My son Jack Sterling returns to Noob School for his fourth appearance — officially becoming the most frequent guest on the show. This one dives deep into what Jack’s been up to lately — from his growing business, Cloud Hound, to his work with Upstate Warrior Solution helping veterans transition into entrepreneurship. We start off trading thoughts on our favorite podcasts and how shows like Lions Led by Donkeys and My First Million have influenced the way Jack thinks about leadership, learning, and risk-taking. Jack shares how fantasy football and analytics sparked his fascination with data — eventually leading him to pursue a master’s degree in data analytics at Clemson. But the heart of the episode is about purpose — how veterans can rediscover team, mission, and structure through entrepreneurship. Jack breaks down how his program at the Rupert Hughes Veteran Center supports veterans, first responders, and their families across the Upstate by helping them navigate healthcare, education, and business ownership. He shares inspiring success stories from entrepreneurs who’ve come through the program — from a veteran-run medical training company using human remains for realistic field instruction, to another launching Upstate South Carolina’s first paddle tennis facility. We also dig into the lessons he’s learned running Cloud Hound — from ditching international business to focusing on “cyber and fiber” solutions for local clients, and why most security breaches start with people, not technology. Jack explains his live training on social engineering, phishing, and why emotional manipulation is hackers’ easiest path in. To wrap it up, he shares the book that’s had the biggest impact on him — “Tribe” by Sebastian Junger — and why it reframed his entire view of community, fulfillment, and the difference between the military and civilian worlds. If you’ve ever wondered how to find purpose after leaving a structured environment, or how to turn your skills into impact, this one’s for you. 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 Subscribe to our newsletter today: https://bit.ly/3Ned5kL #SalesTraining #B2BSales #SalesExcellence #SalesStrategy #BusinessGrowth #SalesLeadership #SalesSuccess #SalesCoaching #SalesSkills #SalesInnovation #SalesTips #SalesPerformance #SalesTransformation #SalesTeamDevelopment #SalesMotivation #SalesEnablement #SalesGoals #SalesExpertise #SalesInsights #SalesTrends#salestrends

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

Subscribe to our newsletter today: https://bit.ly/3Ned5kL

#SalesTraining #B2BSales #SalesExcellence #SalesStrategy #BusinessGrowth #SalesLeadership #SalesSuccess #SalesCoaching #SalesSkills #SalesInnovation #SalesTips #SalesPerformance #SalesTransformation #SalesTeamDevelopment #SalesMotivation #SalesEnablement #SalesGoals #SalesExpertise #SalesInsights #SalesTrends#salestrends

When I sat down with Lamar Flatt — former Harvard basketball player, USC law graduate, and now partner at Best & Flatt, P.A. — I knew we’d cover a lot of ground. Lamar’s story takes him from the court to the courtroom, starting his law career in Savannah, GA, before returning to South Carolina, and he’s built a reputation as both a sharp attorney and a lifelong learner.

In our conversation, we talk about why curiosity matters, the importance of always seeking knowledge, and a perspective we discuss called “ant theory.” Imagine a closet that, to a colony of ants, is their entire world. They don’t realize there’s an entire house beyond it, or even more beyond the house. The same goes for us as humans: there’s always more to discover if we keep looking and keep learning.

Along the way, Lamar shares stories from his own path in law, how he approaches cases, and the mindset that’s carried him through challenges and opportunities. If you’re serious about growth, staying curious, and seeing the bigger picture in your own life and career, this episode will resonate.

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

Subscribe to our newsletter today: https://bit.ly/3Ned5kL

#SalesTraining #B2BSales #SalesExcellence #SalesStrategy #BusinessGrowth #SalesLeadership #SalesSuccess #SalesCoaching #SalesSkills #SalesInnovation #SalesTips #SalesPerformance #SalesTransformation #SalesTeamDevelopment #SalesMotivation #SalesEnablement #SalesGoals #SalesExpertise #SalesInsights #SalesTrends#salestrends