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

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!

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

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

Want to hear another episode when I’m drunk and called fans? — Listen to this one, in which I discuss my thoughts on sex as a “doorway to a higher perception,” past experiences with stimulants and psychedelics, how Jocko Willink has influenced my approach to discipline, and much, much more.(Stream below or right-click here to download):

#306: Discipline, Sex, Psychedelics, and More — The Return of Drunk Dialing

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…



  • As an immigrant living in Salt Lake City, Danny asks how he can learn to care less about the expectations of others — especially parents whose plans for his life differ greatly from his own. [05:05]
  • How does one go about building a world-class support system? [15:51]
  • Why the best time to test the waters of entrepreneurship is when you already have a steady paycheck. [19:33]
  • Here’s a little dietary advice from someone on tequila, chocolate chip cookie, bullsh*t caloric surplus mode after a rough couple of weeks. [27:50]
  • Joseph asks how I pick projects — specifically, how do I know what to pull the trigger on and what to let go? [32:01]
  • Who are my “five people?” [42:45]
  • Regina asks how I strike the balance between asking questions to better get to know a guest and asking questions that will be useful and interesting to my listeners. How might someone apply this to their own everyday conversations? [45:06]
  • Simple is usually better than clever. Remember to let silence do the work. [48:14]
  • Are the questions you’re asking too personal, or just too early? [49:35]
  • A brief introvert’s guide to leading conversation and how to get someone to open up without putting them on the spot. [52:13]
  • Conversation is a skill, and the only way to get better is to practice. Just make sure to practice before the big game. [57:03]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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19 Replies to “The Return of Drunk Dialing Q&A: How to Ask Better Questions, Take Better Risks, and More! (#330)”

  1. When and where do you put a call out for people to put their phone numbers for these kinds of calls?!


  2. @Tim,

    I heard you mention TiE and TiE is alive and well here in Austin!

    I’m a charter member, so if you’d like to get involved or hear about our events I can update you.

  3. Enjoyed this drunk dialing episode a lot! Thanks for your mentorship and willingness to connect with fans so openly!

  4. Hey Tim,

    Not sure if you reply to comments here. I’ll give it a shot anyway.

    I was really intrigued to listen by the first two points you said you’d cover – timed perfectly, and coming from the perfect source.

    When you drilled down to the first caller’s needs, he said his focus about how people saw him was more about his family. The clarification you used to get there – namely, asking if he was talking about the prospective customers/marketplace – is exactly where I hoped you would go with that point.

    I am wondering if you could speak a bit to that direction: how would you deal with caring less/not at all about what people think inhibiting your ability to execute?

    Specifically, in my case, I have a burning desire to teach people, I want to start making a difference. What I have experience with, is traveling (a lot), and business (which affords my travel). But, later in life, I want to do something I feel has a much higher purpose, related to personal development and spirituality. I fear the conflict between these things – that I may be branded “the travel guy” or “the business guy” or some other niched aspect of what I have to talk about, and people may not take me seriously or that somehow I will be at a disadvantage when I move on from it.

    I don’t personally feel there’s a conflict, because travel opens up doors for personal and spiritual development, and of course there’s nothing wrong with doing the things that can afford one a life of travel. However, I don’t know that people will be responsive to such a drastic niche change, or if it might turn people off somehow otherwise.

    Maybe it’s irrational, but I’ve done a lot of work/exercises around this, including ones you’ve mentioned, including the “so what” from this podcast, and your other one that you said ultimately led you to taking time off to write the 4 Hour Work Week (where you made 3 columns – worse case scenario things; things to minimize the likelihood; line-by-line what to do to get back to where you are now – then evaluate them on a scale of 1-10). I’ve spent years grappling with this, as I don’t want to risk my (much bigger) future, for something that I am passionate about now, but I haven’t found the thing that has managed to move the needle. I’m starting to force myself to work on it through an accountability system, but it’s clear that I have not yet fully committed to the idea because of this conflict of personal ecology, and it’s also clear that it’s going to take a commitment if it’s going to stand any chance of success.

    This post was a lot longer than I expected it would be, I hope you find it and have the time to help.

    In either case, thank you for what you do. You’re a person I look up to for your accomplishments and attitude.

  5. I’ve been listening to the show for 2 years now, and this is in the top 10 for sure! Great questions and great answers.

    Tim, I’m doing DiSSS on a new skill and now I’m digging into the literature. Do you recommend using speed reading (I’ve never tried it before)? I worry that my mind might not be able to absorb too much information that quickly and I definitely don’t want to waste my time with it then. Thanks in advance! 😊

    1. Honestly I have turned so many people on to you. Was a supporter all along the way of your curiosity, tenacity desire for self mastery and life experimentation.., have to be honest, this series makes me just want to say, ‘grow up.’ For someone who has mentioned family members with history of depression, suicide, mental health issues…I find the… let me sling back some alcohol and get frisky with my ansers,…juvenile and insensitive in its normalization of drinking six tequila shots and then starting the show?!

      Your professional life seems above it, but honestly lost

      some respect for me… not that you care.. im sure your rating are great for this kind of thing.

  6. Hi Tim,

    I have appreciated listening to your array of perspectives on so many important topics in life and business.

    My question is based on the first caller who was struggling to pull the trigger in regards to entrepreneurship. I have been connected with an amazing group of business mentors who have their hands on eccomerce and mentorship platforms, and I wanted to connect with the intial caller.

    I’m not sure if this is something you can arrange based on confidentiality, but thought it was worth the ask, to be able to add value to him (I believe his name was Danny).

    Thanks for taking the time to respond!

  7. I just listened to your podcast this morning on my way to work..reminded me of the drunk history Netflix show my daughter made me watch talking about history while getting wasted, which I loved!!! \_/* cheers lechim salute \_/*

  8. Hey Tim! My question is not directly related to this episode, just something that occurred to me while listening. I would love to hear about your experience dealing with difficult and/or overwhelming emotions. Naturally, the ups of life are balanced with the downs, and during those lows, how do you cope? Do you ever experience an emotion so strongly that it paralyzes you? Not so much that you can’t physically move or take action, but that you just can’t shake it? I have this experience with anxiety sometimes, where it will just grip me, viscerally, and my logical brain is like “relax, everything is fine,” but the emotion and the physical feelings persist, until they’re ready to go. Sometimes I can interrupt them, sometimes I can’t. Do you ever get to those lows where a relatively hopeless “f*ck it” mentality sets in, and you just binge out on Netflix or something? You mentioned in this episode that you’d had a rough couple weeks preceding it, and I guess I’m just asking for you to talk about that. What do you do when maybe your best performance, or sharpest mind, or motivation is just not available? This got long, oops. Thanks for everything. 🙂

  9. Some thoughts on your recent 5 bullet Friday:

    I was a huge advocate for oil of oregano and used it as a preventative measure when traveling on planes. However, I have since stopped after reading about possible deleterious effects on gut microbiome. Any thoughts?

  10. Hi one the comments was it may be a great fit to be #2/ liueutenant to an established leader and still make significant progress in your career/ earnings. How does one get those opportunities? I know it is not cookie cutter method to find those situations but how does one start when you already are in late 40s?

  11. @tim Enjoyed this drunk dialing episode a lot! Thanks for your mentorship and willingness to connect with fans so openly!

  12. Hi Tim, first I would like to suggest something which should help you record calls at a much higher quality. A few days ago, I listened to episode #330 and it struck me: you may not know this trick because if you did, you would have used it, so here is step by step instructions how to:

    1. Go to and use your Google account

    2. Enter zip code to search available numbers and choose one

    3. Pair your personal phone number with the available Google Voice number

    4. I am sure you already have a high-quality mic for your computer, but I use a Blue Yeti USB mic

    5. Connect headphones to mic

    6. When you’re ready to make a call, enter the number and select Hangouts

    7. To record call, I use Snagit and capture the Hangouts window

    Et Voila, you now have access to very high-quality call recording tool you can use for your podcasts and you don’t have to share personal phone number with anyone.

    Second, I would like to ask a question: Let’s assume I have an industry disruptive idea I’d like to brainstorm and fund. How do I open the subject with anyone about the idea without worrying it will be taken and used by the audience with resources? Thank you

  13. Tim, similar to the Mike Shinoda episode I’d like to ask if you’d consider an episode with Mike Posner — given that he has launched a podcast of his own he’s come to truly appreciate what you do on a whole new level. As part of his team I’m reaching out to set up an interview between the two of you. I know you’re insane busy but a closed mouth doesn’t get fed so i’m going to make for the proposal. Thanks for taking the time to read this if you did — it means a great deal. Also, thanks for introducing the world to Cal Fussman because of that I now get the chance to work with Cal on his podcast everyday.