Financial Audit with Caleb Hammer
Episode: "Most Batsh*t Crazy Woman I’ve Ever Met | Financial Audit"
Guest: Char (42, Orlando, FL)
Release Date: September 24, 2025
Episode Overview
In this episode, Caleb sits down with Char—a 42-year-old operations coordinator, property manager, and wedding officiant from Orlando, Florida. The conversation journeys through Char’s highly chaotic financial situation: massive credit card debt, wild spending habits, a side business that barely breaks even, sporadic attempts at financial organization, and a unique ability to justify nearly every expense on adventure and self-fulfillment. Caleb attempts to untangle Char's finances and instill some financial sense amid her relentless jokes, tangents, and quirks.
The result is both a financial intervention and a reality check for anyone wondering how quickly unchecked spending, creative budgeting, and denial can spiral into a financial trainwreck. The episode is a wild mix of comedy, financial education, and unfiltered honesty.
Key Discussion Points & Insights
1. Char's Income and Employment (00:47–07:16)
- Primary Job: Operations coordinator and property manager, making $44,000/year (pre-tax), with some bonuses.
- Side Hustle: Owns a wedding officiant business—highly seasonal, variable income; reported $40,000 in gross revenue last year but expenses/nebulous accounting make net income unclear.
- Withholding Taxes: Char withholds extra tax from her main job to "cover business taxes," confusing estimated payments and effective tax strategy.
- Financial (Dis)Organization: All business tracking is end-of-year, on Google Sheets—major gaps, missing logic. No CPA; uses TurboTax.
"You must not make a lot of money. What does the second job make?" – Caleb (03:21)
"Sometimes I make more than my full time job." – Char (03:25)
- After much confusion and searching through emails and tax forms (07:03–15:01), it was revealed that after expenses, her business had almost no profit.
- IRS audit risk and legal issues are a theme; Char admits to ignorance.
2. Financial Habits & Mindset (09:39–19:02)
- Disorganization & Denial: Char consistently cannot immediately answer questions about income or expenses.
- Business as Hobby: Despite counting the officiant business as work, Char spends ~25 hours/week on it for very little real profit (sometimes less than $1/hour).
"You’re making a dollar an hour on average." – Caleb (18:01)
- Emotional Approach: Char laughs off or jokes about mistakes but admits she’s “not business-minded.”
- No Clear Motivation: Char’s financial chaos is partly driven by lackluster ambition to improve, lack of accountability, and treating work/hobbies indistinctly.
3. Monthly Spending & Debt Crisis (20:11–31:35)
- Spending Exceeds Income: Last month, Char spent ~$9,600 while bringing in ~$7,500—overspending by $2,000 every month.
- Credit Cards as Crutch: Reliance on debt to sustain her lifestyle.
- Debt Load: Over $55,000 in total debt, largely on credit cards at high interest, and a $27,000 auto loan.
"That is $1,772.60 just in minimum payments to debt… That is 72% of your income." – Caleb (91:30)
- Family 'Tithing': Sends ~$50/week to her dad despite dire finances. Loans money to her brother with no questions asked.
4. Psychology & Justifications (31:36–40:04)
- Quirky Deflection: Char frequently jokes or digresses when pressed—self-described "giggler" and “quirky millennial.”
- Justifies Every Expense: Vacations, Universal Orlando passes, African safaris, and even plastic surgery (“tummy tuck”) are rationalized as “musts.”
- Enabling Poor Family Dynamics: Continues to tithe/give money to family despite inability to afford it.
5. The Credit Card Shuffle (33:15–46:29)
- Balance Transfer Addiction: Runs a constant cycle of moving balances between cards to maintain 0% interest for a short time, making little progress.
- Minimum Payments Trap: Making only minimums, accruing hundreds in fees and interest, cards are routinely maxed out or over-limit.
- No Plan to Stop: Admits to continuing the pattern out of habit and lack of alternatives.
"You're never making progress in your life whatsoever, ever? …You’re okay with that?" – Caleb (45:15–45:23)
"No." – Char
"Then why do you do it?" – Caleb
6. Root Causes and Family Influence (49:32–50:45)
- Financial Illiteracy in Family: Grew up in a family that didn’t pay taxes, had under-the-table jobs, religious reasoning (Jehovah’s Witness) and general denial.
- Inherited Patterns: Admits to picking up bad habits from parents, extensive financial dysfunction modeled in childhood.
7. The Lifestyle Trap (50:52–67:07)
- Unnecessary Luxuries: Regularly purchases premium entertainment (Halloween Horror Nights, Hulu, Paramount, etc.), frequent eating out, international travel.
- Plastic Surgery Debt: $6,000+ in affirm/loan for a “tummy tuck,” justified both by appearance and medical relief.
- Car Loan: $27,000 left on a Honda CRV, despite financial struggles.
8. Attempts at Solutions, But Inaction (85:23–95:04)
- Considers Downsizing Cars: Toyed with trading in for a cheaper car, but reluctant.
- Resistant to Roommates/Downsizing: Jokes about solution instead of embracing it.
- No Retirement Savings: Has no investments or financial plan beyond bare survival.
- Reluctantly Agrees to Side Hustle: In the post-show, is tasked with calling for a new side hustle to attempt to rescue income shortfall.
9. Financial Reality Check (95:26–95:36)
- Hammer Score: 1 out of 10, with all categories essentially bottomed out—no savings, no retirement, hopeless debt, unsustainable lifestyle.
Notable Quotes & Memorable Moments
-
Income and Cluelessness
"I actually didn't realize how bad my debt was until I pulled everything and I calculated it."
– Char (00:03)"I'm not trying to do math here."
– Char (00:08, and several times throughout)"You’re making a dollar an hour on average.”
– Caleb (18:01) -
On business organization:
“I have my little thing… to do process. So, like, I know that I’m supposed to be doing this, but I’m a slacker.”
– Char (06:11)“I’m gonna die. My theme song after filming an episode like this sounds like a trigger being pulled.”
– Caleb (53:58) -
On mindless spending:
“I like going on vacation.”
– Char (23:31)“So the Hyatt, all of it was a thousand dollars.”
– Char (66:11) -
On supporting her family despite debt:
“Although I am in financial crisis, I feel like he (my dad) needs some money more than I do.”
– Char (24:15) -
On the debt transfer cycle:
"Instead of paying that $60 a month… you do the balance transfer and it’s like a 1% transfer fee. So you pay like $200…”
– Char (48:00)
“You’re just getting that every few months. So no matter what… you are accruing interest regardless. This doesn’t make financial sense.”
– Caleb (39:32) -
On justifying plastic surgery:
“Tummy tuck. I got a tummy tuck in December.”
– Char (54:38)
"Not only did it make my stomach look… I just feel so much better about myself.… I haven't had back pain in eight months.”
– Char (57:15) -
On her own ambitions and accountability:
“There’s nobody to hold me accountable. My two cats… shouldn’t need [that] bad.”
– Char (62:32)“Is there nothing to care for, nothing that you are ambitious towards? I don’t know. Is there no incentive here?”
– Caleb (61:55)
Timestamps for Important Segments
- Intro & Guest Background: 00:00 – 01:15
- Income Breakdown & Business Chaos: 01:31 – 07:03
- Tax and Business Tracking Issues: 02:42 – 08:06
- Trickling Into Debt Discussion: 16:16 – 22:08
- Monthly Budget Reality Check: 20:04 – 21:06, 91:30 – 92:00
- Justifying Gifts to Family: 23:33 – 25:47
- Credit Card Balances and Transfers: 33:15 – 46:29
- Vacations & Spending Rationalization: 50:52 – 67:07
- Plastic Surgery Admission: 54:13 – 58:00
- Car Loan, Downsizing, and Reluctance: 83:35 – 87:53
- Final Tally: Living Expenses, Budget, and Score: 90:29 – 95:36
- Financial Score & Episode Wrap: 95:26 – End
Episode Tone & Takeaways
- Chaotic, comedic, and intermittently exasperated. Char’s self-deprecating humor, denial, and relentless tangents provide laughs but also underline a serious message: self-delusion, avoidance, and “quirkiness” do not substitute for responsible financial behavior.
- Relatable for many who struggle with debt, organization, and denial—but also a stark warning about the slippery slope of lifestyle inflation and living on credit.
Caleb’s Parting Message
“No more. These are your statements.… You need to double your income at a minimum basis. This is crazy. That’s where we are. I’m sorry. There’s no debt payoff strategy—we need to figure out the income thing.” (95:04)
Bottom Line
Char’s case is a spectacular example of how unchecked spending, lack of systems, and avoidance can turn even a decent income into a treadmill of debt and anxiety. The entertaining banter cannot mask the urgent need for change: serious downsizing, extra work, actual debt repayment—not just more creative accounting and excuses.
For listeners:
You’ll laugh, you’ll cringe, and you might just recognize a little of yourself in Char’s financial chaos. Let this serve as both entertainment and a cautionary guide.