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How to Win BIG at Business

How to Win BIG at Business

Di: Joe DiChiara
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A proposito di questo titolo

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
Economia Gestione e leadership Leadership
  • Episode 7 Why Most Self-Employed Professionals Are Always Busy… but Still Broke
    Jan 20 2026

    Send us a text

    In 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 business

    • The dangerous difference between income-producing work and busywork

    • How most self-employed people accidentally create a job instead of a scalable business

    • The mindset and systems shift required to finally get leverage

    If 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.com

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:
    www.Bedrock360BusinessSolutions.com (Complete Coverage)

    www.Bedrock360TaxSolutions.com (Tax Gaurd 365)

    www.Bedrock360BusinessTraining.com (Courses)

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    22 min
  • Episode #6: The Top 5 Mistakes Self-Employed Professionals Make (And How to Avoid Them)
    Jan 13 2026

    Send us a text

    In 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 reactive

    • Why doing everything yourself—especially bookkeeping—is costing you more than money

    • Why not asking for help is not a strength, but a hidden weakness that slows growth

    • How not knowing your own strengths leads to poor hires, burnout, and wasted effort

    • Why the vast majority of business owners are structured incorrectly, and how that mistake alone can cost you thousands in unnecessary taxes

    • And 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.com

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:
    www.Bedrock360BusinessSolutions.com (Complete Coverage)

    www.Bedrock360TaxSolutions.com (Tax Gaurd 365)

    www.Bedrock360BusinessTraining.com (Courses)

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    21 min
  • Guest Episode #1 — Featuring Vincent A. Lanci Expert Podcaster & Podcast Producer
    Jan 6 2026

    Send us a text

    In 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 entrepreneurs

    Listeners will walk away with powerful insights on mindset, perseverance, and building a business with purpose.

    Connect with the Guest:
    Website: VincentALanci.com
    Email: info@VincentALanci.com
    Podcasts: That Entrepreneur Show, A Mental Health Break, Pod O’Clock



    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)

    Mostra di più Mostra meno
    34 min
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