Podcast Summary: "How to Actually Use Money Apps the Right Way (According to FinTech Pros)"

The Stacking Benjamins Show | Episode SB1764 | Nov 21, 2025
Host: Joe Saul-Sehy | Guests: Peter Paulsen (Tiller), Aaron Froeg (Griffin), Ryan Ruff (Array)

Episode Overview

This special panel episode of The Stacking Benjamins Show explores the world of financial technology (fintech) apps and how to actually use them for better money management, budgeting, and investing. Host Joe Saul-Sehy is joined by three top fintech insiders—Peter Paulsen (Tiller), Aaron Froeg (Griffin), and Ryan Ruff (Array)—for a wide-ranging, candid conversation on app design, automation, security, building positive financial habits, and the impact of AI. True to the show's signature tone, the discussion is upbeat, down-to-earth, and packed with stories and memorable analogies.

Key Discussion Points & Insights

1. Meet the FinTech Pros: What Do Their Apps Do?

[02:23–11:08]

• Tiller (Peter Paulsen):
  Tiller consolidates all your financial accounts into a private spreadsheet (Google Sheets/Excel), auto-updating daily without ads or snooping (“Your data is just that, no ads. We don’t look at your data… into your sheet where it’s helpful and insightful to you”—Peter Paulsen, 04:31), focusing on privacy and user control.

  • Notably, Microsoft Money directed users to Tiller after discontinuing “Money in Excel” (05:05–06:16).

• Griffin (Aaron Froeg):
  Griffin auto-invests in the companies where you spend, “bringing joy and fun into investing.” If you buy coffee at Starbucks, you invest in Starbucks; shop at Whole Foods, you invest in Amazon.

  • The inspiration came from a sister’s joke at Starbucks: “I should own stock for how much I shop here” (07:00).
  • Dollar amounts per transaction are user-customizable: “A dollar just felt easier… you can set it to $5… $10… or 10% of a purchase" (08:46–09:29).
  • Focus on psychology—making investing accessible and less intimidating.

• Array (Ryan Ruff):
  Array builds “white-label” fintech tools (e.g., credit reports, subscription tracking) behind the scenes for banks, credit unions, and even podcasts/content creators—hugely expanding reach but often invisible to end-users (11:08).

2. Designing Simpler, More Human Money Apps

[13:07–19:35]

• Simplicity is a competitive advantage. Track everything in one place for awareness and control.
  • “Simply seeing all your data in one place is an enormous win for a lot of people.” —Peter Paulsen [15:56]
  • Tiller counts “clicks” to reduce friction: “Each click is a potential failure point because people… get decision paralysis.” —Ryan Ruff [18:32]
• Automation helps build habits; friction/bad UX hurts outcomes.
  • “The simplest idea is usually the best with everything, and how to just… make it feel real and human and like real life." —Aaron Froeg [16:14]
  • Positive automation = less abandonment, more participation.

3. Security, Data Friction, and Linking Accounts: Why It’s So Messy

[21:00–32:07]

• The Plaid Problem:
  • Fintechs use data aggregators (notably Plaid or Yodlee) to connect with banks. Banks have inconsistent or outdated tech, causing account linking to break—often erroneously blamed on the app:
    • “No matter what goes wrong, it’s Griffin. It doesn’t matter any third parties…” —Aaron Froeg [22:14]
    • “Chase… will start adding fees if aggregators want to access Chase banking data. It’s really upsetting.” —Peter Paulsen [26:24]
• Consumers lose out due to banks’ protectionism:
  • “For JP Morgan…to add fees and friction… for customers want their data on their money, I think it’s a huge step backwards.” —Peter Paulsen [27:44]
  • Some banks are “playing nice” with open banking; others are blocking access (30:45–32:07).

4. Sticking with Apps: Engagement, Motivation, & Community

[35:39–47:03]

• Common user mistakes:
  • “The biggest mistake is not staying engaged… let a week turn to a month… You get to the end of the year and you don’t actually know where your money’s gone.” —Peter Paulsen [36:07]
  • On the problem with notifications: Too many = annoyance. Solution: batch financial tasks for routine check-ins (39:23).
• Small steps matter:
  • “This is a dollar at a time… I’ve been able to put away $19,000 for myself.”—Aaron Froeg, showing his Griffin account [39:45]
  • Education is underused! Griffin’s 16-day email onboarding and knowledge base are often ignored—users should leverage these resources (42:24–42:53).
• Community is a game-changer—especially for habit-forming apps:
  • “You are the average of the five people you spend the most time with.”—Jim Rohn via Ryan Ruff [45:29]
  • Fintech communities (like Ynab’s “cult”) drive success; creator “trusted voices” help new users pick trusted apps [46:15–47:03].

5. Gamification: Ethics, Intent, and Engagement

[47:03–54:55]

• Positive gamification teaches and motivates; negative can encourage risky behavior:
  • “We only try to do positive things… if you invest for yourself this week, you earn a streak.” —Aaron Froeg [47:27]
  • Intent is everything:
    • “Whether we do this or not, however the product is designed, it’s going to trigger people’s biases. If you have good intent and you’re building your thing to gamify towards the goal that’s going to help a stacker… that’s the important thing.” —Ryan Ruff [49:18]
  • Gamification should reward small wins, not risky or destructive behavior.
• Ownership and financial identity:
  • “The concept of owning the world that you’re helping build. You’re putting your money towards there every single day. Why not be a part of it?” —Aaron Froeg [54:00]

6. AI in FinTech: Hype, Reality, Limitations, and Hopes

[58:35–67:37]

• How apps use AI:
  • Tiller: Uses AI for support, transaction categorization, and helping users feel “savvier when they feel stuck” (59:46–61:24).
  • Griffin: Building an AI support bot limited to their own compliance-reviewed knowledge base (64:15).
  • Array: Uses AI internally for tool-building, but nothing customer-facing—too early/trust issues (65:43–66:34).
• AI’s promise: rapid support, tailored insights, and democratized advice—but with caveats
  • “It’s an incredible way for people to feel savvier… but you have to treat everything with a grain of salt.” —Peter Paulsen [61:49]
  • Everyone warns that AI can confidently give very wrong answers—user vigilance is crucial (61:49–62:07).
• AI also increases consumer risk for fraud and scams.
  • “The opportunities for fraud are easier than ever… It’s increasingly challenging for consumers to know what they can trust.” —Peter Paulsen [67:06]

Notable Quotes & Memorable Moments

• On Simplicity:
  • “Even seeing it all… precedes tracking and even budgeting… that awareness is going to make them a more thoughtful agent of their own money.” —Peter Paulsen [15:56]
• On Real-Life Ties to Investing:
  • “Why can’t investing just be connected to real life and fun and makes sense?” —Aaron Froeg [07:00]
• On User Motivation:
  • “If you do nothing else but just stay engaged and get into their data once a week, they’re going to make progress.” —Peter Paulsen [37:11]
• On Intent and Gamification:
  • “Are they gamifying with my success in mind or are they gamifying with their success in mind?” —Peter Paulsen [55:04]
• On Community vs. Going Alone:
  • “The community teaches you how to use the tool… I think the real future is a trusted voice… that partners with cool apps that help their community get from point A to point B.” —Ryan Ruff [46:26]
• On Banking Friction:
  • “For JP Morgan… to add fees and friction… for customers who want their data on their money … it’s a huge step backward.” —Peter Paulsen [27:44]
• On Ownership:
  • “The concept of owning the world you’re helping build…” —Aaron Froeg [54:00]

Key Segment Timestamps

| Segment | Description | Timestamps | |---|---|---| | Introductions & App Overviews | Meet the founder-guests, their origin stories, and product focus | 02:23–11:08 | | Simplicity & User Experience | Why design matters and the importance of reducing barriers | 13:07–19:35 | | Connectivity & Data Friction | How banks and aggregators complicate the user experience | 21:00–32:07 | | Building and Keeping Financial Habits | Common mistakes, notifications, the role of community support | 35:39–47:03 | | Gamification, Ethics, and Intent | Good vs. bad gamification, outcomes, and user motivation | 47:03–54:55 | | AI: Opportunities and Cautions | Support bots, personalization, fraud risks, and trust challenges | 58:35–67:37 | | Product Updates & Future Features | Coming soon for Griffin, Tiller, Array—incl. wrapping up and takeaways | 68:02–end |

What’s Next for Each FinTech?

Griffin

• Weekly investing quizzes via email (68:15)
• Building family plans for parent/kid investing conversations
• Holiday features and a “Spotify Wrapped”-type year-in-review for spending/investing in the works

Tiller

• Better bank data connections, mobile tools, new beta features
• More community-building webinars/educational content—especially for new year’s resolutions
• Emphasis on comparing year-over-year spending trends [71:00]

Array

• Tools to help Stacking Benjamins listeners understand their credit, shed subscription waste, and protect privacy (in partnership with the podcast) [72:37]

Final Takeaways (per Doug)

[74:57]

1. Take advantage of new fintech tools for easier financial management.
2. The pace of change, supercharged by AI, means you should regularly re-evaluate your apps.
3. And most important: Don’t tell Joe’s mom about these fintech innovations... she’ll claim it was a comedy act from the 60s.

For Listeners:

• Try Tiller for budgeting via spreadsheet: tiller.com
• Explore Griffin for fun, real-life investing: griffin.com
• Get access to Array’s tools via Stacking Benjamins: stackingbenjamins.com/vault

Show Tone:
Light, humorous, practical—focus on making money approachable and fun, with expert knowledge delivered in a relatable, fast-paced style.

(Summary by AI for listeners who want the full inside scoop without the ads, promos, or waiting for punchlines!)