How to Win BIG at Business

Send us Fan MailWhat 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.comBecause 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)

Send us Fan MailMost 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 Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featuredThanks 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.comBecause 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 #DashboardThanks 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.comBecause 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)

Send us Fan MailWhat 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 Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featuredThanks 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.comBecause 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.comBecause 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)

Send us Fan MailIn 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 down what makes Google NotebookLM different from tools like ChatGPT, Gemini, and Claude. Instead of pulling information from the entire internet, NotebookLM lets you work from the specific sources you choose. That makes it a practical tool for business owners who want better research, better organization, stronger training systems, and fewer bad AI answers.In this episode, they discuss:why business owners should master one AI platform instead of chasing every new toolhow NotebookLM can help with SOPs, onboarding, and internal trainingwhy AI should be treated like a gifted internhow to think about hallucinations and verificationwhy cybersecurity matters even more for small business owners todayIf you are a self-employed professional looking for a smarter, safer, and more practical way to use AI in your business, 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 Youtube Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featuredThanks 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.comBecause 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)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.comBecause 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)

Send us Fan MailIn 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 and community that opened major doors for her business. This conversation is full of lessons for self-employed professionals who want to attract clients, grow their authority, and build a business around their true strengths instead of staying trapped in work that drains them. Marianne explains why authenticity matters, how trust drives sales, why consistency on LinkedIn works, and how mentors, community, and trial-and-error helped shape her path. Joe and Marianne also talk about: the pain of career transition  the realities of freelancing and entrepreneurship  how to use social media to build visibility  why personal branding creates opportunities  the importance of mentors and coaches  finding your “why” and your real superpower  building freedom through service and alignment This is a powerful episode for anyone who wants more than income—they want freedom, purpose, and a business they truly enjoy building. Suggested Show Notes Bullets Marianne’s journey from corporate finance to entrepreneurship  What the pandemic taught her about adaptability  How she got started in freelancing and online work  Why trust and authenticity matter in sales  How she built visibility through LinkedIn content  The role of community, mentors, and coaching in growth  Why entrepreneurs need to find their strengths  How personal branding leads to clients and opportunities  What freedom really means as a business owner Buzzsprout Hashtags#Entrepreneurship #PersonalBranding #LinkedInMarketing #BusinessGrowth #Freelancing #SelfEmployed #ClientAttraction #OnlineBusiness #Coaching #WorkFromHomeSubscribe to the PodcastIf 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 Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featuredThanks 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.comBecause 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)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.comBecause 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)

Send us Fan MailIn 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 decisions that come with leadership. She opens up about what happened when unclear bookkeeping and poor financial visibility left her business exposed, and how she fought back by learning her numbers, restructuring operations, accelerating collections, cutting unnecessary costs, and rebuilding with stronger systems. This episode is packed with lessons for self-employed professionals and business owners who want to strengthen their cash flow, understand their financials, lead through adversity, and build a business that creates both income and freedom. It also highlights the power of resilience, values-driven leadership, and the loyalty that comes from building the right team culture. Subscribe to the PodcastIf 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 Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featuredThanks 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.comBecause 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) #Entrepreneurship #BusinessGrowth #CashFlow #Leadership #SelfEmployed #SmallBusiness #FounderJourney #FinancialClarity #RemoteTeams #Outsourcing 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.comBecause 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)

Send us Fan MailAI 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 technological shift has created MORE opportunity for those willing to adapt.Learn how AI can help you: • Increase productivity dramatically • Create new services for clients • Scale your business without hiring more staff • Build digital products faster than ever • Position yourself ahead of competitorsIf you are a consultant, accountant, freelancer, coach, or independent professional, this episode will help you see AI as a powerful tool rather than a threat.Subscribe to the PodcastIf 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 Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featuredThanks 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.comBecause 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)

Send us Fan MailMost 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.Joe shares a real example of a business owner struggling with cash flow despite having a valuable service. The problem wasn’t the offer—it was the financial structure of the business.You’ll learn how to build a reliable revenue engine using communities, sales funnels, and low-barrier offers that convert leads into long-term clients.If you’re tired of the feast-or-famine cycle in your business, this episode will show you a smarter path forward.What You'll Learn in This Episode• Why great services fail without a revenue structure• The dangerous “big client” trap many entrepreneurs fall into• Why recurring revenue is the foundation of a real business• How to create a community that generates leads every day• The psychology behind low-cost entry offers• How to turn leads into high-value clients over timeKey Concept From This EpisodeA viable business needs two things:RevenuePositive cash flowWithout both, even great businesses struggle to survive.Subscribe to the PodcastIf 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 Channelhttps://www.youtube.com/@Bedrock360BusinessSolutions/featuredThanks 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.comBecause 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)

Send us Fan MailIn 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 LLC does NOT reduce taxes by itself• The difference between legal structure and tax classification• When to choose an S corporation• When a C corporation makes more sense• How net operating losses work• Why corporations are audited less frequently• How to retroactively elect S or C statusWith over four decades of experience serving self-employed professionals, Joe simplifies what most accountants overcomplicate.If you're earning 1099 income, this episode is essential.To book a discovery call:www.timewithjoe.comThanks 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.comBecause 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)

Send us Fan MailIn 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 story about offering $35 tax returns to build trust — and the surprising outcome when he later raised his fees dramatically.In this episode, Joe explains:• Why trust determines pricing power• How a sales funnel supports premium pricing• The importance of knowing your ideal client (“avatar”)• The 3 core ways to grow a business• Why some clients leaving can actually increase profits• How to implement strategic price increases• Why no complaints about pricing is a red flagJoe also discusses his recent pricing adjustments within his Bedrock 360 Tax Solutions model and why transparency builds long-term client loyalty.If you are self-employed and struggling with pricing confidence, this episode provides clarity and practical direction.To schedule a strategy call:www.timewithjoe.comThanks 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.comBecause 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)

Send us Fan MailIf 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 qualityHow selling services instead of outcomes attracts the wrong peopleThe power of clearly defining who you work with—and who you don’tHow better positioning leads to better clients, fewer headaches, and more referralsThis is a practical, no-hype conversation designed to help you stop chasing clients and start choosing them.🎯 Want to see if your positioning is holding you back?Schedule a strategy call: https://timewithjoe.comIf this episode helped you, follow the show and leave a review—it helps more business owners find clarity.#HowToWinBigAtBusiness#SelfEmployedProfessionals#SmallBusinessPodcast#ClientProblems#MarketingClarity#BusinessGrowth#EntrepreneurMindset#ServiceBusinessThanks 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.comBecause 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)

Send us Fan MailUneven 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 accounting practice — where half of annual revenue comes in just three months — Joe walks through:Why uneven cash flow happens in almost every industryThe first numbers every business owner must know (starting with their personal budget)How to calculate the real monthly income your business must produceWhy poor cash flow management destroys otherwise good businessesHow to align expenses, revenue cycles, and payment termsPractical steps to smooth cash flow without working harderIf you’re tired of great months followed by stressful ones, this episode will help you think differently — and operate smarter.🎙️ Hosted by Joe DiChiara, CPA 📊 Straight talk for entrepreneurs who want predictable, sustainable successThanks 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.comBecause 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)

Send us Fan MailIn 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 industry since before World War II, Broughton successfully acquired four hotel properties. The company’s portfolio eventually grew to nearly 20 hospitality projects throughout California and Chicago, IL.Since its inception, Larry has received several business awards, including Ernst & Young’s Entrepreneur of the Year®; the National Veteran-Owned Business Association’s Vetrepreneur® of the Year; Coastline Foundation’s Visionary of the Year; Passkeys Foundation’s National Business Leader of Integrity; HSMAI’s 2018 Best of the Best Management Company of the Year; Fodor’s Top US Luxury Hotel; TripAdvisor’s Travelers’ Choice Awards; and Entrepreneur Magazine included the firm on their Hot 500 List of Fastest Growing Private Companies. NEWH (Network of Executive Women in Hospitality) says, Larry is among “the most exciting minds of hospitality.”He shares insights from real business experience—wins, losses, hard lessons, and the decisions that shaped his journey. Together, they unpack the mindset, strategy, and discipline required to build and sustain a successful business in today’s world.This episode is especially valuable for:Small business owners feeling stuck or overwhelmedEntrepreneurs navigating growth decisionsAnyone who wants practical insight—not textbook adviceIf you’ve ever wondered why some businesses break through while others stall, this episode will give you clarity, perspective, and actionable takeaways.🎙 Listen now and learn how to win bigger—and smarter—at business.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.comBecause 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)

Send us Fan MailIn 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 to systematize their personal tax return so tax season becomes predictable instead of painful.This episode focuses on:Why tax anxiety comes from confusion, not taxes themselvesHow reviewing prior-year tax returns eliminates uncertaintyUnderstanding the structure of your tax return (income, adjustments, deductions, payments)Creating a checklist of required tax documents before filingWhy third-party documents are often late or wrong — and how to catch errorsThe dangers of assuming tax forms are always correctHow to handle delayed K-1s and corrected 1099sNon-cash deductions most people miss (clothing, furniture, books, cars)Why the home office deduction is a red audit flag for sole proprietorsHow S-Corp owners legally deduct home office expenses using an accountable planJoe reinforces a core principle: personal tax returns don’t change much year to year, and once you understand last year’s return, you’ve already won half the battle.He closes with a reminder that systems don’t just reduce taxes — they reduce stress, mistakes, and fear.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.comBecause 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)

Send us Fan MailIn 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 surprises, reduce anxiety, and regain control long before a tax return is ever filed.Key themes in this episode include:Why tax season feels overwhelming for small business ownersHow modern tools (QuickBooks, apps, AI) can create confusion instead of clarityWhy accurate books and records are the foundation of stress-free taxesThe importance of daily business habits and documentationUnderstanding your income statement and balance sheetWhy tax returns are a once-a-year result, not a strategyThe danger of waiting until year-end to think about taxesWhy self-employed professionals need an accountant—not just a tax preparerHow proactive accounting saves more money than it costsWhy knowing your numbers is non-negotiable for real business successJoe emphasizes that successful entrepreneurs don’t guess—they know their numbers. And if you haven’t done that yet, the best time to start is now.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.comBecause 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)

Send us Fan MailIn 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 businessThe dangerous difference between income-producing work and busyworkHow most self-employed people accidentally create a job instead of a scalable businessThe mindset and systems shift required to finally get leverageIf you’re working nonstop but feel like you’re spinning your wheels, this episode will hit home—and more importantly, show you what to fix first.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.comBecause 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)

Send us Fan MailIn 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—not hiring a business-oriented CPA—and why simply having “an accountant” is not enough. I explain what separates a true business advisor from a tax preparer, the exact questions you should be asking before you hire a CPA, and why waiting until tax season to look at your numbers is a recipe for stress and missed opportunities.From there, we move into:Why not understanding your financials (profit & loss, balance sheet, cash flow) keeps you stuck and reactiveWhy doing everything yourself—especially bookkeeping—is costing you more than moneyWhy not asking for help is not a strength, but a hidden weakness that slows growthHow not knowing your own strengths leads to poor hires, burnout, and wasted effortWhy the vast majority of business owners are structured incorrectly, and how that mistake alone can cost you thousands in unnecessary taxesAnd finally, why so many self-employed professionals leave legal tax write-offs on the table, simply because they don’t know what they’re entitled to once they’re “in business”This episode is especially for consultants, coaches, freelancers, and other self-employed professionals who want less stress, better decisions, and a stronger foundation for growth.If you’ve ever said:“I don’t really know my numbers”“I’ll deal with it at tax time”“I should probably be structured differently”or “I feel like I’m missing something important”…this episode will hit home.🎧 Tune in, take notes, and I’ll see you in Episode 7.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.comBecause 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)

Send us Fan MailIn 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 entrepreneursListeners will walk away with powerful insights on mindset, perseverance, and building a business with purpose.Connect with the Guest: Website: VincentALanci.com Email: [email protected] Podcasts: That Entrepreneur Show, A Mental Health Break, Pod O’ClockThanks 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.comBecause 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)

Send us Fan MailIn 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 assetsJoe also offers podcast listeners a complimentary 20-minute strategy call to help map out their business or course creation plan. www.timewithjoe.comThis 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.comBecause 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)

Send us Fan MailIn 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.comThanks 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.comBecause 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)

Send us Fan MailRunning 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 businessYou’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.comBecause 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)

Send us Fan MailIn 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.comBecause 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)

Send us Fan MailRunning 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.comBecause 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)