Nearly every tech CEO I talk to right now is obsessed with two
things: AI and prediction markets. In that order, but barely.
Yesterday, I interviewed Substack CEO Chris Best about his new
integration with Polymarket, which he confirmed is the deepest
outside partnership Substack has ever done. It lets writers embed
live prediction market data directly into their posts, and
Polymarket has joined Substack’s ads beta by paying select
creators to include markets in their stories.
Best wouldn’t get into the financial details of the deal itself,
though sources tell me Polymarket has paid X and other similar
platforms for the same kind of exclusive partnerships. I pushed
Best on why he chose an exclusive with Polymarket over also
integrating with Kalshi. He deflected and said he wanted to find
a partnership that “worked really well.”
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What’s going on here is bigger than Substack. Prediction markets
are subsuming the internet, whether you like it or not. They’re
getting embedded into the surfaces where people already consume
news, opinion, and analysis. Despite the strong, negative
reaction many people have to what prediction markets represent, I
expect more integrations like the one Substack announced in the
coming weeks and months.
Best told me he’s a prediction market nerd who traces his
interest back to the sci-fi-adjacent fascination that’s long
animated a certain kind of tech founder. He pointed to two
moments that made it feel real for him: watching prediction
markets call election results faster than the New York Times
needle, and using Polymarket odds on the TikTok ban to make an
actual business decision about how Substack should prepare. “The
fact that I could see a market signal on, hey, there’s a
substantial chance that this event is gonna happen, and then
potentially change how you plan your business, felt very
powerful.”
There are real concerns here that Best acknowledged but didn’t
fully resolve. Prediction markets sound elegant in theory: the
wisdom of crowds, priced in real time. But as I told Best, the
two questions that matter most are who is on the other side of
the trade and how disputes get resolved. There’s also the bigger
societal issue of whether betting on everything is even a good
idea.
None of these issues are ironed out. Insider trading via
prediction markets feels rampant, and meaningful cases to hold
offenders accountable have yet to be filed. Polymarket
specifically has historically used a crypto-based resolution
mechanism, and credible research indicates significant token
concentration. That means the people who hold the most tokens can
effectively control outcomes. Best said he hadn’t gone deep on
the specifics there but agreed that “if they have a resolver that
doesn’t work, the market won’t work.”
What’s happening now is a land grab. The two main prediction
market companies, Polymarket and Kalshi, are racing to embed
themselves on every platform where people pay attention, and the
CEOs of these platforms are mostly willing to ablige because
they’re obsessed with what prediction markets represent. To this
tech leader class, the potentially negative ramifications of how
these markets actually work today are secondary to the long-term
value they’ll bring. As Best put it to me: “I’m a ship and find
out guy.”
Notion CEO Ivan Zhao this week on ACCESS
Thanks again to Ivan for coming on this week’s show.
Listen or watch wherever you get podcasts.
The art of scooping on TBPN
Thanks to John Coogan and Jordi Hays for having me live in the
TBPN Ultradome earlier today. We talked about how I approach
scoops, using AI, the state of tech media, prediction markets,
and a lot more.
This week in Sources
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