Top of mind, inevitably, was last week's implosion of FTX, as O'Leary was a spokesperson and investor with the exchange.
It was our third conversation together, and O'Leary shared candid thoughts on his FTX investments going to zero, as well as details from a phone call he had with Sam Bankman-Fried just before FTX declared bankruptcy.
O'Leary, a paid spokesperson for FTX, said he had initially gained trust in the company and its 30-year-old CEO, Sam Bankman-Fried, a little over two years ago.
The Shark Tank star told me that he was on the phone with Sam Bankman-Fried the day before FTX declared bankruptcy to discuss a price for potential buyers to rescue FTX.
"He confirmed that it was $8 billion, and that's the number I took forward," O'Leary explained.