Hello, my name is __________. ¶
Hi there 👋 my name is Caleb Hailey. I am the Co-Founder and Product lead at Herd Works.
I live in Portland, Oregon 🌲 and I have had the great fortune of getting paid to play with computers for the last 15+ years. 👨🏽💻 I owned my first computer in 2002, got my first tech job in 2006, launched my first tech product in 2011, and became the co-founder and CEO of my first tech startup in 2017, which was subsequently acquired in 2021. 🤯 Along the way I have developed what I would consider a healthy 😍 love / hate 🤬 relationship with technology. I’ve also spent the last 10+ years building or working for fully-remote companies, so besides rambling about technology I plan on mumbling about WFH and the future of work from time to time.
Interest graph ¶
Like most folks, my passive interest graph has evolved over time. If I’m successful at bootstrapping a writing habit with this blog and I make it past the obligatory “hello, world”, I suspect that my interest graph will change. To keep me honest, I’m going to document my current interests here, then if/when they change I can write about it.
- Tech / Gadgets 1
- Productivity / GTD / WFH
- Automation
- Operating systems (Linux, iPadOS, iOS, MacOS)
- Open source software
- DIY 2
- Podcasts & podcasting 3
- Music
- Local businesses & startups
- Cars
Oh, and since the world is full of bad news, I’ll try to keep it pretty positive here. That’s the inspiration for this blog anyway – a little compilation of things that make me say “sheesh!”. 😊
Inspired by… ¶
This blog was heavily inspired by internet heroes who have been doing this for a LOT longer than me. Some of these inspirations are always on my mind, and some fade from time to time. To help me remember, and to give credit where credit is due, I am maintaining an inspired by page that I will update over time. If I’m missing anyone today, I’ll add them tommorrow. If you have enjoyed reading something on sheesh.blog, I’m sure you’ll enjoy these writers and ideas as well. Check it out!
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I’m a nerd for the gadgets, but don’t worry — this isn’t going to become yet another “unboxing” or “review” site. ↩︎
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I suspect I’m going to write about what I’m currently tinkering with on my computer(s), and maybe even what’s going on in my garage. ↩︎
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A good friend and I started our first podcast in 2005, way before it was mainstream. 🤓 We had gained over 3000 subscribers on iTunes 📈 in just a few months time before we had to give it up. We were having a lot of fun with it, but it was taking up too much time and we didn’t have a clear idea of how to turn it into something that could pay a decent salary. I’m definitely no expert, but if I can make this writing habit stick, I have a few ideas about how I might also start podcasting again. 🤞 ↩︎