How to Win BIG at Business and Taxes

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What do you do when life changes in an instant?

In this powerful episode of How to Win Big at Business, Joe DiChiara sits down with Vincent Lanci — author, podcaster, coach, entrepreneur, and traumatic brain injury survivor — to talk about recovery, resilience, purpose, and rebuilding a life after everything changes.

Vincent shares the story of being hit by a car at age 21, waking up from a coma after a traumatic brain injury, and slowly rebuilding the basic skills most people take for granted. What followed was not just a recovery story — it was an entrepreneurial journey filled with setbacks, reinvention, service, and impact.

This conversation goes far beyond business. It’s about mindset, persistence, faith, healing, and what it means to keep moving forward one step at a time when the future feels uncertain.

In this episode, you’ll hear:

•  Vincent’s story of surviving a traumatic brain injury 
•  What recovery looked like in the earliest days 
•  The emotional toll on families and caregivers 
•  Why communication is so critical after a brain injury 
•  How Vincent rebuilt his skills and confidence over time 
•  The parallels between recovery and the entrepreneurial journey 
•  How he turned his experience into coaching, books, podcasting, and service 
•  Why your story can become your mission 
•  How podcasting became part of his business and impact strategy 

This episode is deeply inspiring for anyone who has ever faced a major setback, questioned whether they could keep going, or wondered if something meaningful could still come from a painful chapter.

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)

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What gets measured can get improved.

But what doesn't get measured is extremely difficult to manage.

Too many self-employed professionals run their businesses by looking at two numbers:

Sales and the balance in the bank account.

Both can be dangerously misleading.

In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, explains the key performance indicators business owners should monitor if they want to make better decisions, spot problems earlier, and build a more predictable business.

This episode builds on Joe's discussion of Virtual CFO services by focusing on the actual numbers business owners need to understand.

Joe discusses:

• Why your bank balance doesn't tell you the full financial story
• Why successful business owners know their numbers
• How financial visibility improves decision-making
• Why revenue needs to be tracked consistently
• How seasonality and trends affect business performance
• Why lead flow should be monitored
• The relationship between prospecting and future revenue
• Why businesses need consistent lead-generation systems
• Why conversion rate matters
• How multiple sales funnels can support a business
• Why cash reserves are critical
• How reserves reduce stress when business inevitably gets difficult
• How to monitor the value of your sales pipeline
• Why converting someone into even a small paying customer can change the relationship
• How prospects move through a sales funnel
• How pipeline metrics can help predict future revenue
• Why customer concentration creates risk
• Joe's experience relying too heavily on large clients
• Why having many smaller clients can sometimes reduce business risk
• Capacity and utilization
• How to know when it's time to hire or delegate
• Why sitting idle means capacity isn't being used effectively
• Why KPI dashboards can provide early warning signals
• How business problems often develop gradually even when they appear suddenly

Joe identifies seven important areas every self-employed professional should consider monitoring:

1. Revenue

What are you producing and which direction is it moving?

2. Lead Flow

How many qualified prospects are entering your business?

3. Conversion Rate

How effectively are you turning prospects into paying customers?

4. Cash Reserves

How long could the business survive if revenue slowed dramatically?

5. Pipeline Value

How much potential future business is currently moving through your sales process?

6. Client Concentration

How much damage would losing your largest customer cause?

7. Capacity & Utilization

Can you handle additional business—or has the time come to hire, delegate, or improve your systems?

Joe also shares an example where more than 2,000 people registered for a workshop but almost nobody attended.

The leads weren't the problem.

The funnel was.

A breakdown in email delivery meant people registered but never received the communications needed to get them to the event.

That's why simply measuring one number isn't enough.

You need to understand how the numbers relate to each other.

Revenue.

Leads.

Conversions.

Cash.

Pipeline.

Clients.

Capacity.

Together, they begin telling the story of your business.

And a good dashboard can help you recognize trouble before it turns into a crisis.

Think of it as your business weather forecast.

You may not be able to prevent every storm.

But you can prepare for it.

Know your numbers.

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)

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Business owners don't simply want to know what happened last month.

They want to know:

Where is my cash going?

Why are sales increasing but profits aren't?

Can I afford another employee?

Can I buy new equipment?

How much cash should I keep in reserve?

Which products or services are actually making me money?

Those are the questions a good CFO helps answer.

In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, explains the difference between traditional accounting and Virtual CFO services—and why small business owners increasingly need both.

Accounting is essential.

The books need to be accurate.

Accounts need to be reconciled.

Transactions need to be classified correctly.

Revenue and expenses need to be completely recorded.

But accounting primarily tells you what already happened.

A CFO takes that information and helps answer another question:

What should we do next?

Joe discusses:

• Why business owners increasingly want guidance instead of just historical financial reports
• What a Virtual or Fractional CFO does
• Why small businesses can now access CFO-level services without hiring a full-time executive
• How technology and AI are changing financial advisory services
• The difference between an accountant and a CFO
• Why accountants primarily focus on historical information and accuracy
• Why CFOs focus on planning, budgeting, forecasting, analytics, and decision-making
• Why projected cash flow is so important
• How a profitable business can still experience negative cash flow
• Why positive cash flow does not automatically mean the business is profitable
• How CFO guidance can improve profitability and financial confidence
• Why good financial information can reduce the uncertainty business owners feel
• Why accurate bookkeeping remains the foundation of financial analysis
• How platform fees and gross sales can distort financial statements when they're recorded incorrectly
• Why business owners care more about decisions than accounting mechanics
• Whether increasing sales are actually producing increasing profits
• Whether a business can afford equipment or additional employees
• How much cash a business should maintain
• How to determine which products and services are most profitable
• Why analytics should drive business decisions
• KPIs, ratios, budgets, and cash-flow projections
• Monthly and quarterly Virtual CFO deliverables
• How Joe uses analytics in his own course business to determine what customers actually want
• Why AI does not eliminate the need for human financial judgment
• How AI can make accountants and CFOs more efficient
• Why professionals should use AI to empower their teams rather than simply replace people
• Why Virtual CFO services represent an opportunity for accountants, bookkeepers, and other financial professionals

Joe describes the basic difference this way:

An accountant is largely a historian.

The accountant makes sure the numbers accurately explain what already happened.

A CFO looks toward the future.

What will cash flow look like?

What should the budget be?

What trends are developing?

Where are margins improving or declining?

Should we hire?

Should we invest?

Should we stop offering a product or service?

Can we afford to grow?

A business needs both perspectives.

For business owners, that means financial reports should lead to decisions.

For accountants and bookkeepers, it creates an opportunity to become more valuable by moving beyond data entry and historical reporting into analysis, communication, planning, and advisory services.

The future of financial services isn't simply producing more numbers.

It's helping business owners understand what those numbers mean and what they should 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)

Send us Fan Mail

In this episode of How to Win Big at Business, Joe DiChiara sits down with entrepreneur and technology expert Jerry Goddard to talk about a problem almost every self-employed professional is facing right now: AI overwhelm.

If you feel buried by too many AI tools, too many subscriptions, and too much hype, this conversation will help you cut through the noise.

Joe and Jerry break down what makes Google NotebookLM different from tools like ChatGPT, Gemini, and Claude. Instead of pulling information from the entire internet, NotebookLM lets you work from the specific sources you choose. That makes it a practical tool for business owners who want better research, better organization, stronger training systems, and fewer bad AI answers.

In this episode, they discuss:

• why business owners should master one AI platform instead of chasing every new tool
• how NotebookLM can help with SOPs, onboarding, and internal training
• why AI should be treated like a gifted intern
• how to think about hallucinations and verification
• why cybersecurity matters even more for small business owners today

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)

Send us Fan Mail

In this episode of How to Win Big at Business, Joe talks with Marianne “Coach Yanyan” Labonete about the real path from corporate work to entrepreneurship, freelancing, coaching, and business freedom. Marianne shares how she navigated career changes, income pressure during the pandemic, online work, bookkeeping, client acquisition, and eventually built a powerful personal brand and community that opened major doors for her business. 

This conversation is full of lessons for self-employed professionals who want to attract clients, grow their authority, and build a business around their true strengths instead of staying trapped in work that drains them. Marianne explains why authenticity matters, how trust drives sales, why consistency on LinkedIn works, and how mentors, community, and trial-and-error helped shape her path. 

Joe and Marianne also talk about:

•  the pain of career transition 
•  the realities of freelancing and entrepreneurship 
•  how to use social media to build visibility 
•  why personal branding creates opportunities 
•  the importance of mentors and coaches 
•  finding your “why” and your real superpower 
•  building freedom through service and alignment 

This is a powerful episode for anyone who wants more than income—they want freedom, purpose, and a business they truly enjoy building. 

Suggested Show Notes Bullets

•  Marianne’s journey from corporate finance to entrepreneurship 
•  What the pandemic taught her about adaptability 
•  How she got started in freelancing and online work 
•  Why trust and authenticity matter in sales 
•  How she built visibility through LinkedIn content 
•  The role of community, mentors, and coaching in growth 
•  Why entrepreneurs need to find their strengths 
•  How personal branding leads to clients and opportunities 
•  What freedom really means as a business owner 

Buzzsprout Hashtags

#Entrepreneurship #PersonalBranding #LinkedInMarketing #BusinessGrowth #Freelancing #SelfEmployed #ClientAttraction #OnlineBusiness #Coaching #WorkFromHome

Subscribe to the Podcast

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)

Send us Fan Mail

In this episode of How to Win Big at Business, Joe talks with Marjorie “Marge” Aviso, co-owner of a successful BPO in the Philippines, about the real challenges behind entrepreneurial success. 

Marge shares her journey from being a nurse and young mother to building a company with 1,600 employees, while navigating painful setbacks, financial mistakes, debt, and the hard decisions that come with leadership. She opens up about what happened when unclear bookkeeping and poor financial visibility left her business exposed, and how she fought back by learning her numbers, restructuring operations, accelerating collections, cutting unnecessary costs, and rebuilding with stronger systems. 

This episode is packed with lessons for self-employed professionals and business owners who want to strengthen their cash flow, understand their financials, lead through adversity, and build a business that creates both income and freedom. It also highlights the power of resilience, values-driven leadership, and the loyalty that comes from building the right team culture. 

Subscribe to the Podcast

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.Bedrock360BusinessTraining.com (Courses)

 #Entrepreneurship #BusinessGrowth #CashFlow #Leadership #SelfEmployed #SmallBusiness #FounderJourney #FinancialClarity #RemoteTeams #Outsourcing 

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)

Send us Fan Mail

Are you worried that artificial intelligence is going to take your job, replace your profession, or hurt your business?

Joe DiChiara has heard this story before.

When personal computers entered the workplace, professionals worried they would eliminate jobs.

When QuickBooks arrived, accountants worried business owners would no longer need them.

And now AI is creating the same fear.

In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, explains why he believes AI represents an enormous opportunity for professionals willing to learn how to use it.

Joe looks back at more than 40 years in accounting and entrepreneurship and explains how previous technological disruptions changed industries—but also created entirely new opportunities.

When QuickBooks first became popular, many accountants resisted it.

Joe did the opposite.

He learned it.

He advertised QuickBooks setup and training.

Customers called because their existing accountants couldn't help them.

And some of those customers eventually became Joe's accounting and tax clients.

Today, Joe is applying the same mindset to AI.

In this episode, Joe discusses:

• Why fear of AI resembles earlier fears about computers and software
• What happened when personal computers entered the accounting profession
• How technology can create new jobs and business opportunities
• Why QuickBooks scared many accountants
• How Joe turned QuickBooks disruption into new revenue
• Why business opportunities often appear when technology changes faster than people can adapt
• Why Joe encouraged his employees to learn AI instead of replacing them
• How AI has dramatically reduced the time needed to create marketing campaigns
• How technology can increase a team's productivity and capacity
• Why AI can help businesses serve more clients
• Why AI-generated information still requires human review
• The problem of AI hallucinations
• Why Joe cross-checks AI-generated tax research
• Why clients will continue to value human communication and judgment
• Why accountants should learn AI now
• Why coders, designers, marketers, and other professionals should do the same
• How AI knowledge itself can become a service businesses sell
• Why predictions about future jobs should be treated cautiously
• Why focusing on current opportunities is more productive than worrying about worst-case scenarios
• How Joe uses AI to dramatically speed up course creation
• How technology helped create a new revenue stream in his business
• Why AI should be viewed as a tool rather than a replacement for people

Joe's message is straightforward:

AI may change what you do. But that doesn't mean it has to eliminate what you do.

Professionals who learn to use the technology can:

Work faster.

Serve more clients.

Create new products.

Launch new services.

Automate repetitive tasks.

And spend more time on the human work that technology cannot easily replace.

The real danger may not be AI itself.

The danger may be ignoring it while your competitors learn how to use it.

Learn the technology.

Experiment with it.

Understand its weaknesses.

Use human judgment.

And look for the opportunities other people are too afraid to see.

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)

Send us Fan Mail

Most self-employed professionals start their business because they are great at what they do.

But running a business requires more than expertise.

It requires structure.

In this episode of How to Win Big at Business, CPA and entrepreneur Joe DiChiara explains one of the biggest mistakes solopreneurs make: relying on large, unpredictable sales instead of building recurring revenue.

Joe shares a real example of a business owner struggling with cash flow despite having a valuable service. The problem wasn’t the offer—it was the financial structure of the business.

You’ll learn how to build a reliable revenue engine using communities, sales funnels, and low-barrier offers that convert leads into long-term clients.

If you’re tired of the feast-or-famine cycle in your business, this episode will show you a smarter path forward.

What You'll Learn in This Episode

• Why great services fail without a revenue structure
• The dangerous “big client” trap many entrepreneurs fall into
• Why recurring revenue is the foundation of a real business
• How to create a community that generates leads every day
• The psychology behind low-cost entry offers
• How to turn leads into high-value clients over time

Key Concept From This Episode

A viable business needs two things:

1. Revenue
2. Positive cash flow

Without both, even great businesses struggle to survive.

Subscribe to the Podcast

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

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)

Send us Fan Mail

Sole proprietor.

LLC.

Partnership.

S corporation.

C corporation.

Which one is right for your business?

More importantly:

Do you know why your business is structured the way it is?

In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, breaks down one of the most important—and most confusing—decisions facing self-employed professionals: choosing a legal and tax structure.

Many people become business owners without realizing it.

You start driving for a gig platform.

You sell products online.

You begin consulting.

You freelance.

You start earning money without receiving a W-2.

And suddenly you're operating a business.

If you haven't deliberately chosen a tax structure, the rules generally provide a default.

Joe discusses:

• When you technically become self-employed
• Why gig workers may already be sole proprietors
• How self-employment tax works
• Why self-employed individuals pay Social Security and Medicare taxes differently from employees
• How even a small side business can create additional tax
• Why business income generally needs to be reported regardless of whether you receive a 1099
• The difference between a business and a hobby
• Why licenses, permits, and local compliance may apply
• What happens when a business owner doesn't make an entity election
• Sole proprietorships
• Partnerships
• Why partnerships should have written agreements
• LLCs and LLPs
• The difference between legal protection and tax classification
• Why a single-member LLC may still be taxed as a sole proprietor
• Why a multi-member LLC may default to partnership taxation
• Why an LLC by itself does not automatically eliminate self-employment tax
• Corporate compliance and recordkeeping
• Schedule C versus separate business tax returns
• Why professional tax and legal guidance matters
• C corporation taxation
• S corporation elections
• How S corporation profits and losses generally flow through to the owner
• Salary and owner distributions
• C corporation double-tax considerations
• Why S corporation taxation is often considered by active business owners
• How an LLC may elect corporate or S corporation tax treatment

One of the biggest misconceptions Joe addresses is this:

An LLC is not automatically a special federal tax classification.

The LLC is created under state law.

The federal tax treatment depends on the number of owners and any tax elections that have been made.

That distinction matters.

Your business structure affects much more than the name on your paperwork.

It can affect:

Your taxes.

Your liability.

Your payroll.

Your bookkeeping.

Your tax-return requirements.

Your compliance obligations.

And how you take money out of the business.

The goal isn't to choose the entity that sounds simplest.

It's to understand the choices and select a structure that fits your actual situation.

If you're already operating a business and you're not sure why you're structured the way you are, it may be time to review it.

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)

Send us Fan Mail

How much should you charge for your services?

It's one of the most difficult questions self-employed professionals face.

Price too low and you risk undervaluing your expertise, attracting highly price-sensitive clients, and creating a business that can't support itself.

Price too high without communicating enough value and potential clients may walk away.

So where is the middle?

In this episode of How to Win Big at Business and Taxes, Joe DiChiara, CPA and lifelong entrepreneur, shares lessons from more than 40 years of entrepreneurship on pricing, value, trust, sales funnels, and growing a service business.

Joe takes listeners back to 1993, when he advertised tax-return preparation for just $35.

The price was intentionally low.

His goal was to get in front of prospective clients, learn about their financial situations, build trust, and create opportunities for other services.

The strategy worked.

His phone rang constantly and he quickly built a client base.

A few years later, after opening his first office and taking on overhead, Joe realized $35 was no longer sustainable.

He raised many of those fees to approximately $200–$250.

He expected to lose clients.

Instead, his clients stayed.

The reason?

Trust.

Joe had already demonstrated his value and built credibility with them.

In this episode, Joe discusses:

• How to think about pricing when you're just starting out
• Why a low introductory price can sometimes make strategic sense
• How a low-cost offer can become the beginning of a sales funnel
• Why pricing must support your larger business objective
• Why trust reduces price sensitivity
• The importance of building know, like, and trust
• Why pricing strategies change as businesses mature
• Why every sales funnel needs a clear target customer
• How an inexpensive entry offer can lead to a higher-value service
• Three basic ways to grow a business
• Adding new valuable services
• Acquiring additional clients
• Raising existing prices
• How to evaluate what the market may be willing to pay
• Why price increases should be connected to increased value or changing costs
• Why transparency matters when explaining higher fees
• Why losing a few clients can sometimes make the business healthier
• How to recognize when you're probably undercharging
• Why poor conversions may indicate a value problem rather than simply a pricing problem

Joe offers one simple pricing test:

If every prospect immediately says yes, you're probably not charging enough.

If nobody says yes, however, don't automatically cut your prices.

Instead, ask:

Do they understand the value?

The goal isn't to find the lowest possible price.

The goal is to create a price that makes sense for:

Your customer.

Your value.

Your market.

Your costs.

And the business you're trying to build.

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)