The Life Planning 101 Podcast

How Much Will Uncle Sam Benefit from the Sale of Your Business?

In this episode, Angela discusses tax planning strategies for business owners considering transitioning or selling their business. She emphasizes the importance of proactive tax planning to maximize benefits and avoid common mistakes that could negatively impact the sale and future financial security. The episode outlines three critical 'don'ts' related to tax planning when transitioning a business.
Key Takeaways 💡
Business owners should not be ignorant about potential taxes when selling their business, as guessing or adding estimated taxes to the business price can deter serious buyers. Understanding the tax implications for both the seller and the buyer can create negotiating power, potentially structuring the sale in a way that benefits both parties through deductions and favorable tax avenues.
Business owners should seek professional advice to obtain accurate tax assessments, as demonstrated by an example where a second opinion significantly reduced the initial tax estimate. Many business owners incorrectly assume they cannot sell their business due to high taxes, but strategic tax planning can significantly mitigate these taxes, potentially creating tax savings during the sale and throughout retirement.
Business owners should not wait until the last minute to engage in tax planning, as some tax strategies require years of implementation to be effective. For example, Section 1202 allows an exemption of up to $10 million or 10 times the basis when selling a business, but to maximize this benefit, planning needs to start six to seven years in advance.
Business owners should not ignore estate planning when preparing to sell their business, as it presents an optimal time to mitigate estate tax risks. Gifting shares of the business to trusts or heirs can be done at a lower valuation, potentially saving millions in estate taxes and future growth.
Business owners need expert assistance to navigate the complexities of tax planning during a business sale, as most lack the experience to simultaneously mitigate taxes during the sale, afterward, and at death. A team of professionals, including accountants and tax attorneys, can provide comprehensive support and specialized knowledge to optimize tax outcomes.

3 Costly Mistakes When Transitioning Your Business

In this episode, Angela discusses costly mistakes business owners make when transitioning their businesses. She emphasizes the emotional aspect of business ownership and how it can lead to poor decision-making during the transition process. The episode focuses on three common mistakes: running on empty, building a honeybee business, and prioritizing everything, and provides tips for avoiding these pitfalls to ensure a successful transition and retirement.
Key Takeaways
Many business owners drive themselves too hard without planning for the future, leading to burnout, health issues, or even death, which forces them to transition their business under less than ideal circumstances. Waiting until a crisis occurs to plan for the transition often results in not getting top dollar for the business and a grimmer retirement outlook, both financially and physically. Business owners should start planning for their business transition now, regardless of their age, considering that they will eventually exit the business either vertically or horizontally.
Business owners often create a "honeybee business" where every decision and approval must go through them, making the business unattractive to potential buyers or successors. Buyers are less likely to invest in a business that heavily relies on the owner, as it poses risks of instability and loss of customers or key employees after the owner's departure. Instead, business owners should aim to create a self-managing company, like a "Christmas tree," that can sustain and grow even in their absence.
Business owners frequently prioritize everything in their business, living in the moment rather than strategically planning for the future and work-life balance. This approach can negatively impact the business, the owner's health, their family, and their future retirement. To avoid this, business owners should ensure their business is ready to transition or sell every quarter, giving them the choice to either keep growing it or sell it, and they should identify and address any gaps that prevent this from happening.
Progress starts with honesty, especially with oneself, and business owners need to acknowledge the changes they must make to prepare their business for transition. If business owners want their business to be attractive and ready for transition, leave a lasting legacy, and retire successfully, they need to take action now. There are resources available to help business owners with this process, and they should take advantage of them rather than waiting until they are burned out and forced to make hasty decisions.

This Week in the Market - Episode 86 (8/22/25)

In this episode, Aaron Kennedy, Sam Barker, and Kade Sparger discuss the week's market activity, the potential impact of interest rate cuts, and the importance of financial literacy and legacy planning. They explore how different sectors respond to economic announcements and the changing landscape of investment risk appetite. The guys also touch on the potential of Bitcoin and the need for financial education within families.

This Week in the Market - Episode 85 (8/15/25)

In this episode, Aaron, Sam, Kade, and Henry discuss the psychological challenges of investing in individual stocks versus viewing oneself as an owner of a company. They delve into the importance of long-term investment strategies and analyze specific companies, Novo and Palantir, to illustrate the differences between stock trading and company ownership. The guys also touch on market trends, value investing, and the potential impact of AI on the economy.

Where Are You Getting Advice?

In this episode, Angela discusses the importance of seeking sound advice and avoiding common pitfalls. She shares humorous anecdotes of bad advice and emphasizes the need to be cautious about the voices influencing our decisions. Angela highlights the significance of having a trusted team of professionals to address various aspects of life planning, including business, finances, and legacy.
Key Takeaways 💡
It is important to be mindful of the sources of advice we receive and how they impact our decisions, not only in faith but also in relationships, raising children, business, and financial matters. There is a lot of advice available on every topic, but it's crucial to discern whether it's accurate and appropriate for your specific situation, especially with the rise of AI and readily available information on the internet.
Relying solely on a single professional, even a trusted one, can lead to gaps and overlaps in financial plans because they may not have a holistic view or the necessary expertise in all areas. It is important to ensure that the professional is equipped with the right tools and knowledge to provide comprehensive guidance, as even well-intentioned professionals can give bad advice if they lack expertise in a particular area.
Bad advice from even skilled professionals can stem from two main reasons: they may not know what they don't know, leading them to offer advice outside their expertise, or the right questions are not being asked, resulting in a limited or biased perspective. For instance, asking a banker how to pay for a business succession plan may lead to solutions involving banking products, while a broader approach might consider tax benefits, insurance, or alternative funding methods.
As financial situations grow more complex, individuals outgrow the need for a single professional and require a team of experts, with a quarterback to lead the charge and coordinate efforts. The role of a life planner is to help individuals define what it means for them to live life on purpose, understand their future goals, current situation, family dynamics, and feelings about risk and money, and then identify the right professionals to involve at the appropriate times.
When seeking advice for business, money, or legacy matters, it's beneficial to consult with a life planner first to help formulate the right questions and avoid costly mistakes down the road. Life planners can help identify holes in financial plans, determine which professionals need to be involved, and ultimately guide individuals towards living life on purpose.

This Week in the Market - Episode 84 (8/8/25)

In this episode of Life Planning 101's Black and White Market Minute, Aaron Kennedy and Sam Barker discuss the potential impacts of tariffs, the performance of their stock strategies, and the valuation of companies in the current market. They also explore the implications of allowing Bitcoin in 401(k)s and the democratization of alternative investments.

This Week in the Market - Episode 83 (8/1/25)

In this episode, Aaron, Sam, and Henry discuss the irrationality and volatility of the market, particularly during earnings season. They highlight the disconnect between strong earnings reports and stock performance, emphasizing the influence of computer-driven trading and short-term investment strategies. The guys also share strategies for weathering market downturns and taking advantage of opportunities to buy quality companies at discounted prices.

Retirement Blunders

Angela discusses common blunders people make when planning for or entering retirement. She emphasizes the importance of planning and avoiding mistakes that can jeopardize financial stability and overall well-being in retirement. The episode covers five key blunders and offers advice on how to avoid them.
Key Takeaways 💡
Many people mistakenly treat their first year of retirement as a windfall, especially ranchers, farmers, and business owners who are used to spending when they have cash available. Spending too much money early in retirement can be devastating to long-term financial stability, so it's important to avoid this common pitfall.
To avoid overspending, retirees need a spending plan that their retirement nest egg can support, an investment plan to support that spending plan, and a backup plan for unexpected events. It's crucial to have the discipline to stick to these plans to ensure long-term financial security.
Many retirees incorrectly assume that their taxes will always be low in retirement, but this isn't always the case, especially if they retire in their early sixties without taking Social Security or taxable distributions. Failing to take advantage of lower tax years can lead to significantly higher tax payments later on, especially when Social Security and required minimum distributions kick in, and also consider the widow's penalty.
Taking Social Security at age 62 is a common mistake that can cost retirees a significant amount of money, as waiting each year results in an 8% increase in benefits. It's important to conduct a break-even maximization analysis to determine the optimal time to start receiving Social Security, considering factors like health, life expectancy, marital status, and tax situation.
It is a common misconception that retirees need to lower their investment risk, but this may not always be true, as retirement can last just as long as their working years. Taking less risk can put retirees at risk of not keeping up with inflation, so it's important to get the risk right and plan for the sequence of returns risk, which can be catastrophic to retirement if not properly managed.
Many retirees set themselves up for failure by not having a clear purpose or plan for what they are retiring to, focusing solely on retiring from something. The newness of hobbies can wear off quickly, so it's important to continue using one's God-given strengths and talents, challenge the mind and body, and maintain meaningful relationships to avoid losing purpose and direction in retirement.

This Week in the Market - Episode 82 (7/18/25)

In this episode, Kade Sparger is joined by Aaron Kennedy and Sam Barker to discuss the market's recent all-time highs and the factors driving it. They touch on the impact of tariffs, tax policies, and the potential of AI and deregulation on economic growth. Aaron emphasizes the importance of long-term planning and not getting caught up in daily market fluctuations.

One Big Beautiful Bill Act - Part 2

This week Angela continues the discussion on the One Big Beautiful Bill Act. This episode focuses on student loans, charitable gifting, new tax legislation for individuals, and new tax legislation for businesses and farmers. The aim is to provide a broad overview to prompt listeners to inquire about potential impacts on their financial situations.
Key Takeaways 💡
The One Big Beautiful Bill Act introduces a lifetime borrowing cap for student loans, with graduates capped at $100,000 and medical/law students at $200,000, and further limitations for part-time students. Parent Plus loans now have a cap of $65,000, and repayment options have been simplified to just two choices, making it crucial to understand the implications for financial aid planning.
The new tax legislation introduces a 0.5% income floor for charitable write-offs, impacting the ability to deduct charitable gifts, and this floor also applies to corporations. This change means that individuals must now exceed this income threshold before they can begin to deduct their charitable contributions, potentially reducing the tax benefits of charitable giving.
The "no tax on tips, overtime, and Social Security" claims are misleading, as the legislation only provides exemptions on some tips, some overtime, and some Social Security income. There's an above-the-line exemption of $25,000 for qualified tips, but this phases out for higher incomes, and overtime has a $12,500 exemption with the requirement of separate reporting on the W-2, both clauses being eligible for only three years.
The "no tax on Social Security" is more of a senior deduction of $6,000 for those over 65, but it phases out for individuals with incomes starting at $75,000 or $150,000 for married couples filing jointly. This means that the promised benefits may not be as substantial as initially perceived, especially for seniors with higher incomes.
The legislation allows for 100% depreciation and bonus depreciation in one year, increasing the limits around Section 179 expensing up to $2.5 million. Additionally, certain qualified property used for manufacturing, agriculture, chemical production, or refining can be expensed at 100% in one year, though there are strong recapture rules over 10 years to consider.
Environmental quality incentives programs, conservation steward programs, and the agriculture conservation easement program have been funded through 2031, with increased funding due to the redirection of Inflation Reduction Act funds. There is also renewed funding through 2031 for smaller initiatives like well water programs and incentivizing farmers to open land for hunting and recreation, plus a feral swine eradication program for Texas.
The bill includes $66 billion in new spending for farm programs, the largest infusion since 2002, covering commodity programs, crop insurance, conservation, trade promotion, research, education, rural development, energy programs, and support for specialty crops. This presents numerous opportunities for farmers and ranchers to tap into various resources and programs.
The qualified small business stock exemption has been expanded, reducing the holding period to three years for partial gain exemptions, with 50% of gains not taxed at three years, 75% at four years, and 100% at five years. The exemption cap has also been increased to $15 million or 10 times the owner's basis, offering significant benefits for small business owners planning their exit strategies.

One Big Beautiful Bill Act - Part 1

In this episode, Angela discusses the "One Big Beautiful Bill Act" and its implications for individuals, business owners, farmers, and ranchers. She provides an overview of the bill, focusing on key aspects such as permanence and stability in the tax code, student and child-focused provisions, charitable gifting, state and local taxes, and new tax legislation.
Key Takeaways 💡
The extension and expansion of the 2017 Tax Cuts and Jobs Act brings permanence to several provisions, preventing taxes from reverting to 2016 rates and rules, which includes the alternative minimum tax (AMT). This stability allows families and business owners to make informed decisions about their financial future without the uncertainty of fluctuating tax laws.
The estate tax exemption is set at $15 million per person, adjusted for inflation, providing a stable foundation for estate planning. This permanency helps small business owners, farmers, and ranchers plan their estates with more certainty, although significant inflation may still require additional planning for larger estates.
The Section 199A business owner deduction, which allows a 20% deduction on business income for pass-through entities, has been extended and expanded. This extension includes higher income phase-in amounts and a minimum deduction, offering significant benefits to small business owners by reducing their taxable income.
Businesses can once again depreciate 100% of assets placed in service after January 19th, 2025, regaining the first-year bonus depreciation. Additionally, the ability to expense depreciation on equipment has increased to $2.5 million, up from $1.25 million, providing valuable tax benefits for business investments.
Opportunity Zones have been made permanent, offering a rolling five-year deferral of capital gains for investments in designated areas. Investing in rural Opportunity Zones may qualify for a 30% basis increase, enhancing the tax benefits and incentivizing investment in these areas.
Businesses that utilized the Employee Retention Credit (ERC) should seek counsel to ensure compliance, as the audit time has been extended, clawbacks are being enforced, and penalties have been elevated. The IRS is scrutinizing ERC claims, and businesses need to verify their eligibility and documentation to avoid potential issues.
Several electric vehicle and clean energy credits are set to expire soon, including credits for commercial clean vehicles, new clean vehicles, and previously owned clean vehicles. To take advantage of these credits, purchases must be made before September 30th for electric vehicles and December 31st for solar, wind, and home energy improvements.
The cap on the federal deduction for state and local taxes (SALT) has been temporarily increased to $40,000, but it begins to phase out with $500,000 of income and reverts back to $10,000 in 2030. However, the pass-through entity workaround, which allows deducting property expenses within a pass-through entity, remains a viable strategy to regain missing state and local tax deductions.

This Week in the Market - Episode 81 (7/2/25)

In this episode of Life Planning 101's Black and White Market Minute, Kade Sparger is joined by Aaron Kennedy and Sam Barker to discuss the current state of the market and potential future trends. They analyze recent market performance, the impact of economic news, and the psychological factors influencing investor behavior. The speakers also delve into the implications of the recent "big, beautiful bill" and offer advice on personal finance strategies, including Roth conversions and disciplined spending.