The Long Game

Nate Sosa, a CPA with expertise in real estate taxation, joins to reveal powerful tax strategies for real estate investors. He breaks down the mechanics of depreciation and its significance in reducing taxable income. Sosa explains the distinctions between active and passive income, and how specific tax treatments can benefit high-income earners. The discussion also covers cost segregation, smart timing for bonus depreciation, and the unique tax implications of short-term rentals. Listeners can learn to navigate these strategies for maximum savings.

Join Colin Stroud, founder of Go Somewhere, as he unpacks the art of maximizing credit card points for savvy travelers. Colin shares why responsible credit card use can be a game-changer for wealthier consumers. He details the advantages of travel rewards versus cashback cards and introduces a simple two-card system for optimal earnings. Listeners will learn smart redemption strategies, the pitfalls of booking through card portals, and why starting with travel goals is crucial. If you want to travel smarter, this conversation is packed with invaluable insights!

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 deductionsPre-Tax Deductions: How these can lower your taxable income and what to look forTaxes Withheld: Knowing your federal and state tax withholdingsAfter-Tax Deductions: Mega Backdoor Roth 401k and ESPPEmployer Benefits: What to track and consider for your overall compensationNet Pay: Knowing what you actually take home------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: 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 entrepreneurshipHow effective financial planning can empower you to make life-changing decisionsThe importance of liquidity and cash flow in achieving your ideal lifestyleReal-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----✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: 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 indexingHow direct indexing helps you harvest tax losses while tracking an indexWho direct indexing makes sense for (and who should skip it)When to switch from standard direct indexing to a long/short strategyReal-world scenarios where direct indexing can create massive tax savings-------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: 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 penaltiesSetting up the right retirement accounts, including solo 401(k)s and cash balance plansMaximizing deductions and expenses to reduce taxable incomeStrategies for managing cash flow and building wealth outside of your business-------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: 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 consultantsCommon triggers for leaving corporate jobsThe significance of cash management and financial planning for new business ownersStrategies for optimizing tax situations during low-income yearsThe importance of finding the right financial advisor for your unique needs-------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: 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 employeesWho is a good candidate for an ESOP?Real-life examples and success stories-------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: 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 planOptions-based strategies (like covered calls and collars)Charitable strategies to reduce capital gains taxesDirect indexing and long-short strategies for tax efficiencyExchange funds and Opportunity Zone funds as diversification tools-----------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: 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 contributionsHow 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-------------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.