Hey y’all — founders can’t afford to trust conventional wisdom too much.

We have to look for opportunities to be contrarian… and right.

LLMs have created many new markets and also re-opened some that VCs previously thought were capped.

Dating is the perfect example.

Conventional wisdom would’ve told Keeper.ai’s (full disclosure: I invested in their pre-seed) founders to go after a market that sees larger outcome potential (most dating app acquisitions don’t disclose the price, for a reason, and even Bumble’s stock has dropped 90% since its IPO)… even though it’s one that’s so obviously broken.

Those disappointing (in venture terms) outcomes aren’t a sign that dating can’t be a venture-scale market, instead they’re precisely the reason the market requires a radically new way of thinking about it.

So, instead, Keeper’s built an incentive-aligned business (users only pay if they get into a long term relationship) that leverages LLMs to take the best parts of dating apps (scale) and matchmakers (precision) to build something that could not have ever existed before.

I sat down with Keeper.ai’s founders to talk about:

Match Group, the holding company originally behind legacy dating website match.com, acquires most dating apps before they reach true venture scale.

It’s actually crazy. Their assets do a combined $3.3B of the roughly $6B in revenue in the entire dating market each year. One company owns more than half the market. Literally.

Acquisitions aren’t just a good and defensible strategy for them, they also tend to be good for the founders who built an upstart / niche dating app once they realize they aren’t going to be able to reach venture scale in the first place.

So even though market is, in theory, giant since it includes every person on earth it’s never been loved by VCs and has only achieved $6B in total annual revenue after decades.

To me, a radically new approach seems like the only way forward.

Despite the broken market, meeting people through apps has quickly become the most common way to do so.

Within the “met online” category there are really two options:

Apps have solved the scale problem. Their pitch is that instead of just having access to whoever happens to be around the proximity of your life, you get access to thousands or millions of potential matches. However, they want to get you swiping and using the app so their filtering system is very imprecise. A few surface-level questions and you’re off to the races).

Also, most people are too selective on dating apps in the first place even with the minimal amount of questions they ask — Keeper built a fun tool to show you the actual amount of people who fit your dating preferences so you can see how large the pool you’re going after actually is.

Matchmakers have the opposite setup: they get to know you really well, but can realistically only work with a small handful of people at a time (even counting their “databases”).

Why I liked Keeper from the moment I first heard about it (aside from the fact that they fit my arbiter thesis perfectly) is because they’re using LLMs to get the best of both worlds, without the downsides.

They can have the scale of a dating app (and have already had over a million organic signups) but know you as well as (if not better than) a matchmaker, with an onboarding process that is intentionally high-friction.

It took me 45 minutes or so, but that didn’t stop me because I knew the offer they were making of scale + precision was the most compelling option that, for them, has led to 1 in 10 first dates leading to a marriage. That’s a lot better than Tinder’s 1 in 100,000.

Right now we’re all in search of defensible models.

Keeper’s got it figured out. Existing dating apps simply cannot compete on the one metric that matters most, helping people find lasting relationships, because their business model is built on the opposite incentive.

Traditional apps run on subscriptions + in-app purchases. Its their goal to keep you subscribed, not churning. The matches need to be good, but not so good you go off the app.

If Tinder switched to Keeper’s outcome-based pricing model, their ARR would crater overnight. It’s so big of a bet for them to make that the risk is too high for a business of their size.

Keeper’s using incentive-alignment as an uncopyable moat. They weren’t concerned with building a better algorithm, they built a company whose success is tied to that of their users while incumbents are trapped by their own economics.

I’ve been keen to share Keeper’s story because it’s a reminder to all founders that being contrarian and right is not only possible, it creates defensible models that can unlock larger TAMs than are accessible to everyone else.

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