How to Win BIG at Business

Joe DiChiara
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  • 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.

  1. 4d ago

    You Don’t Have a Time Problem — You Have a Focus Problem

    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 marketing, and trying to grow your business at the same time, your attention is constantly being pulled in different directions. And when everything becomes a priority, nothing is really a priority. In this episode of How to Win BIG at Business, Joe DiChiara breaks down practical ways to regain control of your time, attention, and business. You’ll discover: The three questions that can bring immediate clarity to your businessWhy constantly switching between tasks destroys productive focusHow “attention residue” follows you from one task to anotherWhy your phone can distract you even when it never ringsHow to stop treating every email like an emergencyHow communication windows create better boundaries with clientsHow to use time blocking to control your dayWhy every day should have one clearly defined #1 priorityHow the “3 D’s” can dramatically reduce your task listWhy delegation and automation become critical as your business growsHow to create a 90-day focus goal for your businessJoe also shares the lesson he learned after years of being a workaholic: Your business should support your life. Your life shouldn’t exist to support your business. One of the biggest differences between struggling entrepreneurs and successful business owners is the ability to decide what matters most—and then stay focused on it long enough to produce a result. Try the 90-Day Focus Exercise from this episode: Choose one important business result you want to accomplish over the next 90 days. Identify the weekly activities that will produce that result. Eliminate or reduce activities that compete with it. Then put the focused work on your calendar. Stop trying to become a better taskmaster. Become a focus master. 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.Bedrock360BusinessTraining.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 Gaurd 365)  www.Bedrock360BusinessTraining.com (Courses)

  2. Aug 4

    Is Your Accountant Helping You Win—or Just Filing Your Taxes?

    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 one who actively helps you build a stronger, more profitable business. In this episode of How to Win BIG at Business, Joe DiChiara explains why every self-employed professional needs more than a once-a-year tax preparer. Your accountant should help you understand your financial reports, anticipate problems, minimise taxes legally, protect your sensitive information, and make better decisions throughout the year. Joe also shares the questions you should ask before hiring an accountant—and the questions you should continue asking after the relationship begins. In this episode, you’ll learn: The difference between an accountant and a tax preparerWhy responsiveness is one of the most important qualities to evaluateWhat to ask about bookkeeping software and monthly reconciliationsWhether your accountant should provide reports and financial analysisHow to determine who is actually handling your accounting workWhat to ask about privacy, cybersecurity, and access to your informationWhat happens to your records and accounting software if you leaveWhy tax planning must take place before the end of the yearThe three qualities Joe believes every excellent accountant should haveA good accountant doesn’t merely tell you what happened. A good accountant helps you understand why it happened—and what you should do next. Listen now, share this episode with another business owner, and subscribe to How to Win BIG at Business for practical strategies on taxes, money, business growth, and entrepreneurship. Learn more or schedule a conversation with Joe 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)

  3. Jul 11

    Why Small Business Owners Need Accountants More Than Ever

    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 small business owners need better access to practical, real-world guidance from accountants, tax preparers, enrolled agents, CPAs, attorneys, insurance professionals, and other small business experts. Joe shares the story of his first real business: leasing an ice cream truck before his final semester of college. He made money, kept records, signed legal documents, saved receipts, and thought he was doing everything right — until he received a frightening tax warrant letter from the New York State sales tax department. At 22 years old, working in his first accounting job, Joe thought he might need a tax attorney or lose his job. The real issue? He had registered as a sales tax vendor and did not know he had to file quarterly sales tax reports, even though no tax was due. That experience taught him a lesson every business owner eventually learns: Business is not as simple as it looks. Joe explains why the podcast is evolving into a platform that brings in accountants and other experts to help small business owners understand the issues that can create unnecessary pain, penalties, overpaid taxes, missed opportunities, and sleepless nights. This episode covers why business owners need to understand sales tax, nexus, payroll, independent contractors, foreign worker forms, IRS audits, state tax departments, departments of labor, technology-driven enforcement, and the growing risk of AI-assisted audits. The message is clear: small business owners need guidance, support, and education before the problem arrives. 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.Bedrock360BusinessTraining.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 Gaurd 365)  www.Bedrock360BusinessTraining.com (Courses)

  4. Jun 23

    When AI Says No: A Wake-Up Call for Business Owners

    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 helper, organizer, calculator, and productivity tool. But then something unexpected happened. After days of tracking meals, exercise, calorie intake, and weight loss goals, the AI program decided it would no longer continue calculating Joe’s daily calorie deficit. Instead of simply producing the numbers requested, it stepped back, expressed concern, and recommended a different direction. That moment raised a much bigger question: What happens when the technology we pay for decides what it will and will not do for us? Joe connects this experience to a much larger issue facing self-employed professionals and business owners: AI is powerful, useful, and here to stay — but it also comes with risks. If you are using AI to run your business, create content, organize client data, produce documents, analyze numbers, or manage operations, you need to think carefully about what you are sharing, where that data is going, and how much trust you are placing in these tools. This episode is not anti-AI. Joe uses AI every day and believes it can be a major advantage for entrepreneurs. But he also believes business owners need to stay alert, protect sensitive information, and remember that AI should support human judgment — not replace it. In this episode, Joe discusses: Why he started using Claude AIHow AI helped him track health, calories, exercise, and weight lossThe surprising moment the AI refused to continue the calculationWhy AI guardrails can create unexpected business concernsWhy self-employed professionals must be careful with personal and business dataThe danger of relying too heavily on tools we do not fully controlWhat this experience means for entrepreneurs, consultants, accountants, coaches, and freelancersWhy AI is powerful — but still needs human oversightIf you are self-employed and using AI in your business, this episode is an important reminder: AI can help you move faster, but you still need to protect your judgment, your data, and your business. 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.Bedrock360BusinessTraining.com (Courses) This episode includes a personal story involving calorie tracking and weight loss. Nothing in this episode should be taken as medical advice. Always consult a qualified health professional before making decisions about diet, exercise, or health. 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)

  5. Jun 17

    Tax Compliance Is Not Optional: Protect Your Business Before the IRS Comes Calling

    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 of the frustrated business owner: “Why do I have to spend all this time submitting information? What am I paying you for?” Then he explains the hard truth: when you start a business, you also accept the responsibility to keep records, substantiate deductions, follow payroll rules, understand sales tax exposure, and protect yourself before the IRS or state government comes knocking. Joe breaks down why tax compliance has become a major part of running any business, no matter how small. He discusses sales tax complexity, payroll documentation, independent contractor issues, economic nexus, e-commerce rules, state tax enforcement, and the growing possibility of more automated IRS audits. He also shares real audit stories involving a trucking business and a film project where taxpayers were forced to fax in piles of records — and where deductions were challenged because the government questioned whether they were business-related. The message is clear: business owners can no longer afford to play compliance roulette. If you are self-employed, you need organized electronic records, a clear naming convention, proper invoices, payroll documentation, sales tax awareness, and a system for capturing receipts before problems happen. Because when it comes to tax compliance, waiting can be expensive. 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.Bedrock360BusinessTraining.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 Gaurd 365)  www.Bedrock360BusinessTraining.com (Courses)

  6. Jun 9

    Build the Business of Your Life: A Wake-Up Call for Self-Employed Professionals

    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, Joe is talking about something far more important: the business that can create your freedom, income, purpose, and future. Joe shares why he created this podcast as a resource for self-employed professionals who are tired of struggling alone. He speaks directly to the business owner who is dealing with loneliness, pressure, self-doubt, sleepless nights, confusing decisions, tax problems, legal structure questions, cash flow stress, marketing challenges, and uncertainty about what to do next. As a CPA with over 40 years of experience and a lifelong entrepreneur, Joe explains how he helps business owners make things simpler, clearer, and more structured — from startup planning and tax minimization to cost reduction, CFO-level strategy, KPIs, marketing, scaling, and business systems. Joe also shares his own entrepreneurial origin story, starting with a driveway “casino” at age 10 that earned him a $3 profit and sparked a lifelong love of business. The lesson? Entrepreneurship is not easy. Failure happens. But failure does not make you a failure — it can be a temporary defeat on the road to something greater. This episode is both a personal invitation and a powerful reminder: you do not have to build your business alone. 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.Bedrock360BusinessTraining.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 Gaurd 365)  www.Bedrock360BusinessTraining.com (Courses)

  7. Jun 2

    The IRS Audit Wave Is Coming: Why Business Owners Must Fix Their Records Now

    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, receipts, and records — and if they cannot prove their deductions, the IRS may simply disallow them. Joe shares real audit stories from business owners who were hit with massive proposed tax assessments, including one trucking company that faced hundreds of thousands of dollars in potential IRS and state tax exposure. The key lesson? Even legitimate business expenses can be denied if the records are sloppy, missing, or poorly organized. This episode is a wake-up call for self-employed professionals, consultants, contractors, freelancers, and small business owners who have gotten too relaxed with bookkeeping and document storage. Joe explains why your receipts, invoices, bank statements, business journals, travel documentation, payroll records, and expense support are not optional — they are your defense if the IRS comes knocking. You’ll learn why now is the time to build a clean electronic filing system, create a smart naming convention, organize records by year, and stop treating recordkeeping like an afterthought. Because when the audit letter comes, it may already be too late to fix the mess. 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.Bedrock360BusinessTraining.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 Gaurd 365)  www.Bedrock360BusinessTraining.com (Courses)

  8. May 26

    Confused About AI? Start Here Before You Waste Time and Money

    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 conversation about what AI is, how to think about it, and how to start using it in your business without wasting time, energy, or money. Joe shares his perspective as a lifelong entrepreneur who has lived through multiple major technology shifts, from desktop computers to the internet to accounting software, and explains why AI is just the latest big transition. He also explains why the people who ignore it may eventually find themselves playing expensive catch-up. In this episode, Joe covers: why AI feels so overwhelming right nowhow this moment compares to other major technology shiftswhy AI is more than just a search toolthe power of prompts and why prompting is a real business skillhow persona, tone, context, audience, and output affect resultsthe differences between ChatGPT, Gemini, and Claudehow GPTs, Gems, Projects, and Artifacts can save massive amounts of timewhy AI should be used to improve your team, not replace your peoplehow business owners can use AI to compress time, improve output, and create new opportunitiesThis episode is especially valuable for self-employed professionals who know they need to understand AI but do not want to get buried in tech confusion or shiny-object syndrome. 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.Bedrock360BusinessTraining.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 Gaurd 365)  www.Bedrock360BusinessTraining.com (Courses)

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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
    33
  • Rating
    Explicit
  • Copyright
    © 2026 How to Win BIG at Business
  • Show Website
    How to Win BIG at Business