The Savvy Diaries No. 4 — That's Foundertainment!
Discovering my true calling in the Finger Lakes, where I literally got the show on the road
A few months ago I was hit up by my best high school friend’s best business school friend, a guy I hadn’t seen or talked to since our mutual’s wedding nearly a decade ago. He runs a venture fund based in Rochester, NY called Impellent, which was preparing to host its fifth annual Finger Lakes Summit — a gathering of 140 founders, investors, and tech industry leaders at the four-star Lake House on Canandaigua in the bucolic heart of upstate New York’s Finger Lakes region — and in search of a keynote entertainer for the event, he kindly thought of me.
I assumed he wanted me to host a trivia show for the attendees. They alllll want trivia. But to my surprise, they wanted “something different.”
The timing couldn’t have been more perfect, as “something different” is exactly what my team and I at Savvy have been building for the past 18 months. With AI effectively “taking trivia’s job” as a viable format for a live, interactive mobile game show offering high stakes cash prizes (it’s simply too easy to cheat), we developed a word puzzle game layered with a novel Host vs. Audience interaction, providing the most “different” entertainment experience on the market today.
I pitched the event organizers on my hosting an episode of Savvy live from the Summit in our first-ever “road show,” and they were all in.
There was only one tiny issue to resolve…
Could we actually pull it off?
Between our initial weekly test shows last fall and our TextSavvy beta season this winter/spring, we have produced dozens of episodes from studios in New York, New Jersey, and Los Angeles. Each has had an on-site producer (or two) setting up the lights, camera, and mics and running the OBS livestream. We also have had one (or two) members of Team Savvy joining remotely, coordinating stream specs with the producer and assisting with our makeshift GoogleDoc “teleprompter.”
In preparing for this Summit show, it became clear I’d be flying solo. We couldn’t manage getting our own producer to Canandaigua — an Iroquois word meaning ‘No Direct Flights’ — and after speaking with the Summit’s tech staff, we realized we were going to have to ‘raw dog’ this stream: no dedicated professional cameras or lights, no music or graphics or prompter… just me, a mic plugged into my laptop, and a pandemic-era webcam I found while unpacking boxes in my parents’ basement. I’d be hitting ‘Start Stream’ on OBS — in a barn with spotty wifi — and hoping for the best.
I arrived at LaGuardia at 9am for my 10:15am departure to Frederick Douglass Greater Rochester International Airport — quite possibly the only “International Airport” without international flights — and checked the board: ON TIME. Not five minutes later after swiftly moving through a sparse security line, I checked the board again: CANCELLED.
Oooooookaaaaaayyyyyyyyyyy…
Turns out some disruptive weather in the midwest had thrown a wrench into Delta’s gears, leaving thousands of customers suddenly stranded. In line for customer service where I was hoping to get rebooked, I clocked a fellow Summiteer and chatted him up between dueling pings of emails and texts from the event producer, Sasha. He was a Westchester kid like me, a former Scarsdale Raider now living in Miami and heading up sales for a startup that bills itself as the “Docker AI Development Platform for Regulated Large Enterprise” and touts “112 AI guardrails across 18 categories—born from thousands of real regulated go-lives.” Don’t ask, don’t tell.
Sasha heroically corralled the eight of us stuck at LGA into a Sprinter limo driven by some poor bastard who woke up that morning thinking he had the day off and instead got handed a 12-hour round trip to bumfuck and back. The ride itself was pleasant, broken up by a lunch and bathroom break at Jimmy John’s (I chose the Totally Tuna) and sporadic chatter with my bus mates: a founder of an AI-powered legal automation platform, a founder of an AI-powered “digital twin” production platform, a founder of an AI-driven executive talent hiring platform…
And what do you do?
”I host game shows.”
I’ve never considered myself a “tech guy”… in fact, quite the opposite. Ever since I learned what a Luddite was, I’ve identified as one. Rather than getting hyped on “the latest thing,” I tended to gravitate towards their earlier equivalents. Nok Hockey over Air. Cassette and VHS over CD and LaserDisc. My gaming console topped out at Sega Genesis. I spurned the iPod and was the last of my peer group to give up his dumb phone. Five years late to Twitter. Seven years late to Instagram. Snapchat? Good grief. Vine? Good riddance.
I’ve never once bought a Blu-Ray.
This mindset carried over to my professional ambitions. I spent my entire adult life attempting to build a career on the creaky floorboards of “show biz,” seeing myself in line with a long tradition going back to the vaudeville tramps and Catskills tummlers. I worshipped Groucho, Chico, and Harpo; Benjamin Kubelsky and Melvin Kaminsky; Dick Cavett and Johnny Carson; Larry David and Jon Stewart. I respected the hustle and grind required to “make it.” I romanticized the idea of needing to “get passed” at a club in order to perform there. I appreciated the Gate Keepers, even if they were keeping me out.
To hell with calling everything “content,” I thought. Curse these “Snapchat comedians.” Blast these “internet celebrities.”
And then I became one.
In 2017, I was hired by a NYC-based startup called Intermedia Labs to host a trivia show on their new mobile app called HQ. Within six months, I was broadcasting live to millions. Getting mobbed for selfies. Being offered five figures to appear at Bar Mitzvahs.
But the most transformative aspect of that dizzying experience was having my eyes opened to an entirely new world of tech, or “tech world.” In this alternate reality, people my age and FAR YOUNGER were going around calling themselves “founders” and inexplicably convincing older rich people to fork over millions of dollars to fund their whimsical notions. Somehow I had walked assbackwards into this VIP playground, piggybacking off a tech company to viral fame and cutting the line to “show biz success.” Without an agent, a manager, a late-night credit or even a pass from a club booker, I had finally made it.
Fuck the Gate Keepers.
Once my stupid, stubborn little brain had been forcefully exposed to it, the power inherent in this new media landscape was immediate and obvious: digital content platforms and mobile apps could turn anyone, anywhere, into “a viewer” — and maybe even a fan.
Now here I was years later, if not a full-blown “tech guy,” a tech adjacent guy, thrust into my first entrepreneurship conference with a rare opportunity to not only exercise my showbiz muscles as an inveterate comedian, but to demo my product as a bootstrapped founder — with rapidly thinning straps — in front of an attentive crowd of potential investors, no less!
Did I feel closer to the hard-luck limo driver than my fellow founder-passengers, who spoke as breezily about agentic client solutions and API endpoints as they did about summering in St. Tropez and Taormina? Sì, bella! But then I hit the stage in the bathrobe and slippers I found in my room, hammered out a few jokes like:
How you gonna call it “Artificial Intelligence”?
SHE SEEMED PRETTY REAL TO ME!!!
and hit ‘em with Savvy.
Sasha had asked if we could present a custom game show experience exclusive to the in-person crowd, but without that capability built into our product, we compromised by scheduling the show just before airtime, without any external promotion. Despite these best efforts to keep it under wraps, nearly 2,000 Savvants joined the stream thanks to the automated push notification, instantly lighting up the chat with helpful messages like SHOW HOLE and EAT THE RICH.
The rich ate it up. The show was a hit. I walked out of that barn with $3 million in SAFE notes,1 four invitations to connect on LinkedIn, and the funny feeling of coming full circle. In mashing up “start-up” with “stand-up” and “business” with “show,” I had found new meaning in my beloved show business. I could be a comedian and be on the cap table. I could make pitch decks and dick jokes.
I’d found my calling: Foundertainer.
You better believe I’m already making plans to attend next year’s Summit, with Savvy on board as an official sponsor. I’ve even noodled on a few slogan ideas. In the meantime, look for me going live beside a lake near you!
(metaphorically speaking)