The Pickle: Volume 27

Summer is officially here and it’s about damn time. Let’s go

Last week, we wrapped up our Apollo partnership with a bang—massive turnout, nonstop games until 10:30 AM, and some serious highlight-reel moments. Huge shoutout to everyone who came out and made it one of the best days yet. 🙏

If you missed last week, don’t worry, we’re doing it again this Friday. 💥

And then next Friday. And then the Friday after that. And after that. And after that after that. And every Friday until the end of time!

Pickle lifestyle. Pickle dream. Pickle community.

See you there for bagels + coffee + community. Nothing gets me more fired up.

👀 Opportunity

We’re actively looking for summer sponsors and partners for Tech Pickleball!

🥒 If you want to reach the 1500+ founders, VCs, operators, and execs in our community in a unique way, reach out to Skyler or John and let’s chat about doing something epic!

Skyler @ optemization.com

John @ knock2.ai

Or just come up to the guy in the pickle hat or the Italian guy 😉 

🚨 This Week’s Game Plan:

Let’s just rip and have ourselves a damn good time

⏰ Show up early. Paddle raffles, sunshine, and coffee/bagels all go fast.

☀️ It’s going to be hot, so highly recommend bringing water and sunscreen!

🥒 Pickle Fun Fact of the Week

Pickles Were One of the First Jarred Supermarket Foods

In the early 1900s, as mass food production took off, pickles became one of the first foods sold in glass jars in American supermarkets. Their long shelf life, bright color, and visibility in clear jars made them perfect for early packaged food displays. Jarred pickles were eye-catching, trustworthy, and quickly became a pantry staple — helping set the stage for the modern grocery aisle.

**You thinking what I’m thinking? Probably not but I’m thinking that makes us trendsetters!

🏓 Stuck in a Pickle: The worst decision I ever made

Chasing the bag isn’t always worth it

This was the worst decision of my life.

But what I learned will stay with me forever.

Story time. Buckle up. (Unintentionally ironic, that will make sense later)

After I moved to NYC ~3.5 years ago and decided the Fanduel role ultimately wasn’t for me despite being their #1 outbound sales rep (didn’t like the morality of selling gambling)

I had to figure out my next move.

So naturally, I decided to go sell lasers.

**really they're medical devices but more fun to say lasers

Gambling → Lasers, yep you read that right.

Why? The money, straight up.

If you can succeed in medical device sales, you will make bank. Simple as that.

And as a 23 year old who just moved to NYC, it sounded pretty damn appealing.

There was just one problem.

I don’t know how to drive.

**had driven less than 10 times before this and barely have a license

My territory was NYC/NJ and it required driving 6+ hours a day minimum.

And oh, you have to cold call while you drive.

Everyone, and I do mean everyone, told me this was a terrible idea.

And they were right, but I didn’t care. My mind was made up.

What better place to learn how to drive than NYC/NJ during rush hour while cold calling, right? 😅

Well, you can probably guess what happens next.

My first month was actually off to a really strong start.

I was booking meetings left and right and was actually labeled “Most exciting new hire” at their convention in Florida.

And it was all going great until.... BOOM!

I thought I had enough space but I didn’t.

I smacked straight into the back of a Benz while on a cold call trying to get out of a crowded parking lot.

On the drivers 9 year old daughters birthday who was in the car.

Thankfully, no one was hurt. The damages were extremely minor.

I sold the car and quit the next day.

What’s the lesson here?

Chasing the bag is not always worth it, no matter how big the bag is.

NYC/NJ is a terrible place to drive in when you don’t know how to drive.

Turns out talking about Notion every day is a lot more fun anyway.

Failure is temporary, learning is forever.

NYC Tech Pickleball update

Theme of the week:

SUN IS BACK SUMMER IS BACK BABY

Enjoy pics of last week!

That’s all for this week. Smash you Friday.

Thanks as always to everyone who comes out and makes our community special!!!

Bring sunscreen, energy, and maybe… a backup paddle 😏

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 🙂

Skyler & John