This is the week you’ve been waiting for. Tech week in NYC is here.

And what’s even more here — The collab of the century is here!

Special Tech week edition, Tech Pickleball x Apollo let’s do it!

To sign up this week, you have to go through this link: (do it now before you forget)

https://partiful.com/e/L7DM3gA500xzhGxQKoNH

We’ll be raffling off these sweet paddles (pickles not included) so it may just be your lucky week.

Random note, the other day on the subway I kept thinking to myself….

”I have so many people I want to talk to during tech week and after tech week, but what will I ever possibly do if I don’t have their contact info???”

Answer: Apollo.io!

Why play a guessing game when you could have unlimited contact data ready to go for prospecting? Outbound is already a beast, so there's no need to wrestle it while blindfolded.

You wouldn’t play pickleball blindfolded. (or at least probably idk) So don’t prospect blindfolded!

Apollo.io has you covered.
**Pssssst thank me later 😉

Can’t wait to see you all tomorrow!

Get there early before the bagels and coffee run out. It’s tech week so we’re expecting a huge turnout!

Now to the fun stuff!

🥒 Pickle fun fact of the week:

There’s a Spicy Pickle Festival

Yes, spicy pickle festivals exist—and they’re as bold as you'd hope. While general pickle festivals like Picklesburgh in Pittsburgh draw huge crowds, several smaller events across the U.S. now focus specifically on heat-packed pickles.

Expect spicy pickle-eating contests, ghost pepper-infused recipes, and creative takes like chipotle-dill or sriracha-garlic pickles. You’ll also find spicy fried pickles, hot pickle cotton candy, and Bloody Mary bars loaded with fiery garnishes.

These festivals often feature small-batch pickle makers, hot sauce vendors, and plenty of offbeat merch—like “Hot & Briny” t-shirts or flaming pickle stickers. It’s a spicy celebration for heat lovers and brine fanatics alike.

**Did someone say Tech pickleball offsite??? 👀

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

A no now isn’t a no forever

I once closed a deal with a prospect that said no to us 12 months ago.

Here's how I did it:

Consistent. Relevant. Friendly. Useful. Value. Touches.

When it's clear that the timing isn't right for an opportunity, I ask them:

"Now that I understand your situation, would you be okay with me sending over the occasionally relevant Notion update?"

Assuming they say yes (and they will), that is exactly what I then do.

Notice how none of these emails say,

"Just checking in"

"Hope you've been well"

"Wanted to bump this up"

GARBAGE ^^^

I use frictionless no CTA value touches with relevant updates.

The framework I use in my head is....

Take me (Skyler) and any sales thoughts out of the situation, if they opened this email, would they get value out of it? Would it be useful for them?

If yes, fire away baby.

If no, go back to the drawing board or don't send anything at all.

If something changes on their end, who do you think they're going to think of...

The guy who sends over useful frictionless value touches every month?

Or the pestering salesperson desperate for deal updates?

Just cause it's a no now, doesn't mean it's a no forever :)

TLDR, Be more useful and send things that are actually helpful to your prospects instead of cringy "just checking in" nonsense like everyone else.

Ps, if anyone wants any of these Notion blog posts/use cases highlighted below, LMK and I'll send them your way 🤠 promise there will be zero CTA

reach out to me at skyler @ optemization.com or hit me up on LinkedIn, or shoot just cold call/text/facetime me, 5038807397

NYC Tech Pickleball update

Theme of the week:

Bring me sunshine so I can experience peak pickleball weather again.

Overheard quote of the week:

“Tech Pickleball is like sunshine on a rainy day”

Excited to see everyone tomorrow!!

Oh wait, can’t forget picture time with our favorite 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 🙂