Thighs, Taxes & Tech

Trust Fun is brought to you by Postscript

Let’s talk about texting. Not the “u up?” kind—the other kind. The one where your most loyal customers literally ask you to text them, and then when they do, you ghost them with a “please email us.”

Brutal. We’ve all been chasing “personalization” in marketing for years, but here’s the truth: most of it’s just glorified mail merge. Postscript is flipping the script. Launching April 16th, Shopper is the first AI shopping assistant built to actually hold real conversations over SMS at scale.

Not robotic trees, not outsourced agents with a different tone every Tuesday—just fast, helpful, on-brand replies that convert. It’s like finally having a team that texts back. One that knows your customer, understands what they’re looking for, and points them straight to checkout. I've seen it in action—this thing gets it.

If SMS is your best-performing channel (it is), and your replies are currently going into the void (they are), Shopper might be the game-changer.

Check it out and register EARLY here:

This week, while reviewing a video of a man ripping a pair of jeans clean off his body to demonstrate stretch, I had a moment. A real "what even is my job?" moment.

Like, technically, I’m the founder of a men's clothing brand. But practically? I’m… reacting to slow-mo footage of pants exploding off a guy’s legs and adding time-stamped comments like “can we get more thigh meat in frame?”

Some days it feels like I run a creative agency. Other days it’s a logistics company. Sometimes it’s customer support, and other times I’m just yelling at spreadsheets. I once spent six hours trying to figure out how to make an email pixel fire correctly on a Nordstrom order. I don’t barely even know what that sentence means, and I wrote it.

Welcome to work in 2025.

We are in a categoric shift. Ten years ago, if you said you wanted to be a social media manager, people would’ve laughed. Now? I know 26-year-olds with six-figure salaries and brand-side access to the inner workings of the internet. They are killing it.

Same goes for creators. When I was in college, “full-time creator” wasn’t a thing. Now I know UGC creators making more money than senior engineers. And yeah, sure—AI might be coming for them too. I went semi-viral last week for a tweet showing how ChatGPT can basically replace white studio photography with a prompt and a dream.

Like… the outputs are scary good. I'm not saying we're replacing models yet, but let's just say the AI thighs are looking toned.

It’s exciting and weird and scary and amazing. Startups give you a front-row seat to the way work is changing in real time. One day your most valuable employee might be your motion designer, the next it’s your retention marketer, and the next it’s a random 72 year old model you hire on Craigslist to be “Uncle Don” at a shoot.

Yes, this is Don. He rules.

And somehow, through all this chaos, the IRS still expects me to “categorize” these expenses neatly for tax season. Like yes, totally, “ripped pants content” goes under Professional Services??

Anyway, if your job feels made-up—it probably is. But that doesn’t make it any less real. The market is shifting. Adaptation is the whole game now.