The Stacking Benjamins Show

Episode SB1749: What Lucky People Do Differently With Money

Release Date: October 17, 2025
Hosts: Joe Saul-Sehy, OG, Paula Pant, Doug
Guest Contributor: Chris Luger (Heavy Metal Money)

Episode Overview

This engaging roundtable episode explores the myth and mechanics of “luck” in the world of personal finance. Joe and OG, joined by Paula Pant (Afford Anything) and Chris Luger (Heavy Metal Money), use a recent Kate Hall Substack post as their jumping-off point. The discussion weaves together practical financial advice, psychological perspectives, and personal anecdotes to illuminate what “lucky” people actually do to help chance favor them—especially with money.

Key Discussion Points & Insights

1. Redefining Luck: It’s Not Just Chance—It’s Surface Area

• Luck & Probability

  • Paula Pant introduces the core concept: luck increases with the number of attempts you make. More tries mean a higher probability of a positive outcome.

  • “Luck is a function of the number of times that you've tried... it's just probability.” (11:21)

• Taking At-Bats, But with Thought

  • Chris Luger adds that while more tries increase the odds, the context and quality of tries matter. Networking, learning, and skill acquisition often set the stage for “luck.”

  • “You increase your luck by... learning new skills, networking, and meeting the people around you. Taking a risk: that's the number one thing.” (12:24)

• Risk Management

  • Joe and Chris debate if better awareness of probabilities (teaching statistics) might make people more (or less) willing to take good risks. (13:11–13:50)

• Systems > Luck

  • OG pivots to the power of systems in personal finance—suggesting disciplined, automated investing (e.g., rebalancing, consistent contributions) leads to good results that appear “lucky” to outsiders.

  • “I think it's less luck, and I think it's more discipline.” (15:40)

2. Curiosity: The Engine of Serendipity

• Curiosity Expands Opportunity

  • Joe highlights Kate Hall’s suggestion that being curious draws more opportunities toward you, setting you up for luck.
  • Chris agrees, noting his own natural curiosity led to skills and relationships key to his success—but emphasizes that action must follow curiosity.

  • “You can be curious... but you also have to be able to take action on the things you've learned.” (25:33)

• Beyond the Transactional

  • Paula and Joe discuss the importance of non-transactional, long-term relationship-building as a source of unpredictable but powerful opportunities—contrasting short-term payoff-seeking with deeper curiosity.

  • “Transactional approaches can only take you so far. But developing relationships, that's where you reap these long-term rewards.” (27:37)

• Who, Not How

  • Referencing the business book “Who Not How,” the group discusses how expanding your social circles and focusing on connections can spark “lucky breaks” through referrals and new ideas. (29:06)

3. Systems, Disciplined Experimentation, and the Infinite Game

• When to Experiment & When Not to

  • The panel notes that while experimenting and “more tries” work in some domains (career, skill-building), too much experimentation with core financial systems (like investing) can backfire.
  • OG advocates for simplifying decisions:

    • “When it comes to money and goal attainment... maybe [making] fewer decisions actually is the better way to do it.” (16:07)

• Budgeting & All-or-Nothing Thinking

  • Paula and Joe discuss “budgeting doesn’t work for me” thinking, pushing back with the idea that small tweaks (not abandoning a system) and flexibility, much like in diet and exercise, are crucial to sticking with good habits. (18:51–20:47)

  • “People develop an all or nothing approach to [diets], and because of that if there's an element that doesn't work, people will often just give up the whole thing.” (19:24)

• Diversification vs. Perfection

  • OG chides clients (and listeners) who obsess over the minutiae of asset allocation, arguing that simply being consistently invested matters more than picking the “perfect” allocation.

  • “The fact that you are investing matters. The fact that you're saving money matters.” (24:39)

4. Giving Before Getting: How Generosity Breeds “Good Luck”

• The Giver’s Edge

  • Chris and Paula discuss how a “giving” approach leads to a network that’s warmer and more eager to return favors—expanding one’s surface area for luck through generosity.

  • “The more generous you are, the more it comes back to you in a variety of ways.” (49:13)

• Ben Franklin Effect

  • Paula introduces the concept that, paradoxically, people like others more after they themselves have done them a small favor.

  • “People will like you more if you reach out to them and ask them for small bits of help occasionally.” (49:39)

• When Giving Goes Too Far

  • OG warns of generosity without boundaries—like supporting adult children excessively—cautioning listeners to balance their giving with responsibility. (51:10)

5. Success, Focus, and “Manifesting”

• Luck & Manifestation: Two Sides of Focus
  • The panel expresses skepticism toward the “manifestation” movement, preferring a focus-driven view: success comes when you pay conscious attention to goals and act persistently on achieving them.

  • “You succeed at what you focus on, and if you're focusing on that, then that's what'll happen.” (55:12)

6. Planning for the Uncertain Future: Discipline with Flexibility

• Goals Can Change

  • Paula and Chris illustrate, with anecdotes about saving for years toward homeownership or maintaining family endowments, that it’s okay to change course—and that flexibility is vital.

  • “She has the discipline to save the money. She also has the flexibility to at all times reconsider whether or not her initial goal… is the correct one.” (61:25)

• For Young Listeners

  • OG and Chris advise young adults not to worry about “perfect clarity.” Instead, set targets 6–12 months out, review regularly, and be gentle with yourself as you build up a vision for your future.

  • “If you can pull something that's six months away, that's great. If you can pull something that's a year away, that's great.” (58:31)

Notable Quotes & Memorable Moments

• On the Mathematics of Luck:
  • “Luck equals math.” – Joe Saul-Sehy (11:44)
• On Systems Over Screwing With It:
  • “The people who just pick an asset allocation, make a decision once a year to rebalance… they wake up going, huh, I don't even know how I got 2 million bucks. It's because you didn't screw with the system.” – OG (16:52)
• On Taking Action:
  • “You can be curious, but you gotta take action.” – Chris Luger (26:51)
• On Relationships & Asking ‘Who, Not How’:
  • “We are an interdisciplinary species, interdependent species. Right. Rely on other people to rely on that interdependence.” – Paula Pant (29:23)
• On Infinite Game in Finance:
  • “Just play the infinite game.” – Steel off tees (Listener via chat, 62:06)

Timestamps for Important Segments

• [11:21] – Probability, luck, and the number of attempts (Paula)
• [12:24–13:39] – Risks, action, and learning new skills (Chris)
• [15:40–16:52] – Systems vs. luck in financial planning (OG)
• [25:33–26:51] – Curiosity and taking action (Joe & Chris)
• [27:37–29:23] – Relationships, transactional vs. non-transactional, “Who Not How” (Paula & Joe)
• [49:13–50:16] – Giving before getting, Ben Franklin effect (Chris & Paula)
• [55:12] – Manifesting vs. hard focus and work (OG & Chris)
• [58:31] – Flexible goal-setting for young adults (OG & Chris)
• [61:25] – Flexibility in goals and discipline (Paula)

Section: Trivia Interlude

Midway, Doug challenges the panel with a quirky trivia question: How many imperial gallons equal a “buttload” of wine?

• Answer: 126 imperial gallons (48:03)
• OG wins this week’s trivia round, pulling closer to the yearly championship lead.

Takeaway Lessons (as summarized by Doug, 68:40):

1. Be Curious, Not Judgmental.
   Curiosity (paired with action) expands your opportunities and helps you stumble onto “luck.”
2. Persistence and Flexibility Beat All-or-Nothing Thinking.
   Long-term systems with room for change (rather than rigid, short-term plans) win the infinite game.
3. Generosity Supercharges Luck.
   Givers, not takers, seem to get more “lucky” breaks—from genuine relationships and a spirit of abundance, not mere transactions.

Episode Tone

• Light-hearted yet thoughtful
• Playfully irreverent (occasional gentle roasting among hosts)
• Encouraging, focused on empowering listeners regardless of where they are on their financial journey

Links & Further Resources

• Heavy Metal Money podcast and YouTube
• Afford Anything podcast
• [Kate Hall’s Useful Fiction Substack: “How to increase your surface area for luck”] (linked via show notes)
• Stacking Benjamins Twin Cities Meetup Group (Facebook)

For listeners and new stackers:
“Luck” with money isn’t magic. It’s about showing up often, being curious, fostering real relationships, taking strategic risks, and sticking with good systems—while remaining flexible and generous along the way.