Small Business Tax Savings Podcast

👉 Interested in learning more about oil and gas investing?  Email us at ask@taxsavingspodcast.com and we’ll connect you with Nick White and the team at US Energy. Big tax deduction or risky investment? Oil and gas investing can be a powerful tax strategy for high-income business owners, but it’s not something to jump into just because you want a write-off. In this episode, Mike sits down with Nic...

Free money for kids? Not so fast. Trump Accounts could become one of the newest long-term wealth-building tools for families, but you need to understand how they work, who qualifies, and how they fit into a bigger tax and investment strategy. In this episode, Mike breaks down everything you need to know about the Trump Accounts. He covers the contribution rules, tax-deferred growth, employer contr...

Don’t wait until the last minute to start tax planning. Mid-year is one of the best times for business owners to review their tax situation. Most business owners wait until year-end to ask, “How can I lower my tax bill?” But by then, some of the best opportunities are already gone. Instead of making proactive tax-saving moves, you’re left doing damage control. In this episode, Mike walks through a...

Stop treating your retirement like a someday problem…For business owners, the right plan can be a valuable tax strategy. But too many entrepreneurs wait too long, choose the wrong plan, or assume a 401(k) is only for big companies.  In this episode, Mike sits down with Matt Ruttenberg to explain how retirement plans work for small business owners. They break down the differences between SEP IRAs,...

Small tax mistakes can cost you thousands, even when you think you’re doing everything right. From missing a filing deadline to misunderstanding how a deduction works, small errors can quickly turn into penalties, lost deductions, and a higher tax bill. In this episode, Mike answers real tax questions from small business owners covering gambling losses, BOI reporting, moving an S corporation to an...

Your CPA isn’t saving you money… And it’s probably not their fault.  Many business owners expect their CPA to handle everything: bookkeeping, tax filing, tax strategy, and financial guidance.  In this episode, Mike breaks down the four financial roles every business owner needs to understand: bookkeeper, tax preparer, tax strategist, and CFO or advisor. He explains what each role does, what they d...

Your bookkeeping changes everything from a tax standpoint. If your books are messy, outdated, or based on guesswork, your tax planning is already working with bad information. You may miss deductions, misjudge your profit, make poor year-end decisions, or overpay the IRS without realizing it. In this episode, Mike breaks down why bookkeeping is not just administrative work. It is the foundation of...

Hiring one remote employee in another state changes everything from a tax standpoint. The same goes for selling products or services across state lines. Once your business creates a connection to another state, that state may expect you to register, file, collect taxes, or handle payroll compliance there. In this episode, Mike sits down with Nellie Akalp, CEO and Co-Founder of CorpNet, to break do...

You spend money on meals and travel all the time; Client lunches, flights, hotels, conferences, team dinners, and networking events are all part of running a business. But most business owners don’t know what is actually deductible anymore. In this episode, Mike breaks down the 2026 rules for meals, travel, and entertainment deductions. He explains what still qualifies, what changed, what is no lo...

Should you open another LLC, elect S Corp status, or create a more advanced business structure? Mike breaks down when a multi-entity structure makes sense, and when it creates more confusion than value.  Learn when one LLC is enough, how S Corps and partnerships fit in, and why timing matters. Structure too early and you create chaos. Wait too long and you expose yourself to risk.  👉 Get the Free...

Are you still afraid to deduct certain business expenses because you think the IRS might come after you for it? Meals. Travel. Home office. Vehicle expenses. Software. Education. Coaching. Even paying your kids. These deductions can feel risky when the lines between personal and business spending are not clear. In this episode, Mike breaks down the business expenses many owners skip out of fear, a...

Most business owners treat filing their taxes like the finish line. It isn’t.  What actually lowers your tax bill is what you do before December, and that starts with knowing how to read the return you just filed. In this episode, Mike walks through a six-step process for reviewing your 2025 tax return the right way. You will learn what numbers actually matter on your 1040, how to tell if the stra...

Every business owner hits a point where the tax questions start stacking up.  Can I deduct this? Should I switch to an S Corp? Is this still a business if I have not made money yet? And what happens if I did something before I had my systems set up the right way? In this episode, Mike opens the floor to questions from business owners and breaks down the tax answers behind them. From zero-activity...

Every year, the IRS updates important tax numbers, that most business owners miss. This leads to missed deductions, poorly timed income decisions, and unnecessary overpayments to the IRS. In this episode, we break down the most important 2026 tax updates business owners need to know, including changes to tax brackets, standard deductions, Social Security wage caps, retirement limits, HSA contribut...

Estimated taxes should not feel like a guessing game, but for many business owners, they do. Underpay, and you face stress, penalties, and a big bill in April. Overpay, and you hand the IRS more cash than needed, limiting what you can reinvest in your business. In this episode, we break down how estimated taxes actually work, why the U.S. tax system is pay-as-you-earn, and how to avoid both overpa...

Are you worried a tax strategy could land you in trouble with the IRS?  In this episode, Mike Jesowshek sits down with tax attorney Ed Lyon to break down what tax risk actually means. They explain why most business owners do not get in trouble for smart tax planning, where the line between gray-area strategy and fraud really sits, and why proper implementation matters just as much as the strategy...

You’ve hired your first employee… Now what?  Hiring your first employee introduces a new layer of tax responsibility, compliance, and systems that many business owners are not prepared for. You are now managing payroll taxes, filings, labor laws, and deadlines that carry real penalties if handled incorrectly. In this episode, we break down exactly what happens after you hire your first employee so...

Filing a tax extension feels stressful for many business owners. Missing numbers, unfinished bookkeeping, and uncertainty about the tax bill can make tax season overwhelming. But filing an extension (in many cases) can be the smartest move you can make. A tax extension gives you more time to file your return so you can organize your records, receive missing documents like K-1s, and avoid rushing t...

Charitable giving rules are changing in 2026, and many business owners have no idea their tax deductions could quietly shrink. The One Big Beautiful Bill Act introduced new limits, floors, and deduction caps that change how charitable donations work depending on your income level and whether you itemize deductions. In some cases, you could donate the exact same amount and receive a smaller tax ben...

Imagine breaking even at the casino and still owing taxes. Beginning in 2026, Congress approved a new rule that limits gambling loss deductions to 90%. That means if you win $10,000 and lose $10,000, you could still owe taxes on $1,000 of phantom income. Today, we're breaking down the new gambling tax rule that quietly slipped into law, why it creates phantom income for gamblers, and what cas...

Can you deduct free food, rent your house to your business or avoid double taxation with a C Corp? In this Q&A episode, Mike answers rapid-fire tax questions submitted by business owners across industries. From restaurant deductions to partnership restructuring, foreign contractors, co-mingled expenses, and advanced C Corp investing strategies, this episode walks through what’s legal, what’s s...

If you're already giving to charity, you're leaving thousands of dollars in tax deductions on the table.  What is a donor-advised fund and why should you care? Mike sits down with Adam Nash, CEO of Daffy, to break down how Donor-Advised Funds (DAFs) work and why they can be a powerful tax strategy for business owners and high-income earners.  If you regularly give to your church, your ki...

When should you pay yourself? Paying yourself on the wrong payroll schedule can create IRS red flags, cash flow crunches, and painful cleanup later. In this episode, we break down monthly, quarterly, and annual payroll for S Corp owners. You’ll learn what the IRS actually expects, how reasonable salary works, why quarterly “true-ups” can create cash flow problems, and how to structure payroll to s...

Paying yourself wrong can trigger IRS issues, messy books, and unexpected tax bills.  In this episode, we break down exactly how LLC owners should pay themselves in 2026 based on their entity type and tax election. You’ll learn the 3 primary ways business owners get paid: owner draws or distributions, payroll, and guaranteed payments. We explain which payment methods are legally allowed for single...

You formed your LLC. Good job. But many business owners unknowingly make critical mistakes after formation that quietly destroy liability protection, trigger audits, and limit growth. In this episode, Mike walks through the 10 most common LLC mistakes business owners make in 2026 and explains exactly how to fix them. From mixing personal and business finances to ignoring tax planning and misclassi...