How to Win BIG at Business Podcast By Joe DiChiara cover art

How to Win BIG at Business

How to Win BIG at Business

By: 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.

© 2026 How to Win BIG at Business
Economics Leadership Management & Leadership
Episodes
  • Guest Episode #3 From Nurse to Entrepreneur: Marge Aviso’s Journey to 1,600 Employees
    Mar 31 2026

    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)

    Show more Show less
    41 mins
  • Episode #15 AI Is NOT Replacing You — It’s Making You Richer (If You Use It Right)
    Mar 24 2026

    Send us Fan Mail

    AI 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 competitors

    If 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 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)

    Show more Show less
    27 mins
  • Episode #14 Why Most Solopreneurs Struggle With Revenue (And How to Build Predictable Recurring Income)
    Mar 18 2026

    Send a text

    Most 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 time

    Key Concept From This Episode

    A viable business needs two things:

    1. Revenue
    2. Positive cash flow

    Without both, even great businesses struggle to survive.


    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)

    Show more Show less
    20 mins
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