Podcast thumbnail for How to Win BIG at Business

How to Win BIG at Business

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by Joe DiChiara

31 episodes
Updated Daily
Accepts GuestsHas Sponsors

Podcast Overview

<p>Being a solopreneur or small business owner isn’t easy—you’re wearing all the hats, managing clients, handling finances, staying compliant, and trying to grow without burning out. That’s where this podcast comes in.</p><p><br></p><p>Hosted by <b>Joe DiChiara, CPA, entrepreneur, and business mentor</b>, <b>How to Win BIG at Business With Accountants</b>&nbsp; delivers straight talk, practical strategies, and real stories that help you cut through the noise and focus on what really moves the needle.</p><p><br></p><p>Now, Joe is also bringing in insights, advice, and real-world experience from <b>accountants, tax preparers, CPAs, enrolled agents, and other small business professionals</b> who understand what business owners are facing every day. These conversations are designed to help you avoid costly mistakes, understand the rules, keep better records, make smarter tax decisions, and build a stronger business with less confusion.</p><p><br></p><p>Each week, we dive into topics like:</p><p>Smarter tax and money strategies<br>&nbsp;Insights from accountants and tax preparers<br>&nbsp;Using AI and automation to save time<br>&nbsp;Marketing that actually works without overwhelm<br>&nbsp;Building passive income streams<br>&nbsp;Protecting your business and scaling the right way</p><p>&nbsp;Avoiding compliance traps before they become expensive problems</p><p><br></p><p>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.</p><p><br></p><p>👉 Subscribe now and join a community of entrepreneurs who are rewriting the rules of success.</p>

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Publishing Since

12/2/2025

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Recent Episodes

Episode thumbnail for A Profitable Business Can Still Go Broke: The Cash Flow System Every Owner Needs

June 30, 2026

A Profitable Business Can Still Go Broke: The Cash Flow System Every Owner Needs

Send us Fan Mail In this episode of How to Win Big at Business, Joe DiChiara explains one of the most dangerous mistakes small business owners make: running the business by looking at the bank balance. Joe breaks down why cash flow is not simply “what’s left over” after paying bills. Cash flow should be a system — one that tells you where the money is going, what needs to be set aside, what belongs to the owner, what must be reserved for taxes, and what should be protected for future stabilit...

Episode thumbnail for When AI Says No: A Wake-Up Call for Business Owners

June 23, 2026

When AI Says No: A Wake-Up Call for Business Owners

Send us Fan Mail What happens when an AI tool stops acting like a tool — and starts making decisions for you? In this episode of How to Win Big at Business, Joe DiChiara shares a personal experience with Claude AI that started as a simple project: tracking calories, exercise, weight loss, and daily progress. Joe was using AI the way many self-employed professionals are beginning to use it — as a helper, organizer, calculator, and productivity tool. But then something unexpected happened. Afte...

Episode thumbnail for Tax Compliance Is Not Optional: Protect Your Business Before the IRS Comes Calling

June 17, 2026

Tax Compliance Is Not Optional: Protect Your Business Before the IRS Comes Calling

Send us Fan Mail Tax compliance may feel painful, annoying, and overwhelming — but it is not optional. In this episode of How to Win Big at Business, Joe DiChiara speaks directly to self-employed professionals and small business owners who are frustrated by the growing burden of invoices, receipts, payroll records, sales tax rules, tax filings, and government compliance. Joe opens with the voice of the frustrated business owner: “Why do I have to spend all this time submitting information? Wh...

31 total episodes available

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What is How to Win BIG at Business?
<p>Being a solopreneur or small business owner isn’t easy—you’re wearing all the hats, managing clients, handling finances, staying compliant, and trying to grow without burning out. That’s where this podcast comes in.</p><p><br></p><p>Hosted by <b>Joe DiChiara, CPA, entrepreneur, and business mentor</b>, <b>How to Win BIG at Business With Accountants</b>&nbsp; delivers straight talk, practical strategies, and real stories that help you cut through the noise and focus on what really moves the needle.</p><p><br></p><p>Now, Joe is also bringing in insights, advice, and real-world experience from <b>accountants, tax preparers, CPAs, enrolled agents, and other small business professionals</b> who understand what business owners are facing every day. These conversations are designed to help you avoid costly mistakes, understand the rules, keep better records, make smarter tax decisions, and build a stronger business with less confusion.</p><p><br></p><p>Each week, we dive into topics like:</p><p>Smarter tax and money strategies<br>&nbsp;Insights from accountants and tax preparers<br>&nbsp;Using AI and automation to save time<br>&nbsp;Marketing that actually works without overwhelm<br>&nbsp;Building passive income streams<br>&nbsp;Protecting your business and scaling the right way</p><p>&nbsp;Avoiding compliance traps before they become expensive problems</p><p><br></p><p>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.</p><p><br></p><p>👉 Subscribe now and join a community of entrepreneurs who are rewriting the rules of success.</p>
How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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