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. 

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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"

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Links:

• FreightWaves - https://www.freightwaves.com/

• Knight-Swift - https://knight-swift.com/

• Firecrown - https://firecrown.com/

• The Chief - https://tinyurl.com/36khrt8y

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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/

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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