The Pickle: Volume 20

Did you miss The Pickle? Wait no further!

AuthorAuthor

Skyler Birk-Stachon & John DiLoreto
March 13, 2025

I love this shit. Simply love it.

Pickles, vibes, smiles, new connections, light exercise, and community building.

What could be better than that?

Spoiler alert: Obviously nothing!

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 Faces, New Faces, Infinite Smiles… and the best way to start your Friday morning:

SIGN UP NOW BEFORE YOUR PICKLES GO BAD:

https://lu.ma/3ur8k784

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:

In the Pacific Islands, natives pickle their foods in holes in the ground lined with banana leaves, and use them as food reserves in case of storms. The pickles are so valuable that they've become part of the courting process, helping a man prove he'll be able to provide for a woman. In Fiji, guys can't get a girl without first showing her parents his pickle pits.

**Disclaimer, I’ve never shown a girl my pickle pits… is that my issue??? 🫨

Side note, has anyone ever lived in Fiji and can they confirm/deny if this is true or not? Plz hit us up immediately if you can.

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 communities ecosystem!

Sound cool right? I’ll let you be the judge for yourself:

Here’s what we have this week:

Senior Business Development Representative (Rutter)

Enterprise Sales Leader (Notion)

Director of Revenue Ops (Gloss Genius)

https://app.welcometothejungle.com/jobs/Bt3K4ePy

Head of Sales (Shaped)

Got something cool you want featured or a job you want posted? Hit us up!

John @ Knock2.ai

Stuck in a Pickle: Lessons & Stories from Early Stage GTM Leaders

How I generate 2+ inbounds a week from LinkedIn content

I have generated over 750k impressions in the last 365 days posting daily on LinkedIn.

Here's my exact content strategy: (you can steal it)

#1 Edutainment

Notion / no code automation content that is educational and entertaining

↳ I am trying to provide as much value as possible with every post

↳ You can find Notion content anywhere so I need to add a twist

↳ That twist is where the entertainment piece comes in, has to be unique

#2 Give away the process, sell the implementation

I tell you exactly how we build at Optemization and what we do for our clients

This does a few things...

2a) If you watch one of my demos or read my posts you could:

→ Copy the exact process and use it for yourself (some will, most won't)

→ Try it on your own, realize how hard it is and then give up / hit me up

→ Say "wow that's cool I want that!" and hit me up

Give away the process for free, sell the implementation

"If the things you give away for free are better than what your competitors charge for, people will automatically assume you have the best solution"

Stolen straight out of the Alex Hormozi playbook and wow does it hit like crack

2b) Increases trust

You already know what we do and you've already seen my face so...

→ If you're interested, we just need to sort out the remaining logistics

  • like price, timeline, scope etc

→ Leads to much better (and more fun) conversations than cold outreach

I smile a lot and am sometimes funny so maybe that helps? Idk

#3 Be authentically and unapologetically Skyler

This is by far my favorite part.

I'm literally just being me, always have been, always will be :)

When I'm not talking about Notion / automation, I'm talking about:

↳ Tech Pickleball (oh hey 😉)

↳ The game show I created (Sell me this SaaS)

↳ The highs and lows in the life of a 1 man sales team figuring it out on the fly

↳ All the crazy experiments I try (that usually fail miserably)

↳ Travel pics and updates on all the wild stuff I do

↳ And of course cat pics

And hey, some people like it and it's really fun

Hope this was a helpful breakdown!

I've been generating ~2 inbounds a week lately so clearly somethings working.

Got questions about this? Want advice? Find me on LinkedIn or email me, skyler @ Optemizaton.com

NYC Tech Pickleball update

Theme of the week:

Smiles 😊

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”

Yes, I did use the same quote this week cause I liked it so much last week.

And no, I won’t apologize for it.

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 on Friday!!

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 🙂