Justin Jackson
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justinjackson.ca
Justin Jackson
@justinjackson.ca
Internet stuntman 🤸‍♂️ justinjackson.ca

⚡ Bootstrapping, SaaS, podcasting, calm companies

🎙️ Co-founder of Transistor.fm (podcast hosting).
Pinned
Just a little peek into my life
Wynford Hall NSI-1103 - Sanyo Electric Co. Ltd.

Swiveling clock radio

Early 1970s
September 9, 2026 at 4:43 AM
In its own way, every successful business is an outlier.

Your goal shouldn't be to start an average business (most businesses are not that good).

Your goal should be to build a business that bucks the trend.
September 8, 2026 at 3:12 PM
Illustration from A+ Magazine, November 1984

archive.org/details/a-pl...
September 7, 2026 at 9:06 PM
If you run a software business, you should buy @asmartbear.com’s book for the “Find your Carol” chapter alone.
September 6, 2026 at 4:28 PM
“If you enter every moment of your life at full speed, you’re gonna miss out on some points.

Pinball is the same.”

Fantastic essay by @monteiro.bsky.social

buttondown.com/monteiro/arc...
How to play pinball
What is the best arcade game? Pinball or video, or both.
buttondown.com
September 5, 2026 at 9:49 PM
🎯 100%
Tech support is where people complain about what's not working, that’s true.

But also it’s the product insights -- what’s working, what’s not, what people assume, what they wish, what they love, what they’re missing.

Are you listening, or just throwing that information away?
Tech Support is sales
Tech support isn’t just troubleshooting; it’s the face of your company. Which means it’s your brand, your positioning, and when it’s excellent, it is sales.
longform.asmartbear.com
September 5, 2026 at 9:33 PM
Reposted by Justin Jackson
Come join us for THE PANEL, live today at 11am Pacific.

www.youtube.com/live/nXMKYKS...

Out-of-the-box marketing
Hiring for customer success
Buy a business?
How to talk to customers
Marketing funnels that work
Company of one operations

@jordangal.bsky.social @briancasel.com @justinjackson.ca
THE PANEL LIVESTREAM - Brian Casel, Jordan Gal, Justin Jackson
YouTube video by The Panel Podcast
www.youtube.com
September 4, 2026 at 4:41 PM
Reposted by Justin Jackson
I’d like to propose a political test called “can you imagine this guy standing behind you in line?” where you choose a guy and if you can’t imagine them standing behind you in line they’re banished to an island for criminals
September 3, 2026 at 5:44 AM
Too many people overthink a problem before they've even tried doing it once.

Spend less time thinking and just do the thing! That's where all the learning actually happens.

After you've done it once, you can reflect on what's working and what's not working.
August 31, 2026 at 8:27 PM
Reposted by Justin Jackson
More importantly, we need to take data sovereignty more seriously. Why is DSC using Google Maps in the first place? There are cheaper and better options. How do we not have robust and scalable Canadian mapping solutions? (And yes, data sovereignty requires more data centres in Canada.)
August 31, 2026 at 1:34 AM
Kids these days say they can recognize AI images but I dunno ‘cause this 1984 editorial image from A+ magazine feels like weird AI art to me.

archive.org/details/a-pl...
August 30, 2026 at 4:34 AM
Dell Dimension XPS P 133 from 1995.

$2,699!!!
August 29, 2026 at 6:27 PM
"No matter how much [we try] to pretend otherwise, we all have flaws that we really ought to work on. We live in an unfair and opportunity-rich world where talent, privilege and effort make all the difference, cutting through the facade of blanket “perfection”"

www.readtangle.com/bring-back-s...
Have we no shame?
Against normalization culture.
www.readtangle.com
August 28, 2026 at 10:11 PM
Just published this thought: "Don't over-engineer it; just hit the ball (Golf analogy)"

Curious what you think...
Don't over-engineer it; just hit the ball (Golf analogy)
There's a great quote from a 2020 Hacker News thread: Sales is a lot...
share.transistor.fm
August 28, 2026 at 5:55 PM
Come hang out in the chat!
August 28, 2026 at 3:52 PM
Golden hour
August 28, 2026 at 6:00 AM
Reposted by Justin Jackson
I just had an excellent support interaction over chat at transistor.fm.

Which made me realize how rare that is nowadays.

Kudos to them.

/cc @justinjackson.ca
August 25, 2026 at 4:07 AM
The good ‘ol tape drive.

(Sharp MZ-2500, 1985)
August 21, 2026 at 2:20 PM
Reposted by Justin Jackson
We're livestreaming TODAY (Thursday) at 1pm Pacific (4pm EST).

Join
@jordangal.bsky.social @briancasel.com @justinjackson.ca

Topics:
- xAI's land grab
- Claude and I broke up.
- How can we be more ambitious now?

youtube.com/live/sIt2NmT...
THE PANEL LIVESTREAM - Brian Casel, Jordan Gal, Justin Jackson
YouTube video by The Panel Podcast
youtube.com
August 20, 2026 at 7:01 PM
Reposted by Justin Jackson
As tech people, when designing features, we tend to get overly clever. But then when you talk to normal people using the software, the things they actually care about tend to be way more basic than you'd ever expect. Keep it simple.
August 20, 2026 at 2:10 PM
Just published this thought: "Well, that was easy!"

Curious what you think...
Well, that was easy!
Last episode I recorded a voice memo on my walk home, dropped the file...
share.transistor.fm
August 20, 2026 at 3:47 AM
Just published this thought: "This should be easier"

Curious what you think...
This should be easier
Recorded into Voice Memos on a walk home, plane and truck noise...
share.transistor.fm
August 20, 2026 at 2:30 AM
I asked Claude to analyze @thepanel.bsky.social (using the @transistor.fm MCP server), and it basically told me the show's been more popular since @jordangal.bsky.social joined the show. 🤣
August 19, 2026 at 9:36 PM
Just published this thought: "An Update on Justin and Wildfires"

Curious what you think...
An Update on Justin and Wildfires
A lot of people have been messaging me after seeing wildfire footage on...
share.transistor.fm
August 18, 2026 at 10:35 PM
Back in 2000, while still in college, I read this article about the founders of Great Harvest Bread Co.

Their philosophy on life changed how I thought about building a business:
justinjackson.ca/the-good-life
The good life (and how to get it)
How do you build a business that gives you a good life? Make decisions with freedom and simplicity in mind, and it becomes inevitable.
justinjackson.ca
August 15, 2026 at 7:53 PM