Last year, we spent half a year courting a mid-market company. We did endless demos, built a custom integration for their legacy system, and jumped through every hoop. Finally, we closed a $2,000/month contract. The Head of Operations, who loved our product, was our internal champion and promised it would be a massive success.

Three months into the contract, our champion resigned.

Two weeks later, we got an email from the new VP of Operations. He wanted to "review the software stack." We jumped on a call, and he told us he was canceling the contract. His reasoning? "I didn't buy this tool. I don't see the ROI. And frankly, I want to consolidate vendors and use the tool my old company used."

I was devastated. We had built custom features for them, spent weeks onboarding their team, and the product was actually working perfectly for the users. But because the person who signed the check was gone, we were treated like an unwanted stepchild.

We spent months cleaning up an interface that worked fine but looked a bit dated, only to watch users get completely disoriented by the new layout.

Even though the new design scored much higher on aesthetics and modern UI tests, our churn spiked because people couldn't find their regular daily workflows anymore. Muscle memory matters way more than pretty padding.

How do you roll out a massive UI overhaul without frustrating your oldest power users?

Just to correct myself: the wave of layoffs is not coming, but it has already passed through.

Meta, Amazon and other big companies have started laying off workers because AI will take your jobs.

I feel like internal documentation has become a losing battle lately. Code changes endpoints move around, and setup configs tweak every few days but no one wants to pause momentum just to write static markdown files. Eventually onboarding becomes a game of "ask the lead dev on Slack" because the official docs are useless.

We're trying to figure out if there's a lightweight habit that actually sticks like auto generating API docs from code comments or keeping docs right inside the codebase itself.

If you work on a fast moving project what's one actual practical workflow that kept your docs from falling behind without feeling like a chore?

Some companies are love brands for me, and I d like to support them. Others I see growing, and I d love to ride the wave. :D

Do you have any companies you d like to invest in, but that don t have a public offering yet? Which ones?

I changed two sentences on my signup page. Not the design, not the pricing, not the flow. Two sentences.

Trial to paid conversion went from 9% to 18% in three weeks.

I came up with this concept after I failed to set New Year s resolutions at the beginning of 2023 and was disappointed that I didn t achieve much.

Since 2024, I ve been practising quarterly goal-setting.