Justin Jackson
Canadian bootstrapper and writer on small software businesses. Co-founder of the podcast hosting company Transistor.fm and author of the book Marketing for Developers.
Everything they publish, on ppll ↗
Justin Jackson did not write this page.
We collected these quotes from things they published elsewhere, and every quote links to where it was said. They have no account here and have not endorsed this site. Quotes are word for word; the short line under each one is our own restatement, not their wording. Their own site. Is this you? Claim it or ask us to remove it. Or tell us what is wrong here.
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Our reading
Scarcity and difficulty of production, not just usefulness, are what let a seller charge more.
Their wordsGenerally, the economy rewards difficulty and rarity. If something is hard to do or make, you get to charge more.
↗The value of software in a Fable worldjustinjackson.ca 1st of 3 in this piece
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Their wordsMy guess is that people will still want to buy certain types of software and tools "off-the-shelf."
↗The value of software in a Fable worldjustinjackson.ca 2nd of 3 in this piece
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Their wordsIndie entrepreneurs need to stack every advantage they have, and increasingly "coding" won't be the advantage it once was.
↗The value of software in a Fable worldjustinjackson.ca 3rd of 3 in this piece
- 2 weeks earlier
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Their wordsI don't think mass-produced AI-generated shows are a big threat to podcasting, mostly because I don't think consumers like them.
↗Thoughts from the 2026 London Podcast Showjustinjackson.ca 1st of 2 in this piece
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Our reading
LLMs replacing podcasts as a source of information poses a real disruption to podcasting.
Their wordsWhere I do see some disruption is where consumers start asking ChatGPT and other LLMs for information they would normally get from podcasts.
↗Thoughts from the 2026 London Podcast Showjustinjackson.ca 2nd of 2 in this piece
- 11 days earlier
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Our reading
Many of society's problems stem from how people communicate online, not just what they discuss.
Their wordsI'm convinced that many of society's problems come from how we communicate online.
↗We have a communication problemjustinjackson.ca 1st of 2 in this piece
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Our reading
Face-to-face interaction conveys understanding and empathy that text-based communication does not.
Their wordsIn person, it's easier to grok where someone's coming from. It's simpler to see how they're feeling.
↗We have a communication problemjustinjackson.ca 2nd of 2 in this piece
- 10 days earlier
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Their wordsYour hardest idea is often your best idea, the one with the most potential.
↗Do the hardest thingjustinjackson.ca 1st of 3 in this piece
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Our reading
The most valuable problem to pursue is the hardest one someone is genuinely positioned to solve.
Their wordsDoing "the hard thing" means pursuing the highest-value problem you can find that still sits inside your zone of expertise; the hardest problem you're personally in a position to win.
↗Do the hardest thingjustinjackson.ca 2nd of 3 in this piece
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Their wordsChoosing to tackle "the hardest feature" generally produces power-law-level returns, as opposed to tackling something less hard.
↗Do the hardest thingjustinjackson.ca 3rd of 3 in this piece
- 2 days earlier
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Their wordsMost business advice is necessary but not sufficient on its own to achieve success.
↗Necessary but not sufficientjustinjackson.ca 1st of 3 in this piece
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Their wordsYou can build "the hard thing" in a good market, with every advantage, and still lose if what you ship doesn't give people enough reason to leave what they're already using.
↗Necessary but not sufficientjustinjackson.ca 2nd of 3 in this piece
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Their wordsIf you're bootstrapping, you should probably have another source of revenue to sustain you.
↗Necessary but not sufficientjustinjackson.ca 3rd of 3 in this piece
- 6 weeks earlier
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Their wordsThere will be negative second-order effects of almost every widely distributed technology.
- 5 weeks earlier
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Their wordsLLMs make it easy for anyone to add new features to the product. Even before AI, teams were battling feature creep, where the product becomes increasingly complex, bloated, and cluttered.
- 10 days earlier
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Our reading
AI-driven skill compression will be disruptive to software team culture in the short term.
Their wordsIn the short term, this is going to be incredibly disruptive for team culture.
↗Will Claude Code ruin our team?justinjackson.ca 1st of 3 in this piece
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Their wordsWhen rare skills become more attainable, people feel pressure to move "up the stack" to prove their value.
↗Will Claude Code ruin our team?justinjackson.ca 2nd of 3 in this piece
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Their wordsAs more people build software and cycle time compresses, they'll start to absorb lessons that it took their colleagues decades to learn.
↗Will Claude Code ruin our team?justinjackson.ca 3rd of 3 in this piece