Update:

I am currently:

  • in San Francisco! Going to tech events & generally hanging out

  • headed to Buenos Aires on Sunday for some months+ extended travel.

  • unemployed! More on that below in 'Ask'

Offer:

I think more people should have their own websites.

To that end I'm offering a service (https://www.jakesimonds.com/services! Oooh!) for anyone who knows less about computers than me where over a two-hour zoom call we build you a personal website. I thought about calling it Likable (as in Lovable but not making such insane promises), but settled on Webmaster Crash Course.

If this is as good an idea as I hope it is I'm hoping to charge people $$$ for this, but since it's brand new I'll do it for free. Consider signing up. It's 2 hours slots but will do less if you want!

Ask:

I'm very frightened to be unemployed and not at all certain that I haven't made a massive, unforced error.

Not asking for your sympathy, but...

Are you thinking about starting a company? Let's chat

I am interested in:

  • how can companies with external-facing APIs or frankly any public web presence make themselves legible & friendly to the humans and humans-using-ClaudeCode/Codex that will find them?

    • Thinking less custom fine-tuning, more convert everything to markdown and then see where Claude gets stuck.

    • The slimy version of this will be SEO for LLMs. That phrase makes me throw up in my mouth a little but I do think it's an interesting space

  • protocols over platforms. To the degree that open social matures, could there be a business around helping companies migrate and own their own social stuff?

  • The 95% problem: when the LLM gets you 95% of the way to what you want, how intuitive is it for the person to jump in and finish the work? So many current LLM implementations it's confusing/impossible to take over from the LLM. Exa Websets and the cursor side-chat are two examples of doing it well.

  • I'd rather get really good at solving specific problems and be a consulting business than try to thread the needle and make something that'll scale perfectly.

Seeking Informational Interviews

Right now I am planning to return to conventional employment somewhere around March 2026.

My ideal job:

  • as synchronous as possible while still in software (zoom calls over DMs & hanging out IRL over zoom calls)

    • & not because remote-first doesn't work, it obviously does. This is more just a my-preference thing & it's a pretty strong preference for how I want to live the one life I have. I'd rather hang out than trade DMs.

  • open to travel. Open to software sales. I love conferences, I love being really close to the actual people with the problem we're solving. And I think I'm happiest/at my best when I'm able to be an advocate for something I really believe in

  • my nosey-ness and penchant for asking tons of questions is regarded as an asset.

Any of the above are negotiable. Depending on the job market in a few months maybe they'll all be negotiable.

& specifically curious in learning more about:

  • Software sales (wish I knew more about this world)

  • Developer Relations (would love to chat with someone in a role like this to ask just basic questions)

  • Start up investing space (again, I know so little about this world – seems an interesting intersection of building networks of people and staying technical)