What It Really Takes to Succeed: Entrepreneurship, Adversity, and Smarter Financial Thinking
We often talk about investing, taxes, and retirement plans but sometimes, the most important part of financial success has nothing to do with spreadsheets. It has to do with mindset. On this episode of The Truth About Money, I sat down with Brandon Corso, Sheila Johnson, and Dan Gasby to explore what really drives success through recession, adversity, racism, irrational thinking, and failure.
Let’s start with a lesson in boldness.
Sheila Johnson’s Playbook for Recession-Proof Growth
During the 2008–2009 recession, while most people were tightening their belts, Sheila Johnson did the opposite. She acquired hotels, golf resorts, and developed a luxury property in Northern Virginia with 168 rooms and a 23,000-square-foot spa. She turned a struggling golf resort in Tampa into a success by leaning on the dedication of its long-time employees and she didn’t stop there. Sheila partnered with Lubert-Adler to expand her hospitality holdings across Orlando, Palm Coast, and even the Dominican Republic.
Her secret? She didn’t wait for the storm to pass she learned how to dance in the rain.
Sheila’s story is a masterclass in spotting opportunity when others see only risk. That’s something she shares with the likes of Warren Buffett, who famously buys when others are fearful. Sheila proves that optimism, action, and a long-term view can lead to real success even in tough times.
Think Like an Investor, Not Just a Consumer
One of the big takeaways from Sheila’s story is simple: You can’t wait for perfect conditions. Whether you’re running a business or managing your personal finances, opportunities rarely show up with a red carpet. You have to be willing to move forward when everyone else is standing still.
We see this in investing all the time. The best returns come to those who are willing to buy when prices are low, even if fear is high.
Traditional vs. Roth 401(k)? It Depends on Your Tax Bracket
We also took a great question from John, who wanted to know whether to invest in a traditional 401(k) or a Roth. John makes $50,000 a year and gets a 6% match from his employer. My recommendation? Go traditional.
Here’s why: John is in the 25% tax bracket, so every dollar he puts into a traditional 401(k) comes with an immediate tax break. That’s free money. Roth accounts are better suited for people in the 10–15% bracket, where the tax savings just aren’t as significant. For higher earners, traditional makes more sense now while you’re in a high tax bracket and expect to be in a lower one later in retirement.
Why I’m a Fan of Long Mortgages
Let me say something controversial: I don’t think you should rush to pay off your mortgage.
Wait, what?
That’s right. Even if you have the cash to pay off your house, keeping a long mortgage gives you options. You can invest the cash instead and potentially grow your wealth, rather than locking it up in an illiquid asset.
Besides, do you ever really own your house? You still have to pay property taxes, insurance, maintenance it’s not like your expenses vanish the day your mortgage is gone. That’s why I encourage people to keep their mortgage and use that extra cash to build real financial flexibility.
The key, of course, is discipline. Don’t blow the extra cash. Invest it. Let it work for you.
The Real Reason We Make Dumb Money Decisions
Let’s talk about the elephant in the room: behavioral economics.
Traditional economists used to believe that humans are perfectly rational when it comes to money. I call B.S. We are wildly irrational. We chase gains, fear losses, and make completely different choices depending on how questions are framed even when the math is identical.
This is why behavioral economics has become such a critical part of financial planning. Nobel Prize-winning research has proven that psychology drives our money decisions far more than logic. That’s why working with a financial advisor isn’t just about math it’s about helping you not sabotage yourself.
Racism in Business: Turning No Into Yes
B. Smith and her husband, Dan Gasby, opened up about the racism they encountered in their entrepreneurial journey how people judged B. by how she looked or spoke, rather than by the strength of her ideas.
What struck me most was their determination. They didn’t just accept “no” they used it as fuel. Dan pointed out that when you’re a person of color in business, you often have to work twice as hard to be seen as credible. But he also reminded us that money talks. When you can show how your idea can make money, suddenly, skin color becomes less of a barrier.
It’s a sobering reality and a powerful reminder to lead with results and resilience.
Redefining Failure as a Stepping Stone
B. Smith and Dan Gasby also hit on something every entrepreneur needs to hear: you will fail. And that’s okay.
Failure isn’t the end. It’s tuition for success. They talked about rejection as part of the path and how entrepreneurs fail more because they try more. If you’re afraid to fail, you’ll never innovate, never stretch, never grow.
It’s true in business. It’s true in investing. And it’s true in life.
Clients, Expectations, and the Reality Check
Finally, we heard from financial advisors at a conference who shared the wild assumptions some clients make like thinking they can beat the market, retire early with minimal savings, or skip out on professional help. Spoiler: They can’t.
Success requires planning, patience, and persistence. It’s not magic it’s math. And getting advice from professionals isn’t a weakness it’s a smart move.
Bottom line?
Whether you’re launching a business, managing your money, or facing discrimination success starts with your mindset. Stay optimistic. Take action. Learn from failure. Invest in your future. And don’t let irrational fears stop you from building real wealth.
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