Penn Jillette on Magic, Losing 100+ Pounds, and Weaponizing Kindness (#405)

“One of the biggest challenges we face 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

Penn Jillette (@pennjillette) is a cultural phenomenon as a solo personality and as half of the world-famous, Emmy Award-winning magic duo and Las Vegas headliners Penn & Teller.

Together since 1975, Penn & Teller’s live show spent years on Broadway and is now the longest-running headliner show in Las Vegas where it plays nightly at The Rio All-Suite Hotel & Casino. The pair has been awarded Las Vegas Magicians of the Year an amazing eights times.

As part of Penn & Teller he has appeared on hundreds of shows, from The Simpsons and Friends to Billions. He recently co-wrote an episode of the Emmy-winning Netflix series Black Mirror.

He co-hosted the controversial Showtime series Penn & Teller: Bullshit! which was nominated for thirteen Emmy Awards, won him a Writers Guild award, and was the longest-running show in the history of the network. He currently co-hosts the CW Network hit competition series Penn & Teller: Fool Us! which was nominated for a 2017 Critics’ Choice award.

Penn’s latest book, The New York Times Best Seller Presto! takes an insightful and very humorous look at his recent weight loss journey. His previous book, God No! Signs You Might Be An Atheist and Other Magic Tales, spent six weeks on The New York Times Best Sellers list.

His weekly podcast, Penn’s Sunday School, was the number one downloaded podcast on Apple Podcasts during its debut week, and was named a Best New Comedy Podcast by Apple Podcasts.

On the big screen, Penn produced the critically lauded 2005 documentary The Aristocrats, which features over 100 of the biggest names in comedy telling their versions of the dirtiest joke in history. He produced Tim’s Vermeer, which follows the journey of an eccentric inventor determined to solve one of the art world’s oldest mysteries. The Sony Pictures Classics release was nominated for a BAFTA and was shortlisted for the 2014 Oscars. He has recently completed the documentary Gambler’s Ballad profiling magic legend Johnny Thompson.

Penn & Teller have their very own star on the Hollywood Walk of Fame and triumphantly returned to Broadway recently with Penn & Teller On Broadway, which was the highest-grossing non-musical for the entirety of its run.

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

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform. 

#405: Penn Jillette on Magic, Losing 100+ Pounds, and Weaponizing Kindness

This episode is brought to you by Brave, the next-generation Web browser. Brave was built by a team of privacy-focused, performance-oriented pioneers of the Web at the direction of Brendan Eich (co-founder of Mozilla Firefox and creator of JavaScript) and Brian Bondy. Brave now has more than 10 million monthly active users—including me.

Why Brave? Because Brave gives you unmatched speed, security, and privacy. Whereas other browsers suck up your data — profiling and tracking you across the Web and using that information to manipulate your decisions — Brave operates up to six times faster by blocking ads and website trackers, preserving your anonymity and protecting you from this surveillance economy. Brave also includes options such as Private Window with Tor for those seeking advanced privacy and safety. Intuitive and easy to use, Brave allows you to import bookmarks from other browsers with one click, and all your favorite Chrome extensions are available with Brave. Listeners of The Tim Ferriss Show can easily upgrade their browser for free right now by going to

This episode is also brought to you by LinkedIn Jobs. Hiring can be hard, and it and be super expensive and painful if you get it wrong. Today, with more qualified candidates than ever — but also more noise than ever — employers need a hiring solution that helps them find the right people for their businesses. LinkedIn Jobs provides just that by screening candidates with the hard and soft skills you’re looking for so you can quickly find and hire the right person.

LinkedIn can make sure your job post gets in front of people you want to hire — people with the skills, qualifications, and other insights that help LinkedIn paint a better picture of potential candidates. It’s no wonder great candidates are hired every eight seconds on LinkedIn. Find the right person meant for your business today with LinkedIn Jobs. You can pay what you want, and the first $50 is on LinkedIn. Just visit to get $50 off your first job post! Terms and conditions apply.

What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with a friend Penn and I share? — Listen to my conversation with Brian Koppelman, co-writer/producer of Rounders, Billions, The Illusionist, and Ocean’s Thirteen. In the episode, we explore how he got started, how he handles rejection, his big breaks, creative process, and much more (stream below or right-click here to download):

#10: Brian Koppelman, Co-writer/Producer of Rounders, The Illusionist, Ocean's Thirteen


  • Connect with Penn Jillette:

Penn & Teller | Penn’s Sunday School | Twitter


  • How does Penn know our mutual friend Brian Koppelman, and what do they share in common? [08:10]
  • Who is James Randi, and how did he come to be such an influence on Penn? [10:57]
  • What can we do to guard against deceit by becoming more skeptical without becoming more cynical? [18:09]
  • Joking that journaling is “one way to teach yourself that you don’t remember things properly,” what got Penn to start keeping a journal at age 30, and how does he use journaling today? After 34 years, how does he benefit from the time he puts into the almost-daily practice? [24:37]
  • Confessing he has a visual memory so weak that it’s been “studied by people,” how does Penn compensate for this in his professional life? Does it give him a unique edge? [37:36]
  • What does the content of Penn’s dreams look or feel like? [43:14]
  • What led to Penn’s period of homeless wandering in his youth, how long did it last, and how did it differ from what we might think of as “homeless” in the modern context? [48:14]
  • What constituted Penn’s street performance that earned him “several grand a week” during this homeless period, how did he manage to consistently get a crowd of 300-500 people to watch him perform, and why is his distinctive voice a direct result of these performances? [52:30]
  • How did this period shape the way Penn sees the world today? What did it teach him about trusting other people and deescalating hostility? [58:43]
  • How young hippie hobo Penn defused a potentially violent confrontation with a pair of macho truckers in a Corn Belt diner using only his quick wits and a cold, sticky milkshake. [1:03:15]
  • Penn has never partaken of drugs or alcohol, which is a claim not many can make. To what does he credit this abstinence? [1:09:31]
  • How did Penn lose 0.9 pounds a day for four months under the direction of former NASA scientist Ray Cronise? [1:14:14]
  • What weight loss (and an illegal trip on NASA’s “Vomit Comet”) did to change Penn’s atheistic perspective on mind-body duality. [1:22:36]
  • What Penn’s — some would say extreme — version of intermittent fasting looks like. [1:27:31]
  • What did Ray Cronise mean when he said “You can’t outrun your mouth” while forbidding Penn to exercise during the four-month weight-loss regimen — and do I agree with this? (As an aside, it was determined that performing nightly 90-minute Penn & Teller shows burns a lot of calories, effectively nullifying Ray’s no-exercise rule.) [1:33:30]
  • Penn shares what he took away from lucky interactions with legendary theoretical physicist Richard Feynman and his fellow Nobel laureate Murray Gell-Mann. [1:38:24]
  • Why Richard Feynman (and possibly Bob Dylan) would pass Tim Jenison’s data points test. (Would you?) [1:48:14]
  • With so many projects from which to choose at any given time, how did Penn decide to put time into making the (in my opinion, excellent and very worth your while) documentary Tim’s Vermeer? What’s it about, and what were the obstacles faced along the way in trying to get it made? [1:50:58]
  • What be on Penn’s billboard? [1:59:25]
  • Parting thoughts, a seemingly impossible thought experiment, and Penn’s hope that we can stay kind to one another with profound disagreement in these divisive times. [2:00:55]


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.

Leave a Reply

Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

11 Replies to “Penn Jillette on Magic, Losing 100+ Pounds, and Weaponizing Kindness (#405)”

  1. I was laying in bed unable to sleep while watching the snowcats grooming the mountain when I thought how great it would be to do some runs with Tim. We have a Chalet less than five minutes from the chairlifts and a spare living area if you ever find yourself up in Washington state.

  2. Great episode Tim. Penn is brilliant! This is right up there with the Jamie Foxx interview! One comment though..I believe Kreskin was on the Carson show 88 times. One of Johnny’s favorites. Maybe he was thinking of Uri Geller?

  3. Great read and my first for your Blog!

    I’m 57 now, workout most days doing HIIT and intermittent fast as well!…for the last 3 years In fact! Age for me has nothing to do with my continued desire to stay healthy. It’s just a way of life.

    I know health was an interest for you Tim. I was one of the people you called up on a regular basis all those years ago when you had BRAINQUIKEN 😉 you may remember me, my company was called Bytomic, in the UK. You remember we were a Martial Arts Gear company Must have been around 2001-2002? So how did I put this all together and connect you to it all? I have a funny story.

    I only found out Tim when one day, maybe around 2006 or 7 I was waiting for a flight to Las Vegas in London and I thought, “I know I need a good book to read for the flight”. So I was browsing in the book shop there, and me being me I was looking at the business section when I picked up a book called ‘The 4 Hour Work Week’.

    I opened it and read the intro and your story…and I nearly dropped the book there and then! BRAINQUIKEN!! I sold that! I bought that! From you? Lol…yes it must have been. What a surprise I had.

    I remember speaking with you quite a few time’s, and we did sell it quite successfully. I even spoke to someone recently who I told the story to and he told me he still had the bottle for Bodyquiken!!

    I’ve been interviewed on a few Podcasts in the direct response Niche recently and I tell the story. People love it.

    Anyway, I hope you’re well brother! Maybe catch up one day and talk old days!

    Best David Lowe.

  4. What an incredible episode! I’ve loved so many and I think I love this one even more. There are so many laughs and also a dense web of fantastic, important ideas to think about and learn about – more, much more. What a gift!

  5. Consider interviewing Tom Brady (painful request – I’m a Jets fan). Why? In the podcast “Sports Wars” about the Brady-Manning rivalry (season 12, episode 3), the narrator claims Brady was SLEEPING a half hour before his first super bowl! This reminds me of that Brazillian jui-jitsu master who sleeps before all of his matches because he’s in such a relaxed state (name escapes me). It strikes me there must be something unique about Brady. I mean, aside from his astonishing success in the NFL.

  6. I loved the part about how Penn is a natural genius at deescalating violence. Even though I thought the weight-loss approach was bizarre, I enjoyed listening to it and how he whole-heartedly experimented on himself. Also fascinating to hear how he thinks the weight loss has changed his personality for the better!

  7. Did I miss it, what application does Penn use for journaling? How does he keep the records going back so many years, surely he would lose them without it being cloud based?