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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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