#311: Financial Planning with Private Investments, Tax Loss Harvesting & Charitable Giving with David Chepauskas, USMA ‘77
Service Academy Business Mastermind
Release Date: 02/15/2025
Service Academy Business Mastermind
Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Jeff Servello is a seasoned leader and trusted Principal Advisor specializing in executive coaching, leadership development, and crisis response. A U.S. Naval Academy graduate, he also holds a Master of Professional Studies in Leadership, Education, and Development from the University of Maryland. Over the past 20 years, Jeff has led award-winning teams, managed billion-dollar resources, and coached cross-functional units to high performance in...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Jeff Tegman is the Vice President of LCAB Holdings, a veteran-owned holding company redefining how the commercial construction industry attracts talent, maintains quality, and drives operational excellence. An Army veteran with an MBA in Engineering Management, Jeff leads LCAB’s strategy of acquiring specialized construction companies, building a resilient network that addresses industry fragmentation and labor shortages while raising the standard for...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Jeff Martinovich is a seasoned business advisor, entrepreneur, and U.S. Air Force veteran with a background in finance, leadership, and strategic growth. A former Gulf War officer, he went on to build a billion-dollar investment firm, gaining firsthand experience in high-performance leadership and navigating complexity under pressure. After a highly public legal battle that reshaped his views on resilience and integrity, Jeff now channels his experience into...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Mike Brumagin is a U.S. Army veteran, West Point graduate, and co-founder of Battle Monument Group, a private real estate investment firm specializing in single-tenant net lease properties. After earning the Bronze Star for his leadership during Operation Desert Storm, Mike spent over a decade building and managing national restaurant franchises before shifting his focus to real estate. At Battle Monument Group, he has led the acquisition of more than 100...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Patrick E. Alcorn is a business strategist, veteran, and leadership coach committed to empowering entrepreneurs and organizations. As Director of the Veterans Business Outreach Center, he supports military-connected business owners at every stage of growth. A former combat engineer and West Point graduate, Patrick applies strategic thinking and leadership to drive economic development and innovation. He founded Business Beyond the Battlefield...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Schuyler Williamson is an accomplished leader with a background in business, real estate, and mentorship. A West Point graduate and former college baseball player, he brings a competitive mindset and strategic approach to every endeavor. As the founder of Williamson Group Real Estate, he has built a thriving business as a real estate professional, investor, and entrepreneur. As the author of The Steady Leader, Schuyler shares his expertise in...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Claude Burns is a visionary entrepreneur, veteran, and startup founder transforming the workplace food and beverage industry. A former Navy Officer, he brings a mission-driven approach to leadership, strategy, and innovation. As the Founder and CEO of Office Libations, he is redefining B2B food service with a tech-driven model that optimizes inventory, reduces costs, and enhances service. Competing with industry giants, Office Libations has rapidly...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ Corey Reiser is a former Army Artillery Officer, real estate investor, and founder of School of Grit. A Division I lacrosse player at the U.S. Military Academy, he built the discipline and resilience that shaped his career. After leaving the military, Corey applied those same principles to real estate, creating a successful portfolio and achieving financial freedom at a young age. Through School of Grit, he shares hard-earned lessons on mental toughness,...
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Need financing for your next investment property? Visit: Want to join us in San Antonio, TX on June 11th & 12th? Visit: ____ David Baska is a dynamic leader with expertise in operations, finance, and strategic planning. As Chief Operating Officer at Swift Brands, he spearheads the company’s mission to revolutionize military-branded apparel and the broader apparel industry through innovative technology and U.S.-based on-demand manufacturing. A former officer in the U.S. Air Force, David served in space and military operations, earning honors such as the Defense Meritorious Service...
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Need financing for your next investment property? Visit: ____ With 33 years of experience, David Chepauskas specializes in solving problems and maximizing opportunities for senior Wall Street professionals, business owners, executives, and retirees. He is a partner at Summit Financial LLC, a leading independent financial planning firm serving the NJ Tri-State area. David is passionate about working with veterans and service academy graduates, leveraging his network to help them achieve their business goals and build meaningful relationships. His expertise spans retirement,...
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Need financing for your next investment property? Visit: https://www.academyfund.com/
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With 33 years of experience, David Chepauskas specializes in solving problems and maximizing opportunities for senior Wall Street professionals, business owners, executives, and retirees. He is a partner at Summit Financial LLC, a leading independent financial planning firm serving the NJ Tri-State area. David is passionate about working with veterans and service academy graduates, leveraging his network to help them achieve their business goals and build meaningful relationships. His expertise spans retirement, estate, insurance, investment, and income tax planning. David’s goal is to provide tailored financial strategies to meet the unique needs of his clients. He enjoys connecting people and fostering professional connections that lead to growth. David’s deep knowledge and personal approach have made him a trusted advisor in his field.
Show Notes:
In this episode of the SABM podcast, Scott chats with David about:
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The Unique Focus of David’s Firm: Tailored wealth-building strategies for academy graduates and veterans.
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Private Markets: The benefits of private equity, private credit, and private real estate, including higher returns and lower volatility.
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Portfolio Allocation: Why diversification is key to successful wealth management.
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Advanced Tax Strategies: Insights into tax-loss harvesting and direct indexing.
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Charitable Giving: Using philanthropy as a tool for managing high income and capital gains.
Timestamps:
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00:49 Introducing the Unique Approach of Summit Financial
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04:02 Diving into Private Market Investments
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09:52 Understanding Portfolio Allocation
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14:42 The Benefits and Drawbacks of Private Investments
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21:50 Exploring Tax Loss Harvesting Strategies
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31:15 Charitable Giving and Estate Planning
Connect with David :
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A special thank you to David for joining me this week. Until next time!
-Scott Mackes, USNA ’01