Money Guy Show Episode Summary: "Financial Confessions: The Money Mistakes You’ll Never Forget"

Release Date: May 19, 2025
Hosts: Brian Preston and Bo Hansen

In this compelling episode of the Money Guy Show, hosts Brian Preston and Bo Hansen delve into candid confessions from their listeners, unveiling a series of memorable financial missteps. Through these personal stories, the hosts offer insightful commentary, practical advice, and valuable lessons to help listeners navigate their own financial journeys more wisely.

1. Introducing Financial Confessions

Brian and Bo kick off the episode by expressing their excitement about sharing real-life financial confessions from their audience. They emphasize the importance of learning from others' mistakes to build stronger financial strategies.

Brian Preston (00:22):
"These are our people. These are our financial mutants explaining some of their money decisions. I'm curious to see how this goes. Let's dive right in."

2. Hank's Undergarment Saga: A Lesson in Frugality

Hank shares a humorous yet telling story about his extreme frugality in managing clothing expenses.

Hank (00:33 - 01:44):
"I hate buying clothes. I don't place any value on clothing other than just a utility. And so I wear them beyond what maybe a reasonable person would do... I kept wearing them because why replace them if they're still functional, right?"

Hank's reluctance to replace worn-out underwear eventually leads to a domestic fiasco, prompting his wife to insist on discarding the threadbare garments. This incident underscores the fine line between being frugal and neglecting essential expenses.

Brian Preston (01:44):
"This is a big L. It's not a money win."

Bo Hansen (02:09):
"I like the coin term, I think that this is not healthy for you. Walk away from it."

3. Misusing the Roth IRA: Hank's Contribution Conundrum

Continuing with Hank's financial confessions, he reveals a critical mistake involving his retirement savings.

Hank (03:28 - 04:14):
"Back in 2016, I contributed $2,400 to my Roth IRA for the year. And the very next month... the repair bill was exactly $2,400. I didn't feel confident taking the money from my maintenance sinking fund or my emergency fund... so I withdrew my contribution for the year."

Brian and Bo probe into why Hank chose to tap into his Roth IRA instead of utilizing his designated emergency funds, highlighting the importance of maintaining clear financial boundaries and accessing funds appropriately.

Brian Preston (03:58):
"The maintenance fund is there for when you have maintenance issues come up, you go and draw from it."

Bo Hansen (04:39):
"A $2,400 mistake you can recover from... I wouldn't pull that lever again."

4. Rick's Savings Account Mismanagement: The $255,000 Trap

Rick confesses to a significant oversight in his savings strategy, revealing a substantial sum trapped in a low-yield account.

Rick (04:14 - 05:34):
"I've been contributing 5% of my paycheck to a regular savings account. It was just to set it and forget it... That account now has $255,000 in it. And it's killing me knowing what that could have been had I actually invested it in say, a Roth IRA or something like that back when I was in my 20s."

The hosts discuss the missed opportunities and the critical nature of choosing the right savings vehicles to maximize returns.

Brian Preston (05:48):
"Even worse than that. It wasn't even a high yield account. I mean, even if you're going to build up cash, at least if you're making, you know, recently four on that, that's something. But this is hundreds of thousands of dollars that sat there earning less than 1%."

Bo Hansen (05:34):
"Has she gone through the process?... I could have gotten you out of the penalty for Virginia."

5. Bill's Tax Withholding Nightmare: Double Payments and Penalties

Bill shares a frustrating experience with tax withholding errors that resulted in double tax payments and penalties.

Bill (07:14 - 12:17):
"They switched my tax withholding to D.C. and for whatever reason, I could not get them to change that tax withholding. And when it came time to actually file my taxes at the end of the year... I paid the Virginia taxes as well, while also having previously paid my taxes to D.C."

Brian and Bo analyze the situation, emphasizing the importance of accurate tax withholdings and the benefits of consulting with tax professionals to rectify such issues.

Bo Hansen (10:30):
"If you go see the right tax preparer, CPA, they can help you unwind this situation."

Brian Preston (10:17):
"A lot of do-it-yourselfers, you don't like to pay fees, you just think you go do it all yourself. But this is a perfect example that if you go see the right tax preparer, CPA, they can help you unwind this situation."

6. Rick's Bitcoin Regret: A Volatile Investment Journey

Rick opens up about his tumultuous relationship with Bitcoin investments, reflecting on lost opportunities and emotional trading behavior.

Rick (12:17 - 20:07):
"In 2008, my dad told me about Bitcoin. I convinced him that it was a scam... Later, I finally decided to get into it in 2016, and I sold when it would crash and foolishly bought back in after it went up... I would probably have over a million dollars by now if I had just always been buying small amounts."

Brian and Bo critique Rick's approach, highlighting the dangers of emotional investing and the importance of aligning investments with one's risk tolerance.

Brian Preston (19:04):
"You were investing in something that did not make sense for your unique investor profile."

Bo Hansen (19:04):
"You're too risk-averse, which I would say is a healthy thing. You just got to make sure that the rest of your actions match the journey."

7. Investment Gone Wrong: Holding Funds in Uncertified Ventures

Another confession involves an individual who invested $25,000 in an unverified investment opportunity, resulting in locked funds and uncertainty.

Bo Hansen (16:52 - 17:12):
"This is not healthy for you. Walk away from it... Everything you shared, your risk profile is, you were too risk-averse, which I would say is a healthy thing."

Brian and Bo advise caution against high-risk, speculative investments, advocating for safer, diversified investment strategies like index funds to mitigate emotional and financial risks.

8. Key Takeaways and Lessons Learned

Throughout the episode, Brian and Bo synthesize the shared confessions into actionable financial wisdom:

• Maintain Clear Financial Boundaries: Utilize designated funds (like emergency or maintenance funds) appropriately without compromising retirement savings.

• Optimize Savings Vehicles: Avoid low-yield savings accounts for substantial funds; instead, consider higher-yield options or investment accounts to maximize growth.

• Seek Professional Assistance: Complex financial issues, such as tax withholdings or investment missteps, benefit greatly from expert advice, preventing costly errors and penalties.

• Align Investments with Risk Tolerance: Emotional trading and speculative investments can lead to significant losses. It's crucial to invest in instruments that match one's risk appetite and long-term goals.

• Learn from Others' Mistakes: Sharing and analyzing others' financial missteps provides valuable insights, helping listeners avoid similar pitfalls.

Brian Preston (20:07):
"How your journey begins does not define how your journey has to end. Even when it comes to financial mutants."

Bo Hansen (20:32):
"We love our audience and we love creating this type of content."

Conclusion

"Financial Confessions: The Money Mistakes You’ll Never Forget" serves as a powerful reminder that financial missteps are common but surmountable. By openly discussing and analyzing these mistakes, Brian Preston and Bo Hansen provide listeners with the tools and perspectives needed to build more resilient and informed financial strategies. Whether it's managing savings, optimizing investments, or navigating tax complexities, the episode underscores the importance of continuous learning and prudent decision-making in the journey toward financial confidence and fulfillment.

For those who wish to share their own financial confessions, Brian and Bo encourage listeners to visit moneyguy.com/confessions and contribute their stories, fostering a community of shared experiences and collective growth.