Courtland founded Indie Hackers, one of the leading entrepreneurship communities on the internet.

Indie Hackers was acquired by Stripe in 2017. He's a Y Combinator alum & graduated from MIT.

This conversation is broken up into two parts.

In part one, we discuss:

• the indiehacker philosophy
• optimizing for freedom + becoming a time billionaire
• capitalism + the american dream
• diversity, race + culture
• equality of opportunity vs outcome

Part Two - Business Idea Framework (starts at 1hr mark):

• a four-step framework for brainstorming business ideas
• difference between product ideas + business ideas
• how to think about distribution from day one
• finding a door before making a key
• how to create an innovative solution

Timestamps:

• 00:00:00 Intro
• 00:02:52 Who is Courtland + what is Indie Hackers
• 00:04:24 Background + Getting Acquired By Stripe
• 00:09:51 Differentiating
• 00:12:47 Unbundling Platforms + Creating Alternatives
• 00:16:03 Experience at Y Combinator
• 00:21:49 The Indiehacker Philosophy
• 00:25:02 "The Time Billionaire"
• 00:27:20 Skin In The Game
• 00:31:11 The Evolution of Capitalism
• 00:36:04 Equality of Outcome vs Equality of Opportunity
• 00:39:28 Objective Thinking + Confirmation Bias
• 00:41:40 Going Beyond Performative Diversity
• 00:44:32 The Nuance of Culture vs Race
• 00:51:10 The Value of Examples
• 00:54:48 Getting To The Root Of The Problem
• 00:59:13 Does The American Dream Exist?

Part Two: Business Idea Framework:

• 01:03:44 4 Part Framework: Problem, Distribution, Monetization, Solution
• 01:04:58 Product Idea vs Business Idea
• 01:06:38 What Makes A Good Problem?
• 01:08:53 Tribes, Channels + Distribution
• 01:14:17 Courtland's Checklist To Evaluate Problem
• 01:18:18 Where to Look for Problems
• 01:20:29 Sources To Find Rising Trends
• 01:25:23 Distribution From Day One
• 01:27:12 How To Share On Indie Hackers
• 01:32:55 Doing It Well vs Perfectionism
• 01:34:48 Wrap-Up

Tim Urban is one of the internet's most popular writers.

His blog, Wait But Why, attracts millions of visitors including famous fans like Elon Musk. His talk on procrastination is the #1 TED talk on YouTube with 33mil+ views.

Subscribe + Watch on YouTube:
https://youtu.be/tl2a6H1E7DU

Let us know what you think on Twitter:
@bzaidi
@waitbutwhy

FIVE THINGS YOU'LL LEARN:

1. his writing + research process
2. first principles thinking + lessons learned from Elon Musk + Tony Hseih (Zappos)
3. techniques to overcome low confidence + find your authentic voice
4. how he'd start from scratch today
5. how to explain complex topics like AI + Neuralink through storytelling

SHOW NOTES + TRANSCRIPT:
https://www.creatorlab.fm/tim-urban-wait-but-why-podcast/

TIMESTAMPS:

• 00:00:00 Preview
• 00:02:05 Intro + Tim’s Cuddly Toys
• 00:04:38 How Elon Musk Became A Fan
• 00:05:33 11yr Old Tim Meets The Internet
• 00:07:17 Trip Down Internet Memory Lane
• 00:09:39 “Underneath The Turban” + Finding A Creative Path
• 00:14:07 Micro + Macro Happiness
• 00:15:22 Finding A Voice + Getting Traction
• 00:17:39 “What Could I Do With 60hrs A Week?”
• 00:19:04 Tim’s Research + Writing Process
• 00:25:33 “Neuralink Is A Magic Hat”
• 00:26:53 Tools + The Magic of “Text Edit”
• 00:31:53 Talent vs Craft
• 00:34:12 “Writing For a Stadium Full of Tim’s”
• 00:36:42 Adam Grant’s Antidote to Paranoia
• 00:38:47 Vicious Cycle of Confidence
• 00:42:07 Headlines
• 00:45:36 Example: Fermi Paradox
• 00:47:58 Creativity vs Promotion
• 00:50:33 Starting From Scratch Today
• 00:51:51 Facebook Ads In 2013
• 00:53:57 Owned, Rented + New Platforms
• 01:01:01 Dream Person To Interview
• 01:03:37 First Principles + Learning From Elon Musk
• 01:08:37 Manage A Business Like Elon Musk
• 01:10:37 Latest on Neuralink + AI
• 01:15:37 Re-Thinking A Cyborg From First Principles
• 01:16:23 Memories + Lessons From Tony Hseih (Zappos)
• 01:22:19 Tony Hseih’s Relationship Ripple Effect

Let me know what you think on Twitter: @bzaidi

Subscribe + watch on YouTube:
https://youtu.be/jWYhsGaK3Qk

Chris Kuenne started Rosetta & grew it to become the largest independent digital agency in the world before selling to Publicis for $575mil.

Now he runs Rosemark Capital, investing in companies with revenues of $30–60mil. Chris teaches high-tech entrepreneurship at Princeton University.

In this conversation, we discuss:

• how Chris pre-sold $1mil of contracts before launching his agency
• four personality types of builders
• the opportunity to solve expensive problems + merge software with services
• how acquisitions fueled growth before selling for $575mil
• lessons in hiring 1200+ people
• breaking down implications of money raised + liquidation in his sale

TIMESTAMPS:

• 00:00:00 Intro
• 00:02:23 Behind A $575M Deal
• 00:07:08 What Would You Do Differently?
• 00:11:01 Turning Down A Larger $600M Offer
• 00:13:49 How Much Does A Founder Keep After A Huge Sale?
• 00:19:18 Venture Waterfall + Preference Stack
• 00:22:13 What Changed After the Deal
• 00:26:45 Early Years At Rosetta
• 00:31:22 Pre-Selling $1mil In Sales Before Quitting His Job
• 00:34:55 Find An Expensive Problem - The Mckinsey Approach
• 00:38:36 Expensive Problems To Work On In 2021
• 00:41:27 Using Data To Create A Quantitative Persona
• 00:43:21 Opportunities To Combine Software + Services
• 00:45:35 Who's Doing It Well In SaaS?
• 00:50:01 Lessons In Hiring 1200+ People
• 00:56:40 The Right Way To Fire Someone
• 00:59:19 4 Builder Personalities: Driver, Explorer, Crusader + Captain
• 01:01:04 The Driver: Apple
• 01:03:44 The Explorer: Facebook
• 01:04:52 The Crusader: Google
• 01:05:50 The Captain: Alibaba
• 01:08:11 Wrap Up

Matteo Franceschetti is the founder of Eight Sleep, the sleep fitness company at the forefront of sleep tech.

They’ve raised more than $70mil, came out of Y Combinator and are one of the leading companies at the forefront of sleep technology.

Time magazine named their product one of the best inventions of 2018 + 2019.

Watch + subscribe on YouTube:
https://youtu.be/vd3wXxYaAxc

Let us know what you think on Twitter:
https://twitter.com/bzaidi
https://twitter.com/m_franceschetti

In this conversation, you'll learn:

• how they’re using AI + machine learning to improve sleep
• the challenges of building hardware + software (smart mattress)
• unit economics you should think about when launching a DTC brand
• future plans to control oxygen levels, humidity + light to improve sleep
• balancing organic growth vs paid acquisition
• successfully partnering with influencers
• actionable ways to improve deep + REM sleep

TIMESTAMPS:

• 00:00:00 Intro
• 00:03:07 What Is Eight Sleep?
• 00:04:34 Coming To America
• 00:08:01 4 Factors To Improve Health + Sleep
• 00:09:49 How To Start a DTC Company
• 00:12:05 Indiegogo Launch + Raising Money
• 00:13:07 Focusing On Thermal Regulation
• 00:14:10 Future Of Sleep Technology
• 00:15:58 Brand Partnerships
• 00:17:01 Using AI + Machine To Improve Sleep
• 00:18:02 Temperature's Impact On Sleep
• 00:21:14 Marketing a DTC Product
• 00:22:46 Organic Growth + Influencers
• 00:23:24 Balancing Paid Acquisition + Organic Growth
• 00:27:04 Reverse Engineering + Diminishing Returns
• 00:30:59 Measuring Word Of Mouth + 7 Touchpoints Rule
• 00:32:27 DTC Unit Economics
• 00:34:06 Peloton, Tesla + Price Sensitivity
• 00:37:38 Pros + Cons of Going Public
  
  
• 00:40:42 How To Get Better Sleep
• 00:42:30 Stages of Sleep: Light, Deep + REM
• 00:44:32 Sleep's Impact On Hormones + Junk Food
• 00:45:42 Factors To Improve Sleep
• 00:49:24 Stop Your Mind Racing
• 00:52:19 Caffeine + Alcohol
• 00:54:50 3 Roles Of A CEO
• 00:58:55 Board Meetings + Close