Podcast Summary: The Stacking Benjamins Show

Episode: Tales of Financial Horror (and how we exorcised them) SB1755
Date: October 31, 2025
Host: Joe Saul-Sehy
Guests: Doc G (Earn & Invest), Jesse Kramer (Best Interest Blog), Emily Agashira (Hey Friend, It’s Em), and Neighbor Doug

Overview

This special Halloween episode of The Stacking Benjamins Show turns the basement card table into a virtual campfire, with Joe and his guests sharing real-life “financial horror stories” – tales of money mistakes, bad purchases, and the hard lessons learned. The panel—Doc G, Jesse Kramer, and TikTok/Instagram star Emily Agashira (“Em”)—reflect on how these financial frights taught them resilience, caution, and a dose of humor. The episode maintains Stacking Benjamins’s signature warm, teasing style, mixing laughter with meaningful money takeaways.

Key Discussion Points and Insights

Panel Introductions & Tone Setting (01:58–06:19)

Joe welcomes listeners to a story-filled Halloween special, promising both entertainment and learning.
Panel introductions emphasize each guest’s background and strengths:
- Doc G: Hospice physician and personal finance podcast host, back from travel.
- Jesse Kramer: Writes about long-term investing and practical finance.
- Emily Agashira (Em): Creator who documents her journey from poverty to debt-free millionaire, focusing on frugality and “de-influencing” overconsumption.

“For you to get as far as you have with your money, like you’ve just done everything perfect. M. Everything’s perfect for Em and her family all the time.”
— Joe Saul-Sehy [05:13]

Doc G’s Tale: The Perils of Estate Planning Delay (08:21–11:15)

Story (08:21–10:57)

Doc G shares the story of "Dan," whose father had all financial and medical power of attorney for his ill wife. When the father suddenly became incapacitated due to COVID, Dan was unable to pay for his mother's critical care and access family finances. Relief only arrived after his father's passing, when contingency plans kicked in—but guardianship court could have drawn out the crisis.
Lesson: Not having updated, transferable financial documents (like power of attorney) can instantly create horrific legal and logistical problems for families.

“If his dad had remained alive but on the ventilator and incapacitated, (Dan) would have had to go to the court systems and try to take over their financial control. And that can cost lots of money and a lot of time.”
— Doc G [09:43]

Insights & Reactions (11:15–17:32)

Em and Joe discuss the discomfort and avoidance of estate planning, especially for young parents, but how much relief comes from finally getting it done.
Jesse notes that failing to plan means letting the state decide – “do you really want the state you live in to be in charge of your estate plan?” [16:05]
The conversation highlights that setting up wills, directives, and powers of attorney is easier and more affordable than ever with online tools.

Emily’s Tale: The $60,000 Car Lease – Chasing Validation Through Debt (17:32–24:58)

Story (17:32–20:01)

At 24, Em fell victim to lifestyle inflation and FOMO by leasing a $60,000 Audi—equal to her annual income—pressured by then-relationships and dealership tactics. She rolled $12,000 of old equity and made a $2,000 upfront payment to lower the lease payment, ending up paying $550/month (total $35,000 over three years).
Exacerbated by expensive required maintenance (e.g., $1,200 for tires), Em realized only later that the allure of “affording the payments” blinded her to the real, long-term opportunity cost.

“I had the mentality of if I can afford the payments, I can afford the car. And that is such a common theme that we…see and hear a lot nowadays.”
— Em [19:14]

Insights & Reflection (20:01–28:02)

Panelists explore why people focus on monthly payments, rationalizing big purchases, and the dangers of prioritizing short-term happiness and social validation.
Em ties her story to generational hopelessness (“Why bother? I’ll never buy a house anyway”) as a reason people overspend on small luxuries instead.
Joe commends Em for ultimately breaking this pattern, including paying off her home early for peace of mind despite prevailing financial advice.

Jesse’s Tale: The Hot Tub Hustle – Impulse + Sales Pressure (39:16–44:12)

Story (39:16–41:51)

Jesse shares his regret over buying an $11,000 luxury hot tub after a vacation, influenced by “rent-vs-buy your fun” wisdom and social pressure.
The hot tub salesman employed emotional manipulation, including sharing “personal” stories about his daughter’s student loans, which Jesse later recognized as classic influence tactics.
Lesson: High-pressure sales settings are engineered for impulse, and recognizing manipulative tactics can help you avoid mistakes.

“I made the decision because we were just coming off of a fun mountain retreat with friends… It’s hard to recreate those vacation vibes in just everyday life.”
— Jesse [39:32]

Insights & Strategies (44:12–46:32)

Em adds that “frictionless” buying online amplifies these impulse vulnerabilities. She recommends the 24-hour rule (save to cart and sleep on it), which leads her to cancel most impulse purchases.
The “cooling-off” period: Some purchases have grace periods by law—Jesse notes this applies to his hot tub state and to vehicles/insurance in some cases.

Doug’s Tale: Designer Frames, Emotional Shopping, and Buyer’s Remorse (46:58–49:07)

Doug reminisces about purchasing $1,400 antique eyeglasses during an emotional period, tying it to the “I’m making adult money now” trap. Years later, he realized the opportunity cost and regrets the purchase—a tale of patience, context, and monetary wisdom gained late.

“There are some stories that aren’t horror stories until years later when you realize what the opportunity cost was…”
— Doug [48:34]

Joe’s Tale: The Midas Muffler Upsell – Recognizing a Rip-Off (49:26–52:42)

Young Joe succumbs to an upsell at a car shop, buying unnecessary upgrades for an old Monte Carlo after a charismatic worker sells him on restoring it. The receptionist covertly offers him a coupon, wordlessly signaling he’s being taken advantage of.

Key Takeaways and Memorable Quotes

On the danger of “I deserve it”:

“The most dangerous phrase for a broke person to say is, ‘I deserve it.’”
— Joe [49:26, referencing Buffy Purcell]
On “good debt” and paying off her mortgage:

“Our whole goal was being debt free. I wanted freedom, total freedom. I didn’t want to owe anything to anyone…”
— Em [27:26]
On rationalizing payments:

“It was my first school of hard knocks lesson in the way that hard sales tactics work.”
— Jesse [39:37]
On survivable mistakes:

“Most of these stories are stories that really burn you because you spent when you shouldn’t have spent… but hopefully we learn from them.”
— Doc G [51:45]
On estate planning inertia:

“If you don’t have a will, the state has a will for you. You do have a will.”
— Joe [16:05]

Notable Quotes with Timestamps

On the illusion of perfection:
“People think that for you to get as far as you have with your money, like you’ve just done everything perfect. M. Everything’s perfect for Em and her family all the time.”
— Joe Saul-Sehy [05:13]
On the comfort of finally planning for the future:
“It shocked me how much better I felt. I was blown away by how all of a sudden… I felt so good. I was like, I never thought I’d feel this good. I thought I’d feel morbidly bad because I was acknowledging death…”
— Joe Saul-Sehy [13:01]
On opportunity cost:
“If Emily now knew what I knew back then and I invested $550 every month, I mean, we’re talking serious money.”
— Em [21:51]
On succumbing to sales tactics:
"It was my first school of hard knocks lesson in the way that hard sales tactics work. And I can still remember this sales guy sitting in my kitchen... telling me about his daughter's student loans and how every sale is meaningful to him..."
— Jesse [39:37]
On learning from mistakes:
“You have to put your hand on the stove once to know to avoid the stove later on in life… Thank God this was a recoverable mistake.”
— Doc G [22:31]

Important Timestamps

08:21: Doc G’s family power-of-attorney nightmare
17:32: Em’s $60k Audi lease horror
39:16: Jesse’s “hot tub hustle” story
46:58: Doug’s eyeglasses emotional overshopping
49:26: Joe’s Midas muffler rip-off
51:45: Panel reflects on survivable financial mistakes

Actionable Lessons & Takeaways

Get your financial and estate planning done early, especially with children or dependents.
Beware lifestyle inflation and the trap of “I can afford the payment.” Assess the total cost and opportunity cost.
Recognize emotional and manipulative sales tactics—sleep on big purchases and create friction before you buy.
Don’t let media negativity or social comparison take you out of the game. Even if goals feel far off, progress is possible.
Remember, everyone makes mistakes—use them as tuition, not tombstones, for your financial journey.

Closing & Additional Resources

Connect with the guests:
- Em: “Hey Friend, It’s Em” on TikTok/Instagram
- Jesse: Personal Finance for Long Term Investors (podcast and Best Interest Blog)
- Doc G: Earn & Invest podcast
Join the Conversation:
- Share your financial horror stories in the Stacking Benjamins Facebook group (stackingbenjamins.com/basement)
- Submit questions via voicemail at stackingbenjamins.com/voicemail

Signature show elements like trivia and playful ribbing abound, but this summary focuses on the episode’s heart: candid, educational, and often hilarious stories of financial mistakes and the wisdom gathered from each scare.

Podcast Summary: The Stacking Benjamins Show

Overview

Key Discussion Points and Insights

Panel Introductions & Tone Setting (01:58–06:19)

Joe welcomes listeners to a story-filled Halloween special, promising both entertainment and learning.
Panel introductions emphasize each guest’s background and strengths:
- Doc G: Hospice physician and personal finance podcast host, back from travel.
- Jesse Kramer: Writes about long-term investing and practical finance.
- Emily Agashira (Em): Creator who documents her journey from poverty to debt-free millionaire, focusing on frugality and “de-influencing” overconsumption.

“For you to get as far as you have with your money, like you’ve just done everything perfect. M. Everything’s perfect for Em and her family all the time.”
— Joe Saul-Sehy [05:13]

Doc G’s Tale: The Perils of Estate Planning Delay (08:21–11:15)

Story (08:21–10:57)

Doc G shares the story of "Dan," whose father had all financial and medical power of attorney for his ill wife. When the father suddenly became incapacitated due to COVID, Dan was unable to pay for his mother's critical care and access family finances. Relief only arrived after his father's passing, when contingency plans kicked in—but guardianship court could have drawn out the crisis.
Lesson: Not having updated, transferable financial documents (like power of attorney) can instantly create horrific legal and logistical problems for families.

“If his dad had remained alive but on the ventilator and incapacitated, (Dan) would have had to go to the court systems and try to take over their financial control. And that can cost lots of money and a lot of time.”
— Doc G [09:43]

Insights & Reactions (11:15–17:32)

Em and Joe discuss the discomfort and avoidance of estate planning, especially for young parents, but how much relief comes from finally getting it done.
Jesse notes that failing to plan means letting the state decide – “do you really want the state you live in to be in charge of your estate plan?” [16:05]
The conversation highlights that setting up wills, directives, and powers of attorney is easier and more affordable than ever with online tools.

Emily’s Tale: The $60,000 Car Lease – Chasing Validation Through Debt (17:32–24:58)

Story (17:32–20:01)

At 24, Em fell victim to lifestyle inflation and FOMO by leasing a $60,000 Audi—equal to her annual income—pressured by then-relationships and dealership tactics. She rolled $12,000 of old equity and made a $2,000 upfront payment to lower the lease payment, ending up paying $550/month (total $35,000 over three years).
Exacerbated by expensive required maintenance (e.g., $1,200 for tires), Em realized only later that the allure of “affording the payments” blinded her to the real, long-term opportunity cost.

“I had the mentality of if I can afford the payments, I can afford the car. And that is such a common theme that we…see and hear a lot nowadays.”
— Em [19:14]

Insights & Reflection (20:01–28:02)

Panelists explore why people focus on monthly payments, rationalizing big purchases, and the dangers of prioritizing short-term happiness and social validation.
Em ties her story to generational hopelessness (“Why bother? I’ll never buy a house anyway”) as a reason people overspend on small luxuries instead.
Joe commends Em for ultimately breaking this pattern, including paying off her home early for peace of mind despite prevailing financial advice.

Jesse’s Tale: The Hot Tub Hustle – Impulse + Sales Pressure (39:16–44:12)

Story (39:16–41:51)

Jesse shares his regret over buying an $11,000 luxury hot tub after a vacation, influenced by “rent-vs-buy your fun” wisdom and social pressure.
The hot tub salesman employed emotional manipulation, including sharing “personal” stories about his daughter’s student loans, which Jesse later recognized as classic influence tactics.
Lesson: High-pressure sales settings are engineered for impulse, and recognizing manipulative tactics can help you avoid mistakes.

“I made the decision because we were just coming off of a fun mountain retreat with friends… It’s hard to recreate those vacation vibes in just everyday life.”
— Jesse [39:32]

Insights & Strategies (44:12–46:32)

Em adds that “frictionless” buying online amplifies these impulse vulnerabilities. She recommends the 24-hour rule (save to cart and sleep on it), which leads her to cancel most impulse purchases.
The “cooling-off” period: Some purchases have grace periods by law—Jesse notes this applies to his hot tub state and to vehicles/insurance in some cases.

Doug’s Tale: Designer Frames, Emotional Shopping, and Buyer’s Remorse (46:58–49:07)

Doug reminisces about purchasing $1,400 antique eyeglasses during an emotional period, tying it to the “I’m making adult money now” trap. Years later, he realized the opportunity cost and regrets the purchase—a tale of patience, context, and monetary wisdom gained late.

“There are some stories that aren’t horror stories until years later when you realize what the opportunity cost was…”
— Doug [48:34]

Joe’s Tale: The Midas Muffler Upsell – Recognizing a Rip-Off (49:26–52:42)

Young Joe succumbs to an upsell at a car shop, buying unnecessary upgrades for an old Monte Carlo after a charismatic worker sells him on restoring it. The receptionist covertly offers him a coupon, wordlessly signaling he’s being taken advantage of.

Key Takeaways and Memorable Quotes

On the danger of “I deserve it”:

“The most dangerous phrase for a broke person to say is, ‘I deserve it.’”
— Joe [49:26, referencing Buffy Purcell]
On “good debt” and paying off her mortgage:

“Our whole goal was being debt free. I wanted freedom, total freedom. I didn’t want to owe anything to anyone…”
— Em [27:26]
On rationalizing payments:

“It was my first school of hard knocks lesson in the way that hard sales tactics work.”
— Jesse [39:37]
On survivable mistakes:

“Most of these stories are stories that really burn you because you spent when you shouldn’t have spent… but hopefully we learn from them.”
— Doc G [51:45]
On estate planning inertia:

“If you don’t have a will, the state has a will for you. You do have a will.”
— Joe [16:05]

Notable Quotes with Timestamps

On the illusion of perfection:
“People think that for you to get as far as you have with your money, like you’ve just done everything perfect. M. Everything’s perfect for Em and her family all the time.”
— Joe Saul-Sehy [05:13]
On the comfort of finally planning for the future:
“It shocked me how much better I felt. I was blown away by how all of a sudden… I felt so good. I was like, I never thought I’d feel this good. I thought I’d feel morbidly bad because I was acknowledging death…”
— Joe Saul-Sehy [13:01]
On opportunity cost:
“If Emily now knew what I knew back then and I invested $550 every month, I mean, we’re talking serious money.”
— Em [21:51]
On succumbing to sales tactics:
"It was my first school of hard knocks lesson in the way that hard sales tactics work. And I can still remember this sales guy sitting in my kitchen... telling me about his daughter's student loans and how every sale is meaningful to him..."
— Jesse [39:37]
On learning from mistakes:
“You have to put your hand on the stove once to know to avoid the stove later on in life… Thank God this was a recoverable mistake.”
— Doc G [22:31]

Important Timestamps

08:21: Doc G’s family power-of-attorney nightmare
17:32: Em’s $60k Audi lease horror
39:16: Jesse’s “hot tub hustle” story
46:58: Doug’s eyeglasses emotional overshopping
49:26: Joe’s Midas muffler rip-off
51:45: Panel reflects on survivable financial mistakes

Actionable Lessons & Takeaways

Get your financial and estate planning done early, especially with children or dependents.
Beware lifestyle inflation and the trap of “I can afford the payment.” Assess the total cost and opportunity cost.
Recognize emotional and manipulative sales tactics—sleep on big purchases and create friction before you buy.
Don’t let media negativity or social comparison take you out of the game. Even if goals feel far off, progress is possible.
Remember, everyone makes mistakes—use them as tuition, not tombstones, for your financial journey.

Closing & Additional Resources

Connect with the guests:
- Em: “Hey Friend, It’s Em” on TikTok/Instagram
- Jesse: Personal Finance for Long Term Investors (podcast and Best Interest Blog)
- Doc G: Earn & Invest podcast
Join the Conversation:
- Share your financial horror stories in the Stacking Benjamins Facebook group (stackingbenjamins.com/basement)
- Submit questions via voicemail at stackingbenjamins.com/voicemail

Tales of Financial Horror (and how we exorcised them) SB1755

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Summary

Podcast Summary: The Stacking Benjamins Show

Overview

Key Discussion Points and Insights

Panel Introductions & Tone Setting (01:58–06:19)

Doc G’s Tale: The Perils of Estate Planning Delay (08:21–11:15)

Story (08:21–10:57)

Insights & Reactions (11:15–17:32)

Emily’s Tale: The $60,000 Car Lease – Chasing Validation Through Debt (17:32–24:58)

Story (17:32–20:01)

Insights & Reflection (20:01–28:02)

Jesse’s Tale: The Hot Tub Hustle – Impulse + Sales Pressure (39:16–44:12)

Story (39:16–41:51)

Insights & Strategies (44:12–46:32)

Doug’s Tale: Designer Frames, Emotional Shopping, and Buyer’s Remorse (46:58–49:07)

Joe’s Tale: The Midas Muffler Upsell – Recognizing a Rip-Off (49:26–52:42)

Key Takeaways and Memorable Quotes

Notable Quotes with Timestamps

Important Timestamps

Actionable Lessons & Takeaways

Closing & Additional Resources

Summary

Podcast Summary: The Stacking Benjamins Show

Overview

Key Discussion Points and Insights

Panel Introductions & Tone Setting (01:58–06:19)

Doc G’s Tale: The Perils of Estate Planning Delay (08:21–11:15)

Story (08:21–10:57)

Insights & Reactions (11:15–17:32)

Emily’s Tale: The $60,000 Car Lease – Chasing Validation Through Debt (17:32–24:58)

Story (17:32–20:01)

Insights & Reflection (20:01–28:02)

Jesse’s Tale: The Hot Tub Hustle – Impulse + Sales Pressure (39:16–44:12)

Story (39:16–41:51)

Insights & Strategies (44:12–46:32)

Doug’s Tale: Designer Frames, Emotional Shopping, and Buyer’s Remorse (46:58–49:07)

Joe’s Tale: The Midas Muffler Upsell – Recognizing a Rip-Off (49:26–52:42)

Key Takeaways and Memorable Quotes

Notable Quotes with Timestamps

Important Timestamps

Actionable Lessons & Takeaways

Closing & Additional Resources