When to Quit – Lessons from World-Class Entrepreneurs, Investors, Authors, and More

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“Remember: it’s not a failure until you accept defeat.”

-Debbie Millman


I’m very excited to share this episode. It’s our first “roundtable” approach to discussing a single topic. This came about when I asked 5-Bullet Friday subscribers (sign up here if you’re interested) to send me questions, and one that stuck out was: Where’s the line between stubbornly pursuing an idea that isn’t working and the patience and persistence needed to actually make it work? In other words — when should you give up and quit and when should you push on?


Since this is something I myself have struggled with, I came to the conclusion that I should reach out to people who might have a better answer. So, I sent the question to the following entrepreneurs, authors, and innovators:



Scott Belsky
Seth Godin
James Altucher
Debbie Millman
Adam Robinson
Chase Jarvis
Rhonda Patrick

Their answers are a thorough overview of how to assess your own ideas and opportunities, and determine which ones are worth pursuing. Enjoy!


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Listen to it on iTunes.
Stream by clicking here.
Download as an MP3 by right-clicking here and choosing “save as.”

Want to hear my first episode with Debbie Millman? — Listen to this episode, where we discuss how to recover from rejection, how to overcome personal crises of faith, class exercises from her most impactful mentors, and much more. (stream below or right-click here to download):






This podcast is brought to you by Shopify. With the help of Shopify, many readers of my blog — first-time business owners — have ended up making millions of dollars each with their side gigs. Back in 2009, I helped create Shopify’s Build a Business, which is now the world’s largest entrepreneurship competition.


The goal of this competition is to entice would-be entrepreneurs to get off the couch and make things happen, and all you have to do to qualify is open a store on Shopify and start selling. Top sellers in each category then have the exclusive opportunity to learn from mentors and experts like Tony Robbins, Daymond John, Seth Godin, Sir Richard Branson, and me in a location like Necker Island.


Listeners to this show can go to shopify.com/tim to sign up for a free, 30-day trial and gain access to video courses that will help you get started — including “How to Quickly Start a Profitable Dropshipping Store” with Corey Ferreira and some goodies from me. Check it out at shopify.com/tim today!


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. When 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. Give it a test run…


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…



Selected Links from the Episode

Connect with Scott Belsky:

Website | Behance | Twitter



Connect with Seth Godin:

Website | Twitter



Connect with James Altucher:

Website | Twitter



Connect with Debbie Millman:

Website | Twitter | Facebook | Instagram | Design Matters Podcast



Connect with Adam Robinson:

Website | Twitter



Connect with Chase Jarvis

Website | CreativeLive | Twitter | YouTube | Facebook | Instagram 



Connect with Rhonda Patrick:

Found My Fitness | Podcast | Twitter | Facebook | Instagram



Divestiture Aversion (aka the Endowment Effect)
The Dip: A Little Book That Teaches You When to Quit (and When to Stick) by Seth Godin
Question of the Day (QOD) Podcast
Freakonomics: A Rogue Economist Explores the Hidden Side of Everything by Steven D. Levitt and Stephen J. Dubner
Stockpickr! Your Source for Stock Ideas
Become An Idea Machine: Because Ideas Are The Currency Of The 21st Century by Claudia Azula Altucher and James Altucher
A Confederacy of Dunces by John Kennedy Toole
The Sunk Cost Fallacy by David McRaney, You Are Not So Smart
The Best Camera Is The One That’s With You: iPhone Photography by Chase Jarvis
Recording Analog Memories in Human Cells by Anne Trafton, MIT News Office
Born for This: How to Find the Work You Were Meant to Do by Chris Guillebeau
1,000 True Fans by Kevin Kelly

Show Notes

Why Scott Belsky stuck with Behance even when it was going through rough patches. [08:41]
Seth Godin thoughts from his bestselling book about quitting. [13:24]
James Altucher tells us why you sometimes want to quit when you’re ahead. [19:53]
Debbie Millman on pursuing dreams over conforming to the comfortable. [38:58]
Adam Robinson ponders the options we all face: to persist, to pivot, or to quit. [47:11]
Chase Jarvis on intuition as the most powerful tool we have as humans and the science behind it. [57:12]
Rhonda Patrick gives us some insight on why making a counterintuitive choice ended up working in her favor. [1:11:19]

People Mentioned

Jerry Seinfeld
Howard Stern
Stephen Dubner
Brian Koppelman
Marina Franklin
AJ Jacobs
Fyodor Dostoyevsky
Leo Tolstoy
W.C. Fields
Rudyard Kipling
Mikhail Baryshnikov
John Kennedy Toole
Thelma Toole
Walker Percy
Gary Vaynerchuk
Mark Cuban
Richard Branson
Chris Guillebeau
Bruce Ames
Kevin Kelly
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Published on July 23, 2017 11:29
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