The Long Game

Thomas Kopelman
  • 4.7 (67)
  • BUSINESS
  • UPDATED WEEKLY

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.

  1. 12/19/2025

    Roth vs. Traditional with Cody Garrett, CFP®

    In this episode, we break down how to effectively manage your lifetime taxes & how they effect your investment decisions. Cody shares insights from his recent book, "Tax Planning to and Through Early Retirement," which has already sold over 8,000 copies. Some highlights: - Understanding your income sources in retirement - The impact of tax rates on your financial decisions - Strategies for maximizing tax efficiency through Roth conversions and traditional contributions - Real-life examples of clients navigating their retirement planning ---- ✅ 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.

    42 min

  2. 12/12/2025

    I'm About to Have a Child, What Do I Need to Plan For Financially?

    In this episode, I cover key steps to make sure you’re financially prepared for the journey ahead. Some takeaways: Update Your Life Insurance: Why having proper life insurance is essential once you have a child and how to determine the right amount for your family Health Insurance for Your Newborn: The process of adding your baby to your health insurance plan and why it’s important to do this sooner than later Creating an Estate Plan: Protect your family’s future and ensure your wishes are honored Budgeting for Baby Expenses: How to adjust your budget to accommodate new expenses, including daycare and one-time costs for nursery essentials Leveraging Dependent Care FSA: How to take advantage of pre-tax benefits for childcare expenses, which can save you money in the long run Planning for Your Child’s Future: Various options for saving for your child’s education, including the benefits of 529 plans ---- ✅ 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.

    11 min

  3. 12/05/2025

    Growth Tips for Financial Advisors + Our Stories in the Industry (with Mark Cecchini, CFP®)

    In this episode, I sit down with my friend and fellow advisor, Mark Cecchini, to talk about what it takes to build a modern advisory career. We have similar practices today, but got here in completely different ways, so we walk through both paths and what we would do if we were starting over. Some highlights: Understanding your role as an advisor (whether as a lead advisor or a background planner)Finding your niche and how it can impact your businessStrategies for building a personal brand & leveraging social media to attract clientsThe challenges of client relationships and the importance of knowing when to part waysDeveloping a successful client onboarding process---- ✅ 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.

    53 min

  4. 11/21/2025

    Moving to Puerto Rico & the Tax Benefits (with Wes Gray)

    In this episode, I sit down with Wes Gray to break down one of the most powerful and misunderstood tax strategies available moving to Puerto Rico under Act 60. Wes has lived there for years, so you’ll hear the real story behind the numbers, the rules, and the lifestyle. What we cover: What bona fide residency actually requiresHow 0% capital gains treatment is appliedWhen the 4% business tax can make senseLifestyle factors people forget to considerHow to evaluate whether the move fits your situationWhy this strategy is not for everyone---- ✅ 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.

    26 min

  5. 11/14/2025

    End-of-Year Tax Moves to Save Thousands

    Most people neglect their taxes until it's too late, leaving money on the table. In this episode, I share strategies for managing your taxes before April, including: Understanding your projected income and quarterly paymentsMaximizing contributions to 401(k)s, HSAs, and 529 plansUtilizing tax loss harvesting and Roth conversionsThe impact of charitable giving and new AGI rulesReviewing your business entity structure for optimal tax benefits---- ✅ 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.

    13 min

  6. 11/07/2025

    How to Use Real Estate to Lower Your Taxes: Passive vs. Active Tax Treatment

    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 treatmentWhen real estate losses can (and can’t) offset your W-2 or business incomeHow depreciation, bonus depreciation, and cost segregation workWhy short-term rentals can be a powerful (but tricky) tax playThe truth about depreciation recapture and what to plan forHow to time real estate investments in high-income years to legally save thousands---- ✅ 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.

    35 min

  7. 10/31/2025

    Maximizing Credit Card Points (with Colin Stroud)

    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 incomesThe Basics of Earning Points: The benefits of cash back cards vs travel rewards cardsRedemption Strategies: How to leverage your points effectively, including tips on transferring points to airline and hotel partners for maximum valueThe Two-Card System: A simple two-card strategy that allows you to optimize your spending without overwhelming complexity------ ✅ 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.

    31 min

  8. 10/24/2025

    How to Read Your Paystub

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

    11 min
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4.7
out of 5
67 Ratings

About

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.

Information

  • Creator
    Thomas Kopelman
  • Years Active
    2020 - 2025
  • Episodes
    228
  • Rating
    Clean
  • Copyright
    © Thomas Kopelman
  • Show Website
    The Long Game

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