Hey friend,
I'm testing a new format this week. Shorter, more of a roundup than a long essay.
3 things nobody in SaaS wants to say out loud: AI doesn't bolt onto old software. Most startup equity is worth zero. And the category I've been in for 12 years is quietly shifting under everyone.
That's what's below. Let me know what you think of the format. I read every reply.
1) I ended a $5M ARR business on purpose
This is the post that got the biggest reaction this week - 225,000+ impressions and 129 comments, a lot of them from founders quietly running the same experiment I did. Here it is in full:
I own Groove, a 12-year-old help desk doing $5M ARR. 18 months ago we tried to make it truly agentic. We couldn’t do it. So I had to end my $5M ARR business.
Everyone in B2B SaaS is currently sprinting past this realization.
I know the legacy help desk category from the inside out. I own one and customers actually like it. So in the AI era, we did what every incumbent is doing right now and tried to retrofit it onto the product we already had.
18 months later, we stopped.
And the reason we stopped is architectural, which is the part nobody bolting AI onto a legacy product wants to hear. You cannot tack AI onto a ticketing system built around humans clicking buttons. The data model is wrong. The workflows are wrong. The pricing is wrong. All three are structural, and none of them are fixable with a feature.
AI on legacy architecture is still a chatbot, just a more expensive one.
So we started over from zero and built Helply as an agentic system from day one, where you pay for outcomes instead of seats. 18 months in (8 months since launching) it’s at $1M ARR growing 7% a month, and most of it comes from people leaving the exact platforms still selling the retrofit.
If you’re bolting AI onto a 2007 architecture right now, in any category, I’d genuinely love to be wrong. I just spent a year and a half proving to myself that I’m not.
One important thing, especially if you’re a Groove customer reading this: Groove isn’t going anywhere. It’s still running, still fully supported, and still the same help desk you rely on. What I “ended” was the attempt to turn Groove itself into an agentic system - not Groove the business. If anything, Groove is what funds Helply. Two products, both alive, both here to stay.
Read the full thread and the comments here.
2) The truth about startup equity that most founders won’t admit
Short one, but it did 676,000 views - and I think it’s because everyone knows it’s true and nobody says it:
My best early hire at Groove left after 18 months for $50k more a year. I pitched him equity upside. He said he appreciated it, but he had a mortgage to pay. That equity would be worth zero today. He was right.
I still think about that conversation. If you’re recruiting on equity right now, it’s worth sitting with.
See it on X here.
3) This week’s video: AI is About to Change SaaS Forever (and nobody even realizes)
If the retrofit post was the “what happened to me,” this is the bigger picture behind it - where AI is actually taking software, why the shift from paying for seats to paying for outcomes changes the whole model, and why most of the category hasn’t clocked it yet.
Watch it here:
That’s the week.
If any of this hit home - especially if you’re the one quietly bolting AI onto an old product right now - just hit reply. I read every one.
All the best,