How to Win BIG at Business

Joe DiChiara
  • 0.0 (0)
  • ENTREPRENEURSHIP

Being a solopreneur or small business owner isn’t easy—you’re wearing all the hats, managing clients, handling finances, and trying to grow without burning out. That’s where this podcast comes in. Hosted by Joe DiChiara, CPA, entrepreneur, and business mentor, How to Win BIG at Business delivers straight talk, practical strategies, and real stories that help you cut through the noise and focus on what really moves the needle. Each week, we dive into topics like: Smarter tax and money strategies 💰Using AI and automation to save time ⚡Marketing that actually works (without overwhelm) 📣Building passive income streams 💡Protecting your business and scaling the right way 🚀Whether you’re a freelancer just starting out, a solopreneur ready to grow, or a seasoned small business owner looking for fresh ideas, this podcast gives you the clarity, confidence, and tools to win at business—and at life. 👉 Subscribe now and join a community of entrepreneurs who are rewriting the rules of success.

Episodes

  1. 5D AGO · BONUS

    Guest Episode #1 — Featuring Vincent A. Lanci Expert Podcaster & Podcast Producer

    Send us a text 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 podcasting business. Joe and Vincent dive into:  • The real emotional and financial challenges of entrepreneurship  • How trauma shaped Vincent’s resilience and mission  • The birth of That Entrepreneur Show and A Mental Health Break  • Using networking, resourcefulness, and mentorship to build a business  • The moment Vincent realized he could monetize his skills  • How he overcame a devastating summer downturn, failed payments, and client losses  • Why adversity is often the catalyst for growth  • Practical advice for new and aspiring entrepreneurs Listeners will walk away with powerful insights on mindset, perseverance, and building a business with purpose. Connect with the Guest:  Website: VincentALanci.com  Email: info@VincentALanci.com  Podcasts: That Entrepreneur Show, A Mental Health Break, Pod O’Clock 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 Gaurd 365) www.Bedrock360BusinessTraining.com (Courses)

    34 min

  2. 12/31/2025

    Episode 5 — Start Small, Start Smart: The Micro-Course Formula for New Entrepreneurs

    Send us a text 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, and increased authority. He breaks down the essentials of building your first course, the equipment you actually need, and the platforms best suited for beginners and growing creators. Listeners will learn:  • Why your first course should be small, focused, and fast to produce  • How authenticity beats perfection in online education  • How to choose the right platform (Zoom, Loom, Thinkific, Go High Level, Kajabi, Teachable)  • Why short 3–5 minute lessons outperform long presentations  • How to test and refine your course from a student’s perspective  • How micro-courses can evolve into full course series and long-term digital assets Joe also offers podcast listeners a complimentary 20-minute strategy call to help map out their business or course creation plan. www.timewithjoe.com This episode is ideal for new entrepreneurs, overwhelmed business owners, and anyone ready to monetize their expertise through simple, scalable digital products. 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 Gaurd 365) www.Bedrock360BusinessTraining.com (Courses)

    17 min

  3. 12/26/2025

    Monetize Your Genius Through Course Creation

    Send us a text 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 common, how he overcame perfectionism, and how AI transformed the entire course-creation process. If you want new revenue streams, more credibility, or a simple way to launch a business, this episode gives you the roadmap. 👉 Free strategy call for listeners at timewithjoe.com 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 Gaurd 365) www.Bedrock360BusinessTraining.com (Courses)

    17 min

  4. 12/16/2025

    The Secret to Staying Motivated: Why Winners Eat Discipline for Breakfast

    Send us a text 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 and discipline? They’ll carry you when your “why” is still asleep. With his signature blend of wisdom, humor, and Brooklyn-born bluntness, Joe unpacks: 🔥 Why even successful entrepreneurs occasionally fantasize about getting a “normal job”  🔥 How habits become your secret weapon when motivation packs its bags  🔥 Joe’s own daily routine — including his massage gun, stretching, and the occasional strategic nap  🔥 How Benjamin Franklin’s “Moral Perfection Project” can keep modern entrepreneurs grounded  🔥 The 17 success principles of Napoleon Hill… and how Joe adapted them into his own 13 guiding rules  🔥 Why taking a nap might be the most productive thing you do all day  🔥 How faith, focus, and a little bit of humor can pull you through the roughest seasons in business You’ll walk away with practical tools, a deeper sense of clarity, and maybe the comforting realization that every entrepreneur feels like quitting sometimes — the winners are just the ones who keep getting up. If you’ve ever had a “Why did I start this business?!” moment… this episode is your permission slip to breathe, reset, and get back on track. New episodes every week. Subscribe now and learn how to win big — one habit at a time. 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 Gaurd 365) www.Bedrock360BusinessTraining.com (Courses)

    24 min

  5. 12/09/2025

    When Your Business Actually Starts (And Why It Matters More Than You Think)

    Send us a text 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 Staples, or simply launching an idea that “defies logic.” Because let’s be honest: Real entrepreneurs ARE delusional. And that’s exactly why they create, innovate, and challenge the world — even if most of their ideas should probably stay on the cutting-room floor. In this episode, Joe tackles essential topics every entrepreneur must understand: The two requirements that officially start your businessWhy your car, computer, phone, and even a portion of your home become legitimate tax write-offsThe hidden danger of commingling funds (and how it sinks entrepreneurs)The truth about audits in the AI eraWhy bootstrappers put themselves at risk by avoiding accountantsThe myth of “I’ll hire a CPA when I’m making money”Why most QuickBooks DIYers end up with a financial train wreckThe real cost of flying solo — and the peace of mind of having a pro on your sideJoe also shares stories from the trenches — including IRS war stories, audit nightmares, and business owners unknowingly throwing away thousands of dollars in deductions because nobody ever told them the rules. If you’re serious about building a business — not a hobby — this episode is a must-listen.  And if you’ve ever wondered whether your Thanksgiving dinner could be a business write-off… yeah, Joe covers that too. Subscribe for weekly episodes that help you avoid the pain, protect your profits, and win big at business — one smart decision at a time. 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 Gaurd 365) www.Bedrock360BusinessTraining.com (Courses)

    26 min

  6. 12/02/2025

    Welcome to How to Win Big at Business: The Real Truth About Entrepreneurship

    Send us a text 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-powered business coach, and creator of the Business-in-a-Box system — this podcast blends old-school wisdom with modern tools to help everyday business owners win bigger, faster, and smarter. In this maiden episode, Joe shares: Why entrepreneurship isn’t for the faint of heartHis journey from running a casino in his driveway at age 10 to advising thousands of business ownersThe real highs, lows, setbacks, and breakthroughs that shape a businessThe surprising mistakes that derail most new entrepreneurs — and how to avoid themHow to build a business you love without burning out, going broke, or getting blindsidedWhy mindset, systems, and preparation matter more than talentHow clarity and confidence beat hustle and chaos every timeJoe’s style is part educator, part coach, part Brooklyn-born truth-teller. You’ll get insights you can use immediately — delivered with humor, encouragement, and a no-nonsense focus on helping you build a business that supports your life (instead of swallowing it whole). This podcast is for you if you want to learn: How to start and scale a business the right wayHow to handle taxes, money, and complianceHow to stay out of trouble with the IRSHow to use AI tools to save time and grow revenueHow to create simple systems that eliminate chaosHow to avoid the biggest mistakes new business owners makeHow to develop the mindset and resilience to win big in business and in lifeWhether you’re just getting started, rebuilding after a setback, or ready to level up, Joe is here to inform, prepare, and empower you every step of the way. New episodes drop weekly. Subscribe now and start winning big — in business and in life. 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 Gaurd 365) www.Bedrock360BusinessTraining.com (Courses)

    45 min
  • 6 Episodes

About

Being a solopreneur or small business owner isn’t easy—you’re wearing all the hats, managing clients, handling finances, and trying to grow without burning out. That’s where this podcast comes in. Hosted by Joe DiChiara, CPA, entrepreneur, and business mentor, How to Win BIG at Business delivers straight talk, practical strategies, and real stories that help you cut through the noise and focus on what really moves the needle. Each week, we dive into topics like: Smarter tax and money strategies 💰Using AI and automation to save time ⚡Marketing that actually works (without overwhelm) 📣Building passive income streams 💡Protecting your business and scaling the right way 🚀Whether you’re a freelancer just starting out, a solopreneur ready to grow, or a seasoned small business owner looking for fresh ideas, this podcast gives you the clarity, confidence, and tools to win at business—and at life. 👉 Subscribe now and join a community of entrepreneurs who are rewriting the rules of success.

Information

  • Creator
    Joe DiChiara
  • Years Active
    2025 - 2026
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © 2026 How to Win BIG at Business
  • Show Website
    How to Win BIG at Business