The Art of Street Performing, Losing 100+ Pounds, and Weaponizing Kindness – Penn Jillette on The Tim Ferriss Show

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Key Takeaways

  • Like Penn, consider keeping a daily journal of each day’s activities
  • Despite what you see on the news, most people are generally good, and the world is safer than ever before
  • Fat is lost in the kitchen, not in the gym. At the beginning of your weight loss journey, to instill this, consider avoiding the gym entirely. 
    • “If you want to really lose body fat for body recomposition, it’s 90%+ diet. You have to prove that to yourself, and a very effective way of doing so is by taking exercise off the table for a short period of time.”Tim Ferriss
  • The faster you lose weight, the more likely you are to keep it off

Books Mentioned


How to Guard Against Deceit & Become More Skeptical (without being cynical)

  • 🎧 “Of the 7 billion people on the planet, if we round it off, about 7 billion are good. I don’t believe in God. I also don’t believe in the existence of evil. I believe there’s very little bad in the world. There are a lot of mistakes, but not people maliciously trying to do bad things.” Penn Jillette
  • Given the above, in general, your chances of coming across someone who’s scamming you are relatively low
    • Penn has a rule of thumb: “If you pick someone, you’re really safe. If they pick you, you have to be careful.” 
      • Said another way: “If random selects or you select, you’re doing okay. If someone selects you, you have to be a little cautious.”
      • For example:
        • If you run up to someone at Starbucks, tell them to take your car because it’s an emergency (and give them your number to contact you later), your vehicle is probably safe
        • “If you go to somebody and say, ‘I want to talk to you about my problems; I want to be friends with you; I want to pour my heart out,’ your chances are pretty good of whoever you talking to being okay. But, if someone comes to you and says, ‘I can help you with your problems, your Spidey sense should tingle.”

Penn’s Journaling Practice

  • Ever since he turned 30, Penn’s kept an extensive daily journal 
  • His system:
    • He first logs the date/time
    • He records the previous 24 hours
    • He writes a brief summary of any recently finished books/movies
    • (All of the above adds up to ~500-1,000 words per day)
  • Every morning, Penn will also set aside time to read his journal entries on that particular date 20, 10, and 1 year ago
  • Penn estimates that the whole process (writing and reading old entries) takes ~20-30 minutes

How Does Penn Benefit from Keeping a Daily Journal

  • Perhaps the biggest: It’s a purge
    • “I find it easy, once I write out what happened the day before, to completely forget it. It just goes away.”Penn Jillette
  • Another side benefit – emotional time travel
    • Penn has a HORRIBLE visual memory, but during his day-to-day, he makes an effort to fully take in the emotions he’s experiencing, so, given a prompt (the journal), he’s able to re-experience whatever scenario caused the feelings to occur

Just How Bad is Penn’s Visual Memory?

  • “Other people can visit stuff in their memories visually fairly easily, but for me, it’s very difficult. I have a conceptual and verbal memory, but no visual memory at all. I can’t rotate objects in space. I can’t recreate any room I’ve been in.” – Penn Jillette
  • After undergoing psychological testing at the University of Chicago (long, long ago), psychologists determined Penn had the “widest spread of intelligence they’d ever seen”
    • Penn adds: “My IQ is so low visually, that I’d be in a halfway house if the rest of my IQ were that way.”
  • Penn once failed to recognize his own mother when she came up to speak with him after a show

Penn’s Period of “Homelessness” & Hitchhiking Across the Country

  • When Penn was 18, influenced by Bob Dylan, he decided to leave home and hitchhike across the country ( 5x width-wise and 4-5x length-wise)
    • He wasn’t homeless by the standard definition – he called his mom & dad every day, and kept some reserve money – but he didn’t have a permanent place to live
  • An interesting thought on hitchhiking:
    • “I still don’t understand why it’s not more common nowadays since the world is safer. I think that, because of information, we think the world is more dangerous, but it’s certainly an order of magnitude safer by any measure than it was when I was hitchhiking, and it was very, very safe then.” Penn Jillette

The Art of Street Performing

  •  During his travels, Penn made money by performing on the street
    • “I would gather a crowd of 300-500 people. The crowd gathering itself would take ~5 minutes, the collection of money would take ~5 minutes, and I’d do 5 minutes in between [of street performing – juggling, comedy, etc.]” – Penn Jillette 
  • Penn had quite the unique approach to gathering a crowd:
    • “I would walk over to three or four people and say, ‘Hi, I’m going to be doing a juggling show here in a few minutes, and it’ll be stupid without a crowd. So, I need to get a crowd here, and I need you to help me get a crowd. So, what we’re going to do is I’m going to do nothing, and then you people cheer and applaud a little bit, even though there’s only four or five of you. Then, other people around will see you and think something’s happening, and they’ll come over here. But, of course, nothing will be happening, and you can turn around and laugh at them. So, this is just going to be kind of a joke we’ll play.’
      • Penn would then repeat the process twice more using the larger crowd that had since surrounded him, resulting in an ever-expanding group of people
  • And to increase donations, Penn would say to the people at the back of his crowds:
    • “You people in the very back row, you didn’t get to see any of the show. I don’t expect any money from you at all. That would be foolish for you to give me money when you haven’t seen the show, but what I do expect you to do is hold hands and let nobody out who hasn’t given me money because they did see the show.”

Penn’s Vagabonding Years Made Him an Expert at De-Escalating Hostility

  • During his hitchhiking days, Penn routinely found himself at rest steps or city corners where he could easily have been beaten to death
    • “I had guns pulled on me, I had knives pulled on me, I was in the worst kind of situations, but it was all okay. I came out of those experiences incredibly trusting of people. I also came out of it incredibly good at de-escalating hostility.” – Penn Jillette
  • Fun fact: Using his “de-escalation skills,” Penn once avoided a diner fight by dumping a milkshake on his head 
  • Of course, Penn has some practical advice:
    • “One of the ways to diffuse a situation is to simply give the other side everything they want… If you don’t fall into the macho trap of having to prove something to a stranger about your intellect, morality, sexuality, or whatever, if those just go away or aren’t important, you’ve diffused 70% of conflicts.” – Penn Jillette

Why Penn Abstains from Drugs & Alcohol

  • There are a few reasons:
    • Penn has an addictive personality, and because of this, thinks they’re best avoided
      • Reflecting on the past: “I didn’t respect moderation. I wanted to be all or nothing on everything. I just thought that if I had one sip of alcohol, I’d be mainlining heroin within a week.” – Penn Jillette
    • “If you move sober through the world, you have this huge advantage… You can make rational decisions, and you don’t have certain parts of your thinking reduced.” – Penn Jillette 
    • “Parents not doing drugs and not drinking is the biggest indicator of offspring not doing drugs and drinking.” – Penn Jillette
      • As you can probably guess, Penn’s parents never drank

Penn’s Insane 100+ Pound Weight Loss

  • At his worst, Penn weighed ~340 lbs.
  • During the peak of his weight loss journey, Penn lost an average of 0.9 pounds per day for 4 months!. Ray Cronise played a considerable role, coaching Penn and having him adhere to the following protocol:
    • Periodic contrast showers
      • Why? – There’s a ton of research showing cold exposures speeds fat loss
    • Diet:
      • During the first two weeks, Penn ate nothing but potatoes
        • Ray’s reasoning: “That’s going to knock you out of your social eating, let you feel what hunger feels like, and let you see what the advertising looks like. All of this will take the blinders away.”
      • Then, Penn added in some beans, chili, rice, vegetables, and salads
      • Four months later, Penn was allowed to eat fruit
      • (Overall, Penn ate at a HUGE calorie deficit – he estimates he was only eating ~600 calories a day)
    • Exercise:
      • None (at least initially), here’s why: Ray believes weight loss and strength training are contradictory, and while dieting to lose weight, you shouldn’t really be exerting yourself
        • Tim adds a relevant point: “You cannot outwork your mouth”
          • People who exercise often compensate by “rewarding: themselves with ~10x the number of calories they would have burned in a given workout
          • 🎧 “If you want to really lose body fat for body recomposition, it’s 90%+ diet. You have to prove that to yourself, and a very effective way of doing so is by taking exercise off the table for a short period of time.” Tim Ferriss
  • Penn adds:
    • Most people gain back their weight within 2 years; what helps keep it off? – The speed of the weight loss
      • “The faster you lose the weight, the more likely you are to keep it off” Penn Jillette

Penn’s Current Diet: An Extreme Approach to Intermittent Fasting

  • Nowadays, Penn, who’s vegan, fasts for 23 hours every day, maintaining a strict 1-hour feeding window
    • “If you were to sit down with me during that one hour of feeding, you would be appalled by the actual volume of food that I’m able to eat” – Penn Jillette
  • What does Penn eat for his one meal?
    • A salad “the size of your head”
    • ~6 servings of brown rice
    • Chili bean stew
    • Some guacamole
    • A TON of fruit for dessert (~5 “containers” of blueberries, 2 cups of pomegranate seeds)
    • All topped off with a few squares of 90% dark chocolate

Wrapping Up | Penn is on a Mission to Weaponize Kindness and Ditch the Notion of “Teams”

  • “I think the biggest challenge we face, even with climate change on the table… is staying kind with profound disagreement, and staying kind when a mechanism has been set up to make money and power out of hate.” – Penn Jillette 
  • “If you want to change the world, you’re better off with non-violence… Non-violent revolutions have been successful, more often, than violent ones.” – Penn Jillette
  • 🎧 “I don’t want to see teams anymore. I don’t want to see ‘us’ and ‘them.’ … My obsession right now is to weaponize kindness and see ourselves as not teams.”Pen Jillette
    • “And I mean teams in every f***ing way, whether your team is atheists or whether your team is Democrats.”

Additional Notes

  • Brian Koppelman introduced Tim to Penn
  • When it comes to magic, James Randi is one of Penn’s biggest influences
  • Penn recently completed a 14-day fast
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