We launch HeyHelp next week (🎉). As I look back on the journey so far, one thing stands out: we’ve made choices that go against the grain.
As a second-time founder, I’m not relying only on gut feeling. I’m re-using what worked with DragApp (and deliberately avoiding what didn’t).
Here are four of those “unpopular decisions.”
1. Charging early users, early
Conventional wisdom says: polish the product, get traction, then monetize. We did the opposite.
We charged before launch (at a price far below the recurring value) to get HeyHelp into the hands of people who felt the problem deeply enough to pay for a raw, early-stage product.
That mattered because it:
- Rewarded our earliest supporters.
- Helped fund development.
- Brought in thoughtful feedback from invested users (not just opinions).
That filtering effect mattered more than free sign-ups ever could.
2. Building for adaptability, not prediction
In The Next Great Distribution Shift (incredible piece btw), Brian Balfour argues that breakout companies win by betting early and aggressively on the right distribution channel (eg. ChatGPT or Gemini).
We went the other way. We built adaptability into the core, and even made it our differentiator.
Sure, ChatGPT may look ahead today with higher retention and stronger memory. But will it still be the winner in five years? Honestly, we don’t know. Neither do you. So we designed HeyHelp so you don’t have to care.
Users can bring their own model, swap API keys, and evolve patterns as their inbox evolves. Right now, we’re the only ones in our space taking this approach.
3. Shipping fewer features, going deeper
The temptation is to launch with a long feature list to look “impressive.” At DragApp, we did that. It backfired: many of those features were half-baked, and we’re still paying down that debt.
We’re launching HeyHelp with two. That’s it.
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Sorting emails (surfacing what requires action vs. what can wait).
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Drafting replies in the user’s own tone.
And it’s already saving users 30+ minutes a day (according to them).
4. Choosing boring clarity over shiny hype
We didn’t build an animated website full of metaphors about “transforming the future of work.” We showed screenshots of Gmail, with emails getting sorted and replies drafted.
It might look plain compared to other SaaS sites. To the extend that a few days ago a stranger even called ours “the most refreshingly boring SaaS landing page” (ouch 😄).
But the result? People immediately understood what HeyHelp does. And that clarity built trust faster than any fancy design could.
Looking forward
None of these decisions felt easy at the time. They were all bets against the grain. But they gave us momentum and, more importantly, trust from early users.
If there’s a lesson here, it’s this: don’t fear the unpopular decision, as long as you’re clear about why you’re making it.
