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GRPN is my biggest holding. I think they are pulling off one of the best business turnarounds we have seen in the past decade and the market is dead asleep on it. Am I regarded? Read and decide for yourself.
My bull case has three legs: a platform with massive room to improve (top line), an operation with massive room to streamline (bottom line), and a stock under extraordinary short pressure (the squeeze fuel). Each one wins on its own. Together they’re stupid.
\*\*Basic facts\*\*
\\-Groupon returned to growth in 2025: global billings of $1.67B, up 7%, and free cash flow positive for the second straight year. Q1 2026 was a soft patch (revenue flat, billings down 1%, units down 5%), but that quarter predates both the restructuring and the platform rollout in its core market. That matters, hold the thought.
\\-16.2 million people actually buy on Groupon every year (active customers, real billings, not site visitors), up 5% year over year.
\\-But each of those customers only buys about twice a year. Annualized units run around 32 to 35 million against 16.2 million customers, so roughly 2 purchases per customer per year, and that frequency is currently falling, not rising. That is the single biggest lever in this entire thesis, and I’ll explain why in a second.
\\-Roughly 1,700 employees plus several hundred contractors. They just cut up to 400 roles (employees and contractors), which the company itself frames as about 15% of global headcount, as the first wave of a multi-tranche AI efficiency program called Project Foundry. First targets are customer service and HR. IT, finance, and marketing come later.
\*\*Leg 1: The platform (the top-line lever)\*\*
Do yourself a favor and pull up groupon.com right now. Outdated? Yes. Kind of ugly? Yes. User friendly? No. Recommendation algorithm? Terrible. So ask yourself why 16.2 million people still buy from it every single year.
The answer is a genuinely strong brand moat and an unmatched scale of local offerings. That keeps Groupon on top despite a product nobody has loved in years.
Here is the opportunity. Groupon’s core user is older, lower to middle income, and deeply discount savvy. But younger lower to middle income people are struggling financially at levels we have not seen in a long time, and they are every bit as discount savvy as their parents are. The only thing missing is that Groupon lacks the flavor and the user experience of the discount apps young people actually use. Management knows this, and fixing the UI/UX and the recommendation engine is now the number one platform priority. A better product means a bigger addressable demographic (more users) and more purchases per user (higher frequency). Frequency is the one that really matters, because incremental purchases fall almost straight to the bottom line.
And this is not hypothetical. The new consumer platform is already live internationally, and in Q1 2026 International Local Revenue grew 19% (excluding Giftcloud) on the back of it. North America, the bigger and more important market, has barely started migrating (about half of NA iOS users as of Q4 2025). So the platform catalyst is already proven in one market and is only now rolling into the larger one. That is the cleanest tell you will get that this works.
On top of the operating story there is a one-time windfall coming. Groupon owns roughly a 2.3% stake in SumUp, a European payments company reportedly preparing an IPO that could value it around $10B to $15B. At that range the stake is worth somewhere in the low to mid hundreds of millions gross, though lockups mean not all of it turns into cash on day one. Even a conservative realization is well above the roughly $75M the stake is carried at on the books, so it is almost pure upside the market is not pricing. Whenever it lands, it further fortifies a stabilizing balance sheet and hands management more ammo.
\*\*Leg 2: Operations (the bottom-line lever)\*\*
Groupon’s headcount has always been bloated, and this is the leg where they finally fix it for good.
Project Foundry is the next chapter, and AI is the tool. The plan is to embed AI agents into the core of every function, and then take headcount out as those agents absorb the work. Crucially, this is not a one-time slash. It is being run in tranches.
Wave one is the up to 400 roles already announced (about 15% of global headcount), with the majority done by the end of Q3 2026 and the rest extending into Q4 where local labor laws require consultation periods. The first functions on the block are customer service and HR, the most automatable layers, and they are leaning on contractors here, which is why the restructuring charge is small (only $7M to $13M, almost all severance) relative to the savings. That alone is guided to generate $20M to $25M in annualized payroll savings.
Wave two and beyond is the part the market is not paying for yet. Management has explicitly said it is evaluating further material cost-reduction and automation actions under Project Foundry, with those expected to run through the end of 2027. That is where the remaining merchant rep layer, IT, finance, and marketing come into play, the bigger and more expensive SG&A functions. Wave one is the cheap, contractor-heavy proof of concept. The real margin unlock is the employee-side automation still ahead.
And this is not a company swinging the axe blindly to juice one quarter. They are reinvesting up to half of the savings back into marketing, AI infrastructure, and talent density, so this is a reallocation from low-value manual labor into the growth engine, not pure cost-cutting. They have also done exactly this kind of painful headcount reduction before. A decade ago, before they built the self-serve merchant portal, they needed reps to service basically their entire merchant base, and they cut that down massively. This is a management team that knows how to take a company leaner and come out better for it.
The result already shows in guidance. Management raised full-year 2026 adjusted EBITDA guidance to $75M to $80M on the back of these actions, and full-year free cash flow is guided to at least $60M. On a roughly $625M market cap, that is around a 10% free cash flow yield on guidance, for a company the market has basically left for dead.
\*\*Leg 3: The stock (the squeeze fuel)\*\*
This is where it gets fun.
\\-Short interest is extreme. Depending on the source it runs roughly 50% to 60% of float (Quiver had it at 61% in May), among the highest of any US listed stock, with around 11 days to cover. And that is the polite version. A large block of shares is locked up with Pale Fire Capital (the CEO’s firm, now the controlling shareholder) and other insiders, so against the shares that can actually be borrowed and traded, effective short interest is dramatically higher, plausibly near or above 100%. That is a powder keg.
\\-The board authorized up to $300M in buybacks and is actually executing: $21.3M in Q1, another $10.1M in April alone, with about $215M still left. That remaining authorization by itself is roughly a third of the entire market cap. Every share they retire shrinks an already tiny tradeable float, straight into the teeth of that short interest.
\\-Add the eventual SumUp cash and you have a fortified balance sheet with real optionality: more buybacks, more platform investment, or worst case more strategic investments.
\*\*The obvious bear arguments, addressed\*\*
\\-“Negative equity, it’s basically insolvent.” No. The equity deficit is an accounting artifact of the buybacks (treasury stock) and convertible note math, not an operating problem. They hold $225.5M in cash against roughly $290M of converts, generate positive free cash flow, and have the SumUp asset sitting on top. The 2023 going-concern scare is dead and buried.
\\-“Units are falling.” True right now, and that is exactly the point. Frequency is depressed because the product is dated. The entire platform thesis is about reversing that, and the international numbers say it is already reversing where the new product has actually shipped.
\\-“It’s not dirt cheap anymore.” At roughly 7.5x EBITDA it is not a cigar butt. But it is nowhere near priced for a successful AI-native turnaround plus a SumUp windfall plus a short squeeze.
\*\*Alignment\*\*
The CEO runs Pale Fire Capital, the controlling shareholder, owns about 3% directly, and insiders have been net buyers (over $1M in the last year). They formed a board-level AI committee in March 2026. The people steering this have their own money in the seat right next to yours.
\*\*Bottom line\*\*
Improving product (more users, more frequency) plus AI-driven cost cuts (fatter margins) plus a $300M buyback chewing through a tiny float that is shorted into the ground plus a SumUp cash windfall. Three independent ways to win, on a stock the market has written off. I’m long, it’s my biggest position, and I’m not trimming.