The Long Game

Thomas Kopelman
  • 4.7 (65)
  • 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. 6D AGO

    How Direct Indexing Works (and Why the Wealthy Use It) (with Ben Lake, CFA®, CFP®)

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

    23 min

  2. OCT 3

    I'm a Solo Business Owner Making $1 Million, How Do I Manage This & Lower My Tax Bill?

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

    12 min

  3. SEP 26

    From Corporate Life to Running Your Own Business (with Zach Ashburn, CFP®, EA, AFC®)

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

    38 min

  4. SEP 19

    Selling Your Business: Why ESOPs Might Be Your Best Option (ft. Wes Gray & Doug Pugliese)

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

    29 min

  5. SEP 12

    Managing Concentrated Stock Positions (with Ben Lake, CFA®, CFP®)

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

    30 min

  6. SEP 5

    Donating Private Assets to a Donor Advised Fund (with Brad Caswell)

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

    31 min

  7. AUG 29

    Stock vs Asset Sale: Considerations for Business Sale (with Chad Huebsch, EA, CTP)

    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 salesThe significance of goodwill in business transactionsPlanning strategies to maximize your after-tax proceedsThe hybrid 338(h)(10) election and its benefitsThe importance of having solid financials before selling------------- ✅ 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.

    22 min

  8. AUG 22

    Financial Planning from 30-50 Years Old: Key Decisions to Get Right

    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 creepMaking informed housing decisions in today's marketBalancing family responsibilities while planning for the futureThe importance of education funding and estate planningStrategies for effective investment and risk management ------------- ✅ 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.

    24 min
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4.7
out of 5
65 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
    219
  • Rating
    Clean
  • Copyright
    © Thomas Kopelman
  • Show Website
    The Long Game

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