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.

  1. 2d ago

    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)

    11 min

  2. 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)

    12 min

  3. 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)

    29 min

  4. May 19

    Still Doing Everything Yourself? This May Be Why You’re Stuck

    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, remote work, and AI. Together, they unpack one of the biggest growth obstacles for self-employed professionals: getting past the solopreneur stage and making that first real hire. They discuss why traditional hiring is often slow, frustrating, and broken… and why the future may belong to business owners who think differently about skills, delegation, flexibility, and remote talent. This conversation is especially relevant for consultants, accountants, coaches, agency owners, and other self-employed professionals who know they need help but are overwhelmed by the process of finding the right person. In this episode, you’ll learn:  Why most small businesses never make it past the solopreneur stage  Why the first hire is such a major business milestone  Why “you can’t find good help anymore” is no longer true  What COVID and remote work changed forever  Why resume-based hiring is becoming less effective  Why skills-based hiring may be a better model  How freelancers and fractional talent are changing the workforce  Why AI could create more opportunity instead of less  What faster, leaner business growth may look like in the near future If you’ve been buried in admin, wearing every hat, and wondering how to grow without burning out, this episode will help you rethink what hiring can look like now. 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)

    39 min

  5. May 12

    Why So Many Entrepreneurs Look Successful but Feel Disconnected

    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 while building a business. This is not just a conversation about therapy. It is a conversation about the inner side of entrepreneurship. Joe shares his own turning points in business and life, including the realization that real success is not just about money, growth, or looking successful from the outside. Tara explains how high-functioning professionals, especially self-employed people and Type A personalities, often become the fixers for everyone else while neglecting what is happening within themselves. Together, they discuss: why high performers often struggle most in their personal livesthe emotional cost of entrepreneurshipwhy self-awareness matters in businesshow childhood beliefs can shape adult decision-makingthe difference between owning a job and building a businessburnout, relationships, and work-life imbalancewhy leadership starts internallythe power of simple, concrete steps when making hard changesIf you are a self-employed professional trying to grow a business without losing yourself in the process, this episode will hit home. Connect with Tara: Inner Light Integrative Therapy Email: info@healinginnerlight.com 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)

    33 min

  6. May 5

    He Woke Up From a Coma and Rebuilt His Life From Scratch Episode

    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, waking up from a coma after a traumatic brain injury, and slowly rebuilding the basic skills most people take for granted. What followed was not just a recovery story — it was an entrepreneurial journey filled with setbacks, reinvention, service, and impact. This conversation goes far beyond business. It’s about mindset, persistence, faith, healing, and what it means to keep moving forward one step at a time when the future feels uncertain. In this episode, you’ll hear:  Vincent’s story of surviving a traumatic brain injury  What recovery looked like in the earliest days  The emotional toll on families and caregivers  Why communication is so critical after a brain injury  How Vincent rebuilt his skills and confidence over time  The parallels between recovery and the entrepreneurial journey  How he turned his experience into coaching, books, podcasting, and service  Why your story can become your mission  How podcasting became part of his business and impact strategy This episode is deeply inspiring for anyone who has ever faced a major setback, questioned whether they could keep going, or wondered if something meaningful could still come from a painful chapter. 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)

    37 min

  7. Apr 28

    Know Your Numbers or Risk Losing Your Business

    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 owner should be monitoring on a regular basis. This is not about drowning in reports or obsessing over random data. It is about knowing which numbers actually help you make better decisions, reduce stress, spot problems early, and build a stronger business. Joe explains why checking your bank balance is not enough, how to think about revenue, lead flow, conversion rate, cash reserves, pipeline value, client concentration, and capacity, and why a simple KPI dashboard can help you see trouble coming before it becomes a crisis. If you want to stop guessing and start leading your business with clarity, this episode will help you focus on the numbers that matter most. In this episode, Joe covers:  Why bank balance is a terrible way to run a business  The difference between tracking too little and tracking too much  The weekly and monthly numbers that matter most  How lead flow and conversion rate affect sales  Why cash reserves reduce business stress  How to measure pipeline value and identify risk  Why client concentration can quietly hurt your business  How capacity and utilization reveal when it is time to hire or delegateIf 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) #SmallBusiness #KPIs #BusinessGrowth #CashFlow #Profitability #SelfEmployed #Entrepreneurship #BusinessStrategy #FinancialClarity #Dashboard 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)

    19 min

  8. Apr 21

    Why Small Business Owners Are Desperate for a CFO Right Now

    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 anymore. They want guidance. They want clarity around cash flow, profitability, hiring decisions, pricing, and growth. They want someone who can help them understand what the numbers mean before they make the next big move. Joe explains the real difference between an accountant and a CFO, why cash flow matters just as much as profit, how better financial insight leads to better decisions, and why AI is making strategic financial guidance more valuable, not less. If you are a business owner who wants more confidence in your decisions, or a financial professional looking to increase your value in the marketplace, this episode is for you. 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 You tube 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)  #SmallBusiness #VirtualCFO #CashFlow #Profitability #BusinessGrowth #SelfEmployed #Entrepreneurship #Accounting #CFO #SmallBusinessOwner  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
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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
    28
  • Rating
    Clean
  • Copyright
    © 2026 How to Win BIG at Business
  • Show Website
    How to Win BIG at Business