Show Notes
"The worst thing you could do is go look at what your competitors are doing and try to replicate what they just said on your website. You're just going to look like everybody else.” - Ryan O'Hara
Ryan started as a video production intern at Dyn, hoping to make ads before pivoting into cold prospecting instead, becoming the company's first BDR.
He helped scale the sales team from three reps to over a hundred before Oracle acquired the company for north of $600 million.
He carried the same instinct through LeadIQ: business messaging didn't have to be boring.
While the sales tech space drowned in "hit your number" energy, Ryan sent music videos to prospects and made 90s-style jingle ads for target accounts like Zoom and Logitech, then watched those videos rack up thousands of organic views from inside the exact companies he was trying to reach.
His first Pitchfire venture nearly ended when his sole investor passed away from cancer mid-round.
He rebuilt it into a new company, investment infrastructure for VC firms still running deal flow through Typeform and Google Docs instead of anything built for it.
His read on outreach in the AI era hasn't changed: reply rates have crashed, AI-written pitches all sound the same, and what still breaks through is a real detail two humans actually have in common, not a value prop.
"Be yourself the whole time. If you're an SDR who makes music, put music into your prospecting. Life doesn't have to be one octave lower just because you're at work."
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