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Thinking about converting your C Corporation to an S Corporation? Before making the switch, do you know about the Built-In Gains (BIG) Tax—and how it could cost you thousands if you don’t plan ahead?

In this episode, Mike Jesowshek breaks down the Built-In Gains (BIG) Tax, a critical consideration for business owners converting from a C Corporation to an S Corporation. He explains why this tax exists, how it prevents businesses from avoiding double taxation, and the conditions under which it applies. Mike walks through key scenarios where the BIG Tax may or may not apply, how to calculate it, and the best strategies for minimizing or avoiding it. 

[00:00 - 03:30] Understanding the Built-In Gains (BIG) Tax

• Mike introduces the BIG Tax and its purpose in preventing tax avoidance.
• What is the difference of taxation for C Corps versus S Corps?
• Owners need to be aware of BIG Tax before making an S Corp election.

[03:31 - 11:15] Calculating the BIG Tax & IRS Considerations

• Mike shares the three key conditions that trigger the BIG Tax.
• Fair market value vs. adjusted basis determines built-in gains.
• Mike discusses the step-by-step breakdown of how to calculate the BIG Tax.
• Proper asset valuation at the time of conversion is critical.

[11:16 - 14:00] Strategies to Avoid the BIG Tax

• Hold onto assets for at least five years to bypass taxation.
• Time asset sales in loss years to offset taxable gains.
• Utilize NOL (Net Operating Loss) carryovers from the C Corp.

[14:01 - 17:32] When the BIG Tax Does NOT Apply and Final Considerations

• Mike shares scenarios where business owners don’t have to worry about the BIG Tax.
• BIG Tax is not a reason to avoid an S Corp election—planning is key.
• What is the importance of documentation and fair market value assessments?

Notable Quotes:

“The BIG Tax exists to stop business owners from electing S Corp status right before a liquidation or sale to dodge double taxation.” - Mike Jesowshek, CPA

“Holding onto your assets for five years after converting to an S Corp is the simplest way to avoid the Built-In Gains Tax.” - Mike Jesowshek, CPA

“The BIG Tax is important to understand, but it’s not a reason to avoid an S Corp election. With the right planning, an S Corp is still a powerful tax-saving strategy.” - Mike Jesowshek, CPA

Check out this episode’s blog post: https://www.taxsavingspodcast.com/blog/beware-of-hidden-built-in-gain-big-taxes-when-transitioning-to-s-corporation

Click here to book a demo call or you can visit https://taxelm.com/demo/ 

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Facebook Group: https://www.facebook.com/groups/taxsavings/

YouTube: www.TaxSavingsTV.com 

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Have you ever considered how advanced tax strategies, from customized retirement contributions to optimizing home office deductions, might lower your overall tax burden? 

In this Q&A episode, host Mike Jesowshek answers listener questions on various tax topics. He covers issues ranging from retirement planning strategies, such as after‑tax contributions and Roth conversions in a solo 401(k), to the proper methods for paying oneself as a sole proprietor versus an S corporation. Mike also explains home office deductions, board meeting expenses, handling duplicate tax forms, and business entity conversions. 

[00:00 -  05:02] Retirement Contributions and Solo 401(k) Options

• Mike discusses using after‑tax contributions and a Roth conversion in a solo 401(k) for high‑income earners.
• New members receive immediate access to a comprehensive suite of tax-saving tools and consultations.

[05:02 - 10:42] Owner Draws, Home Office Deductions, and Board Meeting Expenses

• Mike explains how to oneself as a sole proprietor using owner draws versus payroll for S corporations.
• Understand that taking money out of a business as an owner draws does not reduce taxable profit.
• Ensure that business spaces are used exclusively for business, and document meetings carefully when using home space.

[10:42 -  15:32] Hiring Family Members, Deducting Mileage Expenses, and Entity Conversion

• Mike discusses claiming mileage expenses when an employee uses a personal vehicle for business.
• Recognize that converting a C corporation back to an LLC may trigger taxable events; professional consultation is advised.

[15:32 - 20:17] Handling Duplicate 1099 Forms and Short-Term Rental Deductions

• Work with the issuer to correct mistakes or offset the extra reporting with a matching expense entry.
• Understand the timing of deductions and whether expenses need to be capitalized based on service start dates.

[20:17 - 27:20] S Corporation and Subsidiary Structures; Home Office with Additional Facility

• Mike details the benefits of an S corporation holding company structure for multiple LLCs and addresses home office deductions when using a separate facility.
• Proper structuring can consolidate profit and loss reporting, and the administrative office rule allows a home office deduction even when an additional business location exists.

Direct Quotes:

"If you are helping out family members, and those family members can also do some work for your business, why not get a business deduction for that help that you want to do anyways?" - Mike Jesowshek, CPA

Check out this episode’s blog post! Visit https://www.taxsavingspodcast.com/blog/tax-q-a-short-term-rentals-1099-confusion-entity-conversions-and-creative-tax-strategies 

Click here to book a demo call or you can visit https://taxelm.com/demo/ 

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Are you making the most of the new 2025 tax changes, or could a simple tax strategy adjustment save you thousands?

In this episode, Mike breaks down key tax changes for 2025 that small business owners need to know. He covers adjustments to tax brackets, increases in the standard deduction, new mileage rates, retirement contribution limits, and updates to gift and estate tax exclusions. He explains how these changes impact tax planning, emphasizing strategies to optimize deductions and avoid unnecessary tax burdens. Additionally, he highlights potential future tax changes with the incoming administration and the importance of staying updated.

[00:00 - 05:21] Understanding the 2025 Tax Brackets

• Tax brackets adjust annually for inflation, ensuring more income is taxed at lower rates.
• Mike explains how tax brackets work and why crossing into a higher bracket doesn’t mean all income is taxed at that rate.
• Knowing your tax bracket can help with strategic tax planning, such as Roth conversions and deductions.

[05:22 - 10:24] Mileage Deduction Increase for 2025

• Mike discusses when to use the mileage method versus actual expenses for vehicle deductions.
• Choosing the right deduction method (mileage vs. actual expenses) depends on vehicle costs and business mileage.

[10:25 - 14:44] Standard Deduction Updates

• The standard deduction increases to $30,000 for married filers and $15,000 for single filers.
• How can this impact taxpayers deciding between itemized and standard deductions?
• Most taxpayers will benefit from the standard deduction, but strategic "bunching" of itemized deductions can provide tax advantages.

[14:45 - 18:53] Retirement Contribution Limits Increase

• Employee 401(k) contribution limit rises to $23,500, while IRA limits remain at $7,000.
• Maximizing retirement contributions helps reduce taxable income and build financial security.

[18:54 - 21:53] Gift & Estate Tax Changes

• The gift tax exclusion increases to $19,000 per recipient.
• Estate tax exemption rises to $13.99 million, affecting wealth transfer planning.
• Strategic gifting can help reduce taxable estates and transfer wealth efficiently.
• Proactive tax planning ensures business owners take advantage of new tax laws while avoiding potential pitfalls.

Quotes:

“Simply going into a new tax bracket doesn’t mean all of your income is taxed at that higher rate.” - Mike Jesowshek, CPA

“More of your income being taxed at a lower rate is good news—it means you’re keeping more of what you earn.” - Mike Jesowshek, CPA

Click here to book a demo call or you can visit https://taxelm.com/demo/ 

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Facebook Group: https://www.facebook.com/groups/taxsavings/

YouTube: www.TaxSavingsTV.com 

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Are you tired of overpaying on taxes and looking for straightforward strategies to save money while growing your business?

In this episode, Mike Jesowshek announces the launch of his new book, Small Business Tax Savings Handbook. The book aims to help small business owners, entrepreneurs, and freelancers reduce taxes legally and build financial stability. Designed to be accessible and action-oriented, it includes proven tax strategies, practical examples, and end-of-chapter checklists. Mike also discusses launch week bonuses, including a tax strategy checklist, a live Q&A webinar, and a bonus chapter. The episode emphasizes the importance of year-round tax planning and implementing strategies to maximize savings.

[00:00 - 05:40] What the Book Offers

• Mike explains the book’s purpose: reducing taxes and empowering small business owners.
• Understanding tax incentives is crucial for financial success.
• He shares step-by-step guides to make complex tax topics easy to understand.
• Implementing strategies leads to immediate and long-term savings.

[05:41 - 07:17] Who the Book is For

• The book is designed for small business owners, entrepreneurs, and freelancers.
• Mike highlights the need for year-round tax planning.
• Effective tax planning can create opportunities for wealth growth.

[07:18 - 09:11] Launch Week Bonuses and Call to Action

• Mike gives details about bonuses: tax strategy checklist, live Q&A, and a bonus chapter on 2025 strategies.
• He encourages listeners to purchase the book and leave reviews.

Direct Quotes:

“This isn’t just another tax book; it’s a game plan for small businesses ready to take control of their financial future.” - Mike Jesowshek, CPA

“You can learn all day, but until you implement it, you don’t see tax savings.” - Mike Jesowshek, CPA

“Effective tax planning isn’t just for tax season—it’s a year-round effort.” - Mike Jesowshek, CPA

Check out this episode’s blog post: https://www.taxsavingspodcast.com/blog/introducing-the-small-business-tax-savings-handbook

Order your very own copy of the Small Business Tax Savings Handbook: How to Save on Taxes While Growing Your Business and Wealth by visiting Amazon!

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Facebook Group: https://www.facebook.com/groups/taxsavings/

YouTube: www.TaxSavingsTV.com 

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What if you could apply the wealth-building strategies of billionaires to your own small business? 

In this episode, Mike Jesowshek demystifies the concept of a family office, traditionally associated with the ultra-wealthy, and explains how small business owners can adopt similar strategies to build wealth, optimize taxes, and create a legacy. He details the roles and responsibilities within a family office, such as tax strategists, attorneys, and financial advisors, and outlines actionable steps for organizing finances, assembling a team, and reviewing progress regularly. Mike emphasizes starting small, documenting plans, and growing the family office alongside business success, offering practical guidance for sustainable financial management.

Discover how to create a family office tailored to your goals by tuning in!

[00:00 - 02:11] Why Small Business Owners Need a Family Office

• Mike explains what a family office is and how it manages wealth.
• The principles of family offices can be scaled to any income level.
• Prioritize creating a financial safety net alongside business investments.

[05:13 - 10:23] Key Roles in a Family Office

• Mike breaks down the core components, including tax strategists, financial advisors, attorneys, and bookkeepers.
• A well-structured team can significantly enhance tax efficiency and wealth growth.

[10:24 - 16:12] Building Your Family Office

• Steps to get started: organize finances, fill roles, and align the team with personal goals.
• Mike stresses the importance of due diligence when selecting advisors.
• Even small steps, like self-managing roles initially, can lay the foundation for success.

[16:13 - 21:40] Continuous Improvement and Documentation

• Mike encourages regular reviews and adjustments as the business evolves.
• He suggests documenting roles and plans for clarity and legacy planning.
• Consistent reviews and clear documentation prevent stagnation and ensure long-term success.

[21:41 - 24:13] Closing Thoughts and Resources

• Mike reiterates the value of taking action and starting small.
• Proactive implementation leads to significant financial benefits.

Direct Quotes:

"A family office is kind of like a CEO-level approach to managing wealth." - Mike Jesowshek, CPA

"You get to pick and choose what your family office looks like—start small and grow as your business grows." - Mike Jesowshek, CPA

"Think of your family office as a tool belt: each role is a tool that helps you achieve your goals." - Mike Jesowshek, CPA

"Don’t just fill a role to fill a role—do your due diligence and make sure the people you choose align with your vision." - Mike Jesowshek, CPA

Check out this episode’s blog: https://www.taxsavingspodcast.com/blog/build-your-own-family-office-start-saving-taxes-and-building-wealth-today

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Are you maximizing your tax savings while building your retirement plan, or leaving opportunities on the table?

In this episode, Mike Jesowshek is joined by Matt Ruttenberg to discuss strategies for reducing your 2024 tax bill through retirement contributions and planning. They highlight key deadlines for individual and employer contributions, such as the April 15th cutoff for IRAs and the extended filing deadlines for employer contributions. They also delve into options like solo 401(k)s, safe harbor plans, and cash balance plans, emphasizing the importance of early planning and ongoing consultation to maximize tax savings and retirement benefits.

[00:00 - 02:17] Introduction

• Mike welcomes Matt Ruttenberg back to the show as a trusted retirement expert.
• Discussion begins with how the new year presents opportunities to address past tax planning mistakes.

[02:18 - 05:59] IRA Contributions

• Deadlines for Roth and traditional IRAs are April 15th.
• Contributions are based on individual earned income, not business profits.
   Lesson: Plan IRA contributions early, as extensions don't apply.

[06:00 - 10:14] Profit Sharing and Employer Contributions

• Employer contributions for profit sharing plans can be made until the extended filing deadline.
• Different strategies, such as "new comparability," can maximize owner benefits.

[10:15 - 13:28] Solo 401(k)s and New Rules

• First-year solo 401(k) participants can contribute employee portions up to April 15th.
• This rule applies to sole proprietors and single-member LLCs, not S-corporations.

[13:29 - 16:11] Safe Harbor and Compliance

• Safe harbor plans help owners and highly compensated employees avoid compliance issues.
• A 4% non-elective contribution can be made post-deadline to improve compliance.

[16:12 - 24:33] Advanced Plans: Cash Balance and Defined Benefit

• High-income businesses can use defined benefit plans for contributions up to $300,000.
• These plans require actuary involvement and multi-year commitments.

[24:34 - 31:16] Key Takeaways and Planning for 2025

• Employer contributions can be made until the filing deadline, including extensions.
• 2025 should focus on proactive tax planning to avoid last-minute issues.

Direct Quote:

"All 401(k) plans are not created equal; work with someone who knows the options available to you." - Matt Ruttenberg

Build a custom 401(k) for your business by visiting https://lifeincrs.com/tax-savings-podcast/ 

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Facebook Group: https://www.facebook.com/groups/taxsavings/

YouTube: www.TaxSavingsTV.com 

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How prepared are you to make 2025 your best financial year yet?

In this episode, Mike Jesowshek dives into strategic financial planning for 2025, emphasizing the importance of a financial summary document, proactive tax planning, and long-term strategic business planning. He explains how to create a comprehensive financial summary, differentiate between tax preparation and tax planning, and implement actionable goals to achieve financial clarity and growth. By focusing on yearly updates, tax strategies, and structured plans, listeners are encouraged to approach the new year with clarity and purpose.

Explore how a clear financial summary, tax strategies, and strategic planning can set you up for success.

[00:00 - 05:12] Creating a Financial Summary Document

• Mike explains the purpose and benefits of a financial summary document.
• Annual updates to a financial summary provide clarity and preparedness.

[05:13 - 12:39] Tax Preparation vs. Tax Planning

• Mike shares the distinction between compliance-focused tax preparation and strategy-driven tax planning.
• Implementing tax strategies is crucial for minimizing tax liability.

[12:40 - 17:20] Strategic Business Planning

• Strategic planning involves envisioning a 10-year perfect scenario and breaking it down into actionable goals.
• Clear planning transforms business goals into achievable steps.

[17:21 - 20:34] Key Takeaways and Resources

• Mike recaps the importance of financial summaries, tax planning, and strategic business goals.
• Success is intentional and requires consistent planning.

Direct Quotes:

"Success doesn't just happen. It's planned." - Mike Jesowshek, CPA

"Learning is important, but implementation is the next step." - Mike Jesowshek, CPA

"Strategic planning helps turn dreams into reality by breaking down goals into actionable steps." - Mike Jesowshek, CPA

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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YouTube: www.TaxSavingsTV.com 

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Are you prepared for the IRS’s new 1099-K reporting rules and how they could impact your business's bottom line?

In this episode, Mike Jesowshek discusses the significant changes to the IRS 1099-K rule and its potential impact on small businesses, freelancers, and online sellers. The rule, initially requiring payment processors to report income over $20,000, is being gradually lowered to $600 by 2026. Mike explains how this rule aims to address underreported income and outlines the implications for businesses accepting payments via platforms like PayPal, Venmo, and Stripe. He emphasizes the importance of accurate reporting to avoid IRS scrutiny and offers a free demo call to help listeners prepare their tax strategies.

[00:00 - 06:42] Why the 1099-K Rule Was Introduced

• Mike discusses the significance of the 1099-K for freelancers, small businesses, and gig workers.
• Understanding this rule is key to avoiding surprises during tax season.
• The motivation behind the rule: addressing underreported income from goods and services.
• Report all income accurately, even without a 1099-K.

[06:43 - 10:37] Who This Rule Impacts

• Mike dives deep into who’s affected: freelancers, gig workers, and small businesses.
• Proactively distinguish between personal and business transactions.

[10:38 - 14:22] Timeline and Rollout of the Rule

• Breakdown of the phase-in thresholds:
  • 2024: $5,000
  • 2025: $2,500
  • 2026: $600
• Mike highlights potential changes due to legislative pushback.
• Stay updated on the latest developments and adapt your approach.

[14:23 - 18:58] Avoiding Tax Issues and Next Steps

• Mike shares tips for accurate reporting and reconciling 1099-K forms with your tax returns.
• Be proactive in managing your taxes to avoid penalties and ensure compliance.

Direct Quotes:

“The 1099-K is a tool to let the IRS know what funds are being processed and who is receiving those funds.” - Mike Jesowshek, CPA

“This rule isn’t about changing how taxes work; it’s about changing how income is reported.” - Mike Jesowshek, CPA

“Don’t wait for a 1099-K to report your income. Always report all earnings to stay on the right side of the law.” - Mike Jesowshek, CPA

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Facebook Group: https://www.facebook.com/groups/taxsavings/

YouTube: www.TaxSavingsTV.com 

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What if a few simple shifts in your business structure and financial habits could set you ahead of 99% of companies?

In this episode, Mike Jesowshek, a CPA and founder of Taxelm, shares practical strategies for small businesses to gain a competitive edge without requiring massive investments or risky tactics. He emphasizes the importance of establishing a proper entity structure as the foundation for growth, maintaining an accurate and cloud-based bookkeeping system, and utilizing financial data to make informed business decisions. Mike also highlights key tax deductions and offers resources to help business owners optimize their financial strategies effectively.

[00:00 - 04:50] Introduction: Setting the Stage

• Mike introduces the theme of outpacing 99% of businesses with simple, effective strategies.
• Success doesn’t require excessive risk or investment; it starts with foundational business practices.
• Transitioning to an S Corporation can lead to significant tax savings.
•  A well-structured entity is essential for tax efficiency and long-term growth.

[04:51 - 10:00] Building a Solid Foundation for Growth and The Backbone of Business

• Mike shares the importance of creating a management company structure for multiple business entities.
• Clear and organized entity structures reduce risks and enhance scalability.
• Consistent bookkeeping helps identify inefficiencies and drives better financial decisions.

[10:01 - 19:26] Leveraging Financial Data and Resources

• It is vital to use accurate financial statements for tax planning and business strategy.
• Mike offers a free document outlining tax deductions to maximize savings.
• Proactive financial management unlocks opportunities for growth and profitability.

Direct Quotes:

“Your entity structure is the foundation of how your business operates and grows.” - Mike Jesowshek

“Bookkeeping isn’t just for taxes; it’s the backbone of understanding your business’s financial health.” - Mike Jesowshek

“A cloud-based system done correctly gives you actionable insights. Done poorly, it gives you nothing.” - Mike Jesowshek

“With the right foundation, you can grow into the 1% of business owners who succeed at scale.” - Mike Jesowshek

Check out this episode’s blog: The Ultimate Guide to Maximizing Business Deductions and Write-Offs

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Facebook Group: https://www.facebook.com/groups/taxsavings/

YouTube: www.TaxSavingsTV.com 

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What if the key to unlocking exponential growth in your 401k is simply reaching $100,000? Could this milestone be the turning point for your financial freedom?

In this episode, Mike Jesowshek dives into the concept of why your 401k experiences explosive growth after reaching a $100,000 threshold. He explains the mechanics of compounding interest, the rule of 72, and how starting early can significantly impact retirement savings. Mike also introduces the idea of self-funded retirement accounts, detailing how business owners can leverage them to invest in areas such as real estate or cryptocurrency. He underscores the importance of surpassing the $100,000 mark to unlock greater investment opportunities and financial flexibility, offering practical tips to achieve this milestone efficiently.

[00:00 - 06:15] The Power of Compound Growth

• Mike shares his personal financial journey and why $100,000 is a pivotal milestone for investors.
• He breaks down the "rule of 72" and how it applies to achieving financial goals.
• Early and consistent investing accelerates your financial trajectory.

[06:16 - 12:10] Why $100,000 is a Game-Changer

• Mike discusses how hitting $100,000 opens doors to investment opportunities beyond traditional options.
• Reaching this milestone creates leverage for greater diversification and growth.

[12:11 - 16:45] How to Get to $100,000 Faster

• Mike highlights the importance of automating investments and sticking to a long-term strategy.
• Focus on consistency and discipline to build momentum.

[16:46 - 19:24] Final Takeaways and Encouragement

• Mike recaps the importance of achieving $100,000 and how it sets the foundation for future wealth-building.
• Take the first steps today, no matter where you are in your financial journey.

Direct Quotes:

"Think of compounding interest like a snowball rolling down a hill—small at first, but it can grow into something massive over time." - Mike Jesowshek, CPA

"The rule of 72 gives you a simple formula: divide 72 by your interest rate, and you’ll know how long it takes for your money to double." - Mike Jesowshek, CPA

"Starting early with your retirement savings means you’re giving your money more time to work for you, doubling multiple times before retirement." - Mike Jesowshek, CPA

______

Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

Join TaxElm: https://taxelm.com/

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Podcast Website: https://www.TaxSavingsPodcast.com

Facebook Group: https://www.facebook.com/groups/taxsavings/

YouTube: www.TaxSavingsTV.com