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In this episode of How to Win Big at Business, Joe welcomes Larry Broughton for a candid, no-BS conversation about what it truly takes to succeed as an entrepreneur.

In January 2001, Larry Broughton founded Orange County, California-based broughtonHOTELS, a leader in the boutique hotel industry. During what proved to be the worst two-and-a-half year period in the hospitality industry since before World War II, Broughton successfully acquired four hotel properties. The company’s portfolio eventually grew to nearly 20 hospitality projects throughout California and Chicago, IL.

Since its inception, Larry has received several business awards, including Ernst & Young’s Entrepreneur of the Year®; the National Veteran-Owned Business Association’s Vetrepreneur® of the Year; Coastline Foundation’s Visionary of the Year; Passkeys Foundation’s National Business Leader of Integrity; HSMAI’s 2018 Best of the Best Management Company of the Year; Fodor’s Top US Luxury Hotel; TripAdvisor’s Travelers’ Choice Awards; and Entrepreneur Magazine included the firm on their Hot 500 List of Fastest Growing Private Companies. NEWH (Network of Executive Women in Hospitality) says, Larry is among “the most exciting minds of hospitality.”

He shares insights from real business experience—wins, losses, hard lessons, and the decisions that shaped his journey. Together, they unpack the mindset, strategy, and discipline required to build and sustain a successful business in today’s world.

This episode is especially valuable for:

• Small business owners feeling stuck or overwhelmed
  
  
• Entrepreneurs navigating growth decisions
  
  
• Anyone who wants practical insight—not textbook advice

If you’ve ever wondered why some businesses break through while others stall, this episode will give you clarity, perspective, and actionable takeaways.

🎙 Listen now and learn how to win bigger—and smarter—at business.

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)

Send us a text

In Episode 9, Joe DiChiara gets practical and tactical about one of the biggest stress points for self-employed professionals: tax anxiety.

Joe explains that most tax-related stress is self-inflicted, not because people are careless, but because they don’t have systems. Drawing from his experience as a CPA and lifelong entrepreneur, he walks listeners through a step-by-step method to systematize their personal tax return so tax season becomes predictable instead of painful.

This episode focuses on:

• Why tax anxiety comes from confusion, not taxes themselves
  
  
• How reviewing prior-year tax returns eliminates uncertainty
  
  
• Understanding the structure of your tax return (income, adjustments, deductions, payments)
  
  
• Creating a checklist of required tax documents before filing
  
  
• Why third-party documents are often late or wrong — and how to catch errors
  
  
• The dangers of assuming tax forms are always correct
  
  
• How to handle delayed K-1s and corrected 1099s
  
  
• Non-cash deductions most people miss (clothing, furniture, books, cars)
  
  
• Why the home office deduction is a red audit flag for sole proprietors
  
  
• How S-Corp owners legally deduct home office expenses using an accountable plan

Joe reinforces a core principle: personal tax returns don’t change much year to year, and once you understand last year’s return, you’ve already won half the battle.

He closes with a reminder that systems don’t just reduce taxes — they reduce stress, mistakes, and fear.

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)

Send us a text

In Episode 8, Joe DiChiara tackles the growing anxiety self-employed professionals feel every January when tax season begins.

Joe explains that tax stress doesn’t come from taxes themselves—it comes from lack of structure, poor bookkeeping habits, and not understanding your numbers. He walks listeners through the foundational steps every business owner must take to eliminate surprises, reduce anxiety, and regain control long before a tax return is ever filed.

Key themes in this episode include:

• Why tax season feels overwhelming for small business owners
  
  
• How modern tools (QuickBooks, apps, AI) can create confusion instead of clarity
  
  
• Why accurate books and records are the foundation of stress-free taxes
  
  
• The importance of daily business habits and documentation
  
  
• Understanding your income statement and balance sheet
  
  
• Why tax returns are a once-a-year result, not a strategy
  
  
• The danger of waiting until year-end to think about taxes
  
  
• Why self-employed professionals need an accountant—not just a tax preparer
  
  
• How proactive accounting saves more money than it costs
  
  
• Why knowing your numbers is non-negotiable for real business success

Joe emphasizes that successful entrepreneurs don’t guess—they know their numbers. And if you haven’t done that yet, the best time to start is now.

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)

Send us a text

In this episode, I tackle one of the most frustrating realities of self-employment:

👉 You can be insanely busy and still not making real money.

I break down why so many self-employed professionals stay trapped in a cycle of overwork, stress, and inconsistent income—and it has nothing to do with effort or talent.

We’ll talk about:

• Why “being busy” is not the same as building a business
  
  
• The dangerous difference between income-producing work and busywork
  
  
• How most self-employed people accidentally create a job instead of a scalable business
  
  
• The mindset and systems shift required to finally get leverage

If you’re working nonstop but feel like you’re spinning your wheels, this episode will hit home—and more importantly, show you what to fix first.

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)

Send us a text

In today’s episode, I break down what I believe are the five biggest mistakes self-employed professionals make—mistakes I’ve seen over and over again after working with thousands of business owners over the last 40+ years.

And here’s the key thing to understand:
These mistakes are all connected. Fix one, and you often start fixing the others.

We kick things off with Mistake #5—not hiring a business-oriented CPA—and why simply having “an accountant” is not enough. I explain what separates a true business advisor from a tax preparer, the exact questions you should be asking before you hire a CPA, and why waiting until tax season to look at your numbers is a recipe for stress and missed opportunities.

From there, we move into:

• Why not understanding your financials (profit & loss, balance sheet, cash flow) keeps you stuck and reactive
  
  
• Why doing everything yourself—especially bookkeeping—is costing you more than money
  
  
• Why not asking for help is not a strength, but a hidden weakness that slows growth
  
  
• How not knowing your own strengths leads to poor hires, burnout, and wasted effort
  
  
• Why the vast majority of business owners are structured incorrectly, and how that mistake alone can cost you thousands in unnecessary taxes
  
  
• And finally, why so many self-employed professionals leave legal tax write-offs on the table, simply because they don’t know what they’re entitled to once they’re “in business”

This episode is especially for consultants, coaches, freelancers, and other self-employed professionals who want less stress, better decisions, and a stronger foundation for growth.

If you’ve ever said:

• “I don’t really know my numbers”
  
  
• “I’ll deal with it at tax time”
  
  
• “I should probably be structured differently”
  
  
• or “I feel like I’m missing something important”

…this episode will hit home.

🎧 Tune in, take notes, and I’ll see you in Episode 7.

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)

Send us a text

In this powerful guest episode, Joe DiChiara welcomes award-winning podcaster and author Vincent A. Lanci, whose remarkable story of survival and reinvention has inspired audiences around the world. After being struck by a car, placed in a coma, and told he might never walk or live independently again, Vincent rebuilt his life from the ground up—and eventually built a top-tier podcasting business.

Joe and Vincent dive into:
• The real emotional and financial challenges of entrepreneurship
• How trauma shaped Vincent’s resilience and mission
• The birth of That Entrepreneur Show and A Mental Health Break
• Using networking, resourcefulness, and mentorship to build a business
• The moment Vincent realized he could monetize his skills
• How he overcame a devastating summer downturn, failed payments, and client losses
• Why adversity is often the catalyst for growth
• Practical advice for new and aspiring entrepreneurs

Listeners will walk away with powerful insights on mindset, perseverance, and building a business with purpose.

Connect with the Guest:
Website: VincentALanci.com
Email: info@VincentALanci.com
Podcasts: That Entrepreneur Show, A Mental Health Break, Pod O’Clock

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)

Send us a text

In this episode of How to Win Big at Business, Joe DiChiara, CPA, explains why micro-courses are the most accessible and effective way for entrepreneurs to launch or expand a business—especially if you're short on time, experience, or technical skills.

Joe discusses the emotional roller coaster of entrepreneurship and how micro-courses provide stability, new revenue streams, and increased authority. He breaks down the essentials of building your first course, the equipment you actually need, and the platforms best suited for beginners and growing creators.

Listeners will learn:
• Why your first course should be small, focused, and fast to produce
• How authenticity beats perfection in online education
• How to choose the right platform (Zoom, Loom, Thinkific, Go High Level, Kajabi, Teachable)
• Why short 3–5 minute lessons outperform long presentations
• How to test and refine your course from a student’s perspective
• How micro-courses can evolve into full course series and long-term digital assets

Joe also offers podcast listeners a complimentary 20-minute strategy call to help map out their business or course creation plan. www.timewithjoe.com

This episode is ideal for new entrepreneurs, overwhelmed business owners, and anyone ready to monetize their expertise through simple, scalable digital products.

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)

Send us a text

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)