How to Win BIG at Business and Taxes

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 business Understand the numbers that actually drive your success Improve cash flow and make

How to Win BIG at Business and Taxes is a business podcast hosted by Joe DiChiara, with 41 episodes on record and a Required Pod Score of 80.

Joe DiChiara hosts How to Win BIG at Business and Taxes, a business show with 41 episodes published.

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  Episode #42

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

  Oct 6, 202621 minS1

  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 is Why owing a large amount doesn't automatically mean you qualify How income and allowable expenses affect the calculation Why home equity and other assets matter How the IRS evaluates your potential collectibility Financial disclosure requirements Forms 656 and 433 Documentation you may need to provide What happens to collection activity while an offer is being considered What happens if the IRS rejects your offer Appeal rights Why Joe doesn't recommend an OIC unless he believes the facts support it When an installment agreement or another resolution may make more sense Most 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)

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  Episode #41

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

  Sep 29, 202626 minS1

  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! 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) 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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  Episode #40

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

  Sep 22, 202636 minS1

  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! 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.LearnUSTaxes.com (Courses) 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.Bedrock360BusinessTraining.com (Courses)

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  Episode #39

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

  Sep 15, 202625 minS1

  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! 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.LearnUSTaxes.com (Courses) 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.Bedrock360BusinessTraining.com (Courses)

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  Episode #38

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

  Sep 8, 202613 minS1

  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. 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! 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.LearnUSTaxes.com (Courses) 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.Bedrock360BusinessTraining.com (Courses)

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