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…
- A few months ago, this guy from the Netherlands emailed me asking if I'd come on his podcast.
Ughhhh.
I didn't want to do the interview, but I'm also bad at saying no.
Being my avoidant self, I used a tried but true line:
"Sure, but I'll only do it in person in Victoria."
That’ll get rid of him, I thought. Nobody ever wants to fly to Victoria.
Well, the son of a bitch called my bluff.
He flew 12 hours, mic in hand, and booked a podcast studio and everything.
Fortunately, he was a great guy and we hit it off. The interview was a blast and it turned out to be one of my all-time favorite interviews.
Well played, Wouter… Never underestimate a Dutchman.
We talk about:
- Challenging the negative view of "lifestyle businesses" and finding a third path that improves your life without artificial limitations
- How I build a community of interesting people through hosting events, forum groups, and Jeffersonian conversations
- Why the best business acquisitions come through personal connections, and how to create deal structures that make every stakeholder walk away happy
- Plus a ton more (it’s 2.5 hours)
Check out the episode on YouTube or Spotify.
You should also subscribe to Wouter’s newly launched podcast. He just did a great interview with the founder of Ramp.
- Every time I delegate a task to my assistants, there's a brief glimmer of hope.
This time, maybe this time, they'll remember to do it exactly the way I want.
Don’t get me wrong. My assistants Tina and Karen are amazing. But they’re only human.
And humans being humans, they get distracted. Things get busy. My travel schedule gets crazy. We host an event. Before I know it, their attention moves elsewhere and my inbox starts to get messy again.
And no matter how many admin people we hire, the same thing always seems to happen. Parkinson's Law kicks in:
“Work expands so as to fill the resources available for its completion.”
So, I finally gave up on humans for these sorts of rote tasks. I freed my assistants to focus on the high level stuff and built a robot to tackle my email.
Lately, I’ve been obsessed with this tool called Lindy that lets you create AI assistants. With it, you can make your own digital Rube Goldberg machines to complete almost any digital task, hooking up AI models to all the services you use (Gmail, Google Drive, Twilio, HubSpot—you name it) and having AI do things on your behalf. This could be as simple as sending you a text with a brief on the person you’re about to meet, or as complex as a 20-step automation that writes email newsletters for you (don’t worry, I wrote this by hand).
Last month, I built an automation that triages my email better than any human assistant ever could.
Every incoming email gets read by an AI agent that asks one question: "Does Andrew actually need to see this?" If no (about 80% of emails), it gets archived instantly.
Gone. Finished. Never appears in my inbox.
For emails I do need to see, it applies a label: Logistics, Kids, Events, Homes, Book, whatever.
Then it does all sorts of magical stuff:
- Kid's school emails get auto-added to my calendar with reminders (permission slips, field trips, stuff I need to pack, etc)—this one is a total game changer
- Anything needing my signature gets sent to my legal counsel, receipts go to accounting
- When someone reaches out wanting to sell their company or offering an investment, the AI will actually do a quick background check - who is this person? Are they legit? Does this seem dubious? If yes, instant archive. If no, it gets flagged to me to respond.
- Does it seem time sensitive? If yes, it adds an ASAP flag.
- And a ton more
My inbox is the cleanest it's been in years and I’m adding to the automation daily. So. Freaking. Cool.
If you want to hear me nerd out about my entire setup, check out my recent Superhuman podcast interview.
- If you don’t remember, last month I started bragging about my friends.
This time, I want to take a minute to brag about my friend Janene Scordo.
I’ve never met anyone like her. She’s one of the most intensely driven and brutally honest people I know.
I liked her the moment we met: she has that rare and wonderful quality of blurting out the thing that everyone else is thinking but is too chicken to say. Flash forward years later and she’s often the first person to tell me when I’m doing something dumb. She’s true blue and one of my best friends.
In her twenties she worked in finance, but after leaving her job to have two kids, she was going stir crazy, languishing in 24/7 kid life. She kept talking my ear off about wanting to buy a business, so I introduced her to Sarah Hunter, a talented designer friend who wanted to sell her agency to start a new business.
Janene knew less than nothing about running a design agency. She’d never used Figma and didn’t even know what CSS was. But she immediately jumped in and bought it.
Since then, she has taken the business from a single employee to over a dozen, and grown revenue more than 5x, doing brand, web, and Shopify design and development for amazing companies like Left on Friday, WealthSimple, and our beloved AeroPress.
So, dear reader, I give you three tasks:
1. Janene is really cool. If you’re an entrepreneur based in Vancouver or Victoria, you should email her and get coffee.
2. You should hire her agency. They're awesome and do great work (Shopify, Webflow, and branding in particular).
3. She wants to buy another business. If you know of a great company that's doing between $250k and $1M of annual profit, email her at janene@shopwelldesign.com (she’s industry agnostic)
- Tiny's Invisible Growth Machine: The $150M Fund You Couldn't See
Back in 2020, we raised a $150M USD fund. Chris and I were vaguely terrified — it was the first time we'd ever raised outside capital, other than letting friends co-invest in a few deals — but it ended up being perfect timing.
From 2021-2024, almost all of our acquisitions happened in the fund. The additional capital allowed us to buy incredible businesses like AeroPress (the popular coffee maker) and Letterboxd (a social network for film buffs that just hit 20 million users). By late 2024, with those and a few other acquisitions, we'd fully deployed all $150M USD.
The problem? When we went public in 2023, this structure made it nearly impossible for our public company shareholders to understand what the hell we were up to. It looked like we stopped investing for three years, when in reality, we poured $38M of our own capital into the fund, which was owned by the public company but didn’t share its numbers. People didn't get it: why did our acquired earnings stop growing? Did we lose our mojo?
The short answer was that we were in a flurry of compounding, but it was all just happening inside this fund, creating a sort of financial "black box" that was impossible to understand from the outside.
Here's how it works: Tiny Ltd (the public holding company) owns about 20% of the fund, plus we get 30% of the profits after our investors hit an 8% annualized return (this is called "carry" in investor-speak). But none of the fund’s revenue or earnings shows up in our financial statements. The only thing an investor would see is a $38M investment on our balance sheet.
After over a year of back and forth and countless painstaking meetings with accountants, lawyers, and auditors, we can finally share some actual numbers (note: these figures are all unaudited):
- The fund generated $66M in revenue for 2024, up 19% from 2023
- In Q1 2025, it did $17M in revenue, up 13% from Q1 2024
- Tiny received $1M in distributions from the fund in Q1 2025
Before you break out the calculator: yes, that $1M is roughly 20% of the total distributions for the quarter, but also includes some of our carry. So you can do your own napkin math about how much cash these businesses are throwing off, but it won’t be perfectly accurate. Note: We're actively working on reporting more detailed fund metrics.
Going forward, the fund is wrapped and now it's just about seeing those investments through, capturing the upside, and cashflowing. All new acquisitions (like Serato, which I'll tell you more about in a moment) will happen directly in the public company, making everything much cleaner and easier to understand.
Along with the fund numbers, our Q1 results are in:
- Total revenue of $48.1 million, up 6% from Q1 2024
- Adjusted EBITDA of $9.7 million, up 63% from Q1 2024
- Net Debt to Adjusted EBITDA decreased from 3.0x to 2.7x
While our revenue growth is slightly muted due to headwinds in a few of our businesses, I’d like to highlight something we've been focusing on the last few years: replacing non-recurring revenue with highly predictable recurring revenue.
Take a look at how our revenue mix has been evolving:
- 2022: Total: $153.7M | Recurring: $8.9M (5.8%)
- 2023: Total: $185.5M | Recurring: $29.5M (15.9%)
- 2024: Total: $194.2M | Recurring: $38.7M (19.9%)
With the Serato deal now officially closed, that number is set to grow significantly once again. Serato adds roughly $26 million of annual recurring revenue, boosts our Adjusted EBITDA by approximately 45%, and contributes significantly to our top line. Importantly, it increases Tiny's Annual Recurring Revenue by about 68% to between $64-66 million.
If you want to dig into the details for Q1, check out the full earnings release.
Also, our annual general meeting is coming up in a few weeks. I'd love to see you there. It’ll be Chris, Jordan, and me up on a podium doing Q&A. You can ask us about anything you want.
It’s Thursday, June 5th at 11:00 AM PT at the Fairmont Empress in Victoria, BC. Click here to register
- For years I've been tearing my hair out dealing with Canadian banks for our credit cards.
This is how bad it is: years ago, at a time when Tiny was doing over $10 million EBITDA, one of the big national banks (I won't say who) wouldn't give us a credit card unless we put down a $50,000 deposit.
That is how backwards this stuff is. Not only that, but it took weeks and we had to sign a telephone book worth of documents with wet signatures.
Fortunately, this kafkaesque nightmare is over. There are finally some amazing options that you should switch your companies to:
Ramp - just launched in Canada(!)
Float
Venn
We use all three across various businesses and they are all great (with slightly different feature sets).
Random Stuff:
- I'm loving the new Lorne Michaels biography - It’s so good I find myself skipping all my favorite TV shows to read it every night. Aside from hearing all the saucy gossip and hilarious anecdotes about how he launched many of the world’s largest comedians (Mike Myers, Tina Fey, Bill Murray, Eddie Murphy, Will Ferrell, and dozens more), it’s a fascinating character study of a deeply complicated person. Bonus points: he's Canadian. Grab a copy here
- Listen to me and Sam Corcos jam about our favorite Life Hacks - Sam is the best sort of lunatic. He tracks his time in 15-minute blocks, shares his home with another couple even though he’s rich, and has been "news sober" for 11 years. We discuss how your calendar reveals your true priorities and why AI might create more software developers, not fewer. Lots of fun ideas in here. Spotify / YouTube
- We’re speaking in Victoria - Chris and I were flattered to receive UVic's Distinguished Entrepreneurs of the Year and there’s a big gala to celebrate on June 10th in Victoria. There will be a reception, dinner, and a fireside chat/Q&A. It’s usually a black tie event, but because we hate wearing suits, you can wear whatever you want. Grab tickets here
- There are only 10 spots left for Interesting People - This is the conference I wish existed when I was younger. No status games. No badge-glancing. Just 150 interesting people hanging out for 3 days. If you're a close friend and want to come, text me ASAP. Otherwise, apply here.
- We’re hiring an event coordinator - We’re looking for someone to help run my Interesting People event this July. You'll work with the team to handle all the ground-level details - food, venues, signs, transportation, guest needs. Perfect for someone who's run events before, communicates well under pressure, and knows Victoria. Ideally you're a foodie with great taste, love thoughtful design, know all the best spots in town, and thrive on details. Part-time leading up to the event, then all-in during. This could become a full-time role if it goes well, as we're now doing multiple events per year. Email monica@follypartners.com if this sounds like you (or you know someone).
- Buy my apartment - I bought this stunning penthouse apartment in Vancouver and had my friend Kate Snyder and her team at Studio Roslyn turn it into something amazing. Unfortunately, with our busy life in Victoria, Zoe and I barely used it, and our plans to Airbnb got kiboshed when Vancouver changed their short-term rental laws.
I bought it out of bankruptcy for $3.7M (the last sale was for well over $4M), and we recently listed it for $3.68M. It fully cash flows itself, but I don't like the logistics of managing real estate.
We ended up renting it to a wonderful elderly couple who are very happy there, and we don't want to move them, so our buyer has to be someone who wants to buy and hold a cash-flowing asset, with the possibility of potentially moving into it in the future.
Also: if you own an exceptional, cash flowing business, perhaps I could be persuaded to trade the apartment for equity ;-)
If anyone wants to buy a beautiful cash-flowing penthouse in Vancouver, check it out.
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.
