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.
Episodes
38 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...
You Don’t Have a Time Problem — You Have a Focus Problem
Do you ever finish a long workday completely exhausted… but still wonder what you actually accomplished?You’re not alone.For many self-employed professionals and small business owners, the real problem isn’t a lack of time....
Is Your Accountant Helping You Win—or Just Filing Your Taxes?
A practical guide for self-employed professionals who want an accountant who helps them understand the numbers, plan ahead, protect their information, and make better business decisions. Do you have an accountant?Is your acco...
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.”
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...
The IRS Audit Wave Is Coming: Why Business Owners Must Fix Their Records Now
The IRS may be quiet right now, but Joe DiChiara warns business owners not to get too comfortable.In this episode of How to Win Big at Business, Joe explains why the next wave of IRS audits may look very different from the old day...
Confused About AI? Start Here Before You Waste Time and Money
If AI has you overwhelmed, this episode will help you stop spinning, focus on what matters, and start using it in a way that actually helps your business.You are not alone.In this episode of How to Win Big at Busines...
Still Doing Everything Yourself? This May Be Why You’re Stuck
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 Busi...
Why So Many Entrepreneurs Look Successful but Feel Disconnected
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 ...
He Woke Up From a Coma and Rebuilt His Life From Scratch Episode
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 ...
Know Your Numbers or Risk Losing Your Business
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 ...
Why Small Business Owners Are Desperate for a CFO Right Now
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 bec...
Overwhelmed by AI Tools? How Self-Employed Professionals Can Use Google Notebook LM
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 bur...
The Freedom Formula: Strengths, Visibility, and the Right Business Model
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 navig...
From Nurse to Entrepreneur: Marge Aviso’s Journey to 1,600 Employees
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 ...
AI Is NOT Replacing You — It’s Making You Richer (If You Use It Right)
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 technolog...
Why Most Solopreneurs Struggle With Revenue (And How to Build Predictable Recurring Income)
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, CP...
The Business Structure Mistake Costing Entrepreneurs Thousands
In this episode of How to Win Big at Business, Joe DiChiara, CPA, tackles one of the most expensive mistakes self-employed professionals make: choosing the wrong legal and tax structure.Many entrepreneurs...