I own a misunderstood platypus…

Hello friend,

Here's what I'm thinking about…

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...

Read the full essay →

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.

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. 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.
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. We booked him without a thought, and I had no idea what to expect. 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. 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. The OG Othership is in Toronto, but he just opened new locations in Brooklyn and Manhattan.

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. You should go to a show.

4. Gillian Liu — 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. If you like having beautiful skin, you should visit Kiyoko and stock up.

5. Josh Franklin — Two guys had taken over a former grocery store and built a makeshift nightclub —the type you'd typically find in Williamsburg, not 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.

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

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.

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. 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