How to Win BIG at Business With Accountants
Being a solopreneur or small business owner isn’t easy—you’re wearing all the hats, managing clients, handling finances, staying compliant, 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 With Accountants delivers straight talk, practical strategies, and real stories that help you cut through the noise and focus on what really moves the needle.
Now, Joe is also bringing in insights, advice, and real-world experience from accountants, tax preparers, CPAs, enrolled agents, and other small business professionals who understand what business owners are facing every day. These conversations are designed to help you avoid costly mistakes, understand the rules, keep better records, make smarter tax decisions, and build a stronger business with less confusion.
Each week, we dive into topics like:
Smarter tax and money strategies
Insights from accountants and tax preparers
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
Avoiding compliance traps before they become expensive problems
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 With Accountants
Latest Episodes
Why Small Business Owners Need Accountants More Than Ever
Small business owners are tired, frustrated, and confused by the never-ending stream of tax rules, compliance issues, payroll requirements, sales tax laws, IRS notices, state regulations, and all the things they “don’t know they don’t know.”
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...
When AI Says No: A Wake-Up Call for Business Owners
What happens when an AI tool stops acting like a tool — and starts making decisions for you?In this episode of How to Win Big at Business, Joe DiChiara shares a personal experience with Claude AI that started as a simple project: trackin...
Tax Compliance Is Not Optional: Protect Your Business Before the IRS Comes Calling
Tax compliance may feel painful, annoying, and overwhelming — but it is not optional.In this episode of How to Win Big at Business, Joe DiChiara speaks directly to self-employed professionals and small business owners who are f...
Build the Business of Your Life: A Wake-Up Call for Self-Employed Professionals
What if planning your business could feel like planning the best trip of your life?In this episode of How to Win Big at Business, Joe DiChiara invites self-employed professionals, solopreneurs, and small business owners to imagine...
Podcasts we love
Check out these other fine podcasts recommended by us, not an algorithm.
That Entrepreneur Show
Vincent A. Lanci
A Mental Health Break
Vincent A. Lanci