Want to use real estate to cut your tax bill? In this episode I'm joined by CPA Nate Sosa to break down the real tax advantages of owning real estate, especially for business owners and high-income earners. You’ll learn:

• The difference between active and passive real estate tax treatment
• When real estate losses can (and can’t) offset your W-2 or business income
• How depreciation, bonus depreciation, and cost segregation work
• Why short-term rentals can be a powerful (but tricky) tax play
• The truth about depreciation recapture and what to plan for
• How to time real estate investments in high-income years to legally save thousands

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

If you've ever wondered how to make the most out of your credit card rewards, this episode is for you. We break down how they can be a powerful tool for those looking to maximize their spending. Colin shares his thoughts on:

• Why Credit Cards Can Be Beneficial: Using credit cards responsibly and how they can offer significant advantages, especially for those with higher incomes
• The Basics of Earning Points: The benefits of cash back cards vs travel rewards cards
• Redemption Strategies: How to leverage your points effectively, including tips on transferring points to airline and hotel partners for maximum value
• The Two-Card System: A simple two-card strategy that allows you to optimize your spending without overwhelming complexity

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I break down the importance of understanding your pay stub. Many people overlook it, which can lead to missed tax opportunities, under-saving for retirement, and overpaying for benefits. Some highlights:

• Gross Pay: Understanding your full earnings before deductions
• Pre-Tax Deductions: How these can lower your taxable income and what to look for
• Taxes Withheld: Knowing your federal and state tax withholdings
• After-Tax Deductions: Mega Backdoor Roth 401k and ESPP
• Employer Benefits: What to track and consider for your overall compensation
• Net Pay: Knowing what you actually take home

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Zach Ashburn to discuss the intersection of financial planning and personal freedom. Some highlights:

• The journey from corporate life to entrepreneurship
• How effective financial planning can empower you to make life-changing decisions
• The importance of liquidity and cash flow in achieving your ideal lifestyle
• Real-life stories of how financial planning has transformed lives (including Zach's experience as a foster parent and the impact it had on his family's decisions)
• How to maintain flexibility in your financial life

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, we break down direct indexing and long/short direct indexing, two powerful (and often misunderstood) tax strategies for high-income earners, business owners, and those with concentrated stock positions. We talk about:

• The difference between ETFs, mutual funds, and direct indexing
• How direct indexing helps you harvest tax losses while tracking an index
• Who direct indexing makes sense for (and who should skip it)
• When to switch from standard direct indexing to a long/short strategy
• Real-world scenarios where direct indexing can create massive tax savings

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I break down a detailed case study for business owners making over a million dollars a year. Some highlights & notes:

• The importance of choosing the right business entity (S-Corp vs. Sole Proprietorship)
• Understanding safe harbor tax payments to avoid penalties
• Setting up the right retirement accounts, including solo 401(k)s and cash balance plans
• Maximizing deductions and expenses to reduce taxable income
• Strategies for managing cash flow and building wealth outside of your business

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Zach Ashburn to break down the journey of transitioning from corporate life to entrepreneurship. Zach specializes in corporate exit planning and shares how professionals can leverage their skills to thrive independently. Some highlights:

• The golden age of entrepreneurship and the rise of specialized consultants
• Common triggers for leaving corporate jobs
• The significance of cash management and financial planning for new business owners
• Strategies for optimizing tax situations during low-income years
• The importance of finding the right financial advisor for your unique needs

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Wes and Doug from Alpha Architect to dive deep into the world of Employee Stock Ownership Plans (ESOPs). We talk about the options for selling a business, like selling to competitors or private equity, and break down the unique benefits of ESOPs. Some highlights:

• What is an ESOP and how does it function?
• Tax benefits for business owners and employees
• Who is a good candidate for an ESOP?
• Real-life examples and success stories

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Benjamin Lake, an advisor at Composition Wealth. If you own a significant amount of stock from your employer or have a concentrated investment, this episode is for you. We break down:

• The importance of having a clear financial plan
• Options-based strategies (like covered calls and collars)
• Charitable strategies to reduce capital gains taxes
• Direct indexing and long-short strategies for tax efficiency
• Exchange funds and Opportunity Zone funds as diversification tools

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined joined by Brad Caswell, an expert in the world of Donor Advised Funds (DAFs). He served as the Chief Operating Officer of Vanguard Charitable for 12 years, and now as a consultant helping organizations and individuals navigate the complexities of charitable giving. Some highlights from the episode:

• The benefits of using DAFs (including tax advantages and the ability to donate complex assets like real estate)
• The process of donating private assets and how to maximize your charitable contributions
• How to strategically time your donations to align with life events (such as selling a business or receiving an inheritance)

To find Brad: Charitable Solutions LLC

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by tax expert Chad Huebsch for a deep dive into the difference between stock and asset sales. If you're a business owner considering selling your business, understanding these two types of sales is essential, as they have significant tax implications. You'll learn about:

• How different industries approach these sales
• The significance of goodwill in business transactions
• Planning strategies to maximize your after-tax proceeds
• The hybrid 338(h)(10) election and its benefits
• The importance of having solid financials before selling

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, we dive deep into financial planning for individuals in their 30s-50s. We break down the unique challenges & opportunities that start to come up during this stage of life, including:

• Navigating cash flow and lifestyle creep
• Making informed housing decisions in today's market
• Balancing family responsibilities while planning for the future
• The importance of education funding and estate planning
• Strategies for effective investment and risk management

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Robert Rikard, a lawyer and partner at the Investor Loss Center, to discuss the controversial world of Index Universal Life (IUL) insurance. With the rise of social media influencers promoting IULs, many people are confused and misinformed about these products.

He explains how many agents misrepresent these products, often targeting middle America with unrealistic promises of tax-free retirement income. Some highlights from the episode:

• The rise of IULs and the misinformation surrounding them
• The commission structure that incentivizes agents to sell IULs
• Real-life case studies of clients who have suffered significant losses
• Alternatives to IULs that may be more suitable for average investors

Website: https://www.investorlosscenter.com

LinkedIn

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I sit down with Matthias Smith (founder and owner of Pioneer Capital Advisory) a brokerage firm specializing in SBA loans. We talk about:

- The different types of loans available for purchasing a business

- What an SBA loan is and how it works

- The importance of personal guarantees and life insurance in the loan process

- Common misconceptions about SBA loans

- Tips for prospective business buyers on preparing for the loan process

Connect with Matthias:

• Email – matthias@pioneercap.com
• LinkedIn – Matthias Smith
• Twitter – @SBA_Matthias

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Mark Cecchini, CFP® to discuss the intricacies of planning for an IPO. As the window opens up again, many employees are facing similar situations. We dive deep into the essential steps for preparing for an IPO, including:

• Understanding the difference between single-trigger and double-trigger RSUs

• The importance of having a solid financial plan and clear goals

• Strategies for managing equity concentration and diversification

• Tax planning considerations before and after an IPO

In this episode, I answer some of the most common financial questions submitted by you as we approach nearly 100,000 downloads. Some of the topics covered:

• Roth vs. Traditional IRAs: Which option is best for you based on your current and future tax brackets?
• SEP IRA vs. Solo 401k: Discover why a Solo 401k might be the better choice for solo business owners
• Tax Reduction Strategies for W-2 Employees: Learn effective ways to lower your lifetime tax bill
• Paying Off Your Mortgage: Should you pay off that 4.5% mortgage or invest instead?

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I'm joined by Chad Huebsch from Blueprint Tax to break down the importance of tax planning for business owners doing $1 million to $10 million. Chad shares valuable insights on entity selection, including the pros and cons of sole proprietorships, S-corporations, partnerships, and C-corporations. Some highlights:

• PTET (Pass-Through Entity Tax): How to maximize deductions for state and local taxes

• QBI (Qualified Business Income) Deduction: Understanding the thresholds and how to optimize your tax situation

• Retirement Planning: Exploring options like 401(k)s and cash balance plans to save on taxes while preparing for the future

• Hiring Family Members: The benefits and considerations of paying your children or spouse for work in your business

• Real Estate Strategies: Using short-term rentals and property ownership to offset income

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I’m joined by tax expert Roger Ledbetter to break down the recent tax bill. We talk about the new rules and discuss its potential impact on both individuals and businesses. Some highlights:

Key topics include:

• Changes to individual tax rates and deductions, including the standard deduction and child tax credit
• The implications of the bill for business owners, including QBI and bonus depreciation
• New deductions for tips, overtime, and car loan interest
• Insights on Opportunity Zones and Qualified Small Business Stock (QSBS)

✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I break down the ins and outs of hiring your children, spouse, and even other family members. Some highlights:

• Hiring Your Kids: The age at which your children can contribute meaningfully to your business and how you can set them up for financial success through tools like Roth IRAs and 529 plans

• The Benefits of Hiring Your Spouse: How to maximize contributions to retirement accounts and the tax benefits that come with it
• Navigating Family Dynamics: I share my personal experiences and insights on what makes a successful working relationship and the potential mistakes to avoid

• Tax Planning Tools: How to ensure that your hiring practices are compliant and beneficial for your tax situation, helping you set up your family for future success.

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

Many people give to charity but may not be doing so in the most tax-efficient way. In this episode, you'll learn:

• How charitable deductions work (and when they benefit you)

• The advantages of using Donor Advised Funds (DAFs)
• How donating appreciated stock can lead to significant tax savings
• Tips for high-income earners on structuring their charitable giving for optimal tax benefits

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.