#352: Building Workforce Housing to Close Supply Gaps in Growing Markets with Tom O’Hare, USNA ’01
Service Academy Business Mastermind
Release Date: 03/19/2026
#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/
Want to join us in Charleston, SC on June 1st & 2nd?
Visit: https://www.10xvets.com/events
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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 deals are evaluated, financed, and executed at scale. He now brings that perspective into his own development work.
Today, Tom focuses on workforce housing and ground-up projects that help close supply gaps in growing markets. He partners with investors, local governments, and community stakeholders to move projects from concept to completion and deliver housing that meets real community needs.
In this episode of the SABM podcast, Scott chats with Tom about:
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Stepping Into Entrepreneurship: What it took for Tom to leave a corporate executive role and “turn pro” as a full-time developer
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Midwest Multifamily Strategy: Why markets like Michigan and Ohio offer strong demand, supply gaps, and favorable development incentives
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Urban Infill Development: How shorter-cycle projects in Northern Virginia complement long-term multifamily developments
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The Brixton Project: A 148-unit workforce housing development backed by tax increment financing and strong rent fundamentals
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Deal Sourcing Through Relationships: Why Tom finds the best opportunities through networks, direct outreach, and boots-on-the-ground insights.
Timestamps:
00:28 Tom's Real Estate Journey
01:20 Advice for Aspiring Entrepreneurs
04:46 Types of Real Estate Projects
07:57 Current Projects and Market Focus
10:12 Future Goals and Plans
14:31 Sourcing Deals and Partnerships
Connect with Tom:
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 Tom for joining me this week. Until next time!
-Scott Mackes, USNA '01