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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…
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Life goals from Charlie Munger.
Last week, The Wall Street Journal ran a great piece on Charlie Munger’s final decade.
Despite losing vision in one eye and much of his mobility by his nineties, he forged ahead.
This was nothing new for him.
By his early thirties he had already buried his 9-year-old son, Teddy, who died of leukemia, and gone through a divorce that left him nearly broke.
Then, in the '70s, he watched his investment partnership drop by roughly 50% in the 1973–74 bear market and came out limping.
Again and again, for almost a century, he picked himself up, refusing to wallow.
Right up until his death at 99, he kept burning through an endless pile of books, helping a young neighbor, Avi Mayer, build a real-estate company that went on to buy thousands of garden apartments in Southern California, and tinkering away on his side hobby of designing college dormitories.
My business partner Chris and I were lucky enough to spend a fair amount of time with him during his twilight years. I can confirm that he was hilarious and razor sharp until the very end—often holding court until late in the night at dinner parties full of what he jokingly dubbed his “groupies” (young investing nerds like us).
Here's a story that captures how old he was when we met:
We asked him about inheritance, and he mentioned that most of his wealth would go to his children and grandchildren.
“Aren’t you worried you’ll spoil your grandchildren, Charlie?” Chris asked.
“My grandchildren are FIFTY YEARS OLD!” he replied, with a laugh.
My favorite excerpt from the WSJ piece:
“Near the end of life, Munger leaned on humor for strength.
He told family members that Diet Coke was responsible for his longevity, lightening the mood.
And he shared a wish with a visitor.
‘Oh, to be 86 again,’ he said.”
Charlie’s life wouldn’t be ideal for most people. He was a bonafide polymath who spent 80% or more of his day with his head in a book or an annual report.
Most people’s brains aren’t built for that. Mine certainly isn’t.
But here’s a few of Charlie's key ideas that we should all apply:
- “Always take the high road, it’s far less crowded”
He didn’t waste time on bad people and focused on operating in a way that prioritized win-win outcomes. If he trusted you, that was it—he didn’t want to have a 60-page contract.
“The great lesson of life is to get toxic, unreliable people the hell out of your life — and do it fast.”
- “The best way to get what you want is to deserve what you want.”
One of his favorite ideas was that the best way to get a great spouse, great friends, and great partners is to deserve them. That’s a very un-2025 idea—just quietly become the kind of person other good people are happy to bet on and build a life with.
- “Envy, resentment, revenge, and self-pity are disastrous modes of thought. It’s very counterproductive for an individual to feel like a victim—even if he is.”
By any normal standard, he had earned the right to be bitter. Divorce, the death of a child, major health problems. Instead, he chose to push on and continue contributing.
- “I constantly see people rise in life who are not the smartest, sometimes not even the most diligent, but they are learning machines.”
It's hard not to succeed when you read every day.
- “Invert, always invert!”
My favorite Mungerism is inversion: the idea that, instead of trying to predict what will make you happy, focus on what you know makes you miserable, then avoid it.
He famously gave a speech about How To Guarantee a Life of Misery (do drugs, let envy and jealousy consume you, be unreliable, etc) and said that the best way to think through a problem was to work in reverse.
If your goal is to help your children, write down all the reliable ways to ruin their lives—and then work through how to avoid those things.
If your goal is a good life, list the habits that would produce a bad one and treat them like poison.
In 2017, I wrote an article about how Chris and I use inversion to avoid hating our lives.
- There’s a famous saying: “Never meet your heroes. They’ll only disappoint you.”
Not Charlie. He was the real deal, and his life is worth studying.
Read it here
- Spending $40,000 to make $3.5 million.
My business partner David texted me the other day:
“Get this: we’re building a single AI automation that will cut this company’s labour cost by $50,000 and should add an estimated $300,000 in recurring revenue.”
The software company they're working with had a whole team doing miserable, manual work—reaching out to churned customers and trying to win them back.
His automation should cut resources required by half, saving $50,000/year, and he estimates it'll add around $300k in ARR.
If this plays out as expected, that’s an extra $310,000 in profit for the owner this year (and $350,000 the following year).
If we assume the business is worth 10x EBITDA (it’s growing nicely and high quality), that would mean they paid David and his team at Digital People, our AI automation agency, $40k to increase the value of their business by $3.5 million.
That's a 775% cash-on-cash return in year one, and an 87x long-term return.
It's the wild west in AI automation, and I'm astounded how many founder friends are sleeping on AI agents (or as I like to call them, digital employees).
Do you own a business?
Do you want to be like my sleepy, checked-out friends?
If the answer is no, you should talk to David.
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A few of my favorite things from 2025.
It’s almost Christmas, so I figured now would be a good time to share an annual roundup of highlights from the year.
Hopefully you find a few things here that you like :-)
🎵 Songs I Couldn’t Stop Listening To
1. It Might Be Raining by Dan Mangan
Dan made me cry a lot this year. In a good way.
2. Song In My Head by Madison Cunningham
This song is ear heroin. It’s been stuck in my head all year.
3. Dear Boy by Paul McCartney
I had somehow never heard this album until this year.
4. Strawberry Fields Forever (Take 1) by The Beatles
I like this more than the album version.
5. Don't Be Cruel by Billy Swan
Haunting and wonderful.
📚 Favorite Books
1. The Courage to Be Disliked by Ichiro Kishimi & Fumitake Koga
This book is oddly written (it's translated from Japanese), but it changed my life. I wrote about its effect on me here.
2. The Kid Stays In The Picture by Robert Evans
Robert Evans goes from pretty-boy actor to running Paramount during The Godfather era, then nukes his life in a haze of ego and excess. Pure Hollywood popcorn—probably half true, but insanely entertaining.
3. Barbarian Days by William Finnegan
I'd been gifted this book like three times but had zero interest in reading it. I don't care about surfing. God was I wrong. Beautiful stuff.
4. Rabbit At Rest by John Updike
I finally made it through the entire Rabbit series. This book was by far the weakest of the four, and it still makes my top 5 list. Updike is, in my opinion, the best fiction writer of the last century.
5. Lorne: The Man Who Invented Saturday Night Live by Susan Morrison
A window into the kind of person who does the same job obsessively, week after week, for 50 years. So many great anecdotes about Lorne and his crazy famous friends. I couldn’t put this down.
🎬 Movies I Loved
1. Eternity
A man dies and goes to heaven, followed shortly by his wife—who re-connects with her hunky ex-husband, creating a hilarious love triangle. My favorite film from TIFF.
2. Sentimental Value
A movie about boomer dads who compress their trauma into blood diamonds deep inside themselves. Great stuff.
3. Nosferatu
Somehow both absolutely terrifying (there are a few scenes I can't scrub from my mind almost a year later) and hilarious. Robert Eggers never fails to make my skin crawl.
4. Pee-wee as Himself
Brought back long forgotten memories of watching Pee-wee’s Playhouse as a kid. I had had some vague notion that he was a pedophile or had done something really bad. It turns out, his career was unfairly destroyed—he was just a closeted gay guy who made a bad decision in a porn theater. A profoundly unfair story about an incredible performer.
5. The Naked Gun
The first movie I’ve seen in theaters with the boys (ages 6 and 8) where we all laughed our heads off together. Pure gold. Akiva Schaffer for president.
😂 Hardest Laughs
1. Gianmarco Soresi - Thief of Joy
Stumbled on this and was dying within five minutes.
2. Shane Gillis’ Trump impersonations on Kill Tony
If you close your eyes, it’s Trump.
3. Jon Glaser’s Soothing Meditations for the Solitary Dog
Almost made me crash my car from laughing.
4. Conner O'Malley's Slugs video
Unhinged as always.
5. Tilek All Better - Strangers Ease My Soul-Crushing Battle with Anxiety
Very John Wilson. The guy who walks up to him in the park 😂
🛒 Rampant Consumerism
1. AeroPress Coffee Grinder
I’ve been beta testing this thing for months and it was worth the wait. My favorite feature: it comes with a drill bit for fast electric grinding.
2. Laifen P3 Pro Razor
Apple-level design for a razor. Makes my old one feel like a joke.
3. Garmin Bounce
Despite what To Catch a Predator would have you believe, it's almost statistically impossible your child will be abducted. But just for peace of mind, you can get a Garmin Bounce.
4. TRMNL e-ink display
Lives in my kitchen, shows countdowns and calendars (and my death clock!). Love it.
5. Zefferano Poldina Pro
Battery powered lights for indoor/outdoor dining, parties, or anywhere you need to create low-light ambiance. Instant cozy—perfect for dinner parties.
💻 Nerdy Stuff
1. Lindy
I've built dozens of amazing automations with this thing. Completely obsessed.
2. Beeper
Superhuman but for texts. Combines iMessage, WhatsApp, Signal, and Slack.
3. WisprFlow
iOS + Mac dictation app that actually works. I text with my voice now.
4. Ramp
After years of misery managing corporate cards with Canadian banks, Ramp finally came to Canada and I love it. If your company has credit cards, you need to switch.
5. Freedom
Blocks misery-inducing sites like TikTok, Instagram, and Reddit. Not having easy access to social media and news has made my life infinitely calmer.
🙋♀️ Favorite People
I got to know a lot of really cool people this year. Here are some favorites:
1. Dan Mangan
I needed a musician for my Interesting People event last summer and someone threw out Dan’s name. I recognized it, but honestly, I'd never heard his music.
We booked him without a thought, and I had no idea what to expect.
Dan got up after a string of comedians and made an awkward joke about singing sad songs after all those laughs.
The room felt tense. I was worried.
Then, he gave the most incredible performance I’ve ever seen. Within minutes, I had tears streaming down my face, and he ended the show with everyone singing together. Unbelievable.
I've gotten to know Dan since, and he's a lovely, thoughtful, and supremely talented dude. I have a man crush on him. You should listen to his music and read his Substack.
2. Robbie Bent
Robbie runs a cult. At least that’s what Toronto Life calls it. Going to his bathhouse, Othership, feels like a religious experience. A mix between a holy ritual and a healthy night club.
We spent a few hours wandering Toronto together and talking about life and I was struck by his ambition and openness.
In an increasingly lonely and disconnected world, we need more people like Robbie.
So impressed with what he’s built. The OG Othership is in Toronto, but he just opened new locations in Brooklyn and Manhattan. You should go.
3. Alex Forman and Nash Park
I had completely written off standup comedy in Victoria, but got dragged to an OkDope comedy show.
Alex and Nash are hilarious, great people, and doing the best standup in town. If you live in Victoria (or Vancouver Island), you should go to a show.
4. Gillian Liu
I was speaking at a random ecommerce conference and Gillian happened to be behind me in the breakfast line. I liked her immediately—she was hilarious—but I was also blown away by the business she built.
While working full-time at an insurance company, she bootstrapped an online Korean beauty business called Kiyoko that hit over $10,000,000 in revenue.
She’s cool. If you’re in Toronto, you should email her for a coffee.
More importantly, if you like having beautiful skin, you should visit Kiyoko and stock up.
5. Josh Franklin
Over the last few years, I've started going to bed at 9 PM, but whenever I'd ask non-lame people what they were up to on weekends, they’d always say 'Club Loading.'
It turns out that two guys had taken over a former grocery store and built a makeshift nightclub —the type you’d typically find in Williamsburg, not Victoria.
I met Josh, one of the founders, through mutual friends. We immediately clicked and started brainstorming.
He's passionate about one thing: making great events happen in Victoria.
Earlier this year, we founded The Culture Fund to remove the financial barrier to hosting events in Victoria, and we just co-founded a new company we’ll announce soon 🤫
If you're into music, events, and making things happen, email him.
- Meet me in Maui?
But only if you’re a Conglomerateur—one of the rare weirdos like me who runs a holding company.
A couple dozen of us are meeting up in Hawaii, January 5-8th.
We’ve got some incredible speakers joining:
Ben Gilbert from the Acquired podcast.
Tren Griffin from Microsoft/25iq.
Glen Arnold, author of The Deals of Warren Buffett
And more. Want to come? (We only have 3 spots left)
- Mr. Market is confused by my platypus.
Ben Graham, the father of value investing, told readers to think of the stock market as “Mr. Market.”
An irrational old man who's euphoric one day and terrified the next.
Sometimes he thinks stocks can only go to the moon—other times he’s losing it and stockpiling gold under his mattress.
It's a fun metaphor…until it moves your net worth by millions of dollars a day and makes your shareholders sweat.
When Tiny went public in 2023, public market investors misunderstood us.
We're a collection of 28 businesses across diverse industries.
As you'd expect, Mr. Market scratched his head:
Why do they own software companies and a coffee maker company?
Why do they have a fund?
Why do their earnings jump around so much?
Why does the founder tweet all this emo stuff about getting diagnosed with ADHD on X?
Mr. Market doesn’t like complexity.
He likes simple businesses with a formula.
CEOs who say things like:
“We buy golf course management software companies at 7x earnings and increase prices by 15% per year.”
The public market wants you to look like a duck and quack like a duck.
To be consistent and never change course.
To have earnings go up in a straight line, quarter after quarter, at a prescribed rate.
But Tiny isn’t a duck. We’re a platypus.
Confusing at first glance, but well suited to what it does.
Being a platypus means embracing a certain amount of chaos.
When you have dozens of businesses doing very different things, something is always breaking, stalling, or surprising you, while other businesses knock it out of the park.
But viewed as a whole over the long term, the system works well. The strong parts more than compensate for whatever business is temporarily misbehaving.
We started Tiny with a simple mission: to buy wonderful, profitable businesses for the long term, almost always from founders.
Over time, that led us to own an eclectic mix of companies—not because we wanted complexity, but because we follow great founders, strong cash flow, and enduring products wherever we find them.
Unfortunately, that complexity showed up in our share price. Since we went public in 2023, our stock dropped more than 80% from peak to trough.
At one point in 2025, our entire business was valued at less than $200 million.
For a company with:
- $200M+ Revenue
- $65M+ Recurring Revenue
- $40M+ Adjusted EBITDA
- A 20-year track record of growth
- Founder alignment, with Chris and me holding the majority of shares
- A $200M fund that owns businesses doing $66M+ in annual revenue, where Tiny holds about 21.6% of the LP (~$42.2M NAV), plus significant upside via carry (see our 2024 shareholder letter for details)
[See Non-IFRS legal footnote at the bottom of this post]
Not to mention the businesses we own:
- The dominant social network for film buffs, now at 23 million users—up 125% since we acquired it two years ago (Letterboxd)
- The top DJ software business (Serato)
- One of most popular methods for brewing coffee (AeroPress)
- The top interface design agency in the world (Metalab)
- Among many others
To put that valuation in context and contrast how differently public and private markets operate:
Beacon Software, a Toronto-based holding company that's made only a handful of acquisitions (and is rumored to be less than half our size), just raised $250M USD in the private market at a $1B USD ($1.4B CAD) valuation.
To be clear: this isn't to dunk on them—I think they're probably worth $1B and I hear they're smart guys—but to show how out of sync public market valuations can be.
All of this has left us scratching our heads.
But as Graham and Buffett remind us: in the short term, the stock market is a voting machine. In the long term, it's a weighing machine.
Eventually it will weigh what matters: the earnings we deliver over the coming decades.
Our job is to keep growing earnings so the weighing machine catches up.
Speaking of which, we recently filed our latest quarterly earnings report (Q3 2025):
- Revenue of $54.0 million ⬆️Up 16% year-over-year
- Recurring Revenue of $16.9 million ⬆️ Up 72% year-over-year
- Adjusted EBITDA of $10.1 million ⬆️Up 39% year-over-year
- Free Cash Flow of $15.1 million ⬆️Up $14.4M year-over-year
- Net Debt to Adjusted EBITDA of 2.3x ⬇️Down 23% year-over-year
We've been hoping Mr. Market would wake up and smell the AeroPress, and he finally seems to be catching on—our stock is up about 45% over the last three months.
Regardless of Mr. Market's moods, we'll keep doing what we do: buying wonderful businesses, running them well, and letting time do the heavy lifting.
We appreciate our shareholders for coming along for the ride and taking the time to understand our beloved platypus ❤️
*Fun Obligatory Legal Note (There’s more stuff below, keep reading!):
On a trailing twelve-month basis through Q3 2025, Tiny generated more than $200M in revenue, more than $65M in recurring revenue and more than $40M in Adjusted EBITDA. Recurring Revenue, Adjusted EBITDA, Free Cash Flow and Net Debt to Adjusted EBITDA are non-IFRS financial measures or non-IFRS ratios, do not have standardized meanings under IFRS and may not be comparable to similar measures of other issuers. For definitions, explanations and reconciliations to the most directly comparable IFRS measures, see “Non-IFRS Measures” in our Q3 2025 MD&A and our Q3 2025 results news release, each available on SEDAR+ and at investors.tiny.com. This letter is for information only and is not an offer to sell or a solicitation of an offer to buy any securities. Past share price performance is not necessarily indicative of future results. This letter contains ‘forward‑looking information’ about Tiny’s business and strategy, including statements about our acquisition approach, our ability to compound earnings over time and our long‑term outlook. Forward‑looking information is based on assumptions and is subject to risks and uncertainties that may cause actual results to differ materially. Important risk factors are described in our most recent Annual Information Form and in our Q3 2025 MD&A, both available on SEDAR+. We do not undertake to update forward‑looking information except as required by law.
Random Stuff:
- My favorite NPS (net promoter score) software, Delighted, just announced that they are shutting down. So our team at Kno just launched their own. It’s really good, and made especially for ecommerce. Check it out.
- The other day, I spoke at the UVic business school and this South American guy walked me to my car, peppering me with questions. He was an interesting guy—studying business and physics, with dreams of building quantum computers. As an aside, he mentioned his wife was trying to break into DJing.
I told him I'd listen to her stuff and share it with some friends who throw parties. I ended up really liking this mix she posted on YouTube. Check out DJ Inna Brik.
- I just discovered Emitt Rhodes. One of those one-hit wonder guys from the 60’s who could have been huge but never was. I love this song (Promises I’ve Made).
- Yoda for agency owners. My old pal Mark, who was employee #3 or so at Metalab and ran the business for over a decade, wrote a book about all the chaos and learnings from the early days. It’s really good, and he is awesome. If you own a services business, this one is for you.
- A quote that struck me:
“Until you make the unconscious conscious, it will direct your life and you will call it fate.”
–Carl Jung
Go to therapy! (Or ChatGPT)
That’s all for now…
-Andrew
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