I recently heard Will Guidara on a My First Million (MFM) podcast episode, and I immediately saw the overlap between his restaurant service philosophy and digital customer experience.
Most companies run theirs like a Denny’s at 3am. Acceptable enough, but nobody’s writing home about it.
The Restaurant That Changed Everything
Will Guidara’s Eleven Madison Park did something crazy. They hired one person whose only job was to execute everyone else’s service ideas. Not come up with them. Just execute them.
A server overhears a European couple missing hot dogs from their NYC trip? The Dreamweaver materializes a fine-dining hot dog course that night.
Someone mentions it’s their mom’s birthday? Custom dessert appears.
The insight: Great service isn’t about grand gestures. It’s about noticing small things and caring unreasonably about them.
Now translate that to product.
Three Categories That Change Everything
OSFA: One Size Fits All (Universal Friction Elimination)
Restaurant version: That complimentary cognac with every check. Everyone gets it. Everyone appreciates it.
Digital version: Fixing the stuff that annoys EVERYONE but nobody complains about because they think it’s “just how it works.”
Your opportunity: What’s your cognac moment?
- Error messages that actually help instead of blame?
- Onboarding that feels inevitable, not lucky?
- Documentation that anticipates the next question?
OSFS: One Size Fits Some (Pattern-Based Personalization)
Restaurant version: Tiffany box for engagements. Chewy’s sympathy flowers when a pet dies.
Digital version: Pre-planned responses to common business milestones.
Product launch coming? Here’s how to scale. Security incident brewing? Here’s the playbook. Team growing fast? Here’s the onboarding guide.
The trick: These aren’t custom. They’re systematized empathy for recurring patterns.
OSFO: One Size Fits One (Signal-Driven Customization)
Restaurant version: That NYC hot dog course. Totally custom. Totally worth it.
Digital version: Individual customer signals routed to create unique solutions.
But here’s where it gets interesting—every OSFO solution should become OSFS or OSFA over time.
One person needs a custom knowledge article? Great. Now it helps 1,000 people.
The Digital Dreamweaver System
Will carved out a dedicated role for execution of these ideas, the Dreamweaver. In the digital world, we can leverage systems to assist us.
The flywheel becomes your Dreamweaver:
- Community catches the signal (server overhearing conversation)
- Intelligence identifies the pattern (Dreamweaver recognizing opportunity)
- Orchestration routes to the right fix (making it happen)
- Knowledge preserves it for others (next time it’s automatic)
Result: What was once OSFO (custom) becomes OSFS (pattern) becomes OSFA (universal).
Making Excellence Mandatory, Not Optional
Here’s what most companies miss about service culture:
Will Guidara didn’t just encourage great service. He made it mandatory. Required gestures per shift. Accountability systems. Praise more than criticism.
Digital translation:
- Required prevention metrics per sprint (not optional nice-to-haves)
- Team celebrations for preventing problems (not just solving fires)
- Regular reviews of τ (routing rate), ω (fix velocity), D (ticket density)
The meta-signal: When prevention work is core responsibility, not bonus work, everything changes.
Start With Your Cognac Moment
You don’t need to rebuild everything tomorrow.
Find your universal friction point. The thing everyone experiences. The thing nobody complains about because they assume it’s “just how it works.”
Then fix it unreasonably well.
That’s your cognac moment. That’s what makes people say “Wait, product can do that?”
Because here’s the truth:
Great restaurants don’t compete on food quality. Everyone has good food at that level.
They compete on how they make you feel.
Your product should do the same.
