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249 · Valet Driver Turns $20K into $11Mil over 6 years After Wipe Out w/ Jack Kellogg

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Starting out juggling multiple jobs as a valet driver, firefighter and entrepreneur, Jack Kellogg at 18 years of age about 6 years ago dreamed of financial freedom, became laser-focused on saving money and learned everything he could about the stock market before turning to penny stocks.

Jack’s intense drive for success pushed his mental and physical health to unhealthy levels as he managed hundreds of trades, and at times in illiquid, unregulated securities that often saw hundreds of percent increases, quickly followed by spectacular collapses within just a few weeks.

This multifaceted discussion takes us inside Jack’s journey, which was met with setbacks and struggles, along with wisdom gained earlier than usual for someone so young.


Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice.

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Topics & Timestamps:

  • 0:00 Jack’s background and how he got into trading
  • 5:15 His parents view of trading and early goals
  • 6:25 What makes trading fascinating for Jack
  • 7:25 Is trading lonely for him? Support network
  • 9:00 Quick and easy profits are disadvantageous
  • 10:45 His friend’s and family’s views of penny stocks
  • 11:36 Issues with penny stocks
  • 18:10 Perceptions of penny stocks and why trade them
  • 20:42 Liquidity issues and how it changes over time
  • 23:30 Jack’s strategies and what he looks for
  • 29:00 Jack’s losses due to liquidity issues
  • 35:50 Use of leverage
  • 37:10 Holding penny stocks for days or weeks
  • 40:10 Shorting penny stocks
  • 42:15 Mindset of trading
  • 43:15 Personal care, sacrifices and illness
  • 49:13 $20,000 to $11 million in just 5 years
  • 52:00 Enjoying his winnings
  • 54:00 Advice for traders
  • 55:45 How to contact Jack

Jack Kellogg

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