Hello friend,
Why you're getting this: this is my Friends Newsletter, a brain dump of interesting things that I send to interesting people I've met and friends I want to stay in touch with. Zero pressure to stick around—just click unsubscribe if you don't want to get it (don't worry, I won't be notified).
✈️ Travel Advisory: I'll be in Palm Springs next week. If anyone is around and wants to get a coffee, email me!
He told me I was in the Epstein files.
My stomach dropped. For what? How? I didn't even know Epstein!!!!!!!!!!
Heart pounding, I clicked the link.
It turns out that Epstein had received a Twitter notification with a roundup of popular tweets.
Mine happened to be one of them.
Link to the document 😂 (Something tells me this email will have my highest open rate ever—I'm sorry, I'm a troll.)
In my last newsletter, I wrote about divorce.
Many readers emailed me, telling me they felt some of these feelings but weren't ready to separate from their partner. That they wanted to fight—to work through their differences.
I might have something that could help your relationship… (or maybe help you work through an existential crisis—or trigger a new one)
Last month, Zoe and I sat in our den with our jaws on the floor.
We were in front of my laptop, taking turns reading a report out loud, line by line.
The document read like a CIA dossier—incisively breaking down each of our repeated fights and nailing our relationship dynamics.
We had to laugh. We couldn't believe it.
A few days earlier, I'd asked ChatGPT a simple but loaded question:
"What information would you need in order to become the ultimate personalized relationship coach?"
It replied with a long list of personality tests—the same ones psychologists use to evaluate mental health, personality, and relationship satisfaction, and a ton more.
The tests were all available online, but scattered across annoying PDFs and awkward, old-school forms. For someone with ADHD, like me, the idea of doing them one by one was pure torture.
I just wanted to pound through them as one big test.
So I asked Claude Code to build a simple app that combined them.
I'd done some vibe coding last year with tools like Replit and Lovable, but nothing prepared me for how good Claude Code has become.
Within a few hours, I had a beautiful web app that combined all of these tests into one.
When I say beautiful, I mean it looked like I employed a $50,000-a-month payroll of talented designers and engineers who'd spent two months working on it.
Except I didn't have a $50,000-a-month payroll.
I'd paid Claude around $500 in AI credits — and what would normally take months had taken hours.
Crazier yet, I'd just talked to it like it was a human employee.
Once a beta version was ready, Zoe and I completed our tests and exported our results into ChatGPT—no names, no context—and asked:
"Based on this couple's psychological test results, tell me as much as you can about their relationship."
That's how we ended up in our kitchen, in shock, as ChatGPT broke down our relationship patterns with eerie precision.
It felt like a report written by a world-class therapist who'd spent dozens of multi-hour sessions carefully dissecting our dynamic and suggesting remedies.
It told us where we were most compatible, and where we'd struggle if we didn't put in the work.
It even wrote personal deep dives on each of us, our personalities, and our individual gifts and challenges.
And it knew all of this from 45 minutes of multiple-choice questions.
I started thinking about friends who'd never been to therapy, or couldn't afford anything like this, and how much it could help them.
That's when I realized this was a business.
Something that would solve a valuable problem for a lot of people.
So I got to work.
For the last month, I've been jolting out of bed at 5:30 a.m., too excited to sleep, obsessively building this product.
And today, I'm excited to launch Deep Personality.
I think it's one of the most comprehensive mental-health screening tools on the internet.
It's not a replacement for professional help, but a roadmap to it.
Most people stumble blindly into a random therapist or doctor's office without knowing what type of treatment they are even trained in or its efficacy for their specific problems.
Deep Personality will screen you across 30+ mental health conditions and provide you with a detailed roadmap of how to get the help you need.
In under an hour, it gives you a high-signal snapshot of your mental health across dozens of dimensions:
You can do this individually, or compare yourself to anyone in your life.
This is where it gets really interesting...
Have your partner, coworker, friend, or family member take the assessment, upload their profile, and wait while the app analyzes your personalities and how they interact with one another.
For Zoe and me, having our relationship laid out with this kind of clarity — patterns we'd felt but never articulated—was deeply meaningful.
Once you complete the assessment, you get a 50+ page deep dive on your personality.
It felt like finally getting the owner's manual for myself.
You also get a custom AI prompt pre-loaded with your psychological data.
Drop it into ChatGPT, Claude, or any AI assistant — and you have a therapist who already knows your attachment style, anxiety patterns, values, trauma history, and emotional regulation tendencies.
No more spending six therapy sessions explaining who you are.
The AI already gets it.
And if you're in therapy, or going to start with a new therapist, you can also export a clinical PDF designed for practitioners—raw scores, thresholds, severity flags, discussion points, and citations.
Or… it can help you attract your perfect romantic partner.
This one's just fun.
Deep Personality can generate dating bios based on your actual personality data — tailored to Hinge, Bumble, or Tinder — in tones like witty, sincere, adventurous, or intellectual.
The AI turns what makes you unique into something that attracts compatible people.
Once it knows you, it helps you get the help you need. Based on your results, it recommends books, podcasts, and treatment options backed by peer-reviewed research.
The full assessment covers 30+ psychological screens and 300+ questions, and it costs a fraction of a single therapy session (free for the basic analysis, $19 for the full report, $29 for a couples comparison).
It's really crazy. I think it's going to blow your mind.
Who is this for?
I'd love it if you'd try it and send me your thoughts!
👉 Click here to check it out: https://deeppersonality.app
Warren Buffett has a great line. He asks college students in his lectures:
"If I granted you the right to buy 10% of one of your classmate's earnings for the rest of their lifetime, who would you invest in?"
Well, I stole his excellent question and I've gotten in the habit of asking it.
Last summer, I spoke to a class of business school students at the University of Victoria.
It was an unpaid speech, but it turns out they paid me.
Why? Because I ended up starting a social media agency called download with two of them, Aiden and Hiroko.
It's worked out really well. It's growing like crazy, and already kicking off profits. (If you need video-based social like TikTok or Instagram Reels, email them.)
As I always do, I asked them the Buffett question.
The name that came back, with zero hesitation, was Connor Pettepiece.
I met Connor and he had an earnest intensity. I immediately liked him.
He told me he was interested in buying a business, so I told him I'd be interested in backing him.
A few months later, he'd found a business he wanted to buy with his business partner, Attila Knaitner.
It was a perfect first acquisition. Unsexy. Under optimized. And in an AI resistant industry. Most importantly: he could acquire it at a fair price.
The business was Rocky Mountain Concrete in Lumby, British Columbia.
We closed the deal a couple months ago, and I'm now a proud co-owner of a concrete business. There's a sentence I never thought I'd write.
Connor and Attila have really impressed me.
They've rolled up their sleeves (including back breaking manual labour to learn the ropes) and completely systematized and transformed the business.
They've been sharing their progress on Instagram and it's been fun to follow along.
So, if you're looking for precast architectural concrete or landscape products for a home renovation, a real estate development, or a bizarre concrete art project (?)—you know who to talk to. Email Connor
Last week I went on my friend Dan Shipper's podcast and we nerded out for an hour about how we're both using AI.
It's pretty shocking how good these tools are. I doubt anyone will be writing code (manually) within the next 3-5 years.
We talked about:
Listen here: YouTube / Spotify / Apple Podcasts
You're lucky.
All my life, I couldn't. Ever. Not even a tiny one.
The pressure would just build and build, sometimes coming out as weird gurgling noises.
It was horrible.
For years, doctors dismissed me:
"You must be burping and just not realize it."
Ultimately, after a decade of frustration and brutal acid reflux, I finally cracked it.
It turned out that I had a rare condition called Retrograde Cricopharyngeal Dysfunction (the inability to burp).
I found a small group on Reddit of fellow NoBurpers (/r/noburp) and learned there was a highly effective treatment.
An endoscopic Botox injection into the throat.
I had to fly to Chicago to get it, but the effect was life changing.
Now, 5 years later, I can still let 'em rip.
No more pressure. No more gurgles. No more acid reflux.
I've met a few others with the same affliction, and we always hug as brothers and sisters. It's a bizarrely awful shared experience.
So, I wanted to send up a flare and write this here. If you can't burp: there's hope.
The doctor who helped me is Dr. Robert Bastian. He did my procedure in Chicago.
He's amazing, and if money is a problem, he can also do a cheaper procedure in his office without using the endoscope (which requires sedation and a hospital procedure).
There are also a few Canadian docs who know about this, but most will dismiss you completely. Best to find doctors listed on the subreddit.
Godspeed, my friends 🥲
That's all for now…
-Andrew
Want to read more? Here are a few of my best past issues:
Did you enjoy this newsletter? Say thanks by checking out one of my businesses:
Follow me on X: @awilkinson
Follow me on Instagram: @awilkinson
