My First Million Podcast

Episode Title: DHH: $100M+ Advice That’ll Piss Off Every Business Guru
Hosts: Sam Parr, Shaan Puri, Sean Ogle
Guest: David Heinemeier Hansson (DHH), co-founder of Basecamp & 37signals
Release Date: March 17, 2026

Episode Overview

In this episode, Sam Parr and Sean Ogle sit down with David Heinemeier Hansson (DHH)—the outspoken co-founder of Basecamp (37signals), creator of Ruby on Rails, and Le Mans race car driver—for an unfiltered masterclass in building enduring, profitable businesses while rejecting Silicon Valley dogmas. DHH shares war stories, reflects on both his successes and high-profile missteps, and gives candid advice on everything from the role of ignorance in innovation, to why "grinding" is a trap, to the philosophy that "nobody knows anything." The conversation is both refreshingly irreverent and deeply insightful—packed with contrarian advice, business history, and honest takes that challenge the status quo.

Key Discussion Points & Insights

1. DHH’s Multifaceted Background and Philosophy

DHH on His Identity (00:14)
- DHH adapts his introduction based on audience: car enthusiasts get Le Mans stories, programmers hear about Ruby on Rails, entrepreneurs get Basecamp/37signals.
- Quote:
  
  "If I'm talking to a bunch of car nerds, I talk about winning Le Mans. If I talk to a bunch of programmers, it's all about Ruby and Rails. And if a bunch of entrepreneurs, it's usually about building Basecamp and 37signals."
  — DHH (00:23)
Philosophy Over Features (01:36)
- 37signals’ website features a 1999-style 'manifesto'—a compilation of raw, old-school chapters outlining their beliefs.
- "A lot of it is simply based in the fact that neither Jason or I can shut up about what we believe." — DHH (02:45)
- Fundamental approach: out-teach, not outspend competitors.
The Privilege of Privacy (00:39, 27:08)
- 37signals has never revealed full revenues/profits (described only as "ridiculous")—a luxury enabled by being private and profitable.

2. Teaching Before You're “Qualified”—Imposter Syndrome & Ignorance as Strength

Imposter Syndrome and Out-Teaching (07:21)
- Sam admits initial hesitation to give advice since others are more successful.
- DHH credits a “completely irreverent personality” and the drive to internalize by teaching.
Liquid vs. Crystallized Intelligence (09:58)
- Younger people have “liquid intelligence”—speed, boldness, and “productive ignorance.”
- Quote:
  
  "Ignorance is a benefit for a huge class of problems...you will be locked into paradigms and thought patterns. If you want to break those paradigms, you kind of got to start from a clean slate."
  — DHH (12:28)

3. How Constraints Sparked Creativity & Ruby on Rails

Dot-Com Bust as Crucible (12:28–16:23)
- Lack of cash forced DHH and Jason to be scrappy—using open source tools, handling everything in-house.
- Quote:
  
  "I could not use the same technology as everyone else was using, because I had a tenth, a hundredth, a thousandth of the capacity. Therefore, I had to use something else...And this in my case...was the birth of Ruby on Rails."
  — DHH (15:47)

4. Taste vs. Data—Why They Ignore A/B Tests

Taste Over Metrics (24:58–32:21)
- Despite legendary copywriting (e.g., hey.com), DHH and Jason “never really looked at conversion rates.”
- Quote:
  
  "I've never really thought about it. I just know that it felt good and I think it's good. Therefore we just ran with it."
  — Jason Fried (relayed by Sam, 25:10)
- They eventually dropped most analytics and A/B testing:
  
  "After trying that for over a decade...we never did what the numbers told us to do. We would do whatever the hell we wanted to do."
  — DHH (27:53)
The Luxury of Margins and Freedom (26:17)
- High profitability meant they could ignore the grind, focus on what energized them, and dismiss standard productivity dogma.
- "Grinding is the stupid shit you do in World of Warcraft when you're peon. No, thank you. I don't want to do that."
  — DHH (28:42)

5. Humility—Learning from Being Wrong

The Facebook $33 Billion “Miss” (18:03–24:58)
- DHH famously wrote that Facebook “wasn’t worth $33B” in 2010. In hindsight, Facebook proved him wrong—he owns it, and uses it as a lesson in humility and “resulting.”
- "You should have some humility about your predictions."
  — DHH (24:42)
- On evaluating luck vs. process:
  
  "[In poker] the way to win...is to make sure you predominantly play hands that have the best odds...if you go all in on a hand that has 87% odds...and you lose, you’re an idiot if you draw the conclusion that you shouldn’t have gone in on that hand. Totally should have."
  — DHH (20:47)

6. Context Matters—Why There’s No Universal “Wisdom”

Contextual Nature of Advice (32:36–34:12)
- DHH critiques “wise axioms” as context-bound; what works for a small startup may not for a behemoth like Shopify.
- "For every wise axiom, you can find another that says the opposite. That also sounds wise."
  — DHH (32:36)

7. Lessons from the Shopify Board

Nobody Knows Anything (34:12–36:16)
- DHH describes joining Shopify’s board as an awe-inspiring learning experience—yet, admits even board members can't truly explain massive growth.
- "Nobody knows anything...we can have all these theories. Very, very little of it gets to be reduced to irrefutable proof in the sense of a math equation."
  — DHH (35:30)
Tobi Lütke’s Unique Leadership (36:16–38:38)
- Tobi remains a “computer nerd” at heart, with deep technical curiosity and future-driven vision. His conviction often ran counter to industry consensus—sometimes being “right a lot” simply by checking facts others miss.

8. DHH’s Evolution on AI

AI Skepticism to Full Enthusiast (41:35–47:34)
- Initially fascinated but dissatisfied with AI’s code quality and annoyances, DHH’s attitude fundamentally shifted with the arrival of state-of-the-art models in late 2025.
- Quote:
  
  "The last three months...have been the most churn in my mental approach to computers...now I’m in the herd...the agents are incredibly capable programmers."
  — DHH (45:58)

9. What's Changed Since 37signals’ Early Days

Building Audiences No Longer Converts Like It Used To (48:45–51:53)
- The classic "jab, jab, jab, right hook" content model is breaking down—algorithms increasingly throttle company reach, meaning audiences don't guarantee business.
- "I'm not sure our historic long run strategy of build a large audience and then good things will happen is necessarily true anymore."
  — DHH (50:34)
Still, Teaching is Worthwhile for Personal Growth
"It's actually how you learn more...when you try to teach what you've internalized, you make it sink in deeper."
— DHH (51:28)

10. Influences, Role Models & Work-Life Philosophy

On Inspiration and Side-Quests (53:16–60:22)
- Early on, DHH’s blueprint was “find people I like and copy their motions” even without fully understanding them.
- Ricardo Semler (author of Maverick) gave permission to break industrial norms.
- Kent Beck (Extreme Programming) showed how to challenge tech orthodoxy.
- Matz (Ruby’s creator) reframed programming with “programmer happiness” as a priority.

Quote on Lasting Companies: (62:20)

> "The number one objective both Jason and I [have] is to ensure that 37signals is still a place we want to work...Not just want to work, but like to work."  
— DHH (62:20)

On Avoiding Burnout and Stress (64:31–66:14)
- Early profits and financial success gave DHH margin and detachment:
  
  “We just reached [financial stability] quite early...So now I’m in fluffy land. If this ends tomorrow, I can be at peace with the whole thing...The vast majority of anxiety that wreck entrepreneurs...are about forces outside of their control. The best you can do is the best you can do.”
  — DHH (65:10)

11. The Legendary "Hey.com vs. Apple" Story

Battling Apple Over App Store Fees (69:34–75:52)
- Apple tried to enforce a 30% revenue cut for "Hey" iOS app access—DHH and Jason refused, enduring a high-stress, public showdown. Their principle: if you're not selling via the app, Apple shouldn't get a cut.
- "I would rather burn down millions of dollars to build over two years than to pay the gangster shakedown."
  — DHH (71:27)
- Ultimately, Apple bent, re-writing the rules to fit an exemption for Hey.
Philosophy: No-Permission Tech
"If I publish a website on the Internet...I get to do it. I don't have to ask anyone for permission. There’s a little bit more permission these days, but...no permission tech, no permission platform. This is what me likes."
— DHH (73:25)

Notable Quotes & Memorable Moments

On Advice and Originality:

“Neither Jason nor I have been in Silicon Valley...which meant that original thought was possible.”
— DHH (05:25)
On the “Myth” of Data-Driven Everything:

“Maybe all the statistical analysis is a bit of hocus pocus...the missing ingredients to getting to the capital T truth is unknown.”
— DHH (31:03)
On Shopify’s “Glitch in the Matrix” Growth:

“Shopify last year grew almost 30% year over year. I would’ve been happy to grow 30% year over year...at the board, even Toby, we don’t really know [why].”
— DHH (34:16)
On Overcoming Adversity:

“I’m so happy Apple chose to be such a greedy dick about it, because otherwise...”
— DHH (69:10)
On His Work Setup:

"I'm doing this call from my Framework desktop running Amachi and my delicious mechanical low profile keyboard. And it all just worked beautifully. There is a piece of Apple in the equation...I still have an Apple 32 inch monitor."
— DHH (75:56)
On Personal Work Philosophy:

“We get to have fun. We get to chase our ideas. We get to be ludicrously ambitious in our definition of it...And it worked.”
— DHH (66:06)

Timestamps for Important Segments

| Timestamp | Segment Description | |-----------|--------------------| | 00:23 | DHH’s multifaceted career identity explained | | 02:45 | Building philosophy-driven businesses, “out-teach not outspend” | | 07:21 | Imposter syndrome & teaching before you’re “qualified” | | 09:58 | Liquid vs. crystallized intelligence; ignorance as a feature | | 15:47 | Dot-com bust, lack of resources, and the birth of Ruby on Rails | | 24:58 | DHH on being wrong about Facebook—resulting & humility | | 25:10 | Taste vs. data: ignoring conversion rates and A/B tests | | 32:36 | The “context” of wisdom and why advice isn’t universal | | 34:12 | Lessons from Shopify’s unfathomable scale—and what nobody knows | | 36:16 | Tobi Lütke’s nerdy leadership style and early AI convictions | | 41:35 | DHH’s change of heart on AI capabilities and workflow | | 48:45 | Building an audience is no longer enough—changes in social virality | | 53:16 | Mentors and blueprints: Semler, Beck, Matz | | 62:20 | Longevity, company-building, and how to stay in love with your business | | 69:34 | The "Hey.com vs. Apple" story—app store battles for independence | | 75:56 | DHH on his ideal work setup; Linux, Framework PC, Apple monitor |

The Core Threads

Independence breeds original thought and long-term business health.
Lack of investment and external control produces relentless focus and creativity.
Grinding isn't admirable—margin and ruthless selectivity matter more.
Follow your taste; only use data when it’s truly directive.
Most dogmas are context-dependent. “Nobody knows anything” is a stronger rule than most advice.
Humility—about both your wins and your mistakes—is crucial at any scale.
You can (and should) design your own game. Build a company—and life—that you actually want.

For Listeners: Why This Episode Matters

If you wrestle with imposter syndrome, struggle to find “silver bullet” business advice, or worry you aren’t grinding hard enough to build something substantial—DHH’s experience offers a liberating, sharp counter-narrative. His longevity, candor, and humility exemplify a rare type of entrepreneurial wisdom: contextually rooted, deeply principled, and always ready to challenge the mainstream.

My First Million Podcast

Episode Overview

Key Discussion Points & Insights

1. DHH’s Multifaceted Background and Philosophy

DHH on His Identity (00:14)
- DHH adapts his introduction based on audience: car enthusiasts get Le Mans stories, programmers hear about Ruby on Rails, entrepreneurs get Basecamp/37signals.
- Quote:
  
  "If I'm talking to a bunch of car nerds, I talk about winning Le Mans. If I talk to a bunch of programmers, it's all about Ruby and Rails. And if a bunch of entrepreneurs, it's usually about building Basecamp and 37signals."
  — DHH (00:23)
Philosophy Over Features (01:36)
- 37signals’ website features a 1999-style 'manifesto'—a compilation of raw, old-school chapters outlining their beliefs.
- "A lot of it is simply based in the fact that neither Jason or I can shut up about what we believe." — DHH (02:45)
- Fundamental approach: out-teach, not outspend competitors.
The Privilege of Privacy (00:39, 27:08)
- 37signals has never revealed full revenues/profits (described only as "ridiculous")—a luxury enabled by being private and profitable.

2. Teaching Before You're “Qualified”—Imposter Syndrome & Ignorance as Strength

Imposter Syndrome and Out-Teaching (07:21)
- Sam admits initial hesitation to give advice since others are more successful.
- DHH credits a “completely irreverent personality” and the drive to internalize by teaching.
Liquid vs. Crystallized Intelligence (09:58)
- Younger people have “liquid intelligence”—speed, boldness, and “productive ignorance.”
- Quote:
  
  "Ignorance is a benefit for a huge class of problems...you will be locked into paradigms and thought patterns. If you want to break those paradigms, you kind of got to start from a clean slate."
  — DHH (12:28)

3. How Constraints Sparked Creativity & Ruby on Rails

Dot-Com Bust as Crucible (12:28–16:23)
- Lack of cash forced DHH and Jason to be scrappy—using open source tools, handling everything in-house.
- Quote:
  
  "I could not use the same technology as everyone else was using, because I had a tenth, a hundredth, a thousandth of the capacity. Therefore, I had to use something else...And this in my case...was the birth of Ruby on Rails."
  — DHH (15:47)

4. Taste vs. Data—Why They Ignore A/B Tests

Taste Over Metrics (24:58–32:21)
- Despite legendary copywriting (e.g., hey.com), DHH and Jason “never really looked at conversion rates.”
- Quote:
  
  "I've never really thought about it. I just know that it felt good and I think it's good. Therefore we just ran with it."
  — Jason Fried (relayed by Sam, 25:10)
- They eventually dropped most analytics and A/B testing:
  
  "After trying that for over a decade...we never did what the numbers told us to do. We would do whatever the hell we wanted to do."
  — DHH (27:53)
The Luxury of Margins and Freedom (26:17)
- High profitability meant they could ignore the grind, focus on what energized them, and dismiss standard productivity dogma.
- "Grinding is the stupid shit you do in World of Warcraft when you're peon. No, thank you. I don't want to do that."
  — DHH (28:42)

5. Humility—Learning from Being Wrong

The Facebook $33 Billion “Miss” (18:03–24:58)
- DHH famously wrote that Facebook “wasn’t worth $33B” in 2010. In hindsight, Facebook proved him wrong—he owns it, and uses it as a lesson in humility and “resulting.”
- "You should have some humility about your predictions."
  — DHH (24:42)
- On evaluating luck vs. process:
  
  "[In poker] the way to win...is to make sure you predominantly play hands that have the best odds...if you go all in on a hand that has 87% odds...and you lose, you’re an idiot if you draw the conclusion that you shouldn’t have gone in on that hand. Totally should have."
  — DHH (20:47)

6. Context Matters—Why There’s No Universal “Wisdom”

Contextual Nature of Advice (32:36–34:12)
- DHH critiques “wise axioms” as context-bound; what works for a small startup may not for a behemoth like Shopify.
- "For every wise axiom, you can find another that says the opposite. That also sounds wise."
  — DHH (32:36)

7. Lessons from the Shopify Board

Nobody Knows Anything (34:12–36:16)
- DHH describes joining Shopify’s board as an awe-inspiring learning experience—yet, admits even board members can't truly explain massive growth.
- "Nobody knows anything...we can have all these theories. Very, very little of it gets to be reduced to irrefutable proof in the sense of a math equation."
  — DHH (35:30)
Tobi Lütke’s Unique Leadership (36:16–38:38)
- Tobi remains a “computer nerd” at heart, with deep technical curiosity and future-driven vision. His conviction often ran counter to industry consensus—sometimes being “right a lot” simply by checking facts others miss.

8. DHH’s Evolution on AI

AI Skepticism to Full Enthusiast (41:35–47:34)
- Initially fascinated but dissatisfied with AI’s code quality and annoyances, DHH’s attitude fundamentally shifted with the arrival of state-of-the-art models in late 2025.
- Quote:
  
  "The last three months...have been the most churn in my mental approach to computers...now I’m in the herd...the agents are incredibly capable programmers."
  — DHH (45:58)

9. What's Changed Since 37signals’ Early Days

Building Audiences No Longer Converts Like It Used To (48:45–51:53)
- The classic "jab, jab, jab, right hook" content model is breaking down—algorithms increasingly throttle company reach, meaning audiences don't guarantee business.
- "I'm not sure our historic long run strategy of build a large audience and then good things will happen is necessarily true anymore."
  — DHH (50:34)
Still, Teaching is Worthwhile for Personal Growth
"It's actually how you learn more...when you try to teach what you've internalized, you make it sink in deeper."
— DHH (51:28)

10. Influences, Role Models & Work-Life Philosophy

On Inspiration and Side-Quests (53:16–60:22)
- Early on, DHH’s blueprint was “find people I like and copy their motions” even without fully understanding them.
- Ricardo Semler (author of Maverick) gave permission to break industrial norms.
- Kent Beck (Extreme Programming) showed how to challenge tech orthodoxy.
- Matz (Ruby’s creator) reframed programming with “programmer happiness” as a priority.

Quote on Lasting Companies: (62:20)

> "The number one objective both Jason and I [have] is to ensure that 37signals is still a place we want to work...Not just want to work, but like to work."  
— DHH (62:20)

On Avoiding Burnout and Stress (64:31–66:14)
- Early profits and financial success gave DHH margin and detachment:
  
  “We just reached [financial stability] quite early...So now I’m in fluffy land. If this ends tomorrow, I can be at peace with the whole thing...The vast majority of anxiety that wreck entrepreneurs...are about forces outside of their control. The best you can do is the best you can do.”
  — DHH (65:10)

11. The Legendary "Hey.com vs. Apple" Story

Battling Apple Over App Store Fees (69:34–75:52)
- Apple tried to enforce a 30% revenue cut for "Hey" iOS app access—DHH and Jason refused, enduring a high-stress, public showdown. Their principle: if you're not selling via the app, Apple shouldn't get a cut.
- "I would rather burn down millions of dollars to build over two years than to pay the gangster shakedown."
  — DHH (71:27)
- Ultimately, Apple bent, re-writing the rules to fit an exemption for Hey.
Philosophy: No-Permission Tech
"If I publish a website on the Internet...I get to do it. I don't have to ask anyone for permission. There’s a little bit more permission these days, but...no permission tech, no permission platform. This is what me likes."
— DHH (73:25)

Notable Quotes & Memorable Moments

On Advice and Originality:

“Neither Jason nor I have been in Silicon Valley...which meant that original thought was possible.”
— DHH (05:25)
On the “Myth” of Data-Driven Everything:

“Maybe all the statistical analysis is a bit of hocus pocus...the missing ingredients to getting to the capital T truth is unknown.”
— DHH (31:03)
On Shopify’s “Glitch in the Matrix” Growth:

“Shopify last year grew almost 30% year over year. I would’ve been happy to grow 30% year over year...at the board, even Toby, we don’t really know [why].”
— DHH (34:16)
On Overcoming Adversity:

“I’m so happy Apple chose to be such a greedy dick about it, because otherwise...”
— DHH (69:10)
On His Work Setup:

"I'm doing this call from my Framework desktop running Amachi and my delicious mechanical low profile keyboard. And it all just worked beautifully. There is a piece of Apple in the equation...I still have an Apple 32 inch monitor."
— DHH (75:56)
On Personal Work Philosophy:

“We get to have fun. We get to chase our ideas. We get to be ludicrously ambitious in our definition of it...And it worked.”
— DHH (66:06)

Timestamps for Important Segments

The Core Threads

Independence breeds original thought and long-term business health.
Lack of investment and external control produces relentless focus and creativity.
Grinding isn't admirable—margin and ruthless selectivity matter more.
Follow your taste; only use data when it’s truly directive.
Most dogmas are context-dependent. “Nobody knows anything” is a stronger rule than most advice.
Humility—about both your wins and your mistakes—is crucial at any scale.
You can (and should) design your own game. Build a company—and life—that you actually want.

DHH: $100M+ Advice That'll Piss Off Every Business Guru

Summary

My First Million Podcast

Episode Overview

Key Discussion Points & Insights

1. DHH’s Multifaceted Background and Philosophy

2. Teaching Before You're “Qualified”—Imposter Syndrome & Ignorance as Strength

3. How Constraints Sparked Creativity & Ruby on Rails

4. Taste vs. Data—Why They Ignore A/B Tests

5. Humility—Learning from Being Wrong

6. Context Matters—Why There’s No Universal “Wisdom”

7. Lessons from the Shopify Board

8. DHH’s Evolution on AI

9. What's Changed Since 37signals’ Early Days

10. Influences, Role Models & Work-Life Philosophy

Quote on Lasting Companies: (62:20)

11. The Legendary "Hey.com vs. Apple" Story

Notable Quotes & Memorable Moments

Timestamps for Important Segments

The Core Threads

For Listeners: Why This Episode Matters

Further Reading & References

Summary

My First Million Podcast

Episode Overview

Key Discussion Points & Insights

1. DHH’s Multifaceted Background and Philosophy

2. Teaching Before You're “Qualified”—Imposter Syndrome & Ignorance as Strength

3. How Constraints Sparked Creativity & Ruby on Rails

4. Taste vs. Data—Why They Ignore A/B Tests

5. Humility—Learning from Being Wrong

6. Context Matters—Why There’s No Universal “Wisdom”

7. Lessons from the Shopify Board

8. DHH’s Evolution on AI

9. What's Changed Since 37signals’ Early Days

10. Influences, Role Models & Work-Life Philosophy

Quote on Lasting Companies: (62:20)

11. The Legendary "Hey.com vs. Apple" Story

Notable Quotes & Memorable Moments

Timestamps for Important Segments

The Core Threads

For Listeners: Why This Episode Matters

Further Reading & References