Wealth On Main Street 281: Taking Charge of Your Wealth That Lasts Generations with Justin Maxwell
You’ve worked tirelessly to build a thriving business, but there’s a quiet question you carry: Am I just earning a high income, or am I truly building wealth that will last beyond me?
It’s a question that goes beyond bank accounts or investment portfolios. It’s about purpose, legacy, and how you shape the future for your family and the generations that come after you.
In this episode of the Wealth On Main Street podcast, Jayson Lowe and Richard Canfield sat down with Justin Maxwell, a partner at Big Life Financial, to talk about how he transformed his life when he realized much of what he’d been taught about money was designed to keep him small.
Now a partner in a fractional family office serving seven- and eight-figure entrepreneurs, Justin’s mission is to help people like you stop being the highest-paid employee in their own business and start being the architect of generational wealth.
You’ll learn how to align your team, shift your mindset, automate your success, and most importantly, lead with vision and intention.
Let’s break it down.
Rethink Wealth: Leadership Starts With You
Justin, once a schoolteacher chasing the illusion of security, had his worldview shattered when someone asked, “What if everything you were taught about money was designed to keep you stuck?” That question became his wake-up call.
What does that mean for you? It means you can’t sit back and assume your CPA, lawyer, or investment advisor will magically align your wealth plan.
Today, Justin is a partner in a fractional family office, coaching entrepreneurs to step into their true financial leadership role.
“You have to lead your wealth with just as much urgency and passion that you lead your business,” says Justin.
Too often, entrepreneurs blame the government or advisors when things stall. But the real problem is the lack of orchestration when your team members work in silos, inefficiencies, tax burdens, and missed opportunities multiply.
You need to be the orchestrator, the one who defines the vision and ensures everyone on your wealth team is moving in sync toward it.
This isn’t just about more meetings. It’s about stepping into ownership over your financial future, just like you do with your company’s future.
Automate Savings: The Boring Habit That Builds Millions
Where do most entrepreneurs lose wealth?
Surprisingly, it’s not in big, flashy mistakes. It’s in the small, everyday choices they barely notice. “Automate your savings,” Justin advises. “Let computers do it for you. Take away your personal behavior from it.”
This simple yet powerful strategy can help you capture millions over your lifetime that you’d otherwise spend unconsciously.
The key is to set up systems that move money automatically into profits, savings, and spending accounts the moment income hits. This works both on the personal and business side.
While it may not feel exciting, automation shields you from Parkinson’s Law. The tendency for expenses to rise with income.
You won’t be tempted to spend what you never see in your main account.
It only takes about 30 to 60 minutes to set up automated savings, but once in place, it works quietly in the background, accumulating wealth. As Justin explains, automation is about removing temptation.
You still monitor and adjust, but you don’t rely on willpower. Most importantly, automation works best when tied to a bigger purpose, which brings us to the next key: building a compelling vision that excites and guides you.
Build A Bigger Vision To Drive Purpose
Automation only works when you have a clear reason why you’re saving. Many entrepreneurs get caught in the trap of chasing the next opportunity without defining where they actually want to go.
As Justin puts it, “They don’t actually know where they’re going.”
Without a clear, exciting future vision, saving and planning can feel pointless or get deprioritized.
Ask yourself: What would make me feel remarkably happy with my progress three years from now?
This question, known as the R Factor, helps you shift from vague goals like “be successful” to specific, meaningful outcomes. It could be securing your children’s future, supporting causes you care about, or setting your family up for long-term freedom.
Justin emphasizes that the human brain craves specificity. Once you define an inspiring vision, your mind begins working to make it a reality because the brain struggles to distinguish between imagined and actual outcomes.
Without this clarity, it’s easy to fall prey to the latest trends or distractions. But with it, you can confidently direct your savings, business decisions, and team toward what matters most. Purpose drives discipline.
Turn Your Business Into An Asset, Not Just A Job
A major shift in building generational wealth is seeing your business as an asset, not just a job or cash machine.
Too many entrepreneurs treat their companies as ATMs, pulling cash to fund other people’s assets while neglecting to grow their own. But as Justin explains,
“Your business is the centerpiece of all wealth strategy.” To build lasting wealth, you need to maximize the value of what you control.
That means going beyond day-to-day operations. Focus on improving your business’s valuation: reduce expenses, especially taxes; implement solid insurance protection; and protect the company against key risks like death, disability, divorce, or lawsuits.
Plan for how your business can be sold, transferred, or scaled, not just how it can pay you today.
Justin also stresses the importance of entity structure and tax planning, which are too often overlooked or handled in isolation.
When you treat your business as a true asset, you unlock efficiencies, protect wealth, and create growth opportunities that extend far beyond your own lifetime. This is creating something that will endure and support the legacy you want to leave behind.
Break Free From Middle-Class Thinking
Many million-dollar entrepreneurs unknowingly operate with a middle-class mindset, even as their income soars. They work tirelessly, but their vision and their team stay small.
Justin puts it plainly: “The wealth vision is created by the entrepreneur, not the advisor.” In other words, top-tier entrepreneurs lead their advisors toward clear, ambitious goals instead of waiting for someone else to chart the course.
To break free, you need to raise your standards.
Ask yourself tough questions: Are my current advisors equipped to take me where I want to go? Am I playing too small? Surround yourself with professionals who challenge you, not just manage you.
Middle-class thinking says, “I’ll let my advisor handle it.” Wealth-thinking says, “I’ll lead the strategy, and my advisors will help me execute it.”
The key difference is mindset. When you shift from being a reactive business owner to a proactive wealth leader, you unlock opportunities that were always available but hidden by limited vision.
This upgrade doesn’t necessarily require millions more in revenue. It starts with intentional leadership and a commitment to play at a higher level. To truly move forward, you must challenge your beliefs, expand your goals, and elevate the people guiding you.
Build A Generational Wealth Mentality
True generational wealth is passing on a mindset of stewardship, ambition, and resilience. As Justin emphasizes,
“The behaviors are what produce the wealth.” Without the right values, even the largest inheritance can be squandered in a single generation.
Start by sitting down with your spouse, partner, or family and defining what wealth truly means to you. Ask: What do we stand for? What values will guide our decisions today and shape our descendants tomorrow?
Don’t leave this to chance or assume institutions like schools or churches will fill in the gaps. Bring this conversation into your home and make it a foundational part of your family culture.
Create shared principles, clear expectations, and traditions that reinforce your family’s vision. Whether it’s charitable giving, entrepreneurship, education, or service, embed these priorities into daily life.
This is about more than leaving money. It’s about preparing the next generation to carry the torch with wisdom and purpose. By modeling these behaviors now, you give your family a roadmap for success that outlasts any bank account.
Plan With Purpose, Not Just Paperwork
Yes, you need the legal and financial structures — trusts, tax strategies, insurance, succession plans — but none of it matters without purpose.
As Justin wisely notes, “Expectations don’t turn into realities very effectively without having a framework.” That framework must include not just mechanics, but meaning.
- Get clear on your long-term vision. What’s the ultimate purpose of your wealth? What legacy do you want to leave?
- Hold regular family meetings, not just to review numbers but to discuss values, goals, and dreams.
- Teach your children not only how wealth works, but why you’ve worked to build it. Equip them to be wise stewards, not just beneficiaries.
A purposeful plan integrates money with meaning. It aligns estate documents with family conversations, aligns tax planning with giving strategies, and aligns business exits with legacy plans.
Without this integration, you risk leaving behind confusion instead of clarity. When you lead with intention, you transform your wealth from a series of accounts and contracts into a lasting, meaningful legacy that shapes lives for generations to come.
Take Action: Your First Step Toward Generational Wealth
The conversation with Justin delivers a powerful reminder: real wealth is never accidental — it’s intentional, orchestrated, and purpose-driven. It’s not just about accumulating money. It’s about building a future that serves your family, shapes your legacy, and creates ripple effects for generations to come.
- You’ve learned that leadership starts with you, not your advisors.
- You’ve seen how small, automated habits can lead to massive results over time.
- You’ve explored the importance of having a clear vision, treating your business as an asset, and breaking free from middle-class thinking.
- Most importantly, you’ve been invited to redefine wealth as more than numbers to see it as values, behaviors, and a shared family mission.
Start today. Define your family’s wealth mentality, align your team with your vision, and put systems in place to protect and grow what you’re building.
Hold regular family conversations, elevate your standards, and stay focused on the bigger picture.
Conclusion
Your greatest wealth won’t be measured in dollars, but in the lives you shape, the values you pass on, and the legacy you leave.
Lead boldly — your future generations are counting on you.
As Justin puts it beautifully, “The things that matter most are the things that leave the biggest impact.” You have the power to create a legacy that lasts for generations, but it starts today, with intentional action.
If you want to dive deeper, listen to this powerful conversation with Justin Maxwell on the Wealth On Main Street podcast.
Share it with a fellow business owner, start asking bigger questions, and remember: wealth isn’t built by accident. It’s engineered on purpose.
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