TheMilVet Podcast

Brendan Aronson and Tim Hsia

Your hosts, Brendan Aronson and Tim Hsia, interview the highest-performing military veterans & civilian allies on earth. Our guests include CEOs of multibillion-dollar companies, founders of incredible businesses, and legendary investors. Our goal is educate, inspire, and entertain you. 

  1. 5D AGO

    Ep. 164 From Military to Cloud: How Veterans Are Breaking Into Tech for Free

    In this episode of TheMilVet Podcast, host Beau Higgins sits down with Gregory Henson, founder of Cloud Veterans and former tech CEO, and Philip Lukaszonas, a U.S. Army veteran and manager of customer success at Ingram Micro to discuss how they are helping veterans build careers in cloud technology. Greg and Philip share the origin story behind Cloud Veterans—a nonprofit initiative built to solve a major gap in the hiring pipeline: talented veterans with the right mindset but lacking access to training, certifications, and guidance to enter the tech industry. Drawing from Greg’s experience scaling a global Microsoft partner and Philip’s own challenging transition out of the military, they unpack how Cloud Veterans is bridging that gap through free, structured, and community-driven training. The conversation dives into the realities many veterans face when transitioning, especially those from non-technical or combat arms backgrounds, and how programs like this are designed to meet them exactly where they are. From foundational certifications to advanced cloud pathways, Cloud Veterans provides not just training, but mentorship, accountability, and a lifelong support network. Listeners will gain insight into: Breaking into cloud and tech careers with zero prior experienceTranslating military skills like discipline, adaptability, and problem-solving into the corporate worldOvercoming imposter syndrome and intimidation around tech rolesThe importance of community, mentorship, and accountability in career transitionsHow hands-on labs, certifications, and real-world prep accelerate job readinessLeveraging AI tools to enhance job search, preparation, and long-term career growthWhy tech careers, especially in cloud, remain resilient in the age of AIGreg and Philip also share their bold vision for scaling Cloud Veterans to serve thousands of veterans annually, while maintaining a 100% free, volunteer-driven model supported by corporate sponsors. Their mission is clear: empower veterans and their spouses with the tools, training, and confidence needed to thrive in tech, and continue serving in new ways beyond the uniform. Whether you're a transitioning service member, a veteran exploring new career paths, or someone looking to break into tech, this episode offers practical guidance, inspiration, and a clear roadmap to get started. 🔗 Learn more about Cloud Veterans → cloudveterans.org 🔗 Connect with TheMilVet → themilvet.org 🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service. #Veterans #MilitaryTransition #TechCareers #CloudComputing #Leadership #CareerGrowth #Reskilling #AI #ServiceAfterService #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    37 min
  2. APR 15

    Ep. 163 From the White House to the Private Sector: Lessons from Ari Fleischer

    In this episode of TheMilVet Podcast, host Beau Higgins speaks with former White House Press Secretary Ari Fleischer about career transitions, leadership in high-pressure environments, and building a path beyond government service. Fleischer reflects on how he moved from college with no clear plan to Capitol Hill and then to the White House, where he served as press secretary to President George W. Bush during the September 11 attacks. The conversation then shifts to Ari’s transition out of government after more than two decades of service. He breaks down how he navigated burnout, leveraged his network, and built a thriving career in communications consulting, advising major corporations and sports organizations during moments of crisis and public scrutiny. Listeners will gain insight into: How careers can evolve unexpectedly and why staying open to opportunity mattersThe power of networking (and why it’s really about relationships, not transactions)Lessons in leadership, loyalty, and accountability from the White HouseNavigating career transitions, burnout, and life after high-pressure rolesBuilding a consulting career by identifying and owning your unique skill setWhy specificity, not generality, is key when marketing yourself professionallyHow veterans can translate military experience into real-world career successAri also shares powerful perspectives on gratitude, service, and why veterans have a distinct advantage in the workforce; highlighting the discipline, resilience, and reliability that set them apart. Whether you're transitioning out of the military, exploring a career pivot, or looking to sharpen your professional edge, this episode delivers practical advice, real-world lessons, and inspiration from one of the most recognizable voices in modern political communications. 🔗 Learn more about TheMilVet → themilvet.org  🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service.#Veterans #Leadership #CareerTransition #Networking #Consulting #PublicRelations #ServiceAfterService #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    41 min
  3. APR 8

    Ep. 162 Choosing Family Over Command: Randy Mullen on Building a Mission Beyond the Military

    In this episode of TheMilVet Podcast, host Beau Higgins sits down with Randy Mullen, Founder & CEO of Sightline Ventures and a former U.S. Air Force Officer, to explore his journey from military service to building a mission-driven company in the defense tech space. Randy shares how his upbringing near Edwards Air Force Base first sparked his interest in the military, eventually leading him into Air Force contracting and acquisitions. With experience spanning global deployments, the National Reconnaissance Office, and the Education with Industry program at Ball Aerospace, he developed a deep understanding of how the Department of Defense operates and how innovation reaches the warfighter. Throughout the conversation, Randy offers a candid look at one of the hardest decisions of his life: stepping away from a promising military career and command opportunity to prioritize his family. He opens up about the emotional weight of that transition, the uncertainty that followed, and how a series of unexpected pivots ultimately led him to entrepreneurship. Listeners will gain insight into: Choosing family over career and navigating the tension that comes with itEmbracing uncertainty and adapting when plans fall apartTranslating military experience into entrepreneurship and business developmentBuilding a company with purpose while continuing to serve beyond the uniformTaking calculated risks and betting on yourself during transitionReinventing yourself to stay challenged, relevant, and growingInvesting in mentorship, personal development, and long-term visionRandy also shares how Sightline Ventures is helping early-stage defense tech companies bridge the gap between innovation and implementation, ensuring critical technologies get into the hands of those who need them most. His story is a powerful reminder that while transition may be messy and unpredictable, it can also open doors to impact, growth, and renewed purpose. Whether you’re navigating your own transition, exploring entrepreneurship, or looking to lead with greater intention, this episode delivers practical insight and real-world perspective to help you move forward with confidence. 🔗 Connect with TheMilVet → themilvet.org  🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service. #Veterans #MilitaryTransition #Leadership #Entrepreneurship #DefenseTech #PersonalGrowth #Resilience #ServiceAfterService #Startups #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    39 min
  4. APR 1

    Ep. 161 From Nuclear Submarines to Biotech CEO: Mike Gaffney’s Unconventional Journey

    In this episode of TheMilVet Podcast, host Beau Higgins sits down with Mike Gaffney, Naval Academy graduate, former nuclear-trained submarine officer, and now CEO of Cellphire Therapeutics, Inc., to unpack a career that spans undersea operations, top-tier consulting, private equity, and biotech leadership. Mike shares how growing up around his father’s Naval Academy classmates and mentors, including a future vice admiral, shaped his decision to attend the Academy, not for prestige, but for values, character, and leadership. An unlikely nuclear submariner who majored in English and later earned a graduate degree in politics, he explains how the process of elimination, the end of the Cold War, and a few hard realities (like getting seasick and wearing glasses) pushed him beneath the surface and into the Navy’s nuclear community. Mike then walks through his pivot from consulting into the investment world with Allied Capital, where he ultimately became the firm’s de facto healthcare lead. He breaks down how the private equity landscape has transformed since the late ’90s, from a smaller, less crowded field to today’s hyper-competitive market where deal flow, specialization, and relationships are everything and why that shift pushed him toward building companies rather than just backing them. Throughout the conversation, Mike offers practical insight on: Leveraging your network the right way; focusing on adding value, reciprocity, and long-term relationships rather than transactional asksTranslating military leadership into commercial settings by obsessing over team quality, clarity of purpose, and execution disciplineSurviving “getting punched in the face” in business through resilience, problem solving, and resourcefulness forged in uniformUnderstanding how modern private equity and growth capital really work;  why deal flow, specialization, and operating value creation matter more than everStepping into a new leadership role with humility, curiosity, and a deliberate approach to listening before changing thingsShaping culture intentionally so strategy doesn’t just live on a slide, but shows up in daily behaviors and decisionsFor veterans interested in private equity, venture capital, or executive roles in high-growth companies, Mike offers grounded advice: this is a brutally competitive space where many people want the same jobs, but trusted introductions, demonstrated grit, and a reputation for solving hard problems can differentiate you. He emphasizes that trust and likeability aren’t built in one conversation or a single coffee, they compound over time through consistent behavior, follow-through, and showing up for others. 🔗 Connect with TheMilVet → themilvet.org 🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service. #Veterans #MilitaryTransition #Leadership #PrivateEquity #VentureCapital #Healthcare #Biotech #Resilience #Networking #ServiceAfterService #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    34 min
  5. MAR 25

    Ep. 160 From Bomber Pilot to Business Owner: Matt Brooks on Winning After Service

    In this episode of TheMilVet Podcast, host Beau Higgins sits down with Matthew R. Brooks, Founder and Principal of Second Echelon Capital, Colonel, US Air Force (Retired) and U.S. Air Force Academy graduate to explore his journey from the cockpit to entrepreneurship, and now to investing in fellow veterans. A graduate of the United States Air Force Academy, Matt shares how a single touchdown catch against Notre Dame became a lifelong lesson in teamwork, humility, and mission-first leadership. He reflects on his Air Force career, commanding the 5th Bomb Wing, and the values that shaped him; integrity, service, and excellence. But Matt’s story doesn’t stop at retirement. After leaving active duty, he stepped into the world of entrepreneurship, acquiring and scaling his family’s hotel supply company before successfully exiting. Now, as founder of Second Echelon Capital, he invests in veteran-owned small businesses, helping other service members navigate the path of entrepreneurship through acquisition (ETA). Throughout the conversation, Matt dives into: The realities of military transition; what he expected vs. what surprised himEntrepreneurship through acquisition (ETA) and why buying a business can be a powerful path for veteransThe sleepless nights, financial pressure, and hands-on leadership required to run a small businessWhy community matters, and how organizations like Entrepreneurs' Organization help founders avoid going it aloneTranslating military leadership into building systems, processes, and high-performing teamsAligning your commercial pursuits with your personal passionsThe importance of mentorship, financial readiness, and learning when to say “no”Matt also shares practical resources including books, podcasts, and conferences for veterans interested in business ownership, along with candid advice about preparing your family and finances before taking the entrepreneurial leap. Whether you're a transitioning service member, a veteran considering buying a business, or a leader looking to invest with purpose, this episode offers a real-world look at what it takes to move from leading airmen to leading companies, and from operator to investor. 🔗 Connect with Matt Brooks → secondecheloncapital.com 🔗 Email → matthew@secondecheloncapital.com 🔗 Follow on LinkedIn → Matthew R. Brooks 🔗 Connect with TheMilVet → themilvet.org 🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service. #Veterans #AirForce #Entrepreneurship #MilitaryTransition #Leadership #VeteranOwned #SmallBusiness #Investing #ETA #PrivateEquity #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    36 min
  6. MAR 18

    Ep. 159 Growth Beyond Rank: Sean Patterson on Mentorship, Mindset, and Transition

    In this episode of TheMilVet Podcast, host Beau Higgins sits down with Sean Patterson, Founder of CrossGen AI and Chief Operations Officer at StartGuides, a former U.S. Navy submarine officer, and a graduate of the United States Naval Academy and the Massachusetts Institute of Technology. Sean reflects on how the foundation of service, rooted in discipline, accountability, and commitment to something greater than yourself, continues to influence how he leads, makes decisions, and approaches new challenges. Drawing from both high-pressure moments and everyday leadership responsibilities, he shares how clarity of values becomes a compass when circumstances are uncertain. Throughout the conversation, Sean offers an honest look at transition; what it feels like to step away from a structured military environment and into a world where you must define your own direction. He speaks candidly about identity shifts, professional reinvention, and the internal work required to grow beyond previous titles or roles. Listeners will gain insight into: Anchoring your decisions in core values during seasons of changeTranslating military leadership into business, entrepreneurship, and community impactNavigating the emotional and professional realities of transitionLetting go of ego while maintaining high performance standardsBuilding resilience through discomfort, responsibility, and ownershipRedefining success beyond rank, position, or external validationLeading with humility while embracing long-term visionSean also discusses the importance of mentorship, surrounding yourself with the right people, and continuously refining your mindset as responsibilities increase. His story highlights that growth doesn’t stop when service ends, it evolves. Whether you’re preparing to transition, currently navigating change, or striving to lead at a higher level, this episode delivers grounded wisdom and practical insight to help you move forward with clarity and conviction. 🔗 Connect with TheMilVet → themilvet.org 🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service. #Veterans #Leadership #MilitaryTransition #PersonalGrowth #Entrepreneurship #Resilience #ServiceAfterService #Mentorship #MilitaryToCivilian #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    47 min
  7. MAR 11

    Ep. 158 From Apache Pilot to AI Founder: Lindsey Chrismon on Leadership, Risk, and Entrepreneurship

    In this episode of TheMilVet Podcast, host Beau Higgins sits down with Lindsey Chrismon, co-founder and CEO of Oply, former U.S. Army aviation officer, AH-64 Apache pilot, and the first woman in U.S. Army history to fly the AH-6 Little Bird in the 160th Special Operations Aviation Regiment (Airborne). A graduate of the United States Military Academy at West Point and Harvard Business School, Lindsey shares her journey from an 11-year-old determined to attend West Point to becoming a venture-backed tech founder building in the AI space. Lindsey reflects on the mentors who shaped her leadership style, the intensity of serving in the 160th SOAR, and the pivotal decision to transition from a high-performing military career into entrepreneurship. She speaks candidly about betting on herself, walking away from traditional post-MBA paths like consulting, and committing fully to building something from the ground up. Throughout the conversation, Lindsey breaks down how she and her husband scaled their first company before launching Oply—an AI-powered home intelligence platform designed to help homeowners proactively manage, maintain, and protect their most valuable asset. Listeners will gain insight into: • What it takes to become a “first” in elite military organizations  • The power of mentorship in accelerating performance and confidence  • Making the stay-or-go decision at a critical military career inflection point  • Why committing fully—without a backup plan—matters in entrepreneurship  • The realities of raising venture capital and keeping a clean cap table  • How failure as a founder can increase long-term earning potential  • Building AI responsibly while navigating evolving policy and regulation  • Translating special operations leadership into startup execution Lindsey also discusses the importance of embracing risk, overcoming fear of failure, and staying mission-focused during uncertainty—whether in combat aviation or venture-backed startups. Her story is a testament to disciplined ambition, bold decision-making, and the belief that service is a foundation—not a ceiling. Whether you’re considering entrepreneurship, navigating transition, or leading in high-stakes environments, this episode delivers practical insight and inspiration for veterans ready to build what’s next. 🔗 Connect with TheMilVet → themilvet.org  📲 Learn more about Oply → Download “Oply” on the App Store or Google Play  🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service. #Veterans #Leadership #MilitaryTransition #Entrepreneurship #AI #WomenInDefense #SpecialOperations #StartupLife #Resilience #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    58 min
  8. MAR 4

    Ep.157: From Infantry to Cyber Command: Ryan Heritage on Transitioning from Marine General to Defense Tech Advisor

    In this episode of TheMilVet Podcast, host Beau Higgins sits down with retired U.S. Marine Corps Major General  Ryan Heritage—a career infantry officer who made a rare and impactful pivot into cyberspace, and information warfare. From watching The Sands of Iwo Jima as a fourth grader in Massachusetts to commanding at the regimental level and later leading Marine Corps Forces Cyber Command, Ryan’s journey reflects both deep-rooted commitment to service and an exceptional ability to evolve with the battlefield.  Ryan shares what it was like to step into the cyber domain with no technical background—and how curiosity, humility, and disciplined leadership allowed him to thrive. He offers a candid look at modern warfare, the rapid evolution of AI and cyber capabilities, and why simplifying complex technology for warfighters is critical to maintaining decision advantage. The conversation also dives deep into Ryan’s recent transition from active duty to building a portfolio career in the private sector. He reflects honestly on missteps, sleepless nights, networking lessons, and the mindset shift required to move from military command to business development. Listeners will gain insight into: Leading in highly technical environments without being the technical expertTranslating infantry and combat leadership into cyberspace operationsThe importance of curiosity and continuous learning in emerging domainsWhy networking—not resumes—is the real engine of post-service opportunityManaging identity shifts after retirement from senior military leadershipApproaching transition with humility, research, and value-driven conversationsUnderstanding why military rank does not automatically equate to corporate rolesRyan also discusses lessons from Ukraine’s rapidly evolving battlefield, the urgency of AI adoption, and why strategy—not bureaucracy—must drive innovation at scale. He offers practical advice for veterans navigating transition, emphasizing preparation, intentional relationship-building, and disciplined follow-through. Whether you’re an infantry officer curious about cyber, a senior leader preparing to transition, or a veteran exploring opportunities in defense tech and venture capital, this episode delivers both strategic perspective and grounded, practical advice. 🔗 Connect with TheMilVet → themilvet.org  🎧 Subscribe on Apple Podcasts, Spotify, and YouTube for more conversations empowering veterans to win after service. #Veterans #Leadership #MilitaryTransition #CyberWarfare #DefenseTech #AI #PrivateEquity #VentureCapital #Entrepreneurship #ServiceAfterService #TheMilVetPodcast Thanks for listening! Here's how you can find us to continue the conversation: Tweet us at @brendan_aronson Follow us on Instagram at @themilitaryvet Subscribe to our Weekly Newsletter at https://www.themilvet.org/resources-for-veterans Check out our video content on Youtube at https://www.youtube.com/@themilitaryvet

    47 min
5
out of 5
21 Ratings

About

Your hosts, Brendan Aronson and Tim Hsia, interview the highest-performing military veterans & civilian allies on earth. Our guests include CEOs of multibillion-dollar companies, founders of incredible businesses, and legendary investors. Our goal is educate, inspire, and entertain you. 

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