Co-Founder of Tiny

Victoria, British Columbia
Joined August 2013
“What work of genius has ever been composed on chamomile?” - Michael Pollan @michaelpollan
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winning arguments is rarely worth the effort
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Everyone I respect admits impostor syndrome. Those who don’t? Don’t leave them with the company credit card.
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Never trust a clean toolbox.
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"Travel agencies are dead" — everyone, 2004. They set an all-time revenue record. In 2024. "AI will replace everyone" — everyone, 2025. The obvious prediction is often wildly wrong. Technology rarely kills whole industries. It kills the average and sends their customers to the best.
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The more I talk to friends about AI, the more I'm convinced the world changes next year. Then I remember there's a guy at CERN who just smashed particles together at near light speed, and his group chat is just as certain physics changes everything. To a worm in a horseradish, the world is a horseradish.
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Best advice I ever got was "be wary of professional advice when it's good for the advisor." Anyway, my barber says I definitely need a haircut.
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“We must believe in luck, for how else can we explain the success of those we don’t like?” – Jean Cocteau
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I'm hosting an event 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 people 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 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. DM me if you're interested in joining :-)
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Everywhere you look: people stuck in the past, still arguing with ghosts. “If you don’t believe in ghosts, you’ve never been to a family reunion.” — Ashleigh Brilliant
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Munger’s bonus rule: don’t be stupid. “It is remarkable the advantage that some people have gained by trying hard not to be stupid rather than trying hard to be smart.”
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Seeking credit dulls the shine of the deed. If it needs your name on it, it probably wasn’t that selfless. — my sister
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Some of my worst decisions in life and business came after asking smart, well-meaning mentors for advice. Advice is often like being given the perfect recipe; but your pantry’s full of different ingredients. Different timing. Different team. Different tools. And once someone gives advice, they get invested in you following it. If you don’t, they think you didn’t listen. If you do, and it backfires; well, that’s on you. Stories, on the other hand, don’t come with strings. They let you hear what someone actually did, and figure out what fits your situation. Ask for stories.
"Don't ask for advice. Ask for stories." - @_Sparling_
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Chris Sparling retweeted
Excited to share Tiny's 2024 annual letter ahead of tomorrow’s Annual General Meeting. Over the past year, we've sprouted a few new grey hairs, but we’re stronger for them. It was a year of hard learned lessons, optimization, and compounding. Here’s the quick version: • 10-year CAGR: Revenue 37%, EBITDA 25% 📈 • Q4 Adjusted EBITDA jumped 38% QoQ as our cost-cutting program kicked in 💰 • Recurring revenue is up 4× since ’21, now $39M, expected to jump to $64-66M ARR with Serato integrated 🔁 • Paid down $24.5M of debt 🏦 • Closed a 66% stake in Serato for US $66M—expected to lift consolidated EBITDA ≈45% 🎶 • Tiny Fund fully invested, doing around $66M of revenue (+17% YoY) — sent $2.2M of distributions to HQ, with @Letterboxd users doubling to 20M, @AeroPress revenue up 120% since acquisition, Mateina w/ @huberman revenue up 100% YoY rolling out to all Whole Foods locations in the USA 🔥 • Cut >$4M in annual overhead and exited two non-core agencies (8020 & Frosty) • Three tuck-in deals — Repeat, MediaNet, WholesalePet—plus a booming organic deal pipeline ✅ We’ll livestream the AGM on YouTube at 11AM PST tomorrow (June 5). Link to Annual Letter: drive.google.com/file/d/1Q2L… AGM YouTube stream: youtube.com/watch?v=GIF73qK4… To attend in person in Victoria, grab a ticket here: eventbrite.ca/e/tiny-agm-202…
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I'm excited to finally pull back the curtain and reveal what's been happening within Tiny's $150M Black Box 🪄📦 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 the entire fund. 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 $38M of our own capital into the fund, which was owned by the public company but didn’t share its numbers. People didn't get it: why did our acquired earnings stop growing? Had we lost our mojo? The short answer was that we were in a flurry of compounding, but it was all just happening inside this fund, creating a sort of financial "black box" that was impossible to understand from the outside. Here's how it works: Tiny Ltd ($TINY.V - our 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, we just released our Q1 results: • 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 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 $64-66 million. More details on our deal to buy Serato, the world's top DJ software company, here: xitter.cf/awilkinson/status/1906… If you want to dig into the details for Q1, check out the full earnings release. PS: Tiny's Annual General Meeting is coming up in a few weeks. I'd love to see you there! It’ll be Chris, Jordan, and me up on a podium doing Q&A. You can ask us about anything you want. It’s June 5th at 11:00 AM PT at the Fairmont Empress in Victoria, BC. I'll share the link to register below 👇
Huge news: We just bought a majority stake in Serato, the leading DJ software company. If you've ever been to a club, festival, or wedding reception in the last couple decades, you've likely danced to music played using Serato. It's the gold standard for DJs, from the unknowns in their dorm room to huge artists like Diplo. If you’re scratching your head wondering why Serato sounds so familiar, here’s a few places you might recognize it from: "You ain't got no fuckin' Yeezy in your Serato?" –Kanye West, "Dark Fantasy" "Serato spinning while I'm dropping these verses" –Kendrick Lamar, "ELEMENT." "Run through Serato like a marathon" –Jay Z, "Holy Grail" I used to be a (very bad) DJ in my twenties (my DJ name was DJFKFC 🤦‍♂️) so this is a particularly exciting acquisition for me. Fortunately for Tiny and our investors, this is far from a nostalgic vanity purchase. The business is remarkable: 🇳🇿 A 25 year track record of consistent growth, bootstrapped in New Zealand 📈 35% compound annual growth rate on recurring revenue over the last five years 👥 Over 2 million users worldwide 💰 Impressive profitability with 34% EBITDA margins 🎹 Deep integration with the best DJ hardware manufacturers For those of you that are Tiny ($Tiny.v) shareholders: 💸 The acquisition boosts Tiny's ARR by about 68% to between $64-66 million 📊 Increases our Adjusted EBITDA by approximately 45% Serato is exactly the kind of business we love: a category-defining brand with a deeply passionate user base and long runway ahead. The founders and team in Auckland have built something truly special over 25 years, and I'm thrilled they chose us as their long-term home. A warm welcome to AJ, Steve, Young, and the entire Serato team. We couldn't be more excited to have you join the Tiny family and we're looking forward to helping you take it to the next level. PS: As part of this announcement, Tiny also just announced strong Q4 results. You can check out the results and all the details on the acquisition in the full press release.
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Chris Sparling retweeted
Napoleon's definiton of a military genius was "The man who can do the average thing when everyone else around him is losing his mind." Same in investing.
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Just because you see the future doesn’t mean you’re close to it. “Never mistake a clear view for a short distance.” – Paul Saffo Hardest lesson for impatient people
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Chris Sparling retweeted
Charlie Munger: "There will never be any shortage of good people in the world. All you've got to do is seek them out and get as many of them as possible into your life. And keep the rest the hell out."
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Chris Sparling retweeted
Never forget that for every Jeff Bezos, who makes it, there are 10,000 Jeff Bozos who don't.
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Chris Sparling retweeted
Andrew Mellon has one of the most incredible stories ever. + He competed with Rockefeller AND won. + He gave up a fortune to become Treasury Secretary. + He eliminated income tax for over 90% of people. + He put tariffs in place. (Same playbook today) + He put the US in the best financial shape in history. + He warned about the speculative excesses of the late 1920s. No one listened. + When the crash came, he was one of the few who took advantage of it. Then, he pushed his advantage too far ...
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