25b6

Track #1: Jeff Allen – From 12-Year Insider to Day One Outsider

Sep 10, 2025 / Loading...
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Jeff Allen, CEO at OuterBox, gets real about the messy truth of leadership transitions—the trust you have to rebuild from scratch, the pitches that go sideways in unexpected ways, and why putting your team’s wins before your own ego actually works. No corporate fluff, just the unvarnished stories that shaped his career.

What you’ll get:
-Why new leadership is basically starting over (even when you think it isn’t) 
-The pitch moment that defied expectations—and still led to success
-How to win by making other people look good 
-Real talk for young professionals trying to break through

Less LinkedIn motivation, more honest conversation about what actually happens when you’re figuring it out as you go.

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Creators and Guests

Host

Tom Hootman


CEO/Founder of Mixtape Digital

Guest

Jeff Allen


CEO of OuterBox

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