In a world of ever-shifting markets and complex financial instruments, the concept of keeping your investments close to home—both in terms of geography and values—has taken on renewed significance. Homegrown Holdings, a boutique real estate investment firm based in Metro-Lexington, KY, stands at the forefront of this movement. Under the leadership of its founder, Whitney Shepherd, the firm champions investments that not only promise attractive returns but also reflect the unique priorities and aspirations of each family it serves.

At its heart, Homegrown Holdings embraces a family-led value-driven investment philosophy. It weaves together the threads of integrity, innovation, and generational stewardship to create a tapestry of opportunities tailored to the long-term well-being of families. By focusing on real estate assets—particularly multifamily properties—this firm demonstrates how sound financial decisions can elevate communities and build enduring legacies.

Defining the Homegrown Investing Approach

Whitney Shepherd’s journey began with a background in chemistry and a growing passion for finance, design, and real estate. After an extensive search for an established business with $1 million EBITDA, she pivoted to acquiring a value-add multifamily property outside Lexington, KY. This decision laid the foundation for Homegrown Holdings’ signature strategy: pursuing long-term hold real estate investments that enhance both property values and tenant experiences.

Rather than chasing speculative flips or high-risk ventures, Homegrown Holdings maintains a disciplined focus on upgrading amenities, improving energy efficiency, and fostering vibrant communities. Each acquisition undergoes rigorous underwriting, careful market analysis, and a thoughtfully crafted renovation plan. This approach not only drives consistent rental growth but also contributes to sustainable neighborhood revitalization.

Building a Multi-Generational Legacy

For many families, preserving wealth across generations can feel like navigating a labyrinth of regulations, tax implications, and emotional dynamics. Homegrown Holdings offers a range of family office services designed to simplify these complexities and keep your family’s vision front and center. Some of the core pillars include:

• Personalized wealth management across generations
• Private markets access for equity, debt, and real estate
• Comprehensive estate and trust planning guidance
• Family governance, education, and stewardship programs
• Administrative support: bill pay, reporting, and technology tools

By simplifying complex financial matters through dedicated teams and trusted partnerships, the firm ensures that each generation has clarity, confidence, and a shared sense of purpose. Whether coordinating tax advisory services or organizing annual family assemblies, Homegrown Holdings empowers families to make decisions grounded in their core values.

Diversified Investment Opportunities

While real estate remains the cornerstone of Homegrown Holdings’ portfolio, the broader ecosystem of “homegrown” entities offers inspiring examples of how families can diversify into complementary sectors. From venture-backed consumer packaged goods (CPG) startups to crowdfunding platforms addressing housing shortages, these models illustrate the breadth of possibilities:

As these examples show, families can align their capital with sectors that resonate deeply—be it healthy food, community development, or emerging consumer trends. With minimum investments as low as £500 in some platforms, there is room for every family to explore new frontiers.

Inspiring Case Studies

Consider the Martin Family Office, which began with a few core real estate holdings and gradually expanded into tax planning, philanthropy, and dedicated governance structures. By partnering with external experts—rather than building an entire team in-house—they achieved full-service capabilities without prohibitive overhead. This hybrid model preserved agility while ensuring each family member received personalized guidance.

Another compelling story is that of Annie’s Homegrown, once a small mac & cheese company pitched by Homegrown Holdings Corp in the late 1990s. With strategic support and dedicated capital, the brand scaled to $17 million in sales by 2003 and ultimately sold for $20 million. While Whitney Shepherd’s firm now focuses on real estate, this history underscores the power of building meaningful generational wealth through targeted investments in sectors you understand and care about.

Overcoming Challenges with Governance

One of the most common hurdles families face is internal discord—conflicting visions, communication breakdowns, and uneven responsibilities. Establishing a formal family constitution or charter can mitigate these risks by setting clear expectations, roles, and decision-making protocols. Whether drafting policies on liquidity events or defining philanthropic priorities, such frameworks foster harmony and ensure continuity when leadership transitions.

Educational initiatives—workshops, retreats, and mentorship programs—further prepare the next generation. By blending financial literacy with storytelling about the family’s origins and impact, younger members become true stewards of the legacy rather than passive inheritors.

Embracing Future Trends

Looking ahead, families seeking to preserve and grow wealth must remain agile in the face of evolving opportunities and risks. Key areas to watch include:

• Private equity and debt strategies in emerging markets
• Cybersecurity solutions tailored for family offices
• Sustainable food and beverage investments
• Philanthropic impact driven by data analytics
• Outsourced CFO and compliance partnerships

These frontiers offer new avenues to reinforce your values, drive innovation, and secure returns. By leveraging trusted advisors and staying informed, families can seize these opportunities without losing sight of their core purpose.

Homegrown Holdings is more than an investment firm—it is a partner in your family’s journey toward financial empowerment and lasting impact. By centering decisions on shared values, adopting robust governance structures, and pursuing opportunities across real estate, CPG, and beyond, you can chart a path that resonates with both heart and mind. As you consider the next chapter of your family’s story, remember that the greatest returns often arise when you invest in what truly matters.

Embrace this moment to craft your legacy with intention. Draw upon the lessons of the past, the innovations of the present, and the boundless potential of the future. In doing so, you and your family will not only prosper financially but also leave a mark on communities and generations to come—an achievement that transcends any balance sheet.