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Jeff Paccaro
Founder of Wingman and serial entrepreneur; guest on the episode to discuss entrepreneurship trends, the 'degenerate economy,' and risk-taking strategies for founders.
Best podcasts with Jeff Paccaro
Ranked by the Snipd community
Jan 15, 2026
• 38min
#841 The 9-5 is Dead, This is the Socially Acceptable Lottery Ticket
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Jeff Paccaro, founder of Wingman and serial entrepreneur, joins to explore the rise of the 'degenerate economy.' He discusses why traditional career paths are fading and how high-variance bets are gaining traction as people seek financial agency. Entrepreneurship emerges as a 'socially acceptable lottery ticket,' offering freedom despite high risks. The conversation delves into generational feelings of exclusion from stable jobs, financial nihilism, and the need for adaptability in a rapidly changing world. They encourage balancing safe bets with calculated risks for a thriving entrepreneurial journey.
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