089: Tim Sykes | Trading Stocks, Travel, and Running A Charity

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Today I am joined by Tim Sykes, a well-know penny stocks trader and creator of the online community, Profit.ly. Tim is also a teacher, and the author of An American Hedge Fund. I wanted Tim to come on the show not just because of his success, but because of how fast he’s grown, his knowledge in the stock market, and how much he’s learned over the years. Philanthropy and volunteer work are also hugely important to Tim, and in this episode you’ll hear about his new love for travel because of his incredible charity.

In This Conversation We Cover:

  • [0:40] Growing up + what was instilled in his youth
  • [5:00] Turning his bat mitzvah money into one million dollars
  • [6:30] Why Tim thinks he was too full of himself
  • [7:21] Buying stocks in college
  • [9:30] Tips for penny stock trading
  • [11:19] Getting a cease and desist letter from Shaquille O’Neal
  • [13:35] Why penny stocks?
  • [16:42] Formula for success
  • [18:31] Social media strategy
  • [22:40] Successful media outlets and interviews Tim has had
  • [25:26] How often Tim’s on the road
  • [31:33] Traveling and charity
  • [32:54] Hard times + failures
  • [36:20] Not wanting to be a billionaire
  • [39:00] Play hard with Tim
  • [43:13] Rapid fire

Now accepting applications for the 2019 Work Hard Play Hard Mastermind. Go to workhardplayhardpodcast.com/mastermind or drop Rob a line at workhardplayhardpodcast@gmail.com to apply!

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Hi, I’m Rob!

Hi, I’m Rob! It has been said “You are not what you have learned, but what you’ve overcome.”


I have overcome my share of obstacles in order to architect the life of my dreams and uncover the key to lasting, meaningful success. Growing up in Queens (literally on the wrong side of the tracks), my early years were tumultuous, marked by hardship and violence.

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