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    40 Year Old Is Making An INSANE Amount Of Money
    1:50

    40 Year Old Is Making An INSANE Amount Of Money

     344  views
    25 Year Old Gets Instant Karma After Lying To Caleb
    3:48

    25 Year Old Gets Instant Karma After Lying To Caleb

     6  views
    40 Year Old Is Stuck Paying Off His Girlfriends Credit Cards
    3:30

    40 Year Old Is Stuck Paying Off His Girlfriends Credit Cards

     53.1K  views 67 comments
    31 Year Old Drives Caleb Into Insanity
    2:56

    31 Year Old Drives Caleb Into Insanity

     276  views
    This Guest Tested Caleb's Patience A LOT
    2:29

    This Guest Tested Caleb's Patience A LOT

     452  views
    29 Year Old In So Much Debt He Needs To Sell His House
    4:21

    29 Year Old In So Much Debt He Needs To Sell His House

     267  views
    40 Year Old Refuses To Plan For His Future
    4:16

    40 Year Old Refuses To Plan For His Future

     233  views
    He Lost $30,000 Trying To Mine Crypto
    3:35

    He Lost $30,000 Trying To Mine Crypto

     320  views
    40 Year Old's Car Loan Should Be Illegal
    1:50

    40 Year Old's Car Loan Should Be Illegal

     232  views
    40 Year Old Is Straight Up Lying To The IRS
    3:44

    40 Year Old Is Straight Up Lying To The IRS

     244  views 3 comments
    36 Year Old Only Has A Tiny Little Retirement Fund
    2:36

    36 Year Old Only Has A Tiny Little Retirement Fund

     203  views
    Caleb & Nurse Fight For 5 Minutes Straight
    5:35

    Caleb & Nurse Fight For 5 Minutes Straight

     229  views
    Guest Is Forced To Chop Up ALL Of His Credit Cards Mid Show
    3:24

    Guest Is Forced To Chop Up ALL Of His Credit Cards Mid Show

     205  views
    BDSM Girl Is Getting Dominated By Her Debt
    5:10

    BDSM Girl Is Getting Dominated By Her Debt

     228  views
    THE HIGHEST INTEREST RATE WE'VE SEEN ON THIS SHOW
    3:01

    THE HIGHEST INTEREST RATE WE'VE SEEN ON THIS SHOW

     1.05K  views
    Law Student Refuses To Make Credit Card Payments
    3:57

    Law Student Refuses To Make Credit Card Payments

     174  views
    Caleb Starts Destroying Her Excuses Out Of The Gate
    4:03

    Caleb Starts Destroying Her Excuses Out Of The Gate

     390  views
    29 Year Old Pisses Caleb Off Twice In 2 Minutes
    2:11

    29 Year Old Pisses Caleb Off Twice In 2 Minutes

     179  views
    29 Year Old Is Choosing His Vehicles Over His Baby
    4:13

    29 Year Old Is Choosing His Vehicles Over His Baby

     168  views
    She Is A PRIME EXAMPLE OF NOT A CREDIT CARD PERSON!
    2:30

    She Is A PRIME EXAMPLE OF NOT A CREDIT CARD PERSON!

     165  views
    Dominatrix Has Some HORRID Spending Habits
    2:43

    Dominatrix Has Some HORRID Spending Habits

     159  views
    Every Chance She Gets She Dives Deeper Into Debt
    3:25

    Every Chance She Gets She Dives Deeper Into Debt

     185  views
    The Day That Caleb Was Not The Mood
    4:27

    The Day That Caleb Was Not The Mood

     166  views
    Caleb DRILLS Guest For 4 Minutes Straight
    4:25

    Caleb DRILLS Guest For 4 Minutes Straight

     168  views
    Caleb Absolutely GOES OFF On Excuse Making Woman
    2:53

    Caleb Absolutely GOES OFF On Excuse Making Woman

     173  views 1 comment
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