Independence by Design™ #458: Brandon Henry | The Business Advice System Is Broken — Here’s the Truth Owners Need
The business advice system is completely broken. Tax, estate, and wealth must be one plan — and you can’t trust the system to build it for you.
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Advisors sell products, optimize for their own fees, and stay in their silos. Taxes here. Estate there. Wealth over in another corner. Nobody owns the whole. And owners are the ones who pay the price.If you don’t take ownership of the plan, you’ll be the one left holding the bag when taxes hit, valuations disappoint, or estate plans fall apart. It’s just like the healthcare system. Specialists cut and prescribe. Nobody’s responsible for keeping you healthy. In business, nobody’s responsible for making sure your entire plan actually works together.
In this conversation with my friend Brandon Henry, who works inside the family-office world of the 0.1%, we tell the truth about how advice really works — and why middle-market owners can’t afford to buy the orchestration back. If you don’t step up as the general contractor of your own plan, you’ll drown in noise, propaganda, and bad advice.
We don’t hold back. We lay out what good looks like, how to spot misaligned incentives, and what it takes to design a plan that actually serves you.
What We Cover:
–Why the business advice system is designed to serve advisors, not owners.
–The healthcare analogy: why the parallels are too obvious to ignore.
–Why there’s no such thing as “three plans” — tax, estate, and wealth are one system.
–The general contractor role every owner must play until you can buy back orchestration.
–How to filter propaganda, spot misalignment, and hold advisors accountable.
–What “good” advice actually looks like — and why it’s so rare.
Who This Is For:
If you’re a business owner tired of piecemeal advice and sales pitches disguised as planning — and you want to finally understand how the game really works so you can take control — this episode is for you.
Chapters:
- (00:00) Introduction and the broken business advice ecosystem
- (04:22) Brandon Henry joins, defining the core pain point
- (09:42) General contractor role, advisor complexity, and misaligned incentives
- (18:15) Income tax compliance versus strategic tax planning
- (26:59) Estate planning versus estate tax planning distinctions
- (40:02) Wealth management industry evolution and fee compression
- (56:58) Being your own general contractor until escape velocity
- (1:08:01) Business structuring and preparing for transactions proactively
- (1:19:31) Transaction readiness, avoiding vultures, and maintaining optionality
- (1:36:40) What the ideal family office experience looks like
- Rate, comment, and share with the owner/operators you know!
Resources:
Mosaic Advisors https://mosaicadvisors.com/
IBD Newsletter on Valuations https://newsletter.ryantansom.com/
Previous Interviews with Brandon Henry:
#416: Behind the Curtain: How Ultra-Wealthy Families Manage Their Business Assets with Brandon Henry https://independence-by-design.castos.com/episodes/416-behind-the-curtain-how-ultra-wealthy-families-manage-their-business-assets-with-brandon-henry
Ep. #350 - What it Means to “Think Like an Owner” Inside the Boardroom of a Privately Held Business https://youtu.be/4WOuI9SdoWw?si=go_zQ1vr6hMST0Hm