Founders Podcast #276: Paul Graham’s Essays, Part 2

Host: David Senra
Date: November 9, 2022
Featured Essays: “How to Think for Yourself,” “How to Work Hard,” “How to Lose Time and Money,” “Schlep Blindness,” and “What I’ve Learned from Users” by Paul Graham

Overview

In this episode, David Senra continues his exploration of Paul Graham's seminal essays, focusing on themes deeply relevant to entrepreneurs: independent thinking, work ethic, failure, identifying valuable problems, and firsthand lessons from guiding startups at Y Combinator. Senra brings Graham's words to life by integrating personal reflections, historical examples, and interjections of entrepreneurial wisdom from other figures. The episode is structured as a rich, flowing commentary on the essays, offering both actionable insights and philosophical provocations for founders.

Key Discussion Points & Insights

1. Independent-Mindedness & Non-Conformity

(Essay: "How to Think for Yourself")
[00:00-07:30]

• The Necessity of Nonconformity for Entrepreneurs:
  “Your ideas have to be both correct and novel…You have to do something that sounds to most other people like a bad idea, but that you know isn’t.” (A quoting Paul Graham, [00:25])

  • Examples: Microsoft and Airbnb started as ideas most considered foolish.

• Nature vs. Nurture:
  “Independent-mindedness seems to be more a matter of nature than nurture...if you pick the wrong type of work, you’re going to be unhappy.” (A, [01:15])

• Mistaken Self-Assessment:
  Many believe they’re independent-minded when they actually conform to peer beliefs.

• Curiosity as Compass:
  “How much does the work you’re currently doing engage your curiosity? If the answer is not much, maybe you should change something.” (A quoting Paul, [04:48])

  • “Do what you’re curious about” may outperform “do what you love.”

• Building Your Own Circle:
  Founders often relate better to other founders than their employees, reinforcing the need for “peers in independence.”

2. The Dynamics of Working Hard

(Essay: "How to Work Hard")
[08:00-32:30]

• Hard Work vs. Smart Work:
  Talent alone is not enough—hard work is universally required at the highest levels.

  • “You do both. They all do both. They work hard and smart.” (David Senra [09:30])
  • Example: Bill Gates worked every day in his 20s; Wodehouse rewrote every sentence 10–20 times.

• Three Ingredients for Great Work:
  “Natural ability, practice, and effort. You can do pretty well with just two, but to do the best work, you need all three.” (A quoting Paul, [12:20])

• Motivation by Fear & Internal Drive:
  Paul Graham and others describe an “alarm bell” when not achieving or progressing.

  • “When I’m not working hard, alarm bells go off. I can’t be sure I’m getting anywhere when I’m working hard, but I can be sure I’m getting nowhere when I’m not.” (Paul, quoted by David, [14:20]

• Limits of Productive Hours:
  Different work requires different limits—programming, writing, or startup-running each carry their own sustainable intensities.

  • “My limit for the harder types of writing or programming is about five hours a day, whereas when I was running a startup, I could work all the time.” (Paul, quoted by David, [18:30])

• Aim for the Core, Not the Edges:
  “Many problems have a hard core at the center surrounded by easier stuff at the edges. Working hard means aiming towards the center to the extent that you can.” (Paul, [22:52])

• When to Switch Fields/Projects:
  Self-honesty is key—are your efforts yielding results? If not, reorient or shift.

  • “If you’re working hard but not getting good enough results, you should switch. Simple to say—hard to do.” (Paul, paraphrased by David, [26:45])

• Interest Outweighs Discipline:
  “A deep interest in a topic makes people work harder than any amount of discipline can.” (Paul, [29:15])

  • The interplay of intrinsic curiosity and external effort is paramount.

• The System Can’t Be “Tricked”:
  “Working hard is not just a dial you turn up to 11. It’s a complicated, dynamic system … If you’re consistently honest and clear-sighted, it will automatically assume an optimal shape and you’ll be productive in a way few people are.” (Paul, [31:30])

3. Avoiding Losses: Time and Money

(Essay: "How to Lose Time and Money")
[32:45-38:15]

• Most Fortunes Lost via Bad Investments, Not Spending:
  “If you’d asked me as a kid how rich people became poor, I’d have said by spending all their money. But in fact, the way most fortunes are lost is not through excessive expenditure, but through bad investments.” (Paul, [33:15])

• Investing Bypasses Internal “Alarm Bells”:
  Mistakenly viewing transfers of money as “investments” (rather than expenditures), people skip over their instinctual caution.

• Dangerous Ways We Lose Time:
  Time is most often wasted on “fake work” rather than overtly pleasurable activities; the latter makes one feel guilty, but busywork masquerades as productivity.

  • “The most dangerous way to lose time is to not spend it having fun, but to spend it doing fake work.” (Paul, [36:10])

4. Overcoming Schlep Blindness

(Essay: "Schlep Blindness")
[38:20-43:30]

• Schlep = Tedious/Unpleasant Task:
  Many of the best startup opportunities are ignored because they look like miserable, labor-intensive problems (“schleps”) to solve.

  • “A company is defined by the schleps it will undertake.” (Paul, [39:00])

• Stripe as the Archetype:
  Nobody wanted to fix payment processing online (“schlep blindness”)—so Stripe founders did it and built a massive company.

  • “Why work on problems few care about … when you could fix one of the most important components of the world’s infrastructure? Because schlep blindness prevented people from even considering the idea of fixing payments.” (Paul reading, [40:45])

• Value in Hard, Overlooked Problems:
  Such hard problems act like undervalued stocks, because they repel most entrepreneurs.

• Advice: “Take Yourself Out of the Picture”
  “Instead of asking, ‘What problem should I solve?’ ask, ‘What problem do I wish someone else would solve for me?’” (Paul, [43:00])

5. What Paul Graham Learned from Y Combinator’s Users

(Essay: "What I’ve Learned from Users")
[43:40-54:00]

• Startups Share the Same Core Problems:
  Despite varied domains, the same core issues recur repeatedly among young companies.

  • “Once you’ve advised a hundred startups, all doing different things, you rarely encounter problems you haven’t seen before.” (Paul, [44:10])

• Common Founders' Blind Spots:
  Founders often obsess over the wrong problems or misjudge the severity of issues.

  • “Founders will come in to talk about three problems… One will kill the company if it isn’t addressed immediately.” (Paul, [45:40])

• Counterintuitive Nature of Startups:
  Much of entrepreneurship runs against common sense, making good advice sound “wrong” until experience proves it right.

  • “The reason startups are so counterintuitive is that they’re so different from most people’s other experiences. No one knows what it’s like except those who have done it.” (Paul, [47:05])

• Why Founders Sometimes Ignore Advice:
  “At first I thought it was mere stubbornness… But so much about startups is counterintuitive. When you tell someone something counterintuitive, what it sounds to them is wrong.” (Paul, [48:15])

• The Importance of Focus & Speed:
  Y Combinator’s core value-add is helping founders rapidly refocus on what matters.

  • “Speed defines startups. Focus enables speed. YC improves focus.” (Paul, [50:15])
  • David relates this to Jeff Bezos’ “shoot, shoot, shoot, shoot, then aim” approach.

• The Magic of Peer Clusters:
  Great work often clusters around a “critical mass” of ambitious people (as at YC).

  • “Very ambitious people probably need colleagues more than anyone else because they’re so starved for them in everyday life.” (Paul, [52:20])

• Founders Helping Founders:
  “That’s the happiest thing I’ve learned about startup founders—how generous they can be in helping one another.” (Paul, [53:40])

Notable Quotes & Memorable Moments

• On Novelty:

  “You have to do something that sounds to most other people like a bad idea, but that you know isn’t.”
  — Paul Graham (read by David, [00:25])

• On Curiosity:

  “Perhaps if your goal is to discover novel ideas, your motto should not be ‘do what you love’ so much as ‘do what you’re curious about.’”
  — Paul Graham (read by David, [04:55])

• On Practice:

  “With each new book of mine, I have the feeling that this time I’ve picked a lemon in the garden of literature. A good thing, really, I suppose. It keeps one up on one’s toes and makes one rewrite every sentence 10 times, or in many cases 20 times.”
  — P.G. Wodehouse (read by David, [12:48])

• On Interest over Discipline:

  “A deep interest in a topic makes people work harder than any amount of discipline can.”
  — Paul Graham (read by David, [29:15])

• On Fake Work:

  “The most dangerous way to lose time is to not spend it having fun, but to spend it doing fake work.”
  — Paul Graham (read by David, [36:10])

• On Founders’ Blind Spots:

  “It’s like watching one of those horror movies where the heroine is deeply upset that her boyfriend cheated on her and only mildly curious about the door that’s mysteriously ajar... You want to say, never mind about your boyfriend—think about the door.”
  — Paul Graham (read by David, [45:50])

• On Peer Clusters:

  “Very ambitious people probably need colleagues more than anyone else because they’re so starved for them in everyday life.”
  — Paul Graham (read by David, [52:20])

Timestamps of Important Segments

• [00:00] Independent-mindedness, non-conformity, and why founders must think differently
• [07:30] The power of curiosity, finding your own peer network
• [10:00] Essay shift: “How to Work Hard”; despairing over “work smart not hard”—the need for both
• [12:20] Three necessary ingredients: talent, practice, effort
• [14:20] Inner alarm bells—“gift and curse” of high drive
• [18:30] Establishing your own daily work limits
• [22:52] Targeting the hard core of problems vs. nibbling at the edges
• [26:45] When (and how) to change direction in your work
• [29:15] Interest outpaces discipline in generating effort
• [31:30] Productivity is a system, not a dial
• [32:45] “How to Lose Time and Money”—why most fortunes and time are lost via fake investments/fake work
• [36:10] The subtle traps of busywork
• [38:20] “Schlep Blindness”—Stripe & the prize in solving “tedious, unpleasant” problems
• [43:40] Lessons from advising YC startups—shared problems, blind spots, and the value of focus
• [47:05] Why startup wisdom is counterintuitive and often ignored
• [50:15] “Speed defines startups. Focus enables speed. YC improves focus.”
• [52:20] The magic of ambitious people clustering together
• [53:40] Final reflections on founder generosity and the unique ecosystem of YC

Tone & Language

Senra delivers the episode with the enthusiasm and intensity familiar to Founders podcast listeners, mixing reverence for Graham’s clarity with a practical “learn and apply” attitude. Frequent asides draw on biographies, classic business wisdom, and personal experience, always returning to Graham’s core lessons with conviction and the language of entrepreneurial trial and discovery.

Summary Takeaway

This episode is a concentrated masterclass in entrepreneurial psychology and decision-making, filtered through Paul Graham’s essays and David Senra’s relentless drive for actionable insight. Listeners are encouraged to:

• Seek nonconformity and curiosity
• Harness hard work as a dynamic, nuanced practice
• Guard their time and money from “fake” investments and busywork
• Look for overlooked, schlep-laden opportunities
• Cultivate a peer group of like-minded strivers
• Take advice seriously—especially when it feels counterintuitive
• Always direct energy at the core of difficult problems

Essential Listening or Reading for anyone building, or hoping to build, something new.

For essay links and further episode references, visit Paul Graham’s archive at paulgraham.com.