How 200 Awkward Double Dates Launched My Career
What started as a joke became my entire career strategy.
My best friend and I went on more than 200 double dates with complete strangers from the internet. If you’re doing the math, that’s an absurd number of hours spent pretending to be deeply fascinated by rescue chihuahuas and adult kickball leagues.
My buddy Dave and I posted a Craigslist ad linking to a YouTube video inviting women to double date us. Hundreds responded. We documented the awkward encounters and uploaded those, too. To viewers, the “Double Date Us” series looked like a weekly exercise in self-inflicted discomfort.
But in hindsight, those dates became the foundation of my career.
We had always dreamed of pursuing comedy professionally, but we understood that passion alone wouldn’t get us there. Every comic at an open mic has passion. What we stumbled into, however, was something far more valuable: a proprietary dataset of bizarre, real-world dating experiences. We weren’t just another comedy duo—we were the guys who survived the internet dating trenches.
That strange social experiment became the core material for a live show at the People’s Improv Theater, a decade-long national tour, multiple appearances on late-night television, and eventually our own show with NBC. One highly specific experience opened the door to an entirely new industry.
The chain reaction of assets
This isn’t just about gaining experience and applying for jobs. It’s about leveraging unusual opportunities that set you apart—using one distinct advantage to unlock the next.
Take comedy touring. It was a logistical grind: living out of suitcases, dealing with delayed flights, performing in college cafeterias where the audience competed with a sneeze guard. Instead of simply enduring it, I analyzed it.
With hours to kill in unfamiliar cities before shows, I started visiting local craft breweries.
In the early 2010s, the American craft beer scene was exploding. Established beverage journalists were tied to major cities like New York or Los Angeles. My grueling tour schedule gave me something they didn’t: scale. I could visit breweries in all 50 states, taste beer at the source, and meet brewers face-to-face.
That advantage—born entirely from the friction of touring—gave me the authority to pitch and land bylines in major publications like Food & Wine, Esquire, and Playboy.
The “follow your passion” trap
You’ll often hear advice to “follow your passion.” It sounds good, but in today’s world, it’s increasingly ineffective.
Passion is not rare. It’s a commodity.
Millions of people are passionate about craft beer, writing, or business strategy. If you build your career solely around what you love, you’re competing with an endless pool of people who love the same thing—and increasingly, with algorithms that can replicate that output in seconds.
What actually matters is what I call a claim—the first pillar of a “Mosaic Fortress.” Your claim isn’t a dream job. It’s your defensible white space: the territory that only your specific, unconventional background allows you to occupy.
The asset audit
To find your claim, you need to stop evaluating yourself based solely on skills and start conducting an asset audit.
Look at the strange, overlooked advantages in your life. What do you have access to that others don’t?
Your real edge rarely appears on a resume. It’s usually hidden in detours, constraints, and seemingly unrelated experiences. The frustrating or disconnected parts of your path often hold the most value—if you examine them closely.
Ask yourself:
Do I live in a market others ignore, giving me unique insight into a specific audience?
Do I have access to a niche or closed community through a past job or hobby?
Does my work expose me to systems, processes, or challenges that others avoid?
Algorithms don’t have physical presence. They don’t navigate awkward social situations or endure grueling travel schedules. They don’t accumulate lived, logistical experience.
When you audit your real-world assets, you stop competing on raw talent—and start competing on positioning.
Don’t follow your passion into a crowded room.
Audit your assets, find your claim, and build where no one else can stand.