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Thomas Kopelman · Investment

The Long Game

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.

Episodes

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How to Withdraw from Your Portfolio in Retirement (+ Common Misconceptions)

05 Jun 2026
27m
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Biggest Financial Regrets of the Wealthy (w/ Ben Lake)

29 May 2026
28m
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How to Manage Salary & Distributions in Your S Corp

22 May 2026
17m
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Planning for an IPO: 8 Things to Think About

15 May 2026
38m
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What It’s Actually Like Working with a Financial Advisor (Step-by-Step)

08 May 2026
12m
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The Value of Hiring Coaches (with Dave McGhee)

01 May 2026
30m
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Does More Money Make You Happier?

24 Apr 2026
10m
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Short Term Rentals: Tax Benefits & How To Find Good Investments (with Arda Bircan)

17 Apr 2026
24m
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Short-term rentals offer high-income professionals a powerful tax-saving mechanism by allowing paper losses from depreciation to offset active income, including W-2 wages and RSU proceeds. By ensuring average guest stays are seven days or less, investors can treat these properties as active businesses rather than passi...

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How to Review Your Tax Return (with Ryan Dolan)

10 Apr 2026
17m
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How to Plan for Safe Harbor if Your Tax Return is on Extension

03 Apr 2026
10m
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You Set Up a Trust… Now What? (with Blake McKibbin, JD, ChFC®, CLU®)

27 Mar 2026
21m
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Signs You're Living a Financially Healthy Life

20 Mar 2026
15m
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How to Do Your Annual Financial Review (Step-by-Step)

13 Mar 2026
11m
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Managing a Concentrated Position: 351 Exchanges & Other Tools (w/ Brent Sullivan

06 Mar 2026
24m
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Understanding Irrevocable Life Insurance Trusts (ILITS)

27 Feb 2026
16m
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Buying vs. Building a Business (with David Barnett)

20 Feb 2026
39m
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Private Investments (When & Where They Fit in a Portfolio) with Ben Lake, CFA®, CFP®

13 Feb 2026
32m
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Ins & Outs of Long Short Direct Indexing

06 Feb 2026
26m
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6 Ways to Get Liquidity in Your Financial Life (with Ben Lake, CFA®, CFP®)

30 Jan 2026
28m
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Unexpected financial needs often require immediate liquidity, necessitating a strategic approach to balance short-term cash flow with long-term portfolio health. Rather than relying on simple asset liquidation, which can trigger significant tax liabilities, individuals should evaluate a hierarchy of options starting wi...

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How To Prepare To Get Your Taxes Done Smoothly and Efficiently (with Ryan Dolan, EA)

23 Jan 2026
17m
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