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Masters in Business · Friday, August 7, 2026

Jack Raines Discusses Speculative SPAC Trading and Significant Loss

Jack Raines recounts his experience trading SPAC warrants during the pandemic, turning $6,000 into $150,000 and later $400,000. However, a speculative bet on a buy-now-pay-later company called Catapult led to a loss of $150,000 in a single day after missing earnings, highlighting the risks of overly concentrated trades.

tickerSPACpersonJack RainespersonMichael BurrypersonBill AckmanpersonShaquille O'NealpersonPaul RyanpersonDan SundheimcompanyUPScompanyDraftKingscompanyNicolacompanySquarecompanyAfterPaycompanyWayfaircompanyCatapultcompanyRobinhoodcompanyD1 CapitalcompanyMelvin CapitalcompanyAkalocompanyGameStopcompanyOpenDoor

The tape

3 quotes
And then I just kept rinting and repeating spack warrants, and like six months later, I got from six grand to one hundred and fifty grand, and I was like, this is so easy.
I did that like seven times in a row, and then I went from one fifty to four hundred and like I'd only risked on any given trade, like five percent of my portfolio, and they didn't all hit, but like enough did that it didn't matter.
And I I just aped into it with like three hundred I think I had like three hundred and thirty thousand dollars at that point. Just went all in and it started like inching down and spike back up leading up to earnings, like I had four different times I could have gone out with like a ten percent loss, and I was just like I was just pot committed to, like this is gonna be the millionaire trade.
Heard on Masters in Business — “Optimizing Life and Finances in Your Twenties with Jack Raines, published Friday, August 7, 2026. Heardvine summarizes and quotes with attribution and timestamps, and links to the original everywhere.
Transcribed via publisher transcript · $0.00
Jack Raines Discusses Speculative SPAC Trading and Significant Loss — Heardvine