How to Win BIG at Business

About How to Win BIG at Business

How to Win Big at Business and Taxes is the podcast for self-employed professionals, entrepreneurs, and small business owners who want to make more money, keep more of what they earn, pay less in taxes legally, and build a business that works for them—not the other way around. Hosted by Joe DiChiara, CPA and entrepreneur, each episode delivers practical, straight-talking strategies for navigating both sides of entrepreneurship: building a better business and making smarter tax decisions. We tackle the issues that can make or break a small business—from profitability, cash flow, pricing, systems, marketing, and growth to tax planning, IRS problems, tax debt, compliance, deductions, entity structure, and avoiding expensive tax mistakes. You'll learn how to: Build a more profitable and sustainable business Understand the numbers that actually drive your success Improve cash flow and make smarter financial decisions Reduce your tax burden through proactive tax planning Avoid costly tax and compliance mistakes Understand IRS notices, tax debt, liens, levies, and collection options Use systems, technology, and AI to operate more efficiently Move from overwhelmed solopreneur to confident business owner You'll also hear from entrepreneurs and professionals who share the lessons, mistakes, strategies, and experiences that helped them build successful businesses. Because winning big isn't just about how much your business makes. It's about how much you keep, how well you protect it, and the freedom your business creates. 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, tax strategies, and structures needed to move from solopreneur to sustainable business owner. Subscribe to our YouTube Channel https://www.youtube.com/@Bedrock360BusinessSolutions/featured (https://www.youtube.com/@Bedrock360BusinessSolutions/featured) 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 (http://www.timewithjoe.com) Because running a business shouldn’t feel like wrestling an octopus… alone. Also check out: www.Bedrock360BusinessSolutions.com (http://www.Bedrock360BusinessSolutions.com) (Complete Coverage) www.Bedrock360TaxSolutions.com (http://www.Bedrock360TaxSolutions.com) (Tax Guard 365) www.Bedrock360BusinessCourses.com (http://www.Bedrock360BusinessCourses.com) (Courses)

Publisher

Joe DiChiara

Category

business

Language

en

Explicit

No

First episode

2 Dec 2025

Latest episode

20 Oct 2026

Latest episodes

44 episodes in the feed.

1. 

   20 Oct 2026

   Can You Get IRS Penalties Removed? Here's What the IRS Doesn't Tell You

   Send us Fan Mail "If you got an IRS notice saying you owe $25,000, would you assume you have to pay all of it? Most people would. But what if thousands of dollars of that balance were penalties and interest that could potentially be removed?" The IRS says you owe $25,000. But do you really have to pay every dollar? When you receive an IRS notice, the first thing you probably see is the balance due. What you may not realize is that the amount can include three very different things: unpaid tax...

2. 

   13 Oct 2026

   Can’t Afford to Pay the IRS? How Currently Not Collectible Status Works

   Send us Fan Mail What happens when you owe the IRS—but you genuinely cannot afford to pay them anything? Sometimes the right monthly payment isn't $5,000. It isn't $500. It isn't even $200. Sometimes, temporarily, it may be $0. In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA explains Currently Not Collectible (CNC) status—an IRS collection status designed for taxpayers experiencing financial hardship. Joe breaks down what CNC actually means, how financial hardship i...

3. 

   6 Oct 2026

   Can You Really Settle IRS Debt for Pennies on the Dollar?

   Send us Fan Mail The Truth About IRS Offers in Compromise You've seen the advertisements: “We settled $100,000 in IRS debt for $2,000!” Can that really happen? Yes. But there's a lot those advertisements aren't telling you. In this episode of How to Win BIG at Business, Joe DiChiara, CPA takes you behind the scenes of the IRS Offer in Compromise program and explains how the IRS actually determines whether someone may qualify to settle a tax debt for less than the full amount owed. An Offer in...

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Spotify

5.0 / 5

1 ratings

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.