

The Long Game
Thomas Kopelman
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.
You will learn everything from the basics to complex tax, estate, and financial planning concepts from Thomas Kopelman as well as other qualified professionals.
Episodes
Mentioned books

Aug 22, 2025 • 24min
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.comDisclaimer: None of this should be seen as financial advice. It is just for informational purposes.

Aug 15, 2025 • 34min
IULs: How They're Incorrectly Sold & Used (with Robert Rikard)
In this episode, I'm joined by Robert Rikard, a lawyer and partner at the Investor Loss Center, to discuss the controversial world of Index Universal Life (IUL) insurance. With the rise of social media influencers promoting IULs, many people are confused and misinformed about these products.He explains how many agents misrepresent these products, often targeting middle America with unrealistic promises of tax-free retirement income. Some highlights from the episode:The rise of IULs and the misinformation surrounding themThe commission structure that incentivizes agents to sell IULsReal-life case studies of clients who have suffered significant lossesAlternatives to IULs that may be more suitable for average investorsWebsite: https://www.investorlosscenter.comLinkedIn-------------✅ 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.

Aug 8, 2025 • 27min
SBA Loans Explained (with Matthias Smith)
In this episode, I sit down with Matthias Smith (founder and owner of Pioneer Capital Advisory) a brokerage firm specializing in SBA loans. We talk about:- The different types of loans available for purchasing a business- What an SBA loan is and how it works- The importance of personal guarantees and life insurance in the loan process- Common misconceptions about SBA loans- Tips for prospective business buyers on preparing for the loan processConnect with Matthias:Email – matthias@pioneercap.comLinkedIn – Matthias SmithTwitter – @SBA_Matthias-------✅ 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.

Aug 1, 2025 • 31min
Planning for an IPO (with Mark Cecchini, CFP®)
In this episode, I'm joined by Mark Cecchini, CFP® to discuss the intricacies of planning for an IPO. As the window opens up again, many employees are facing similar situations. We dive deep into the essential steps for preparing for an IPO, including:Understanding the difference between single-trigger and double-trigger RSUsThe importance of having a solid financial plan and clear goalsStrategies for managing equity concentration and diversificationTax planning considerations before and after an IPOThe significance of Qualified Small Business Stock (QSBS) eligibility--------✅ 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.

Jul 25, 2025 • 15min
Answering Listener-Submitted Questions
Curious about retirement accounts? Dive into the differences between Roth and traditional IRAs and learn why solo 401(k)s might win over SEP IRAs for entrepreneurs. Discover savvy tax reduction strategies for W-2 employees and weigh the decision of paying off that mortgage versus investing. The conversation emphasizes a long-term view on finances, helping you balance emotional choices with logical financial strategies.

11 snips
Jul 18, 2025 • 43min
Tax Strategies for $1M to $10M SMB Owners (with Chad Huebsch, EA, CTP)
In this insightful discussion, tax advisor Chad Huebsch from Blueprint Tax shares expert strategies tailored for business owners earning between $1 million and $10 million. He breaks down the pros and cons of different business entities, emphasizing the advantages of S-corporations over sole proprietorships. Chad also explores the intricacies of the Pass-Through Entity Tax and Qualified Business Income deductions. Additionally, he provides valuable insights on retirement planning and the benefits of hiring family members to optimize tax situations.

Jul 11, 2025 • 50min
Big Beautiful Bill Summarized: Tax Cuts, Tips, SALT Caps, PTET, and More
In this discussion, tax expert Roger Ledbetter shares his deep knowledge of the recent tax bill and its effects on individuals and businesses. He simplifies complex topics like new individual tax rates, significant deductions for tips and car loans, and the implications for Opportunity Zones. Listen as he reveals the latest changes around gambling losses and estate exemptions, while also outlining the strategic advantages of Qualified Small Business Stock. Roger's practical insights make navigating the evolving tax landscape feel more manageable!

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.


