The Stacking Benjamins Show

Episode: Waste Time on Hot Real Estate or IPO Trends or Start Building Wealth? (SB1786)

Date: January 5, 2026

Hosts: Joe Saul-Sehy, OG, and Doug
Theme: “2026: New Year, Old Rules – Ignore the Hype, Build Real Wealth”

Episode Overview

The Stacking Benjamins crew rings in the new year by debunking popular financial fads like hot IPOs and “engineered” real estate schemes, reminding listeners that building wealth isn’t about chasing trends—but sticking to time-tested principles. Joe, OG, and Doug use real-life examples, personal stories, and their signature humor to show why the “old rules” of investing still rule.

Key Discussion Points & Insights

1. The Year Changes, The Rules Don’t

Time Stamp: 05:25 – 07:06

• Joe emphasizes that while “it’s a shiny new 12 months,” the basic tenets of money management aren’t fundamentally different in 2026 than they were in years past.
• Quote:

  "The theme today is it's a new year, but the old rules still apply...the same rules can apply in 2026 that applied in 2025 and before." — Joe (05:25)

2. Spotlighting IPO Scams and Penny Stock Pitfalls

Time Stamp: 09:05 – 16:30

• The hosts dissect a Wall Street Journal piece on a wave of IPO scams, where "emerging growth companies" exploited loosened regulations, leading to many penny-stock suspensions.
• OG compares playing the penny stock game to gambling:

  "If I put five grand into a slot machine or five grand into a penny stock, you know, I probably have the same outcome potential." — OG (12:14)

• Joe shares an anecdote about an investor who, by buying so much of a penny stock, inadvertently became a “majority owner”—but only because no one else wanted the stock.
• The dangers of “get rich quick” thinking, with Joe highlighting how “penny stocks trade for a nickel for a reason.”

3. Why “Invest Like the 1%” Is Misleading Hype

Time Stamp: 20:16 – 26:11

• The downfall of platforms like Yieldstreet and deceptive marketing from companies like Fundrise is discussed (“engineered for superior results”).
• OG calls out the illusion of exclusive returns:

  "There is no way to have stock returns without stock volatility. It doesn't exist...If there was a better thing than stocks, the universe would do that." — OG (25:04)

• They warn that “invest like the 1%” is just clever phrasing to lure in everyday investors.

4. Parallels Between Markets and Gambling

Time Stamp: 26:51 – 29:26

• Playing the odds in IPOs or speculative investments is equated to assembling an unlikely parlay in a gambling app.
• OG:

  "That's the same thing, Joe, as what you're talking about in terms of volatility, standard deviation...you can build out that bet. What do you think the math wizards at DraftKings have figured out..." (27:58)

• The real winners are often just lucky outliers.

5. Real Estate Realities: What Hot Platforms Don’t Tell You

Time Stamp: 20:16 – 24:01; 38:18 – 42:50

• Joe and OG recall their early warnings about alternative real estate platforms and review the deceptive promises (“invest like the 1%”) that left many investors with massive losses.
• The TikTok Minute (39:53) features vital advice for first-time homebuyers:
  • Don’t trust the seller’s property tax bill; when ownership changes, property taxes can spike due to assessment "uncapping."
  • OG highlights state-specific rules and why being informed saves money and heartache.

6. Building Wealth: What Actually Works

Time Stamp: 44:18 – 60:06

• Diversification, time in the market, and realistic expectations are key.
• OG’s analogy:

  “You have a luck bucket and an experience bucket, and your goal is to fill up your experience bucket before you run out of your luck bucket.” (44:18)

• The hosts stress that chasing wild risk due to “FOMO” (fear of missing out) won’t work in the long run; the power of compounding wins.
• Joe:

  “A lot of people listen to shows like ours because they want to find ways to get rich more quickly. And you are eliminating some of that serendipity in order to get some more certainty.” (47:09)

7. Order of Operations: Building Your Portfolio

Time Stamp: 50:49 – 60:06

• OG lays out the priorities for building wealth and managing investments:
  1. Asset Allocation — Match your mix to your long-term goals; filter out inappropriate assets first.

     “Asset allocation…isn’t so much about picking the right thing as it is about avoiding the wrong thing.” — Joe (52:54)

  2. Asset Selection — Choose broadly diversified funds; don’t sweat the difference between similar index funds.

     “Pick the one that suits whatever company you’re at.” — OG (56:20)

  3. Tax Strategy — Consider tax buckets, but don’t let tax avoidance distort your bigger strategy.

     “Don’t let the tax tail wag the dog.” — OG (57:11)

Notable Quotes & Moments

• “There is no way to have stock returns without stock volatility. It doesn’t exist.” — OG (25:04)
• “If your goal is to get rich quick...most likely, it’s get poor quick.” — OG (44:18)
• “Don’t trust the seller’s tax bill. It’s kept tighter than your jeans at Thanksgiving...You suddenly owe $4,600.” — TikTok Minute, paraphrasing real estate TikTok creator (39:30)
• “The more things change, the more they stay the same. I think that was the theme of your show today, Joe.” — OG (23:53)
• “You have a luck bucket and an experience bucket, and your goal is to fill up your experience bucket before you run out of your luck bucket.” — OG (44:18)
• “We want to talk about what you should do...diversification matters. Having money in a couple of penny stocks or in a couple yield street properties, probably not a great idea.” — Joe (43:55)

Timestamps for Core Segments

| Segment | Start | End | |---------------------------------------------------------|---------|---------| | Banter & Salute to Troops, New Year’s Reflections | 01:00 | 07:06 | | IPO Scams & Penny Stock Lessons | 09:05 | 16:30 | | Real Estate Schemes (Yieldstreet, Fundrise) | 20:16 | 24:01 | | Gambling Parallel, Volatility, & Luck vs. Skill | 26:51 | 29:26 | | Real Estate Tax TikTok Minute | 39:53 | 42:50 | | Practical Wealth-Building vs. Chasing Trends | 44:18 | 48:52 | | Investing Order of Operations: Allocation/Selection/Tax | 50:49 | 60:06 | | Listener Community Notes & Wrap Up | 61:17 | 69:06 |

Flow, Tone, and Listener Engagement

• The episode maintains the signature Stacking Benjamins “basement banter” — approachable, irreverent, and friendly (“What’s in that? Coffee drinking alone, OG?”).
• Listeners are made to feel like they’re at the card table, learning through stories, laughter, and honest talk.
• Engaging listener shoutouts and Q&A, with Doug riffing on their own “Spotify Wrapped” stats and quirky letters (61:36).

Actionable Takeaways

• Don’t fall for “invest like the 1%” hype or platforms promising “engineered superior results.”
• Beware of IPOs, penny stocks, or “emerging growth companies” that sound too good to be true.
• Diversify broadly—don’t try to get rich quick.
• Double-check real estate tax rules if you’re a homebuyer; taxes can uncap, increasing costs.
• Match your portfolio allocation to your long-term goal, not to the hottest trend or your tax situation alone.
• Focus on what you can control: time in the market, smart allocation, and continuous learning—not chasing luck.

Final Thoughts

2026 may be a “new year,” but no matter what’s trending—real estate schemes, risky IPOs, or whatever TikTok pitches next—building wealth comes down to the basics: patience, broad diversification, and avoiding shortcuts. The “same old rules” are still your best bet.

Next Episode:
Time management expert Laura Vanderkam joins the show Wednesday with strategies to help you make the most of your time all year long.