How to Win BIG at Business With Accountants

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...

Send us Fan Mail In this episode of How to Win Big at Business , Joe talks with Marjorie “Marge” Aviso , co-owner of a successful BPO in the Philippines, about the real challenges behind entrepreneurial success.  Marge shares her journey from being a nurse and young mother to building a company with 1,600 employees , while navigating painful setbacks, financial mistakes, debt, and the hard decisio...

Send us Fan Mail AI is not replacing self-employed professionals — it is creating one of the greatest opportunities in business history. In this episode, Joe DiChiara explains why fear around AI is misplaced and how professionals who embrace new technology consistently come out ahead. Using real examples from the introduction of personal computers and QuickBooks, Joe shows how every major technolo...

Send us Fan Mail Most self-employed professionals start their business because they are great at what they do. But running a business requires more than expertise. It requires structure. In this episode of How to Win Big at Business, CPA and entrepreneur Joe DiChiara explains one of the biggest mistakes solopreneurs make: relying on large, unpredictable sales instead of building recurring revenue....

Send us Fan Mail In this episode of How to Win Big at Business , Joe DiChiara, CPA, tackles one of the most expensive mistakes self-employed professionals make: choosing the wrong legal and tax structure. Many entrepreneurs default into sole proprietorship or LLC status without understanding the long-term tax consequences. Joe explains: • Why 15.3% self-employment tax hits sole proprietors • Why L...

Send us Fan Mail In this episode of How to Win Big at Business , Joe DiChiara, CPA, tackles one of the biggest challenges self-employed professionals face: pricing. How do you avoid undercharging and burning out? How do you raise your prices without losing clients? How do you know what the market will bear? Drawing from over four decades advising entrepreneurs, Joe shares a powerful early-career s...

Send us Fan Mail If you keep attracting price shoppers, problem clients, or people who don’t value your work, this episode is for you. In this episode of How to Win Big at Business , Joe DiChiara, CPA explains why most self-employed professionals don’t have a client problem—they have a positioning problem. Joe breaks down: Why being “too general” kills client quality How selling services instead o...

Send us Fan Mail Uneven revenue is one of the biggest stress points for business owners — and almost nobody talks about it honestly. In this episode of How to Win Big at Business, Joe DiChiara, CPA and lifelong entrepreneur, tackles the reality of feast-or-famine income and explains how business owners can take control of their cash flow instead of being controlled by it. Drawing from his own acco...

Send us Fan Mail In this episode of How to Win Big at Business, Joe welcomes Larry Broughton for a candid, no-BS conversation about what it truly takes to succeed as an entrepreneur. In January 2001, Larry Broughton founded Orange County, California-based broughtonHOTELS , a leader in the boutique hotel industry. During what proved to be the worst two-and-a-half year period in the hospitality indu...

Send us Fan Mail In Episode 9, Joe DiChiara gets practical and tactical about one of the biggest stress points for self-employed professionals: tax anxiety. Joe explains that most tax-related stress is self-inflicted, not because people are careless, but because they don’t have systems. Drawing from his experience as a CPA and lifelong entrepreneur, he walks listeners through a step-by-step method...

Send us Fan Mail In Episode, Joe DiChiara tackles the growing anxiety self-employed professionals feel every January when tax season begins. Joe explains that tax stress doesn’t come from taxes themselves—it comes from lack of structure, poor bookkeeping habits, and not understanding your numbers. He walks listeners through the foundational steps every business owner must take to eliminate surpris...

Send us Fan Mail In this episode, I tackle one of the most frustrating realities of self-employment: 👉 You can be insanely busy and still not making real money. I break down why so many self-employed professionals stay trapped in a cycle of overwork, stress, and inconsistent income—and it has nothing to do with effort or talent. We’ll talk about: Why “being busy” is not the same as building a bus...