Small Business Tax Savings Podcast

Are you an S Corp owner paying for your home office, mileage, phone, or other business expenses out of your own pocket?

You could be missing valuable tax deductions.

In this episode, Mike Jesowshek, CPA, explains how an accountable plan allows your business to reimburse you for qualifying expenses tax-free while claiming the appropriate business deductions.

👉Find out how much your business could save in taxes:

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

[00:00] Why S Corp Owners Need an Accountable Plan

Learn how an accountable plan allows your business to reimburse you tax-free for qualifying expenses you've paid personally, rather than missing deductions or treating reimbursements as taxable wages.

[05:00] Who Needs an Accountable Plan and Who Doesn't?

Understand why accountable plans are especially important for S Corp and C Corp owners, and how the rules differ for sole proprietors, single-member LLCs, and partnerships.

[07:00] How to Set Up an Accountable Plan in 3 Steps

Learn how to create a reimbursement policy, document expenses with receipts and reports, and transfer reimbursements correctly from your business to your personal account.

[10:00] IRS Requirements and Which Expenses Qualify

Understand the documentation and timing rules for tax-free reimbursements, plus how to claim qualifying home office expenses, business mileage, phone bills, internet, meals, and travel.

[15:00] How $12,500 in Reimbursements Could Save Thousands in Taxes

See a practical S Corp example combining home office, mileage, phone, and other expenses to generate $12,500 in business deductions and potentially $3,500 to $4,500 in tax savings.

[18:00] Common Accountable Plan Mistakes That Could Cost You Deductions

Avoid unsupported reimbursements, flat monthly allowances, claiming personal expenses as business expenses, incorrect bookkeeping, and other mistakes that could trigger taxable wages or denied deductions.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Can you deduct your home office if you rent? When does switching to an S Corp make sense? And what happens if you've made a mistake with your retirement contributions?

In this listener Q&A episode, Mike Jesowshek, CPA, answers common tax questions from small business owners and explains how to approach deductions, business structures, payroll, and retirement planning.

👉Find out how much your business could save in taxes:

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

01:00 Home Office Deductions & the Augusta Rule
Learn when home office spaces qualify for deductions, how renters can benefit, and how to document business meetings held at home.

07:00 Starting a Business, LLCs & S Corp Elections
Explore business funding options, when electing S Corp status makes sense, and why separating business finances matters.

13:00 S Corp Payroll & Reasonable Salary Requirements
Learn how to handle delayed payroll, catch-up payments, and reasonable compensation requirements for S Corp owners.

16:00 Hiring Your Kids Through Your Business
Understand payroll taxes when employing your children and how different business structures affect your tax savings.

19:00 Retirement Contributions & Estimated Tax Payments
Learn how to correct excess Roth IRA contributions, compare Solo 401(k)s and SEP IRAs, and avoid estimated tax penalties.

24:00  Vehicle Expenses, Accountable Plans & Travel Deductions
Compare mileage versus actual expenses, learn how S Corp reimbursements work, and understand deductions for business trips involving family.

28:30 Final Takeaway: Implementing Tax Strategies Correctly
Discover why proper documentation, timing, and implementation are essential to protecting your deductions and avoiding costly tax mistakes.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

The money you're already spending on your family could help lower your business tax bill

If your family members perform legitimate work for your business, you may be able to turn some of that spending into tax-deductible wages.

In this episode, Mike Jesowshek, CPA, explains how hiring your kids and other family members can help reduce your taxes in 2026. He covers who you can hire, how the rules differ for sole proprietors and S corp owners, and how much your children can potentially earn tax-free. He also walks through reasonable wages, payroll requirements, the documentation you need, and common mistakes that could put your deductions at risk.

👉Find out how much your business could save in taxes:

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

00:00 How Hiring Your Family Can Help You Save on Taxes 

Mike explains how paying family members for real work can turn everyday family support into business deductions. He also shares how one business owner saved $12,000 by hiring his kids.

04:00 How the Tax Savings Work

How hiring family members can lower your taxes, including the 2026 standard deduction of $16,100 and potential payroll tax savings.

07:00 Who Can You Hire? Kids, Spouses, and Other Relatives

 The rules for hiring children, spouses, parents, and other relatives, and when each option makes financial sense.

13:00 The S Corp Workaround and Family Management Companies

 Why S corp owners face different payroll tax rules and how a separate business may help them qualify for additional savings.

17:00 Setting Up Payroll and Documentation Correctly 

How to choose appropriate work, pay reasonable wages, and keep the paperwork needed to support your deductions.

22:00 Reporting Family Wages and Calculating Your Tax Savings 

How to report wages correctly, handle payroll taxes, and calculate potential savings using real client examples.

26:00 Using a Roth IRA to Build Tax-Free Retirement Savings 

How children with earned income can contribute to a Roth IRA and start building retirement savings early.

29:00 Common Mistakes to Avoid and Key Takeaways 

The biggest mistakes to avoid, including missing records, unreasonable wages, incorrect payroll reporting, and paying for personal chores.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Stop paying your medical bills with after-tax dollars 

You’re already paying for deductibles, prescriptions and co-pays. With the right setup, your business could pay you back for them, tax-free.

In this episode, Mike Jesowshek, CPA, explains how a medical expense reimbursement plan (also called an owner HRA or Section 105 plan) can turn out-of-pocket medical costs into business deductions. He covers who qualifies, which entity types work for single and married owners, and the workaround for S corp owners. He also walks through the paperwork you need, how to report the plan on your tax return, and the common mistakes that can cost you the deduction.

👉Find out how much your business could save in taxes:

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

00:00 Why Your Medical Costs Aren’t Fully Deductible
Mike explains who this strategy is for (owners with no employees outside the family) and why high out-of-pocket medical costs often get little or no deduction as itemized deductions, even in a costly year.

03:00 What a Section 105 Plan Is and Who Qualifies
How a medical expense reimbursement plan lets your business reimburse an employee for qualified family medical costs, turning after-tax spending into pre-tax business deductions. It also covers the no-employee requirement and how other businesses you own could affect whether you qualify.

06:00 Entity Type, Marital Status, and the S Corp Workaround
Why single owners need a C corp and married owners can hire their spouse through a sole proprietorship, partnership, C corp, or rental property. Mike also explains why the plan doesn’t work in an S corp and how moving part of your income into a separate entity can get around that.

09:00 Setting Up the Plan and Reimbursing Expenses
The paperwork you need, including a written plan document, employment agreement, job description, and time log. Mike also covers which expenses qualify under IRS Publication 502 and how receipts, a reimbursement log, and payments from the business account support each claim.

13:00 Reporting the Deduction on Your Tax Return
Where the deduction goes on a Schedule C, partnership return, C corp return, or Schedule E rental, why these costs no longer belong on Schedule A, and the Form 720 filing that goes with the plan.

16:00 Is It Worth It? A Real Number Example
How $50,000 in qualified medical expenses could create more than $17,000 in tax savings. Mike also explains why the plan usually isn’t worth it under $5,000 in costs and when it starts to make sense.

18:00 Mistakes to Avoid and Key Takeaways
The most common mistakes, including missing paperwork, a spouse who doesn’t do real work, outside employees, using an S corp, and improper reimbursements. Mike closes with why getting the structure right matters, especially for families with ongoing medical costs.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Your health insurance could do more than cover medical emergencies. With the right strategy, it could also help you save on taxes. 

In this episode, Mike Jesowshek, CPA, breaks down health insurance options for small business owners, from group plans to employee reimbursements and stipends. He explains the steps S corp owners need to take to deduct their health insurance premiums and how eligible business owners can use an HSA for tax savings and long-term growth.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

00:00 | Health Insurance as a Tax Strategy
How healthcare planning can help business owners protect themselves, offer employee benefits, and save on taxes.

01:00 | Your Health Insurance Options
An overview of group plans, self-funded plans, HRAs, and stipends, plus how your needs differ when you’re self-employed.

03:00 | The HSA’s Triple Tax Advantage
A look at tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses.

04:00 | Group Health Insurance Plans
How group plans work and how employers decide what portion of employee premiums to cover.

05:00 | Self-Funded and Level-Funded Plans
How these plans differ from traditional group insurance, including potential savings and risks.

07:00 | Health Reimbursement Arrangements
How HRAs let employers reimburse eligible healthcare costs and why employees need to document their expenses.

08:00 | Stipends and Offering No Coverage
The tax tradeoffs of paying employees extra for healthcare and how benefits can help attract and retain talent.

11:00 | Health Insurance for S Corp Owners
The payment, W-2 reporting, and personal tax return steps discussed for claiming the health insurance deduction.

15:00 | HSA Eligibility and Contribution Limits
An explanation of qualifying health plans and the contribution limits covered in the episode.

17:00 | Investing Your HSA and Saving Receipts
Why leaving funds invested may support long-term growth, and how saved medical receipts can support later reimbursements.

19:00 | Review Your Healthcare Strategy Each Year
Bring coverage, deductions, employee benefits, and HSA planning together as your business grows.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Documentation 101: How to Prepare for an IRS Audit 

You claimed the deduction. But if the IRS asks, can you prove it?

Mike Jesowshek, CPA, explains which records you need to support your business expenses. Learn how to document purchases, keep clean books, and organize your receipts so you’re prepared if the IRS comes knocking.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

Chapters: 

00:00 Your Tax Deductions Need Documentation
Paying with a business card doesn’t automatically make a purchase deductible. You need records showing what you bought and why it was business related.

03:00 Audit Selection vs. Audit Outcome
Even well-organized businesses can get audited. Good documentation helps you support your deductions if you’re selected.

08:00 The Proof Behind a Business Deduction
Every deduction needs an actual transaction, a business purpose, and the correct tax treatment. Your supporting records should match.

12:00 Clean Books and Separate Bank Accounts
Separate business and personal accounts, update your books regularly, and clearly label expenses, transfers, and owner activity.

14:00 Business Structure, Payroll, and Reimbursements
Your tax filings and records should match your business structure. Payroll, accountable plans, and meeting records need proper implementation.

17:00 What to Record Beyond the Receipt
Document the business purpose and who was involved. Supporting invoices, calendar entries, and emails can help explain the expense.

19:00 Supporting Records for Mileage, Travel, and More
Mileage, travel, equipment, contractors, loans, and reimbursements each need records that support the transaction.

20:00 Building an Audit-Ready Workflow
Capture receipts promptly, add context, categorize expenses consistently, and save your documents digitally.

22:00 Testing Whether You Can Find Your Records
Choose an older transaction or five large expenses. Check whether you can quickly find the records supporting them.

23:00 What to Do When an Audit Letter Arrives
Read the request carefully, meet deadlines, organize your response, and speak with a qualified tax professional.

25:00 How Good Documentation Pays Off
Organized records make audit responses faster and deductions easier to defend. Clean books also help you make business decisions.

27:00 Why Tax Strategies Need a Paper Trail
Putting a strategy into practice includes documenting it. Hiring your kids, for example, requires records of their work and payments.

28:00 Key Takeaways and Next Steps
Clean books and timely documentation help you prepare for an audit. Learn where to find support implementing tax strategies.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Are you missing out on the home office deduction because you think your workspace doesn’t qualify?

In this episode, Mike Jesowshek explains who qualifies for the home office deduction and how to calculate it using either the simplified or actual expense method. He also breaks down the regular and exclusive use rules, how the deduction differs for sole proprietors and S Corporation owners, and why a qualifying home office could unlock additional business mileage deductions.

You’ll learn how to choose the right calculation method, document your workspace, avoid common mistakes, and turn expenses you’re already paying into a legitimate business tax deduction.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

00:00 How the Home Office Deduction Works
The home office deduction allows business owners to turn a portion of expenses they’re already paying, including rent, utilities, insurance, and homeownership costs, into legitimate business deductions.

02:20 Who Qualifies for a Home Office Deduction?
A qualifying workspace must be used regularly and exclusively for business. It doesn’t need to be an entire room, but the separation between business and personal use must be clear.

04:15 What Counts as Your Principal Place of Business?
Your home doesn’t need to be the only place where you work. A home office may qualify if you regularly use it for administrative or management activities such as bookkeeping, scheduling, invoicing, planning, and customer follow-ups.

06:30 The Simplified Home Office Deduction
The simplified method provides a deduction of $5 per qualifying square foot, up to 300 square feet. It requires less recordkeeping but limits the maximum annual deduction to $1,500.

08:50 How the Actual Expense Method Works
The actual method calculates your deduction using the percentage of your home used for business. It may include a portion of rent, mortgage interest, property taxes, utilities, insurance, repairs, cleaning, and depreciation.

10:50 Simplified vs. Actual Expenses
The simplified method may be easier, but the actual method can produce a significantly larger deduction. Business owners should calculate both methods each year before deciding which one to use.

11:35 How to Claim the Deduction Based on Your Business Structure
Sole proprietors and single-member LLCs generally claim the deduction through Schedule C and Form 8829. S Corporation owners typically need an accountable plan to reimburse themselves properly for home office expenses.

13:40 How a Home Office Can Unlock Business Mileage
A qualifying home office may establish the starting point of your business day. This can allow trips from your home office to clients, suppliers, job sites, or other business locations to qualify as deductible business mileage rather than commuting.

15:30 Common Home Office Deduction Mistakes
Personal use of the workspace, estimated measurements, missing housing records, and incorrect treatment based on business structure can weaken or eliminate the deduction.

16:30 Your Home Office Deduction Checklist
Photograph and measure your workspace, confirm your home’s total square footage, collect your annual housing expenses, compare both calculation methods, and document how the deduction will be handled based on your entity type.

17:50 Equipment and Other Home Office Deductions
Computers, desks, cameras, microphones, and other business equipment should generally be analyzed separately. The home office calculation focuses on the cost of the qualifying physical space rather than the equipment used to operate the business.

18:25 How to Make Your Home Office Deduction Defensible
The goal isn’t to claim your entire home as a business expense. It’s to identify the portion legitimately used for business, document it properly, choose the best calculation method, and revisit the deduction each year.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Are you missing out on a business vehicle deduction, or claiming more than you’re actually allowed?

In this episode, Mike Jesowshek explains how business vehicle deductions work, including the difference between the standard mileage and actual expense methods. He also breaks down the 6,000-pound vehicle rule, business versus personal mileage, vehicle ownership, and the records you need to protect your deduction.

You’ll learn how to choose the right deduction method, avoid costly mistakes, and turn legitimate business driving into a defensible tax strategy.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

00:00 How Business Vehicle Tax Deductions Work
Vehicle deductions should begin with a legitimate business purpose, not the type of vehicle you want to purchase. Business use determines the deduction, regardless of whose name is on the title or whether the vehicle displays your company logo.

02:29 Standard Mileage vs. Actual Expenses
The standard mileage method provides a set deduction for each documented business mile. The actual expense method deducts the business-use portion of costs such as fuel, insurance, repairs, lease payments, interest, and depreciation.

05:20 How to Choose the Right Deduction Method
Compare your expected mileage, business-use percentage, purchase price, operating costs, and potential deductions over several years.

06:55 The 6,000-Pound Vehicle Tax Strategy
Vehicles with a gross vehicle weight rating above 6,000 pounds may qualify for different depreciation treatment. But the available deduction still depends on business use, vehicle classification, taxable income, and the depreciation method used.

09:45 Should the Vehicle Be in Your Personal or Business Name?
A vehicle doesn’t always need to be titled in the company’s name to qualify for a deduction. Personally owned vehicles may be reimbursed for business use, while personal use of a company-owned vehicle may need to be treated as a taxable fringe benefit.

12:30 What Counts as Business Mileage?
Driving between your home and regular office is generally considered commuting. Trips between business locations, client meetings, job sites, suppliers, and other qualifying destinations may count as deductible business mileage.

15:15 The Records You Need to Protect Your Deduction
Business owners should track the date, destination, purpose, and mileage of every business trip. Mileage records are necessary even when using the actual expense method because they support the vehicle’s business-use percentage.

19:00 How to Claim the Vehicle Deduction
Sole proprietors and single-member LLCs generally claim vehicle expenses on Schedule C. S Corporation owners may deduct a company-owned vehicle’s expenses through the business or use an accountable plan to reimburse business use of a personally owned vehicle.

20:20 Business Vehicle Deduction Checklist
Establish the vehicle’s business purpose, estimate business and personal mileage, compare both deduction methods, check the vehicle’s weight rating, and consider whether buying or leasing makes more sense.

22:00 Avoid This Expensive Vehicle Tax Mistake
A deductible vehicle isn’t free. Before purchasing an expensive truck or SUV for the write-off, calculate the actual tax savings and make sure the vehicle is something the business genuinely needs.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Is growing your business creating more stress instead of more freedom? 

In this episode, Mike Jesowshek breaks down what commonly starts to fail as a business reaches $250,000, $500,000, and $1 million in revenue. He explains why your personal capacity, internal systems, financial visibility, and ability to delegate must evolve as the business grows.

You’ll learn how to stop becoming the bottleneck, protect profitability, build a team you can trust, and create the systems and proactive tax plan needed to scale without burning out.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

Chapters:

(03:00) Building Systems at $250,000 in Revenue
Informal processes and information stored in the owner’s head stop working as the business expands. Mike explains how simple checklists and screen recordings can create more consistent results without constant supervision.

(07:00) Delegation Becomes Essential at $500,000
Hiring someone doesn’t automatically reduce the owner’s workload. Effective delegation requires clear outcomes, deadlines, decision-making authority, performance measures, and trust in the people you hire.

(10:15) Making Tax Planning Proactive
As profit increases, reactive tax planning becomes more expensive. Mike covers estimated payments, entity structure, reasonable compensation, retirement opportunities, documentation, and other areas growing businesses should review throughout the year.

(13:00) When the Owner Becomes the Bottleneck
At around $1 million in revenue, the business may have employees and systems but still depend on the owner for every major decision. Mike shares the warning signs that the company cannot operate without your constant involvement.

(14:25) Building Leaders, Not Just Hiring Helpers
Every major function of the business needs clear ownership, measurable goals, and appropriate decision-making authority. Developing capable leaders allows the owner to step away from daily operations and focus on direction.

(18:20) How the Owner’s Role Must Change
The habits that help start a business can become liabilities as it grows. Moving to the next stage requires the owner to spend less time completing tasks and more time planning, coaching, reviewing numbers, and developing people.

(19:45) Mike’s Experience Scaling His Accounting Firm
Mike shares how keeping every process in his head and remaining involved in every client created problems as his firm grew. He explains how those lessons shaped the way he approached building his next company.

(22:25) What Kind of Business Do You Actually Want?
Not every owner wants to build a $100 million company. Mike closes by encouraging business owners to define the business and lifestyle they want, then build the systems, team, financial structure, and tax plan required to support it.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

🚀 Visit:  https://www.TaxSavingsPodcast.com 

🚀 Check Out TaxElm: https://taxelm.com/

🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/

🚀 YouTube: www.TaxSavingsTV.com

👋🏼 GET IN TOUCH
You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏

🙌LEAVE A REVIEW
If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐

Is growing your business creating more stress instead of more freedom? 

In this episode, Mike Jesowshek breaks down what commonly starts to fail as a business reaches $250,000, $500,000, and $1 million in revenue. He explains why your personal capacity, internal systems, financial visibility, and ability to delegate must evolve as the business grows.

You’ll learn how to stop becoming the bottleneck, protect profitability, build a team you can trust, and create the systems and proactive tax plan needed to scale without burning out.

👉Find out how much your business could save in taxes.

TaxSavingsPodcast.com/scorecard 

🚀 Book your free demo call today. Click here or visit:

https://taxelm.com/demo/

Chapters:

(03:00) Building Systems at $250,000 in Revenue
Informal processes and information stored in the owner’s head stop working as the business expands. Mike explains how simple checklists and screen recordings can create more consistent results without constant supervision.

(07:00) Delegation Becomes Essential at $500,000
Hiring someone doesn’t automatically reduce the owner’s workload. Effective delegation requires clear outcomes, deadlines, decision-making authority, performance measures, and trust in the people you hire.

(10:15) Making Tax Planning Proactive
As profit increases, reactive tax planning becomes more expensive. Mike covers estimated payments, entity structure, reasonable compensation, retirement opportunities, documentation, and other areas growing businesses should review throughout the year.

(13:00) When the Owner Becomes the Bottleneck
At around $1 million in revenue, the business may have employees and systems but still depend on the owner for every major decision. Mike shares the warning signs that the company cannot operate without your constant involvement.

(14:25) Building Leaders, Not Just Hiring Helpers
Every major function of the business needs clear ownership, measurable goals, and appropriate decision-making authority. Developing capable leaders allows the owner to step away from daily operations and focus on direction.

(18:20) How the Owner’s Role Must Change
The habits that help start a business can become liabilities as it grows. Moving to the next stage requires the owner to spend less time completing tasks and more time planning, coaching, reviewing numbers, and developing people.

(19:45) Mike’s Experience Scaling His Accounting Firm
Mike shares how keeping every process in his head and remaining involved in every client created problems as his firm grew. He explains how those lessons shaped the way he approached building his next company.

(22:25) What Kind of Business Do You Actually Want?
Not every owner wants to build a $100 million company. Mike closes by encouraging business owners to define the business and lifestyle they want, then build the systems, team, financial structure, and tax plan required to support it.

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
Join TaxElm: https://taxelm.com

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