How to Win BIG at Business

Joe DiChiara
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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. 6D AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. APR 14

    Overwhelmed by AI Tools? How Self-Employed Professionals Can Use Google Notebook LM

    Send us Fan Mail In 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 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 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.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)

    41 min

  7. APR 7

    The Freedom Formula: Strengths, Visibility, and the Right Business Model

    Send us Fan Mail In 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 #WorkFromHome Subscribe to the Podcast 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 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.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)

    50 min

  8. MAR 31

    From Nurse to Entrepreneur: Marge Aviso’s Journey to 1,600 Employees

    Send us Fan Mail In this episode of How to Win Big at Business, Joe talks with Marjorie “Marge” Aviso, co-owner of a successful BPO in the Philippines, about the real challenges behind entrepreneurial success.  Marge shares her journey from being a nurse and young mother to building a company with 1,600 employees, while navigating painful setbacks, financial mistakes, debt, and the hard 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 Podcast 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)  #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.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)

    41 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
    25
  • Rating
    Clean
  • Copyright
    © 2026 How to Win BIG at Business
  • Show Website
    How to Win BIG at Business