The Personal Finance Podcast

Episode: How to Automate Your Finances (Money on Autopilot!)

Host: Andrew Giancola
Date: November 26, 2025

Episode Overview

In this highly-requested episode, Andrew Giancola takes listeners step-by-step through his signature “Money on Autopilot” system. He makes a compelling case for automating all aspects of your finances—from bills and investments to savings—and lays out a concrete plan you can set up in a single weekend. Andrew emphasizes that success with money isn’t about willpower or obsessively tracking every penny; it’s about building systems that work for you in the background, minimizing stress and freeing up mental and emotional energy for what truly matters.

Key Discussion Points and Insights

1. Why Automation Is a Financial Superpower

• You are not bad with money—most people just lack a system.
• Automation solves financial chaos, late fees, procrastination, and money fights.
• The goal: Spend less time thinking about money and more on high-impact decisions (investments, income growth).

Quote:
"Your biggest problem isn’t your income, it’s chaos... Automation removes all of this. It removes the late fees. It removes those money fights with your spouse. It removes the missed investments. It removes the emotional decision making."
— Andrew Giancola [03:20]

2. Six Steps to Automate Your Finances

Step 1: Build a "Flow Through" Account ([09:23])

• Treat your checking account as the central “waterfall” through which all income flows and expenses/outflows are automatically distributed.
• Keep this account lean—ideally one month of expenses.
• Couples: Even if you don’t combine finances, use a joint checking for shared bills to avoid constant transfers (“money automation doesn’t work when you’re venmoing your spouse back and forth”).

Step 2: Automate Your Investments and Wealth Building ([12:45])

• Always pay yourself first—prioritize automating investments.
• Typical order of operations:
  1. Employer Match (401k/403b): “Free money! Free is my favorite number.” ([14:02])
  2. Health Savings Account (HSA) for those with high-deductible plans.
  3. Roth IRA/Traditional IRA (use backdoor for income limits).
  4. 401k/403b beyond the match.
  5. Taxable Brokerage Account: Especially for flexibility and early retirement.
  6. Other goals (529 plans, kids’ accounts)—AFTER retirement is secure.
• Important: “There are no loans for retirement. You’ve got to make sure your retirement comes first before everything else.” ([16:30])

Step 3: Automate Bill Payments ([21:09])

• “If it has a due date, I want you to automate it.”
• Manual bill pay costs time, increases risk of late fees (he quantifies the lost investment growth from late fees: $5,500+ over 10 years at 9%).
• How to automate:
  • Pay as many bills as possible with a credit card for points/cashback (ONLY if responsible).
  • Everything else comes from checking/debit.
  • For credit cards: turn on autopay and, optionally, pay weekly for tighter control.
• FAQ: What if I’m living paycheck to paycheck?
  • Call providers and stagger bill due dates to shortly after paydays.
  • Use budgeting apps (like Monarch Money) to visualize upcoming bills.

Step 4: Automate Your Spending Plans ([28:45])

• Use apps like Monarch Money to automatically categorize and track expenses (“it was the most tedious and time-consuming thing ever [by hand]... now you could spend $4 a month on Monarch and never think about it”).
• For those tight on cash: try the "five-minute drill"—quickly categorize transactions daily until automation is feasible.

Step 5: Automate Savings and Safety Nets—The Bucket Method ([31:25])

• Set up high-yield savings with “buckets”: separate funds for emergency, car repairs, vacation, holiday spending, etc.
• “Treat holidays like a bill—divide last year’s spending by 12 and save that each month.”
• Car purchases: Save monthly so you never need another car loan.

Step 6: The 10-Minute Monthly Review ([34:44])

• Once a month, check:
  • Did every investment go through?
  • Did every bill hit?
  • Have any subscriptions changed or increased in price?
  • Do I need to automate something new?
• “You might feel like you’re not doing enough—but that means your system is actually working!”

Notable Quotes & Memorable Moments

On Mindset and Systems

• “I want you to automate your money so you can think about the big decisions: your taxes, where you’re going to live, how you’re going to allocate your investments, how you’re going to earn more money, negotiate your salary. Those are the big ticket items I want you to think about.” ([04:40])

On Willpower vs. Systems

• “Willpower is something that is finite... It’s impossible to rely on that. If I relied on my willpower, I would never be where I am today. Automation changes that for you.” ([07:20])

On Feeling Less Busy With Money

• “[Listeners] set up these money automations, and they feel like they should be in their spreadsheet, but they don’t have to do that anymore... If you feel like you’re not doing enough, that means the system is working!” ([35:10])

On Real-Life Impact

• “Automation is how you reduce stress. It is how you reduce that anxiety. When I hit rock bottom... automation clawed me out of the paycheck to paycheck cycle.” ([36:10])

Timestamps of Important Segments

| Segment | Timestamp | |----------------------------------------------|-------------| | Why automation is crucial | 02:20-06:30 | | Step 1: Flow-through checking account | 09:23 | | Step 2: Automating investments & order | 12:45-17:10 | | Step 3: Automating bills & practical tips | 21:09-26:40 | | Step 4: Automate spending/expense tracking | 28:45 | | Step 5: Bucket method for savings goals | 31:25-34:10 | | Step 6: 10-minute monthly check-up | 34:44-36:00 | | Real-life outcomes and closing thoughts | 36:00-37:40 |

Actionable Takeaways

• Set up a single central “flow-through” checking account for all income and outgo.
• Automate investment contributions according to your own financial priorities, always starting with employer match and retirement.
• Put every bill on autopay—preferably through a rewards credit card if you can manage it responsibly.
• Automate savings into specific high-yield “buckets” for each goal.
• Use technology (Monarch Money, etc.) to automate expense tracking.
• Once everything is in place, check for updates and anomalies in a single 10-minute monthly review.
• “If it has a due date, automate it!”

Resources & Further Learning

• Free Download: Money Automation Checklist (see show notes)
• Course: Automate Your Money in One Weekend ($27 special, link in show notes)
• Episodes:
  • Full breakdown of bucket method
  • Credit card rules
  • HSA deep dive
• Tools Mentioned: Monarch Money, Ally Bank (for savings buckets), Vanguard, Fidelity

This episode is a hands-on guide for listeners of all experience levels to put their finances firmly on autopilot, cut down stress, and channel energy into the financial decisions that matter most.