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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode of Noob School, we sit down with Jake Bennett (via Zoom), cofounder and Principal of Well Street Partners. You can find him on LinkedIn here: linkedin.com/in/jake-bennett314
Jake is a Virginia native whose journey spans systems engineering at West Point, five years of active duty in the U.S. Army (with assignments in Colorado, Oklahoma, and Afghanistan), and an MBA from Michigan Ross. After his service, he joined McKinsey’s Chicago office—leading operational transformations for lower/middle-market industrial firms and executing procurement strategies across industries.
Today, Jake and his cofounder are focused on acquiring, operating, and growing small and mid-market businesses through Well Street Partners. In this episode, we dig into:
How his systems engineering and military background shaped his leadership and operational mindset
What he learned at McKinsey and how that informs his approach to transformation and execution
The “what, why, and how” behind Well Street Partners – investment criteria, operations playbooks, and value creation Sales, execution, and building credibility in small / middle market businesses
Career transitions: how to lean into your strengths, navigate uncertainty, and build upward momentum
Whether you’re early in your career or plotting your next pivot, Jake offers a compelling blueprint at the intersection of operations, strategy, and mission-driven investing.
Get your sales in rhythm with The Sterling Method: https://SterlingSales.co
I'm going to be sharing my secrets on all my social channels, but if you want them all at your fingertips, start with my book, Sales for Noobs: https://amzn.to/3tiaxsL
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