How to Win BIG at Business

By Joe DiChiara

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Image by Joe DiChiara

Category: Entrepreneurship

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Episodes: 28

Description

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.


Episode Date
Build the Business of Your Life: A Wake-Up Call for Self-Employed Professionals
Jun 09, 2026
The IRS Audit Wave Is Coming: Why Business Owners Must Fix Their Records Now
Jun 02, 2026
Confused About AI? Start Here Before You Waste Time and Money
May 26, 2026
Still Doing Everything Yourself? This May Be Why You’re Stuck
May 19, 2026
Why So Many Entrepreneurs Look Successful but Feel Disconnected
May 12, 2026
He Woke Up From a Coma and Rebuilt His Life From Scratch Episode
May 05, 2026
Know Your Numbers or Risk Losing Your Business
Apr 28, 2026
Why Small Business Owners Are Desperate for a CFO Right Now
Apr 21, 2026
Overwhelmed by AI Tools? How Self-Employed Professionals Can Use Google Notebook LM
Apr 14, 2026
The Freedom Formula: Strengths, Visibility, and the Right Business Model
Apr 07, 2026
From Nurse to Entrepreneur: Marge Aviso’s Journey to 1,600 Employees
Mar 31, 2026
AI Is NOT Replacing You — It’s Making You Richer (If You Use It Right)
Mar 24, 2026
Why Most Solopreneurs Struggle With Revenue (And How to Build Predictable Recurring Income)
Mar 18, 2026
The Business Structure Mistake Costing Entrepreneurs Thousands
Mar 10, 2026
Pricing Your Services the Smart Way
Mar 03, 2026
Difficulty Finding Quality Clients? It’s Not the Market—It’s Your Positioning
Feb 24, 2026
The Uneven Revenue Problem
Feb 17, 2026
With Larry Broughton
Feb 10, 2026
How to Systematize Your Taxes and Eliminate Anxiety
Feb 03, 2026
Avoiding the Pain and Confusion of Tax Season
Jan 27, 2026
Why Most Self-Employed Professionals Are Always Busy… but Still Broke
Jan 20, 2026
The Top 5 Mistakes Self-Employed Professionals Make (And How to Avoid Them)
Jan 13, 2026
Featuring Vincent A. Lanci Expert Podcaster & Podcast Producer
Jan 06, 2026
Start Small, Start Smart: The Micro-Course Formula for New Entrepreneurs
Dec 31, 2025
Monetize Your Genius Through Course Creation
Dec 26, 2025
The Secret to Staying Motivated: Why Winners Eat Discipline for Breakfast
Dec 16, 2025
When Your Business Actually Starts (And Why It Matters More Than You Think)
Dec 09, 2025
Welcome to How to Win Big at Business: The Real Truth About Entrepreneurship
Dec 02, 2025