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The Pickle: Volume 19 - The Return
Our weekly newsletter "The Pickle" is back in weekly action!
Skyler Birk-Stachon & John DiLoreto
March 06, 2025
We have never been more back!
It is my honor to finally be able to once again say….
It’s pickle pickle pickle time, pickle pickle pickle time, where ya at? Where ya at? There ya go!
**Like peanut butter jelly time, but infinitely better in pickle form
So let’s get the business out of the way.
This Friday morning, Indoors (aka not cold), CityPickle, Free Bagels and Coffee, Good Vibes, Familar Face, Infinite Smiles… and the best way to start your Friday morning:
SIGN UP NOW BEFORE YOUR PICKLES GO BAD:
https://lu.ma/otqmvn0t
Moving on to the fun stuff!
Wait what the heck… why are you in this section if you didn’t sign up above?
Go back, sign up and then come back!
Pickle fun fact of the week:
The largest pickle on record was made in 1999 by the Pickle Packers International Inc. in Wisconsin. It was over 8 feet long and weighed more than 1 ton! This giant pickle was made by filling a plastic casing with pickle juice and then putting it in a huge tank to ferment.
**And they say size doesn’t matter 😉
Okayyyy moving on from that great fun fact and terrible joke… It’s Job Board 🔦 time!
Job Board 🔦
We’re starting a section in The Pickle where we give job board updates and updates on cool stuff happening in our communiti’s ecosystem!
Sound cool right? I’ll let you be the judge for yourself:
Here’s what we have this week:
Eve ($47M Series A) - Legal AI assistant for plaintiff firms• Director of Product Marketing (Link)
Patlytics ($14M Series A) - GenAI patent intelligence platform• Head of Growth Marketing (Link)
Free Money 💰
Do you like free money?
Does the sign rise every morning?
Duh and duh, so check this out:
Knock2 $500 cash referral
Other Cool Events you Might Like
NYC Founders.& Friends Ski Trip on St Patty's Day
Join NYC's top founders for an exclusive St. Patrick's Day mountain takeover! On March 17th, the NYC Founders Club is buying out an entire Catskills ski resort for a day of unlimited runs, founder networking, and après-ski festivities. The day includes private NYC transport, all-day lift access (no lines!), and a curated gathering of 200 of the city's most ambitious high-growth founders.
Got something cool you want featured? Hit us up!
Skyler @ Optemization.com
John @ Knock2.ai
Stuck in a Pickle: Lessons & Stories from Early Stage GTM Leaders
How to succeed at an early stage startup 101
I have generated over $1 Million in revenue since joining Optemization. (So crazy tbh)
Here are the 5 biggest lessons I've learned as our 1 person Sales/GTM team.
You just simply have to hustle
Sorry not sorry hustle culture haters, this one is going to trigger you.
You want to make a difference at an early stage startup? Work harder.
There is no substitute or magic pill, gotta grind to reach your goals.
Sales is hard as fuck
There is no magic pill here either. Sales is hard.
It will feel like you're getting your teeth kicked in 90% of the time. Need to stay consistent, show up daily, and have extreme (borderline irrational) conviction.
Obsess over your customers
Your customers are the lifeblood of everything that you do.
But most people skip this part.
They close a deal and the client never hears from them again. That's unacceptable. Build a long term relationship and help to ensure mutual success.
Consistency leads to long term results
Example: I set daily/weekly activity metrics.
My goal every week is to:
Prospect 50 new accounts
Follow up with 50 accounts
Progress at least 2 deals to the next stage
Come up with one new big idea I want to test
Trust the process that daily consistency will lead to long term results.
Get creative / Relentless innovation
Here's the fun part about being at an early stage startup. You get to create!
My favorite framework when thinking about new ideas... think to myself:
"What would an average person do right now?"
And then do the exact opposite!
What does getting creative look like for me?
Few examples:
Create a Tech Pickleball community (oh hey 😉) to increase brand awareness
Build custom Notion pages (see example) for every prospect, tied together with videos + voice notes
Non stop innovative prospecting campaigns, lots of gifs and memes
I've learned a ton, but I still have SO much more to learn and grow.
Got questions about this? Want advice? Find me on LinkedIn or email me, skyler @ Optemizaton.com
NYC Tech Pickleball update
Theme of the week:
We are so freaking back baby!
Overheard quote of the week:
“I was depressed all winter without Tech Pickleball but now I’m back to being filled with happiness. I LOVE TECH PICKLEBALL”
Okay okay enough of me yapping… itssssss picture time woooo! 🎉
The smiles, the vibes, the people, the everything… all were sky high last week. (Just like every week!)
As always a genuine thank you to everyone who came out and made it special.
Excited to see everyone tomorrow!!
I will be rocking the pickle hat as always. If you want to chat, it will be borderline impossible not to be able to find me 😊
Andddd that’s a wrap!
We reallllly value your feedback and want to make this the best newsletter ever to support the community. Plz plz give us your most honest and blunt feedback on how we can improve it. We do this for you ❤️
Ps, know anyone who might be interesting in partnering with Tech Pickleball?? Hit up me, John or Tech Pickleball to discuss! We want to find more creative ways to expand and grow this community through awesome partners 🙂