Podcast Summary: The Stacking Benjamins Show

Episode: Why Doing Less With Your Money Is the New Investing Edge (SB1815)

Date: March 13, 2026

Guests: Jen Smith (Frugal Friends), Doc G (Earn & Invest), OG (Co-host)

Episode Overview

In this fun and insightful episode, Joe Saul-Sehy and OG are joined by Jen Smith from Frugal Friends and Doc G from Earn & Invest. The group explores a Kiplinger piece on “Five Investing Rules You Can Steal From Millennials,” dissecting how millennial habits and the evolving financial landscape have shifted personal finance strategies for all ages. The roundtable discusses automation, tech’s double-edged sword, risk-taking, multiple income streams, and values-based investing—always with a mix of real-life stories, playful banter, and practical takeaways.

Key Discussion Points & Insights

1. Embracing Technology: Automate and Accelerate Investing

(Starts around 10:45)

• Jen Smith: Technology has made investing more accessible and affordable, especially for millennials who needed to start small due to economic headwinds after college.

  “Technology really has been the bedrock of my investing. I did not know that I could invest on my own. …I had to learn through podcasts like Stacking Benjamins.” (10:48)

• Doc G: Tech has both democratized and gamified investing. Automation (e.g., auto-enrolling in 401(k)s, target-date funds) has improved participation, but apps like Robinhood can encourage harmful overtrading.

  “It’s done both—democratized investing and gamified it. …the gamifying part is probably not as good for us.” (12:54)

• OG: Starting early, not perfectly, is more critical. Automation lowers the barrier to entry but can also expose personal weaknesses (e.g., gambling tendencies) easily.

  “If you are 80% correct, but you start right away, you have so much more flexibility and margin.” (16:38)

2. Budgeting Apps: Help or Hindrance?

(19:29)

• Jen Smith: Apps like Monarch, Tiller, and YNAB are useful, but can lead to “procrastispend”—spending on productivity tools as a form of avoidance.

  “People can procrastispend…spending money to do something productive instead of actually doing the thing.” (20:04)

• Tech has enabled better tracking but can cause unnecessary complexity, leading to budgeting fatigue.

  “Stop making two transactions at the grocery store where you're putting all your food first and then your paper products second, because those are two different categories in your budget.” (21:45)

3. The 24/7 Financial News Cycle: More Information, More Problems

(22:35)

• OG: Oversaturation of financial news creates “action bias”—the pressure to do something, often destructively.

  “When everything is crawling along the bottom of the screen... your brain can't delineate between an actual emergency or what CNBC thinks is an emergency. … Doing nothing almost all the time is the right thing to do.” (25:45)

• Doc G & Jen Smith: Point out that overconsumption of information confuses, overwhelms, and worsens decisions. Simpler can be smarter, and tuning out is often healthy.

  “If everything is important, nothing is important.” – Jen Smith (30:23) “It is what you make of it…just because you have access to more info, doesn’t make decisions easier or better.” – Joe (21:45, 29:44)

4. Risk—Don’t Be Afraid, But Be Smart

(42:44)

• Jen Smith: Millennials became accustomed to risk through the long bull market, but underlying fears linger from earlier economic struggles.

  “I think that [bull market] was what really shaped our risk tolerance…none of us anticipate retiring ever.” (43:34)

• OG: Risk is often misunderstood—it’s more about timeframe alignment than chance of loss.

  “Risk implies the chance of loss, but there’s really no chance of loss when investing in the biggest companies, given enough time.” (44:00)

• Doc G: Focus on “concentration versus diversification.” Take bigger risks in your career/side hustles, but not with speculative investing (e.g., crypto).

  “Be risky in your job, in building a business…once you make money, diversify so you don’t lose it.” (48:13)

5. Multiple Income Streams: Side Hustle Fatigue & The Importance of Focus

(51:33)

• Jen Smith: Side hustles were essential for millennials starting out, but now many see burnout. Networking and skill-building are more sustainable safety nets.

  “We needed [side gigs]…now it’s 10, 15 years later, we’re married, have kids—already tired…now it’s about protecting yourself and investing in your network.” (51:33)

• Doc G: Argues the “multiple revenue streams” mantra is overhyped—most already have them (job, investments, Social Security, etc.). Over-diversification distracts from excelling at primary work.

  “Most people are full of it when they talk about [multiple streams]…if you like your career, do that. Stop worrying.” (54:04)

• OG: Diversifying is good, but being truly great at your main gig brings compounding benefits and more opportunities.

6. Investing with Your Values (ESG): Pros, Cons & Cynicism

(58:22)

• Jen Smith: ESG investing suffered from bad actors and lack of transparency; most people don’t dig into what’s truly “values-aligned.”

  “It’s unfortunate that something that could have been really good got tarnished so quickly by some bad players.” (58:55)

• Doc G: It’s tough to match S&P 500 returns with ESG—but aligning investments with values can be worthwhile if you accept potential lower returns and do the research.

  “The answer can be either…if staying consistent with your values is more important, accept lower returns and study it.” (60:22)

• OG: “Vice Fund” (alcohol, defense, gaming, tobacco) had great returns—proving “doing good and doing well” is complicated and nuanced.

  “Do what’s best for you...it’s not our job to tell people how they should feel about investing.” (63:07)

• Jen Smith (hot take): True ethical investing may always come with a tradeoff in returns, because profits (and stock growth) depend on practices that aren’t always virtuous.

  “If we all did do this—the ethical thing—companies would not have as good of returns…and the returns would be not as good.” (67:08)

Notable Quotes & Memorable Moments

• “People can procrastispend...spending money on something productive like get healthier or get better with their money, instead of actually doing the thing.”
  — Jen Smith (20:04)

• “When everything is crawling along the bottom of the screen... your brain can't delineate between an actual emergency or what CNBC wants you to believe is an emergency. …Doing nothing almost all the time is the right thing to do.”
  — OG (25:45)

• “Just getting the biggest, most impactful snippets of information is going to be the best instead of knowing everything about everything…”
  — Jen Smith (30:23)

• “Don’t swing for the fences with your investments [in your 20s], swing for the fences in your career.”
  — Doc G (48:22)

• “Be so good they can’t ignore you.”
  — Steve Martin quote, referenced by Joe & OG (56:01)

Timestamps for Key Segments

• 10:45 – Embracing tech & automation in investing
• 19:29 – Budgeting apps & “procrastispend”
• 22:35 – 24/7 financial news: feature or bug?
• 42:44 – Millennials and risk: lessons learned
• 51:33 – Side hustles, multiple income streams, and networking
• 58:22 – ESG/values-based investing: reality vs. intentions
• 67:08 – Jen’s “hot take” on ethical investing and lower returns

Final Thoughts

The episode concludes with rapid-fire plugs for the guests’ podcasts, a playful check-in on trivia scores, and a reminder that often, less is more with your money. The central message: simplify, automate, avoid noise—and focus your risk and energy where you control the most, whether that’s in your career, your skills, or consistent, broad-based investing.

Listen to Jen Smith on Frugal Friends,

Doc G on Earn & Invest,
and follow Stacking Benjamins for more financial fun and wisdom.

Remember: “Doing nothing almost all the time is the right thing to do.” (OG, 25:45)