Hello, {{hc_sub_firstname | friend}}! Param here.

Look – every profile in this series so far has been a success story. Permanent Equity is debt-free and compounding quietly. Constellation's put up something like 26% a year for two decades. Berkshire is the whole template everyone's borrowing from, including us. Same idea every time: buy durable businesses, hold them forever, and let compounding do what compounding does.

This one's different, and honestly, I think it's the more useful profile of the bunch.

Tiny Ltd. ran the exact same playbook – same language, even – "The Berkshire of the Internet." Permanent hold. Leave the founders alone. And then it did two things none of the others did: it took on real debt, and it went public. 

Within a couple of years of listing, the stock was down close to 90% from its debut, by some measures, and the company was sitting across the table from its own lender renegotiating covenants.

And yet, here's the thing: Tiny's still standing. It still owns 21 companies, including Dribbble, AeroPress, Letterboxd. Recurring revenue was still growing 80% a year as of early 2026. In May 2026 they brought in a new CEO and kept grinding the balance sheet down.

So here's the thesis, up front, because I don't want to bury it: I don’t think the businesses fell 90%. From my POV, the structure is what fell apart. 

In 2006, Andrew Wilkinson was 19 years old and started a design agency in Victoria, British Columbia, called MetaLab. Year one, he did $250,000 in revenue at something like a 50% margin – I'm gonna fumble on the exact number, but the point is that it was a real business from day one, not a science project. Chris Sparling joined in 2009 to run finance, and by 2013, MetaLab and its sister companies were clearing roughly $7 million a year in combined profit.

That's when Wilkinson had his moment. He'd been reading the value-investing guys, and the realization was simple: stop starting businesses, start buying the ones that already work, and hold them forever. That's the whole Berkshire insight, just moved onto the internet. Tiny ran on nothing but that cash flow for years: no outside capital, no investors to answer to. A clean start.

The trouble came later, not at the founding.

Here's what Tiny actually buys: "profitable, simple, and often boring" internet businesses. High margins, low headcount, a real moat – a brand, a community, a niche nobody else wants. The portfolio grew past 40 companies (by some counts more than 80): Dribbble, Creative Market, AeroPress (yes, the coffee maker), Letterboxd, Serato.

And the edge wasn't valuation genius… It was speed. Wilkinson built a reputation for turning around an offer in 24 to 48 hours, light diligence, founder-friendly terms – sometimes buying half the company so the founder could take some money off the table and keep running the thing. If you're a founder dreading a six-month private-equity process with a hundred-item data room, that speed is the whole pitch, right?

Once they bought a business, they left it alone. No forced integration, no central playbook getting imposed from head office. Some portfolio CEOs reportedly go months without a call from Wilkinson. That's the same trust-the-operator instinct we lean on at Lynnfield – you find the right manager, and then you get out of the way.

On paper, this is everything this newsletter admires… so what actually went wrong?

The assets held up fine. Dribbble – bought for somewhere between $5 million and $10 million – now generates tens of millions in revenue on its own, which is a genuinely great return on a simple, community-moated business. Several other holdings are excellent, high-margin, recurring businesses, and that quality is exactly what carried the company through everything I'm about to describe.

Let’s take the leverage first. Unlike Permanent Equity or Constellation, which both run with little or modest debt, Tiny borrowed significant loans to fund growth. And here's the problem with that, at the end of the day: a permanent-hold thesis and a loan covenant just don't coexist well. You can plan to hold something forever, but a covenant date doesn't care about your plans – it can force your hand regardless. 

Then, in early 2023, Tiny went public through a reverse merger with WeCommerce Holdings – a Shopify-app roll-up that was originally backed by Bill Ackman and Howard Marks. The deal valued Tiny around $691 million and WeCommerce around $220 million. Two things compounded from there: WeCommerce's businesses were more cyclical than Tiny's core holdings, which diluted the quality of the combined portfolio, and, more importantly, a permanent-hold company full of hard-to-value private businesses is just an awkward fit for a public market that wants quarterly clarity.

Investors want a number every ninety days. Tiny's model doesn't really produce one cleanly.

By June 2024, Tiny had to amend its loan covenants with National Bank of Canada and commit to de-levering significantly – the classic signal that the balance sheet had gotten ahead of the cash flows. 

To his credit, and I mean this, Wilkinson's been candid about everything that went wrong over the years. His 2024 memoir, Never Enough: From Barista to Billionaire, is partly a reckoning with what the chase cost him personally, not just financially. 

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Here's the part most coverage skips, and it's honestly the most interesting piece of the whole story. In 2020, Wilkinson and Sparling raised their first outside capital – a $147 million fund. From 2021 through 2024, nearly every acquisition ran through that fund, not through the parent company.

Tiny owns about 20% of the fund and earns 30% carry above an 8% preferred return. But here's the wrinkle: none of the fund's results consolidate into Tiny's public financials. For years, if you were a public shareholder, all you could see was a $38 million line item on the balance sheet. Meanwhile the fund itself quietly generated $66 million of revenue in 2024, up 19%.

So there were effectively two Tinys. The leveraged public company everyone could see, and a healthier private fund almost nobody could.

Permanent-hold philosophy and an outside-money fund pull against each other structurally – funds come with carry hurdles and reporting clocks that fight "hold forever," even when the underlying businesses themselves are completely fine.

In May 2026, Tiny named Austin Singhera as CEO. Wilkinson moved to executive chairman, Sparling to executive vice-chairman. First-quarter 2026, in round numbers:

Wounded, not fatal. It’s clear that management's running an active deleveraging plan.

Tiny is somewhere mid-turnaround: it survived because the assets were good. And that, at the end of the day, is a completely different thing from compounding because the structure was sound.

At Lynnfield, we acquire cash-flowing businesses in the $1M–$10M EBITDA range and offer co-investment opportunities to qualified investors. Join our investor list to receive deal flow as we evaluate new acquisitions. 

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Tiny teaches permanent capital investors 4 essential lessons:

Thanks for reading!

Tiny is the most honest entry in this series of profiles, because it's the one that shows the permanent capital model has edges. As of 2026, Tiny is deleveraging, under new leadership, with its best businesses intact and a strategy that amounts to "keep the model, fix the structure."

Study Tiny the way pilots study near-misses – the instinct was right, the asset selection was right, and what nearly took the whole thing down had nothing to do with picking good businesses.

Talk soon,
Param

P.S. This is the fifth Investor Profile in an ongoing series on models of permanent capital. If you missed it, check out our previous editions.