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Timestamps :
00:00:00 - Intro
00:01:25 - Most upsetting guest
00:02:05 - Valid excuses for failure
00:04:35 - Worst money habits
00:08:22 - Common audit findings
00:08:32 - Why people stay broke
00:09:58 - Discipline vs small purchases
00:10:45 - When small purchases are OK
00:13:29 - Lessons on human nature
00:15:14 - Sponsor - RocketMoney
00:16:53 - Lack of responsibility
00:18:21 - Sympathizing with guests
00:19:24 - Breaking through with guests
00:20:32 - Items keeping people poor
00:22:39 - Accusations of exploitation
00:24:53 - Guest verification process
00:25:34 - Credit card usage mistakes
00:29:09 - Finance improvement tips
00:32:23 - Cash stuffing thoughts
00:32:47 - Are side hustles worth it?
00:34:38 - Tipping without servers
00:36:12 - Sponsor - ExpressPros
00:37:10 - Sponsor - Ramp
00:38:58 - Relating to show guests
00:41:47 - Hardest part of being broke
00:46:24 - Cost of pet insurance
00:49:39 - Your worst financial moment
00:57:54 - Caleb and relationships
01:01:27 - Sponsor - Bilt
01:02:31 - Sponsor - Shopify
01:03:46 - Life goals
01:09:49 - Asking people on dates
01:16:21 - Dating apps
01:18:40 - Finance in relationships
01:19:19 - Who spends more?
01:21:02 - Couple finance advice
01:24:05 - Victim mentality
01:26:45 - Thumbnail complaints
01:29:43 - Caleb's business growth
01:32:27 - Revenue streams
01:39:29 - Fear of dying poor
01:44:06 - Handling criticism
01:49:08 - Quitting YouTube
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