Podcast Summary: The Stacking Benjamins Show

Episode: 5 Signs Your Financial Advisor Might Be Failing You (SB1783)

Release Date: January 1, 2026
Hosts: Joe Saul-Sehy & OG
Theme: How to spot red flags with your financial advisor—with the signature mix of fun, banter, and accessible, practical finance talk Stacking Benjamins is known for.

Overview of Episode

The episode tackles a critical question for investors: How do you know if your financial advisor is truly acting in your best interests, or might actually be failing you? With a mix of entertaining banter and expert perspective, Joe and OG outline their top five red flags—drawing on both industry experience and listener questions. The episode also covers related topics like advisor incentives, due diligence, and proactive communication, all in the lighthearted “basement” style fans expect.

Key Discussion Points and Insights

1. Advisors and Speculative Investment Requests

Segment Start: 09:09

• Discussion opens with headlines about advisors dealing with clients who want to speculate or chase “hot” investments.
• Brandon Dixon James (Resilient Wealth Management): Maintains objectivity and focuses clients on goals, avoids individual stocks unless managed professionally.
• Greg Halter (Carnegie Investment Council): Allows “play money” accounts but doesn’t encourage speculation; expertise, not “throwing darts,” is why clients hire advisors.
• OG highlights the value of being a neutral voice: “When the pendulum swings one way too far, your advisor should be like, ‘Nah, it’s not as bad as you think—or as good as you think.’” (12:24)
• Importance of having separate "sandbox" or fun-money accounts and setting boundaries for them; don't expect “refills” if you lose money speculating.

2. Significance of Market Swings and Discipline

Segment: 16:22

• The S&P 500’s sizeable ups and downs illustrate emotional and financial risk if investors react too strongly to market turbulence.
• Selling at a downturn can mean missing out on recovery; wise advisors help clients avoid these emotional mistakes.

3. Top 5 Red Flags for Financial Advisors

Segment Starts: 24:25
Summary of Red Flags (below, with quotes and timestamps):

#5: Affiliation with Big (Especially Insurance) Companies

• Joe prefers independent advisors, as big firms may have conflicts of interest and prepackaged product pushes. But stresses that “the vast majority of people are good,” and there are great advisors everywhere (31:40).
• “If it’s a financial plan from a big insurance company advisor, you better believe insurance coverage will factor heavily into your plan.” (32:02)

#4: Lack of Proactive Meeting Cadence

• Both Joe and OG flag advisors who don’t set specific, proactive touchpoints.
• “You should be able to look on the horizon and see the tempo of when you’re expected to have some sort of communication… what’s the frequency of when I can count on you to be proactive?” – OG (37:36)

#3: Office Environment & Staff Vibe

• The atmosphere—how staff behave, what’s playing in the waiting room, the advisor’s physical setup—offers clues about professionalism and client focus.
• “If you go into their office, and they’re playing CNBC’s Power Lunch talking about hot stocks, I would turn around and run. A good financial plan should feel relaxing.” – Joe (41:17)
• Disrespectful or disengaged staff usually reflect poor leadership culture from the advisor.

#2: Opaqueness or Dodging on Fees and Disclosures

• Cost matters, but more important is transparency. Advisors should explain payment structure simply and directly, without “well, we get paid a couple different ways…”
• Memorable Moment: OG recounts frustration trying to get clear pricing in healthcare, tying it back to financial planning: “Just tell it to me straight, man. How much is it per month? How much is it per year?...Just hit me with it, right?” (44:41)
• Run from advisors who use jargon and can’t explain things clearly. “Their job is to make your life easier. If you don’t understand what you’re doing, it’s not a great fit.” – Joe (53:15)

#1: Leads with Product, Not Process

• The biggest red flag is when an advisor “presents as an advisor, but leads the discussion around product, not process.” – Joe (55:22)
• Example: If your early meetings are about what funds, insurance, or annuities to buy, not about your goals, run.
• “If you show up, say, I want to retire, and they immediately pivot to selling life insurance… that’s a red flag.” – OG (57:33)
• The advisor’s job: To focus first on the client’s life and goals, not sales. “Think about your thinking… our job is to help people think about how to think about things.” – OG (56:07)

Bonus Points:

• Do your due diligence. Check for complaints or disciplinary history on databases like BrokerCheck or the SEC’s website.
  • “Anything having to do with fraud or malfeasance with client funds—automatic, never pass go.” – OG (47:31)

Notable Quotes & Memorable Moments

• “Most people aren’t that foolish… you talk about taking 10% of your portfolio and going crazy, just realize you’re taking massive risk for potentially insignificant gain.” – OG (15:29)
• “It shouldn’t be about soothing the advisor’s ego—a financial plan should be about giving you peace of mind.” – Joe (41:17)
• On jargon: “All the biggest BS artists were the ones who talked in big words and truly weren’t good.” – Joe (53:15)
• “If your first 30 minutes is all about ‘tell me your money, here’s what’s wrong,’ instead of ‘tell me your goals,’ that’s a huge clue.” – OG (59:07)

Key Timestamps for Important Segments

• 09:09: Headlines – How advisors manage overly bullish clients and speculative requests.
• 24:25: Intro to the Red Flags segment and importance of having smart people in your corner.
• 27:43: #5 Red Flag – Bias toward large firms vs. independent advisors.
• 37:36: #4 Red Flag – The importance of a clear meeting schedule/cadence.
• 41:17: #3 Red Flag – Reading the office environment and staff.
• 43:14: #2 Red Flag – Clarity on compensation, fees, and transparency; importance of due diligence on disclosures.
• 55:22: #1 Red Flag – Advisor focusing on selling products over building a process tailored around your goals.

Tone & Takeaways

• Language & Tone: True to Stacking Benjamins’ signature style—friendly, conversational, packed with analogies, a few tangents, but always circling back to practical financial wisdom.
• Big Picture: The right advisor prioritizes your goals, communicates proactively, and is transparent and humble. Run from those who lead with product pitches, lack clarity, or don’t show sincere client-centeredness at every level.

Final Advice:

If your advisor focuses their “process” on pitching products, dodges hard questions about fees, or you feel like “just another account,” you’d be wise to seek better guidance.

“Our job as advisors is to help people think about how to think about things.” – OG (56:07)

For New Listeners

This episode delivers both laughs and actionable tips for anyone considering hiring—or firing—a financial advisor. Want more on this topic? Check out the episode’s show notes or subscribe to their 201 newsletter for deeper dives and links to helpful resources.