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
The Business Structure Mistake Costing Entrepreneurs Thousands
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In this episode of How to Win Big at Business, Joe DiChiara, CPA, tackles one of the most expensive mistakes self-employed professionals make: choosing the wrong legal and tax structure.
Many entrepreneurs default into sole proprietorship or LLC status without understanding the long-term tax consequences.
Joe explains:
• Why 15.3% self-employment tax hits sole proprietors
• Why LLC does NOT reduce taxes by itself
• The difference between legal structure and tax classification
• When to choose an S corporation
• When a C corporation makes more sense
• How net operating losses work
• Why corporations are audited less frequently
• How to retroactively elect S or C status
With over four decades of experience serving self-employed professionals, Joe simplifies what most accountants overcomplicate.
If you're earning 1099 income, this episode is essential.
To book a discovery call:
www.timewithjoe.com
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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