Buy Now Pay Maybe: product as performance art

Welcome back to Not Fintech Investment Advice, where Simon Taylor and I do what we do best: talk about fintech startups we’re absolutely not giving investment advice on.

First up is Kairos, a multi-prediction market trading platform giving traders a single terminal to buy and sell event contracts across Kalshi, Polymarket, and all the other emerging platforms. Their pitch: what the Bloomberg terminal did for Wall Street, Kairos does for prediction market traders. That tees up our bigger idea: as prediction markets expand, how they get liquidity (especially through sports betting) shapes what these markets can become.

Next is Vault, which takes a different angle on crypto-collateralized lending. Instead of the usual over-collateralized “borrow to buy more crypto” model, Vault’s idea is infrastructure that lets lenders use crypto as collateral to improve pricing or unlock access for other loans. Banks may want this, but they have no ability to take custody of that crypto asset as a part of the collateral process, and monitor the value of it – all of the infrastructure is missing there.

Then there's Vennre, a wealth platform for high earners (HENRYs), offering private market exposure across real estate, credit, private equity, and venture through a mobile app with 1:1 financial coaches working with AI. Simon points out they’re registered in the UK and Saudi Arabia, Sharia-compliant, and targeting a growing cross-border audience tied to migration and real estate purchases.

Finally, we close with Buy Now Pay Maybe, an on-chain “buy now pay later” send-up (more product idea than actual company), where you can pay more for higher odds of getting the item for free, or lose and overpay. Simon frames it as performance art that points at something ugly, which we explore.

This episode is brought to you by Plaid. 

Plaid helps lenders approve more creditworthy borrowers without taking on more risk, combining real-time cash flow data with behavioral insights. It’s a fast, familiar experience people trust, and that actually converts. Learn more at www.plaid.com/ftt

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Companies featured:

https://kairos.trade/

https://www.collateralvault.com/

https://vennre.com/

https://merch.smallbrain.xyz/