Optimize Your Words Like Eminem & Jerry Seinfeld

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An interesting moment occurred in a recent Startup Next session here in NYC. A really cool hardware-slash-SaaS product team gave their weekly <60-second pitch to the room, which included a few mentors. In Q&A, they asked the mentors for advice on how to effectively connect with retail store managers / owners to do some basic customer development. What we all quickly realized is that there was a clear lack of message optimization, which seems to be a struggle for some startups when efforts are moved offline.

Most of us have become accustomed to constant online measurement and optimization. Google Analytics, Mixpanel, KISSmetrics, CrazyEgg, and so on. We toil over call-to-action button colors and their effect on click rates, we heat map the shit out of every site page, and we switch out hero images and explainer videos to increase conversions by half percentages. But this optimization obsession doesn’t seem to translate outside of landing pages and websites.

Whether you’re cold emailing a potential partner or walking into a brick-and-mortar with the hopes of surveying an employee, you need to apply these same measurement and optimization techniques and philosophies. These efforts can range from nailing down your elevator pitch (though no one ever bought anything on an elevator) to tweaking your email subject line. The best communicators seek to disrupt expectations with both obvious and subtle modifications to their language.

Peep the amazing video below, a fast-moving and knowledge-packed rundown of rhyme scheme science in song writing. I’ve started it on a key part; a review of the complexity, innovation, and pattern-breaking of Eminem’s lyrics. I recommend you watch the entire thing at some point – it moves quickly and packs some unique knowledge.

People expect AABB and ABAB rhyming schemes – so when they hear internal rhyming like Em’s, they take notice. Now apply that to your cold email pitch. Avert those expectations of formalities and multi-line “About Us” rhetoric (“we offer an end-to-end cost effective solution that leverages data analysis to maximize ROI”) in favor of brevity and talking like a human. Some of the best responses I’ve ever received were to emails with informal subject lines (no words capitalized, strategically placed misspellings) and hardly a mention of “what we do”.

Why not craft an email or verbal pitch like a comedian does jokes? Here’s Jerry Seinfeld (yeah, I’m kind of a fan) walking us through his writing process:

See how he deconstructs the flow of the joke, from open to close? Each line informs the next, leading the audience on a guided journey with very intentional outcomes. Whether you’re emailing, cold calling, or face-to-face conversing (the horror!!), you need to be deliberate in your story telling. As Seth Godin mentioned in his elevator pitch post, your goal in a first-contact scenario shouldn’t necessarily be the sale, it should be to entice your audience into confirming the next step. This can be applied to micro commitments as well; a great email is structured for each line to sell the reader on advancing to the next.

Next time you’re thinking about optimization, consider how its principles can be applied to non-website / app situations as well.



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