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
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 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.
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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