Sahil Lavingia has had an epic journey as an entrepreneur: he dropped out of college to become employee #2 at Pinterest and then went on to found Gumroad, one of the largest platforms for creators to sell their work and earn a living online. After the company failed to meet its VC-driven growth timeline and almost died, Sahil had to lay everyone off and build it back up into the resilient, streamlined, and fully distributed company it is today.

Episode web page.

—

Sign up here to get upcoming essays + episodes emailed to you.

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

—

Links & resources mentioned:

• Send episode feedback on Twitter @askotzko , or via email

• Sahil Lavingia: Gumroad, Twitter, personal site

• Book: The Minimalist Entrepreneur

• “Reflecting on My Failure to Build a Billion-Dollar Company”: essay + talk

• Sahil’s early stage investment fund

—

Related episodes:

• #42 ARM: A mental model for fulfilling work

—

People & orgs:

• Gumroad

• USC

• Patreon

• BandCamp

• Substack

• Daniel Vassallo tweet about money he’s made Gumroad

• Paul Graham: “You've found market price when buyers complain but still pay.”

—

Books:

• The Minimalist Entrepreneur

• Essentialism

• Only the Paranoid Survive

—

Other resources:

• How Gumroad is run: No Meetings, No Deadlines, No Full-Time Employees

• Video: Gumroad Q4 2022 board meeting - where pricing change was announced

• “Reflecting on My Failure to Build a Billion-Dollar Company”: essay + MicroConf talk

• What is a transformer model (AI)?

Five things I (re)learned from spending a week with SVPG + some of the best product coaches in the world.

=====

You can read this episode here.

Sign up here to get upcoming audio essays emailed to you

Follow the MTTM journey on Twitter or LinkedIn! 

If you haven't already would you do me a favor and  take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

Links & resources mentioned

Send episode feedback on  Twitter @askotzko , or via email 

—

Related episodes

• #60 DJ DiDonna: Navigating sabbaticals and career breaks 

—

People & orgs

• Marty Cagan & SVPG 

—

Books

• The Thin Book of Trust

—

Other resources mentioned

• Vision example: SpaceX

• Vision example: Microsoft productivity

• Vision example: Apple’s Knowledge Navigator

• Scaled Agile Framework (SAFe)

• Original agile manifesto 

DJ DiDonna helps us approach taking REAL time off and evolving our identity along with our career.

Whether you’re feeling like you need to take time off, or if you’re curious about what sabbaticals are and why they might be good for both you and your organization, have a listen. You’ll learn about how your interests and identity can evolve along with your career, but not be bound by your career.

—

Links & resources mentioned

• Send episode feedback on Twitter @askotzko , or via email

• DJ DiDonna: LinkedIn

• The Sabbatical Project

—

Related episodes:

• #59 Kenny Borg: Identity transformation and embodying fulfillment

—

People & orgs:

• The Sabbatical Project

—

Books:

• Designing Your Life: How to Build a Well-Lived, Joyful Life

• Transitions: Making Sense of Life's Changes

• Pivot: The Only Move That Matters Is Your Next One

• How Will You Measure Your Life?

• The Lies of Locke Lamora

—

Other resources:

• TED talk: Stefan Sagmeister: The power of time off

• DJ’s TEDx talk: Sabbaticals: Time [off] well spent

• LinkedIn career break feature

• Research: “The three meanings of meaning in life: Distinguishing coherence, purpose, and significance”

• Exercise: 2022 Reflection + 2023 Goal Setting

Kenny Borg helps us explore the ongoing evolution of our identity, deal with imposter syndrome, and embody fulfillment throughout the journey instead of putting it off to the end. He cofounded Ethr, a coaching collective that exists to help you develop a relationship with your own consciousness and actualize your wisdom. Before that, he spent more than a decade as a founder & CEO operating and advising direct to consumer brands. 

-----

You can also read this episode here.

Sign up here to get upcoming audio essays emailed to you

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

• Send episode feedback on Twitter @askotzko , or via email
• Kenny Borg: LinkedIn, Instagram
• Ethr
• Related episodes
  • #24 Laura Garnett: Find your zone of genius and never fear a job search again
  • #9 Amy Edmondson: Building teams where people feel safe
• People & orgs
  • Ethr
  • Joseph Marshall
  • Crazy Horse
• Books
  • An Everyone Culture
  • Atomic Habits
  • The Power of Ritual
  • The Genius Habit
  • The Power of Four: Leadership Lessons of Crazy Horse
  • The Lakota Way

Scott Young is an expert on rapid, effective learning. This ep will help you learn new skills effectively and quickly amidst the chaos of real life.

-----

You can also read this episode here.

Sign up here to get upcoming audio essays emailed to you

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

• Send episode feedback on Twitter @askotzko , or via email
• Scott Young: website, Twitter
  • Book: Ultralearning
  • Scott's podcast
  • Course: Top Performer
  • Previous challenges
    • The MIT Challenge
    • The Year Without English
• Related episodes
  • #54 David Kadavy: Creative self-actualization
• People & orgs
  • Cal Newport
  • Benny Lewis
  • Steve Pavlina
  • James Clear
• Books
  • Deep Work
  • Fluent in 3 Months
  • Four Thousand Weeks: Time Management for Mortals
  • Atomic Habits
  • Fluent Forever
  • Polarity Management
• Other resources mentioned
  • Desirable Difficulties: When Harder is Better for Learning - Scott H Young
  • The Human Brain | Brain and Cognitive Sciences | MIT OpenCourseWare
  • Thinking on the margin - Definition and examples — Conceptually.)
  • Anki

Rob Fitzpatrick is the author of The Mom Test, and he'll help you fight the good fight to bring your ideas into the world.

-----

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

Links & resources mentioned

Send episode feedback on Twitter @askotzko , or via email

Rob Fitzpatrick - Twitter, websiteBooks:The Mom TestThe Workshop Survival GuideWrite Useful BooksNonfiction Author's Community

Related episodes#56 Ash Maurya: The Innovator's Gift#54 David Kadavy: Creative Self-Actualization

People & orgsSherry Walling

BooksThe Entrepreneur’s Guide to Keeping Your Sh*t TogetherRocket FuelPartnering: Forge the Deep Connections That Make Great Things HappenFour Thousand Weeks: Time Management for MortalsMind Management, Not Time Management

Other resources mentionedThe shape of an idea - Rob FitzpatrickEffectuationTrends.vcThe new biz model for indie creators? Gluing it all together with an Outcome-Oriented Community.💡 Beyond retention, toward outcomes | Robfitz in progressEl Camino de SantiagoJobs To Be DoneThe 3 Paradoxes of Life - Mark Manson

Ash Maurya introduces "The Innovator's Gift" to help you find problems worth solving, and navigate the uncertainty of new product ideas.

-----

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

Links & resources mentioned

Send episode feedback on Twitter @askotzko , or via email

Ash Maurya - LEANSTACK, TwitterAsh's books:New: Running LeanScaling Lean

Related episodes#55: How does continuous discovery come together for a new product?#44 Teresa Torres: Habits for clear thinking and better product bets

People & orgsBob MoestaTom ChiTom Chi talk @ MindValley: Everything is Connected - Here's HowW. Edwards DemingPeter DruckerSteve BlankEric RiesDave McClureSean Ellis

BooksThey All Laughed: The Fascinating Stories Behind the Great Inventions That Have Changed Our LivesUser Story MappingWhen Coffee and Kale Compete (JTBD) - Alan KlementDemand-Side Sales - Bob MoestaThe ONE ThingThinking in Systems

Other resources mentionedCustomer forces canvasLEAN canvasJobs to Be Done (JTBD)The Milkshake StudyRecency Bias

How to apply continuous discovery techniques to a nascent, early stage product that doesn't yet have product-market fit.

-----

You can also read this episode here.

Sign up here to get upcoming audio essays emailed to you

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

—

Links & resources mentioned

Related episodes

• #44 Teresa Torres: Habits for clear thinking and better product bets

• #31 Marty Cagan: Empowering product teams to do the best work of their lives

—

People & orgs

• Teresa Torres

• Ash Maurya

• Jeff Patton

• Marty Cagan

—

Books

• Continuous Discovery Habits, by Teresa Torres

• INSPIRED, by Marty Cagan

—

Other resources:

• Andrew's original Twitter thread

• Opportunity Solution Trees - Teresa Torres

• Jeff Patton - Story Mapping

• Lean(er) Canvas - Ash Maurya

• Jobs to Be Done (JTBD)

David Kadavy will help you follow your curiosity, find your way to creative self-actualization, and learn to discern what you really want.

-----

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

Links & resources mentioned

Send episode feedback on Twitter @askotzko , or via email

David Kadavy: website, Twitter, podcastDavid's podcast: Love Your WorkDavid's newsletter, Love MondaysDavid's books:Design for HackersThe Heart to StartMind Management, Not Time ManagementDigital Zettelkasten: Principles, Methods, & Examples

Related episodes#9 Amy Edmondson: Building teams where people feel safe#49: Founders Pledge - Thoughts on entrepreneurship and philanthropy

People & orgs80,000 HoursEffective Altruism

BooksWork, by James SuzmanDoing Good Better (effective altruism)Why We Make Things and Why It Matters, by Peter KornFlow, by Mihaly CsikszentmihalyiThe Time Paradox, by Philip ZimbardoBorn Standing Up, by Steve MartinSo Good They Can't Ignore You, by Cal NewportThe Case Against Education, by Brian CaplanThe Art of Learning, by Josh WaitzkinMy Creative Space, by Donald Rattner

Other resources mentionedDonald Rattner on David's podcastFounders PledgeEzra Klein podcast with James SuzmanSteve Jobs 2005 Stanford commencement addressSocial desirability biasTheranos - Elizabeth HolmesTaylorismNaNoWriMo

Some short thoughts on how to review and close out a tough year, and set ourselves up for a powerful, generative new year.

Links & resources mentioned are here.