Lawyering Up: How to Secure Financial Stability in an Unpredictable Field w/Jess Bailey
Release Date: 03/06/2025
Doctors Make Great Money Until They Don’t (The Passive Income Fix) w/ Dr. Jeff Anzalone
Money School Podcast
From the outside, doctors and dentists look like they’ve got it all: good money, respected careers, the kind of lifestyle most people want. But what almost no one talks about is how fragile that life really is. One accident, one injury, and the very hands that their entire career depends on can suddenly stop producing income. That was Dr. Jeff Anzalone’s reality after a skiing accident nearly ended his ability to practice dentistry. It forced him to realize: as much as medicine can be rewarding, it’s still trading time for money, and it can all disappear in an instant. The solution...
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4,000 Reviews, $1M in Refunds: The Ugly Truth About IULs w/ Jonathan Aguilera
Money School Podcast
Most people who buy life insurance never read the fine print. They’re promised “stock market–like returns without the risk,” a retirement account that doubles as a tax-free loan machine, and peace of mind for their families. On paper? It looks like the perfect product. But what happens when the math doesn’t add up, the illustrations don’t match reality, and families find out, years later, that the policy they’ve been funding is set to collapse? That’s the dark underbelly of the Indexed Universal Life (IUL) industry. And it’s exactly what my guest, Jonathan, aka the IUL...
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4,000 Reviews, $1M in Refunds: The Ugly Truth About IULs w/ Jonathan Aguilera
Money School Podcast
Most people who buy life insurance never read the fine print. They’re promised “stock market–like returns without the risk,” a retirement account that doubles as a tax-free loan machine, and peace of mind for their families. On paper? It looks like the perfect product. But what happens when the math doesn’t add up, the illustrations don’t match reality, and families find out, years later, that the policy they’ve been funding is set to collapse? That’s the dark underbelly of the Indexed Universal Life (IUL) industry. And it’s exactly what my guest, Jonathan, aka the IUL...
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Don’t Wait: How to Line Up Business Financing Before You Need It w/ George Otel
Money School Podcast
Most business owners only call the bank when they’re in trouble. Cash is tight, deals are falling apart, stress is mounting. By then? It’s too late. The banks shut the doors and wave at you from behind the glass. That’s the obvious mistake. The less obvious one? Not realizing the best time to secure financing is when you don’t need it. That’s when banks give you more, on better terms, and when private lenders are willing to play ball. That’s the theme of my conversation with George Otel, founder of U.S. Business Funding. He’s closed 400+ deals, from SBA loans to $50M...
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Beyond the Bidding Wars: How Elite Investors Find Opportunities Others Miss w/ Aleea Stanton
Money School Podcast
Most real estate investors are running the same race: chasing the hottest markets, competing for the same deals, and trying to outbid one another. The problem? That crowded approach often blinds you to the opportunities hiding in plain sight. The truth is, success in investing isn’t about following the crowd or chasing trends; it’s about looking where others aren’t, leading with strategy, and building relationships that open doors no one else can see. That’s what sets Aleea Stanton apart. She didn’t start investing just to rack up properties. She began with a deeper purpose: to give...
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Lonely at the Top: The Quiet Crisis of the Ultra-Successful w/ David Christensen
Money School Podcast
You’ve experienced life at the highest level: private planes, exclusive circles, red carpet events, and the luxury that money can buy. But beyond the accolades and access, have you ever found yourself asking, 'Is this all there is?' There’s a silent struggle that often shadows success. Behind the velvet ropes and curated lifestyles, many high-profile individuals wrestle with an inner void—an ache that no amount of wealth, recognition, or adrenaline can truly silence. When the applause quiets and the entourage leaves, the stillness can feel suffocating. For some, that emptiness is numbed...
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Your Home’s Value Is Up, But Your Bank Account Isn’t? Try This w/ Arthur Hood
Money School Podcast
You’ve got something valuable sitting right under your nose: your home’s equity. But here’s the thing: it’s not exactly helping you pay the bills. Your house might be worth a lot more than before, but day-to-day expenses still pile up. Inflation’s squeezing your paycheck, groceries keep getting more expensive, and it feels like you’re stretched thinner every month. You’re “house rich,” sure, but cash? Not so much. And that’s exhausting. The reality is, owning a valuable home doesn’t mean your wallet feels any heavier. Lots of folks are stuck in this same spot right...
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What No One Tells You About Leaving Your Own Company w/Cody Hofhine
Money School Podcast
You built your business from scratch and poured your heart and soul into it. So it might feel strange, even disloyal, to think about stepping away or exiting. From the outside, everything’s working: sales are up, your team’s solid, and your brand is gaining traction. But under the surface? You’re tired, the vision that once felt clear now feels fuzzy, and growth has started to feel like a grind. This isn’t uncommon. Many founders hesitate to plan an exit because things still feel “fine.” But there’s a big difference between “fine” and truly free. Founders leave their...
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How to Beat the Insurance Companies at Their Own Game w/ Rob Haynie
Money School Podcast
Here’s the dirty secret in the term insurance industry: They win when you cancel. They win when your policy lapses. They win when you don’t understand what you really own. Think about that for a second. You’ve been sold on the idea that term insurance is the smart, affordable choice. But what no one tells you is this: it’s a ticking clock. If you outlive the term, you get nothing. All those years of paying in? Gone. Just like that. Who wins? The insurance companies. Every. Single. Time. They count on you to drop it. They bank on you not knowing any better. But what if you flipped the...
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Why So Many Real Estate Investors Are Burnt Out w/ Ashley Kehr
Money School Podcast
Feeling burnt out? You’re not the only investor hitting that wall. Long hours, back-to-back deals, tenants, contractors, financing, and the never-ending pressure to grow. You got into real estate for time freedom and financial independence, but somewhere along the way, it started to feel like just another grind. Here’s the truth most investors won’t say out loud: Burnout isn’t a rite of passage, it’s a red flag. And ignoring it can cost you more than just momentum; it can eat away at your health, relationships, and your reason for investing in the first place. But what if there’s...
info_outlineAttorneys face a unique set of challenges that go beyond courtroom battles and client meetings. From managing unpredictable income and student debt to tracking the financial health of their practice, the journey is often more financially demanding than most realize.
Many attorneys find themselves unprepared for the financial complexities of running a firm or navigating their career path, making it essential to have the right strategies in place early on.
That’s where Jess Bailey’s journey comes in. Jess, a lawyer who’s battled through the financial ups and downs of the legal world, knows exactly what it takes to safeguard yourself—both legally and financially. Through her experiences, she’s learned that the best way to stay ahead is to "lawyer yourself up" before trouble arises.
How would you navigate the financial complexities of your own legal journey? Have you ever felt unprepared when facing legal matters? What’s your next move to ensure you’re protected legally?
In this episode, Managing Attorney of the Bailey Law Firm Jess Bailey joins me to talk about the crazy journey attorneys go through, why it's so important to “lawyer up” as well as the financial aspect of law.
Things You’ll Learn In This Episode
-Raising money privately
Privately raising money requires building trust, networking with investors, and presenting a compelling opportunity. What strategies can you use to establish trust with potential investors when raising money privately?
-The importance of KPIs
Tracking your business’s KPIs helps measure success and identify areas for improvement. How can tracking the right KPIs reveal hidden strengths or weaknesses in your business?
-The true financials
Having resources on hand doesn't guarantee financial stability. How can we ensure that available resources are backed by actual financial strength in our business?
Guest Bio
Jess is the Managing Attorney of the Bailey Law Firm. Jess focuses her practice on business and real estate transactional law, as well as finance-specific compliance and transactional deals. Her representation has covered transactions in a variety of projects, from straightforward mergers and acquisitions to complicated deals riddled with compliance and regulatory matters. Having previously worked in real estate, mortgage and property management, banking, finance, and environmental consulting, Jess developed extensive experience with a diversity of contracts and negotiations, most of which businesses encounter daily. This experience also provided her with greater insight into the many operational issues that companies face every day. Jess has built a reputation for being an informative, knowledgeable, charismatic, and passionate counsel. She understands the real-world challenges and pragmatic decisions facing numerous industries. Irrespective of the project Jess works on, she considers all positive and negative factors that may affect the deal and the client’s business.
Visit https://baileylawfirm.com/
Find Jess on LinkedIn @Jess Bailey
About Your Host
From pro-snowboarder to money mogul, Chris Naugle has dedicated his life to being America’s #1 Money Mentor. With a core belief that success is built not by the resources you have, but by how resourceful you can be. Chris has built and owned 19 companies, with his businesses being featured in Forbes, ABC, House Hunters, and his very own HGTV pilot in 2018. He is currently founder of The Money School™, and Money Mentor for The Money Multiplier.
His success also includes managing tens of millions of dollars in assets in the financial services and advisory industry and in real estate transactions. As an innovator and visionary in wealth-building and real estate, he empowers entrepreneurs, business owners, and real estate investors with the knowledge of how money works.
Chris is also a nationally recognized speaker, author, and podcast host. He has spoken to and taught over ten thousand Americans delivering the financial knowledge that fuels lasting freedom.
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