How to Win BIG at Business
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.
How to Win BIG at Business
Latest Episodes
Caught in the IRS Collection Machine? Here’s What Happens Next
Getting a bill from the IRS can be scary—but owing money doesn’t mean the IRS suddenly shows up and takes your bank account.There is a collection process, and understanding how that process works can give you valuable time to take...
Haven’t Filed Taxes in Years? Here’s How to Fix It
Haven’t filed a tax return in three years? Five years? Maybe even ten?Ignoring the problem might feel easier today—but it can make the situation far more difficult tomorrow.In this episode of How to Win BIG at Business, Joe...
Got an IRS Notice? Don’t Panic — Here’s What to Do Next
That IRS notice isn't junk mail — and being afraid to open it can turn a manageable problem into a much bigger one.For many taxpayers and business owners, just seeing an envelope from the IRS is enough to cause panic.But an...
Owe the IRS money? The worst thing you can do is ignore it.
Owe the IRS money? The worst thing you can do is ignore it.Whether your tax debt is $5,000, $50,000, $100,000 or more, fear and embarrassment can cause you to freeze. But ignoring IRS notices, unfiled returns, unpaid balances, lie...
A Profitable Business Can Still Go Broke: The Cash Flow System Every Owner Needs
In this episode of How to Win Big at Business, Joe DiChiara explains one of the most dangerous mistakes small business owners make: running the business by looking at the bank balance.Joe breaks down why cash flow is not simply “what’s l...
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