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“Nothing educates the mind quite like a complete lighting of one’s capital on fire.”
— Maxine Minter

Alex Feldman is the founder of Tiger and Bear, an M&A advisory focused on tech and services businesses. Before that, he was Chief Strategy Officer and General Counsel at Amaysim, where he ran three acquisitions simultaneously during full lockdown in 2020 and 2021 to build a dominant player that was ultimately sold.

In this episode, Cheryl and Maxine unpack how to buy and sell businesses when the world is doing crazy stuff around you. Alex breaks down why today's volatility isn't actually that different from the GFC or COVID, why timing is the single most important variable in any deal, and what the SaaSpocalypse means for tech companies thinking about selling when their natural buyers are struggling.

You'll also hear why more than half of Tiger and Bear's recent deals involved European and Asian capital rather than American, why profitable venture-backed businesses are suddenly more attractive to strategics, and what happens when the IPO market disappears as an exit path. For founders who can't raise their next round, he offers blunt advice: never waste a crisis, cut costs to buy yourself runway, and remember that raising and selling are the same activity, you're just selling different amounts of shares.

Alex closes with his Big Cojones moment: putting every spare $500 into the stock market during the GFC with no idea where the bottom was, buying Macquarie Bank shares at $30 and riding them back up.

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