The Stacking Benjamins Show

Episode: Spotting the Sharks: 5 Red Flags Your Financial Advisor Might Be Waving (SB1732)

Date: September 8, 2025
Hosts: Joe Saul-Sehy, OG, and Doug
Theme: How to spot red flags in financial advisors and avoid subpar advice

Episode Overview

This episode is a "Greatest Hits" selection, focusing on arming listeners with the tools and knowledge to assess their financial advisor's trustworthiness and quality. Joe and OG break down their "Top 5 Red Flags" to watch out for when working with (or selecting) a financial advisor, aiming to help listeners avoid common pitfalls and costly mistakes. The show weaves in humor, relatable anecdotes, and pop culture references, maintaining its signature light and friendly tone.

Key Discussion Points & Insights

[00:59] Context: The Market and Recap

• Joe explains the episode comes from August 2023, at a point when the stock market was booming but investor fear was high. He highlights the danger of jumping out of the market due to fear:

  "If you had jumped out of the stock market in 2023 in August, well, ...you would have lost out on a 44% rate of return in the S&P500 between that time and mid September of this year."
  — Joe [01:32]

• Emphasis on long-term investing and the cyclical nature of market fear.

[08:41] Headline: How Advisors Handle Clients Who Want to Speculate

• Discussion of an Investment News article about advisors managing bullish clients who want to chase hot stocks, IPOs, or crypto:
  • Some advisors maintain objectivity and keep client focus on goals and risk tolerance.
  • Many refuse to pick individual stocks for clients, outsourcing that to data-driven managers.
  • Advisors may allow "sandbox" or "fun money" accounts for speculation, but set clear boundaries (no "refills" if it tanks).

"If you don’t win big, which you probably won’t statistically, then you can’t go back to the safe money that’s for your long-term goals and ask for a refill."
— OG [13:51]

• The risk-reward on speculative accounts typically isn’t as significant as clients expect.

• Context of market cycles—recency bias can sway risk appetite.

  "Last year was like, oh, I’m gonna jump off a bridge...this year, woohoo, everything’s great!”
  — OG [16:28]

[24:19] Main Topic: Top 5 Financial Advisor Red Flags

General Theme/Lens

• Humility and client-centered focus are core indicators.
• The best advisors act like coordinators or agents, connecting clients to specialists when appropriate. "A great doctor surrounds themselves with great people."

The Top Five Advisor Red Flags

5. Affiliation with a Big Company (especially insurance) Over Independence

"Generally, big company makes me go...And by the way, if it’s a big insurance company, I go ‘mmm’ even harder."
— Joe [28:39]

• Not all big company advisors are bad, but independence may suggest higher commitment to the craft.
• Big company priorities can mean incentives misaligned with client interests.

4. Lack of Scheduled, Proactive Communication and Meeting Cadence

• Joe and OG quickly agree on the importance of knowing when and how often you’ll hear from your advisor.

"You should be able to look out on the horizon and see the tempo of when you’re expected to have some sort of communication."
— OG [37:46]

• The cadence sets clear expectations and accountability for both sides.

3. Office/Staff and Surroundings—Bad Vibe from Employees or Environment

• Joe describes how a messy front office, inattentive staff, or a boastful, intimidating advisor office layout are negative signs.

“If you go into their office and they’re playing Kramer yelling or, you know, power Lunch where they’re talking about all the hot stocks that day… I would turn around and run.”
— Joe [41:06]

• Bad staff usually reflects poor leadership and culture from the top.

3B. Compensation and Fees Are Opaque

• OG notes that while many focus on fee structure, the real red flag is when advisors can’t clearly explain how or what they charge.

“...People you’re working with should be able to easily articulate what they get paid for and how much it costs. Unabashedly.”
— OG [44:07]

• Value needs to be clear—what are you getting for what you pay?

2. Unexplained or Shady DISCLOSURES / Overuse of Jargon

• OG calls out undisclosed or poorly explained regulatory dings on BrokerCheck or the SEC website.

“If it’s not explainable easily, my spidey sense is tingling a little bit.”
— OG [50:48]

• Joe: Heavy use of jargon and "smoke & mirrors" is a red flag. Advisors should clarify and simplify, not hide info or make you feel dumb.

“The biggest BS artists were the ones that like to talk in big words and truly weren’t good.”
— Joe [53:38]

1. Leads with Products, Not Process/Planning

• Both make this their #1: If an advisor leads with a specific product (especially insurance), run. The process and your goals—NOT products—should be central.

“If somebody presents themselves as an advisor...and they lead the discussion around product and not process, you need to run.”
— Joe [55:47]

• Advisors should help clients "think about their thinking," not sell whatever pays most commission.

“The more that your advisor is focused on what do you want to do and how can I help you do ‘you’, the better off the relationship’s going to be.”
— OG [57:20]

Memorable Quotes & Moments

• On long-term investing:

  "We're always nervous about the market."
  — Joe [01:19]

• On advisor humility:

  “If the person you’re talking to is like, ‘Oh, no, no, I’ve got this big support group and it’s the big sign out front,’ I go, eh, really?”
  — OG [33:52]

• On clear fees:

  “Just tell it to me straight, man. How much is it per month? How much is it per year? How much is it on a percentage? Whatever your deal is, just hit me with it.”
  — OG [44:07]

• "A great advisor is like a sports agent: The client is the rock star, not the advisor."
  — Joe [36:13]

Timestamps for Important Segments

• [00:59] – Market analysis and jumping ship dangers
• [08:41] – Managing speculative clients and advisor objectivity
• [24:19] – Setting up the top five financial advisor red flags
• [28:39] – Red Flag 5: Big company vs. independence
• [37:46] – Red Flag 4: No proactive or scheduled communication
• [41:06] – Red Flag 3: Bad staff/office or intimidating environment
• [44:07] – Red Flag 3B: Fee explanations are not clear
• [50:48] – Red Flag 2: Shady disclosures, lack of transparency, use of jargon
• [55:47] – Red Flag 1: Advisor leads with product, not process
• [60:53] – Summary and "What Should We Have Learned Today?"

Notable Quotes (with Speaker and Timestamps)

• "The vast majority of people are good...And the same thing is true with advisors. The vast majority of them are."
  — OG [32:06]

• "If you don’t understand what the hell you’re doing, then it’s not great."
  — Joe [54:13]

• “You should be able to look out in the horizon and see the tempo of when you’re expected to have some sort of communication.”
  — OG [37:46]

• On the biggest red flag:

  "If someone presents themselves as an advisor...and they lead with product, not process, you need to run."
  — Joe [55:47]

Summary Conclusion

Joe and OG deliver practical guidance to help listeners avoid predatory or unhelpful financial advisors, stressing the critical importance of process, transparency, humility, and genuine client focus. Their candid anecdotes make the episode accessible and fun while providing concrete tools for vetting advisors. Their Top 5 checklist is a must-hear for anyone considering—or reconsidering—their financial advice relationships.

For more deep dives and resources, check the show notes at stackingbenjamins.com or subscribe to the "201" newsletter.