About Expedition Equity
Our Focus
Expedition Equity is a private investment platform focused on allocating capital across select private market opportunities, including real assets, operating businesses, and alternative strategies. Our focus is on situations where structure, execution, and alignment have a greater impact on outcomes than short-term market movements.
Investment Philosophy
We operate outside public markets where inefficiency, complexity, and longer time horizons can create opportunity for disciplined capital.
Our approach emphasizes rigorous underwriting, thoughtful structuring, and alignment with experienced operating partners. Each opportunity is evaluated on its own merits, with an emphasis on understanding risk before return.
Rather than pursuing volume or broad exposure, we allocate capital selectively — prioritizing downside awareness, durability of cash flows where applicable, and long-term value creation across market cycles.
Our team brings experience across business ownership, real assets, healthcare, and private markets, applying precision and judgment to how capital is deployed and stewarded over time.
How We Invest
Rigorous Due Diligence
Every deal undergoes detailed financial, market, operational, and risk analysis.
Selective Partnerships
We only partner in sectors and geographies we know deeply, where we can add value.
Active Oversight
We stay engaged post-close, ensuring execution aligns with projections.
Thoughtful Structuring
We design investment structures with alignment, simplicity, and tax considerations in mind.
Skin in the Game
We invest alongside our investors to ensure alignment of interests.
Our Core Values
Integrity
We put your interests first. No hidden fees, no conflicts of interest. Every decision is guided by a fiduciary mindset.
Excellence
We hold ourselves to high standards across underwriting, operations, and oversight, with a focus on consistency and execution.
Transparency
Clear and timely communication is a priority. We believe investors should understand how capital is positioned and how decisions are made.
Innovation
Markets evolve; so do we. We stay ahead of trends, push boundaries, and adapt to new opportunities.
Firm Leadership
Dr. Dylan Reach
Founder & Managing Partner
Dr. Reach is responsible for investment strategy, underwriting oversight, and capital allocation at Expedition Equity.
His background includes building and operating multi-location businesses, evaluating real asset and operating company investments, and navigating private market structures across multiple asset classes. This experience informs a disciplined, risk-aware approach to opportunity selection and partnership evaluation. His early career in healthcare also shaped a process-driven, analytical approach to risk and decision-making.
At Expedition Equity, he focuses on aligning capital with experienced operators, structuring investments thoughtfully, and stewarding investor capital with a long-term perspective across market cycles.
Caitlin Day
Investor Relations
Caitlin Day supports investor communications and relationship management at Expedition Equity. She serves as a primary point of contact for investors, helping coordinate onboarding, updates, and ongoing engagement across the firm’s investment offerings.
In addition to investor relations, Caitlin assists investors who choose to invest through self-directed IRAs by helping coordinate account setup and investment execution with third-party custodians. She supports the process and logistics of SDIRA investing, ensuring a smooth and efficient experience while working alongside custodians and administrators.
Caitlin works closely with leadership and operating partners to support transparency, responsiveness, and long-term alignment with the firm’s investor base.
Gray Reach
Investment Associate
Gray supports sourcing, due diligence, financial modeling, and portfolio analytics across Expedition Equity’s investment strategies. He plays a key role in evaluating opportunities, supporting underwriting, and assisting with ongoing asset oversight.
In addition, Gray works with investors on tax-advantaged planning strategies, including the implementation of cash value life insurance solutions. As a licensed insurance agent, he helps investors evaluate and structure these policies as part of a broader, long-term capital strategy.
Donita Cocal
Administrative Coordinator
Donita supports the firm’s day-to-day operations, ensuring coordination, organization, and execution across internal teams and external partners. She plays a key role in maintaining operational efficiency, supporting investor communications, and assisting with the preparation of marketing materials, presentations, and internal reporting.
Known for her reliability, attention to detail, and strong follow-through, Donita helps keep projects moving smoothly and ensures the Expedition Equity team operates with consistency, professionalism, and alignment.
Fund Administration & Operations Support
Seth Bradley
Brittany Barchalk
Christina Santos
Daniel Beccara
Jerro King
This team supports fund administration, investor onboarding, reporting, and operational execution under the direction of Expedition Equity’s leadership. They do not make investment decisions or allocate capital, but ensure accuracy, timeliness, and compliance across administrative and reporting functions.
Embark On Your Wealth Building Expedition
Building wealth doesn’t require risking it all or putting your hard-earned savings in jeopardy.
At Expedition Equity, we invite you on a journey to wealth through secure, high-yield real estate investments in thriving U.S. markets.
Every commercial real estate investment we offer is meticulously examined, personally curated to align seamlessly with your unique financial aspirations and investment objectives.
Meet Your Guides
Dylan Reach
Founder of Expedition Equity
I’m a practicing Optometrist with a passion for both creating a positive impact and sustainable wealth building. Since I started my own practice and expanded it to multiple locations, I found myself yearning for a change. Along the way, I steadily invested in real estate and was seeing the potential for replacing my income and creating generational wealth simultaneously.
I knew I needed to transition away from the demanding life of owning a medical practice to spend more quality time with my family and explore my deep-seated passion for helping others build wealth. In my family, entrepreneurship runs deep. My kids, too, share this spirit, and I find immense joy in supporting their budding business ventures.
My venture into real estate began with a bold step - converting our first home into a rental property. This ignited my curiosity for real estate, and soon I was navigating the complexities of 1031 exchanges.
But my real estate journey didn't stop there. I ventured into commercial real estate, keeping my initial commercial property as a rental while scaling up my practice. The desire for diversified wealth strategies led me to explore short-term rentals and eventually delve into real estate syndications.
The freedom I’ve experienced through my investments has changed my life. And I can’t wait to help you experience the same.
Caitlin Day
Investor Relations
Caitlin joined Coldwell Banker in 2020, finding that Real Estate was where her talents and skills merged with her love for serving others.
Working as a full-time real estate agent didn’t leave much time for planning the financial future of her family.
Caitlin found the perfect fit with passive real estate investing, allowing her to build wealth alongside like-minded individuals while balancing her roles as a mom and professional.
Excited for the opportunity to merge her love for Real Estate and helping others, Caitlin joined the Expedition Equity team in 2024. Whether you are looking for your dream home in South Georgia, or want to take advantage of the many benefits of real estate investing, she’s ready to help you on your journey.
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