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Artwork for The Long Game

The Long Game

Thomas Kopelman
Real Estate
Retirement Planning
Wealth Management
Money
Property Taxes
Financial Planning
Transaction Costs
Home Ownership
Equity
Cash Flow
Financial Advice
Housing Market
Tax Planning
Wealth
Long-Term Care Planning
Personal Finance
Insurance
Maintenance Costs
Mortgage
Investment

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.

PublishesWeeklyEpisodes238Founded5 years ago
Number of ListenersCategory
Business

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Artwork for The Long Game

Latest Episodes

In this episode, I walk through the exact framework we use with clients for their annual financial review. If you sit down once a year and go through these steps, you’ll have a much better understanding of where you are financially and where you’re g... more

In this episode, I’m joined again by Brent Sullivan to break down a strategy most investors have never heard of, but that can be incredibly powerful for the right situation: 351 exchanges

If you’ve built significant wealth in a single stock, you’ve ... more

In this episode, Ben Lake, CFA®, CFP® and I break down ILITs, Irrevocable Life Insurance Trusts, and why they matter for high net worth families. At a 40% federal rate above the exemption, that can mean writing a check for tens of millions of dollars... more

I’ve built businesses. I work with business owners every day. And I’ve watched a lot of people romanticize buying one.

So I wanted to have an honest conversation about it.

David Barnett has helped people buy and sell dozens of companies, and he’s s... more

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Recent Guests

Brent Sullivan
Tax/Investment expert discussed on 351 exchanges and wealth planning
TaxAlpha Insider
Episode: Managing a Concentrated Position: 351 Exchanges & Other Tools (w/ Brent Sullivan
David Barnett
Lifelong entrepreneur and small business consultant specializing in business acquisitions.
Episode: Buying vs. Building a Business (with David Barnett)
Cody Garrett
Financial Planner and Author
Episode: Roth vs. Traditional with Cody Garrett, CFP®
Colin Stroud
Founder of Go Somewhere
Go Somewhere
Episode: Maximizing Credit Card Points (with Colin Stroud)
Zach Ashburn
Financial advisor and co-founder of Reach Strategic Wealth
Reach Strategic Wealth
Episode: From Corporate Life to Running Your Own Business (with Zach Ashburn, CFP®, EA, AFC®)
Wes Gray
Co-founder of Alpha Architect, with expertise in ESOPs and investment strategies.
Alpha Architect
Episode: Selling Your Business: Why ESOPs Might Be Your Best Option (ft. Wes Gray & Doug Pugliese)
Doug Pugliese
Expert on 1042 Qualified Replacement Properties, focusing on ESOPs for business sales.
Alpha Architect
Episode: Selling Your Business: Why ESOPs Might Be Your Best Option (ft. Wes Gray & Doug Pugliese)
Brad Caswell
Former Chief Operating Officer of Vanguard Charitable and consultant in the DAF space
Charitable Solutions
Episode: Donating Private Assets to a Donor Advised Fund (with Brad Caswell)
Chad Huebsch
Financial advisor and expert on business sales and tax strategies
Episode: Stock vs Asset Sale: Considerations for Business Sale (with Chad Huebsch, EA, CTP)

Host

Thomas Kopelman
Host and principal organizer focusing on holistic financial planning and wealth-building strategies.

Reviews

4.8 out of 5 stars from 110 ratings
  • Brand New Listener

    Just discovering your content for the first time. Starting from the beginning and loving it. Things have changed so much since 2020-21 but your early content is still so relevant and helpful. I’m sharing with family and friends.

    Apple Podcasts
    5
    MedficaJay
    United States5 months ago
  • Loving the solo episodes

    Loving the solo episodes, they must be so much harder to pull off. Keep it up!

    Ben E.

    Apple Podcasts
    5
    95Ben
    United Statesa year ago
  • Phenomenal!

    As a growing financial consultant, I can honestly say that this podcast has been nothing short of fruitful. The insight that I’ve been able to capture from your conversations have allowed me to help my clients understand the complexities of financial planning at a basic level. Thank you guys so much for this content!

    Apple Podcasts
    5
    Khalif M, Philadelphia
    United Statesa year ago
  • Thank you

    Thomas, you are doing great work! It’s helpful not only to your potential clients but to fellow advisors like me)

    Apple Podcasts
    5
    Lyubomyr 1982
    United States2 years ago
  • Very informative

    Thomas’s approach to planning is very refreshing and every episode offers a lot of great advice. I look forward to each new episode.

    Apple Podcasts
    5
    Bokke1221
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Clear, accessible explanations of complex planning concepts.
Consistently valuable for young professionals seeking a sustainable financial path.
Thoughtful, actionable financial advice that listeners can apply today.
High-quality guests and practical takeaways across topics.

Talking Points

Recent interactions between the hosts and their guests.

Managing a Concentrated Position: 351 Exchanges & Other Tools (w/ Brent Sullivan
Q: What are the practical limits or thresholds for someone to consider using 351 exchanges?
The toolkit is typically geared toward larger positions, but sponsors are increasingly accepting smaller contributions (e.g., $150k–$250k) depending on the sponsor's capabilities; the key limits are the 25% per issuer and top five under 50% diversification rules at launch, plus ongoing risk and governance considerations.
Managing a Concentrated Position: 351 Exchanges & Other Tools (w/ Brent Sullivan
Q: Brent, what exactly is a 351 exchange and what problem is it solving for concentrated stock holders?
A 351 exchange is a mechanism that allows contributing assets into a new ETF without triggering immediate tax recognition, provided diversification tests are met; it's increasingly used to seed ETFs with in-kind contributions so investors can diversify their concentrated positions while deferring taxes.
From Corporate Life to Running Your Own Business (with Zach Ashburn, CFP®, EA, AFC®)
Q: How do you think about financial planning for those who know they need to start their own company?
We develop a stoplight plan to guide individuals through the stages of financial readiness based on their income replacement from consulting or other avenues.
From Corporate Life to Running Your Own Business (with Zach Ashburn, CFP®, EA, AFC®)
Q: What do you think are the triggers for people who want to make this choice?
It's often a combination of life events and unexpected consulting offers that trigger people to consider starting their own business.
Selling Your Business: Why ESOPs Might Be Your Best Option (ft. Wes Gray & Doug Pugliese)
Q: What are the benefits of an ESOP compared to traditional selling methods?
Benefits include tax deductions for the company, avoidance of capital gains taxes for the owner, and fostering a culture of ownership among employees, which can enhance loyalty and productivity.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About The Long Game

What is The Long Game about and what kind of topics does it cover?

This program focuses on building wealth for business owners and high-earning individuals by translating complex financial concepts into practical steps. Across episodes, listeners encounter deep dives into estate planning, tax strategies, private investments, real estate, and career-finance freedom. Frequent guests include seasoned financial professionals and entrepreneurs who share actionable tactics—from funding ILITs and navigating Q4 tax planning to leveraging private equity and maximizing travel rewards—designed to help listeners optimize cash flow, retirement readiness, and lifestyle choices. A standout aspect is the blend of rigorous planning with real-world anecdotes, making sophisticated strategies more approachable for those balan... more

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Which podcasts are similar to The Long Game?

These podcasts share a similar audience with The Long Game:

1. The Compound and Friends
2. ChooseFI
3. Your Money, Your Wealth
4. The Rational Reminder Podcast
5. All-In with Chamath, Jason, Sacks & Friedberg

How many episodes of The Long Game are there?

The Long Game launched 5 years ago and published 238 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on The Long Game?

Recent guests on The Long Game include:

1. Brent Sullivan
2. David Barnett
3. Cody Garrett
4. Colin Stroud
5. Zach Ashburn
6. Wes Gray
7. Doug Pugliese
8. Brad Caswell

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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