Dec. 9, 2025

From Streets to Success: Jerry Brazie on Building $500M in Revenue

From Streets to Success: Jerry Brazie on Building $500M in Revenue

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 From Streets to Success: Jerry Brazie on Building $500M in Revenue | The Undiscovered Entrepreneur

 
Episode Description
 
Jerry Brazie went from living in a $25/week flophouse at 17 to building and selling a dozen businesses generating nearly $500 million in revenue. In this raw, unfiltered conversation, Jerry shares the pivotal moment at 14 that changed everything, why "everything is your fault" became his superpower, and the brutal truths about entrepreneurship that influencers won't tell you.
 
Key Takeaways
 
• The "everything is your fault" mindset that transforms victims into builders • Why waiting for the perfect time guarantees failure • How perspective becomes an entrepreneur's greatest superpower • The loneliness of entrepreneurship and how peer groups solve it • Why passion-based businesses often fail (and what to do instead)
 
Time Stamps
 
[00:00] Introduction and Jerry's incredible backstory

 [04:00] The pivotal moment: beaten and left for dead at 14

 [08:00] Why "everything is your fault" is actually empowering 

[13:00] The mistake new entrepreneurs make when seeking advice 

[25:00] Breaking the perfectionism trap that keeps people stuck 

[33:00] Dealing with entrepreneurial loneliness 

[38:00] The power of peer-to-peer mentorship groups

 [43:00] Battling imposter syndrome even after massive success 

[46:00] Six-month goals and launching The Kronos Group
 
Guest Bio
 
Jerry Brazie is a serial entrepreneur, 15-year-old high school dropout, and founder of The Kronos Group peer-to-peer mentorship program. With 30+ years building businesses across transportation, real estate, and consulting, Jerry has managed 10,000+ employees and generated $500M+ in revenue.
 
Connect with Jerry
 
Website: kronosgroup.org Podcast: The Kronos Group Podcast (formerly The Jerry Brazie Podcast) Ideal for: Business owners doing $1-25M in annual revenue
 
Mentioned Resources
 
• Peer-to-peer business groups for entrepreneurs • The Kronos Group mentorship program
 
#Entrepreneurship #BusinessGrowth #StartupAdvice #Mindset #PeerMentorship #SmallBusiness #EntrepreneurLife #OvercomingAdversity #BusinessPodcast #SuccessStory #GenerationalPoverty #WorkEthic #ImposterSyndrome

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