The Distill - The Other Side of Cringe

Greeting Pioneers,

Everyone wants to build something, until it’s time to look a little stupid doing it. The first step toward anything real is almost always “cringe”. Zach Telander said it best - everything you want is on the other side of it.

Cinderblock’s opening, Vogt’s 25th, Jokester’s pivot - all proof that progress happens when you stop caring what the crowd thinks.

Everything You Want Is on the Other Side of Cringe

We live in a world where sincerity is dangerous. Caring is uncool. Where the moment you put yourself out there — write a blog, launch a project, chase a goal — you risk being called “cringe”.

That’s the tax you pay for ambition these days.

The internet rewards irony and punishes sincerity. It’s safer to mock than to make. Safer to throw stones at the doers than to do. The moment you care publicly, you hand the mob a weapon. But the mob hasn’t built shit. They just scroll through other people’s attempts, desperate for something to dunk on.

The loudest critics used to dream too. They just quit. Now they sit on the sidelines, performing detachment because detachment hurts less than disappointment. Calling someone else cringe is easier than confronting their own surrender.

If you want to make anything worth a damn, you have to pass through the cringe. You have to care loudly. You have to be willing to look stupid to everyone who’s chosen not to try. You’ll never get roasted by someone doing more than you. You’re only getting chirped at by people who spend their days correcting others online and chasing likes instead of progress.

There’s freedom on the other side of cringe. The freedom to build without flinching. To care without apology. To stop holding back for fear of losers on the internet calling you a loser.

Let them keep commenting. Let them keep performing detachment while you perform repetition. Every post, every project, every “cringe” moment pulls you further away from them.

“The only time critics can access their hopes and dreams is when they're sleeping. So when they wake up, make sure they keep watching you pursue yours.” - Zach Telander

Cinderblock’s Grand Opening: Friday Oct 17th @ 4pm

Food, drinks, games. If you've been watching us build the block over the past few months, come see what we've built.

This is the space where Velocity companies are grinding through their 12-week gauntlet – but Friday night is for celebrating.

Bring whoever you want. We're throwing open the doors and having a good time. RSVP here.

25 Years of Vogt Awards

Rachel attended the Vogt Awards 25th anniversary appreciation reception last week. Twenty-five years of backing early-stage Louisville founders with $25,000 non-dilutive grants and a 10-week accelerator program. No equity taken. Full ownership retained.

The highlight: hearing from Henry V. Heuser Jr, the son of the original donor who established the awards in 1999. His father's vision was straightforward - strengthen Louisville's economic health by supporting innovative businesses and inspiring entrepreneurship. A quarter century later, that vision is still funding founders.

One part that stuck: Vogt recipients have gone on to raise millions of dollars that flowed back into their companies and Louisville's economy. That's the compounding effect of patient capital invested early. You don't see that ROI in year one. You see it when a 2015 recipient is still building in Louisville in 2025, employing people, raising follow-on rounds, and reinvesting locally.

If you're an early-stage founder in Louisville, the next Vogt cohort applications open soon. $25K non-dilutive and a 10-week accelerator. No reason not to apply.

Demo Day is Thursday, November 13 at the Kentucky Derby Museum. Free event. Register here.

Jokester Learns Fast & Adjusts

Jokester entered Velocity planning to livestream comedy shows- coordinate a comedian, book a venue, sell tickets to fans who couldn't attend in person. Simple enough on paper. Dawson spent the first few weeks trying to sell shows and hit some friction.

"Coordinating comedians, venues, and fans is a lot more complex operationally than I expected," Dawson said.

“I also started talking more with bigger comedians, agents, and managers, and those conversations helped me see a bigger pattern. Most touring comedians don't just want to stream another show, they want something that actually helps them build their brand long-term. They want control, time to promote, and ways to maximize revenue from it."

The revenue piece is significant. Merch sales during live shows are a major income stream for comedians often matching or exceeding ticket revenue. Traditional streaming specials strip that out entirely.

"That was a big lightbulb moment for me," Dawson said.

So Jokester is accelerating into producing specials with integrated merch sales – something they planned to do eventually, now happening in weeks instead of years. Comedians keep control of their content, fans get access to live performances they couldn't attend, and merch revenue flows directly to the performer during the stream.

This is what Velocity is designed to surface. Founders who talk to customers, learn what matters, and adjust their roadmap in real-time instead of defending their original thesis for six months. Dawson's accelerating because customer conversations revealed a bigger, more valuable problem to solve.

"All in all, Jokester is gaining Velocity faster than expected in some ways and slower in others. I'm stoked to implement the stuff we learned and build an even better platform for comedians and fans." Dawson said. & that's how it's supposed to work. The finish line hasn't changed – revenue and customers by December. The path to get there just got sharper.

Know a comedian interested in bringing their online following into your live-set? Introduce them to Jokester for a pilot.

Note’s on The Distill’s co-EICs: Jack Crowdis & Rachel Edenfield

Jack runs the newsletter, helps run KYX. He’s a career startup kid, past founder, and current operator. Weekly contributor. Always editor.

Rachel’s the Founder/CEO of venture-backed Swell, and a driver of KYX. Routinely delivers the city’s sharpest long-form startup advice. Always re-edits Jack’s edits (including this bio).

Know someone who should read this? Forward it, or send them this link.

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Peace, Pioneers ✌️