Annanay Kapila - Former quant on why Hims is the most-shorted stock in the S&P MidCap 400 🤯

In Hims House episode 57, former quant Annanay Kapila (ex–Tower Research, Cambridge math) breaks down how high-frequency trading actually works and why retail investors shouldn't try to beat HFT firms at their own game. He breaks down QFEX, his new 24/7 exchange built with crypto-style efficiency for traditional markets, and the core case for nonstop trading. The conversation then turns to Hims' extraordinary short interest — roughly 76 million shares, around 44% of float — with Annanay pointing out that theoretically much of it *could* stem from long/short hedge fund mandates, risk-model offsets, and institutional groupthink rather than fundamental bets against the business. They also unpack what large disclosed stakes from firms like Jane Street and JP Morgan actually signal. The episode closes on Annanay’s essay “Prediction Market Paradox” - a dimmer view on prediction markets.

00:00 Sponsor: Mochi Health

02:10 High-frequency trading

03:59 Background of a quant

12:47 Why Annanay left Tower to build QFEX

15:28 The case for 24/7 trading

18:56 Does HFT “rig” the market?

25:45 Why Is Hims so heavily shorted?

34:25 How to read short disclosures correctly

37:14 What might trigger shorts to cover?

40:15 Hims down 17 out of 18 weeks 🤯

41:41 Convertible notes and the anti-squeeze

45:52 What a Jane Street stake really means

52:11 Prediction markets

Disclaimer: This podcast is for informational and entertainment purposes only. Nothing discussed should be considered financial, investment, or legal advice. Always consult with a qualified professional before making financial decisions.