Cassidy Williams

Software Engineer in Chicago

Cassidy's face

Being funemployed, and all that jazz

In case you missed my LinkedIn post or tweet about it, my team is open sourcing Brainstory, eventually shutting it down, and we’re separating as a team.

It’s been bittersweet, but enough time has passed now that I feel less sad about it and more reflective, and looking forward more!

Reflecting on Contenda

I learned a ton in my time at Contenda. It was quite the journey and one of the biggest learning experiences of my career. Our team was (and is!) awesome. They’re scrappy, and everyone was willing to put in a lot of work to come up with good, thoughtful products. Plus we came up with really excellent memes, which was really the backbone of the company.

We went through several pivots, as young startups do, and with each one we really worked together to see what we could salvage, and what we should throw away. This last iteration, Brainstory, was probably my favorite. If you don’t know what it is/was, it’s an app where you speak out loud with a digital coach, and it uses socratic questioning to force you to speak more and get your ideas out. Unlike ChatGPT and other LLM chatbots, it doesn’t give answers, it just keeps pushing you. Anyway, it was going well enough that Contenda started rebranding, and we leaned into it as our flagship product.

Honestly, it was going well, but after a while, we realized that we had a really nice hammer, but we didn’t know what nail we wanted to hit. We were making money, but not enough to sustain an 8-person business. We kept trying different angles and avenues and target audiences, but we just couldn’t hit that inflection point for the “hockey stick growth” you need as a VC-backed business. I started spearheading some acquisition efforts, and so many of them went just well enough that they felt good, but never well enough that we were able to save everyone’s jobs.

Slowly but surely… we were burning out. The team was getting smaller. We took salary cuts. We realized that we might have to do yet another pivot, fully from scratch, and that kind of “pre-seed” level work is incredibly intense. I was grappling with my own limits as a new parent, unable to do the “nights and weekends” level of work that our investors expected, and our team was just getting… tired. Our CEO was starting to do that work on her own, and it just wasn’t fair to her.

Anyway, there came a point where we had to rip off the band-aid and part ways. It sucked. I was really happy to open source Brainstory, at least, to keep it alive in some way, but it was a major bummer to be on that call where we said that scary phrase, “I think we’re done.”

I’m particularly happy though that we’re all still friends. So many times I’ve seen startups break up because founders have a huge falling out, or people argue to the point of never wanting to see each other again. I think we were all feeling a little wounded, but also ready to move forward and be glad that we did what we could, and tried our hardest.

Looking forward

This month has been pretty dang busy, honestly. Earlier this year I booked a bunch of talks (where I originally was going to promote Brainstory, and now I can just blab about whatever I want! Woo!) at some events this month, so even though I’m thinking about my next role and what I want to do in general, I feel like I’m working as hard as I would if I still had a full time gig. I’ve been working on (read: over-engineering) my website here, planning out some of my projects that I’ve been putting off, and just spending as much time with my baby while I can between events.

After being in startup leadership for the past couple years, I’m definitely trying to be intentional about where I might go next. I made a little list of what I’m thinking of for a future role:


  • Flexible work schedule
  • Nice people
  • Decent salary
  • Ability to work on my side projects

Must nots

  • Heavy on the politics
  • They try to own my time/projects outside of work

Nice to haves

  • 4 day work weeks
  • Enough comp + benefits that Joe (my husband) could be a stay-at-home dad
  • Education budget
  • Unlimited vacation
  • Fitness/wellness budget
  • Working in/on open source in some way

Now, I’m not sure if I’ll be able to find something that checks all of these boxes, and I’m sure some of these seem pretty picky. But, I figure if I put it out there, I can at least have a list to refer to if I need a gut check.

Until then, I’ll be speakin’ and hackin’ and bloggin’!

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