The AI secondary shares market is giving Beanie Babies economics

The Equity podcast crew is wrapping up another eventful week, with real estate, AI agents, gambling, and secondary markets — which are, of course, a form of legalized gambling. Mary Ann Azevedo, Becca Szkutak, and Devin Coldewey started off this Friday's episode with the acknowledgment that the X/Twitter ban situation in Brazil is possibly too complicated an issue to even have an opinion on. Let us cook on that for a bit. In the deals of the week, Devin first talked about You.com's $50 million play to take on more difficult AI tasks, things that can't be solved with a quick Google search. The company is hoping to be the go-to for complex stuff that mixes live search, coding, and natural language understanding — and unlike a lot of its competition, some of its customers actually pay for themselves! Becca, as someone who hazards a buck on a game now and then, is intrigued by DubClub, a startup that claims to systematize and legitimize professional betting handicappers. These are folks who claim to be able to beat the odds, but tend to offer their services by more informal methods. Can DubClub make a clean business out of this popular, but legally fraught, line of work? A 9-figure deal is always worth chatting about, and Mary Ann brings up Paylocity's acquisition of Airbase for $325 million — though, as she points out, the real value of the deal is probably considerably higher. It's a lot of money, yes, but compared with earlier valuations... no? Somehow we don't think founder Thejo Kote is shedding too many tears over it. Anyone who's bought a house or tried knows the sting of the realtor's fee. How many percent? Well, due to a recent court ruling overturning an established business practice in real estate, percentage fees may be on their way out — if startup Landian has its way. They want to make flat fees and pay-on-close the standard. Redfin is not amused! But they aren't mad either, or so they'd like us to think. Investing in AI is so popular people are investing in the investors investing in AI — on the secondary market, where positions on Anthropic, OpenAI, and xAI are now commanding a staggering 30% premium. That gives the actual equity holders a lot of leeway, and potentially gives smaller investors a chance to ride the hype train, but it also gives the whole thing the feel of, as Devin put it, "a beanie baby economy." That reference is just for the millennials as a "thank you" for listening.