How'd it Happen?

Jason Feifer - I Can't Wait to do This a Second Time [Episode 356]


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As entrepreneurs, we tend to think that the world is full of competition and that certain markets are too saturated for us to stand out, but the truth is that although the world is full of people, that doesn’t mean it’s full of competition. Chances are, what you need to do to stand out from the crowd isn’t as challenging as you think it is. It just means you need to serve people’s needs and do it in a way that is better than most. Today’s guest explains why he quit his unfulfilling job to pursue freelance writing and landed an opportunity to write for the Washington Post with minimal experience and zero connections.

Jason Feifer is the editor-in-chief of Entrepreneur Magazine, author of the book “Build For Tomorrow”, a startup advisor and host of the podcasts Build For Tomorrow, and Problem Solvers. LinkedIn named him a “Top Voice in Entrepreneurship” for 2022. 

In this episode, Jason and Mike discuss the topic of entitlement, why boundaries are not what they seem, and why Jason believes in the power of just getting someone on the phone. Jason shares his story of how it happened for him and his entrance into the entrepreneur world. Jason had an overwhelming feeling that there was a gap between the work he was doing and what he was capable of, so instead of staying stagnant and working at the level that someone else has placed him in, he bet on his ability and his hustle. Jason provides insight on how to pitch yourself even if you have no connections and very little experience.

Key Highlights:

  • Jason’s background before Entrepreneur Magazine
  • Why Jason left his job to pursue freelancing
  • Boundaries are not what they appear
  • How Jason got to write for the Washington Post with little experience and no connections
  • How to pitch properly and what Jason would look for in a pitch
  • The meaning behind the phrase “I can't wait to do this a second time.” 
  • 4 phases of change according to Jason: panic, adaptation, new normal, wouldn’t go back
  • Jason’s dominant question: "What am I missing?”

Episode resources:

Check out episode 198: Jeff Peterson, I Don’t Call Myself an Entrepreneur (#198)

Connect with Jason Feifer:

Twitter: @heyfeifer

Instagram: @heyfeifer

Facebook: Jason Feifer

LinkedIn: Jason Feifer

Website: jasonfeifer.com

Get Jason’s book: Build For Tomorrow

Check out Jason’s podcasts: Build For Tomorrow and Problem Solvers

To Connect with Mike:

  • Website
  • LinkedIn
  • Instagram
  • Twitter
  • YouTube
  • Coaching
  • Get Mike’s book: Owner Shift

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How'd it Happen?By Mike Malatesta

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