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  Ashley Welch and her cofounder were finally in the room for the big break they d been working towards: a chance to pitch their tech startup to a prominent venture-capital investor. Though she was confident in her vision for the company, Welch was frustrated by her business partner s habit of talking over her. Suddenly, the investor they were pitching, Jason Calacanis, stopped the conversation. Who s the CEO? he wanted to know.  I am, Welch s partner responded without skipping a beat.  No, you re not,   Calacanis shot back. She s the CEO. Just like that, Welch was the CEO, and her startup, a dating app called Flutter, had a $25,000 investment and the promise of at least another $25,000 to come. The quick-fire decision was classic Calacanis, in keeping with a blunt, gut-driven style that sets him apart from his peers.

New yorkUnited statesBay ridgeFordham universityTelegraph hillSan franciscoAshley welchKeith raboisChris harveyBlokable holmChesa boudinChamath palihapitiyaBrian alveyGavin newsomHoward sternOsmaan shah