#340: Building a National Real Estate Brand for Veterans with Travis Winfield, USN Ret.‘16
Service Academy Business Mastermind
Release Date: 10/24/2025
#353: Modernizing Capital Raising with Jesse Prince, USMA ‘04
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Charleston, SC on June 1st & 2nd? Visit: ____ Jesse Prince is an Army veteran who served nearly six years on active duty, including two combat tours to Iraq. After transitioning from the military, he built a career in commercial real estate brokerage while earning his Master’s in Real Estate Finance from NYU, graduating near the top of his class and deepening his expertise in institutional-level real estate. Today, Jesse is the founder of IncrediVer, an AI-powered accredited investor verification and...
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#352: Building Workforce Housing to Close Supply Gaps in Growing Markets with Tom O’Hare, USNA ’01
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Charleston, SC on June 1st & 2nd? Visit: ____ Tom O’Hare is a U.S. Navy veteran and the founder of Keel Capital and Keel Home Development, where he leads multifamily and infill residential projects across the Midwest and Northern Virginia. Before starting his own companies, Tom spent 17 years in real estate investment banking and later served as CIO and COO of a national single-family rental platform. During that time, he worked on large institutional portfolios and gained firsthand experience in how...
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#351: Building a Multi-Billion-Dollar Real Estate Platform Through Disciplined Investing with Tim Siemer, USAFA ‘06 & Mike Siemer
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Charleston, SC on June 1st & 2nd? Visit: ____ Tim Siemer is an Air Force veteran, aviator, and partner at SMB Equity, a real estate private equity firm investing in stabilized and development projects nationwide. At SMB, Tim focuses on evaluating new opportunities and managing investor relationships, applying a disciplined risk management approach shaped by years in military and commercial aviation. He works alongside his father, Mike Siemer, who transitioned into real estate investing after a career as...
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#350: The One-Stop Platform Helping Financial Advisors Work Smarter with Ryan Dau, USAFA ‘17
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Charleston, SC on June 1st & 2nd? Visit: ____ Ryan Dau is a former Air Force officer, and founder of ReframeRIA, a consultancy that helps financial advisors streamline their operations, refine their client experience, and optimize their technology stack. Through ReframeRIA, Ryan partners with advisory firms to improve their workflows, refine their client experience, and implement technology that truly supports their businesses. His mission is simple: remove the operational chaos that slows...
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#349: Helping Veterans Break Into Tech Sales with Andrew Garcia, USNA ‘10
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Charleston, SC on June 1st & 2nd? Visit: ____ Andrew Garcia is a U.S. Navy veteran and founder of and , two businesses focused on helping veterans and transitioning professionals break into the tech industry. After a successful career in tech sales at Salesforce, Andrew launched The Arena to provide veteran-friendly recruiting services for defense tech startups. He later expanded his mission through Pursuit, a career training platform designed to help aspiring tech sales professionals land their first...
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#348: Revolutionizing TDY: How Furniture and Tech Are Solving a $10B Problem with Steve Buchanan, USMA ‘99
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Charleston, SC on June 1st & 2nd? Visit: ____ Steve Buchanan is a U.S Army Veteran and the CEO of TDY Rentals, a company on a mission to transform the way government travelers experience temporary duty assignments. What started as a frustrating personal experience with TDY housing, turned into a purpose-driven venture to make extended stays feel less like deployments, and more like home. At TDY Rentals, Steve and his team provide fully furnished tech-enabled housing solutions tailored for government...
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#347: Scaling Businesses 10X in 3 Years with Jeff Evenson, USMA ‘90
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Charleston, SC on June 1st & 2nd? Visit: ____ Jeff Evenson is an experienced business leader and scaling strategist at scaling.com, where he works with founders who are ready to move from early traction to sustained growth. Alongside Blake Erickson and Dr. Benjamin Hardy, he helps entrepreneurs shift from being day-to-day operators to becoming strategic leaders who design companies that scale. Over the last two decades, Jeff built and exited multiple businesses, including a $3.5M hair salon operation, a...
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#346: How EOS Helps Founders Get Their Life Back with Kurt Greene, USMA ‘87
Service Academy Business Mastermind
Kurt Greene is a certified EOS Implementer at EOS Worldwide, where he helps leadership teams build stronger, more scalable companies. A graduate of West Point and an Army veteran, Kurt brings a unique mix of Fortune 500 leadership, HR expertise, and peer-group facilitation experience through Vistage Worldwide, Inc. He works with founders and executive teams to implement practical tools that cut through complexity so they can regain control, align their teams, and get back to their visionary role. Whether partnering with veteran-owned businesses or mission-driven entrepreneurs, Kurt’s work is...
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#345: Helping Veterans Thrive Through Wild Bill’s Franchise with Michael Quilty, USNA ‘88
Service Academy Business Mastermind
Need financing for your next investment property? Visit: ____ Michael Quilty (USNA '88) is a Navy veteran and franchise development leader who's built his career around creating opportunities for others. After years leading growth and strategy across multiple industries, he's now focused on helping fellow veterans transition to entrepreneurship through franchising. At Wild Bill’s, he plays a key role in growing the company’s franchise footprint, and expanding the presence of their nostalgic craft soda brand across the country. Michael’s work focuses on identifying the right partners,...
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#344: Helping High School Students Navigate the Service Academy Admissions Journey with Travis Wittick, USAFA ‘07
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in Tampa, FL on January 26th & 27th? Visit: ____ Travis Wittick is the founder of Academy Endeavors, a coaching company that helps high school students navigate the competitive and complex admissions process for U.S. Service Academies and ROTC scholarships. A graduate of the U.S. Air Force Academy and former Air Force hospital administrator, Travis first discovered his passion for mentorship as an Academy Liaison Officer helping students prepare their applications while still on active duty. After...
info_outlineNeed financing for your next investment property? Visit: https://www.academyfund.com/
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Travis Winfield is the founder of Military Operated Real Estate, and author of the upcoming book Military Money and More. A retired Navy Command Senior Chief with 24 years of service, Travis founded the Winfield Group in Southern California, successfully helping 100-150 military families per year before passing the business to his son in 2024.
Recognizing that less than 12% of the nearly 20 million active duty and veteran population has used their VA home loan benefit, Travis launched MORE to create the first national real estate brand exclusively serving the military community. With military-affiliated certified agents, SkillBridge integration, and VA-approved education benefits for real estate training, MORE aims to become the trusted resource for veterans coast to coast, the "USAA of real estate."
In this episode of the SABM podcast, Scott chats with Travis about:
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Military Operated Real Estate (MORE): Creating a national brand connecting veterans with military-affiliated certified agents.
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Mission Before Commission: Training agents as resource managers who understand veteran benefits beyond transactions.
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SkillBridge and Ambassador Programs: Leveraging VA benefits to create opportunities for transitioning members and military spouses.
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Financial Literacy Crisis: Addressing the education gap affecting military families through his book Military Money and More.
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Long-Term Vision: Making MORE the trusted real estate brand synonymous with USAA and Navy Federal.
Timestamps:
00:37 Travis's Journey into Real Estate
01:43 Building the Winfield Group
02:10 Mission Before Commission
03:46 The Vision for Military Operated Real Estate
06:27 Financial Literacy and the New Book
07:39 Future Goals and Challenges
11:42 How the Platform Works
Connect with Travis:
If you found value in today's episode, don't keep it to yourself—share it with a colleague or friend who could benefit. And if you're a Service Academy graduate ready to elevate your business, we'd love for you to join our community and get started today.
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A special thank you to Travis for joining me this week. Until next time!
-Scott Mackes, USNA '01