Milpreneur | David Fivecoat | Pivoting From Combat to Consulting
Mon Jan 05 2026
In this episode of the Milpreneur Podcast, Ryan sits down with David Fivecoat, a retired Army Colonel and the founder of The Fivecoat Consulting Group (TFCG). David shares his incredible journey from West Point and leading troops in the 101st and 82nd Airborne Divisions to navigating the civilian corporate world. He opens up about the harsh reality of launching his own consulting firm in March 2020—right at the start of the global pandemic—and the grit required to survive those early, lean quarters.
David provides a masterclass on adaptability, discussing how he pivoted his business model from general consulting to offering unique "Leadership Experiences" on historic battlefields like Gettysburg and Normandy. Whether you are a service member looking to transition, a solopreneur struggling with marketing attribution, or a leader trying to scale your impact, David’s insights on resilience, the importance of gaining civilian experience before hanging your own shingle, and prioritizing personal health are invaluable.
In this episode, you will learn:
• The "Gap Year" Strategy: Why working for an established company before starting your own business can provide the essential systems and processes knowledge needed for success.
• Surviving a Crisis Launch: Real-world lessons on resilience and perseverance when launching a startup during an economic downturn or global crisis.
• The Power of the Pivot: How to recognize when your business needs to evolve (TFCG 2.0) and the success found in specializing—in this case, corporate staff rides and battlefield tours.
• Marketing for Solopreneurs: The challenges of attribution in a multi-channel world and why "spinning the plates" of business development, execution, and marketing is a constant balancing act.
• Leadership & Self-Care: Why "the grind" isn't always the answer—David explains why getting enough sleep is crucial for effective leadership and long-term endurance.
About David Fivecoat:
David Fivecoat is the Managing Member of The Fivecoat Consulting Group. A retired Army Colonel with 24 years of service, including command of the Airborne and Ranger Training Brigade, David now helps executives and organizations build resilience and leadership through executive coaching and immersive battlefield leadership experiences.
Connect with David Fivecoat & Cynergists
David's Website: http://thefivecoatconsultinggroup.com
Cynergists: http://www.cynergists.com
Chapters:
00:00 - Intro
1:05 - David's Military Background & Career
04:10 - Transition Advice: Get Corporate Experience First
06:30 - Launching a Business in March 2020
08:25 - TFCG 2.0: Pivoting to Battlefield Tours
10:45 - The Solopreneur Marketing Struggle
13:30 - Rapid Fire Questions
17:35 - Advice to Younger Self: Prioritize Sleep!
19:58 - Outro
More
In this episode of the Milpreneur Podcast, Ryan sits down with David Fivecoat, a retired Army Colonel and the founder of The Fivecoat Consulting Group (TFCG). David shares his incredible journey from West Point and leading troops in the 101st and 82nd Airborne Divisions to navigating the civilian corporate world. He opens up about the harsh reality of launching his own consulting firm in March 2020—right at the start of the global pandemic—and the grit required to survive those early, lean quarters. David provides a masterclass on adaptability, discussing how he pivoted his business model from general consulting to offering unique "Leadership Experiences" on historic battlefields like Gettysburg and Normandy. Whether you are a service member looking to transition, a solopreneur struggling with marketing attribution, or a leader trying to scale your impact, David’s insights on resilience, the importance of gaining civilian experience before hanging your own shingle, and prioritizing personal health are invaluable. In this episode, you will learn: • The "Gap Year" Strategy: Why working for an established company before starting your own business can provide the essential systems and processes knowledge needed for success. • Surviving a Crisis Launch: Real-world lessons on resilience and perseverance when launching a startup during an economic downturn or global crisis. • The Power of the Pivot: How to recognize when your business needs to evolve (TFCG 2.0) and the success found in specializing—in this case, corporate staff rides and battlefield tours. • Marketing for Solopreneurs: The challenges of attribution in a multi-channel world and why "spinning the plates" of business development, execution, and marketing is a constant balancing act. • Leadership & Self-Care: Why "the grind" isn't always the answer—David explains why getting enough sleep is crucial for effective leadership and long-term endurance. About David Fivecoat: David Fivecoat is the Managing Member of The Fivecoat Consulting Group. A retired Army Colonel with 24 years of service, including command of the Airborne and Ranger Training Brigade, David now helps executives and organizations build resilience and leadership through executive coaching and immersive battlefield leadership experiences. Connect with David Fivecoat & Cynergists David's Website: http://thefivecoatconsultinggroup.com Cynergists: http://www.cynergists.com Chapters: 00:00 - Intro 1:05 - David's Military Background & Career 04:10 - Transition Advice: Get Corporate Experience First 06:30 - Launching a Business in March 2020 08:25 - TFCG 2.0: Pivoting to Battlefield Tours 10:45 - The Solopreneur Marketing Struggle 13:30 - Rapid Fire Questions 17:35 - Advice to Younger Self: Prioritize Sleep! 19:58 - Outro