This Business Could 5X… But It’s Targeting The Wrong Customers (Dale Montgomery Interview)

Abi Asija interviews Dale Montgomery, Director of Advanced Planning at TRS Family Office, about building a virtual family office business designed to help small and mid-sized business owners access high-level financial strategies typically reserved for the ultra-wealthy. From tax mitigation to exit planning, Dale explains how his model brings together multiple specialists under a single, coordinated system.Key takeaway: the fastest path to growth is focusing on the right customer, and in this case, CPAs are the real leverage point, not business owners.Dale explains the virtual family office concept, inspired by how families like the Rockefellers structured their wealth by having all advisors collaborate under one roof. His model brings that same approach to business owners by covering five key areas: tax planning, risk mitigation, wealth and legacy planning, legal services, and business advisory services.Instead of business owners managing disconnected advisors, Dale acts as the architect, coordinating over seventy-five vetted specialists to create a unified strategy. This eliminates blind spots and helps clients increase cash flow, reduce taxes, and build long-term enterprise value.One of the biggest challenges, however, is explaining this complex model in a simple way. Business owners often do not realize they have a problem, making the sales process slower and more difficult despite the value being clear.Abi identifies the core issue immediately. Dale is targeting business owners directly, when the better strategy is partnering with CPAs who already have trusted relationships with hundreds of clients. One CPA relationship can unlock massive deal flow, making it a far more scalable growth channel.They break down the numbers. Dale currently works with five to six clients and generates around two hundred thousand dollars annually, but his goal is to reach seven figures by scaling through CPA partnerships. Each CPA can bring access to one hundred to five hundred business owners, creating exponential growth potential.The conversation dives into how Dale monetizes the business. He charges an annual proactive planning fee starting at thirty-six hundred dollars, with most clients choosing the fifty-six hundred dollar tier for ongoing advisory. Additional revenue comes from implementing strategies like tax mitigation, where clients can save tens of thousands, and the team shares in the upside.They also explore real use cases, including reducing tax burdens, optimizing legal structures, preparing businesses for sale, and increasing valuation multiples. One example highlights how shifting from owner-dependent revenue to diversified contracts increased a company’s value by tens of millions.Another key insight is the power of collaboration. Traditional advisors operate in silos, while Dale’s model ensures every decision is aligned across tax, legal, and financial strategies. This creates both financial gains and peace of mind for business owners.On the growth side, Dale shares his current strategy of networking, podcasting, and even hand-delivering “tax season survival kits” with his book to local CPAs. While creative, Abi pushes for a more focused approach by building an irresistible offer specifically for CPAs that emphasizes easy implementation, zero risk, and additional revenue.The conversation closes with Dale sharing how viewers can connect with him through his website trsfamilyoffice.com or by email, as he continues building partnerships with CPAs and expanding his virtual family office model nationwide.