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
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, confidence, and straight-talk strategies they need to grow without the overwhelm.
Hosted by Joe DiChiara, CPA — a 40-year entrepreneur, bestselling author, AI-powered business coach, and creator of the Business-in-a-Box system — this podcast blends old-school wisdom with modern tools to help everyday business owners win bigger, faster, and smarter.
In this maiden episode, Joe shares:
- Why entrepreneurship isn’t for the faint of heart
- His journey from running a casino in his driveway at age 10 to advising thousands of business owners
- The real highs, lows, setbacks, and breakthroughs that shape a business
- The surprising mistakes that derail most new entrepreneurs — and how to avoid them
- How to build a business you love without burning out, going broke, or getting blindsided
- Why mindset, systems, and preparation matter more than talent
- How clarity and confidence beat hustle and chaos every time
Joe’s style is part educator, part coach, part Brooklyn-born truth-teller. You’ll get insights you can use immediately — delivered with humor, encouragement, and a no-nonsense focus on helping you build a business that supports your life (instead of swallowing it whole).
This podcast is for you if you want to learn:
- How to start and scale a business the right way
- How to handle taxes, money, and compliance
- How to stay out of trouble with the IRS
- How to use AI tools to save time and grow revenue
- How to create simple systems that eliminate chaos
- How to avoid the biggest mistakes new business owners make
- How to develop the mindset and resilience to win big in business and in life
Whether you’re just getting started, rebuilding after a setback, or ready to level up, Joe is here to inform, prepare, and empower you every step of the way.
New episodes drop weekly.
Subscribe now and start winning big — in business and in life.
Thanks for listening!
If you want fewer headaches, fewer IRS surprises, and more smart systems running your business (so YOU don’t have to), let’s talk.
Book a strategy call: www.timewithjoe.com
Because running a business shouldn’t feel like wrestling an octopus… alone.
Also check out:
www.Bedrock360BusinessSolutions.com (Complete Coverage)
www.Bedrock360TaxSolutions.com (Tax Gaurd 365)
www.Bedrock360BusinessTraining.com (Courses)
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