Want Calvin to file your expenses? Ad
Great Ogilvy style print ad and story from Eric Glyman about hiring a 17 year old high school drop out.
He said:
I first met Calvin in 2016.
Karim and I had just launched Paribus. We weren’t a big company. Our office was my kitchen table.
So when an email from a 17-year-old high school dropout landed in my inbox asking for an internship, I skimmed by it. Thankfully, Karim didn’t!
- Admitted into MIT at age 16
- Code running on the International Space Station
- Top 20 in the country in the Putnam Math Competition
Calvin arrived on his first day in a T-shirt he wore representing the United States in a programming competition. Three weeks later he’d built an AI model to automate refund decisions. This was years before people knew what AI even was.
Fast forward four years. Karim and I start Ramp. Our first phone call? Persuading Calvin to join as a founding engineer.
The challenge: make filing an expense as easy as taking a photo of a receipt!
Fortunately, Calvin looks at hard problems the way a dog looks at a bone.
I watched him come back to the office every night, just as I was leaving, Wendy’s in hand, no small talk, working because he wanted to, only pausing to watch The Yankees’ playoff run.
Eighty thousand expenses a day are now submitted using the code he wrote. Each one takes just 15 seconds, not 15 minutes. That’s 20,000 hours of work saved every day!
Why am I telling this story?
I think founders get too much credit. The single most important thing we do is hire people smarter than us.
Phil Knight had Jeff Johnson, who drove to track meets across the Pacific Northwest and sold the first 3,250 pairs of Nike’s from the boot of his car. That’s why you’re wearing Nikes.
Steve Jobs had Ken Kocienda, who mapped thousands of thumb taps to solve the seemingly impossible problem of touch-typing on glass. That’s why you have an iPhone in your pocket.
Calvin is one of those people.
Who wouldn’t want him to file your expenses?
Image description
- A vintage-looking print ad:
- Polaroid snapshot of a young guy (Calvin) proudly holding a giant American flag.
- Background sprinkled with faded receipts—subtle nod to “expenses.”
- Big, bold Ogilvy-style headline dead-center: “Want Calvin to file your expenses?”
- Tight body copy beneath that reads like a mini hero-story résumé.
Positive aspects
- Headline stops the scroll—direct, intriguing, and benefit-oriented (“file your expenses” ≠ sexy, but “Calvin” makes it curious).
- Visual hierarchy is pure Ogilvy: picture ➜ headline ➜ body copy. Even a caveman’s eyes would know where to go.
- Receipts in the background instantly connect the dots: this isn’t a random flag selfie—this is about expense automation.
- Story copy humanizes Ramp’s tech: you’re not buying software; you’re buying Calvin-level genius bottled in code.
- Social proof overload: MIT at 16, code on the ISS, hired by Google at 19. Credibility bar = roofless.
Key takeaways
- Hire people smarter than you, then get out of their way—your company’s moat is talent, not the founder’s ego.
- Tell product stories through human stories; “Calvin” is more memorable than “AI-powered receipt parser.”
- Specific numbers (80,000 expenses/day, 20,000 hours saved) make intangible software benefits feel real and massive.
- Ads that read like mini case studies (Ogilvy style) pack authority, narrative, and CTA in one punch.
- Founder myth ≠ solo act—celebrate the supporting cast to build stronger employer and customer brands.
Additional insights
- Swipe-worthy structure:
- Unexpected hook (teen dropout email).
- Stacked credentials (MIT, ISS, Putnam).
- Rocky-montage work ethic (Wendy’s + Yankees).
- Concrete payoff (15-second expense).
- Moral of the story (hire smarter).
- “Expense software” is a snooze category; turning it into a superhero origin story makes it cocktail-party-talkable.
- Try this in your own marketing: swap faceless feature lists with a real user/employee narrative. If you can’t find a Calvin, at least find a mini-Calvin moment.
- Fun copy tweak idea: add a P.S. in the ad—“P.S. We’re hiring. Bring your own Wendy’s.” Humor + recruitment in one line.
