From Military Service to Mission-Driven Business: How Jordie Kern Built 7 Eagle Group

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Jordie Kern, founder of 7 Eagle Group, to explore what it really takes to build and rebuild businesses from the ground up—seven times over. Jordie shares his 35-year entrepreneurial journey, the mindset behind mission-driven business, and how a simple one-minute video is transforming how military veterans connect with meaningful careers. This conversation dives deep into resilience, purpose, and practical business strategy, especially for founders building with limited resources but big vision. 🎧 What You’ll Learn in This Episode: How Jordie turned a mission to serve veterans into a 30-person recruiting company What the SkillBridge program is and how it supports both veterans and employers Why the traditional resume model is becoming outdated The most important hire to make when scaling a business How to think about funding without giving up equity Morning routines and time-blocking strategies from a serial entrepreneur Why your first business should be designed to fail safely and teach quickly ⏱️ Episode Timestamps: 00:04 – Welcome & intro to Jordie Kern and 7 Eagle Group 00:49 – Growing up as the son of a WWII Army veteran 04:21 – Early entrepreneurial ventures and working with the Clemente family 07:23 – The moment Jordie started 7 Eagle Group 10:06 – The reality of building the business from scratch 12:48 – How the SkillBridge program works 23:50 – The one-minute veteran video and why it works 30:15 – Scaling a remote team of 30+ 34:50 – Bootstrapping vs. investors 36:35 – Systems, delegation, and protecting your genius zone 43:50 – Advice for mission-driven entrepreneurs 46:42 – What “Do Small Business Like a Big Boss” means to Jordie 👤 About the Guest: Jordie Kern is the founder of 7 Eagle Group, a mission-driven talent platform based in Amherst, Massachusetts that connects military veterans and transitioning service members with meaningful civilian careers. With over 35 years of entrepreneurship experience and seven businesses built, Jordie has grown 7 Eagle Group into a fully remote team serving 125+ SkillBridge participants daily through its career academy. The company partners with major organizations including Amazon, the Kansas City Chiefs, American Airlines, and Jack Daniel’s. Connect with Jordie: Website: 7eagle.com Email: [email protected] 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training 👉 Grab your FREE Legal Guide at: https://www.smallbizzlegalguide.com 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC