Calm AI for Crazy Days: Inside Granola's Design Philosophy, with co-founder Sam Stephenson
Sam Stephenson, co-founder of Granola, explains how a deliberately minimalist design philosophy helped turn the AI note-taking app into one of the fastest-growing products in the market. He shares why Granola focuses on doing one job exceptionally well, how note sharing drives growth, and what they’ve learned from surprising use cases, recipes, and constant user research. The conversation also covers privacy and consent, transcription and cost choices, team collaboration, and Sam’s hopes for AI products that create less screen time and more space for reflection.
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Sponsors:
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CHAPTERS:
(00:00) About the Episode
(03:52) Special Sponsor
(05:52) Granola growth and users
(17:14) System2 goals and context (Part 1)
(17:19) Sponsors: Roboflow | VCX
(20:15) System2 goals and context (Part 2)
(33:09) Costs, pricing, and transcription (Part 1)
(33:22) Sponsors: Claude | Tasklet
(37:12) Costs, pricing, and transcription (Part 2)
(47:38) Meeting privacy and consent
(54:13) Agents, memory, and simplicity
(01:03:49) Recipes, use cases, and growth
(01:11:52) AI product design culture
(01:28:08) Future risks and vision
(01:33:33) Episode Outro
(01:36:59) Outro
PRODUCED BY:
https://aipodcast.ing
DHH’s new way of writing code
Brought to You By:
• Statsig — The unified platform for flags, analytics, experiments, and more.
• Sonar – The makers of SonarQube, the industry standard for automated code review
• WorkOS – Everything you need to make your app enterprise ready.
—
David Heinemeier Hansson (DHH) is the creator of Ruby on Rails and Omarchy, co-founder and CTO of 37signals (maker of Basecamp and HEY), and the author of several books including the best-seller, Remote: Office Not Required, co-written with Jason Fried.
Six months ago, in an episode of the Lex Fridman podcast, David shared how he doesn’t use AI tools to write code: he types out all his code. But things have changed a lot since then.
In this episode, we discuss his approach to building software, how it’s changed in the last six months, and why he now takes an agent-first approach, and how he barely writes any code by hand. We go into how he uses AI agents: which alter how he builds and explores ideas, but also how his standards of quality and craft remain the same.
We also discuss how 37signals thinks about product development, from the role of designers to the importance of aesthetics and taste. David gets into how he sees beauty and functionality as closely linked, and why strong opinions about design lead to better software.
Finally, we look into the uneven impact of AI which amplifies senior engineers while creating challenges for junior developers, and what this may mean for the role of the software engineer.
—
Timestamps
(00:00) Intro
(02:11) Omarchy and Ruby on Rails
(08:25) 37signals overview
(10:12) Launching HEY
(18:38) Building HEY
(22:47) Designers at 37signals
(28:08) The craft of design
(31:52) Why DHH now embraces AI workflows
(39:45) The AI inflection point
(44:23) DHH’s agent-first workflow
(55:09) AI’s impact on junior developers
(1:03:08) Developer experience with AI
(1:16:43) What does AI mean for developers?
(1:23:33) 37signals teams and hiring
(1:38:20) Work-life balance with AI
(1:41:41) Why DHH keeps building
(1:45:24) Closing
—
The Pragmatic Engineer deepdives relevant for this episode:
• Are AI agents actually slowing us down?
• How Claude Code is built
• The future of software engineering with AI: six predictions
• The AI Engineering Stack
• Mitchell Hashimoto’s new way of writing code
• How Linux is built with Greg Kroah-Hartman
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@pragmaticengineer.com.
Get full access to The Pragmatic Engineer at newsletter.pragmaticengineer.com/subscribe
DHH: $100M+ Advice That'll Piss Off Every Business Guru
Get Sam's guide to run your life like a $100M biz: https://clickhubspot.com/kdmv
Episode 806: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to David Heinemeier Hansson ( https://x.com/dhh ) about AI, being wrong in public, and taking on Apple.
—
Show Notes:
(0:00) How to stand out
(7:48) not giving a damn
(9:57) liquid vs crystalized intelligence
(12:03) constraints breed creativity
(18:18) being publicly wrong
(24:27) taste vs data
(33:25) Being in awe of Shopify
(41:05) how David uses AI
(47:49) What won't work today
(51:23) who David admires
(1:00:13) Longevity decisions
(1:07:09) Taking on the App Store and Google
—
Check Out Shaan's Stuff:
• Shaan's weekly email - https://www.shaanpuri.com
• Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents.
• Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies!
Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC
• I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out:
beehiiv.com/mfm-challenge
—
Check Out Sam's Stuff:
• Hampton - https://www.joinhampton.com/
• Ideation Bootcamp - https://www.ideationbootcamp.co/
• Copy That - https://copythat.com
• Hampton Wealth Survey - https://joinhampton.com/wealth
• Sam’s List - http://samslist.co/
My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /
#474 – DHH: Future of Programming, AI, Ruby on Rails, Productivity & Parenting
David Heinemeier Hansson (aka DHH) is a legendary programmer, creator of Ruby on Rails, co-owner & CTO of 37signals that created Basecamp, HEY, & ONCE, and is a NYT-best-selling author (with Jason Fried) of 4 books: REWORK, REMOTE, Getting Real, and It Doesn’t Have To Be Crazy At Work. He is also a race car driver, including a class-winning performance at the 24 hour Le Mans race.
Thank you for listening ❤ Check out our sponsors: https://lexfridman.com/sponsors/ep474-sc
See below for timestamps, transcript, and to give feedback, submit questions, contact Lex, etc.
Transcript:
https://lexfridman.com/dhh-david-heinemeier-hansson-transcript
CONTACT LEX:
Feedback – give feedback to Lex: https://lexfridman.com/survey
AMA – submit questions, videos or call-in: https://lexfridman.com/ama
Hiring – join our team: https://lexfridman.com/hiring
Other – other ways to get in touch: https://lexfridman.com/contact
EPISODE LINKS:
DHH’s X: https://x.com/dhh
DHH’s Website: https://dhh.dk/
Ruby on Rails: https://rubyonrails.org/
37signals: https://37signals.com/
DHH’s books:
Rework: https://amzn.to/44rSKob
Remote: https://amzn.to/44GFJ91
It Doesn’t Have to Be Crazy at Work: https://amzn.to/46bzuwx
Getting Real: https://amzn.to/4kzoMDg
SPONSORS:
To support this podcast, check out our sponsors & get discounts:
UPLIFT Desk: Standing desks and office ergonomics.
Go to https://upliftdesk.com/lex
Lindy: No-code AI agent builder.
Go to https://go.lindy.ai/lex
LMNT: Zero-sugar electrolyte drink mix.
Go to https://drinkLMNT.com/lex
Shopify: Sell stuff online.
Go to https://shopify.com/lex
NetSuite: Business management software.
Go to http://netsuite.com/lex
OUTLINE:
(00:00) – Introduction
(00:58) – Sponsors, Comments, and Reflections
(08:48) – Programming – early days
(26:13) – JavaScript
(36:32) – Google Chrome and DOJ
(44:19) – Ruby programming language
(51:30) – Beautiful code
(1:09:31) – Metaprogramming
(1:12:52) – Dynamic typing
(1:20:10) – Scaling
(1:33:03) – Future of programming
(1:50:34) – Future of AI
(1:56:29) – Vibe coding
(2:05:01) – Rails manifesto: Principles of a great programming language
(2:29:27) – Why managers are useless
(2:38:48) – Small teams
(2:44:55) – Jeff Bezos
(3:00:13) – Why meetings are toxic
(3:07:58) – Case against retirement
(3:15:15) – Hard work
(3:20:53) – Why we left the cloud
(3:24:04) – AWS
(3:33:22) – Owning your own servers
(3:39:35) – Elon Musk
(3:49:17) – Apple
(4:01:03) – Tim Sweeney
(4:12:37) – Fatherhood
(4:38:19) – Racing
(5:05:23) – Cars
(5:10:41) – Programming setup
(5:25:51) – Programming language for beginners
(5:39:09) – Open source
(5:48:01) – WordPress drama
(5:59:18) – Money and happiness
(6:08:11) – Hope
A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)
Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to them them escape the cycle of endless sprints, missed deadlines, and dragging projects.
What you’ll learn:
1. Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones.
2. The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines.
3. The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources.
4. Why most teams struggle with too little detail in their planning, not too much.
5. Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes.
6. Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process.
7. The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details.
8. The clear warning signs that your current development process is failing before it’s too late to change course.
9. Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment.
10. A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation.
11. Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management.
12. How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp.
—
Brought to you by:
• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs
• Merge—A single API to add hundreds of integrations into your app
• Airtable ProductCentral—Launch to new heights with a unified system for product development
—
Where to find Ryan Singer:
• X: https://x.com/rjs
• LinkedIn: https://www.linkedin.com/in/feltpresence/
• Website: https://www.ryansinger.co/
• Course: https://www.ryansinger.co/srl/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Ryan’s background
(04:38) The origins of Shape Up
(07:40) Implementing Shape Up in different companies
(09:56) How Shape Up is different
(19:02) The core elements of Shape Up
(26:29) Shaping sessions and timeboxing
(37:23) Flexible sprint planning
(38:56) The output of a shaping session
(46:57) Balancing detail and flexibility
(53:50) A deep dive into shaping sessions
(01:01:32) Fat marker sketches
(01:02:48) Getting started using Shape Up
(01:13:20) Signs it's time to try the Shape Up method
(01:18:25) Feature factories
(01:25:59) The role of the PM in Shape Up
(01:28:26) What makes Basecamp unique
(01:35:55) The second edition of the book
(01:38:30) Linking product strategy and shaping
(01:41:53) Conclusion and final thoughts
—
Referenced:
• Basecamp: https://basecamp.com/
• David Heinemeier Hansson on LinkedIn: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/
• Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/
• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking
• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/
• Intercom: https://www.intercom.com/
• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta
• How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of “Job Moves”): https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta
• Scrum: https://www.scrum.org/
• 37signals: https://37signals.com/
• Jobs to Be Done Theory: https://www.christenseninstitute.org/theory/jobs-to-be-done/
—
Recommended books:
• Shape Up: Stop Running in Circles and Ship Work That Matters: https://basecamp.com/shapeup
• Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progress/dp/1544509987/
• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612/
• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
#224 CTO & Co-Owner 37signals, David Heinemeier Hansson: Perfect Flow
Guest: David Heinemeier Hansson, CTO & co-owner of 37signals and creator of Ruby on Rails
37signals CTO David Heinemeier Hansson has organized his life around his passions: Writing, racing sports cars, and coding. “ Why aren't we all doing that?” he wonders. “Why aren't we all trying to optimize our life in such a way that much of it is enjoyable?”
Part of the problem, David argues, is that it’s impossible to find a creative or productive flow inside of mainstream work culture. Open offices, managerial over-hiring, and sloppy scheduling prevents people from reaching a flow state.
“40 hours a week is plenty than most people,” he says. “... So many people today are focused on just adding more and more hours. They're not thinking about how those hours are spent.”
Chapters:
(01:19) - 24 Hours of Le Mans
(06:48) - Amateurs in sports car racing
(10:54) - Flow and meditation
(15:25) - Mundane bulls**t
(18:14) - Optimizing for flow
(21:09) - Calendars and open offices
(24:30) - Full-time managers
(29:06) - Small companies
(32:20) - Selfishness and work
(40:21) - Taking other people’s money
(45:43) - Temptation
(49:49) - Moderately rich
(55:19) - “The day I became a millionaire”
(58:56) - The hassle
(01:03:58) - Achieving the dream
(01:08:34) - Shopify and Tobias Lütke
(01:14:50) - Trade-offs and downsides
(01:18:43) - The impact of Ruby on Rails
(01:22:02) - “I love being wrong”
(01:25:37) - DEI and illegal drugs
(01:29:49) - Not hiring
(01:30:35) - What “grit” means to David
Mentioned in this episode: TikTok, Minecraft, Mario Kart, Formula One, NASCAR, Lewis Hamilton, the NBA, Tesla Model S, Flow: The Psychology of Optimal Experience by Mihaly Csikszentmihalyi, Steve McQueen, Jason Fried, Tetris, Bullshit Jobs: A Theory by David Graeber, Elon Musk and Twitter, the Dunbar number, Zappos, Google, Adam Smith, Stripe, Meta, Jeff Bezos, Basecamp, Zapier, 1Password, GitHub, SpaceX, private jets, Aesop, the Pagani Zonda, the Porsche Boxster, Lamborghini, Coco Chanel, LeBron James, Hey, Steve Jobs, Michael Arrington and TechCrunch, Y Combinator, Dr. Thomas Sowell,Punished by Rewards by Alfie Kohn, Grit by Angela Duckworth, and LEGO.
Links:
Connect with David
Twitter
LinkedIn
Connect with Joubin
Twitter
LinkedIn
Email: grit@kleinerperkins.com
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm
Rails is having a moment (again) (Interview)
(Includes expletives) David Heinemeier Hansson (DHH), creator of Ruby on Rails and co-owner of 37signals, joined the show to discuss this Rails moment and renewed excitement for Rails. We discuss hard opinions, developers being cooked too long in the JavaScript soup, finding developer joy, the pros and cons of the BDFL, the ongoing WordPress drama with WP Engine, and what’s to come in Rails 8.
Join the discussion
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Featuring:
David Heinemeier Hansson – GitHub, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X
Show Notes:
Rails World 2024 Keynote - David Heinemeier Hansson
What’s New in Ruby on Rails 8
Rails is leaning hard into SQLite right now
The Empowered Programmer (Justin Searls) - Rails World 2024
Kamal - Deploy web apps anywhere
LiteFS - Distributed SQLite
Turso - libsql
RubyGems.org
Automattic is doing open source dirty
Matt’s “Response to DHH”
Capture less than you create
My Freedom of Speech
Open Source and Power with Matt Mullenweg (Rework podcast)
Breaking Camp
Our cloud-exit savings will now top ten million over five years
Something missing or broken? PRs welcome!
25 Years Of Founder WISDOM In 55 Minutes (ft. Jason Fried)
Episode 593: Sam Parr ( https://twitter.com/theSamParr ) and Jason Fried ( https://x.com/jasonfried ) open up about personal finances, raising kids around wealth and dealing with risk.
—
Show Notes:
(0:00) Sam and Jason play Would You Rather...
(5:15) Loosening the grip on the stick
(12:35) The pale blue dot
(14:03) Why does the businessworld deserve our best lessons?
(18:30) Early days vs. vs. middle days vs later days
(24:47) "A founder's job is to inject risk"
(29:36) “Cool wears off but useful never does”
(31:07) Striking balance with a business partner
(34:14) The value of talking about money
(37:28) Navigating luxury with kids
(40:08) Midwestern values on blast
(43:39) The truth about luck
(46:55) Staying up vs. staying off
(49:45) New insights from old biographies
—
Links:
• [Steal This] Get our proven writing frameworks that have made us millions https://clickhubspot.com/copy
• The Most Important Thing - https://tinyurl.com/9ym3xw5b
• Peter Lynch books - https://tinyurl.com/2nf87pzb
• The Pale Blue Dot - https://www.planetary.org/worlds/pale-blue-dot
• The Messy Middle = https://tinyurl.com/2paw5jmk
• Sam’s List - http://samslist.co/
• Newspapers.com - http://newpapers.com/
• Pessimists Archive - https://pessimistsarchive.org/
• Grab HubSpot's free AI-Powered Customer Platform and watch your business grow https://clickhubspot.com/fmf
—
Check Out Sam's Stuff:
• Hampton - https://www.joinhampton.com/
• Ideation Bootcamp - https://www.ideationbootcamp.co/
• Copy That - https://copythat.com
• Hampton Wealth Survey - https://joinhampton.com/wealth
—
Check Out Shaan's Stuff:
Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd
My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano
The Cashflow King: “Here’s How I Do It”, Negotiating w/ Jeff Bezos, Elon’s Cracked Rocket - Jason Fried
Episode 564: Shaan Puri (https://twitter.com/ShaanVP) and Sam Parr (https://twitter.com/theSamParr) talk to Jason Fried about his 6-Week Sprint playbook, how he’s planning for the end of subscription revenue, and what it’s like to have Jeff Bezos as an investor.
Want to see Sam and Shaan’s smiling faces? Head to the MFM YouTube Channel and subscribe - http://tinyurl.com/5n7ftsy5
—
Show Notes:
(0:00) Intro
(2:30) Long term planning is a fantasy
(8:30) The 6-Week Sprint Playbook
(14:00) Does Jason regret selling We Work Remotely?
(16:00) Cash flow king
(21:00) Taking money from Jeff Bezos
(29:30) Who does Jason admire?
(33:00) Non-recurring revenue is back
(37:00) The Founder Letter Launch strategy
(45:30) Campfire v. Slack
(50:40) Pile on the wackier stuff early (in life and business)
(53:30) Taking financial risks that don't put you at risk
(57:00) Where does Jason spend his profits?
—
Links:
• Jason on Twitter - https://twitter.com/jasonfried
• Rework - https://tinyurl.com/38mfc66n
• 37Signals - https://37signals.com/
• Basecamp - https://basecamp.com/
• We Work Remotely - https://weworkremotely.com/
• Once - http://once.com/
—
Check Out Sam's Stuff:
• Hampton - https://www.joinhampton.com/
• Ideation Bootcamp - https://www.ideationbootcamp.co/
• Copy That - https://copythat.com
• Hampton Wealth Survey - https://joinhampton.com/wealth
—
Check Out Shaan's Stuff:
Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd
My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano
Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more.
—
Other episodes you might enjoy:
• #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits
• #209 Gary Vaynerchuk - Why NFTS Are the Future
• #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto
• #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett
• #218 - Why You Should Take a Think Week Like Bill Gates
• Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More
• How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More
Jason Fried challenges your thinking on fundraising, goals, growth, and more
Jason Fried is the co-founder and CEO of 37signals, the maker of Basecamp and HEY. 37signals is a very different kind of company. With fewer than 80 employees, they have over 100,000 customers, generate tens of millions of dollars in profit each year, and have no investors, board, or any plans to ever raise money or sell the company. In our conversation, we explore a path many tech founders never consider—bootstrapping. We discuss:
• Why he and his team prioritize profit above all else
• The unexpected challenges with raising venture capital
• The “Shape Up” framework for building products
• Why, and how, to foster a gut-driven culture
• Jason’s thoughts on why work should not feel like war
• Advice for starting a bootstrapped business
• The philosophy behind Once, 37signals’s new line of software products
—
Brought to you by Coda—Meet the evolution of docs | Sidebar—Accelerate your career by surrounding yourself with extraordinary peers | Wix Studio—The web creation platform built for agencies
—
Find the full transcript at: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking
—
Where to find Jason Fried:
• X: https://twitter.com/jasonfried
• LinkedIn: https://www.linkedin.com/in/jason-fried/
• Email: jason@hey.com
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Jason’s background
(03:49) The success of 37signals
(06:46) When raising money makes sense
(09:58) The power of small teams
(13:55) Defining success and goals
(17:08) Playing “infinite games” in life
(20:11) Starting a business vs. staying in business
(22:13) Lessons from 25 years in business
(27:28) Venture scale vs. bootstrapping
(30:30) Choosing the right path for your business
(33:19) The “Shape Up” framework
(37:59) The drawback of promises
(39:56) Adopting a new way of working
(41:36) The two-week cooldown
(43:53) Trusting intuition and gut
(46:41) Creating a gut-driven culture
(49:44) What Jason looks for in new hires
(56:19) Advice on making changes and adapting
(01:00:06) What Jason has changed his mind about
(01:02:33) Planning in 6-week stretches and figuring it out as you go
(01:06:43) Being proud of the work you do
(01:09:05) Jason’s thoughts on why work should not feel like war
(01:11:31) Advice for starting a bootstrapped business
(01:14:33) You must be at peace with the worst that can happen
(01:15:42) The benefits of bootstrapping
(01:19:11) The value of constraints in business
(01:22:00) Jason’s philosophy: “Just keep making great s**t”
(01:23:19) Once, 37signals’s new line of software products
(01:26:33) The philosophy behind Once
(01:35:47) Closing thoughts
(01:37:23) Lightning round
—
Referenced:
• 37 Signals: https://www.smartsheet.com/
• Basecamp: https://basecamp.com/
• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713/
• Ingram Micro: https://www.ingrammicro.com/
• Once: https://once.com/
• Basecamp’s Shape Up framework: https://basecamp.com/shapeup
• Hill charts: https://basecamp.com/features/hill-charts
• Jason Fried’s quote about long-term business planning: https://medium.com/@farkhan569/unless-you-are-a-fortune-teller-long-term-business-planning-is-a-fantasy-jason-fried-quote-a69e8778e9c4
• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/
• Matt Mullenweg on X: https://twitter.com/photomatt
• Leo Polovets on X: https://twitter.com/lpolovets
• HEY: https://www.hey.com/
• Redefining success, money, and belonging | Paul Millerd (The Pathless Path): https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/
• It Doesn’t Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780
• Squarespace: https://www.squarespace.com/
• Stoic negative visualization: https://dailystoic.com/premortem/
• Linear: https://linear.app/
• Peter Rahal on LinkedIn: https://www.linkedin.com/in/peter-rahal-037bba43/
• RXBAR: https://www.rxbar.com/en_US/home.html
• Jason’s LinkedIn post: https://www.linkedin.com/posts/jason-fried_just-keep-making-great-s**t-keep-your-costs-activity-7130978623523614720-VBGX/?trk=public_profile
• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413
• Hell Yeah or No: What’s Worth Doing: https://www.amazon.com/Hell-Yeah-No-whats-worth/dp/1988575117/
• Home-Made: Contemporary Russian Folk Artifacts: https://www.amazon.com/Home-Made-Contemporary-Russian-Folk-Artifacts/dp/0955006139
• Oppenheimer: https://www.oppenheimermovie.com/
• Tom Petty’s “Crawling Back to You” on Spotify: https://open.spotify.com/track/1JenqZNMU6unIwVWmoP3J0
• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
David Heinemeier Hansson (DHH) on the ‘Post-SaaS era' | E1856
This Week in Startups is brought to you by…
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Today’s show:
DHH joins Jason to discuss a post-SaaS world and Once.com (2:29), the evolving landscape of remote work (21:31), navigating internal culture struggles at Basecamp (32:53), and much more!
*
Timestamps:
(0:00) DHH joins Jason
(2:29) David discusses his new SaaS alternative Once.com, which charges a one-time fee rather than a recurring subscription
(10:44) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist
(11:50) David's philosophy on copyrighting
(20:17) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist
(21:31) The evolving landscape of remote work
(31:46) Equinix - Join the Equinix Startup Program for up to $100K in credits and much more at https://equinixstartups.com
(32:53) The state of fundraising and DHH recounts Basecamp's internal culture struggles
(49:03) Should AI progress should be accelerated or slowed down?
(1:08:08) How willful exposure to hardship can build grit and resilience.
*
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
*
Check out Once: https://once.com
*
Follow David:
https://twitter.com/dhh
https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/
*
Follow Jason:
Twitter: https://twitter.com/jason
Instagram: https://www.instagram.com/jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
*
Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
*
Subscribe to the Founder University Podcast: https://www.founder.university/podcast
20VC: Why Financial Planning and Goals Do Not Work, The Decision to Ban Politics in the Workplace and Losing 1/3 of the Team Overnight & The One Question That Will Drive All Decision-Making for Leaders with Jason Fried, CEO @ 37Signals
Jason Fried the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Over an incredible 21-year journey, Jason and his co-founder David have scaled Basecamp to become the communication tool trusted by millions. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few.
In Todays Episode with Jason Fried We Discuss
1. From Web Design Agency to Founding Basecamp:
What was the a-ha moment for Jason when they had to make the pivot from a design agency to going full-time launching and running Basecamp as a SaaS company?
What is Jason running towards? What is he running from?
What is the single biggest fear that Jason is trying to avoid?
2. Jason Fried: The Leader:
Why does Jason believe he is running from his position as leader and CEO @ Basecamp?
Why does Jason not like or agree with goals or targets? Why are they not helpful?
How does Jason make decisions today as a leader and CEO? What one question does he ask that determines his decision-making process?
Why does Jason never compare himself to the competition? Why does he believe competition is for losers?
3. Jason Fried: The Politicisation of Leadership:
Why did Jason and David decide to not allow politics in the workplace?
How did they manage with 1/3 of their team leaving overnight? How was that experience for them personally? How did it impact the company? Is there anything they would do differently?
Does Jason believe we will see the continued politicization of leadership in the coming months?
How would Jason advise other CEOs when it comes to taking a stance on politics?
4. Jason Fried: Building the Best Team:
What is the one question that determines whether you made a good hire?
Why does Basecamp start with hiring all employees on a week-long project contract?
Why does Jason believe the best CEOs approach management as the art of the individual?
5. Jason Fried: The Partner, Father, and Husband:
Jason and David have been partners for 21 years, why does Jason believe it is helpful that they do not see each other much?
Is it right for co-founders and partners to be friends?
What have been Jason's single biggest lessons on what it takes to be the best husband?
What does great fatherhood mean to Jason? How has it changed over time?
108 - I Was Wrong, We Need Crypto | DHH
David Heinemeir Hansson is the Co-Founder of Basecamp & HEY. DHH is a best-selling author, technologist—responsible for creating Ruby on Rails—and a recent crypto skeptic, turned crypto-curious experimenter.
DHH recently wrote a viral blog post titled, “I Was Wrong, We Need Crypto” in which he explains why he’s skeptical of crypto, what ultimately changed his mind, and how he’s thinking about the future of the space going forward.
It’s not every day Bankless brings on a crypto skeptic, but DHH is different. He provides a balanced—well thought out perspective on what the current state of crypto is and what needs to change to make it go mainstream.
------ ✨ DEBRIEF ✨ | Ryan & David's Unfiltered Thoughts on the Episode https://shows.banklesshq.com/p/debrief-i-was-wrong-we-need-crypto
------ 📣 OPOLIS | Sign Up to Get 1000 $WORK and 1000 $BANK https://bankless.cc/Opolis
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------ Topics Covered:
0:00 Intro 6:20 Who is DHH 14:02 Crypto Observations 17:00 DHH’s Top Crypto Skepticisms 29:55 How to be Wrong About Things 37:00 What Changed DHH’s Mind 45:50 Pushback on DHH’s Post 52:50 The Release Valves 1:02:00 New Skills Needed 1:11:20 Other Crypto Rabbit Holes 1:17:44 Russian Sanctions 1:24:50 What Crypto Can Do Better 1:29:50 What’s Next in Crypto For DHH 1:33:50 Closing & Disclaimers
------ Resources:
DHH on Twitter: https://twitter.com/dhh
DHH’s Website: https://dhh.dk
Episode #55: https://www.youtube.com/watch?v=JpzFU7MW5y4
DHH Books: https://www.goodreads.com/author/show/23587.David_Heinemeier_Hansson?from_search=true&from_srp=true
I Was Wrong We Need Crypto: https://world.hey.com/dhh/i-was-wrong-we-need-crypto-587ccb03
----- Not financial or tax advice. This channel is strictly educational and is not investment advice or a solicitation to buy or sell any assets or to make any financial decisions. This video is not tax advice. Talk to your accountant. Do your own research.
Disclosure. From time-to-time I may add links in this newsletter to products I use. I may receive commission if you make a purchase through one of these links. Additionally, the Bankless writers hold crypto assets. See our investment disclosures here: https://newsletter.banklesshq.com/p/bankless-disclosures
DHH on Basecamp's painful evolution, Bitcoin, Revitalizing internet discourse + Lumanu CEO Tony Tran | E1394
Jason chats with David Heinemeier Hansson (2:03) about global governments reacting to COVID, Basecamp’s Twitter cycle blowup last spring when more than 1/3 of the company left, the shift from debating in the public square (Twitter) to debating in private with friends on group chats. We also talk about why David now sees a case for Bitcoin after Canada leans toward authoritarianism.
(00:00) Jason and Molly intro today’s episode, David Heinemeier Hansson, OK Boomer with Tony Tran of Lumanu
(02:03) Jason catches up with David Heinemeier Hansson
(07:05) DHH on Living in Denmark during COVID
(10:31) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist
(11:41) Social media: a weapon of mass disfunction
(20:08) Eight Sleep - Go to https://eightsleep.com/twist to check out the Pod Pro Cover and get $150 off at checkout!
(21:40) DHH on keeping politics out of the workplace and offering severance for company culture unity
(31:14) Marlow - Get 15% off your individual or team memberships at https://getmarlow.com/twist
(32:41) Jason and DHH on the joys of working at home
(39:41) Jason and DHH discuss the downsides of social media
(46:50) Why DHH changed his position on cryptocurrency and the Canadian trucker protests
(01:34:15) Jason, Molly, and Rachel intro this week’s OK Boomer
(01:36:02) Rachel speaks with Tony Tran, CEO of Lumanu
Read David's Blog: https://world.hey.com/dhh
FOLLOW David: https://twitter.com/dhh
Check out Lumanu: https://www.lumanu.com/
FOLLOW Tony: https://twitter.com/TonyTranNYC
FOLLOW Rachel: https://twitter.com/_rachelbraun
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood
#253 — Corporate Courage
Sam Harris speaks with Jason Fried about the recent controversy over the "no politics" policy at his company Basecamp. They discuss his business philosophy, the surrender of institutions to "social-justice" activism, how politics has acquired a religious fervor, some of the cultural risks of remote work, keeping activists out of one's company, social media use as analogous to smoking cigarettes, antitrust regulations for big tech, how social media might be improved, the tax-avoidance schemes of the richest Americans, the prospect of implementing a wealth tax, and other topics.
If the Making Sense podcast logo in your player is BLACK, you can SUBSCRIBE to gain access to all full-length episodes at samharris.org/subscribe.
Learning how to train your mind is the single greatest investment you can make in life. That's why Sam Harris created the Waking Up app. From rational mindfulness practice to lessons on some of life's most important topics, join Sam as he demystifies the practice of meditation and explores the theory behind it.
20VC: Basecamp CEO Jason Fried on His Relationship To Risk, Money, Vulnerability and Self-Doubt, Fantasising About Being Fired, How To Optimise Decision-Making and Minimising Regret
Jason Fried is the Founder & CEO @ Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22 year journey, they have scaled to over 3.5M accounts and in 2020 they went back to being a multi-product company with the launch of their integrated email client & service, HEY. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few.
In Today's Episode You Will Learn:
1.) How Jason Fried made his way into the world of startups and came to found one of the leading project management and team communications tools in the form of Basecamp?
2.) How does Jason analyse and evaluate his relationship to money? Why does Jason believe that he has this inherent downside protection when it comes to money? How does he structure his personal finances between stocks, cash, crypto etc etc? What have been some of Jason's biggest lessons when it comes to tying happiness to monetary levels?
3.) What does Jason mean when he says, "I have a fantasy of getting fired"? How does Jason think about knowing when is the right time to step away from the business? What would he like to do with that time? How does Jason feel about the challenge of tying his identity to his company? What are the dangers of doing so?
4.) How does Jason approach decision-making frameworks? What does Jason believe is the right way to respond when a decision does not go as planned? Where do many make mistakes here? Does Jason feel regret with decisions? How does Jason try and minimise regret?
5.) How does Jason feel about his biggest insecurities as a leader and CEO today? What are Jason's views on a CEO's ability to have self-doubt and be vulnerable? How have his views on this changed over the years? In what way has having kids impacted Jason's operating mindset? How has it changed what he values and appreciates?
Item's Mentioned In Today's Episode
Jason's Favourite Book: In Praise of Shadows
As always you can follow Harry and The Twenty Minute VC on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
E1099: Basecamp Co-Founder Jason Fried on building Hey, making email exciting again, Hey vs. Apple & more
Check out Hey: https://hey.com
FOLLOW Jason Fried: https://twitter.com/jasonfried
FOLLOW Jason Calacanis: https://linktr.ee/calacanis
Shipping work that matters (Interview)
We’re revisiting Shape Up and product development thoughts with Ryan Singer, Head of Product Strategy at Basecamp. Last August we talked with Ryan when he first launched his book Shape Up and now we’re back to see how Shape Up is shaping up — “How are teams using the wisdom in this book to actually ship work that matters? How does Shape Up work in new versus existing products?” We also talk about the concept of longitudinal thinking and the way it’s impacting Ryan’s designs, plus a grab bag of topics in the last segment.
Join the discussion
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Featuring:
Ryan Singer – Website, GitHub, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X
Show Notes:
The Changelog #357: Shaping, betting, and building
Ryan’s new hobby podcast called Synthetic A Priori
Shape Up (book site)
“Good design requires thinking longitudinally.”
New versus existing products
Taguchi methods on Wikipedia
Salt. Fat. Acid. Heat. - If you can master these four elements, you can master the kitchen.
EconTalk podcast
The End of Average: How We Succeed in a World That Values Sameness
Dr Ole Peters
Time for a Change: Introducing irreversible time in economics by Dr Ole Peters
Something missing or broken? PRs welcome!
Basecamp CTO David Heinemeier Hansson and Rep. David Cicilline on Apple's monopolistic app store fees
Apple is acting like a monopolist and a bully, according to the chairman of the House Antitrust Committee.
Rep. David Cicilline (D-RI) joined The Vergecast along with Basecamp CTO David Heinemeier Hansson to discuss the plight of Hey, Basecamp’s new $99-a-year premium email service. Earlier this week, Heinemeier Hansson revealed that Apple had rejected the Hey iPhone app from the App Store because it didn’t offer any way to sign up and pay in the app itself — which would require giving Apple a 30 percent cut of the fee.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Recode Decode: Jason Fried
Basecamp CEO Jason Fried talks with Recode's Kara Swisher about the company's new email product, Hey, which he describes as "the most ambitious and stupidest thing we’ve ever done." Fried also discusses how coronavirus proved that offices are not as important as other companies used to say, why Zoom calls "suck," and why Basecamp is charging $99/year for a personal Hey account, Plus: Why Uber is a "shitty business," why Fried doesn't want any public CEO's job, and the state of tech regulation.
Featuring:
Jason Fried (@jasonfried), CEO, Basecamp
Host:
Kara Swisher (@karaswisher), Recode co-founder and editor-at-large
More to explore:
On Reset, Arielle Duhaime-Ross explores why — and how — tech is changing everything.
On Recode Media, Peter Kafka interviews business titans, journalists, comedians and podcasters about the collision of tech and media.
On Pivot, Kara Swisher and Scott Galloway talk about the big tech news stories of the week, who's winning, who's failing, and what comes next.
And on Land of the Giants, Jason Del Rey chronicled the rise of Amazon. Season 2 will focus on Netflix and is coming soon!
About Recode by Vox:
Recode by Vox helps you understand how tech is changing the world — and changing us.
Follow Us:
Newsletter: Recode Daily
Twitter: @Recode and @voxdotcom
Learn more about your ad choices. Visit podcastchoices.com/adchoices
20VC: Basecamp Founder David Heinemeier Hansson on Why It Is The Biggest BS To Chase Being A Unicorn, His Relationship to Wealth and Status and Why Now More Than Ever It Is A Myth Entrepreneurs Have To Raise VC
David "DHH" Heinemeier Hansson (@dhh) is the creator of Ruby on Rails, founder and CTO at Basecamp (formerly 37Signals), and the best-selling co-author of Rework and Remote: Office Not Required. If that was not enough, fun fact, he went from not having a driver's license at 25 to winning, at 34, the 24 Hours of Le Mans race, one of the most prestigious automobile races in the world. It is often called the "Grand Prix of endurance and efficiency."
In Today's Episode You Will Learn:
1.) How David made his way into the world of tech and startups from his childhood living in Copenhagen and how a cold email led to the founding of Basecamp with Jason Fried?
2.) What have been some of David's core observations as people move to remote work over the last few weeks? What is the #1 mistake that 90% of teams make? How does David advise founders to approach loneliness and depression in their team? What strategies have Basecamp used to unite the team and inspire collaboration and teamwork?
3.) Why have David and Jason always tried to keep the Basecamp team as small as possible? Why does David believe one of the biggest problems is that execs have too much time? How does that manifest itself? What does David's week look like? How does he approach meetings?
4.) Why does David hate the majority of "mission statements" today? What are the best composed of? What are the worst? What feelings does David believe your mission statement should inspire in the reader? What does David believe one needs to do to build a challenger brand today?
5.) Why has David and Basecamp always resisted the conventional path of raising VC funds? Why does David believe needs VC money is total BS? Why does David believe it is BS to chase being a unicorn? Why have founders got this so wrong today and what can they do to change?
6.) How would David describe his relationship to money? How has that relationship changed over time? What are the core challenges as one moves from a monetary to a deeper appreciation of what makes one happy? How did the transition occur for David? How does David advise others in terms of finding their moment for the transition?
Items Mentioned In Today's Show:
David's Fave Book: Erich Fromm: To Have Or To Be
As always you can follow Harry, The Twenty Minute VC and David and on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta's team of experienced fund accountants. Go to carta.com/20vc to get 10% off.
E1029: Basecamp Co-Founder & Author David Heinemeier Hansson (@DHH) debates Jason on reining in capitalism, benefits of state-run education & healthcare, big-tech disappointments, work-from-home paradigm shift, wealth tax & more!
0:56 Jason intros David Heinemeier Hansson (@DHH) and asks about the work-from-home paradigm shift
5:28 Measuring programming success via budgets instead of estimates, quantifying creativity
9:57 Are incentive systems inherently bad?
13:01 How terrible commutes turned the tides for remote work in Silicon Valley, why do executives subject themselves to horrible working conditions?
17:59 What is the optimal amount of work hours per week?
19:58 Benefits of higher minimum wage
23:28 How can America "get to Denmark"? Should we rein in capitalism?
27:19 How do educational stipends work in Denmark? Benefits of state-sponsored education & healthcare
32:27 Is American bureaucracy able to change quickly?
35:52 Are gig workers being exploited? Why or why not?
45:57 Flexibility vs. Security in the gig-economy
51:20 Has the American Dream become false in America?
1:00:26 Are ISA schools (like Lambda School) an innovation or a bandaid on the failing capitalist system?
1:06:30 What do successful numbers look like for ISAs?
1:12:28 Starting Basecamp & raising from Jeff Bezos in the early days
1:19:43 Roasting Jeff Bezos on Twitter, socialism, progressivism in America
1:28:13 Amazon disappointments & how can Bezos save face?
1:36:31 Wealth tax debate
1:43:23 Which major tech companies should be broken up?
1:52:04 Will GDPR-like policies work in America?
1:55:59 What is David doing with Hey.com? Should there be two-sided consent in email read-receipt tracking?
2:03:29 Could there ever be an open-source Twitter or messaging app? Was WhatsApp it before being bought by Facebook?
2:09:34 Thoughts on tech journalism vs. big-tech
2:12:22 Can big-tech regulation fix the competitive landscape?
Why it doesn’t have to be crazy at work with David Heinemeier Hansson
On this episode Abadesi talks to David Heinemeier Hansson, co-founder and CTO of Basecamp, and creator of Ruby on Rails. He is also the author of several bestselling books, including It Doesn’t Have To Be Crazy At Work, co-authored with his co-founder at Basecamp, Jason Fried.
In this episode they talk about...
Why you should think about your company as a product
“This idea that the company itself is changeable — the policies of the company, the values of the companies — are things you can tweak and you can iterate on in much the same way as you would iterate on a product. The process is quite similar to when you put a product into the market and you get feedback from customers.”
He tells the story of building Basecamp outside traditional tech hubs and how that influenced the culture at the company. He says that it’s important to build from first principles and to have control over the company you’re building. He talks about their values at Basecamp and how to think about and get feedback from employees on how the company needs to change and evolve. He also points out that you always need to be thinking about improving not just your product, but also your entire philosophy and way of doing business.
Why we need new role models in tech
“We've gone from everyone thinking the greatest thing in the world would be to be Mark Zuckerberg and to have Facebook to far more people now thinking, actually I don't want Facebook, I don't want Facebook's problems, I don't want to be Mark Zuckerberg. I think if we can start by having a takedown of the past idols, we can start building up some healthier models of what we should try to emulate instead.”
David says that we need a new vocabulary in the tech industry. He lists a number of different words, from unicorn to angel to battlefield, that inaccurately describe the actual function or intent of that entity. He says that it’s easy to excuse unethical actions if we believe that we are actually at war in a startup. He also talks about why “small is not a stepping stone” for your company and breaks down why the obsession with growth has led people astray.
How to break the cycle of overwork
“We can live such better fuller, richer lives if we just stopped believing that the most worthy thing we can do is to give every waking hour and moment to the business. That's actually not good for business. If you were just trying to create the most efficient business, you would not come up with this regime of chaining people to the office.”
He explains why you shouldn’t think about your co-workers as your family, and examines some of the current scourges of modern workplaces, like the open-plan setup. He also points out that Henry Ford realized a long time ago that people cannot work for more than forty hours a week without seeing a huge drop-off in efficiency, so it would make sense not to not push employees harder than that today.
A new way of working
“It doesn't work to constantly puncture and slice up the day [with meetings and standups]. So you should be extremely cautious about when you put things on many people's calendar. When we do instead is we encourage people to share where they are at [on a project] in an asynchronous way where someone can choose to digest that and respond to that on their time.”
David talks about the current practices prevalent at most workplaces that result in people not getting things done, and how they can be improved on. He talks about the unique approach to meetings, standups, deadlines, and presentations that they have at Basecamp and how they have increased retention. He says that it’s a misconception that people are born superstars and says that high-quality talent is more akin to a tree, that you cultivate, rather than a “diamond” that you find.
Of course, they also talk about some of his favorite products as well.
We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. 😸
Companies, Books, and Products Mentioned In This Episode
BreatheSmart Air Purifier — Stylish and effective air purifier.
It Doesn’t Have To Be Crazy At Work by Jason Fried and David Heinemeier Hansson
Oura Ring — Advanced sleep and fitness tracker.
Why We Sleep: Unlocking The Power of Sleep and Dreams by Matthew Walker
How To Ship Work That Matters with Basecamp’s Ryan Singer
On this episode Abadesi talks to Ryan Singer, head of Product Strategy at Basecamp, where he’s worked for 16 years, ever since 2003. He is the author of Shape Up: Stop Running in Circles and Ship Work That Matters. You can read the book for free online.
In this episode they talk about...
How Basecamp cultivates their unique company culture
“If you think something is going to work, then go make it and let’s look at what you made in two or three days or a week. If you can’t make anything yet that works, maybe it’s not real and not ready yet. Don’t make me a big document about how it’s going to work — let’s make a prototype and click on it and see if it’s going to work.”
Ryan says that he was initially a UI designer and got into programming after joining Basecamp. He was at what was then called 37signals when Ruby on Rails was being created. He talks about the culture of shipping at Basecamp and how the learnings from his sixteen years at the company have made it into the book.
Why wireframes and documents are overrated
“If we over-specify the design up front with a lot of wireframes, we make the most decisions when we have the least information.”
Ryan says that at Basecamp, they use breadboards and fat marker sketches to mock up potential products, rather than detailed documents or pixel-perfect wireframes. He explains why it’s important to allow for improvisation by the designers and developers of products, and why you shouldn’t make the key trade-offs in the design phase, but instead after you’ve seen and used a prototype. He says that you “need to find the right level of abstraction” in your designs.
Why betting is better than planning
“We acknowledge the reality, which is that we don’t know what’s going to happen, we don’t know how this is going to work out, we’re probably going to be wrong about some things, so we want to use the language of risk instead of the language of certainty.”
At Basecamp, instead of making plans, they make bets. Ryan explains why this provides a better framework for the work that they do. He points out that when you make bets, you bet a fixed amount. They do the same at Basecamp, “betting” a certain amount of time on a project to see if it will work. If at the end of that time, it didn’t work out, they don’t spend more time than they originally “bet” on it chasing sunk costs.
How to find balance at work, and why Basecamp doesn’t think about “maximizing capacity”
Ryan says that they don’t think about “maximizing capacity” from their employees. Instead, they want to make sure that their workers have a meaningful goal with good odds for success. He says that managing how many hours someone worked the day before or today means very little. His advice is to stop micromanaging employee time and to experiment with a more flexible approach at your company. He also points out that they try to think about strategy at a more macro level than in terms of days or hours.
How to separate strategic failure from execution failure
“I would much rather have a healthy team that’s good at shipping stuff and occasionally make a strategic mistake. Because our bets have a limited downside, we’re setting out how much it is worth at the beginning. We only lose however much time we set out initially.”
As part of their unique approach to strategy, they are able to manage their downside by setting out the amount of time they’re willing to spend on something in the beginning. They trust their teams to figure out the details of the work on their own, without prescribing every detail of the product in the beginning. He explains how this is important to morale and what the difference between “imagined work” and “discovered work” is.
Ryan also talks about his love for the Apple Pencil and the iPad, and how he uses them to get his work done.
Bonus Content: Aba and the community on personal branding
We have more bonus content for you this week! Aba recently hosted a Periscope session where she invited all of you in the community to call in and explain what sites you use for personal branding and why. They covered LinkedIn, Medium, Twitter, personal sites, mailing lists, and more. If you want to be part of the next session (and maybe even be part of the podcast!) be sure to follow us on social media.
We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. 😸
Companies and Products Mentioned In This Episode
iPad + Apple Pencil
The Economist’s Mobile App
Shaping, betting, and building (Interview)
Ryan Singer, head of Product Strategy at Basecamp, joined the show to talk about their newest book — Shape Up: Stop running in circles and ship work that matters. It’s written by Ryan himself and you can read it right now for free online at Basecamp.com/shapeup.
We talked about the back story of the book, how the methodology for Shape Up developed from within at Basecamp, the principles and methodologies of Shape Up, how teams of varying sizes can implement Shape Up. Ryan even shared a special invitation to our listeners near the end of the show to his live and in-person Shape Up workshop on August 28th in Detroit, Michigan.
Join the discussion
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Featuring:
Ryan Singer – Website, GitHub, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X
Show Notes:
Shape Up
Foreword by Jason Fried
Principles of shaping
Example pitches — “How we do it in Basecamp”
Bets, Not Backlogs
How to Begin to Shape Up
Summary of the Shape Up method
Shape Up glossary
Ryan’s tweet about the Shape Up workshop
If you have questions — email shapeup@basecamp.com
Getting Real
All of Basecamp’s books
Something missing or broken? PRs welcome!
#105 – Charting Your Own Course as a Founder with Jason Fried of Basecamp
Jason Fried (@jasonfried) doesn't intend to be controversial or to change people's minds, but he seems to end up doing both of these regardless. Since launching Basecamp in 2004, he's grown the business to tens of millions of dollars in annual *profit*, and gathered a collection of strong and often counterintuitive beliefs along the way. In this episode we discuss how to take advantage of building an independent company, when to focus on a product and when to let it go, how to learn from the past without fooling telling yourself a false narrative, and the importance of blazing your own path as a founder instead of blindly imitating others.
Transcript, speaker information, and more: https://www.indiehackers.com/podcast/105-jason-fried-of-basecamp
Recode Decode: Basecamp CEO Jason Fried
Basecamp CEO Jason Fried talks with Recode's Kara Swisher about his most recent book, It Doesn't Have to Be Crazy at Work, which he co-wrote with his business partner David Heinemeier Hansson.
In this episode: How Basecamp got started; why chat apps like Slack and Basecamp's own Campfire are bad for productivity; the things that make work crazy, including access to coworkers' calendars, ASAP-response culture and codependent departments; why Basecamp does not set any goals internally other than "be profitable"; how Silicon Valley's "world domination mindset" stresses workers out; which tech exec would win in a fight?; the fakeness of fancy office perks; the problems with serial entrepreneurship, best practices and intentional sleep deprivation; "hacking anything is stupid"; why venture capital destroys more businesses than it helps; and how tech companies are trying to avoid becoming Philip Morris.
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#329: Jason Fried — How to Live Life on Your Own Terms
Jason Fried (@jasonfried) is the co-founder and CEO at Basecamp, and the co-author of Rework, Remote: Office Not Required, and Getting Real: The Smarter, Faster, Easier Way to Build a Successful Web Application. The upcoming It Doesn't Have to Be Crazy at Work will be out later this year.
Jason writes a regular column for Inc. magazine and is a frequent contributor to Basecamp's popular blog Signal v. Noise, which offers "strong opinions and shared thoughts on design, business, and tech."
Enjoy!
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***
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JavaScript sprinkles in Basecamp turned Stimulus (Interview)
David Heinemeier Hansson joined the show to share the story of how JavaScript sprinkles in Basecamp evolved into a full-fledged framework called Stimulus. We talked about ins and outs of Basecamp as it is today, Ruby, JavaScript and David’s somewhat new found love for that language. How they open source because they can. And David’s new YouTube series called “On Writing Software Well”.
Join the discussion
Changelog++ members support our work, get closer to the metal, and make the ads disappear. Join today!
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Featuring:
David Heinemeier Hansson – GitHub, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X
Show Notes:
Stimulus homepage and the source on GitHub
Stimulus 1.0
Turbolinks
Watch the proposition of Turbolinks if you haven’t yet
David’s thoughts on the majestic monolith
Something missing or broken? PRs welcome!
#203: David Heinemeier Hansson on Digital Security, Company Culture, and the Value of Schooling
David "DHH" Heinemeier Hansson (@dhh) is the creator of Ruby on Rails, founder and CTO at Basecamp (formerly 37signals), and the best-selling co-author of Rework and Remote: Office Not Required. Oh, and he went from not having a driver's license at 25 to winning, at 34, the 24 Hours of Le Mans race, one of the most prestigious automobile races in the world. It is often called the "Grand Prix of endurance and efficiency." Listeners had a million questions we didn't get to last time, so he's back for round two because his episode is about to cross a million downloads -- and that's in barely two weeks! In this episode, DHH discusses: Digital security The value of schooling Three questions you should be able to answer Company culture How bladder relief happens in a 24-hour race And much, much more! Please enjoy my round 2 conversation with DHH! Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast. This podcast is 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 4-Hour Body, 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. This podcast is also brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service led by technologists from places like Apple. It has exploded in popularity in the last two years and now has more than $2.5B under management. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it's all through smarter software instead of retail locations and bloated sales teams. Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they'll show you for free the exact portfolio they'd put you in. If you want to just take their advice and do it yourself, you can. Well worth a few minutes to explore: wealthfront.com/tim.
***
If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!
For show notes and past guests, please visit tim.blog/podcast.
Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.
For transcripts of episodes, go to tim.blog/transcripts.
Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.
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Follow Tim:
Twitter: twitter.com/tferriss
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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.
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