How to Win BIG at Business With Accountants

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 actu...

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,...

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...

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 T...

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—...

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...

Send us Fan Mail That IRS notice isn't junk mail — and being afraid to open it can turn a manageable problem into a much bigger one. For many taxpayers and business owners, just seeing an envelope from the IRS is enough to cause panic. But an IRS notice does not automatically mean you're in serious trouble . Some notices are informational. Some request additional information. Others invo...

Send us Fan Mail Owe the IRS money? The worst thing you can do is ignore it. Whether your tax debt is $5,000, $50,000, $100,000 or more, fear and embarrassment can cause you to freeze. But ignoring IRS notices, unfiled returns, unpaid balances, liens, or potential levies can allow a manageable tax problem to turn into a much bigger one. In this episode of How to Win BIG at Business , CPA and entre...

Send us Fan Mail In this episode of How to Win Big at Business, Joe DiChiara explains one of the most dangerous mistakes small business owners make: running the business by looking at the bank balance. Joe breaks down why cash flow is not simply “what’s left over” after paying bills. Cash flow should be a system — one that tells you where the money is going, what needs to be set aside, what belong...

Send us Fan Mail Do you ever finish a long workday completely exhausted… but still wonder what you actually accomplished? You’re not alone. For many self-employed professionals and small business owners, the real problem isn’t a lack of time. It’s a lack of focus. When you're answering emails, taking client calls, checking your phone, working on proposals, managing employees, thinking about m...

Send us Fan Mail A practical guide for self-employed professionals who want an accountant who helps them understand the numbers, plan ahead, protect their information, and make better business decisions.  Do you have an accountant? Is your accountant a good accountant? Most importantly, how would you know? There is a major difference between an accountant who simply prepares your tax return and on...

Send us Fan Mail Small business owners are tired, frustrated, and confused by the never-ending stream of tax rules, compliance issues, payroll requirements, sales tax laws, IRS notices, state regulations, and all the things they “don’t know they don’t know.” That is exactly why Joe DiChiara is refocusing the podcast. In this episode of How to Win Big at Business with Accountants, Joe explains why...

Send us Fan Mail In this episode of How to Win Big at Business, Joe DiChiara explains one of the most dangerous mistakes small business owners make: running the business by looking at the bank balance. Joe breaks down why cash flow is not simply “what’s left over” after paying bills. Cash flow should be a system — one that tells you where the money is going, what needs to be set aside, what belong...

Send us Fan Mail What happens when an AI tool stops acting like a tool — and starts making decisions for you? In this episode of How to Win Big at Business, Joe DiChiara shares a personal experience with Claude AI that started as a simple project: tracking calories, exercise, weight loss, and daily progress. Joe was using AI the way many self-employed professionals are beginning to use it — as a h...

Send us Fan Mail Tax compliance may feel painful, annoying, and overwhelming — but it is not optional. In this episode of How to Win Big at Business, Joe DiChiara speaks directly to self-employed professionals and small business owners who are frustrated by the growing burden of invoices, receipts, payroll records, sales tax rules, tax filings, and government compliance. Joe opens with the voice o...

Send us Fan Mail What if planning your business could feel like planning the best trip of your life? In this episode of How to Win Big at Business , Joe DiChiara invites self-employed professionals, solopreneurs, and small business owners to imagine building a business with the same excitement, clarity, and possibility as planning a dream vacation. But instead of flights, hotels, and destinations,...

Send us Fan Mail The IRS may be quiet right now, but Joe DiChiara warns business owners not to get too comfortable. In this episode of How to Win Big at Business , Joe explains why the next wave of IRS audits may look very different from the old days. Instead of face-to-face meetings with an agent, business owners may be asked to electronically or digitally provide bank statements, invoices, recei...

Send us Fan Mail If AI has you overwhelmed, this episode will help you stop spinning, focus on what matters, and start using it in a way that actually helps your business. You are not alone. In this episode of How to Win Big at Business, Joe DiChiara breaks down AI in a way that actually makes sense for self-employed professionals. No hype. No jargon. No fear-mongering. Just a practical conversati...

Send us Fan Mail If you’re a self-employed professional still doing everything yourself, this episode is for you. For years, business owners have said, “You just can’t find good help anymore.” But in this episode of How to Win Big at Business , Joe DiChiara challenges that belief and sits down with Nick Petras of HireFreely to talk about what’s really changing in the world of hiring, freelancing,...

Send us Fan Mail Success on the outside does not always mean peace on the inside. In this episode of How to Win Big at Business, Joe sits down with therapist and self-employed professional Tara Larchemar for a powerful conversation about what many entrepreneurs quietly struggle with: anxiety, burnout, emotional overwhelm, relationship stress, and the pressure of trying to hold everything together...

Send us Fan Mail What do you do when life changes in an instant? In this powerful episode of How to Win Big at Business , Joe DiChiara sits down with Vincent Lanci — author, podcaster, coach, entrepreneur, and traumatic brain injury survivor — to talk about recovery, resilience, purpose, and rebuilding a life after everything changes. Vincent shares the story of being hit by a car at age 21, wakin...

Send us Fan Mail Most business owners think they know their numbers — but if you’re only watching sales and your bank balance, you could be making decisions based on the wrong information. They are either tracking nothing or tracking the wrong things . In this episode of How to Win Big at Business , Joe DiChiara CPA breaks down the key numbers every self-employed professional and small business ow...

Send us Fan Mail What if the biggest financial mistake small business owners are making is relying on numbers that are already too old to help them?  In this episode of How to Win Big at Business , Joe breaks down why the role of the CFO is becoming more important than ever for self-employed professionals and small business owners. Business owners do not just want historical financial statements a...

Send us Fan Mail In this episode of How to Win Big at Business, Joe DiChiara sits down with entrepreneur and technology expert Jerry Goddard to talk about a problem almost every self-employed professional is facing right now: AI overwhelm. If you feel buried by too many AI tools, too many subscriptions, and too much hype, this conversation will help you cut through the noise. Joe and Jerry break d...

Send us Fan Mail In this episode of How to Win Big at Business , Joe talks with Marianne “Coach Yanyan” Labonete about the real path from corporate work to entrepreneurship, freelancing, coaching, and business freedom. Marianne shares how she navigated career changes, income pressure during the pandemic, online work, bookkeeping, client acquisition, and eventually built a powerful personal brand a...