How to Win BIG at Business With Accountants

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...

Send us Fan Mail In today’s episode, I break down what I believe are the five biggest mistakes self-employed professionals make—mistakes I’ve seen over and over again after working with thousands of business owners over the last 40+ years. And here’s the key thing to understand:  These mistakes are all connected. Fix one, and you often start fixing the others. We kick things off with Mistake #5—no...

Send us Fan Mail In this powerful guest episode, Joe DiChiara welcomes award-winning podcaster and author Vincent A. Lanci, whose remarkable story of survival and reinvention has inspired audiences around the world. After being struck by a car, placed in a coma, and told he might never walk or live independently again, Vincent rebuilt his life from the ground up—and eventually built a top-tier pod...

Send us Fan Mail In this episode of How to Win Big at Business , Joe DiChiara, CPA, explains why micro-courses are the most accessible and effective way for entrepreneurs to launch or expand a business—especially if you're short on time, experience, or technical skills. Joe discusses the emotional roller coaster of entrepreneurship and how micro-courses provide stability, new revenue streams,...

Send us Fan Mail In Episode 4 of How to Win Big at Business , Joe DiChiara, CPA, reveals why creating online courses is the fastest and easiest way to grow—or even start—a business. Whether you’re an expert, a hobbyist, or someone who thinks they “don’t know enough,” this episode shows how anyone can turn their knowledge into income. Joe shares how he taught accounting remotely long before it was...

Send us Fan Mail Running a business is tough — and some days, so is getting out of bed. In this episode of How to Win Big at Business, Joe DiChiara, CPA and lifelong entrepreneur, pulls back the curtain on one of the biggest struggles every business owner faces: staying motivated when life (and business) keeps throwing haymakers. Joe shares the simple truth: motivation is unreliable… but habits an...

Send us Fan Mail In this episode, Joe DiChiara, CPA and lifelong entrepreneur, cuts straight to one of the biggest mysteries in the small-business world: When does a business actually begin?  (Here’s a hint — it’s not when you make your first dollar.) Joe breaks down what really happens the moment you have a profit motive and take your first action — whether that’s buying a laptop, driving to Stap...

Send us Fan Mail Running a business shouldn’t feel like a constant guessing game — and on this podcast, it won’t. Welcome to How to Win Big at Business , the show where entrepreneurs, solopreneurs, and consultants come to get the clarity, confidence, and straight-talk strategies they need to grow without the overwhelm. Hosted by Joe DiChiara, CPA — a 40-year entrepreneur, bestselling author, AI-po...