The Long Game

The Long Game

By Thomas KopelmanBusiness
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The Long Game episodes

  • How to Pay Off Debt in the Most Effective Way

    In this episode, I break down the difference between good debt and bad debt—such as what types of debt can actually work in your favor (like business loans and student loans for lucrative careers), versus credit card debt and loans for things you can't afford. Some highlights:

    • Credit Cards: My personal approach to using credit cards responsibly, including how I leverage rewards while avoiding high-interest debt
    • Debt Repayment Strategies: Exploring effective methods for paying off debt, including the Snowball and Avalanche methods, and how to choose the right one for your situation
    • Emergency Funds: Discover why having a small emergency fund can be a game-changer in your journey to becoming debt-free
    • 0% Financing: The pros and cons of 0% interest loans and how they can either be a helpful tool or a slippery slope, depending on your financial habits

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

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

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

    14 min
  • How to Manage Cash Flow When You're Paid In Equity or Bonuses

    In this episode, I walk through how to effectively manage your monthly income & expenses when you're paid in equity (or receive bonus income). Some highlights:

    Understanding RSUs: How they work, including vesting schedules and tax implications

    The Full Picture: Understanding your total income, expenses, and tax liabilities, so you can make smart decisions about your investments and savings

    Get actionable steps to manage your tax liabilities and ensure you’re not over-concentrated in company stock. Learn how to balance your cash flow and maximize your savings through 401(k)s, ESPPs, and HSAs.

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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.

    12 min
  • How to Manage Your Financial Life as a Married Couple

    Whether you’re newlyweds or have been together for years, navigating money matters can be challenging, especially when you start blending incomes, expenses, and financial goals.

    In this episode, I discuss three effective systems for managing finances in a marriage:

    1. Entirely Combined: The traditional approach where both partners share everything—income, expenses, savings, and investments. I share why this method often leads to stronger partnerships and better financial outcomes.

    2. Half and Half: A balanced approach where couples maintain a shared account for bills while also having individual accounts for personal spending. This method allows for autonomy while still working towards common financial goals.

    3. All Separate: While I don’t recommend this for everyone, I explore how some couples, especially those who marry later in life, find success in managing their finances separately.

    ---------

    ✅ 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.

    10 min
  • How Much Do I Need in an Emergency Fund?

    In this episode, I discuss why having cash on the sidelines is your best friend, especially in uncertain times. I also share a powerful quote from Morgan Housel that resonates with me: "More than I want big returns, I want to be financially unbreakable." This mindset is key to understanding the true value of an emergency fund. Some highlights from the episode:

    • The importance of having an emergency fund to avoid selling investments at a loss during market downturns
    • How much you should keep in your emergency fund based on your personal risk tolerance and life circumstances
    • Practical steps to determine the right amount for you, whether it's three months, six months, or even up to twelve months of expenses
    • Where to hold your emergency fund to maximize your returns without sacrificing liquidity

    ---------

    ✅ 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
  • How Much Do I Need To Invest To Be On Track For My Goals?

    In this episode, we talk about some of the complexities of preparing for retirement (or a work optional life), including:

    • The 4% rule and how it can guide your retirement spending

    • The importance of social security and what it might look like when you retire

    • Why relying solely on software for financial planning may not be the best approach

    • The significance of investing a percentage of your income and how it can set you up for success

    ----------

    ✅ 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
  • How to Manage Your Financial Life: Cash Flow Management, Surplus Planning, And The Importance Of Automation For Savings

    Many people struggle with their finances simply because they lack direction. I encourage you to sit down and think about your short-term, mid-term, and long-term goals. Trust me, once you clarify your objectives, managing your finances will become a lot easier.

    We also explore the four key metrics you need to understand to manage your cash flow effectively:

    1. Income: What you take home each month.

    2. Expenses: Most people underestimate their spending—are you one of them?

    3. Taxes: Understanding your tax liability is crucial, especially if you have complex income sources.

    4. Surplus: The amount left after accounting for income, expenses, and taxes.

    5. I break down how to nail down these numbers and why they are essential for creating a solid financial plan. Plus, I share my recommendations for budgeting strategies tailored to your income level, whether you’re a high-income earner or just starting out.

      ----------

      ✅ 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
    6. Best Retirement Accounts For Business Owners (2025)

      Too often, business owners reinvest every dollar back into their business. To help you understand the importance of retirement and the options available to you, this episode breaks down various retirement accounts, including:

      Solo 401k: My personal favorite! Learn how this account can maximize your contributions and provide incredible tax advantages.

      SEP IRA: Understand when this option might make sense and the limitations that come with it.

      Regular 401k: Discover how to set up a plan that benefits both you and your employees while avoiding compliance issues.

      Simple IRA: Is it really a good choice? I share my thoughts on why it may not be the best option for most business owners.

      Additionally, I touch on the differences between Roth and traditional IRAs, helping you make informed decisions about your tax strategy.

      ----------

      ✅ 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
    7. How to Plan For Your Taxes as a Business Owner

      Breaking down the differences between tax planning for W-2 employees and business owners while highlighting the complexities that come with owning a business. Some of the topics covered:


      - Understanding the difference between withholding and actual tax liability

      - The concept of safe harbor and how to avoid penalties
      - Strategies for planning your taxes effectively, whether you're a sole proprietor or in a partnership
      - The importance of projecting your business's financials throughout the year to avoid cash flow issues

      ----------

      ✅ 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.

      10 min
    8. Stop Using Your Business Like A Piggy Bank: How To Manage Cash Flow, How Much To Hold, And Where

      Many entrepreneurs start off by simply transferring money from their business to their personal accounts without a solid plan, leading to financial stress when income becomes irregular. In this episode you'll learn:

      - The importance of creating a "pay account" to manage your personal and business finances effectively.
      - Strategies for planning your living expenses and saving for lean months.
      - Key differences between operating as a sole proprietor versus an S-Corp, especially regarding tax planning and payroll.
      - How to avoid common pitfalls like underestimating your tax liabilities and incurring penalties.
      - The significance of building an emergency fund tailored to your business 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.

      14 min
    9. A New Chapter: What to Expect from The Long Game in 2025

      As we approach the end of the year, I want to express my gratitude to all of you who have been listening and supporting the podcast. With just under 200 episodes and over 75,000 downloads, it’s incredible to see how far we’ve come together.After a year of co-hosting with Jacob Turner, we’ve decided it’s best for him to pursue his own podcast. While I will continue to host the Long Game Podcast solo, I’m excited about the new direction it will take. Starting in January, I will focus on a structured approach to financial planning, diving into specific topics that I cover with my clients.The upcoming episodes will include discussions on business planning, hiring strategies, managing finances, and setting up retirement accounts. I’ll also explore essential components of a financial plan, such as cash management, debt, investing, and estate planning. Each episode will be concise, lasting between 10 to 20 minutes, making it easy for listeners to digest the information.----------✅ 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.

      9 min

    About The Long Game

    From the publisher's feed

    The Long Game podcast is all about educating 30-50 year old business owners and those with equity compensation on how to build wealth.

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