How to Win BIG at Business and Taxes

How to Win BIG at Business and Taxes

By Joe DiChiaraBusinessEntrepreneurship
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How to Win BIG at Business and Taxes episodes

  • Stop Attracting Bad Clients: Fix Your Business Positioning

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    Are you constantly attracting price shoppers, tire kickers, difficult clients, people who don't pay on time, or clients who simply don't appreciate what you do?

    The problem may not be your market.

    It may be your positioning.

    In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, explains why self-employed professionals frequently attract the wrong clients—and how clearer positioning can help change that.

    One of the most common marketing mistakes is trying to appeal to everyone.

    When your message is too broad, you sound like everybody else.

    When you only describe your services, prospects may not understand why they should choose you.

    And when you don't clearly identify who you help and what problem you solve, the wrong prospects can keep showing up.

    Joe discusses:

    • Why entrepreneurship is an ongoing journey
    • Why self-employment can be both difficult and rewarding
    • Why bad clients can be a symptom of bad positioning
    • Why trying to attract everyone can weaken your marketing
    • Why generic marketing messages don't stand out
    • The difference between selling services and selling outcomes
    • Why you should identify a specific person with a specific problem
    • How pain points help shape your positioning
    • Why prospects respond when they feel that you understand their situation
    • Why your website should clearly explain who your service is for
    • Why it can also help to explain who it isn't for
    • Why narrowing your market can make your message stronger
    • How to communicate the outcome your client wants
    • Why your business should be positioned as the bridge between a problem and a desired result
    • Why every marketing message needs a clear next step
    • How Joe identified self-employed professionals as his ideal audience
    • Why your ideal clients should be people you actually enjoy serving
    • Why better-fit clients are more likely to appreciate the service, pay their bills, and refer new business

    The core idea is simple:

    Don't try to convince everyone that they need you.

    Identify the people you can help best.

    Understand what they're struggling with.

    Communicate the outcome they want.

    Show them how you can help them get there.

    Then make the next step obvious.

    If you're attracting the wrong clients, don't automatically spend more money on advertising.

    Fix your positioning first.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)


    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    12 min
  • Making Money but Still Broke? Fix Your Uneven Cash Flow

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    Your business has a fantastic month.

    Money is coming in. The bank account looks healthy. You finally feel like you're getting ahead.

    Then the slow months arrive.

    Suddenly you're watching every dollar, wondering how you're going to cover payroll, business expenses—and your own bills.

    Sound familiar?

    Welcome to the uneven revenue problem.

    In this episode of How to Win BIG at Business, Joe DiChiara, CPA and lifelong entrepreneur, explains why uneven revenue and cash flow aren't unusual—they're part of running many businesses.

    Joe knows the problem firsthand. In his accounting business, a significant percentage of annual revenue historically arrives during a relatively short period of the year.

    The answer isn't simply "make more money."

    The answer is to know your numbers and actively manage your cash flow.

    In this episode, you'll learn:

    • Why your personal budget matters to your business
    • How to determine the minimum amount your business needs to produce
    • Why Joe recommends starting with a simple rolling personal budget
    • How to create a 12-month business budget
    • Why reliable financial statements are essential
    • How to identify the peaks and valleys in your revenue
    • Why a great month doesn't mean the next month will be great
    • How cash reserves protect you during unexpected downturns
    • Why payment terms can dramatically affect cash flow
    • How Joe changed the billing process in his own accounting firm
    • How vendor terms can help growing businesses manage working capital
    • When a business line of credit can help bridge cash-flow timing differences

    Uneven revenue doesn't automatically mean you have a bad business.

    But failing to prepare for those revenue swings can create a serious cash-flow problem.

    Know your numbers. Anticipate your slow months. Protect your cash. And take control before a cash-flow problem takes control of you.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    13 min
  • Hotelier, Award Winning Entrepreneur, Dad-The Amazing Larry Broughton

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    What does it really mean to win big at business?

    Is it revenue?

    Awards?

    Growth?

    Freedom?

    Or is real success bigger than the business itself?

    In this guest episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, sits down with his longtime coach, mentor, and friend Larry Broughton.

    Larry is a former U.S. Army Green Beret, entrepreneur, hotelier, business leader, author, mentor, and coach whose career took him from working as a night auditor at a small San Francisco hotel to becoming a partner in a hotel company that acquired approximately 14 properties over 14 years.

    But Larry's most important lessons didn't necessarily come from the successes.

    They came from mistakes, failures, personal loss, business struggles, and learning what happens when one area of life succeeds while everything else suffers.

    Larry shares how there was a period when business was booming, money was coming in, awards were piling up—and yet his family life, friendships, spiritual life, and other areas were falling apart.

    That experience changed the way he defined success.

    In this conversation, Joe and Larry discuss:

    • Why financial success alone may not equal a successful life
    • Larry's “whole health” framework for measuring the different areas of your life
    • Why success often means freedom
    • Why your definition of success can change over time
    • Why entrepreneurs need contingency plans
    • Why failure should be followed by an after-action review
    • The misleading image of entrepreneurship often presented on social media
    • Why business ownership can become lonely
    • The importance of trusted mentors and accountability groups
    • Why entrepreneurs need people ahead of them, beside them, and behind them
    • Why mentoring other people creates meaning
    • Why humility is one of the keys to lasting success
    • Why saying “I don't know” can make you a stronger leader
    • Why successful entrepreneurs ask for help
    • Why the way someone responds to failure may matter more than the failure itself
    • Larry's “Serve First” philosophy
    • How Joe applied that advice and saw his revenue increase
    • Why service can create both meaning and business value
    • Why challenges and struggles can strengthen entrepreneurs
    • Larry's early entrepreneurial experiences
    • His journey from Green Beret to hotel night auditor to hotel-company partner
    • How leadership and team-building became Larry's competitive advantage
    • How he became a partner without having money or a major professional network
    • Leading a hotel company through COVID
    • What it was like to lay off a significant portion of the workforce
    • Why entrepreneurs need people they can talk problems through with
    • What great mentors do differently
    • Why entrepreneurship involves far more than simply being good at your product or service
    • Why standard operating procedures are critical
    • Why a business loses value when every process lives inside the owner's head
    • How systems allow a company to operate without the owner
    • Why entrepreneurs should expect setbacks
    • Why accounting and legal guidance need to be part of the business from the beginning
    • Why waiting until you're “making money” to build systems can keep you permanently behind
    • How habit stacking can help entrepreneurs improve multiple areas of life at once

    One of Larry's central lessons is:

    Reality is your friend.

    Problems will happen.

    Plans will change.

    You will make mistakes.

    The question is whether you have the humility, systems, support, and tenacity to keep moving forward.

    And perhaps the most important lesson:

    Don't build a successful business at the expense of building a successful life.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)



    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    51 min
  • Before You File: How to Catch Tax Mistakes and Missing Documents

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    Before you file your tax return, stop.

    Have you compared it to last year?

    Do you know which documents you're still waiting for?

    Have you verified that the 1099s, retirement statements, K-1s, and other third-party forms you received are actually correct?

    In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, explains how self-employed professionals can systematize tax season and reduce the anxiety, confusion, and costly mistakes that often come with filing a return.

    Joe's process starts somewhere many taxpayers never think to look:

    Your prior tax returns.

    By reviewing the last two years, you can build a roadmap of the income sources, deductions, schedules, and third-party documents you should expect to see again.

    Then you can identify what's missing before the return gets filed.

    In this episode, Joe discusses:

    • Why tax anxiety is often preventable
    • How to systematize your personal tax-return process
    • Why you should start by reviewing the previous two years of tax returns
    • How to review pages one and two of your Form 1040
    • Understanding income, adjustments, taxable income, taxes, payments, refunds, and balances due
    • Why prior-year returns create a useful checklist for the current year
    • How to identify the supporting documents behind last year's numbers
    • Why 1098s, 1099s, K-1s, brokerage statements, and other forms can delay filing
    • Why some documents may need to be downloaded instead of arriving in the mail
    • Why K-1s and investment statements are often received later
    • Why brokerage statements may sometimes be corrected after they're initially issued
    • Why you should not assume a third-party tax statement is correct simply because you received it
    • How comparing documents to prior years can help uncover discrepancies
    • What happens when your tax return does not match information reported to the IRS
    • Examples of incorrect retirement reporting
    • Why documentation matters for charitable contributions
    • Non-cash charitable contributions and supporting receipts
    • Home-office expenses and recordkeeping considerations
    • Why proper reimbursement procedures matter when a corporation reimburses an owner for business expenses

    One of the most important lessons in this episode:

    Don't treat tax preparation as data entry. Treat it as a review process.

    Your tax return should make sense compared with prior years.

    Your documents should match what actually happened.

    And if something looks wrong, investigate it before filing.

    A tax document can contain an error.

    A form can be delayed.

    A brokerage statement can be revised.

    And if information reported on your return doesn't match information already reported to the IRS, you may eventually have another problem to solve.

    So slow down.

    Compare.

    Verify.

    Document.

    Then file.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)



    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    24 min
  • Avoiding the Pain and Confusion of Tax Season

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    Tax season is here—and for many self-employed professionals, that means confusion, missing documents, questions about deductions, and fear of an unexpected tax bill.

    But tax season doesn't have to become an annual financial emergency.

    In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, explains why better tax outcomes begin long before your tax return is prepared.

    The key?

    Better books, better records, better financial habits, and year-round communication with your accountant.

    In this episode, Joe discusses:

    • Why accurate books and records are the foundation of tax preparation
    • Why good tax habits should happen throughout the year
    • The importance of keeping supporting documentation for business expenses
    • Why business owners need to understand their balance sheet and income statement
    • How better financial information can reduce tax-season surprises
    • Why waiting until tax season may eliminate valuable planning opportunities
    • The difference between using a once-a-year tax preparer and having a more proactive accounting relationship
    • Why self-employed professionals need to know their numbers
    • The value of reviewing your financial results during the year
    • Retirement-plan considerations for self-employed business owners
    • How to begin organizing your tax documents
    • 1099s, 1098s, W-2s and other third-party tax forms
    • Why some tax documents may need to be downloaded instead of arriving in the mail
    • Tax-reporting considerations when you have cryptocurrency activity
    • Marketplace health-insurance forms and premium tax-credit reporting
    • Why missing documents can lead to IRS notices and additional work
    • Why filing an extension gives you additional time to file—but does not automatically extend the time to pay your taxes

    One of the most important lessons is simple:

    Your tax return is the end of the process—not the beginning.

    If you're discovering what happened in your business for the first time when your tax return is being prepared, something is wrong with the system.

    You should know your numbers throughout the year.

    You should know whether your books are accurate.

    You should understand the financial health of your business.

    And you should have an idea of where you stand before tax season begins.

    If you haven't been doing that, don't beat yourself up.

    Start now.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)



    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    23 min
  • Why Most Self-Employed Professionals Are Always Busy… but Still Broke

    Send us Fan Mail

    Feeling overwhelmed in business?

    You’re not alone—and according to Joe DiChiara, CPA and lifelong entrepreneur, overwhelm isn’t something entrepreneurs can completely avoid. The real challenge is learning how to prepare for it, manage it, and keep moving when business gets difficult.

    In this episode of How to Win Big at Business and Taxes, Joe breaks down the financial and mental preparation self-employed professionals need to handle the inevitable ups and downs of entrepreneurship.

    You’ll learn:

    • Why overwhelm is part of the entrepreneurial journey
    • Why accepting that business will be difficult can actually make it easier
    • How to build a realistic personal budget before depending on your business for income
    • Why reviewing bank and credit card statements gives you a more accurate picture of your real expenses
    • Why Joe recommends adding a cushion for unexpected costs
    • How much your business really needs to produce after taxes
    • Why keeping or returning to a job temporarily may sometimes be the smart move
    • Why every business needs a realistic startup and operating budget
    • How seasonality can create serious cash-flow pressure
    • Why new business owners should build personal and business cash reserves
    • How to handle unexpected tax, payroll, sales-tax, and compliance costs
    • Why entrepreneurs should expect problems instead of simply reacting to them
    • Why successful entrepreneurs are ultimately problem solvers
    • What to do when you start questioning whether you should quit
    • Why discipline is more dependable than motivation
    • How positive habits help entrepreneurs manage pressure
    • Why taking time away from your business can actually make you a better decision-maker

    One of the biggest lessons in this episode is simple:

    It’s not whether difficult times will come. It’s how prepared you’ll be when they do.

    There will be expenses you didn’t expect.

    Revenue may slow down.

    Clients may disappear.

    The economy may change.

    You may make mistakes.

    And at some point, you may even wonder whether you should close the business and go back to a job.

    That doesn’t automatically mean you failed.

    It means you’re experiencing entrepreneurship.

    Prepare financially. Build discipline. Develop positive habits. Protect your cash flow. And remember:

    Entrepreneurs solve problems.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)



    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    23 min
  • The Top 5 Mistakes Self-Employed Professionals Make (And How to Avoid Them)

    Send us Fan Mail

    If you're self-employed, working harder isn't always the answer.

    Sometimes the real problem is that the foundation of your business was never built correctly.

    In this episode of **How to Win Big at Business and Taxes**, Joe DiChiara, CPA and lifelong entrepreneur, breaks down some of the biggest mistakes he sees self-employed professionals make—and why these mistakes are often connected.

    Joe discusses why simply hiring an accountant isn't enough. You need advisors who understand business, communicate with you, help you understand your financial information, and give you the guidance you need to make better decisions.

    You'll also discover why successful business owners need to understand their numbers, ask for help, recognize their own strengths and weaknesses, take advantage of legitimate business tax deductions, and make sure their business is structured appropriately.

    In this episode, Joe covers:

    • Why choosing the wrong CPA can hurt your business  
    • What to look for in a business-oriented accountant  
    • Why communication with your CPA matters  
    • Why business owners need current financial information  
    • The importance of understanding your profit and loss statement and balance sheet  
    • Why doing everything yourself can become a major mistake  
    • Why asking for help is a strength—not a weakness  
    • The difference between a mentor and a business coach  
    • Why understanding your strengths can improve your business  
    • How the right people can fill the gaps in your skill set  
    • Why business structure matters  
    • Why an LLC does not automatically create a different federal tax classification  
    • Why self-employed professionals frequently overlook legitimate business deductions  
    • How your car, phone, computer, and home office may have business-use components  
    • Why the right CPA should help educate you—not simply prepare your tax return

    Being self-employed doesn't mean you have to figure everything out alone.

    The goal is to build a business that gives you better information, better support, better systems, and better decisions.

    Ask yourself:

    **Which one of these mistakes is holding YOUR business back right now?**

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel  
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)  
    www.Bedrock360TaxSolutions.com (Tax Guard 365)  
    www.Bedrock360BusinessCourses.com (Courses)



    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    21 min
  • Featuring Vincent A. Lanci Expert Podcaster & Podcast Producer

    Send us Fan Mail

    Vincent A. Lanci was 21 years old when he was hit by a car.

    He woke up about a week later from a coma and had to relearn how to walk and talk.

    At one point, doctors weren't sure he would survive the night. Later, Vincent faced the possibility that he might need around-the-clock care or never finish school.

    He refused to allow other people's expectations to define his future.

    In the first-ever guest episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, sits down with his friend, client, mentor, and podcast coach Vincent A. Lanci.

    Vincent shares his remarkable journey from traumatic brain injury to entrepreneurship—and the lessons he learned along the way.

    You'll hear about:

    • Surviving a devastating accident and coma
    • Relearning how to walk and talk
    • Overcoming other people's expectations
    • Earning an MBA and later working as a busboy and waiter
    • Swallowing your ego while building a business
    • The sacrifices required in the early stages of entrepreneurship
    • Building a podcast from scratch
    • Starting with the resources you already have
    • Knowing when it's time to outsource
    • Turning podcasting into a revenue-producing business
    • Why entrepreneurs need mentors, coaches, and outside help
    • How Vincent landed Tampa General Hospital as a client
    • Why your existing network may be your best source of business
    • What happens when revenue suddenly slows down
    • Planning for seasonal business cycles
    • The emotional toll of entrepreneurship
    • A $7,000 chargeback that ended up in court
    • Why successful entrepreneurs still experience bad days
    • Why tenacity is essential to long-term success
    • How to keep going when everything seems to be going wrong

    Vincent's journey perfectly represents what this podcast is about.

    Entrepreneurship isn't a straight line.

    There are peaks and valleys.

    There are successes and failures.

    There are times when everything seems to be working—and times when you wonder whether you should quit.

    The difference is what you do next.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)



    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    34 min
  • Start Small, Start Smart: The Micro-Course Formula for New Entrepreneurs

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    What if the knowledge you already have could become your next revenue stream—or even your next business?

    In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, explains why course creation can be one of the fastest and least expensive ways to turn your knowledge and experience into something valuable.

    Joe talks about why perfectionism stops so many people from ever launching, why you do not need to be highly technical, and why expensive equipment is not necessary to get started.

    You’ll learn:

    • Why there is no such thing as a “perfect” course
    • How to turn your expertise into a business opportunity
    • Why a course can also work as a lead magnet
    • Why students care more about value than perfection
    • What basic equipment you really need
    • Why you can start with tools you may already own
    • How platforms like Zoom, Loom, Google Slides, Thinkific, Teachable, Kajabi, Kartra, and GoHighLevel can help
    • Why shorter lessons are often more effective
    • Why your first course should be a focused micro-course
    • How to test your course from the student’s perspective
    • Why feedback and continuous improvement matter

    The biggest takeaway?

    Stop waiting until everything is perfect.

    Start with something you know.

    Solve one specific problem.

    Create something useful.

    Then improve it as you go.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:

    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)



    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    18 min
  • Monetize Your Genius Through Course Creation

    Send us Fan Mail

    Welcome back to Episode #4 of How to Win Big at Business with Joe DiChiara, CPA — and today’s message is a game-changer:

    Creating online courses is the fastest, easiest, and most profitable path to growing—or even starting—a business.

    In this episode, Joe breaks down how anyone can turn their knowledge, skills, or life experience into a revenue-generating online course… even if you think you’re “not tech savvy” or “don’t know enough.”

    You do. And today’s episode proves it.

    What You’ll Learn in Episode 4:
     ✔ Why course creation is the most powerful business model today
     ✔ How everyday skills (like growing tomatoes!) can turn into full-time income
     ✔ Joe’s story of teaching remote accounting long before it was trendy
     ✔ Why hiring “less experienced” people can be a smarter business move
     ✔ The decade-long struggle Joe had with perfectionism—and what finally broke it
     ✔ How AI changed everything in September 2024
     ✔ The exact moment Joe realized he could automate course creation using AI agents
     ✔ The birth of the “Monetize Your Genius” workshop
     ✔ Why teaching others is not just profitable—it’s profoundly fulfilling

    Whether you're a business owner wanting to scale, an expert ready to be recognized, or someone who simply wants to monetize what you already know… this episode is your wake-up call.

    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    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

    Because running a business shouldn’t feel like wrestling an octopus… alone.

    Also check out:
    www.Bedrock360BusinessSolutions.com (Complete Coverage)
    www.Bedrock360TaxSolutions.com (Tax Guard 365)
    www.Bedrock360BusinessCourses.com (Courses)


    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, and structures needed to move from solopreneur to sustainable business owner.

    Subscribe to our YouTube Channel
    https://www.youtube.com/@Bedrock360BusinessSolutions/featured
    Thanks for listening!

    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 Guard 365) 

    www.Bedrock360BusinessCourses.com (Courses)

    17 min

About How to Win BIG at Business and Taxes

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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…