
The Long Game
The Long Game podcast is all about educating 30-50 year old business owners and those with equity compensation on how to build wealth.
You will learn everything from the basics to complex tax, estate, and financial planning concepts from Thomas Kopelman as well as other qualified professionals.
Latest episodes

Jun 27, 2025 • 9min
Hiring Children & Spouses: Is This A Good Or Bad Idea?
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 plansThe Benefits of Hiring Your Spouse: How to maximize contributions to retirement accounts and the tax benefits that come with itNavigating Family Dynamics: I share my personal experiences and insights on what makes a successful working relationship and the potential mistakes to avoidTax 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.--------------------------------------✅ 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.

Jun 20, 2025 • 9min
How to Maximize Deductions Through Giving to Charity in the Most Efficient Way
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 savingsTips for high-income earners on structuring their charitable giving for optimal tax benefits---------✅ 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.

Jun 13, 2025 • 40min
Navigating the New Tax Bill (with Nate Sosa, CPA, MST)
In this episode, I'm joined by Nate Sosa, CPA, MST from Hall CPA, and we dive deep into:- The status of the new tax bill and what it means for you- Key changes, including bonus depreciation and Qualified Business Income (QBI) deductions- The implications of the SALT cap increase and how it affects high-income earners- Insights on Qualified Opportunity Zones and their effectiveness- And much more---------✅ 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.

Jun 6, 2025 • 10min
Should You Elect S-Corp? PTET, QBID, and Other Considerations
In this episode, I break down the benefits and drawbacks of S-Corps, including self-employment tax savings, the impact on retirement contributions, and the qualified business income deduction.Learn how your profit level can influence whether an S-Corp is the right choice for you, and discover the importance of calculating a reasonable salary.---------✅ 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.

May 30, 2025 • 16min
Equity Compensation Planning: ISOs, NSOs, RSUs
In this episode, I break down the ins and outs of Restricted Stock Units (RSUs), Non-Qualified Stock Options (NSOs), Incentive Stock Options (ISOs), or Employee Stock Purchase Plans (ESPPs).---------✅ 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.

May 23, 2025 • 13min
How Different Investments Are Taxed
In this week's episode, I dive deep into investment taxation and how it impacts your overall returns. Understanding how different investments are taxed is crucial if you're trying to maximize your portfolio's performance.Stocks: Learn about capital gains taxes, dividends, and the importance of holding periodsBonds: Discover the tax implications of corporate, treasury, and municipal bondsETFs and Mutual Funds: Understand the differences in tax treatment and why ETFs may be more favorableCryptocurrency: Get insights on capital gains, staking, and the unique aspects of crypto taxationREITs: Explore the tax inefficiencies of real estate investment trustsReal Estate: Learn about income tax, depreciation, and capital gains exclusions for primary residences---------✅ 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.

May 16, 2025 • 10min
Understanding Safe Harbor Taxes: Avoiding Penalties & The Standard Deduction
In this episode, I discuss how underpayment penalties can sneak up on you. Many of our clients come to us unaware of these penalties, thinking that their W-2 withholdings or year-end tax payments are enough. But there’s much more to it...---------✅ 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.

May 9, 2025 • 10min
HSA Plans & The Value of Investing the Funds
Many people don’t realize that HSAs can be invested, similar to a 401(k). This is especially beneficial for high-income earners who may have maxed out other tax-advantaged accounts.If you can avoid using the funds for medical expenses, the goal is to let your HSA grow as long as possible to take full advantage of its benefits.✅ Financial planning for 30-50 year old high-earners & 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.

May 2, 2025 • 13min
Mega Backdoor Roth 401(k): The Most Powerful Retirement Strategy You're Not Using
In this episode, I discuss the strategic timing for Roth conversions and how to maximize your contributions through the Mega Backdoor Roth 401(k).✅ Financial planning for 30-50 year old high-earners & 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.

Apr 25, 2025 • 14min
Asset Location & Strategies to Minimize Taxes with Investing
While many investors focus on asset allocation, understanding WHERE to place your investments can significantly impact your after-tax returns. This episode explains:The differences between tax-deferred, tax-free, and taxable accountsHow to minimize taxes and maximize your after-tax yieldThe best types of investments to hold in each account type, including bonds, REITs, and high-growth assets---------✅ 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.