Earn Your Leisure Podcast — SECRETS to Rockefeller's Trust: How to Create GENERATIONAL WEALTH!

Hosts: Rashad Bilal & Troy Millings
Date: December 26, 2025
Podcast: Earn Your Leisure (iHeartPodcasts)

Overview

This episode of Earn Your Leisure dives deep into the blueprint of generational wealth through estate planning, inspired by the legendary Rockefeller family trust. The hosts and their guest (a seasoned trust and estate planner) break down strategies, real-life implementation, and misconceptions around wealth transfer, using the Rockefeller family as the gold standard. This episode aims to educate listeners on how anyone—regardless of starting wealth—can create, sustain, and multiply family wealth across generations.

Key Discussion Points & Insights

1. The Epiphany: Real Estate and the Power of Trusts

[03:26]

• The guest recounts how understanding living trusts fundamentally changed his legacy planning.
• He draws strong inspiration from both the original 1934 Rockefeller Trust document and the book What Would Rockefeller Do?
• Core idea: Not just leaving assets, but structuring them for growth and longevity.

"I understood the value of having real estate and wanting to hand it over to my legacy... but once I actually went to create a living trust and I saw what it can do, that's when I knew I had a bigger narrative I needed to share with the people."
— Trust and Estate Planner [03:26]

2. Compound Interest & Staggered Distribution

[04:00]

• Outlines setting aside properties, liquidating others, and placing proceeds into a brokerage account under the trust.
• Immediate family receives main properties and life insurance; grandchildren and future generations benefit from compounded interest.
• Uses a 6% annual rate to illustrate dramatic long-term growth.

"Let's use the example of a million dollars... put a million dollars in a brokerage account for my grandkids. They don't get that till they turn 21, gaining 6% interest... turns into about $3.8 million for my grandkids... they wouldn't get it all, they would get half."
— Trust and Estate Planner [04:36]

• Each new generation leaves half untouched, letting it grow further, mirroring the Rockefeller structure.
• The trust multiplies by combining disciplined access, time, and financial literacy.

3. Multi-Layer Trust Structures—Rockefeller’s “Trust on Trust”

[06:30]

• Rockefeller’s genius: Each child creates their own trust, adding layers of asset protection and compounding.
• This results in multiple streams hitting each future generation, amplifying security and growth.

"What Rockefeller did is... each child opened up a trust. So now his children had a trust... that's twice. Now his grandchildren, so his great-grandchildren would get paid three times... Trust paid out now, 11 generations and counting."
— Trust and Estate Planner [06:41]

4. The “Family Bank” via Life Insurance

[07:13]

• Every trust member also carries a life insurance policy, ensuring liquidity upon death that immediately reinvests into the trust.
• The trust becomes a self-sustaining family bank, funding businesses through trustee-managed loans.

"Any one of my children or grandchildren who want to start a business, what do they do? Talk to the trustees. And now you borrow money. We become our own bank."
— Trust and Estate Planner [07:23]

5. Adapting Trusts for Modern Times

[07:37]

• The guest describes updating his trust terms: lowering access ages and enabling business seed money for minors who can present a viable plan.

"I retreat, retweaked my trust... it was 21, I changed it... to get money at 18, and they can have a business started at 11. Because now with technology, kids are figuring out new ways to start a business."
— Trust and Estate Planner [07:49]

6. Overcoming Mental and Cultural Roadblocks

[08:06]

• Addresses the taboo around life insurance and inheritance, especially in various communities.

"When people say, I don't have the money to do this, you know what I tell them? Yes, you do. The air you breathe is money. A life insurance policy, soon as you die, you're worth money."
— Trust and Estate Planner [08:06]

• Emphasizes mindset shift: legacy-building is everyone’s responsibility.

7. Technical: Life Insurance, Wills, and Trust Costs

[14:05 – 16:36]

• Advises on structuring life policies: separate coverage for debts (mortgages) vs. legacy-building.
• Difference between revocable (flexible, can alter) and irrevocable (fixed, for specific purposes) trusts.
• Pour-over will: catches any assets not already in the trust.
• Price transparency: starting a trust can range from $3,000 to $6,000; complex cases more.

"My first trust cost me about $12,000. My newest one cost me almost 20,000 because I have a lot of things to fund it with. But a starting out trust probably run you anywhere from three to $6,000."
— Trust and Estate Planner [15:35]

8. Managing Assets: LLCs and Funding the Trust

[17:02]

• Smart legal structuring: The trust should directly own holding companies (LLCs), which own real estate.
• If the trust owns the LLC, assets automatically pass into the trust—avoiding funding each property one by one.

"Your holding LLC should be in the name of your trust. So if something happens to you, the properties automatically fall into the trust."
— Trust and Estate Planner [17:15]

9. Family Conversations & The Emotional Legacy

[18:00]

• Stresses open communication with heirs so the vision survives.
• Recommends a "letter of trust": a handwritten, signed letter for each generation to receive.

"I want this copy of this letter in my handwritten form and my signature be copied for every generation, every trustee, so they could look and go, he thought about me... that's powerful."
— Trust and Estate Planner [18:42]

10. Sustainable vs. Generational Wealth—Avoiding Pitfalls

[19:45 – 20:48]

• Warns against assuming children want to be landlords or manage inherited assets as intended.
• Suggests flexible plans: if heirs don't want real estate, liquidate and invest for future compounding.

"We need to stop, you know, really projecting our wants and needs on children and grandkids when they like, yeah, I got my own plan."
— Trust and Estate Planner [20:41]

Notable Quotes & Timestamps

• "When I tell people, when I speak to you, I'm not speaking to you. I'm speaking to your legacy. You're just a vessel..."
  — Trust and Estate Planner [07:59]
• "You have to look at the big picture. But I started out having a plan and I really, really was adamant about getting this structure done. That was it for me."
  — Trust and Estate Planner [15:35]
• "We can't assume that they [our children] would be landlords... That destroyed me because I knew what his objective was."
  — Trust and Estate Planner [20:02]

Key Timestamps for Main Content

• [03:26] – The power of trusts; Rockefeller’s trust inspiration
• [04:36] – Compound interest over generations
• [06:30] – Rockefeller’s layered trust structure
• [07:13] – The family bank: life insurance strategies
• [07:49] – Adapting trusts for young entrepreneurs in the family
• [08:06] – Confronting cultural resistance to life insurance and estate planning
• [14:05] – Life insurance, revocable vs. irrevocable trusts, costs
• [17:02] – Structuring LLCs under trusts
• [18:00] – Family communication and "letter of trust"
• [19:45] – Sustainable vs. generational wealth; pitfalls

Final Thoughts

The heart of this episode illustrates that true generational wealth is not just about assets, but about structure, discipline, education, and intention. The Rockefeller method—living trusts, compounding interest, staggered inheritance, business funding, and life insurance as capital—can be tailored by anyone willing to plan and act. The biggest barrier is mindset; the process starts with believing your legacy is worth the effort to protect and grow.

"You're just a vessel for me to get the message to you so you can hear the message and see it and it reverberates in your brain. And as it's doing this, you literally are talking to your legacy while I'm speaking, going, I got you. Don't worry."
— Trust and Estate Planner [08:00]

For listeners who want to act: Start with education. Find a knowledgeable attorney, outline your long-term plans, regularly communicate with family, and above all—think beyond just your children. Plan for your legacy.