I Lost $65 Million In One Day… And It Changed Everything- Dan Fleyshman episode artwork

EPISODE · Jan 23, 2026 · 1H 22M

I Lost $65 Million In One Day… And It Changed Everything- Dan Fleyshman

from Earn Your Leisure · host iHeartPodcasts

In This Earn Your Leisure Interview, We Sit Down With Dan Fleyshman To Break Down One Of The Most Unconventional Business Journeys Ever. From Becoming The Youngest Person In History To Take A Company Public At 23, To Building Multimillion-Dollar Businesses, Dan Shares What It Really Takes To Win Early—and Stay In The Game Long Term. We Dive Deep Into The Real Pros And Cons Of Running A Public Company, How A $2.4 Million Investment Turned Into A Six-Figure-Per-Week Poker Business, And Why Losing $65 Million In A Single Day Ended Up Being The Best Thing That Ever Happened To Him. Dan Also Explains Why Most Companies Fail, The Importance Of Capital Management, And Why Creative Marketing Is The Only Way Startups Can Compete With Conglomerates. Dan Breaks Down His 40/40/20 Investing Strategy, How He Identifies Winning Companies, The Business Model Behind Influencers Making Real Money, And How To Successfully Pitch Brands. This Episode Is A Masterclass On Risk, Branding, Social Media, And Building Sustainable Wealth In A Noisy World. Invest Fest Tickets: investfest.com #EarnYourLeisure #DanFleyshman #Entrepreneurship #Investing #BusinessGame #IPO #PersonalBrand #SocialMediaBusiness #StartupLessons #WealthBuilding #MarketingStrategySee omnystudio.com/listener for privacy information.

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I Lost $65 Million In One Day… And It Changed Everything- Dan Fleyshman

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This episode was published on January 23, 2026.

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