Alex Medick

November 30, 2023

I was on the Legendary Leaders Podcast

Hey friends -

I was recently on the Legendary Leaders podcast. The interview was published today. I haven't listened to it yet, so be sure to tell me if I sound like a nut job.

YouTube Link:

Legendary Leaders Pod Thumbnail.png

What We Cover

  1. An Entrepreneurial Mindset:
    • Alex has had an entrepreneurial spirit from a young age.
    • He shares experiences from his first startup, an independent record label, which faced both success and failure.
    • Alex emphasizes the importance of being fearless, taking risks, and not being afraid of rejection.

  2. From Music to Tech:
    • Alex transitioned from the music and entertainment industry to the tech and startup world. Reading Jason Calacanis' book "Angel," opened his eyes to the startup ecosystem.
    • Alex connected with Jason Calacanis, leading to his role at
    • It’s important to make the ask, overcome fear of rejection, and continuously take risks in your career. Alex is the president of Inside because he proposed the idea of leading the company to Jason.

  3. Lessons Learned Early On:
    • Alex reflects on the failures of his first startup, identifying key lessons learned.
    • The importance of having a clear leader in a company, mastering finances, and learning to say "no" are crucial.
    • These lessons shape Alex's approach to leadership and decision-making in his current role.

  4. Ingredients to Success:
    • Time management, prioritization, and the concept of essentialism (less is more) are critical ingredients in Alex’s success.
    • Alex encourages anyone early in their career to focus less on talking and more on executing. Be willing to do what others fear, and prove yourself through action.

  5. More on Mindset:
    • See opportunities where others might not.
    • Be willing to take risks.
    • Push yourself past the fear of failure
    • Don’t confine your idea of success to a narrow definition.
    • Alex’s passion is music, but the advice of “follow your passion” isn’t the only way to find success. He pivoted to finding success in the media world.

  6. Time Management as an Operator:
    • An operator at a startup has to wear many hats.
    • Right now, Alex has simplified his decision making by prioritizing revenue and subscriber growth.
    • Alex’s top time management strategy? Time blocking.

Thanks for listening/watching! 


About Alex Medick

Dad, Entrepreneur // Building INSIDE