Small Business Tax Savings Podcast

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You could qualify for thousands of dollars in tax deductions, but without the right documentation, the IRS could take them away.

Mike sits down with Doug Breaker, owner of Shoeboxed, to explain how proper recordkeeping helps business owners protect their tax deductions. They break down what to document for receipts, meals, mileage, home offices, and business travel, how long to keep your records, and how...

Can a rental property put $30,000 in your pocket without adding $30,000 to your taxable income? Let’s talk about rental property tax strategies

Mike explains how rental real estate can create tax savings even when you can’t use rental losses to offset your business or W-2 income. 

He breaks down the difference between cash flow and taxable income, how depreciation can shelter rental income, and what happens to suspended passive losses. He also covers short-term rental rules, real estate professional status, common entity mistakes, and the key questions to ask before buying a rental property.

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👉 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 Nick White from US Energy to break down how oil and gas investing works, where the tax benefits come from, and why intangib...

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 contribution opportunities, Roth conversion planning, and how Trump Accounts compare to 529 plans, Roth IRAs, custodial accounts, and brokerage accounts. 

👉 Get the Free Tax Savings Starter Kit Built for Smal...

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 simple mid-year tax checkup every small business owner should do before December. He covers how to review your income, estimate your tax liability, clean up your bookkeep...

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, SIMPLE IRAs, solo 401(k)s, safe harbor 401(k)s, and defined benefit plans, plus the questions you should ask before choosing a plan, including your contribution goals, employee needs, cost, tim...

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 another state, the Augusta Rule, HSAs, late 1099s, estimated tax penalties, startup expenses, vehicle write-offs, and more. He breaks down the rules, explains the available options, and shares practical steps to help yo...

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 do not do, and how building the right financial team can help you stay compliant, make better decisions, and legally lower your tax bill.

👉 Get the Free Tax Sa...

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 smart tax planning. He explains what bookkeeping actually is, how your profit and loss statement and balance sheet affect your taxes, and why clean, accurate books help business owners make better decisions...

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 down state tax nexus in plain English. They explain what creates nexus, why remote employees and multi-state sales can trigger tax obligations, and what business owners need to do to avoid...

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 longer deductible, and how business owners can turn everyday spending into legitimate tax savings without creating unnecessary IRS risk.

👉 Get the Free Tax Savings Starter Kit Built for S...

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 Tax Savings Starter Kit Built for Small Business Owners:
https://www.taxsavingspodcast.com/starterkit

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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, and explains how to think about deductions the right way. You will learn what “ordinary and necessary” really means, why documentation matters more than fear, and why playing it too safe can...

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 strategies you implemented actually worked, where most business owners leave money on the table without realizing it, and how to build a real tax plan for...

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 LLC filings and Schedule C concerns to family payroll planning, vehicle deductions, and rental strategies like the Augusta Rule, this e...

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 contributions, mileage rates, capital gains thresholds, and Section 179 expensing. 

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:
https://www.taxsavingspodcast.com/starterkit

🚀 Book your free de...

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 overpaying and underpaying. We cover the safe harbor rules, why accurate bookkeeping matters, and how to build a smarter system for quarterly payments that...

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 itself. 

They cover audit risk, common red flags, what to ask before moving forward with an advanced strategy, and how business owners should think about th...

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 you can avoid costly mistakes and set your business up to scale the right way. We cover the difference between W2 employees and 1099 contractors, the real cost of payroll taxes, how to stay compl...

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 through a return that could contain mistakes. In this episode, we break down how extensions actually work, clear up common myths about audit risk, and explain what to do if you...

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 benefit than before.

Today we're breaking down the new charitable giving tax rules, who wins under the new system, who loses, and how smart business owners can still give generously while protecting...

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 casual and professional gamblers need to do right now to protect themselves.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:
https://www.taxsavingspodcast.com/starterkit

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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 smart, and what’s risky. If you want clarity before you file, this is the one to listen to.

👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:
https://w...

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 kids’ school, your alma mater, or other charities, this episode shows you how to give more strategically, reduce taxes, and increase your impact.

👉 Ready t...

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 stay compliant without overpaying in taxes.

We also cover catch-ups, slowdowns, bonuses, zero payroll returns, and a critical but often-missed strategy involving self-employed health insurance and HSA contri...

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-member LLCs, partnerships, and S corporations, and why running payroll as an owner is prohibited unless you have an S corporation election.

We walk through how each method is taxed, how it...

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 misclassifying owner compensation, this episode gives you a practical framework to audit your business and protect it the right way.

If you want your LLC to survive and thrive...

Thinking about forming an LLC in 2026? In this episode, Mike breaks down how to set up an LLC step by step, what “free” really means, state filing costs, common mistakes to avoid, and why an LLC can act as an insurance policy for future S Corp tax savings. Perfect for new and growing business owners who want clarity without the confusion.

If you want a clean, simple business setup that protects you now and gives you flexibility later, this episode gives you the roadmap without the legal confusion.

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If you are already behind on your taxes in January, there are four tax tasks you cannot skip.

In this episode, we break down the four financial tasks every business owner needs to complete in January to start 2026 clean and organized. Mike explains why unfinished bookkeeping leads to missed deductions and unnecessary stress, how to properly review your financials, and why most tax issues begin long before filing season.

We also cover the importance of creating a simple financial summary document, meeting the January 31 1099 deadline, and building a proactive tax plan early in the year...

Are you still guessing when it comes to 1099s? Most business owners are. And every January, that confusion turns into stress, penalties, and last-minute cleanup that could have been avoided.

In this episode, Mike Jesowshek breaks down everything small business owners need to know about 1099-NEC and 1099-MISC forms, who needs one, who doesn't, the deadlines and the penalties that add up fast. 

If you want January to feel calm instead of chaotic, this episode gives you the clear rules and simple process to get compliant without overthinking it.

 🧾 Good systems prevent tax h...

Happy Holidays, and thank you. This episode is a personal thank-you to the Small Business Tax Savings Podcast community. We reflect on nearly eight years of the show, including over 400 episodes and more than 1.5 million downloads.  At the core of this podcast is one mission; Helping small business owners pay the least amount in taxes legally, without stress or confusion. 

 Let’s make 2026 the year you get proactive about tax planning from the start. 

If this podcast has helped you in any way this year, there are a few small things you can do to help u...

Do you really have your tax planning handled? The thing is, many business owners are making a critical mistake that will become even more expensive by 2026.

In this episode, Mike Jesowshek, CPA, sits down with Mark J. Kohler to expose the biggest tax planning failure business owners make. Confusing knowing strategies with actually applying them. Mark explains why tax savings disappear at the implementation level, how poor execution creates long-term consequences, and why retirement accounts are one of the most overlooked areas where this mistake shows up.

👉 Get the Free Tax Savings Starter Kit Built for...

If you’re a new business owner, you've probably wondered if you are doing any of this correctly.

Should you get an LLC? Do you file a Schedule C? Can you hire your kids? Does a home office hurt you when you sell your house?

In this episode, Mike walks through real questions from listeners and gives clear answers to the tax issues that confuse most new entrepreneurs. From 1099 income and deductions to home office rules, the Augusta Rule, and hiring your kids, this Q&A hits the topics every early-stage owner struggles with.

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