#330: The Return of Drunk Dialing Q&A: How to Ask Better Questions, Take Better Risks, and More!

#330: The Return of Drunk Dialing Q&A: How to Ask Better Questions, Take Better Risks, and More!

This episode is a rare exception to the rule — unlike my usual long-form interviews, this is a drunk-dialing Q&A with you guys, which I’ve done a few times in the last few years, including for the celebration of the 100th episode of this podcast. In preparation for this episode, I solicited phone numbers from listeners who wanted to receive a call from me, and then I started drinking and dialing, answering questions and getting a little frisky along the way.

This time, I came in hot, starting after a few preliminary drinks with friends on a weekend — so it's double trouble.

I ended up covering topics including:

  • How to reassess existing projects, specifically ones which you've put a lot of capital and time into, using 80/20 analysis and other tools.
  • How to learn to care less about what people think, social perception, and how to minimize herd mentality.
  • A framework for thinking about entrepreneurship, risk-taking, and how to cut your teeth as a business builder or creator.
  • How to learn to ask better questions, whether in dating or sales.
  • How to let the silence do the work.
  • And so much more!

Please enjoy this tequila-fueled Q&A!

This episode is brought to you by LinkedIn and its job recruitment platform, which offers a smarter system for the hiring process. If you've ever hired anyone (or attempted to), you know finding the right people can be difficult. If you don't have a direct referral from someone you trust, you're left to use job boards that don't offer any real-world networking approach.

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This podcast is also brought to you by 99designs, the world’s largest marketplace of graphic designers. I have used them for years to create some amazing designs. Whether your business needs a logo, website design, business card, or anything you can imagine, check out 99designs.

I used them to rapid prototype the cover for The Tao of Seneca, and I’ve also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you’re happy with or your money back. Click this link and get a free $99 upgrade.

***

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For show notes and past guests, please visit tim.blog/podcast.

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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.

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Avsnitt(867)

#839: Dr. Fei-Fei Li, The Godmother of AI — Asking Audacious Questions, Civilizational Technology, and Finding Your North Star

#839: Dr. Fei-Fei Li, The Godmother of AI — Asking Audacious Questions, Civilizational Technology, and Finding Your North Star

Dr. Fei-Fei Li (@drfeifei) is the inaugural Sequoia Professor in the Computer Science Department at Stanford University, a founding co-director of Stanford’s Human-Centered AI Institute, and the co-fo...

9 Dec 20251h 18min

#838: The Random Show — The 2–2–2 Rule, The Future of AI, Bioelectric Medicine, Surviving Modern Dating, The Promises of DORAs for Alzheimer’s, and Wisdom from Anthony de Mello

#838: The Random Show — The 2–2–2 Rule, The Future of AI, Bioelectric Medicine, Surviving Modern Dating, The Promises of DORAs for Alzheimer’s, and Wisdom from Anthony de Mello

Welcome to another wide-ranging "Random Show" episode that I recorded with my close friend Kevin Rose (digg.com)!This episode is brought to you by:Qlosi prescription eye drop used to treat age-related...

3 Dec 20251h 51min

#837: How to Simplify Your Life in 2026 — New Tips from Derek Sivers, Seth Godin, and Martha Beck

#837: How to Simplify Your Life in 2026 — New Tips from Derek Sivers, Seth Godin, and Martha Beck

As we head into the new year, many of us feel like we’re drowning in invisible complexity. So I wanted to hit pause and ask a simple question: What are 1-3 decisions that could dramatically simplify m...

26 Nov 202532min

#836: The 4-Hour Workweek Principles — 13 Mistakes to Avoid, The Art of Mini-Retirements, and Navigating the Dizziness of Freedom

#836: The 4-Hour Workweek Principles — 13 Mistakes to Avoid, The Art of Mini-Retirements, and Navigating the Dizziness of Freedom

This time around, we have a bit of a different format, featuring the book that started it all for me, The 4-Hour Workweek. Readers and listeners often ask me what I would change or update, but an equa...

19 Nov 20251h 37min

#835: Ben Patrick (KneesOverToesGuy) — 20-Minute Workouts That Produce Wild Results, From Chronic Knee Pain to Dunking Basketballs, Lessons from Charles Poliquin, Bulletproofing the Lower Body, and More

#835: Ben Patrick (KneesOverToesGuy) — 20-Minute Workouts That Produce Wild Results, From Chronic Knee Pain to Dunking Basketballs, Lessons from Charles Poliquin, Bulletproofing the Lower Body, and More

Ben Patrick, better known as “Kneesovertoesguy” (@kneesovertoesguy), is the founder of Athletic Truth Group (ATG), an online and brick-and-mortar training system rooted in rehabilitative strength and ...

12 Nov 20251h 37min

#834: David Baszucki, Co-Founder of Roblox — The Path to 150M+ Daily Users, Critical Business Decisions, Ketogenic Therapy for Brain Health, Daily Routines, The Roblox Economy, and More

#834: David Baszucki, Co-Founder of Roblox — The Path to 150M+ Daily Users, Critical Business Decisions, Ketogenic Therapy for Brain Health, Daily Routines, The Roblox Economy, and More

David Baszucki is the founder and CEO of Roblox. TIME named Roblox one of the “100 Most Influential Companies,” and it has been recognized by Fast Company for innovation on their “Most Innovative Comp...

5 Nov 20251h 55min

#833: Jack Canfield — Selling 600+ Million Books, Success Principles, and How He Made The 4-Hour Workweek Happen

#833: Jack Canfield — Selling 600+ Million Books, Success Principles, and How He Made The 4-Hour Workweek Happen

Jack Canfield is the coauthor of more than two hundred books, including, The Success Principles™: How to Get from Where You Are to Where You Want to Be and the Chicken Soup for the Soul® series, which...

29 Okt 20251h 37min

#832: The Return of The Lion Tracker — Boyd Varty on The Wild Man Within, Nature’s Hidden Wisdom, and How to Feel Fully Alive

#832: The Return of The Lion Tracker — Boyd Varty on The Wild Man Within, Nature’s Hidden Wisdom, and How to Feel Fully Alive

Boyd Varty is the founder of Track Your Life, which offers a limited number of premium retreats in South Africa’s bushveld, and author of one of my favorite books, The Lion Tracker’s Guide to Life. As...

22 Okt 20252h 2min

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