Gumshoe AI - Pre-Seed Round

$2M Raised

Seattle just birthed a new kind of detective, and no, it’s not another tech bro with a trench coat and a pitch deck full of vaporware. This one doesn’t chase criminals. It chases relevance. And it goes by the name Gumshoe AI.

Here’s the play: AI search is already reshaping how people discover products, brands, and answers. ChatGPT, Gemini, Claude, they’re the new gatekeepers. Forget the blue links. If your brand doesn’t make it into their response? You don’t exist. Period. That’s the problem Gumshoe AI is solving, and they’re not tiptoeing into the scene, they’re kicking in the door with a $2M pre-seed round led by the always-savvy folks at Pioneer Square Labs.

Now let’s talk founders. Todd Sawicki isn’t some hobbyist building AIanalytics in a garage. He helped turn ICanHasCheezburger into a meme-fueled media empire before memes became marketing gold. Patrick O'Donnell? He helped bring Starwave to ESPN and co-founded UrbanSpoon, back when most people still picked restaurants by flipping through Zagat. These guys don’t trend-chase, they trend set. Together, they saw the glitch in the matrix: brands spending years on SEO just to get tossed in with competitors by an LLM that couldn’t care less about your keyword density.

Gumshoe AI exists to fix that. The platform simulates hundreds of real LLM conversations to tell marketers how they’re showing up, or not showing up, when consumers ask the questions that matter. Real-time tracking. Competitive analysis. Search personas. Recommendations with actual teeth. This isn’t another dashboard collecting dust while your agency tells you everything’s fine. It’s clarity in the chaos. A compass for the AI search wild west.

They’re already gaining traction with agencies smart enough to realize AI discoverability isn’t a “nice-to-have.” It’s the battleground. Their launch caught attention on Hacker News, and the insights they’re publishing on The Discoverability Report are giving the space the heat it desperately needs.

Head of Product Stan C. brings the kind of résumé you usually only find in tech fairy tales, Y Combinator alum, Harvard University MBA, and the kind of product chops that turn good ideas into indispensable tools.

No flashy slogans, no gimmicks, just a team that understands AI search better than the algorithms running it. So if you’re a brand still relying on yesterday’s playbook to win tomorrow’s search war, maybe it’s time to call in the gumshoes.

Let’s connect and keep the momentum going across the tech ecosystem. Whether you’re a founder shaping the future, a leader driving change, a VC backing bold ideas, or an investor spotting the next big thing—together, we’re pushing boundaries. Proud to be building the future with you.

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