|
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).
Here’s what I’m thinking about…
-
People think business is math.
Numbers. Spreadsheets and P&Ls.
But that’s only 10% of it. While the numbers are critical to get right, I think the other 90% is far more important.
To be great at business, you have to do two things:
1. Prevent your brain from tricking you into doing stupid things
2. Figure out how to read and motivate (and sometimes avoid) other people
In 1995, Charlie Munger, Warren Buffett’s longtime business partner, gave an incredible speech about why humans do stupid things.
In it, he breaks down all the key psychological effects that warp our thinking and cause bizarre behavior.
In 2014, I made it my mission to memorize this talk. I listened to it every single day on my drive to work and tattoo’d it into my brain.
It has been one of the most durable and important pieces of content I’ve ever consumed, and a few years ago, Chris and I decided to make it more accessible.
We took the original hour long scratchy audio recording and turned it into a shorter and more accessible animated video.
I’d encourage you to listen to the full version (over, and over, and over again), but I wanted to share our animated version as a little primer.
A few of my favorite quotes from the talk:
“Never, ever, think about something else when you should be thinking about the power of incentives.”
“The human mind is a lot like the human egg. When one sperm gets in, it shuts down so the next one can’t get in.”
“It’s not greed that drives the world, but envy.”
“What a wise man does at the beginning, a fool does at the end.”
-
Do you know someone like this:
- Rich
- Owns a business
- Burned Out AND/OR Getting older/wants to retire
Tiny wants to buy more businesses, and we need your help to find them.
We’ve found that the best opportunities often come from simply asking around.
So here I am, requesting your help. If you enjoy this newsletter even a little bit, I’d ask that you take the next 30 seconds to think about it.
Okay, did you do it?
I'll wait...
Ok, did you do it? Perfect, thank you. Let me know if you think of anyone we should talk to.
- A few weeks ago, I went on My First Million, my favorite podcast, and talked about how I, for one, welcome our new AI overlords. I talked about a ton of stuff, including how I’m using AI agents, an interesting public company I invested in, and much more.
Fun episode. Listen here: YouTube / Spotify
-
I decided I'm going to brag more.
Not about myself. But about my friends.
Today I’m going to brag about my pal Allegra Poschmann.
You’ve probably never heard of her, but if you’re a woman, I guarantee you know her work.
Glossier. Hill House. Reformation. The Honest Company.
In 2009, she was a broke designer. Today, her company, Pact is the secret sauce behind-the-scenes on some of the biggest success stories in retail. Like Metalab, but for ecommerce companies.
Usually, someone with such absurdly good taste comes at a cost. You hire the designer who makes the world’s most beautiful website and brand but… it doesn’t convert. They don’t think about the business side.
Allegra is a rare talent who has the trifecta: astounding design skills, a deep understanding of what actually drives revenue, and the ability to sell and convince complex groups of people she is right.
Here's a few stories she recently told me over lunch:
- She just helped Rifle Paper Co. increase conversions by 150%
- Her strategy drove 1800% revenue growth for Hill House, launching their famous Nap Dress (men: apparently this is a big deal?)
- Her work with the piercing studio, Studs has helped take them from a handful of locations to 40+ studios nation-wide
Allegra is humble. She’d never say all this, but I feel compelled to brag on her behalf. More people should know her name.
Check out her work and, if you’re selling things: software, t-shirts or your time, you should hire her.
-
"Your working memory is in the twentieth percentile," the neurologist told me, studying her charts from the battery of cognitive tests that my doctor had requested.
I have APOE4, the Alzheimer's risk gene, and he felt it was important to track my memory over time.
My palms started tingling. Was this how it started? Today, you're forgetting where you put your keys, tomorrow you're forgetting your own name and shuffling around in a hospital gown.
"But your crystallized intelligence," she continued, "is solid."
I felt my guts relax. "That's good, right?"
She explained, "If your brain were a computer, working memory would be its RAM. It temporarily holds and processes information, like remembering a phone number long enough to dial it or doing mental math. Yours is way below average—imagine trying to juggle while holding only two balls when most people can handle four."
"On the other hand," she went on, "your crystallized intelligence is like your mental library—everything you've learned, the skills, facts, and experiences you've accumulated. That part of your brain is above average."
Her assessment rang true. I could barely remember a simple grocery list without spacing.
"You might want to get tested for ADHD," she suggested. "Poor working memory is often indicative of some form of ADHD."
I left the appointment feeling unsettled. Something about it didn't sit right—there was no way I had ADHD. I had always struggled with anxiety, but I'd never struggled with focus.
I'd noticed the endless stream of TikTok videos and social media posts about adult ADHD diagnoses and rolled my eyes. It had become the explanation for everything—another mental health meme where everyone thought they had the disorder.
I'd always been proud of my ability to power through work, tick off to-do lists, and juggle multiple projects. If anything, I saw myself as productive and organized—traits that seemed at odds with having ADHD. I had dismissed it as overhyped. A diagnosis given out too freely, especially in regards to the growing number of kids being prescribed amphetamine drugs.
While I was skeptical, I spent the next afternoon deep-diving into ADHD.
As I read, my skepticism began to evaporate and I started to feel like an asshole...
The first thing that struck me was how quantifiable it was. I learned that scientists can literally see a difference in the brains of people with ADHD on MRI scans and that ADHD brains even grow more slowly. Reaching their peak thickness three years later than their peers in regions controlling attention and motor planning. Three years. That's the difference between starting high school and getting your driver's license.
I couldn't deny it anymore—ADHD was as real as any other medical condition. I was reminded of how my parents' generation had scoffed at the idea of "anxiety" and "depression" and their fears that everyone was popping Prozac to avoid dealing with the reality of life. Was this just the modern equivalent? Was I, just like 90’s boomers, a mental health bigot?
As I dug deeper, I discovered that ADHD isn't just visible in brain structure—it's fundamentally written into our genetics. According to a study in Nature Genetics, ADHD is up to 88% heritable (even more than height!), making it one of the most inherited psychiatric conditions out there. If you have it, there's a near certainty that one of your parents does too.
Reading this, my thoughts turned to my father: his constant forgetfulness, his impulsive purchases, his encyclopedic knowledge of random topics paired with an uncanny ability to tune out or forget whatever everyone else deemed important. I wondered if he might have ADHD too.
For years, I'd treated what I thought was just anxiety with an SSRI (vortioxetine), and while it helped a ton, that frantic, life-on-fire feeling of being overwhelmed had never really gone away. Studies show why: up to 50% of adults with ADHD also have anxiety disorders, suggesting what I thought was just anxiety might have been masking a deeper neurological difference.
I was shocked to learn that ADHD's downsides extended far beyond distraction. Untreated, it has profound effects on those who have it, to the point where it can shorten their lives by almost a decade.
A 2015 Lancet study found that people with untreated ADHD die, on average, 9.5 years earlier than their peers. Not from the condition itself, but from its cascade of negative effects: accidents, impulsive decisions, and self-medication.
Research shows adults with ADHD are also five times more likely to develop substance use disorders, with up to 25% struggling with drug or alcohol addiction. Suddenly, my five nights per week of partying and binge drinking throughout my twenties made a lot more sense—the only way I could relax during the stressful ramp-up of my businesses. Self-medication.
I also thought of the rampant drug and alcohol abuse in my extended family. Sure, this wasn’t a blanket explanation, but if what I was reading was true, there were likely a few family members who had untreated ADHD and had instead turned to drugs and alcohol, destroying their lives in the process.
Yet there's hope: studies show that stimulant medication works in 70–80% of cases, making it one of the most effective psychiatric treatments across any illness.
A Swedish study of over 38,000 individuals with ADHD found that stimulant medication reduced substance abuse rates by 31% compared to those not taking medication. The protective effect was even stronger in younger patients, with those 15 and under showing a 62% lower rate of substance abuse.
Fortunately, many patients who start taking stimulants as children respond so well they eventually stop needing medication by adulthood—the medication potentially rewiring their brains.
My concerns about treating children disappeared. This now seemed like a critical intervention.
But here's where the story takes an unexpected turn. It’s not all bad news—in fact, in many ways, ADHD can be a gift.
While ADHD can be challenging in traditional settings, these same traits can become surprising advantages in the right context. A recent study found that 27% of entrepreneurs have ADHD traits—three times the rate in the general population.
This includes some of the most successful business leaders: Richard Branson has been open about his ADHD diagnosis, crediting it for his creative thinking and risk-taking ability. JetBlue founder David Neeleman has described how ADHD helped him see opportunities others missed, while IKEA founder Ingvar Kamprad used his ADHD traits to build one of the world's largest furniture companies.
It makes a lot of sense. The very traits that make traditional jobs challenging become superpowers in entrepreneurship: a tendency to see the big picture while delegating details, the ability to hyperfocus intensely on whatever interests us, a knack for building systems to compensate for our weaknesses.
Even our social tendencies—the constant need to connect, share, and build relationships—create powerful networks that drive business success. The entrepreneurial world, with its constant change and need for adaptability, seems almost perfectly designed for minds that thrive on novelty and creative problem-solving.
ADHD may represent an evolutionary advantage that's mismatched with modern life. Some researchers propose these traits helped our ancestors excel at hunting—where heightened awareness of movement, quick reactions, and constant environmental scanning were crucial survival skills.
As Thom Hartmann puts it:
"The hunter is easily distracted by movement and sound—traits that make them exceptional at tracking prey but challenging in today's structured environments."
This perspective helps explain why ADHD traits correlate with entrepreneurial success. Both hunting and building businesses reward adaptability, quick pattern recognition, and comfort with uncertainty.
It's as if the business world had accidentally created the perfect environment for minds that don't fit the conventional mold. Suddenly, my own career path made a different kind of sense.
As I read all this, it was like watching dominoes fall in slow motion—each symptom clicking into place, each pattern revealing itself with almost painful clarity.
I realized the intricate web of systems I'd built wasn't just about being organized—it was a coping mechanism. I'd become obsessed with David Allen's Getting Things Done productivity system, spending hours maintaining its complex organization system.
My phone was filled with thousands of Siri reminders shouted while driving, desperately trying to capture the stream of urgent thoughts racing through my brain before they vanished like smoke.
I needed these systems because without them, important tasks would slip through the cracks of my unreliable working memory.
Every notification, every color-coded calendar entry, every obsessively maintained checklist was compensation for what my brain couldn't do naturally.
Reading about how ADHD plays out in romantic relationships and family life, I recognized myself.
Someone who would drift off during intimate conversations with my partner, yet could spend hours intensely focused on unrelated projects. Forgetting commitments and neglecting agreed upon chores.
I felt that I was a loving and supportive partner in many ways, but these seemingly basic aspects of home life felt inexplicably challenging.
These challenges weren't limited to relationships.
My work life prior to starting my company was equally difficult. I couldn't stick to the same routine tasks day in and day out and frequently jumped from job to job, impulsively quitting and moving on, sometimes without notice because I couldn't bear the idea of showing up to work another day.
So in 2006, driven more by desperation than inspiration, I started my first business. Over the next five years, I impulsively launched ten separate companies, attempting to be the CEO of all of them at once.
As you can imagine, this failed spectacularly. It wasn't until 2014 that I finally found my groove: buying great companies and hiring wonderful CEOs (who don't have ADHD) to run them.
My inability to handle details didn't leave me any choice but to embrace delegation.
While many entrepreneurs struggled to let go of tasks, I had the luxury of being absolutely terrible at them from the start.
My habit of getting obsessed with random parts of the business meant I'd go super deep on M&A for a few weeks, suddenly get bored, then jump to product, then marketing—basically whatever shiny object caught my attention that week.
This scattered approach somehow worked in my favor—being an inch deep and a mile wide on every part of the business turned out to be exactly what a CEO needed to be.
Then there was my insatiable need to meet new people and socialize—often the most immediately rewarding part of my day, a reliable hit of dopamine. I'd strike up conversations with anyone, everywhere.
Not so much networking as a complete failure to hold my cards close to my chest. This chronic oversharing somehow worked in my favor. When problems came up, I usually knew someone who could help.
Within a matter of weeks, I had booked a formal diagnosis, and a month later, my neurologist's suspicions were confirmed: I had inattentive ADHD. They recommended a stimulant, and one day I buckled up and took Vyvanse.
It was transformative in a way I never expected.
The most surprising thing was the quiet. My brain previously felt like Times Square at New Year's, hundreds of thoughts competing for attention at once. On Vyvanse, it was more like a library. One thought at a time, each one getting its proper attention before moving to the next.
Imagine living your whole life with a radio playing static in your head, and then someone finally shows you where the 'off' switch is. That feeling of being overwhelmed by midday, like hitting an invisible cognitive wall—vanished. Since I started treatment, for the first time in my life, I feel calm, focused, and present.
I'm sharing all this because for years, I felt kind of broken.
Like I was constantly letting everyone down. Sure, I'd found ways to cope—building a business where I could delegate all the things I was terrible at, engineering a scaffolding of to-do lists and reminders, and surrounding myself with amazing people who could handle what I couldn't.
But that strategy falls apart in your personal life. You can't delegate being a dad, or a partner, or a friend. Those relationships require consistency, attention to detail, being present—exactly the things ADHD makes so challenging.
The impact on family life has also been notable. Before, by dinner time, my mental energy would be completely depleted. I'd be there physically, but mentally checked out, running on empty after a day of trying to keep it all together.
Now I can follow a bedtime story without my mind wandering off to work emails, or sit through a family dinner without yawning or zoning out. The day I first took medication, all I kept thinking was that I wish I'd been taking this my whole life, or at the very least, before my kids were born.
All this is to say, getting diagnosed has been transformative for me.
Like discovering the long-lost manual to my brain and realizing I've been using it wrong this whole time. I wanted to share in hopes that someone like me—who's struggling but has never thought about ADHD—might read this, see themselves in it, and seek treatment themselves.
If you're reading this and any of it sounds familiar, I'd recommend checking out The ADHD Effect on Marriage by Melissa Orlov and Dr. Russell Barkley's excellent book, Taking Charge of Adult ADHD. Both were super helpful in figuring this out.
And if you're listening to some of this and nodding along, thinking you might have it too, you could try prompting ChatGPT with this prompt to suss it out:
Act as a clinician conducting a pre-assessment for ADHD. Ask me structured, clinically relevant questions to explore my symptoms, history, and their impact on my life. Cover: core symptoms (inattention, hyperactivity, impulsivity), their effect on daily life (work, relationships, self-care), medical and family history, lifestyle factors (sleep, diet, stress), coping strategies, and how long symptoms have persisted. Summarize my responses into a professional document I can share with a clinician.
You should also watch the excellent YouTube video on diagnosis by Russel Barkley, which I link in the thread below.
Of course, ChatGPT can't diagnose you, but it can give you a sense if maybe it's something to look into.
There are tons of telehealth pill-mills that ask you ten questions then rubber stamp you a lifetime prescription of stimulants—you should avoid those. I think it's worth doing a full assessment, which is a multi-hour process that includes qualitative and quantitative testing.
I got diagnosed at Resilient Health in Victoria and was impressed by how thorough they were. The assessment wasn't some quick DSM checklist. It was a comprehensive process involving interviews with me, as well as Zoe and my family, coupled with extensive attention and memory tests. It took about six hours altogether, and at the end I had a detailed document explaining both my ADHD diagnosis and my overall psychological profile.
And if you're curious about brain health in general—something almost nobody seems to assess outside of my extreme health nerd friends—the neurologist who identified this for me was Dr. Kellyann Niotis. She's amazing, and I highly recommend checking her out, ADHD or not.
Do you have ADHD too? I'm keen to hear your thoughts and experiences. I’m only a few months into navigating this, so I have much to learn :-)
Here’s a link to a Google Doc with a bunch of the resources I found helpful through this journey.
-
Men: no offense, but you dress like shit.
Seriously, most of you look like dopes.
I'm not any better.
For years, I'd wear the same uniform: hoodie, Patagonia jacket, and some dorky but comfortable shoes.
After getting divorced though, I knew I needed to get it together.
I hired a "Personal Stylist" (actually not that expensive) and had her send me a whole bunch of outfits.
And I started getting compliments daily! It felt amazing!
Because after all: the outfit makes the man.
We think we need to get ripped. But honestly, wearing a well-layered and color coordinated outfit and nice shoes is 90% of the battle.
I loved having a personal stylist, but found it kind of annoying having to depend on someone else to not look like a schmoe.
But then something crazy happened:
I started just asking ChatGPT instead.
Every day, I'd upload a photo of whatever pants I was wearing and say "complete this outfit".
I was amazed by how good it was. And it got better over time, as I trained a custom GPT on my wardrobe.
Suddenly I didn't need my personal stylist—I had an AI one.
But my ChatGPT based system was kind of fiddly. It required prompting and uploading lots of photos and messing with instructions to produce something good.
So, I saw an opportunity. I called up my friend Hamza and told him I wanted to turn this into a thin wrapper app.
That was about 4 months ago, and now we have a beta that uses OpenAI and a few other APIs to achieve the same thing in a beautiful app.
TLDR: it's called Vibe and here's how it works:
1. Take photos of all your key wardrobe items (t-shirts, pants, overskirts, jackets, watches, etc).
2. Tell it what kind of outfits you need (date, work, etc) as well as the season (summer, winter, etc).
3. It generates beautifully layered and coloured coordinated outfits utilizing your wardrobe items and then renders an image of what that outfit looks like.
It's really cool. We have a beta live on the iOS App Store . It's still pretty rough, but you can see where it's going and play with it.
But I have a problem:
I don't know what to do with it. I don't know the first thing about scaling an app like this.
I need someone to take it over and turn it into something and I don’t want to be the one who funds it.
I actually think it's a great idea and a really well built app, but now I need someone young and hungry to turn it into a real business.
I'm down to give someone 50%+ of the equity and pass the baton.
Know someone great? Send them my way.
Random Stuff:
- I’m looking for a private covered or indoor pickleball court in Victoria, BC that I can rent/borrow/beg for during the winters. Does anyone have any leads? The only one I’m aware of is a 40 min drive away so I’m looking for something more central.
- ‘Song In My Head’ by Madison Cunningham is stuck on repeat in my brain. Very good.
- I have a lot of small interior design projects that are small enough to not necessitate my favorite interior design firm (Studio Roslyn) but still require someone with great taste. For example: choosing a nice light fixture in a random secondary bathroom / Doing a simple kitchen reno in one of my rental properties.
I’m looking for a young, scrappy (read: affordable) person with incredible taste and experience with projects like this. I’m willing to take a bit of a chance on someone, but you can’t be a complete amateur and you have to demonstrate that you have great taste and have done a few projects somehow. If you know someone like this, email me :-)
- I'll be visiting Pheonix/Scottsdale for a few days in the next couple weeks and I'd love to meet interesting people. If anyone is based there, email me!
That’s all for now…
-Andrew
Did you enjoy this newsletter? Say thanks by checking out one of my businesses:
Follow me on Twitter/X: @awilkinson
Forwarded this message? Sign up here.
|
|
|