E150 – Wisdom Comes From Bad Decisions: The Power of Trusting Your Judgement | with Tony DiMatteo

Self-proclaimed serial entrepreneur Tony DiMatteo is the CEO and co-founder of lottery.com, sports.com, and wintogether.org. Tony works on global initiatives and the development and execution for each of these companies’ long-term strategies, and on top of all this, he’s a sought-after industry speaker and thought leader. His biggest piece of advice for all entrepreneurs? Trust your judgment!


Tony says it’s imperative that CEOs and entrepreneurs always trust their judgment. Will your judgment always be right? Of course not! But making mistakes is how you grow and learn to sharpen your judgment – and that’s how you start to make better decisions.

In our conversation, Tony discusses the important role a CEO plays in a company and why it’s so important for them to take initiative and make fast decisions based on their judgment. Because at the end of the day, you’re the one who calls the shots, and wisdom is all about learning from experience.

In this episode:

  • [1:22] Tony gives us an overview of his entrepreneurial journey. 
  • [4:42] How did he muster up the motivation to ditch his role as an employee and step into CEO? Tony shares wisdom here. 
  • [7:31] Tony’s One Big Tip is to trust your own judgement – even though it may be wrong! He also explains that as CEO, you must defer praise and take blame. 
  • [12:02] Tony shares a story of a time when he didn’t trust his judgement but should have.
  • [17:55] Tony explains how wisdom comes from making bad decisions and learning from them.

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