Top Episodes of The Long Game in 2025

As we wrap up 2025, I’ve been thinking about how much The Long Game community has grown and how many meaningful conversations we’ve shared.

This podcast started as a way to help people make smarter decisions about money & life and seeing thousands of you tune in, learn, and apply these ideas has been one of the highlights of my year.

So today, I wanted to look back and highlight the most listened-to episodes of the year:

How to Manage Your Financial Life: Cash Flow and the Importance of Automation (691 listens)

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 tax liability is crucial, especially if you have complex income sources.
• Surplus: The amount left after accounting for income, expenses, and taxes

​Spotify​ → ​Apple Podcasts​ →

How Direct Indexing Works (and Why the Wealthy Use It) (with Ben Lake, CFA®, CFP®) (702 listens)

In this episode, we break down direct indexing and long/short direct indexing, two powerful (and often misunderstood) tax strategies for high-income earners, business owners, and those with concentrated stock positions. We talk about:

• The difference between ETFs, mutual funds, and direct indexing
• How direct indexing helps you harvest tax losses while tracking an index
• Who direct indexing makes sense for (and who should skip it)
• When to switch from standard direct indexing to a long/short strategy
• Real-world scenarios where direct indexing can create massive tax savings

​Spotify​ → ​Apple Podcasts​ →

IULs: How They're Incorrectly Sold & Used (with Robert Rikard) (734 listens)

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.

​Spotify​ → ​Apple Podcasts​ →

Tax Strategies for $1M to $10M SMB Owners (with Chad Huebsch, EA, CTP) (830 listens)

In this episode, I'm joined by Chad Huebsch from Blueprint Tax to break down the importance of tax planning for business owners doing $1 million to $10 million. Chad shares valuable insights on entity selection, including the pros and cons of sole proprietorships, S-corporations, partnerships, and C-corporations.

​Spotify​ → ​Apple Podcasts​ →

Growth Tips for Financial Advisors (841 listens)

In this episode, I sit down with my friend and fellow advisor, Mark Cecchini, to talk about what it takes to build a modern advisory career. We have similar practices today, but got here in completely different ways, so we walk through both paths and what we would do if we were starting over. Some highlights:

• Understanding your role as an advisor (whether as a lead advisor or a background planner)
• Finding your niche and how it can impact your business
• Strategies for building a personal brand & leveraging social media to attract clients
• The challenges of client relationships and the importance of knowing when to part ways
• Developing a successful client onboarding process

​Spotify​ → ​Apple Podcasts​ →

Mega Backdoor Roth 401(k): The Most Powerful Retirement Strategy You're Not Using (874 listens)

In this episode, I discuss the strategic timing for Roth conversions and how to maximize your contributions through the Mega Backdoor Roth 401(k).

​Spotify​ → ​Apple Podcasts​ →

Big Beautiful Bill Summarized: Tax Cuts, Tips, SALT Caps, PTET, and More (890 listens)

In this episode, I’m joined by tax expert Roger Ledbetter to break down the recent tax bill. We talk about the new rules and discuss its potential impact on both individuals and businesses. Some highlights:

• Changes to individual tax rates and deductions, including the standard deduction and child tax credit
• The implications of the bill for business owners, including QBI and bonus depreciation
• New deductions for tips, overtime, and car loan interest
• Insights on Opportunity Zones and Qualified Small Business Stock (QSBS)

​Spotify​ → ​Apple Podcasts​ →

Financial Planning from 30-50 Years Old: Key Decisions to Get Right (986 listens)

In this episode, Mark Cecchini and I 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 creep
• Making informed housing decisions in today's market
• Balancing family responsibilities while planning for the future
• The importance of education funding and estate planning
• Strategies for effective investment and risk management

​Spotify​ → ​Apple Podcasts​ →

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