Aaron O'Leary

What's one pain point you have as a founder right now? Let's collab on solutions

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Nobody said running a startup was easy but some issues whether it's increasing DAU, perfecting ad copy, increasing MRR, hiring, or whatever can be pull your hair out levels of frustration.


What's one pain point you are struggling with at the moment? Drop it in the replies and then help someone else based on your experience!

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Ashley from Shadow

One pain point right now: figuring out repeatable, non-cringe ways to show off product value in short-form video.

We’re building Shadow, an AI assistant that handles meetings and follow-ups, and while the tool works—it’s snappy, useful, solves real workflow problems—capturing that “aha” moment in a way that actually hooks people on TikTok/Instagram/YouTube Shorts is a whole different beast.

We’ve tried POVs, screen recordings, even fake skits, and some land... but most fall flat. The formats that go viral don’t always align with what feels authentic for our product or audience (think: execs, PMs, sales teams—not necessarily Gen Z meme lords).

Curious if anyone’s cracked the code on this—or found a format that balances credibility + virality?

Also happy to jam with anyone else struggling with visibility, video workflows, or AI product positioning. We’re in the trenches too.