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
25 episodes
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...
Pricing Your Services the Smart Way
In this episode of How to Win Big at Business, Joe DiChiara, CPA, tackles one of the biggest challenges self-employed professionals face: pricing.How do you avoid undercharging and burning out?How do ...
Difficulty Finding Quality Clients? It’s Not the Market—It’s Your Positioning
If you keep attracting price shoppers, problem clients, or people who don’t value your work, this episode is for you.In this episode of How to Win Big at Business, Joe DiChiara, CPA explains why most self-employed professionals ...
The Uneven Revenue Problem
Uneven revenue is one of the biggest stress points for business owners — and almost nobody talks about it honestly.In this episode of How to Win Big at Business, Joe DiChiara, CPA and lifelong entrepreneur, tackles the reality of feast-o...
With Larry Broughton
In this episode of How to Win Big at Business, Joe welcomes Larry Broughton for a candid, no-BS conversation about what it truly takes to succeed as an entrepreneur.In January 2001, Larry Broughton founded Orange County, California-based...
How to Systematize Your Taxes and Eliminate Anxiety
In Episode 9, Joe DiChiara gets practical and tactical about one of the biggest stress points for self-employed professionals: tax anxiety.Joe explains that most tax-related stress is self-inflicted, not because people are careless, but ...
Avoiding the Pain and Confusion of Tax Season
In Episode, Joe DiChiara tackles the growing anxiety self-employed professionals feel every January when tax season begins.Joe explains that tax stress doesn’t come from taxes themselves—it comes from lack of structure, poor bookkeeping ...
Why Most Self-Employed Professionals Are Always Busy… but Still Broke
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...
The Top 5 Mistakes Self-Employed Professionals Make (And How to Avoid Them)
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 ...
Featuring Vincent A. Lanci Expert Podcaster & Podcast Producer
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...
Start Small, Start Smart: The Micro-Course Formula for New Entrepreneurs
In this episode of How to Win Big at Business, Joe DiChiara, CPA, explains why micro-courses are the most accessible and effective way for entrepreneurs to launch or expand a business—especially if you're short on time...
Monetize Your Genius Through Course Creation
In Episode 4 of How to Win Big at Business, Joe DiChiara, CPA, reveals why creating online courses is the fastest and easiest way to grow—or even start—a business. Whether you’re an expert, a hobbyist, or someone who thinks they “don’...
The Secret to Staying Motivated: Why Winners Eat Discipline for Breakfast
Running a business is tough — and some days, so is getting out of bed. In this episode of How to Win Big at Business, Joe DiChiara, CPA and lifelong entrepreneur, pulls back the curtain on one of the biggest struggles every business owner faces...
When Your Business Actually Starts (And Why It Matters More Than You Think)
In this episode, Joe DiChiara, CPA and lifelong entrepreneur, cuts straight to one of the biggest mysteries in the small-business world: When does a business actually begin? (Here’s a hint — it’s not when you mak...
Welcome to How to Win Big at Business: The Real Truth About Entrepreneurship
Running a business shouldn’t feel like a constant guessing game — and on this podcast, it won’t. Welcome to How to Win Big at Business, the show where entrepreneurs, solopreneurs, and consultants come to get the clarity...