters, Skye and Brisa.
Connect with Bill:

📱 Instagram: @billperkins
📘 Die With Zero: diewithzerobook.com
🌐 SkyFi: skyfi.com/
Stay connected with me
📧 Contact: courtney@smoothmedia.co
👍 Instagram: @courtlynnjohnson
💼 LinkedIn: Courtney Johnson
🎶 TikTok: @courtney..johnson