Most business owners already have the advisors. A CPA, an attorney, a financial advisor, an insurance professional. What they rarely have is a team. In this episode of the Business Legacy Podcast, Paul Dio sits down with Dale Montgomery, founder of TRS Family Office, to unpack why siloed advice quietly drains a business owner's bandwidth and how a collaborative advisory model changes the trajectory of both the business and the family behind it.

Dale's path to this work was forged in loss. After more than 20 years in real estate, building a brokerage and a portfolio of investment properties, the 2008 financial crisis wiped out nearly everything, including his family's hobby farm. That experience led him into the financial side of insurance and eventually to the virtual family office model, which he joined in 2021 after first discovering it in 2019. Today his firm brings together 75 vetted specialists across tax planning, risk management, wealth and legacy, legal services, and business advisory.

The conversation traces the family office concept back to John D. Rockefeller, who stopped taking advice in silos and required his advisors to collaborate as one team. Dale explains how that model, once reserved for the ultra wealthy, is now accessible to owners with a six figure tax bill or at least a million dollars in gross revenue. He also shares a powerful case study on the difference between EBITDA and enterprise value, showing how a business with strong cash flow can still be nearly worthless to a buyer if every key relationship walks out the door with the owner.

For entrepreneurs thinking about legacy, Dale's contrast between the Vanderbilts and the Rockefellers lands with clarity. One family passed down assets. The other passed down a way of thinking. His advice is to prepare your business for sale long before you plan to sell, build wealth outside the business, and leave your family a mindset strong enough to create wealth again.

00:00 Welcome and introduction to Dale Montgomery

01:00 Growing up in White Bear Lake and 20 years in real estate

02:00 Losing everything in 2008 and finding the virtual family office

03:30 Why business owners hit a plateau

05:00 Who Not How and the power of delegation

06:30 The Rockefeller history of the family office

08:30 From ultra wealthy to accessible, the virtual family office

09:30 Working with an existing CPA and advisory team

11:00 The five area diagnostic

12:30 Legacy planning, succession, and exit options

13:30 EBITDA versus enterprise value case study

15:30 Best decision, persistence

16:30 Worst decision, not building wealth outside the business

18:00 Real estate, debt, and today's economy

21:00 Trusting your gut in uncertain markets

22:30 The most gratifying part of the work

23:30 Vanderbilts versus Rockefellers

26:00 Teaching kids growth without self condemnation

28:00 Where to connect with Dale

Discover how Dale helps established business owners replace siloed advice with a collaborative team of specialists that protects their wealth, strengthens their business, and prepares them for a stronger exit: https://trsfamilyoffice.com

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