Success in Media Business and Overcoming Doubters

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The chapter explores the success story of William Randolph Hearst in building an empire through yellow journalism, acquiring media titles, entering the cable business, and expanding their portfolio. It discusses the importance of owning a strong thesis around media assets, drawing comparisons between successful businesses like Hodinkee and unsuccessful attempts like BuzzFeed. Additionally, it delves into personal motivations, work ethics, and the driving force that animosity towards competitors or critics can bring in the entrepreneurial journey.

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