Not Your Dad's Media

Good content builds credibility.
Outbound closes deals.
Not Your Dad's marries the two

Videos, the written word, memes, and more. 

Turn LinkedIn into your number 1 growth channel
notyourdadsmedia.com

Co-Founder, CEO

Founders You've Never Heard Of

Writing about the 99% of Founders NOT named Bezos, Elon, or Zuck

Founder

Pink's

Started a company. We're building the go-to maintenance arm for property management. Services include plumbing, electrical, handyman work, and of course… cleaning (move in/out mainly)

Hired a CEO so we can spend 100% of our time on Not Your Dad’s Media

Samsara

Learnings: If you can prospect and set demos/close deals ---> you can start a company

Account Executive

Cold called a lot

Was a pretty darn good BDR - won MVP and all that jazz. 

Taught me how to prospect into big accounts

Account Development Representative

The Browar Group 

Cold called till my face melted every day (200+ calls)

Spent 2 years doing it. 

Easily the hardest part of my infantile career

Multifamily/Apartments Broker 

Winston Goldman Distribution LLC

My first company. 

Bootstrapped it to 100k run rate 

Thought I was the fricking man 

Then it all burned down about 8 months later 😂

ADR @ Samsara (NYSE: IOT) // Startup enthusiast

49,341 meetings booked

That’s a lot of meetings 

And not that I’ve booked 49,341 meetings, but now that I have your attention… 

Here’s my journey in 568 words:

Started Pink’s 

Basically we started by working with Commercial and Residential Property Managers doing move out cleans for tenants, then moved on to other stuff like plumbing. 

Built some really cool systems to automate a lot of the outbound and other GTM activities which let me focus a lot on just making content and doing shit I enjoy 

Launched Not Your Dad’s Media with the mindset that content (video, written copy, infographics) is the only true language of the internet. And if brands don’t speak the language, you won’t make money from it. 

We’re fluent in this language 

Were building founder-led content engines to turn impressions and influence into real revenue 

If someone writes a note in the LinkedIn connection request, I rarely respond. 

Unless that message says something like:

“What’s up big papa”
“I love you”
“Omg bald ppl are my favorite”
“How’d you get so funny, smart, and gorg?”
“Can we be best friends?”
“Wow you and Adam Levine look so much alike”
“Jordan help me with LinkedIn, pwetty pweasee”


So if you send a connection request with a note… and it doesn’t include one of the above, don’t bother

Jordan Winston

CSU Grad

Constantly curious 

Passionate and Motivated Salesperson

Often can be found writing - either for "The Radical Moderate" or some other adventure

Fitness/Surfing enthusiast

Constant over-thinker

2x Newsletter editor

1x E-commerce founder

Currently building a Saas product in my downtime 

Co-Founder @ Not Your Dad’s Media // Helping Founders & Execs win on LinkedIn

You’re allowed to be:

- Richer than me
- Younger than me 
- More successful than me
- better looking with more muscle than me

But you’re NOT allowed to be:

Younger AND more successful than me

It’s just simply not gonna fly.

My friends and I met up last Saturday at 12pm for a sandwich and a beer.

Once we all met up, we promised to turn off our phones until sundown. 

Welp that didn't happen. 

Cause once sundown came, most everyone forgot and left their phones off till about 9pm. 

Highly recommend this. 

The Jews figured this out a few thousand years ago... and named it "Shabbat"

My friends might be late to the party, but hey, we made it. 

Disconnect every once in a while… it won’t kill ya🤷‍♂️

IRL events just took a HUGE W last night

Couldn’t be more grateful for everyone that came out last night for the first annual Not Your Dad's Media holiday party last night

I’ll take any excuse to drink Guinness with other founders…

But last night taught me 4 things 

1) NYC is the best city ever

2) Founders and builders are my favorite kinds of people in the world 

3) Taylor looks better in my sweater than I do

4) Content, engagement, and in person events are going to continue to be a major focus for most companies. 

It’s my thinking that if you nail content and IRL events, it’s going to be REALLY hard to lose as a B2B founder in 2026

Again, to all those who came, I appreciate you❤️

-jordan

Had this Taxi driver in Barbados that absolutely blew my socks off...

Meet Cory. 

Cory is a 45 year old Barbadian Entrepreneur. 

No, Cory didn't build a B2B SaaS tool. 

And no, he isn't building a sales coaching agency

Cory scraped together cash when he was 24 to buy his first car. 

He used that car to start taking tourists around, saving his shekels and putting money aside for a few years. 

2 years later, Cory bought his second car. 

He hired his best friend Eldred to drive that car. 

He tells Eldred he can keep 75% of the earnings, and he has to pay the lease on it. 

Cory immediately starts making a few extra hundred dollars a month doing this. 

Fast forward to today, and the guy has 15 cars, has his family and friends working with him, has contracts with every major resort in Barbados, and is building 3 AirBnB's right on the beach. 

Fckn legend. 

I'd bet the guy is taking home $500k ish per year 

These kind of entrepreneur stories reallyyyyyy get my juices flowin. 

Just a testament to the fact that there are a million and one ways to make this whole business thing work. 

Cory, you're a legend. Keep hustling.

ps this is not a photo of Cory lol

I'm in Barbados right now

...and it's fricking disgusting. 

Everyone here is laughing, has a really cool accent that I thought was Jamaican at first, and is actually enjoying life. 

It's gross. 

Not once have I heard people talking about:

- Increasing shareholder value
- hopping on a quick call to explore synergies 
- leveraging core competencies to operationalize value creation

Where in the f*ck am I...

Get me back to New York, please and thanks.

On the first night of Hanukkah in Sydney, AUS, 15 Jews were gunned down by a terrorist. 

Crazy part, is when I heard the news, my reaction was:

"yup, sounds about right."

Which is crazy, because it's not even surprising anymore. 

It seems to just be part of everyday life - Jews being murdered for being Jews. 

I rarely make posts like this, but antisemitism is a tale old as time, and one that keeps rearing its ugly head in every part of the world. 

It's made me nervous to wrap tefillin in public 

Or go to synagogue without worrying about a terrorist breaking in and gunning people down. 

It used to be a semi-irrational worry, but now it's very real. 

And it's happening all over the world. 

Just know - killing Jews in the diaspora is not "freeing" anybody. 

It’s terrorism in its most grotesque form.

For ever and always, AM YISRAEL CHAI 💙  and keep wearing your Magen David's loud and proud

LinkedIn, very serious question:

Which ways correct?

“If nobody comes to our holiday party, I’ll die”

- Taylor

So if you don’t want Taylor to die...

you should swing by the first annual Not Your Dad's Media holiday party TONIGHT

details:

- 6pm in Greenwich Village
- There will probably be Karaoke
- There will be Pizza and a $1,000+ worth of booze that needs to be consumed 

Further details will be provided…

Linkys in comments

I’m thankful for:

My mom
My friends 
My new backpack I just bought
The show Pluribus 
Antibiotics and modern medicine
My gym
The ability to make magic internet dollars
The city of New York
Dive bars
Being Jewish 
Mediterranean food
My First Million podcast
My clients who I’d move heaven and earth for 
Air conditioning
The ocean
Psychedelic mushrooms

And last but not least….

LinkedIn and the lovely ppl I’ve had the opportunity to meet on this (sometimes god-forsaken) platform. 

Tag someone you’ve met on here ⬇️

Taylor Skyler Aidan Gavin Kimberly Dom Carson Jason and about 15 more that I didn’t mention 

Happy thanksgiving fwends:)

Talk all the sh*t you want about LinkedIn...

But it's allowed me to meet some of the most badass people building companies in New York City 

One of those founders is Kimberly Green aka the cofounder of Sam's List

What's Sam's List you ask?

Well, if you've ever listened to the My First Million podcast, you've prob heard Sam talking about it 

It's THE marketplace you go to in order to find accountants, bookkeepers, CFA's and fractional CFO's

And Kimi was nice enough to talk to me about it for the Founders You've Never Heard Of newsletter

couple notes about her and the journey to building a $100M marketplace

- She was one of the only people in her hometown to leave Texas 
- Grew up in a town that didn't have a single stop light. Small town TX type shi
- D1 Athlete - played basketball at Baylor. Hence the competitive nature
- Horrible handyman - we assembled a dresser together. She didn't help much lmao
- Has two pretty cool co-founders Sam Parr and Joe Speiser
- Belivers entrepreneurship is risky no matter what - so may as well choose the risk that has a real payoff, not the risk of staying stuck
- Had a business called "Kimi sucks" in college, where she'd go vacuum peoples dorm rooms for 25 cents. 

Kimi is a legend and has golden retriever type energy

Which happens to be my fav type of energy

Check out the full scoop on her in the Founders You've Never Heard Of newsletter which'll drop tomorrow. 

Linky in bio

CEO’s and execs in NYC listen the fck up:

I'm throwing a Founder's game night right here in New York. 

Here's what I'm thinkin:

- We'll have games (LCR and Blackjack)
- There will be room for 12 other B2B founders 
- We'll have the most above-average cocktails you've ever had

If you don't wear an ugly holiday sweater, you're not allowed in.

Dear agencies,

Give your clients the opportunity to pay you upfront for 3-6 months at a discount.

Sounds trivial, but now at Not Your Dad's Media, we do pricing like this:

Month 1: No contract. We have no idea if we're going to be a good working fit, so doing a contract upfront could produce a lot of pain for both parties.

Month 2: If things go well, give client option to pay for 3 months up front at a discounted rate. 

Not required, but some companies choose this.

Why you should offer upfront pricing for a discount:

- Helps you with cashflow 
- Lowers admin + collection headaches
- It shows you're committed to each other 
- Clients love a deal they can justify internally 
- With year end coming, it could help them with taxes

+ a myriad of other reasons. 

I'm such a business novice that this blew my mind when we started doing it 😂 

Pretty please share some more business lessons you've learned in the comments ⬇️

Who wants to get their sh*t rocked by Chelsea Olsen and I?

Mr. Pickles will also be in attendance (if you ask nicely)

If you know me, you know I love a good post-roast. 

Having the ability to make fun of strangers in a loving, yet constructive way is right up my alley.

So when Chelsea asked me if I wanted to co-host with her, you know I jumped on the opportunity. 

So.... on December 18th at 1pm ET, we'll be breaking you down mentally and emotionally to see what's going on with your content.

We will be:

- Reviewing a few posts
- Roasting them (sometimes lovingly)
- Showing you how they could've been written better

Coolest part is that it's completely free 

Plus I'll be wearing my ugly Christmas sweater. 

So come learn how to create content that brings in engagement, inbound leads, and real sales opportunities.

If you wanna come hang and learn a thing or two, register here: https://luma.com/2xstcuwc

Don't bother hiring a writing team...

If you're not also doing these 3 things:

1) Commenting on ICP posts daily
2) Responding to comments on your posts
3) Continually adding connections in your ICP

I can't say this enough...

but if you have 1000 followers, and you hire a ghostwriter to post on your behalf, and you're not doing these 3 things...

You're quite literally pissing money down the drain. 

You're posting into the ether and not adding much value to the platform. 

LinkedIn really is "pay to play" and if you spend the time adding 20 high-value, well thought out comments, the algo will reward you for it. 

If you don't, it doesn't matter how good your content is... nobody will see it. 

Shitty part? This takes time to do, and there's no shortcut or way around it. 

Hence why Not Your Dad's Media's exists. 

p.s. this is a photo the morning after our holiday party. Safe to say Taylor needs a nap

Jensen Huang confirms that Nvidia is the once there of they did that of last. 
making them the first company ever to that they did internet that of them it before. 

You did it, Jensen. Congrats.

America is seriously optimizing for the wrong things

Ever since I can remember, the state of America has been really weird. 

- Buttoned up politicians that are stuffier than my 5th floor NYC apartment. 
- Business leaders who did their very best to hide in the shadows
- Actors and actresses losing all sense of humanity bc of endless media training

America has been wrought with phoniness and bullshit forever. 

"So Jordan, you seem to have America figured out... what DO the people want?"

Authenticity. Without a doubt. 

Authenticity is something you can't fake. It's innately human to know when someone is being fake or not. 

It's the reason that figures like Mamdani and Trump were elected. 

Say what you will about them, but if anything, they're perceived as 100% authentically who they are. 

Politicians know that the next elections won't be won on CBS or Fox. 

They'll be won on 

- Joe Rogan
- X
- TikTok
- Dare I say, LinkedIn?

This was proven in 2024. 

And proven again when Mamdani one in 2025. 

Which is why I will do everything in my power to ghostwrite X and LinkedIn content for a politician in the upcoming elections. 

Might be way too big of an ask... but if you're connected with anyone running for elected office (on the national level), hit me up. 

You'll have $4,000 in your account if you do 👀 

#memesforpresident2028

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