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 companyWhat the SkillBridge program is and how it supports both veterans and employersWhy the traditional resume model is becoming outdatedThe most important hire to make when scaling a businessHow to think about funding without giving up equityMorning routines and time-blocking strategies from a serial entrepreneurWhy your first business should be designed to fail safely and teach quickly⏱️ Episode Timestamps:00:04 – Welcome & intro to Jordie Kern and 7 Eagle Group00:49 – Growing up as the son of a WWII Army veteran04:21 – Early entrepreneurial ventures and working with the Clemente family07:23 – The moment Jordie started 7 Eagle Group10:06 – The reality of building the business from scratch12:48 – How the SkillBridge program works23:50 – The one-minute veteran video and why it works30:15 – Scaling a remote team of 30+34:50 – Bootstrapping vs. investors36:35 – Systems, delegation, and protecting your genius zone43:50 – Advice for mission-driven entrepreneurs46:42 – 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.comEmail: jk@7eagle.com🚀 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