Company building

Company building

Company building

How I Messed Up Our AI Strategy: The Big Pivot That Didn't Pack a Punch

Superthread founder David Hasovic gets blunt about the failed first attempt at going all-in on AI, from model selection errors to the 'better product' trap.

A cinematic 1920x1080 landscape illustration of a founder standing at the crossroads of a tech pivot. The left side shows a dim, legacy workspace cluttered with tangled wires and old monitors, representing technical debt and stagnation. The right side glows with a vibrant blue light, featuring sleek UI panels and neural network motifs that symbolize AI-driven innovation. The central figure stands between these two worlds, reaching toward the future, illustrating the transition from outdated systems to high-performance, intelligent software.

May 17, 2025

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David Hasovic

The Big Pivot That Didn't Pack a Punch

At the end of 2023, I made the decision to radically change Superthread and go all-in on AI. However, I messed up. Here’s what happened.

When we started, before the modern LLM era, our goal was simple: build the fastest team collaboration tool that’s actually useful. That said, my friend Hugh Hopkins from Delegate (Acquired by Landbase) was already obsessed with ChatGPT 1, and I should have paid way more attention!

Anyhow, we made some big strides and the result was a product that was about 20% better than the competition and in some cases 100X faster. But it turned out, users neither cared about small improvements nor speed that much.

Coming from B2C, I learned a hard B2B lesson: the better product doesn’t always win. That’s a topic for another time.

Ultimately, we didn’t get the knockout punch I originally envisioned. That breakthrough moment, the big leap forward, felt further away than ever. And that’s when I hit a wall. I was stuck, trying to crack a new model for collaboration dynamics, but nothing was clicking. It was honestly a low point.

Then, suddenly, it hit me, the answer was staring me in the face all along. I told the team, “Starting January, we’re going all-in on AI.”

But, well… things didn’t exactly go as planned.

Catching Up vs. Pushing Ahead

It’s January 2024, and we’re kicking off the year with fresh energy.

I’ve always had a thing for AI. Back in secondary school in 1997, I built my first chatbot using QBasic, and my first job was with a startup run by one of my AI professors. With new LLMs, the time felt right; we jumped in and committed to making our company AI-driven.

Soon enough, we had our own set of tools up and running:

  • RAG search

  • Text rewriting for different tasks and documents

  • Duplicate detection

  • Auto-tagging

It was a solid start, and within a few months, we’d caught up with the industry. But there was a snag: we were only catching up, not pushing ahead. We were doing the same standard AI features as everyone else, but nothing groundbreaking. We weren’t focused on where AI could go next; we were stuck where it was.

Execution Failures and the Fizzle

Execution was another challenge. We initially picked the wrong models for vectorisation, and our auto-tagging model, trained on GitHub issues, didn’t work well either, it could only handle bugs and requests!

Eventually, my enthusiasm fizzled, and the project stalled after a few months. I’ve been here before; I need that spark early on or I find it hard to stay excited.

Looking back, not pushing Superthread to become a full AI company was a big miss. Now, we’re making up for that and aiming to get it right. Once we’re there, we’ll be sharing some of the magic we’re creating.

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