How to Win BIG at Business and Taxes

Joe DiChiara
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  • Entrepreneurship

How to Win Big at Business and Taxes is the podcast for self-employed professionals, entrepreneurs, and small business owners who want to make more money, keep more of what they earn, pay less in taxes legally, and build a business that works for them—not the other way around. Hosted by Joe DiChiara, CPA and entrepreneur, each episode delivers practical, straight-talking strategies for navigating both sides of entrepreneurship: building a better business and making smarter tax decisions. We tackle the issues that can make or break a small business—from profitability, cash flow, pricing, systems, marketing, and growth to tax planning, IRS problems, tax debt, compliance, deductions, entity structure, and avoiding expensive tax mistakes. You'll learn how to: Build a more profitable and sustainable businessUnderstand the numbers that actually drive your successImprove cash flow and make smarter financial decisionsReduce your tax burden through proactive tax planningAvoid costly tax and compliance mistakesUnderstand IRS notices, tax debt, liens, levies, and collection optionsUse systems, technology, and AI to operate more efficientlyMove from overwhelmed solopreneur to confident business owner You'll also hear from entrepreneurs and professionals who share the lessons, mistakes, strategies, and experiences that helped them build successful businesses. Because winning big isn't just about how much your business makes. It's about how much you keep, how well you protect it, and the freedom your business creates. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, tax strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone. Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage)www.Bedrock360TaxSolutions.com (Tax Guard 365)www.Bedrock360BusinessCourses.com (Courses)

  1. 1d ago ·  Video

    Can You Get IRS Penalties Removed? Here's What the IRS Doesn't Tell You

    Send us Fan Mail "If you got an IRS notice saying you owe $25,000, would you assume you have to pay all of it? Most people would. But what if thousands of dollars of that balance were penalties and interest that could potentially be removed?" The IRS says you owe $25,000. But do you really have to pay every dollar? When you receive an IRS notice, the first thing you probably see is the balance due. What you may not realize is that the amount can include three very different things: unpaid taxes, IRS penalties, and interest. And under the right circumstances, some of those penalties—and the interest associated with them—may qualify for relief. In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA, explains how IRS penalty relief works, why you should never blindly accept an IRS balance, and what you can do to challenge penalties that may not be justified. You'll discover: Why an IRS balance isn't necessarily the final amount you must pay.The difference between unpaid taxes, penalties, and interest.Common IRS penalties, including late filing, late payment, payroll tax deposits, and information returns.What qualifies for reasonable-cause penalty relief.How medical emergencies, natural disasters, and missing records can affect your case.When problems involving your tax professional may support a penalty-relief request.How to review IRS transcripts and identify potential errors.How to write an effective IRS penalty-abatement request.When IRS Form 843 may be appropriate.What to do when the IRS denies your request.How the IRS's 2026 Automatic Exemption from Penalty program may help eligible taxpayers.Joe also shares real experiences from his CPA practice, including cases involving incorrectly processed tax returns, unexpected penalties, and successful penalty challenges. The big takeaway: Don't assume every dollar on an IRS notice is correct or unavoidable. Investigate the balance, understand your options, and take action before the problem becomes more expensive. Want Joe's IRS penalty-relief letter templates? Email joe@bedrock360taxsolutions.com and request the IRS Penalty Relief Templates. If you're dealing with an IRS notice, penalties, or an outstanding tax balance, schedule a conversation at www.timewithjoe.com. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

  2. Oct 13 ·  Video

    Can’t Afford to Pay the IRS? How Currently Not Collectible Status Works

    Send us Fan Mail What happens when you owe the IRS—but you genuinely cannot afford to pay them anything? Sometimes the right monthly payment isn't $5,000. It isn't $500. It isn't even $200. Sometimes, temporarily, it may be $0. In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA explains Currently Not Collectible (CNC) status—an IRS collection status designed for taxpayers experiencing financial hardship. Joe breaks down what CNC actually means, how financial hardship is evaluated, why documentation matters, how the IRS looks at allowable living expenses, and why simply telling the IRS, “I can't afford to pay,” isn't enough. You'll learn: • What Currently Not Collectible status means • How CNC can temporarily stop IRS collection activity • What the IRS considers financial hardship • Why allowable living expenses matter • Why your actual expenses and IRS-allowed expenses may be very different • How income, family size, assets, medical circumstances, and other factors can affect your case • Why having money or significant assets can change the analysis • What happens if your financial situation improves • Why CNC does NOT eliminate your tax debt • Why tax liens can remain in place • Why interest and penalties can continue accumulating • Special considerations for business owners • Why tax problem resolution is about choosing the right strategy—not simply finding the lowest monthly payment Joe also explains why taxpayers should be careful when choosing someone to handle an IRS problem. Being a CPA, EA, attorney, or working for a large tax-resolution company does not automatically mean someone has extensive tax-resolution experience. Ask questions. Understand the process. And make sure the person representing you has a strategy for resolving the underlying problem—not simply providing temporary relief. If you're dealing with an IRS problem and want to discuss your situation, Joe is offering podcast listeners a free consultation. Visit www.timewithjoe.com and indicate that you heard Joe on the podcast. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

  3. Oct 6 ·  Video

    Can You Really Settle IRS Debt for Pennies on the Dollar?

    Send us Fan Mail The Truth About IRS Offers in Compromise You've seen the advertisements: “We settled $100,000 in IRS debt for $2,000!” Can that really happen? Yes. But there's a lot those advertisements aren't telling you. In this episode of How to Win BIG at Business, Joe DiChiara, CPA takes you behind the scenes of the IRS Offer in Compromise program and explains how the IRS actually determines whether someone may qualify to settle a tax debt for less than the full amount owed. An Offer in Compromise isn't simply a negotiation where you throw out a number and wait for the IRS to counter. The IRS looks at your financial situation, including your income, allowable living expenses, assets, equity and potential ability to pay. Joe walks through examples showing why two taxpayers who owe exactly the same amount of money can have completely different outcomes. You'll learn about: What an Offer in Compromise actually isWhy owing a large amount doesn't automatically mean you qualifyHow income and allowable expenses affect the calculationWhy home equity and other assets matterHow the IRS evaluates your potential collectibilityFinancial disclosure requirementsForms 656 and 433Documentation you may need to provideWhat happens to collection activity while an offer is being consideredWhat happens if the IRS rejects your offerAppeal rightsWhy Joe doesn't recommend an OIC unless he believes the facts support itWhen an installment agreement or another resolution may make more senseMost importantly, Joe explains why Offer in Compromise isn't automatically the best option just because it sounds attractive. ep43 If you're dealing with IRS debt, don't start with the television commercial. Start with the numbers. Free Resource Download Joe's Offer in Compromise Qualification Checklist to help determine whether an OIC may be worth investigating. Need Help With an IRS Problem? Visit www.timewithjoe.com to schedule a consultation. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

  4. Sep 29 ·  Video

    IRS Payment Plans: Easy to Get, Expensive to Get Wrong

    Send us Fan Mail Getting an IRS payment plan can be surprisingly easy. Getting the RIGHT payment plan is another story. In Episode 8 of Joe DiChiara CPA's 12-part Tax Problem Resolution Series, Joe breaks down IRS installment agreements and explains why simply asking the IRS for a monthly payment arrangement may not be the smartest way to resolve your tax problem. Before agreeing to anything, you need to answer a more important question: Do you actually owe what the IRS says you owe—and is an installment agreement really your best option? Joe explains why taxpayers should verify their balance before making a deal, especially when unfiled returns, IRS-filed substitute returns, penalties, or processing errors may be involved. You'll learn about: • IRS Simple Payment Plans • Short-term payment arrangements • Why penalties and interest can continue while you're paying • Why staying current with future taxes is critical • What happens when you miss an installment payment • Why business tax debt can be more complicated than individual debt • The special danger of unpaid payroll and trust-fund taxes • Why cash-flow problems need to be fixed before the tax problem can truly be fixed • When an Offer in Compromise or another resolution strategy may make more sense • How the IRS collection statute can affect your strategy Joe also shares his own experience receiving repeated IRS collection notices—including a notice of intent to levy—because an amended payroll tax return had not been processed. The lesson? Never assume an IRS notice is correct, never ignore it, and don't choose a resolution strategy simply because it's the easiest one to obtain. A payment plan should be part of a larger financial strategy—not just a way to make the latest IRS notice disappear. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

    IRS Payment Plans: Easy to Get, Expensive to Get Wrong

  5. Sep 22 ·  Video

    You Say $500. The IRS Says $2,500: How the IRS Decides What You Can Pay

    Send us Fan Mail You may think you can only afford to pay the IRS $500 a month. The IRS may look at the exact same financial situation and decide you can afford $2,500. Why? Because when the IRS determines your ability to pay, it doesn't simply look at how much money is left in your checking account at the end of the month. In Episode 6 of our Tax Problem Resolution Series, CPA Joe DiChiara breaks down how the IRS evaluates your financial situation when you're trying to establish an installment agreement or resolve a tax debt. Joe explains how the IRS examines: • Your income and current cash flow • Business revenue and legitimate business expenses • IRS allowable living expenses • Housing and transportation costs • Bank accounts and available cash • Investments and other assets • Real estate and available equity • Credit and borrowing ability • Special financial circumstances • Your previous compliance history • The documentation supporting your numbers You'll also learn about the Collection Information Statements used in tax resolution, including Forms 433-A, 433-B, and 433-F, and why accurately completing these forms can make an enormous difference in the outcome of your case. Joe walks through a simple example: A taxpayer earns $12,000 per month and spends $11,500. The taxpayer says: “I only have $500 left. That's all I can afford.” But what happens when $2,000 of that person's housing expense exceeds what the IRS considers allowable? Suddenly, the IRS may calculate the taxpayer's ability to pay very differently. That's why being cash-flow poor doesn't necessarily mean you're IRS poor. Joe also explains why hiding assets, understating income, inflating expenses, or submitting incomplete financial information can turn a difficult tax problem into an even bigger one. Before negotiating with the IRS, you need to understand the financial picture the way the IRS will see it — not simply the way you see it. If you're considering an installment agreement, Offer in Compromise, or another IRS collection alternative, this episode will help you understand what may happen before you ever submit the paperwork. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

    You Say $500. The IRS Says $2,500: How the IRS Decides What You Can Pay

  6. Sep 15 ·  Video

    IRS Liens & Levies: What to Do Before the IRS Takes Your Money

    Send us Fan Mail Owe the IRS money? Ignoring the problem can eventually turn IRS notices into something much more serious: liens, bank levies, wage garnishments, and even attempts to collect money directly from people who owe your business money. But a tax lien and a tax levy are not the same thing—and understanding the difference could give you valuable time to act. In Episode 5 of our 12-part Tax Problem Resolution Series, Joe DiChiara, CPA, explains what happens when an IRS collection case begins moving from letters and notices toward enforced collection. Joe breaks down: • What a Federal Tax Lien actually means • The difference between an IRS lien and an IRS levy • How a Notice of Federal Tax Lien can affect mortgages, loans, property sales, and other financial transactions • What the IRS may potentially levy • How bank levies work • Why the 21-day bank levy holding period can be extremely important • Why wage levies are different from bank levies • How the IRS can potentially reach accounts receivable • Why self-employed professionals and business owners need to pay special attention • What happens when customers receive notices directing payments away from you • Final Notice of Intent to Levy letters • Collection Due Process hearings • The importance of the 30-day appeal window • Installment agreements, Offers in Compromise, and Currently Not Collectible status • Economic hardship situations • Why releasing a levy does not necessarily remove a federal tax lien • Five common myths about IRS liens and levies • What Joe would immediately investigate if a client called and said, “The IRS just levied my bank account.” One of the most important lessons in this episode is simple: Not having enough money to pay the IRS does not mean you should avoid filing your tax returns or ignore IRS notices. There may still be options available—but deadlines matter. Joe also explains why a bank levy is generally very different from a wage levy. A bank levy can represent a snapshot of funds available when the levy reaches the bank, while a wage levy can continue from paycheck to paycheck. And for business owners, there's another major danger many people overlook: accounts receivable. Your money doesn't necessarily have to be sitting in your bank account for IRS collection activity to disrupt your business. FREE RESOURCE If you've received an IRS levy or Final Notice, request Joe's: IRS Levy Emergency Kit Email: joe@bedrock360taxSolutions.com and request the IRS Levy Emergency Kit. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

  7. Sep 8 ·  Video

    Caught in the IRS Collection Machine? Here’s What Happens Next

    Send us Fan Mail Getting a bill from the IRS can be scary—but owing money doesn’t mean the IRS suddenly shows up and takes your bank account. There is a collection process, and understanding how that process works can give you valuable time to take action. In Episode 38 of How to Win BIG at Business, Joe DiChiara, CPA breaks down what actually happens after the IRS determines that you owe taxes—and why ignoring IRS notices is one of the worst things you can do. Joe explains:  The difference between filing a tax return and an IRS assessment How an unpaid balance begins moving through the collection process  Why IRS notices become increasingly serious  What the IRS Automated Collection System (ACS) is  The difference between an IRS tax lien and an IRS levy What a Notice of Intent to Levy means  Why checking your IRS.gov account can be important  Why voluntarily making payments may help reduce accumulating penalties and interest  How Currently Not Collectible status may help taxpayers experiencing financial hardship  Your potential collection appeal rights  How the IRS collection statute generally works  Why every tax year and assessment can have its own collection timeline Most importantly, Joe explains a principle every taxpayer with an IRS problem needs to understand: Ignoring the problem doesn't make it disappear. It usually allows the problem to escalate. If you owe the IRS—or know someone who does—this episode will help you better understand the collection process and the importance of dealing with the situation before it becomes more serious. Educational purposes only. Individual tax situations vary, and taxpayers should seek professional advice regarding their specific circumstances. Get The Free Bedrock360 IRS Emergency Levy Kit by requesting it via email at www.joe@bedrock360businesssolutions.com Mention the kit in the subject line If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

  8. Sep 1 ·  Video

    Haven’t Filed Taxes in Years? Here’s How to Fix It

    Send us Fan Mail Haven’t filed a tax return in three years? Five years? Maybe even ten? Ignoring the problem might feel easier today—but it can make the situation far more difficult tomorrow. In this episode of How to Win BIG at Business, Joe DiChiara, CPA and entrepreneur, explains why unfiled tax returns are often the beginning of much larger IRS problems and, more importantly, what you can do to start fixing them. For self-employed professionals and small business owners, falling behind can happen surprisingly easily. A financial setback, business failure, missing records, personal hardship, confusion over complicated tax rules—or simple procrastination—can turn one missed return into several years of unfiled taxes. Joe walks you through how to begin digging out. In this episode, you’ll learn:  Why taxpayers fall behind on filing their returns  Why waiting until you have the money to pay isn't necessarily the right strategy  Why filing a return doesn't always mean the IRS has processed it  How an IRS online account can help you determine which returns are actually on file  How IRS transcripts can help reconstruct missing tax information  What a Wage and Income Transcript can tell you  How business owners may be able to reconstruct records using bank and credit card statements  What happens when records are missing  Why filing compliance is critical before resolving an IRS balance  What an IRS Substitute for Return (SFR) is  Why an IRS-prepared return may create a much larger tax bill  How installment agreements, Currently Not Collectible status and Offers in Compromise can fit into a tax resolution strategy  Why communication and cooperation with the IRS matter  How to protect yourself from questionable tax resolution companies  Real-world examples of taxpayers who faced serious IRS problems—and found a path forward Joe also shares the story of a business owner who fell eight years behind, encountered payroll tax problems, paid thousands of dollars to people who failed to solve the problem, and ultimately had to reconstruct years of financial records. He also discusses a taxpayer with approximately $25,000 in IRS debt whose circumstances ultimately led to an Offer in Compromise settling the case for approximately $500. The big lesson? The IRS isn't going anywhere. If you have unfiled returns or unresolved tax debt, the answer isn't to keep hiding from the problem. Find out exactly where you stand, get into compliance, understand your options and start working toward a resolution. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone.  Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage) www.Bedrock360TaxSolutions.com (Tax Guard 365)  www.Bedrock360BusinessCourses.com (Courses)

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About

How to Win Big at Business and Taxes is the podcast for self-employed professionals, entrepreneurs, and small business owners who want to make more money, keep more of what they earn, pay less in taxes legally, and build a business that works for them—not the other way around. Hosted by Joe DiChiara, CPA and entrepreneur, each episode delivers practical, straight-talking strategies for navigating both sides of entrepreneurship: building a better business and making smarter tax decisions. We tackle the issues that can make or break a small business—from profitability, cash flow, pricing, systems, marketing, and growth to tax planning, IRS problems, tax debt, compliance, deductions, entity structure, and avoiding expensive tax mistakes. You'll learn how to: Build a more profitable and sustainable businessUnderstand the numbers that actually drive your successImprove cash flow and make smarter financial decisionsReduce your tax burden through proactive tax planningAvoid costly tax and compliance mistakesUnderstand IRS notices, tax debt, liens, levies, and collection optionsUse systems, technology, and AI to operate more efficientlyMove from overwhelmed solopreneur to confident business owner You'll also hear from entrepreneurs and professionals who share the lessons, mistakes, strategies, and experiences that helped them build successful businesses. Because winning big isn't just about how much your business makes. It's about how much you keep, how well you protect it, and the freedom your business creates. If you’re a self-employed professional trying to build a real business, this podcast was created for you. New episodes break down the systems, strategies, tax strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featured Thanks for listening! If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk. Book a strategy call: www.timewithjoe.com Because running a business shouldn’t feel like wrestling an octopus… alone. Also check out: www.Bedrock360BusinessSolutions.com (Complete Coverage)www.Bedrock360TaxSolutions.com (Tax Guard 365)www.Bedrock360BusinessCourses.com (Courses)

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