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.

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.

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.

Swipe-worthy structure:
1. Unexpected hook (teen dropout email).
2. Stacked credentials (MIT, ISS, Putnam).
3. Rocky-montage work ethic (Wendy’s + Yankees).
4. Concrete payoff (15-second expense).
5. 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.

Opossum one pager flyer

Coffee at a Glance