Stacks Over Tax

Why do men and women often see the exact same business situation and walk away with completely different conclusions? Why do some partnerships thrive while others slowly break down through frustration, misunderstanding, and unmet expectations? And why do many entrepreneurs spend years trying to solve communication problems that aren't really communication problems at all? In this episode of St...

What if one of the biggest leadership advantages in business has nothing to do with strategy, sales, or operations? What if it comes from understanding the different strengths masculine and feminine energy bring to a team? In this episode of Stacks Over Tax, Mark Lewis, EA explores leadership, workplace dynamics, entrepreneurship, and the lessons CEOs can learn from understanding masculine and fem...

Why do so many smart, capable people struggle to communicate effectively with each other at work? Why do feedback conversations go sideways? Why do good intentions often create conflict instead of cooperation? In this episode of Stacks Over Tax, Mark Lewis, EA explores the differences between men and women in business through the lens of relationship expert Alison Armstrong's work, focusing on...

Why do so many smart, capable people struggle to communicate effectively with each other at work? Why do feedback conversations go sideways? Why do good intentions often create conflict instead of cooperation? In this episode of Stacks Over Tax, Mark Lewis, EA explores the differences between men and women in business through the lens of relationship expert Alison Armstrong's work, focusing on...

Many day traders hear the same advice over and over: "Just set up an LLC and you'll save a ton on taxes." Unfortunately, that's one of the most misunderstood concepts in the trading world. An LLC by itself typically doesn't change how your trading profits are taxed. In many cases, traders spend time and money creating entities that provide little or no direct tax benefit whil...

For years, economists, real estate experts, and policymakers have been asking the same question: Why aren't Baby Boomers selling their homes? The answer has far less to do with stubbornness, downsizing, or housing preferences than most people realize. In this episode of Stacks Over Tax, Mark Lewis, EA breaks down the economic forces keeping millions of homeowners locked into their current prop...

Most people hear the words "high interest rates" and immediately think bad news. Higher payments. More expensive loans. Less affordability. But many wealthy investors and business owners see something completely different. Opportunity. In this episode of Stacks Over Tax, Mark Lewis, EA sits down with Sterling Grace to explore one of the biggest mindset shifts in wealth building: understa...

For decades, Americans have been told that the 401(k) is the cornerstone of retirement planning. Work hard. Contribute every paycheck. Get the company match. Wait until retirement. But what if there are important parts of the story that most people never hear? In this episode of Stacks Over Tax, Mark Lewis, EA breaks down what a 401(k) actually is, how it works, the tax advantages, the hidden limi...

Most people spend their entire lives following financial advice that was designed to make them safe employees... not wealthy owners. Work hard. Save money. Avoid debt. Pay off your house. Max out your retirement account. Hope everything works out. The problem? That's not how most wealthy people build wealth. In this episode of Stacks Over Tax, Mark Lewis, EA breaks down the financial system, c...

Can you really make 30% annual returns trading? The answer may surprise you. Because the real question isn't whether 30% returns are possible. The real question is whether you can achieve those returns consistently, repeatedly, and with a process that doesn't rely on luck, prediction, or gambling. In this episode of Stacks Over Tax, Mark Lewis, EA breaks down the Executive Options Desk 22...

Few things create more panic than opening your mailbox and finding a letter from the IRS. But in many cases, the letter itself isn't the biggest problem. The real damage often comes from how taxpayers respond - waiting too long, saying the wrong thing, ignoring deadlines, volunteering unnecessary information, or making emotional decisions before they understand what the IRS is actually asking....

Most business owners have heard they’re supposed to pay quarterly taxes. Very few actually understand when they should. And even fewer understand when it can be financially smarter to keep that money working for themselves and effectively take a temporary loan from the IRS instead. In this episode of Stacks Over Tax, Mark Lewis, EA breaks down estimated taxes, quarterly tax payments, IRS underpaym...

Winning the lottery sounds like the ultimate financial dream. But what most people never realize is that the moment you win, you're immediately faced with one of the biggest tax and wealth-building decisions of your entire life: should you take the lump sum or the annuity? In this episode of Stacks Over Tax, Mark Lewis, EA breaks down the tax consequences of lottery winnings, the differences b...

The IRS is entering a new era - and if you're still operating under old assumptions about audits, enforcement, and compliance, you may be far more exposed than you realize. At a recent IRS symposium, agency officials discussed how artificial intelligence is being integrated into enforcement efforts, data analysis, return matching, and compliance initiatives. One of the clearest messages? The I...

Most people think filing a tax extension gives them extra time to pay their taxes. It doesn't. And for many taxpayers and business owners, filing in October instead of April quietly costs them thousands of dollars in lost opportunities, delayed planning, reduced cash flow, and one of the most expensive financial mistakes of all: giving the IRS an interest-free loan through an oversized refund....

Trusts may be one of the most misunderstood topics in all of finance, estate planning, and asset protection. Between internet gurus, social media "experts," sales-driven trust promoters, and even professionals who repeat outdated information, it can be incredibly difficult to separate real law from marketing hype. In this episode of Stacks Over Tax, Mark Lewis, EA breaks down the truth a...

Most taxpayers are leaving thousands of dollars on the table every year because they either don't understand itemized deductions... or worse, they're following bad advice from internet "tax gurus" pushing deductions that don't actually survive IRS scrutiny. In this episode of Stacks Over Tax, Mark Lewis, EA breaks down how itemized deductions really work, when they outperform...

Building generational wealth isn’t just about making money - it’s about creating a long-term financial strategy built on responsibility, discipline, intelligent investing, and understanding how money actually behaves over decades. In this episode of Stacks Over Tax, Mark Lewis, EA sits down with investing expert David Stein to discuss financial strategy, investing psychology, wealth preservation,...

Everyone wants success. Very few people are prepared for what success actually costs. In this episode of Stacks Over Tax, Mark Lewis, EA sits down with Stefanos Sifandos for a deep conversation about entrepreneurship, masculinity, relationships, emotional mastery, business pressure, personal growth, and the hidden psychological price many high performers silently pay while building wealth and succ...

AI is coming faster than most people understand - and the people who simply sit still, rely on outdated skills, and refuse to adapt are going to be replaced economically faster than they ever imagined. In this episode of Stacks Over Tax, Mark Lewis, EA sits down with Ana White of Ana White DIY to discuss artificial intelligence, entrepreneurship, self-reliance, woodworking, creative business build...

Most entrepreneurs think the biggest problem with taxes is simply paying too much. But the real problem is what happens AFTER the tax bill - because most business owners have absolutely no system for turning retained business capital into long-term wealth. In this episode of Stacks Over Tax, Mark Lewis, EA sits down with the founders of Melanin Money to expose the dirty secret about your tax bill...

Success in business isn’t just about sales, money, or strategy. According to MLM leader and entrepreneur Tom Challan, the greatest business tool for long-term success is something most entrepreneurs completely overlook: love. In this episode of Stacks Over Tax, Mark Lewis, EA sits down with Tom Challan to discuss leadership, entrepreneurship, network marketing, relationships, personal growth, and...

Most business owners are either completely missing legitimate vehicle tax deductions… or they’re deducting auto mileage in ways that dramatically increase their IRS audit risk. In this episode of Stacks Over Tax, Mark Lewis, EA breaks down the truth about deducting auto mileage, how the IRS actually views vehicle deductions, and the biggest mistakes entrepreneurs make when trying to write off thei...

Want to know how an HSA can be your secret weapon for tax-free savings and smart investing? In this episode of Stacks Over Tax, Mark and Sterling make HSAs easy to understand and show you how to really make the most of them.- The real differences between HSAs and FSAs, and why HSAs are way more flexible- Who can open an HSA and how much you can actually put in for 2025- All the ways your HSA money...

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