Milpreneur | Dida Clifton | The Office Squad: Building Mission-Ready Businesses

Milpreneur | David Fivecoat | Pivoting From Combat to Consulting

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

Milpreneur | Matthew DePrimo | How to Recruit 1,200 People in 1 Year

Matthew DePrimo went from a high-speed active duty Army officer to being medically retired at 28, facing a sudden loss of identity and mission. Instead of slowing down, he channeled his drive into education and entrepreneurship, founding Career Bridge—a specialized STEM recruiting firm. In a display of massive action, Matthew and his team successfully placed over 1,200 candidates in a single year, proving that military precision translates directly to business growth. In this episode, Matthew shares how he built a company rooted in military values, specifically focusing on connecting underrepresented groups with top-tier opportunities. He reveals his unique philanthropic business model that donates 20% of revenue back to the educational institutions his candidates come from, creating a sustainable cycle of opportunity for veterans, minorities, and international students. In this episode, you will learn: • Navigating Medical Retirement: How to find a new purpose and identity when your military career ends abruptly. • Scaling Recruitment: The mindset and "massive action" strategy behind recruiting 1,200+ candidates in just 12 months. • The Philanthropic Business Model: How donating 20% of revenue back to schools fuels growth, trust, and community impact. • Military Values in Business: How to translate camaraderie, discipline, and mission-focus into a remote corporate culture. • Fail Fast to Succeed: The importance of pivoting quickly—from a Managed Service Provider (MSP) to Recruiting—when the market speaks. About Matthew DePrimo: Matthew DePrimo is the Founder and CEO of Career Bridge IT Solutions, a STEM recruiting firm dedicated to connecting underrepresented talent with meaningful careers. A medically retired Army veteran and former Signal Officer, Matthew leverages his military leadership experience to build high-performing teams. He holds a Master's in Information Systems from Syracuse University and is passionate about lowering barriers to education and employment for veterans, BIPOC communities, and women in STEM. Connect with Matthew DePrimo & Cynergists: Matthew's Website: https://careerbridgeitsolutions.com/ LinkedIn: Matthew DePrimo, MSIS, CAS-IS Facebook (Business): CareerBridge I.T. Solutions LLC Personal Facebook: Matty John https://www.facebook.com/matthew.deprim Cynergists Website: http://www.cynergists.com #Milpreneur #MilpreneurPodcast #VeteranEntrepreneur #Recruiting #BusinessScaling #STEMCareers #CareerBridge #MilitaryTransition #VeteranBusiness #Entrepreneurship #GivingBack Chapters: 00:00 - Intro 00:27 - Introducing Matthew DePrimo & Career Bridge 03:00 - From Enlistment to Signal Officer 08:40 - The Challenge of Medical Retirement 11:30 - The Birth of Career Bridge 13:30 - Pivoting to STEM Recruiting 17:14 - Result: 1,200 Placements in One Year 18:20 - The 20% Give-Back Model 21:00 - Instilling Military Culture in Business 26:47 - Rapid Fire Questions 33:00 - Conclusion

Milpreneur | Dr. Mark Michels | From Private to Lt. Col. to Corporate COO

In this episode of the Milpreneur Podcast, Ryan Van Ornum sits down with Dr. Mark Michels, the Chief Operating Officer of Global Integrity Alliance. Mark shares his incredible 31-year journey in the U.S. Army, rising from a Private E-1 to retiring as a Lieutenant Colonel. He discusses his unique path from Air Defense Artillery to becoming a Counter-WMD expert and eventually the Academic Provost at the Defense Nuclear Weapons School. Mark opens up about the realities of transitioning from the military to the corporate world, specifically how he navigated the shift during the height of COVID. He shares powerful stories on leadership, including a harrowing experience at Fairchild Air Force Base, and offers invaluable advice on why "operationalizing the visionary" is the key to business success. Whether you are an enlisted soldier looking to commission or a veteran entering the C-Suite, Dr. Michels' insights on lifelong learning and resilience are a must-listen. In this episode, you will learn: • The Value of "Volunt-telling": How volunteering for the jobs nobody else wants (like field sanitation) can unexpectedly open doors to elite opportunities like Air Assault School. • Operationalizing the Vision: The specific role of a COO in taking a CEO's high-level ideas and translating them into actionable, executable plans. • Leadership Through Tragedy: A somber look at resilience and rebuilding a unit's morale following the tragic C-17 crash at Fairchild Air Force Base. • The Power of Lifelong Learning: Why Mark never stopped at one degree, eventually earning his Doctorate, and how continuous education fuels career progression. • Navigating the Civilian Transition: How to translate military trust and "handshake deals" into the documentation-heavy world of civilian business consulting. About Dr. Mark Michels: Dr. Mark Michels is a retired U.S. Army Lieutenant Colonel with over 31 years of service, having served in both enlisted and officer ranks. He is a subject matter expert in Counter-Weapons of Mass Destruction (CWMD) and previously served as the Chief of Operations and Academic Provost for the Defense Nuclear Weapons School. He is currently the COO of Global Integrity Alliance and the author of Learning from Experience: 50 Principles for Leading People and Managing Programs Through Trials, Tribulations, and Successes. Connect with Dr. Mark Michels & Cynergists Global Integrity Alliance: https://www.globalintegrityalliance.com Cynergists: http://www.cynergists.com Chapters 00:00 - Intro 02:07 - 31 Years: From Private to Officer 05:05 - The Power of Volunteering (The Field Sanitation Story) 07:54 - Leadership Through Tragedy: The Fairchild Air Show Crash 09:37 - Earning a Doctorate & The Pivot During COVID 11:16 - The "Alex Inc" Call & Moving to Germany 15:15 - Current Role: COO of Global Integrity Alliance 17:23 - Rapid Fire Questions

Milpreneur | Dida Clifton | The Office Squad: Building Mission-Ready Businesses

In this episode of the Milpreneur Podcast, host Ryan Van Ornum sits down with Dida Clifton, a USAF veteran and the founder of The Office Squad. Dida shares her incredible journey from working in an F-15 fighter squadron to building a comprehensive back-office support system for small businesses. By leveraging her military background, she has created a unique "Squadron" model that brings discipline, urgency, and systems to the often chaotic world of entrepreneurship and bookkeeping.Dida dives deep into the struggles of branding and the pivotal moment she decided to ignore the naysayers who told her a military-themed business wouldn't resonate with civilians. She discusses the evolution of her company from a solo home-based operation to a growing franchise, detailing how she navigated technological shifts in the accounting industry. This conversation offers invaluable insights on scaling operations, maintaining work-life balance as a military spouse, and the power of trusting your intuition to build a legacy that allows you to retire your spouse. In this episode, you will learn:• Applying Military SOPs: How to translate military squadron structure into efficient small business administration.• Branding with Authenticity: Why leaning into your veteran identity can differentiate your business in a crowded market.• Scaling through Systems: The transition from being a solo operator to franchising and acquiring other firms.• Technological Adaptation: How to stay ahead of industry curves, from cloud hosting to AI integration in bookkeeping.• Work-Life Integration: Strategies for building a successful empire without sacrificing family relationships.About Dida Clifton: Dida Clifton is the founder and CEO of The Office Squad, a premier back-office support company that handles bookkeeping, admin, and phone support for small businesses. A U.S. Air Force veteran, she applies the discipline and structure of military flight operations to help entrepreneurs streamline their business systems.Connect with Dida Clifton & Cynergists:The Office Squad Website: http://www.theofficesquad.comSponsor: The sponsor is Cynergists: http://www.cynergists.comJoin us next time for more stories of veterans turning military service into business success!#Milpreneur #TheOfficeSquad #VeteranBusiness #USAF #Bookkeeping #Franchising #SmallBusinessSystems #WomenInBusiness #Entrepreneurship #scalingupsuccess Chapters:00:00 - Introduction and Sponsor Acknowledgment00:53 - Dida’s Military Service: From Bootcamp to F-15 Fighter Squadrons02:35 - The Origin of The Office Squad: Applying Military Structure to Admin04:02 - Overcoming Early Business Challenges and Listening to Experts05:35 - The Branding Pivot: Embracing the Fighter Pilot Theme07:22 - The "Just Do It" Moment: Ignoring Doubters08:21 - Balancing Motherhood, Military Spousal Duties, and Business Growth09:30 - Staying Ahead of Trends: Cloud Hosting and Technology Shifts12:13 - Rapid Fire Questions: Books, Travel, and Superpowers14:58 - Advice to Her Younger Self: Don't Let Your Face Show What You're Thinking16:40 - Future Vision: Scaling to 25 Locations in 5 Years17:18 - Connect with Dida Clifton & Closing

Milpreneur | Marah Lago | From 8-Figure Founder to Military Creator Con Visionary

In this episode of the Milpreneur Podcast, host Ryan Van Ornum sits down with Marah Lago, a powerhouse entrepreneur and co-founder of Military Creator Con. Marah shares her incredible journey from the high-pressure world of corporate management consulting to navigating the utter collapse of her first business, eventually rising to build a vertically integrated jewelry empire. This conversation explores how a civilian spouse found her true home within the veteran community and is now dedicating her expertise to helping military creators scaling their own visions. Marah opens up about the harsh lessons learned from a business bankruptcy and how those scars prepared her to bootstrap a global brand from zero to eight figures without outside investors. They dive deep into the mechanics of finding a unique niche—in her case, the rare Larimar gemstone—and the operational systems required to manage mining, manufacturing, and retail distribution simultaneously. Marah also discusses the "shocking creativity" she has discovered within the military population and why agility and calculated risk-taking are the ultimate force multipliers in business. In this episode, you will learn: • How to pivot from failure: Turning a business bankruptcy into the foundation for future 8-figure success. • The power of vertical integration: How controlling your supply chain from mining to retail maximizes margins. • Identifying a market niche: Lessons on discovering and branding a unique product (Larimar) that the competition ignores. • Applying military agility to business: Why veterans are uniquely suited for entrepreneurship due to their ability to adapt and overcome. • Building community events: Insights into launching the Military Creator Con to foster collaboration among veteran creatives. About Marah Lago: Marah Lago is an accomplished entrepreneur and designer best known for building the Marah Lago jewelry brand into an 8-figure global enterprise. Today, alongside her husband, a retired Air Force veteran, she is the co-founder of Military Creator Con, an event dedicated to empowering creatives, influencers, and entrepreneurs within the military community. Connect with Marah Lago & Cynergists: Military Creator Con Website: https://www.militarycreatorcon.com Sponsor: The sponsor is Cynergists: http://www.cynergists.com Don't miss this inspiring masterclass on resilience and branding—hit that subscribe button and leave a review! #Milpreneur #MilitaryCreatorCon #MarahLago #VeteranBusiness #Entrepreneurship #ScalingUp #Bootstrapping #WomenInBusiness #AirForceSpouse #CreatorEconomy Chapters: 00:00 - Introduction & Cynergists Sponsorship 01:19 - Leaving Corporate America & The Glass Ceiling 02:24 - First Business Failure: The Sizzler Bankruptcy 03:28 - From Mall Kiosk to Discovering Larimar 04:41 - Bootstrapping to 8-Figures: Vertical Integration 05:56 - TV Sales Success & The Final Exit 07:05 - Finding a Soul Connection in the Military Community 07:43 - The Birth of Military Creator Con 09:02 - The Untapped Creativity of Veterans 10:47 - The Importance of Community & Networking 11:27 - Rapid Fire Questions: Books, Mentors & Pizza 12:30 - Conclusion & Call to Action