Jack Delosa built a $50M company by 27, lost it all to government regulation changes, accumulated $5M in survival debt - then came back stronger than ever. In this raw conversation, Australia's most followed business coach shares the brutal reality of scaling, the psychology of success, and why he'll never sell The Entourage despite multiple exit opportunities. Jack reveals his exact strategy for turning around $5M in debt, why "good times scare the shit out of him," the hiring framework that scales culture from 20 to 40+ employees, and why businesses grow MORE during hard times than easy times. Learn the psychology of the top 1% and their relationship with difficulty, plus the constraint-to-constraint framework for 8-figure scaling. This episode goes places most business podcasts don't - raw, real, and packed with actionable insights from someone who's been through hell and came back stronger. 00:00:00 - Introduction to Jack Delosa and his humble energy despite massive success 00:08:30 - From $50M company to $5M debt: The government regulation collapse 00:15:20 - The 3-year comeback strategy: How to turn around survival debt 00:28:10 - Building elite culture: Why The Entourage was 4th best place to work in Australia 00:42:00 - Why businesses grow more during hard times than easy times 00:48:30 - The $2.5B Minecraft exit story and why it led to depression 01:01:20 - Business scaling framework: Growing from constraint to constraint 01:18:45 - Top 1% mindset: Rewiring your relationship with difficulty 01:22:43 - Best advice from a PayPal seed investor: "To copy the greats is to not understand them" 01:25:00 - The defining trait of the top 1%: Seeing hard as a signpost you're on the right path Want to learn my exact strategy for building a successful property portfolio? Check out School of Property for a step-by-step investing blueprint that's helped thousands of Aussies start and scale their investments: https://schoolofproperty.com.au Follow me for more investing & business insights: Instagram: https://www.instagram.com/samgordonproperty Business: https://www.instagram.com/australianpropertyscout Podcast: https://www.instagram.com/thetoponepercentpodcast Follow Jack Delosa: https://www.instagram.com/jackdelosa #JackDelosa #BusinessGrowth #Entrepreneurship #Top1Percent #BusinessCoaching #Scaling #Leadership #AFRYoungRichList #TheEntourage #BusinessMindset #Resilience #EntrepreneurLife #BusinessStrategy #StartupLife #BusinessOwner #CEO #AustralianBusiness #PropertyInvesting #BusinessPodcast The content provided on this podcast is for informational purposes only and should not be considered as financial, business, or legal advice. The hosts and guests of the podcast are sharing their personal opinions and experiences, which may not be applicable to your unique situation. We strongly recommend that you seek the advice of a qualified financial advisor, business consultant, or legal professional before making any financial or business decisions. Reliance on any information provided in this podcast is solely at your own risk. We make no representations or warranties as to the accuracy, reliability, or completeness of the information provided. All information is provided "as is" without any guarantees of completeness, accuracy, timeliness, or results obtained from the use of this information. Any references to specific financial products, companies, or services are for illustrative purposes only and do not constitute an endorsement or recommendation by the podcast or its hosts. By listening to this podcast, you agree that the podcast and its affiliates are not responsible for any errors or omissions, or for any actions taken based on the information provided in this podcast. Learn more about your ad choices. Visit megaphone.fm/adchoices