Season 1
Feb. 9, 2021
#44: Jordan Harbinger – The secret to effective sales, dating, and hosting a popular podcast
Jordan Harbinger is a Wall Street lawyer turned podcast interviewer with an approachable style and knack for securing high-profile guests.
Feb. 2, 2021
#43: Emily Clouse – Our podcast illustrator talks drawing, breaking into comedy, and our childhood
Emily Clouse is a Los Angeles-based comedy writer and cartoonist who illustrates this show!
Jan. 26, 2021
#42: Alex Cattoni – From behind-the-scenes copywriter to front-of-camera YouTuber
Alex Cattoni is a copywriter, marketer, and the founder of The Copy Posse, where she teaches people to become freelance copywriters.
Jan. 19, 2021
#41: Tim Urban – Why the author of Wait But Why focuses on quality over consistency
Tim Urban is the writer of the blog Wait But Why. Tim writes about topics including artificial intelligence, brain-computer interfaces, alien life, the size of the universe, and more.
Jan. 12, 2021
#40: Matty Benedetto of Unnecessary Inventions
The evil genius of Unnecessary Inventions creates products no one is asking for
Jan. 5, 2021
#39: Chris McAlister – Meet my business and creative coach
Chris McAlister is the founder of SightShift, a company that helps ambitious people be courageous and kind.
Dec. 22, 2020
#38: The 12 Clips of Christmas
A look back at some of the gifts guests have given us this year
Dec. 15, 2020
#37: Ali Abdaal – Making a living as a part-time YouTuber
Ali Abdaal is a Cambridge University medicine graduate, now working as a junior doctor in the UK's National Health Service (NHS). He started making YouTube videos in his final year of medical school at Cambridge University i…
Dec. 8, 2020
#36: Matt Ragland – Becoming a full time YouTube creator after 10 years of side hustling
Matt Ragland is an independent creator. His YouTube channel showcases videos on the Bullet Journal process, productivity, and time management.
Dec. 1, 2020
#35: David Perell – How "The Writing Guy" thinks about Twitter, education, and creating your own games
David Perell is a writer, podcaster, and the creator of Write of Passage.
Nov. 17, 2020
#33: Brian Clark – A content marketing pioneer talks about its evolution
Brian Clark is founder of the pioneering content marketing website Copyblogger, the personal growth newsletter Further, and Unemployable, a resource that provides smart strategies for freelancers and entrepreneurs.
Nov. 10, 2020
#32: Dan Andrews – Helping location independent entrepreneurs build businesses and find community
Dan Andrews is the creator and host of the Tropical MBA podcast, a show for location independent entrepreneurs.
Oct. 27, 2020
#31: Sahil Lavingia – Gumroad and the evolution of online creators
Sahil Lavingia is the founder and CEO of Gumroad. Gumroad is an online platform that facilitates the sale of products by creators directly to consumers.
Oct. 20, 2020
#30: Anne-Laure Le Cunff – From burnout to mindful productivity and quickly building an audience
Anne-Laure Le Cunff is an entrepreneur, an ex-Googler, and a neuroscience student.
Oct. 13, 2020
#29: Khe Hy – Leaving Wall Street success to find fulfillment and start an email newsletter
Khe Hy is the creator of RadReads, a weekly newsletter covering how to live an intentional life.
Oct. 6, 2020
#28: Bryce Conway – How a travel hacker evolved to become a content creator and affiliate marketer
Bryce Conway is the Founder of 10xTravel.com and Author of Takeoff: How to Travel the World for Next to Nothing and How to Fix Your Credit: Do it Once. Do it Right. Get on with Your Life.
Sept. 29, 2020
#27: Ran Segall – How a freelance designer's YouTube hobby paved the way to becoming an educator
Ran Segall is the creator of Flux Academy. Previous to Flux, Ran was a freelance designer with nearly 20 years of experience.
Sept. 22, 2020
#26: Ryan Robinson – How to write blog posts that rank on page one of search results
Ryan Robinson is a full-time blogger, podcaster and content marketing consultant.
Sept. 15, 2020
#25: Eric Jorgenson – Creating a full-length book from Tweets, interviews, essays, and podcasts
Eric Jorgenson is the author of The Almanack of Naval Ravikant: A Guide to Wealth and Happiness (also called Navalmanack).
Sept. 8, 2020
#24: Tiffany Aliche, The Budgetnista – Paying off debt, saving for retirement, weathering a recession, and building wealth
Tiffany "The Budgetnista" Aliche is an author, speaker, and founder of the Live Richer Academy.
Sept. 1, 2020
#23: Kwame Christian – How an expert negotiator thinks strategically about expanding his reach
Kwame Christian is one of the foremost experts in the field of negotiation and conflict resolution.
Aug. 25, 2020
#22: Pat Flynn and Matt Gartland – Why Pat acquired a Matt's agency in order to grow Smart Passive Income
Smart Passive Income is a media company elevating entrepreneurs to within reach of their dreams.
Aug. 18, 2020
#21: Matt D'Avella – Freelancing, filmmaking, podcasting, and finding success on YouTube.
Matt D'Avella is a filmmaker, YouTuber & podcaster that explores what it means to live a good life. Matt directed Minimalism: A Documentary About the Important Things, which was acquired by Netflix in 2016.