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

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

Author: iHeartPodcasts January 23, 2026 Duration: 1:22:42

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 #MarketingStrategy

See omnystudio.com/listener for privacy information.


Hosted by Rashad Bilal and Troy Millings, Earn Your Leisure pulls back the curtain on the financial mechanics that power the worlds of sports and entertainment. This isn't just about headlines; it's a deep dive into the real stories of how money moves and how deals are made. You'll hear candid conversations that dissect business models and unpack the journeys of entrepreneurs, providing a street-smart education you won't find in a standard textbook. Each episode feels like a vital seminar, blending sharp analysis of current financial trends with the relatable context of pop culture. The Earn Your Leisure podcast, from iHeartPodcasts, operates on a simple premise: true financial freedom comes from understanding the game behind the game. It’s for anyone ready to look past the glamour and learn the practical strategies that build lasting wealth. Tune in for straightforward talk that makes complex business concepts accessible, always grounded in real-world examples from the industries that shape our culture.
Author: Language: en-us Episodes: 100

Earn Your Leisure
Podcast Episodes
Is the STOCK MARKET Being Manipulated? [not-audio_url] [/not-audio_url]

Duration: 5:58
Financial analyst Ian Dunlap exposes the "worst kept secret" on Wall Street: intentional market manipulation and rigged volatility. Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure Join the…
Is NOW the Best Time to Buy Gold? [not-audio_url] [/not-audio_url]

Duration: 3:43
Experts discuss why gold remains a top asset in a volatile market. Learn why its value transcends thousands of years. #marketmondays Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure Join the…
TSA Shutdown Wasn’t About Money… It Was About Control [not-audio_url] [/not-audio_url]

Duration: 9:38
"TSA crisis" is being utilized as an opportunity to normalize a militarized presence in public spaces, ultimately aiming for greater societal control rather than genuine security or financial efficiency. Subscribe and wa…
How to Perfect Your Elevator Pitch [not-audio_url] [/not-audio_url]

Duration: 8:10
Welcome back to EYL! In this clip, we are joined by the incredible Ashaala Shanae, who provides invaluable insights on how to perfect your elevator pitch. Whether you're preparing for Invest Fest or any other pitch scena…
I Don't Trust Any Jewelers" Here's Why [not-audio_url] [/not-audio_url]

Duration: 10:15
In this thought-provoking clip from "Black Out with Ian & Rashad," Rashad Bilal, Ian Dunlap, dissect the long-held beliefs around diamonds, wealth, and traditions. The conversation kicks off with Rashad Bilal questioning…
Are College Degrees are a Becoming Worthless? [not-audio_url] [/not-audio_url]

Duration: 10:33
The era of "go to school, get a job" is officially over. With AI looming and 30% of grads facing unemployment, the traditional education system has become a debt-fueled Ponzi scheme. Subscribe and watch more videos here:…
Stop Chasing Volatility Before You Get LIQUIDATED [not-audio_url] [/not-audio_url]

Duration: 5:58
If you aren't putting in 8–10 hours a day on the charts, you shouldn't be chasing market ramps. Ian breaks down why "safety" is the best play for 90% of investors right now. Subscribe and watch more videos here: / @earny…