Hand up - Never in a million years would I have thought we’d make it to 30 freaking editions of The Pickle.

That’s crazy! Genuine thanks to everyone who braves through my cringey brine jokes and goofy pickle facts to stay up to date on what’s best happening with Tech Pickleball.

But like I said, I’ve written 30 of these now, you crazy pickleheads all know the drill already.

Blah blah blah, 7:30-9:30 tomorrow, McCarren Park blacktop, free bagels + coffee and the best community in the world.

See you bright and early tomorrow!!!

Pro tip: look for the guy in the massive pickle hat (ME!)

Time for what you really came for.

👀 Opportunity

We’re hosting the first ever Startup Pickleball Tournament in NYC

Are you a founder who thinks your startup has what it takes to take the whole city down?

Think your company has what it takes to be the pickle champion of the world??

We’ll see about that. But in the meantime, you should probably sign up here.

October 4th is going to be next level epic.

Here are all the details:

🥒 Pickle fun fact of the week

🎉 There’s a Pickle Festival in NYC Every Year

Lower East Side Pickle Day is a full-on dill-ebration:

• Where: Orchard Street, Lower East Side, Manhattan

• When: Usually a Sunday in October (exact date changes yearly)

• What’s it like?

  • Dozens of pickle vendors: from classic kosher dills to spicy mango pickles

  • Pickle ice cream, pickle cotton candy, pickle beer (no, really)

  • Games like “Guess the Pickle Weight” or a Pickle-Eating Contest

  • Live music, pickle-themed merch, and folks dressed in full pickle costumes

• Why it exists: The LES was once home to dozens of pushcart pickle vendors in the early 1900s. The event is part historical tribute, part chaotic brine-fueled block party.

• Pro tip: Go early. It gets crowded, and you don’t want to be waiting 45 minutes for a garlic spear while surrounded by 12,000 hipsters.

**Found our Tech Pickleball community offsite this year 👀d

🏓 Stuck in a Pickle: Content tip of the week

You never know who’s watching

An inbound cold DM from a CEO of a ~200 person Series B company led to a $70k deal.

And it wouldn't have been possible if I didn't post on LinkedIn.

Here was the DM:

"We use Notion, it's grossly out of date, and we need to do a mass overhaul. Want to have you chat with someone I work with who's looking at the project and get a potential idea of what that might look like either consulting or having you do it. "

He then intro'd me to his head of Rev Ops who was leading the project.

We hopped on a few calls to scope, I kept the CEO in the loop on every step and thing that was happening as the deal progressed. He championed us internally.

And boom, deal was closed within 2 months 🏦

But here's the thing.

That CEO had never engaged with a single one of my posts.

Not even a like.

But he was reading them.

And when the time was right, who was he going to reach out to?

Yep, you guessed it 👋

You never know who's reading your content.

Keep going. Stay consistent.

Don't stress over the short term results, believe in the long term process.

The vanity metrics don't matter as much as you think they do.

PS, know anyone else who's companies Notion is grossly out of date and in need of a mass overhaul? You should probably slide in my DMs too 😉 

NYC Tech Pickleball update

Theme of the week:

Humidity sucks. Tech Pickleball doesn’t.

That’s all for this week. Brine you tomorrow.

And who could forget the pictures??

Look at all those amazing smiling faces.

Thanks as always to everyone who comes out and makes it special

Pickle lifestyle. Pickle dream. Pickle community.

Ps, know anyone who might be interesting in partnering with Tech Pickleball?? Hit us up! We want to find more creative ways to expand and grow this community through awesome partners 🙂

Email us at [email protected] or [email protected]