How to Make Money After Prison

When you come home, everybody tells you to get a job. But what job, and what if you want more than a paycheck? Hasan, Brad and Ross get real about making money after prison: the first paycheck, trades and licenses, using AI the right way, starting small with what you have, and what "comfortable" actually costs today. No hype and no guarantees, just what worked, what didn't, and what we'd do differently. In this episode: The first paycheck after prison, and what it felt like 5Q: By the Numbers Why we pay for mentors and knowledge How to use ChatGPT for research, and why you make it show its sources First job home: license, CDL and trucking Testing a business idea before you spend real money The middleman model, and how dealer buying works Job, career or business, and what it costs to live comfortably Facts on screen are checked against primary sources: U.S. Bureau of Labor Statistics (OEWS May 2025, Business Employment Dynamics, CPI), Florida HSMV, GSA/SAM.gov, AuctionACCESS and the EEOC. Pay and fees vary by state and change over time. This is a candid conversation, not legal, financial or career advice. There's always a fifth quarter. 0:00 Cold open: what it takes to start 0:41 Welcome: how to make money after prison 0:54 The first paycheck after prison 3:15 5Q: By the Numbers 8:16 Paying for mentors and knowledge 18:34 Getting started: phones, apps and local events 22:50 How we started using AI 29:01 Using ChatGPT the right way 35:13 Make AI show its sources 40:04 First job home: license, CDL and trucking 45:00 Is everyone built to be an entrepreneur? 46:03 Test a restaurant before you open one 48:50 A $200 lawn-care start 50:56 The middleman model 53:50 Buying cars for dealers 57:02 Learning any business with AI 59:25 Job, career or business? 1:01:59 What does "comfortable" cost? 1:03:05 Raising a family: the real numbers 1:04:43 RSA of the Week 1:06:01 Final word: there's always a fifth quarter