Tech Founder to Cool Guy Era

Alexa, play “Rise and Shine” by Kylie Jenner ☀️

Welcome to your new happy place. Mid-week slump? Don’t worry, your Hump Day 🐪 is about to hit different.

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Words are just complicated airflow — so watch the summary here. 👀 

After reading this, you’ll be able to girlsplain the Bezos glow-up, the best tech founder pop-culture moments, how to dress "tech”, and maybe even score a date. (~read time: 6 min)

Is this “girlboss” in the room with us right now? Not today. We’re talking about The Tech Bro, so get excited because we’ll be getting into:

• The Bezos Blueprint

• Tech Bros in The Wild

• How to Dress Like Stealth Wealth

• From Your Inbox to IRL: We’re Playing Matchmaker

• Are You a Founder in Your Pre-Billionaire Era?

And when you have your inevitable ~mic drop~ moment at the water cooler, share this with your besties so they can too 💌 (& let us know on social).

From nerd to athlete bod, Silicon Valley to Hollywood, the tech bro glow-up is evolving. But what triggers this natural progression? Is it founding a company or finding a partner? Let’s investigate.

The Bezos Blueprint

This Glow Up Will Be Studied in History Books 🛥️ 

The founders of Silicon Valley might’ve had money, but they were never cool. That is, until now. And we can thank Jeff Bezos for breaking that mold. 👏 

Jeff Bezos (Founder of Amazon) started caring about his looks and changed his entire lifestyle. Not only is he showing up at Coachella, hanging out front-row at fashion shows with Anna Wintour, but he’s even going shirtless on super yachts. (Is this upgrade available on Prime Day??).

Let’s ⚠️be real⚠️ how many times have you seen Bill Gates hang around shirtless on a yacht? He might be on yachts, but he’s too lowkey and sensible to be making those kinds of headlines.

So what’s the difference in this equation? It’s the same person who has enough pull to get her statue on a $500M super yacht. It’s giving second-wife energy. Now I’m not saying all of this has to do with Lauren Sanchez but…it wasn’t until their relationship that he’s suddenly cool guy Bezos. And now they’re engaged with the largest prenup ever for his $140B fortune.

Tech Bros in the Wild

The Billionaire Boys Club and Their Best W’s 📸 

Tech founders can be cool too. Wow, they’re just like us! The tech bros are leaving Silicon Valley and setting their sights on… Hollywood.

Here’s a roundup of their coolest moments:

Mark Zuckerberg (Founder of Meta) at The Eras Tour. Yes, you heard that right. Zuck got to hear Right Where You Left Me as a surprise song and I didn’t. BTW he was the ONLY person richer than Taylor Swift in that entire stadium. Queen 👑.

Evan Speigel (Founder of Snapchat) pulled Victoria's Secret Super Model and Orlando Bloom’s ex, Miranda Kerr (oh and they’re married).

Jack Dorsey (Founder of Twitter) is hanging out on yachts with The Carters. Not just Beyonce and Jay Z, but Grammy Winner Blue Ivy too.

Elon Musk (Founder of Tesla) has been to the Met Gala TWICE. And that’s the fit he’s rocking??

And Alexis Ohanian (Founder of Reddit) managed to marry the GOAT 🎾.

Yep, they scored. And we’re not even talking about them getting their bags 💰️.

It’s Giving “Tech”

How to Dress Like Stealth Wealth 🧢 

Silicon Valley’s status symbols of herd mentality are changing. They used to be sleeping on mattresses in empty apartments or owning 10 variations of the same shirt paired with a zip-up vest. But now they’re leveling up. And it’s all part of their cool-ification journey.

If tech founders want to fit in with the Hollywood elite, they need to make major fashion-forward changes. They’re no longer struggling with startups on the brink of death so it’s time to look like it.

Jeff Bezos is the prime example (lol). Back when he was a struggling founder building a software startup, his uniform consisted of khakis and blue T’s. But now that he’s a billionaire growing a media empire? He’s rocking aviators and tight Bruno Cucinelli T’s.

The vibes are still comfort and minimalism, but the basics are Brunello Cucinelli Sweatshirts, Moncler Vests, and Lanvin Sneakers. And that’s how you do Succession level Stealth Wealth.

But it’s not just style, it’s mind and body glow-ups too. We’re in the age of Oura Rings, Ice Baths, Athletic Greens, and Equinox. It’s giving summer camp for billionaires.

There’s so much innovation when it comes to building new products — but their style individuality remains bleak.

What’s better than glowing up alone? Finding a partner who can elevate you. The Serena to your Alexis, Miranda to your Evan, Lauren to your Jeff. And we might’ve just found her for you.

Inbox to IRL

⚠️it's time to girlsplain matchmaking⚠️

So you're a founder but you still haven't found her? Your deal flow is hot but not your date flow? You're focusing on the wrong M&A when you should be focusing on a marriage and acquisition? Forget the B2B SaaS, you need Bae2Bae Sima aunty as a Service.

We've all been there - forget re-engaging, it's time to churn the cold leads and start relation(ship)ping.

Calling all ebita-daddies and millionaire-mommys:

We're here to help you find your unicorn (in love). And this just might be it ↓

Here’s the tea ☕️

Things I love:

Coffee (specifically: americano misto with almond milk, extra hot) and a good book. Sports and being active (specifically: soccer, beach volleyball, barrys, yoga, running). Sarcasm that treads a bit too close to bullying, but well intentioned of course. Music and going to concerts. Cooking (hoping you don't cook so you can do the dishes)

Things I don't like:

Hiking (I'm sorry I don't get it, it's literally just walking but extra tiring). Drinking. Humble bragging (if you're gonna brag, just brag). Not sharing food at dinner. "I don't know", "whatever you want", "doesn't matter" attitude.

Right now I'm: living in NYC and working on my startup (pre product/ stealth/ consumer)

Rizz Check ❤️‍🔥

Her Green Flags ✅

💚 busy most of the time, don't need texts 24/7, happy to support you doing you <3

💚 likes spontaneous things, down to try things and experiences I've never done before

Her Warning Label 🚩

❤️ will choose my startup over you if it came down to it

Interested? Slide into her DMs.

Skip the Blue Bottle, Find a Date — want to be featured next? Apply here. 

Are You a Founder in Your Pre-Billionaire Era?

Attend Carry’s Personal Finance 101 For Startup Founders

Carry is helping you build generational wealth through their Solo 401k and Carry IRAs — including a personalized financial plan and access to financial advisors.

They're hosting a free personal finance 101 workshop for startup founders, sign up here to save your spot and get the replay.

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