Wealth On Main Street 280: How Legacy Planning Protects Your Family’s Generational Wealth with Shane Stirling
If you're building something meaningful, a business, a legacy, a future for your kids, then you've likely asked yourself: How do I ensure this wealth doesn't vanish in a generation or two?
Honestly, it’s a question more families should be asking.
On a recent episode of the Wealth On Main Street, entrepreneur Shane Stirling joined Jayson Lowe and Richard Canfield to share his deeply personal and inspiring journey through estate planning, wealth preservation, and legacy building.
What makes Shane's story different is that he isn’t speaking from theory. He’s lived through the transition of generational business ownership, learning through both experience and mistakes.
The lessons he shares are ones every aspiring financially independent family should hear.
Start With Honest Conversations About Legacy Planning
Shane’s passion for estate planning began at home, through real conversations and hard-earned lessons with his family. “Estate planning is a passion,” Shane said. “I love doing it so much, even though I’m no professional.”
That passion came from navigating family dynamics, watching generational transitions unfold, and making decisions not just with spreadsheets, but with heart.
What truly lit that spark? Shane discovered two books that changed his outlook: True Wealth by Thane Stenner and Leaving a Legacy by David Bentall. These weren’t typical how-to guides. They were stories about ultra-high-net-worth families navigating generational transitions.
“They referenced families like the Rothschilds. Shirt sleeves to shirt sleeves in four generations. If you don’t do the work up front, you can’t be upset when it fails later.”
What hit Shane hardest was the idea that generational wealth requires generational wisdom. You can’t protect a legacy without a clear mission, without conversations around values, and without acknowledging that stories, not just spreadsheets, carry meaning.
By talking openly about his own estate plans with family and friends, Shane began encouraging others to do the same, because legacy is a conversation.
Don’t Wait—Start Legacy Planning Early
In 2008, Shane and his brother Dustin were both still in the trades when they discovered their father was planning to sell the business.
That reality check changed everything. They realized if they didn’t step up, the opportunity to build generational wealth would vanish.
“We didn't want the headaches we saw our father deal with. But we also didn't want to be left behind.”
That was the turning point. They moved quickly to put an estate freeze in place and created family trusts. It wasn’t elegant. Mistakes were made. But Shane insists the key was getting started.
“Our father didn’t want to grow a business he wasn’t getting a share of the equity from. So he insisted on retaining a third ownership in the new entity. Even back then, I knew that wasn’t ideal, but he wouldn't budge.”
The structure they created taught them their first big lesson: ownership matters.
Who owns what, and how they own it, shapes everything from tax obligations to decision-making power.
That early experience also introduced them to trusts, dividends, and advanced planning tools. Over time, they refined their strategy, performing another estate freeze in 2013 and setting up a trust for their father.
“There’s no such thing as a true loss,” Shane says. “A wasted mistake—that’s a failure. If you do something wrong and learn from it, it’s a gift. If you never learn, that’s the real cost.”
Structure Your Business With Purpose
Family and business don’t always mix well unless you have intentional boundaries and clear roles.
Shane and his brother Dustin found success not by avoiding conflict, but by embracing their differences and designing a structure that played to their strengths.
“Dustin is operations. He’s the COO, the CEO. He’s got that fact-finder, follow-through DNA. Me? I’m a strategist. I start things fast, but I move on quickly,” Shane explains.
The way they divide responsibilities mirrors a parenting dynamic.
“In our business, Dustin is Dad, and I’m Mom. When someone gets on Dad’s bad side, they come to me. But if I protect them too much, I disrupt the system.” That level of self-awareness has been key to building trust and avoiding unhealthy overlap.
This kind of structure takes emotional maturity. Instead of micromanaging or stepping on each other’s toes, they respect the lanes they've chosen.
Dustin handles operations and personnel. Shane focuses on business development, investments, and broader strategy. “I stay out of the daily grind. That way, we don’t clash.”
Their setup also prevents team members from playing them against each other. “It’s like raising kids. Employees know who handles what. We keep a united front.” This kind of clarity protects the family bond while allowing the business to grow.
When roles are unclear, resentment builds. But when strengths are acknowledged and responsibilities are assigned with intention, family-run businesses can thrive.
Life Insurance is the Ultimate Legacy Shield on Legacy Planning
When it comes to protecting generational wealth, few tools are as powerful or as underestimated as life insurance. For Shane, it wasn’t just a piece of the puzzle. It was the safeguard that kept the whole plan from falling apart.
“We secured a $2.1 million death benefit, just enough to cover the taxes on his preferred shares,” Shane recalls. “The premiums felt outrageous at the time, but that policy saved everything.”
Initially, Shane’s father resisted, haunted by negative experiences with policies in the past. But when the time came, the insurance payout provided a critical lifeline.
It allowed Shane and his brother to redeem shares, manage taxes, and protect the business without selling assets or taking on emergency debt. “If he had passed 10 years earlier, we would’ve been sunk. That payout bridged the gap.”
Beyond traditional coverage, Shane implemented an IFA (Immediate Financing Arrangement), enabling the business to finance a larger policy while maintaining liquidity.
This creative approach gave them access to capital without compromising growth.
Life insurance isn’t just about death. It’s about control, continuity, and peace of mind. Without it, families risk losing more than money. They risk the future.
Shane’s message is clear: don’t wait, don’t cut corners, and don’t underestimate what this one move can do for your family legacy.
Legacy Planning: Talk About Your Will Before You Die
Shane doesn’t hold back when it comes to one of his biggest frustrations: the secrecy around wills. “Why is the document that determines what happens after you die the most hidden one in the house?” he asks.
He believes your family deserves to know your intentions. Without that knowledge, even the most well-structured estate plan can fall apart.
“You’re setting your family up for failure if you don’t talk about the ‘why’ behind the decisions,” he insists.
He recommends two powerful reads: Every Family’s Business and Willing Wisdom by Tom Deans.
These books argue for open dialogue between generations. Shane took that advice seriously. He pushed through resistance, especially with his father, to have tough but necessary conversations.
Those talks led to real action.
- They put life insurance policies in place.
- They created multiple wills to separate personal and business matters.
- They structured share redemptions to minimize tax liabilities.
Perhaps most importantly, they agreed on the family values driving those decisions.
“If your heirs don’t know the story behind your will, it becomes just another document. But if they understand your intentions, it becomes a map.”
Estate planning is more than asset division. It’s a chance to pass down wisdom, and that only happens if you speak up before it’s too late.
Legacy Planning: Create a Family Governance System
Building generational wealth isn’t just about money. It’s about philosophy, storytelling, and creating a shared identity. One of Shane’s proudest initiatives is the creation of a family crest, complete with a motto and symbols representing their values.
“My dad was the beginning of a new line of Sterlings,” Shane explains. “We created this crest with him before he passed. Now, it binds our family together.”
They also talk about financial concepts with their teenage son, ensuring he understands not just what exists but why it exists. “We don’t hide that there are resources. But we don’t give numbers. We talk about responsibility.”
Define the Rules of Family Wealth
One concept Shane promotes is separating money into three buckets:
- Personal money
- Children’s money
- Family money
Each serves a different purpose and comes with different expectations. For instance, his son has a life insurance policy started on his behalf.
“It’s not so I can replace him. It’s to give him a foundation he can build on. One that, if funded throughout life, could be the backbone of everything.”
Shane also talks about future expectations: “We might pay for university. But if you drop out, you pay us back. If you graduate and start a business, we may forgive that debt. But nothing is free. You’ve got to put back in.”
Tell the Stories That Keep It Alive
Legacy is much more than dollars and documents. It’s a living, breathing narrative.
“If you don’t tell the story, the value gets lost,” Shane says. In his view, the real meaning behind wealth, whether in heirlooms, insurance policies, or family businesses, only survives when it’s explained.
Without the why, the what often becomes irrelevant.
Shane believes storytelling is the missing link in most estate plans. Assets are passed on, but values and intentions rarely are. That disconnect leads to confusion, resentment, or worse, mismanagement of the very legacy someone worked a lifetime to build.
“Who’s going to be your family’s storyteller? If it’s not you, it better be someone else,” he warns. It’s a role too important to leave unfilled.
He imagines a future scene: a family gathered around a campfire 50 years from now. They share stories about the man who started it all. Not just what he left behind, but why he did it.
Hopefully, they say, ‘Wow, he really thought ahead.’ But mostly, I hope they’re grateful and committed to carrying it on.”
Legacy is preserved through meaning, purpose, and stories that endure. If you want your efforts to last for generations, don’t just plan the financial side.
Make the story unforgettable.
Conclusion
Legacy is a story. If you don't tell it, someone else might tell it wrong, or not at all.
Whether it's a treasured heirloom, an insurance policy, or a company built from the ground up, its meaning fades if the next generation doesn’t know why it matters.
You don’t have to be a millionaire or a business owner to need legacy planning. As Shane’s story proves, you just need to care about the future of your family.
Planning, communication, and a sense of purpose can protect wealth far better than secrecy and hope ever could.
What will your family say about you one day?
Start writing that chapter now and tell the story before it's too late.
To hear the full conversation and more inspiring episodes, tune in to the Wealth On Main Street podcast.
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