How to Win BIG at Business and Taxes

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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: staying motivated when life (and business) keeps throwing haymakers.

Joe shares the simple truth: motivation is unreliable… but habits and discipline? They’ll carry you when your “why” is still asleep.

With his signature blend of wisdom, humor, and Brooklyn-born bluntness, Joe unpacks:

🔥 Why even successful entrepreneurs occasionally fantasize about getting a “normal job”

 🔥 How habits become your secret weapon when motivation packs its bags

 🔥 Joe’s own daily routine — including his massage gun, stretching, and the occasional strategic nap

 🔥 How Benjamin Franklin’s “Moral Perfection Project” can keep modern entrepreneurs grounded

 🔥 The 17 success principles of Napoleon Hill… and how Joe adapted them into his own 13 guiding rules

 🔥 Why taking a nap might be the most productive thing you do all day

 🔥 How faith, focus, and a little bit of humor can pull you through the roughest seasons in business

You’ll walk away with practical tools, a deeper sense of clarity, and maybe the comforting realization that every entrepreneur feels like quitting sometimes — the winners are just the ones who keep getting up.

If you’ve ever had a “Why did I start this business?!” moment… this episode is your permission slip to breathe, reset, and get back on track.

New episodes every week.
Subscribe now and learn how to win big — one habit at a time.

If you’re a self-employed professional trying to build a real business, this podcast was created for you.

New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner.

Subscribe to our YouTube Channel
https://www.youtube.com/@Bedrock360BusinessSolutions/featured
Thanks for listening!

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 Guard 365) 

www.Bedrock360BusinessCourses.com (Courses)

Send us Fan Mail

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 make your first dollar.)

Joe breaks down what really happens the moment you have a profit motive and take your first action — whether that’s buying a laptop, driving to Staples, or simply launching an idea that “defies logic.”

Because let’s be honest:

Real entrepreneurs ARE delusional.
And that’s exactly why they create, innovate, and challenge the world — even if most of their ideas should probably stay on the cutting-room floor.

In this episode, Joe tackles essential topics every entrepreneur must understand:

• The two requirements that officially start your business
• Why your car, computer, phone, and even a portion of your home become legitimate tax write-offs
• The hidden danger of commingling funds (and how it sinks entrepreneurs)
• The truth about audits in the AI era
• Why bootstrappers put themselves at risk by avoiding accountants
• The myth of “I’ll hire a CPA when I’m making money”
• Why most QuickBooks DIYers end up with a financial train wreck
• The real cost of flying solo — and the peace of mind of having a pro on your side

Joe also shares stories from the trenches — including IRS war stories, audit nightmares, and business owners unknowingly throwing away thousands of dollars in deductions because nobody ever told them the rules.

If you’re serious about building a business — not a hobby — this episode is a must-listen.
 And if you’ve ever wondered whether your Thanksgiving dinner could be a business write-off… yeah, Joe covers that too.

Subscribe for weekly episodes that help you avoid the pain, protect your profits, and win big at business — one smart decision at a time.

If you’re a self-employed professional trying to build a real business, this podcast was created for you.

New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner.

Subscribe to our YouTube Channel
https://www.youtube.com/@Bedrock360BusinessSolutions/featured
Thanks for listening!

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 Guard 365) 

www.Bedrock360BusinessCourses.com (Courses)

Send us Fan Mail

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.

If you’re a self-employed professional trying to build a real business, this podcast was created for you.

New episodes break down the systems, strategies, and structures needed to move from solopreneur to sustainable business owner.

Subscribe to our YouTube Channel
https://www.youtube.com/@Bedrock360BusinessSolutions/featured
Thanks for listening!

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 Guard 365) 

www.Bedrock360BusinessCourses.com (Courses)