What Do You Know About a Virtual Family Office? We’re Helping One Brand Take Their Story of a Holistic and Strategic Approach to Wealth Management and Asset Protection to Ultra-High-Net-Worth Individuals and Business Owners in the U.S.
For many ultra-high-net-worth individuals and successful business owners, the real challenge isn’t finding good advisors—it’s getting those advisors to work together in a way that protects what they’ve built and supports the legacy they want to leave. Too often, tax, legal, risk management, and wealth strategies move in different directions, creating gaps that show up in missed opportunities, unexpected liabilities, and unnecessary stress. TRS Family Office exists to close those gaps through a virtual family office model that brings proactive, holistic planning to the forefront, and Back2Basics is proud to stand beside them as their fractional CMO, helping share this story with the people who need it most.
The Story Behind TRS Family Office
TRS Family Office was born out of lived experience, not theory. In 2008, founder Dale Montgomery watched the financial crisis unfold from the front row as families lost homes and business owners saw decades of work vanish almost overnight, and he personally lost a 10-acre hobby farm and several investment properties. That season reshaped his purpose, pushing him to shift from real estate into financial planning so he could help business owners protect what they have worked so hard to build.
During his time with the National Federation of Independent Business (NFIB), Dale came to deeply appreciate how central small and closely held businesses are to the economy, knowing that a large share of the nation’s workforce is employed by small businesses. He saw that every owner’s decisions ripple out to affect employees, families, and communities, and he began searching for a better way to support those owners more holistically. That search eventually led him to the virtual family office model, which became the foundation of TRS Family Office and inspired him to write The Virtual Family Office Advantage.
Dale’s Expertise and Vision
Dale realized that most successful business owners don’t suffer from a lack of advisors; they suffer from a lack of coordinated planning. Their CPA, attorney, financial advisor, insurance professional, and other specialists may each be highly capable, but they are often focused on separate pieces of a complex puzzle, leading to fragmented advice rather than a unified strategy. This insight drives his work today: creating a system where advanced planning is integrated, proactive, and aligned with an owner’s long-term goals for wealth, tax mitigation, risk, and legacy.
In The Virtual Family Office Advantage, Dale lays out key pillars of this ecosystem, including strategic tax planning, risk management, wealth building, legal frameworks, and business advisory. He emphasizes the importance of a “hub-and-spoke” model, where a proactive planning team coordinates “best-of-breed” tax, legal, and financial experts on behalf of the client. TRS Family Office’s mission is to help their best clients unlock their full financial potential by offering forward-looking advice, proactive guidance, and value-added solutions designed to exceed expectations.
The Power of a Virtual Family Office
The virtual family office concept grew out of traditional family office structures used by prominent families and has since evolved to serve modern business owners and individuals who need similar coordination without the cost and complexity of building an in-house team. Today’s virtual model brings that level of coordination, clarity, and strategic thinking within reach for ultra-high-net-worth individuals and successful entrepreneurs. Instead of adding more advisors, the virtual family office focuses on aligning the right specialists around a single, cohesive plan.
At TRS Family Office, this approach is delivered through two aligned teams: a Proactive Planning Team, which serves as the client’s first point of contact for strategic direction and coordination, and a Virtual Family Office network, which provides access to top-tier expertise across tax, legal, risk management, and financial disciplines. For clients, this structure can strengthen wealth-building strategies, support more intentional tax mitigation, and enhance liability reduction by ensuring every decision is evaluated through a coordinated lens rather than in isolation. As wealth and businesses grow more successful and planning becomes more complex, TRS Family Office helps clients make more confident, strategic decisions about growth, protection, and succession.
Who Does TRS Family Office Serve?
TRS Family Office is built for people whose financial lives have become too complex for piecemeal or siloed advice. It is especially well-suited for ultra-high-net-worth individuals and business owners who want a more intentional, coordinated approach to their planning.
Individual wealth holders
These are people whose personal wealth has grown through investments, ownership stakes, executive roles, or other high-earning careers. They often juggle multiple accounts, properties, and investment strategies, and they want to be sure every decision supports long-term security and impact.Business owners and entrepreneurs
Business owners face unique challenges, from managing cash flow and tax exposure to protecting what they’ve built and planning a future transition. TRS Family Office helps them align business and personal planning so that growth, risk management, and exit strategies work together rather than against each other.Multi-generational families
Some clients are thinking not just about their own needs, but about children, grandchildren, and future generations. They want structures that preserve wealth, reflect their values, and encourage responsible stewardship over time. TRS Family Office supports this kind of legacy planning with coordinated tax, legal, and advisory input.
By speaking directly to these three groups, TRS Family Office makes it clear that the virtual family office model is not just for one type of client—it is for anyone whose success has created complexity and who is ready for a more holistic, proactive way to manage their wealth and legacy.
Goals for TRS Family Office
Looking ahead over the next five years, Dale sees TRS Family Office partnering closely with CPA firms that want to become more holistic, proactive, and valuable to their best clients. By helping these firms bring advanced planning in-house through a coordinated virtual family office model, TRS can strengthen both the advisory practices and the businesses they serve.
In the next decade, Dale envisions hundreds of business owners and individuals becoming empowered to make better decisions by benefiting from coordinated planning rather than fragmented advice.
His goals go beyond individual outcomes; he is focused on the broader ripple effect. When clients keep more of what they earn, protect what they have built, and transition their companies or estates on their own terms, they can provide more stable careers, hire more people, and reinvest in their communities. Dale measures success not only in tax savings and balance sheets, but in stronger families, healthier local economies, and legacies that last beyond the current generation.
How Back2Basics Elevates the TRS Brand
Back2Basics is honored to serve as the trusted fractional CMO for Dale and the team at TRS Family Office, helping them articulate and amplify the value of the virtual family office model. As a brand management partner, Back2Basics is focused on aligning TRS’s brand vision and messaging so that ultra-high-net-worth individuals and business owners begin to understand the framework around a virtual family office and clearly see how the coordinated planning within that framework can transform their financial future. This includes developing educational content rooted in Dale’s thought leadership, refining TRS’s visual and verbal identity, and ensuring every touchpoint reinforces their core themes of clarity, stewardship, and legacy.
By translating complex planning concepts into approachable stories and frameworks, Back2Basics helps TRS Family Office stand out in a crowded advisory landscape where many firms still operate reactively.
Together, they are building a brand narrative that highlights proactive tax strategies, risk management, and long-term wealth-building as part of a single integrated virtual family office experience. As TRS continues to grow, Back2Basics will support targeted outreach to potentially partnering CPA firms, business owner communities, and ultra-high-net-worth individuals who are ready for a more holistic approach to planning.
Invitation to Ultra-High-Net-Worth Individuals and Business Owners
Dale Montgomery and TRS Family Office are inviting ultra-high-net-worth individuals and business owners who are tired of piecing together fragmented advice to explore the structure and benefits of a virtual family office. For those seeking stronger wealth-building strategies, more intentional tax mitigation, and meaningful liability reduction, TRS offers a coordinated planning experience designed to align personal and business goals over the long term.
Readers are encouraged to reach out to Dale and the TRS Family Office team to discuss how a virtual family office model can help them unlock their full financial potential and protect the legacy they are building.
