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)