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 Bulletin: I'm in Toronto at TIFF this week. Anything cool happening?
Here's what I'm thinking about…
I want you to read my newsletters and seethe.
To think, "God, he's just THE WORST," as you hate-scroll.
Or mutter "fucking tool" when I say something obnoxious on a podcast, white-knuckling the steering wheel.
Not all of you. Just some.
Maybe 2-3%—that's the sweet spot.
Ten years ago, this would have struck me as insane. I would have wanted the opposite.
Because in 2013 I read a quote that changed my life:
"It takes 20 years to build a reputation and five minutes to ruin it."
This is a famous line by Warren Buffett—someone many of us have modeled our lives after.
This advice, while valuable in moderation, became toxic when I took it to the extreme.
Why?
Because it's impossible.
After reading it, I became obsessed with how I came across to others.
I thought that everyone—online and off—had to walk away from every interaction liking me.
One negative article, one misstatement, one failed commitment, and I'd be toast.
I had to do exactly what I said and follow through. My behavior had to be consistent and predictable.
After all, that's how a reputation is built. Brick by boring brick. Until one day, you die, honorable and forgotten forever.
This idea crystallized one afternoon at a pub with my dad. He had recently retired from architecture, so took him out for a celebratory drink and asked what he wanted to do next.
"You've always wanted to build your own buildings," I said, taking a sip of my beer. "Why not become a real estate developer? With all your contacts, you could get up and running in no time."
"Andrew," he replied, leaning back in his chair. "Once people put you in a mental box, they punish you for leaving it. In their minds, I'm in the 'architect' box. If I suddenly called them up and pitched a real estate development, it would hurt me more than starting fresh. Everyone hates it when you change boxes."
My stomach dropped—I knew he was right. I'd felt it a million times, though I hadn't quite put my finger on why.
Nothing made me cringe harder than the restaurateur friend pitching me on his tech startup. Or my yoga instructor getting their real estate license and trying to sell me a house. Or my lawyer announcing they're becoming a psychotherapist.
I'm ashamed to admit it, but my gut reaction was always: "Stay in your lane."
Which is particularly hypocritical given how often I want to flip flop through everything myself: hobbies, businesses, communities, opinions—you name it. I hate in others what I secretly hate about myself.
We're all desperate to put one another in these boxes. I often get labeled "investor" or "entrepreneur". But even within that, there are sub-boxes. Tech investor, not real estate. Software businesses, not physical products. Bootstrapped, not venture. Crypto skeptic vs. crypto bull. Each label becomes another bar on the cage.
And we love punishing people for leaving it…
David Solomon runs Goldman Sachs, but when word got out that he DJs on weekends? The financial press went apoplectic (I can't imagine they would have said the same if he was golfing).
Jonah Hill starts surfing? Instant meme fodder.
Kim Kardashian passes the bar to fight for prison reform? A vanity project.
Michael Jordan wants to play baseball? Abject betrayal.
We're all prison guards, basically. Making sure everyone stays in their assigned cells.
Why? Because our brains are prediction machines. They get upset when people behave in a manner that doesn't meet their predictions. Thus, step out of your box, and people (and their brains) won't like it.
This happens to me often.
There are people who know me based on my public business persona. They know me as a Buffett wannabe, building a holding company using value investing principles.
This is true. But I also love learning by jumping into random new projects that don't fit this mold.
My portfolio includes all sorts of businesses that would give Warren Buffett hives. I've lost my shirt starting restaurants. Acquired failing newspapers. Invested in companies with a 1 in 100 chance of working.
Tiny continues to buy wonderful businesses at fair prices (the Warren Buffett playbook), but the rest of my life doesn't fit neatly into that "value investor" box.
I am both a disciplined value investor and a creator of chaotic startups across dozens of industries. These two things aren't supposed to coexist.
It's not just me. I recently polled a group of close friends and asked them what they would do for work if they couldn't do their current job.
One response struck me in particular:
A friend runs a huge industrial holding company, but he told me that if nobody was watching, he'd sell it and start his own restaurant.
And better yet, he wouldn't just be the owner. He'd be the chef, sweating it out behind an oven in the back.
His true, authentic passion is cooking, but he feels like he could never step out of the life and reputation he'd established for himself to follow his passion.
What would people say?
That he'd lost his mind, left his successful business in a completely different industry, and gone off to start…a restaurant?
Imagine the gossip and judgement he'd face.
You might think charitably of yourself. That you'd hear that he'd started a restaurant and think, "good for him." But let's be real: you'd likely delight in the gossip and think "stay in your lane," just like everyone else.
Deep inside, you might even subconsciously hate him for it, or want him to fail. Because he did the thing you're too scared to do yourself.
He'd have escaped the same prison you're in. Against the rules. Not fair!
So instead, he continues to do what we all do: shrug and continue to live in society's reputational cage.
I'm sure way too many of you are nodding along. Most of us do this to one degree or another.
I've lived in a cage like this for decades.
This applies to many things. Legal degrees. Bad marriages. Letting down your parents. Moving away from the city you swore you'd never leave. The industry you've spent 20 years building credibility in.
Each, a promise or commitment made by a different person—the person you were before you changed in whatever way it is you've changed. A sort of reputational quicksand, each step out harder than the last.
For me, this obsession with maintaining reputation—playing by these inflexible rules—was a recipe for misery.
If I continued playing the game, I had three equally terrible options:
Terrible Option 1: Hide and say nothing. Fly under the radar. Be a cipher. (Impossible, for an extreme extrovert like me.)
Terrible Option 2: Become a caricature of myself. A personal brand instead of a person. Avoid doing anything controversial.
Terrible Option 3: Live a double life. Perform one thing and do another in secret. The world wouldn't catch on and give me the corresponding social beating, but I also wouldn't get to share my passion with others.
For a long time, I chose Terrible Option 3. I toned down the things I mentioned publicly and didn't talk about many of my projects because they didn't fit the template.
It felt inauthentic. Like, with every passing day, a little piece of me was dissolving.
I realized it had gone too far when I found myself deleting a tweet for the fourth time. Not because it was wrong or offensive, but because someone, somewhere, might misinterpret it.
I was slowly drifting towards becoming what I'd always mocked.
A corporate politician. A beige person. Human vanilla extract.
Then, in January, I came across a book called The Courage to Be Disliked.
I needed this book. So much that I actually felt personally attacked by it.
The core message is that seeking recognition from others is a trap.
We bend ourselves into pretzels trying to meet everyone's expectations, but it's impossible. You literally cannot make everyone happy. And trying to do so means living someone else's life, not your own.
The book argues that having the courage to be disliked is the only path to freedom. Not by being an asshole, just accepting that living authentically means some people won't like you.
Reading it felt like someone finally handed me the keys to my own cell.
It gave me permission to start breaking the rules. I was done with the likability game. I was going to have the courage to be disliked. Hated, even.
To live authentically, I would do what I wanted to do, and talk about what I wanted to talk about, so long as it didn't hurt anyone else in an unfair way.
Change my mind. Be unpredictable. Jump around.
That became my 2025 resolution.
Now, to be clear, we're talking about a very specific type of reputation. What the public at large thinks about you.
Should you maintain a reputation as a fair and ethical partner, whether it's romantic, social, or business?
Absolutely.
But should you obsess over what the world would think, as Mr. Buffett puts it, imagining every action appearing on the front page of The New York Times?
In most situations, absolutely not.
I stopped playing for universal approval. I chose the courage to be disliked. That means I'll say things some people won't like, and I'm okay with that.
Disappointing people is the price of an authentic life.
So here's my dare:
Let someone down today. Say the thing that's been rotting in your chest.
Start small. Post your anime fan fiction. Tell your gym bros you love Pilates.
Then, go bigger. End the relationship everyone thinks is perfect but is actually miserable. Admit what you thought was your dream job is a nightmare. Tell your business partner you want out. Stop pretending you enjoy the thing that's slowly killing you.
Watch what happens: 90% won't notice or care. 8% will respect you more. 2% will hate you.
And you'll feel free for the first time in years.
Because here's what I learned: The cage only exists if you believe in the bars.
I'd rather have 2% hate the real me than 100% applaud a performance.
PS: Thanks to all you hate-scrollers. I couldn't do it without you.
A few weeks ago, I hosted my third annual Interesting People event.
I'm still buzzing. I recently described the feeling to a friend as a "low grade MDMA high that lasted for 3 days". Everyone gelled perfectly, we got lucky with the weather and logistics, and most importantly, we packed the room with 150 fascinating people from the worlds of science, comedy, business, and philanthropy.
It was easily our best one yet. I'll write more about it soon, but in the meantime, here's a few highlights:
I honestly can't believe how well it went. A huge thank you to my friends Monica Lim and Nick Gray who help me put it on every year 🙏
Speaking of events, I'm hosting one for lonely conglomerateurs (yes, that's a word 🤢, and if you ever want to get punched in the face, introduce yourself as one).
There are tons of support groups for executives and CEOs, but none for folks who run holding companies. It's a unique role with a rare structure and set of challenges.
Frankly, it can be pretty isolating because there are so few people who can relate to our problems (of which there are many: perverse incentives, compensation negotiations, reporting complexities, etc).
In fact, I so rarely meet people who I can talk to about these problems with that I had to start my own event. It turns out, there are dozens of us!
I hosted the first Conglomerateurs meetup in May in Vancouver, and it was incredible. We assembled a collection representing hundreds of companies and many billions of dollars in revenue across the group. We spent 3 days diving into our collective problems in a super confidential format, and everyone really clicked.
Now, we're doing it again. In early January. It will be very intimate, with less than than 30 people attending.
This one is in Maui at my absolute favorite resort, and we're giving everyone the option to bring their families along to enjoy the resort while we talk business, and I've got some incredible guest speakers coming.
We have a few spots open, so if you run an at-scale holding company ($25M+ in revenue, at least three businesses, serial acquirer) and you're looking for your tribe, you should apply.
The answer is very simple: ask questions.
I was recently on the East Coast for business and I had lunch with someone who, no joke, over the course of an almost two hour meal, went on a monologue about himself and asked me exactly zero questions.
At the end of the meal, as we were walking out of the restaurant, he remarked, "man, that was fun!"
It was. For him.
People feel good when you ask them questions, and I had done nothing but.
I'm partly to blame for this. I'm an inveterate question asker, and it can sometimes cause people to ramble. But this was next level.
The sad truth is that this isn't uncommon—not in my experience, and apparently not in others' either. I regularly hear from women whose dates launch into similar monologues. And that's on a first date, when you'd expect people to be at their most self-aware.
Harvard researchers quantified this effect: across multiple studies involving hundreds of conversations, people who asked more questions were consistently rated as more likable by their conversation partners. The effect was particularly strong for follow-up questions—those that build on what someone just shared.
So, my friends, here are a few of my favorite questions to ask people:
When someone shares something as a quick aside (that they got divorced, their business failed, they had their first kid—whatever), ask:
These always lead somewhere interesting.
Conversations should be a game of tennis, rallying back and forth. It's no fun to hit the ball against the wall by yourself.
Want better conversations? Follow the golden rule: in your next conversation, aim for a 50/50 split between sharing and asking. Notice how different it feels, and how much more your conversation partner lights up.
David Brooks wrote a book I loved that deep dives on this exact topic last year. It's called How To Know a Person and it's required reading for anyone who aspires to be an exceptional conversationalist.
"I want to send you something I'm working on…"
Ugh. My friend Matteo asked to send me his mattress gadget. I didn't want it.
I knew it would end up rotting in my basement with all the other expensive health tech, next to my Theragun, red-light therapy panel, and infrared-sauna blanket.
I guarantee you've heard of Matteo's company: Eight Sleep.
Every podcaster won't shut up about it. It's a temperature-controlled mattress pad that supposedly optimizes your sleep.
But I thought it was unnecessary. I blast my AC at arctic levels and the idea of a water-filled pad on my bed seemed like a disaster waiting to happen.
So, when the box arrived, I ignored it for three months.
Matteo kept texting: "How do you like it?"
After his fourth follow-up, guilt won out. I explained to Zoe that he'd sent it, and it was expensive so we had to try it.
She was unimpressed. She was already bothered by my gadget addiction, and now it was invading our bedroom.
The first night, I didn't notice much. But to my surprise, Zoe loved it.
For years she'd been waking up in the middle of the night, too hot or too cold, tossing and turning for hours. The Eight Sleep had automatically adjusted her temperature all night and prevented it.
It turns out that women's hormonal cycles cause wild temperature fluctuations during sleep, and Eight Sleep tunes your side of the bed based on your age and gender.
It's pretty cool. It learns your patterns and preferences, then adjusts accordingly—cooling for deep sleep, warming for REM, then gently heating to wake you up in the morning.
For me, it took three weeks to notice the benefits. But then I discovered something that might have saved my relationship: the sleep tracking showed exactly when and how much I snored.
I snore. Really badly. Zoe used to elbow me awake 3-4 times every single night.
The app showed me exactly when and how much I snored and I became obsessed with my "snoring score." Side sleeping—20% reduction. Breathe Right strips—a further 50% drop.
Within six weeks, I'd cut my snoring by 70%. No more elbowing.
Now, we both wake up feeling more refreshed. We're eight months in, and we're hooked.
I know the last thing you think you need is a mattress cooling system, but I'm telling you, DO IT.
PS: Matteo gave me a discount code: NEVERENOUGH (saves you $300)
I've been rediscovering The Beatles.
My love affair started the moment I hit play on Rubber Soul…
I was fourteen and I'd just gotten a Sony Discman. On the way out the door, I grabbed an interesting looking CD case with four shaggy-headed dudes on it from my parents' music collection and threw it into my backpack.
I pushed the shiny disc into the player, threw on my headphones, and listened to the album straight through as I gazed out the window on a sunny drive to a cabin we'd rented for the summer.
It instantly clicked. The perfect album, and one I've listened to hundreds of times since.
Over the past few days, I've been devouring John & Paul: A Love Story in Songs, Ian Leslie's wonderful new book about the relationship between John Lennon and Paul McCartney. If you're into The Beatles, or even just interested in how creativity happens, it's a great read. It's been the perfect way to revisit their epic catalog (195 songs) and discover the stories behind each track.
Today, I've been driving around blasting I'm Looking Through You, which, beneath the psychedelic riffs, captures McCartney's painful realization that his girlfriend had fundamentally changed: that the person he'd fallen for was no longer the same person sitting across from him. I'd been listening to this song for decades without even knowing what it was about.
Trust me on this one: if you like The Beatles, read this book.
More importantly, if you don't like The Beatles, then this needs to be rectified ASAP. Stop what you're doing and listen to Rubber Soul all the way through, otherwise we can't be friends.
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.
PO Box 42052 RPO Oak Bay, Victoria, BC V8R 6T4
