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, includi...
Mar 07, 2025•14 min
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 ...
Feb 28, 2025•11 min
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: 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. Half and Half : ...
Feb 21, 2025•10 min
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 you...
Feb 14, 2025•11 min
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 entr...
Feb 07, 2025•11 min
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: Income : What you take home each month. Expenses : Most people underestimate their spending—are you one of them? Taxes : Understanding your ...
Jan 31, 2025•11 min
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 be...
Jan 24, 2025•12 min
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 ...
Jan 17, 2025•10 min
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 plann...
Jan 10, 2025•13 min
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 structur...
Dec 27, 2024•8 min
In this episode, we dive deep into the lessons learned from working with business owners and the unique financial perspectives that come from their experiences. The Unique Perspectives on Money: We talk about how different business owners view money and success, and why there’s no one-size-fits-all approach to personal finance. The Value of Service Businesses: Why running a service-based business can be a fantastic choice for aspiring entrepreneurs, highlighting the benefits of cash flow and sca...
Dec 20, 2024•22 min
Building on our previous discussions about estate tax planning and donor advised funds, we explore a variety of charitable giving tools, their benefits, and when they make sense for you. Episode Highlights: -The impact of recent tax law changes on charitable giving -Understanding donor advised funds and their advantages -The differences between donor advised funds and private foundations -How to effectively bunch charitable gifts for maximum tax benefits -The role of charitable remainder trusts ...
Dec 13, 2024•31 min
Blake shares his insights on why SLATs are often viewed as the go-to tool for estate tax planning, but also highlights the important considerations and potential downsides that many overlook. From the irrevocable nature of these trusts to the implications of divorce and early death, this episode dives deep into the complexities of estate planning for high net worth individuals. Key topics include: -What a SLAT is and how it works -The benefits and risks associated with SLATs -The importance of f...
Dec 06, 2024•26 min
In this episode, we dive deep with Daniel Crosby (author of The Soul of Wealth) into the multifaceted relationship between wealth, happiness, and fulfillment. Here are three key takeaways that I believe will resonate with many of you: Wealth is Not Just a Number 💰 Daniel shares a powerful story about Alexander the Great, illustrating that despite his immense wealth and power, he was ultimately undone by personal loss. This serves as a reminder that true wealth encompasses more than just financi...
Nov 22, 2024•1 hr 5 min
As the year comes to a close, it's crucial to take proactive steps to optimize your tax situation. Join us as we discuss: The importance of knowing your numbers and understanding your financial situation Maximizing the Qualified Business Income (QBI) deduction Utilizing retirement accounts effectively, including 401(k)s and Roth options The benefits of donor-advised funds for charitable giving Strategies for tax loss harvesting and investment portfolio reviews The significance of Health Savings ...
Nov 15, 2024•29 min
After wrapping up a comprehensive insurance series, Thomas and Jacob shift gears to discuss the often-overlooked aspects of tax planning. They explain what QBI is, who it applies to, and why it's crucial for business owners to understand and plan around it. Key topics: What is the Qualified Business Income Deduction? Who qualifies for QBID and how it can impact your taxes The importance of proactive tax planning and communication with your financial team Strategies for maximizing your QBID, incl...
Nov 08, 2024•20 min
In this episode, we're joined by Broc Buckles as we break down the essentials of disability insurance, discussing its importance, the different types available, and how it can serve as a crucial safety net for your income. We explore group vs. individual policies, the significance of definitions like "own occupation," and the various riders that can enhance your coverage. Whether you're a financial advisor looking to expand your knowledge or someone seeking to understand how disability insurance...
Nov 01, 2024•21 min
In this episode, hosts Thomas Kopelman and Jacob Turner are joined by returning guest Broc Buckles, an expert in the insurance space. Together, they dive deep into the world of life insurance, breaking down the different types, including term and permanent insurance, and discussing when and why you might need them. Key Topics Covered: Overview of life insurance: term vs. permanent How to determine how much life insurance you need The importance of reevaluating your life insurance needs during ma...
Oct 25, 2024•36 min
In this episode of the Long Game podcast, Thomas Kopelman and Jacob Turner dive into the often-overlooked topic of umbrella insurance coverage. Aimed primarily at high net worth individuals and those on their way, the discussion highlights the critical importance of understanding this type of insurance and how it can serve as a safety net in the face of unforeseen circumstances. Here are three key takeaways from this episode that you won't want to miss: What is Umbrella Insurance and Why You Nee...
Oct 18, 2024•12 min
In this episode, co-hosts Thomas Kopelman and Jacob Turner dive deep into the world of homeowners insurance, especially for high-income and high-net-worth individuals. With recent events like hurricanes affecting many, understanding the nuances of homeowners insurance has never been more critical. Thomas and Jacob discuss the importance of having the right coverage, what to look for in your policy, and how to avoid common pitfalls that could leave you underinsured. Key topics covered in this epi...
Oct 11, 2024•21 min
Most high net worth people think insurance is less important for them, but that could not be further from the truth. Insurance is so important for high net worth people but the way you structure policies is very different. This is part 1 of an insurance series where we go over auto, what to look out for, what you want in your policy, etc.
Oct 04, 2024•23 min
In this episode with Callie Cox, we talk about the recent FED rate cut and what it means for you. We then go into tilts we have in our portfolios, what we think about the markets over the next couple years, and much more as it relates to investing.
Sep 27, 2024•45 min
This is part 2 of a series of estate planning for business owners. In this episode with Dave Haughton, we use an example and plan for a business owner who will be over the estate tax exmeption. We think about structures like: - family limited partnerships - charitable remainder trusts - SLATs - Dynasty trusts - trusts in various states And talk through what each of these are and the benefit they can have....
Sep 20, 2024•34 min
Estate planning is important for everyone. But even more important for business owners. If you were no longer able to make decisions for your business, what would happen? If you answered you have a POA or you don't know, then you need to get on this ASAP. In this episode, we have Dave Haughton on to talk about: - Trusts vs wills - Why most business owners need trusts -Why POAs are not enough - Real estate holdings and the need for LLCs And much more!...
Sep 13, 2024•28 min
It's no secret that interest rate changes are coming. With that comes a lot of good like lower mortgages and cheaper borrowing on other loans. But is also means lower rates on cash, bonds, etc. In this episode we go talk about what is happening and what it means for you. We talk about refinancing, recasting, what you should do with your cash, etc.
Sep 06, 2024•19 min
Real estate is something almost everyone wants to invest in. Why? Because of 'passive income'. But is real estate really that passive? Or is it as easy as people make it out to be? In this episode with Raj Tut, we talk: - his journey with investing in real estate - how you have to view it like a business - mistakes others make (and one's he has made) - what to look for when investing in a fund
Aug 30, 2024•29 min
For high income earners, deferring taxes to the future can be a great move. But you are oftentimes limited to the $69,000 you can put into a 401(k). This is where cash balance plans come into play. You can potentially defer hundreds of thousands more using this tool. In this episode with Ben Lake, we talk all things cash balance plans, how they work, the good, the bad, etc.
Aug 23, 2024•37 min
As you get further along in your financial journey, the decisions you make have HUGE impacts. Many turn to friends, family members, peers, etc for advice. The problem... it is not tailored to you. It's what has worked well for them and they are telling you about it. This can be dangerous. And it's a huge reason why having a planner who knows you, your goals, your values, your fears, and your situation is so valuable.
Aug 16, 2024•21 min
HSA's and FSA's are both great accounts. They allow you to save for health expenses on a pre-tax basis. In this episode we walk through: - what an HSA is - what an FSA is - what health plans allow for each - how most use FSA's incorrectly
Aug 09, 2024•19 min
This is a question that comes up time and time again. Many believe that the party of the president matters. They assume the markets do better with republicans and worse with democrats. But is this true? We dive into the data to explore this further.
Aug 02, 2024•19 min
