
Small Business Tax Savings Podcast
by Mike Jesowshek, CPA
Latest Business Ideas
14-Day Home Rental Strategy for Board Meetings
Market Gap: Business meetings can become costly without tax benefits.
The 14-day home rental strategy is a unique approach for small business owners to capitalize on board meetings by renting out their homes tax-free. This idea allows owners to host board meetings at home while converting associated costs into business deductions, such as meals and venue expenses. By adhering to the 14-day rental limit, owners can enjoy tax-free income from the rental, making it a financially advantageous arrangement. The target audience consists of small business owners looking to optimize their meeting expenses and leverage tax strategies to enhance their financial position. This strategy not only provides tax relief but also encourages collaboration with board members.
From: Live Case Study: How We Cut $50K Off His Tax Bill (Step by Step)
Consolidated S Corporation Structure for Multiple Businesses
Market Gap: Multiple S corporations lead to unnecessary costs.
The idea revolves around restructuring multiple businesses under a single S corporation to optimize tax efficiency and reduce operational burdens. By consolidating into one holding S corporation, the owner can manage all business income and expenses through a single entity, which simplifies tax filings and payroll processes. This model is particularly beneficial for business owners managing multiple active businesses, as it limits unnecessary costs associated with maintaining separate corporations. The target audience includes small business owners who are currently managing multiple entities and seeking to minimize their tax obligations.
From: Live Case Study: How We Cut $50K Off His Tax Bill (Step by Step)
HSA Integration with S Corporation for Tax Benefits
Market Gap: Business owners miss tax-saving opportunities with HSAs.
This idea focuses on integrating Health Savings Accounts (HSAs) with S corporation structures to maximize tax benefits for business owners. By contributing to an HSA through the S corporation, owners can avoid FICA taxes on those contributions, providing an additional layer of tax savings. This strategy allows business owners to fund their HSAs while enjoying tax-free growth and withdrawals for qualified medical expenses. The target audience includes small business owners who are eligible for HSAs but are not fully utilizing them due to the complexities involved in setting them up. This approach not only simplifies the process but also enhances overall financial health.
From: Live Case Study: How We Cut $50K Off His Tax Bill (Step by Step)
Mileage Tracking App for Business Owners
Market Gap: Business owners struggle to track mileage for tax deductions.
Develop a mobile app that simplifies the tracking of business mileage for entrepreneurs. The app would allow users to log their trips easily, categorizing them as personal or business with a simple swipe feature. Additionally, it could provide analytics on mileage trends and potential tax savings. By using this app, business owners can ensure they capture every deductible mile, maximizing their tax deductions while minimizing the risk of IRS audits due to poor record-keeping. The target audience would be small business owners and freelancers who frequently use their vehicles for work-related purposes.
From: Car Write-Offs Explained: The 2025 Tax Rules You Need to Know
Automobile Expense Deduction Consulting Service
Market Gap: Many entrepreneurs lack knowledge about effective vehicle tax deductions.
Create a consulting service focused on helping small business owners navigate automobile expense deductions. This service would provide personalized consultations where tax professionals analyze clients' vehicle use and assist them in choosing the best deduction method (mileage vs. actual expenses). The service could also offer a comprehensive package that includes preparation of required documentation, mileage logs, and ongoing support to ensure compliance with IRS regulations. This idea targets small business owners and freelancers who are looking to optimize their tax savings without the headache of navigating complex tax rules on their own.
From: Car Write-Offs Explained: The 2025 Tax Rules You Need to Know
Educational Program on QSBS Strategies
This business idea involves creating an educational program or platform focused on teaching entrepreneurs about QSBS (Qualified Small Business Stock) strategies to maximize tax advantages when selling their businesses. The curriculum would cover the fundamentals of QSBS, eligibility criteria, the importance of timing, and how to effectively use trusts to enhance tax-free capital gains. This educational initiative could be delivered through webinars, workshops, and online courses, targeting startup founders, small business owners, and investors. The program would not only educate participants on the tax benefits but also provide actionable steps to implement these strategies in their business operations. Additional resources such as community forums, one-on-one coaching, and access to tax professionals could enhance the value of the program.
From: Sell Your Company with $0 Taxes? QSBS Explained
QSBS Eligibility Analysis Platform
This idea focuses on building a digital platform that provides startups with a comprehensive analysis of their eligibility for QSBS (Qualified Small Business Stock) and other tax benefits. The platform would automate the evaluation process, allowing founders to input their company financials and structure to receive instant feedback on their QSBS qualification. This tool would not only simplify the eligibility checks but also provide tailored recommendations on structuring businesses (like switching from LLC to C Corp) to maximize tax advantages. The target audience includes startup founders and early-stage investors looking to understand their tax benefits better. The platform could leverage algorithms to analyze financial data and provide insights, further enhancing the experience with educational content about QSBS and tax strategies.
From: Sell Your Company with $0 Taxes? QSBS Explained
Trust Creation Service for QSBS Eligibility
This business idea revolves around creating a specialized service that assists startup founders in setting up trusts to maximize their QSBS eligibility. By establishing these trusts, founders can increase their potential tax-free capital gains when they sell their company. The service would guide founders through the process of trust creation, ensuring they understand the tax implications and benefits. It would also include ongoing administration of these trusts, making it easier for founders to manage their tax strategies effectively. This solution targets startup founders and entrepreneurs who are looking to optimize their exit strategy and minimize tax liabilities when selling their business. Specific tactics could include automated tools for trust management, educational resources for founders, and personalized consultations to tailor the trust structure to individual needs.
From: Sell Your Company with $0 Taxes? QSBS Explained
Tax Planning Platform for Independent Contractors
The second business idea is to develop a tax planning platform specifically designed for independent contractors. This platform would provide resources and tools for contractors to track their income and expenses, identify deductible business expenses, and plan for tax obligations. It could include features such as automated expense tracking, tax deduction calculators, and reminders for estimated tax payments. Additionally, the platform could offer educational content on maximizing deductions and understanding tax implications of being a contractor. This addresses the need for freelancers and independent contractors to manage their finances effectively, especially since they are responsible for their own tax payments. The target audience comprises freelancers, gig workers, and small business owners who operate as independent contractors. Strategies to attract users could involve content marketing that highlights tax-saving strategies and partnerships with freelance platforms to integrate the service.
From: Independent Contractor or Employee? Hiring Mistakes That Trigger an IRS Audit
IRS Compliance Software for Worker Classification
The idea is to create a software solution that helps businesses determine whether to classify a worker as an independent contractor or an employee based on IRS guidelines. This tool would provide a questionnaire that evaluates behavioral control, financial control, and the type of relationship between the employer and the worker, generating a report that suggests the most appropriate classification. The software could also help users draft compliant contracts and maintain necessary documentation to defend against potential audits. This addresses the pressing issue of misclassification, which can lead to significant fines and penalties. The target audience includes small business owners, freelancers, and HR professionals who need assistance navigating complex labor laws. Marketing strategies could include partnerships with tax advisors and HR consultants to promote the software to their clients.
From: Independent Contractor or Employee? Hiring Mistakes That Trigger an IRS Audit
Recent Episodes
Live Case Study: How We Cut $50K Off His Tax Bill (Step by Step)
Host: Mike Jesowshek, CPA
3 ideas found
Car Write-Offs Explained: The 2025 Tax Rules You Need to Know
Host: Mike Jesowshek, CPA
2 ideas found
Independent Contractor or Employee? Hiring Mistakes That Trigger an IRS Audit
Host: Mike Jesowshek, CPA
2 ideas found
Why the Wealthy Use Oil & Gas Investments to Cut Six Figures Off Their Taxes
Host: Mike Jesowshek, CPA
3 ideas found
Q&A: If I Started a Business Today, This Would Be My Tax Strategy
Host: Mike Jesowshek, CPA
How Section 831(b) Captive Insurance Protects Your Business and Saves You Taxes
Host: Mike Jesowshek, CPA
1 idea found
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