Episode 596: Sam Parr ( https://twitter.com/theSamParr ) talks to Craig Fuller ( https://x.com/FreightAlley ) about how he turned dying hobby magazines into a cash flow machine.  — Show Notes: (0:00) Intro (2:45) Economics of long-haul trucking (3:36) Getting fired from the family business (5:30) Fuel cards for truck drivers (6:40) How FreightWaves hit $20M ARR in 2 years (9:08) Acquiring FLYING for $3.5M (12:14) Opportunity: Depressed media properties (16:02) From losing $8 per subscriber to profitability in 1 year (20:31) A media side hustle becomes a real estate main hustle (22:55) Craig's tolerance for being leveraged (25:32) Pre-selling $28M units pre-construction (28:51) Diversity, Asymmetrical risk, and generational security (31:11) Teams to diversify your time (34:21) Building a portfolio of hobby magazines (37:20) Content to commerce playbook (47:03) The story of William Randolph Hearst (51:32) What's the chase? (53:15) "The best thing to give a founder is an enemy" — Links: • FreightWaves - https://www.freightwaves.com/ • Knight-Swift - https://knight-swift.com/ • Firecrown - https://firecrown.com/ • The Chief - https://tinyurl.com/36khrt8y — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ — Check Out Shaan's Stuff: Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano