The Curious Engineer

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Justin Jackson

justinjackson.ca

Co-founder of Transistor.fm (podcast hosting). I write about SaaS marketing, bootstrapping startups, the good life, calm companies, and creating a better society.

Essays / personalAI / MLEngineering management / careers

’05’10’15’20’25
Posts
381 from 25 Mar 2003 to 11 Oct 2026
Posting
monthly (13 in the last year)
Kind
personal blog
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https://justinjackson.ca/feed

2026 13

  1. You have to really enjoy what you're working on
  2. Do you want it the most?
  3. The value of software in a Fable world
  4. Thoughts from the 2026 London Podcast Show
  5. We have a communication problem
  6. Do the hardest thing
  7. Necessary but not sufficient
  8. What has technology done to us?
  9. Three struggles with AI coding agents
  10. Will Claude Code ruin our team?
  11. Don't kill my pretty RSS feed
  12. Claude Code and the new age of software development
  13. 2025 year in review

2025 17

  1. Entrepreneurship advice for high school students (what I wish I knew)
  2. What kills motivation?
  3. Time machine
  4. Effort vs Outcomes
  5. A good find
  6. Reasonably unreasonable
  7. (Draft) The Podcast Generation Cliff
  8. No, AI Won't Turn Everyone Into App Developers
  9. Changed my mind: AI is actually good for coding
  10. Thoughts going into the London Podcast Show
  11. Will YouTube kill the podcast industry?
  12. Finding your "zone of genius"
  13. What the podcast industry gets wrong about YouTube
  14. AI isn't going to build your startup
  15. How to make big decisions
  16. AI isn't going to replace you
  17. Is it too hard to build a SaaS in 2025?

2024 18

  1. 2024 year in review
  2. What's happening with founders over 40
  3. Where are these signups coming from?
  4. The best Bluesky apps, projects, tools I've found
  5. Leaving Twitter
  6. The pipeline problem
  7. It's not just B2C vs B2B anymore
  8. Investment loops in SaaS onboarding
  9. Pro skater Chad Muska went broke. Now he's a bootstrapper.
  10. How to make a podcast (and submit it to Spotify and Apple Podcasts) in 2024
  11. Track revenue, not traffic
  12. Compounding returns
  13. We need more calm companies
  14. Test articles
  15. Write 100 emails to people you know
  16. Send your users this welcome email
  17. My theme for 2024: SaaS marketing experiments
  18. 2023 year in review

2023 10

  1. Ten SaaS marketing principles for 2024
  2. Advice for Sending Cold Emails and DMs
  3. Ideas that create opportunities
  4. Flipping tables and hiring kids
  5. How I would build a new startup if I had to do it all over
  6. Silverwood Theme Park Review, Travel Tips, and Photos
  7. What happened to Paul Jarvis?
  8. Can you bootstrap a business if you have young kids?
  9. What is Bluesky social? (Twitter and Mastodon alternative)
  10. Is ChatGPT the next big startup platform?

2022 25

  1. Best affiliate programs for indie makers
  2. Public healthcare encourages entrepreneurship
  3. How to get people to choose your product
  4. Avoid fame
  5. is twitter done?
  6. How to use Mastodon: a beginner's guide
  7. Pessimism vs Optimism
  8. How to plan a remote team retreat
  9. The potential dark side of AI and GPT-3 writing tools
  10. The ethics of AI-driven feeds
  11. AI-driven content is a nightmare
  12. 2022 year in review
  13. Older founders do this better
  14. What's wrong with Elon?
  15. Why are you doing this?
  16. Same effort, but better results
  17. musk twitter quitter, bitter?
  18. Do entrepreneurs create demand?
  19. Find a good party
  20. I can't work from home
  21. The good life
  22. The Prosumer market is underrated
  23. What makes you click on a YouTube video?
  24. It's been too long
  25. Working harder doesn't make you more successful

2021 16

  1. 2021 year in review
  2. The vague headline
  3. The limits of conventional wisdom
  4. Why didn't my project take off?
  5. It might never go away
  6. The secret is to sell what people are already searching for
  7. Do you need marketing tracking and automation?
  8. Expanding my horizons
  9. Should my SaaS try to get enterprise customers?
  10. Meeps
  11. Entrepreneurial false-positives
  12. The Hierarchy of Needs for new Product Ideas
  13. How to build a simple HTML landing page using Tailwind CSS
  14. Podcasts and Capital
  15. Calm yourself
  16. How many units can you sell?

2020 17

  1. 2020 year in review
  2. The multiplier
  3. Why you should go after a market with strong demand
  4. Good idea or bad idea?
  5. Forget about your heroes
  6. Black lives matter
  7. Ideas aren't cheap
  8. The cure
  9. Main Street fights back
  10. We've been exposed
  11. Fight Amazon
  12. Maintenance
  13. How do I find customers for my SaaS?
  14. Business is like surfing
  15. The main thing
  16. Good businesses have margin
  17. 2019 year in review

2019 23

  1. Moving on
  2. Who wants this today?
  3. How do you sleep at night?
  4. The haters
  5. We sell saddles here
  6. Is the Product-Market Fit survey accurate?
  7. Selling stuff on a busy beach
  8. People want the basics done well
  9. Jason Fried wants to delete my backlog
  10. Why growing old in tech is hard
  11. How I'm learning to program
  12. Fish where the fish are
  13. The myth of the niche market
  14. When should you quit?
  15. It's gradual, then sudden
  16. How do I build something people want?
  17. Wait and see
  18. Should we always charge more?
  19. How to run a mastermind group
  20. People on the internet can be so mean
  21. Passion needs rigor
  22. Cynicism kills progress
  23. Non-alcoholic drink choices

2018 26

  1. 2018 year in review
  2. This is hard
  3. Can you bootstrap a startup on the side?
  4. My secret phone call with Hamish
  5. How I make my money
  6. Being a solopreneur has risks
  7. Let's talk about startup costs
  8. Why geeks should speak
  9. I have a new website
  10. Do you even want to be "a bootstrapper?"
  11. Two things that kill bootstrapped companies
  12. The hidden cost of bootstrapping
  13. Is this a good idea?
  14. Why many products struggle, and only a few succeed
  15. How many trials should I be getting for my SaaS?
  16. 30k
  17. Elon Musk and free speech
  18. Bootstrapper's paradox
  19. Your business isn't about finding a great idea
  20. Maybe you shouldn't be a solopreneur
  21. Optimize for usage, not just sales
  22. Don't sell to beginners
  23. What would you do differently?
  24. Why I'm building a new SaaS in 2018
  25. What affects customer motivation?
  26. What raves and software have in common

2017 15

  1. Finish the year strong
  2. 2017 year in review
  3. How to build a Shopify app – Björn’s journey to $300k in profits
  4. What's on your hard drive?
  5. How an NBA player ruined my life
  6. I've never done this before
  7. Stop by for coffee
  8. Why I bought your software
  9. What is Jobs to be Done? (JTBD)
  10. "People need my product!" (But do they want it?)
  11. How to create a membership website
  12. Don't stand still
  13. Things to do when Amazon S3 is down
  14. Why most product ideas aren't that good
  15. Watch for mind gremlins

2016 4

  1. When you're building a product, whose opinion should you listen to?
  2. The Freedom Ladder
  3. You don't learn until you ship
  4. Adam Wathan's $100k product launch

2015 3

  1. More stuff or better stuff?
  2. Building software for podcasters –\_Josh Nielsen from Zencastr
  3. Why you need a co-founder

2014 2

  1. The hidden reasons why people are using your software
  2. Not all products make good businesses

2013 4

  1. Out of office
  2. The 80% energy principle
  3. I've been following you since grade 9
  4. How to be more social at events and conferences

2012 2

  1. You only win once
  2. Why people buy software

2011 1

  1. Change your market, save your product

2010 1

  1. Can you change customer behavior?

2003 1

  1. Unconventional bootstrapping: round 1

Undated 183

  1. Going independent (2016 year in review)
  2. The tools I use
  3. How to surprise people in a digital age
  4. This is what starting small looks like
  5. How to get out of a rut
  6. We all want progress
  7. Virtual reality could save the planet
  8. Hypothesis: Nintendo Switch is a social play
  9. I wasted 4 years of my life doing this
  10. Who are you stealing from?
  11. Using JTBD to build better products
  12. Pricing experiment results
  13. What podcasters get wrong about advertising
  14. How to make money from your tiny podcast
  15. You can't change the customer's behavior
  16. SaaS is ripe for disruption
  17. My workplace fantasies
  18. Publish your ebook as PDF, MOBI, and ePub all at the same time
  19. Why I sell before I launch
  20. How I price products
  21. You want more than product/market fit
  22. Why we buy from winners
  23. Your secret success fantasy
  24. Put a billion dollars on red
  25. Focus on your own shit
  26. Park your experience
  27. Don't swim upstream
  28. Is the market for self-published books saturated?
  29. Business is like a game of Frogger
  30. Fear of launch
  31. You can't split test human experience
  32. Product traction is like waiting in line at the grocery store
  33. Make stuff and be happy (2015 year in review)
  34. Documentaries you should watch this holiday
  35. How to build demand before you launch
  36. You're lucky
  37. 3 things I learned from my book launch
  38. The last mile
  39. Startups should make money
  40. Keep making things
  41. Ultimate validation
  42. End of an era
  43. Do people still read blogs?
  44. No marketing unicorns
  45. Don't follow your heroes
  46. 2014: a year of making stuff
  47. Landing page teardown: Serial podcast
  48. How user growth really works
  49. Do I look dumb?
  50. Do things that scare you
  51. Be careful who you go to for advice
  52. The cold months are coming
  53. Let’s make some stuff
  54. What type of pain are you solving?
  55. The person on the other side of the screen
  56. Earn the right to be heard
  57. Your product's missing ingredient
  58. Is it harder to get noticed?
  59. It's different now
  60. When you can't win
  61. Your second biggest problem
  62. How desperation affects creativity
  63. Be social IRL
  64. Choose your audience wisely
  65. Your blog could be a party
  66. My embarrassing iTunes receipt – exploring the customer journey
  67. Start your marketing with other people in mind
  68. Speaking of starting small
  69. How to start
  70. Get traffic for your content
  71. A simple way to validate your startup idea
  72. Play the long game
  73. Is "sales" a dirty word?
  74. We are not normal people
  75. Feeling threatened
  76. This is real life
  77. How do you find time for side projects when you have kids?
  78. The 2013 revenue stats I didn't want to share
  79. It's not us, it's them
  80. Succeed with your own product in 2014
  81. Why didn't you launch last year?
  82. How to choose an audience for your blog
  83. 1,000 email subscribers
  84. What stops us from building products?
  85. How remote work changed my life
  86. The downward spiral
  87. Where does a great culture come from?
  88. My first kiss
  89. Nikki Durkin: Don't talk about ideas - just do it
  90. Why you're not making sales
  91. How to get (and keep) a job in startups
  92. Geeks as tastemakers
  93. Producing good content isn't enough
  94. Self-Publishing Hangout highlights
  95. Just f*cking do it
  96. Hiring developers
  97. Why people buy products
  98. Sitting on the curb drinking a slurpee
  99. Believe in me
  100. Heads down
  101. Quit trying to attract a crowd and just help people
  102. Pretty doesn't sell
  103. Twenty dollars in an envelope
  104. How to end the remote work debate
  105. How (not) to validate your idea
  106. Don't call it a comeback (working remotely)
  107. Meet people
  108. Starting a business is easy
  109. My blogging demons
  110. Jarrod Drysdale's advice for starting
  111. A VIKA BYSKE standing desk
  112. It's not enough to build a product that people want
  113. Why distributed teams are more effective
  114. Why I would pay for Twitter
  115. What the People of Wal-Mart want
  116. Why I don't read at work
  117. What Amy Hoy taught me about starting a business
  118. A 13-year-old on a BBS
  119. Retina is not a big deal
  120. Terrible Apple products
  121. Geek dad
  122. No one wants to buy my sneakers
  123. Forget the Valley: bootstrap founders can live wherever they want
  124. Most successful founders are in their mid-30's, married with children
  125. Kathy Sierra is brilliant
  126. Customers don't care about your solutions
  127. Things I've quit doing at my desk
  128. Will a college degree get you a programming job?
  129. If you work with pixels you should be thankful
  130. What's important
  131. How to keep clients happy
  132. Building a better mousetrap? It had better catch more mice.
  133. Fatherhood
  134. What is real work?
  135. How to get 1000's of paying customers
  136. How do you know when to stop designing?
  137. Where would you rather work: 37signals or Zappos?
  138. Useful is forever
  139. Zappos is wow
  140. How do you consume digital media?
  141. Your idea needs a passionate believer
  142. How to build a better Canadian neighborhood
  143. Are you in love with the idea, or with customers?
  144. Meshwest Edmonton
  145. How to design a customer support process
  146. 8 habits for a better day at work
  147. My rant on customer support for web apps
  148. Stop screen sucking
  149. Everybody stop
  150. No one knows what they're doing
  151. The coupon code is a slap in the face
  152. I worked a day at 37signals, and I liked it
  153. If you're from Edmonton, you'll remember Happy Pop soda
  154. The sex and cash theory
  155. Building a standing desk
  156. Why are people looking at your website?
  157. We're in the Age of Content
  158. This is a classy move
  159. Be real.
  160. B2b
  161. Business lesson: less research, launch small
  162. Review of 37signals' first app for the iPad: Draft
  163. The iPad is a family device
  164. 2010: Products I can't live without
  165. Better time spent at work
  166. Interviews from the Future of Web Apps in Miami
  167. A better office
  168. Better typing
  169. A better Apple TV
  170. A better birthday party for kids
  171. Better doctor visits: house calls
  172. A better urbanism
  173. Local news web site
  174. Think clearly about print advertising
  175. A better toilet
  176. A better parking lot
  177. Why can't we stream TV in Canada?
  178. Yes! Apple TV!
  179. Good news for fans of the IT Crowd
  180. Justin's world
  181. bootstrapping startups
  182. This is a webpage
  183. I’m a f*cking webmaster