Jamie Russo Returns! — Author of The Underdog Paradox Shares Stories of Everyday Heroism, The Craft of Writing, and Entrepreneurship for Positive Change (#40)

Listen on Spotify | Listen on Apple | Watch on YouTube

No matter what you’re building, first and foremost, every idea, every product, every business – everything – starts with a great story.

Jamie Russo

This conversation will turn assholes into saints.

Today I’m joined by JAMIE RUSSO! (@jamierusso) Last time Jamie and I talked he wasn’t the bestselling author of a yellow book called The Underdog Paradox. Now, he is. Way cool. We spent 2 hours chatting the craft of writing, entrepreneurship for social change, pivots, how to battle and overcome adversity, writing everyday, habits, moms, and more.

Support Jamie Russo on the Information Super Highway at…


Jamie on Twitter

Buy and read Jamie’s book The Underdog Paradox

In this episode we cover…

  • Jamie is part of the Build in Public movement. So why did he decide not to talk about The Underdog Paradox while writing it? (5:00)
  • Why did Jamie need to write the book? (10:00)
  • Did Jamie learn anything surprising while writing the book? (15:00)
  • The story of Lual Mayen: building video games for social impact (20:00)
  • Moms and mentors (28:00)
  • The myth of the lone creator is a myth (32:00)
  • Writing a book is a huge roller coaster of emotions / The Underdog Paradox almost became a book on investing!? (35:00)
  • Tools for writing: what did Jamie use to write the book? Google Docs? Word? Notepad? (41:00)
  • Listening to music while writing late at night (46:00)
  • Goodnote, drip marketing (52:00)
  • Jamie breaks down Rosie Sherry’s tips on community building (1:00:00)
  • What’s next for Jamie Russo? (1:02:00)
  • Don’t succeed too fast / It all starts with a good story (1:05:00)
  • How does one harness the benefits of being an underdog after reaching success? (1:08:00)
  • The best competitive advantage (1:12:00)
  • TURN UP THE VOLUME (1:18:00)
  • Jamie shares the love for his friends and family (1:22:00)
  • Finding your voice as a writer (1:26:00)
  • Failure / the holy grail of growth hacker marketing (1:28:00)
  • Writing everyday is the same as crapping everyday (1:34:00)
  • Habits for writing and life: Go analog! Get rid of all that digital crap (1:38:00)
  • What does it feel like to publish a book? (1:40:00)
  • We bid you farewell: Shoutouts and parting words (1:45:00)



Lual Mayen



Crocodile Tears by Bunt (Jamie listened to this song on loop for hours while writing The Underdog Paradox)

Rosie Sherry

Ryan Holiday

Tiago Forte

Steph Curry

Dan Bilzerian

Josh Ostrovsky (The Fat Jewish)

John Daub

Not Boring Newsletter

Please enjoy! Cheers, and here’s to your good health.

Listen on Spotify | Listen on Apple | Watch on YouTube

Does The Penguin Latte Podcast remind you of fresh presents on Christmas morning? If so, please consider leaving a review on Apple Podcasts/iTunes. It takes all of 60 seconds (61 if you’re feeling extra spicy). Reviews make the podcast 1% better. If 500 of you leave reviews, the podcast gets 500% better. Plus, I love reading all of your juicy comments. Thanks!

This episode is brought to you (and powered) by Flow State Coffee! My buddy and regular guest Greg Frontiero started a company that sells products designed to put you in that groovy sensation called Flow. His first product, Flow State Coffee, is some of the best coffee I’ve tasted. Plus, it doesn’t make you feel like you’re about to have a heart attack after drinking 6 cups of it (I’ve tried).


Use this link to buy a bag with code PAUL automatically applied for a discount.

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