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
Pricing Your Services the Smart Way
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In this episode of How to Win Big at Business, Joe DiChiara, CPA, tackles one of the biggest challenges self-employed professionals face: pricing.
How do you avoid undercharging and burning out?
How do you raise your prices without losing clients?
How do you know what the market will bear?
Drawing from over four decades advising entrepreneurs, Joe shares a powerful early-career story about offering $35 tax returns to build trust — and the surprising outcome when he later raised his fees dramatically.
In this episode, Joe explains:
• Why trust determines pricing power
• How a sales funnel supports premium pricing
• The importance of knowing your ideal client (“avatar”)
• The 3 core ways to grow a business
• Why some clients leaving can actually increase profits
• How to implement strategic price increases
• Why no complaints about pricing is a red flag
Joe also discusses his recent pricing adjustments within his Bedrock 360 Tax Solutions model and why transparency builds long-term client loyalty.
If you are self-employed and struggling with pricing confidence, this episode provides clarity and practical direction.
To schedule a strategy 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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