Ask Jerry

Ask Jerry

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A weekly advice column on leadership and radical self-inquiry.

Ask Jerry is a series of conversations between Andy Sparks and Jerry Colonna answering questions from the readers. The authors discuss behavioral patterns and psychological habits, answering questions like how to manage feelings of resentment to your Co-founder or how to find purpose in life. So if you understand the value of self-discovery, subscribe to the words of wisdom from Jerry Colonna.  




Ask Jerry is produced by Andy Sparks, featuring Jerry Colonna. Andy Sparks is executive coach-in-training, writer, and a former CEO at Holloway and COO at Mattermark. He coaches startup leaders and studies relationships at work with the ultimate goal of figuring out “what separates co-founders with healthy relationships from co-founders with toxic ones. Jerry Colonna, founder and CEO at Reboot, is known as Silicon Valley’s leadership coach and “CEO whisperer”. He is helping executives to become better leaders through “radical self-inquiry” and is considered as one of the “most desired” coaches in the world of startups.


The newsletter is part of the Every - a writer collective that offers a variety of business/productivity newsletters as a bundle. By subscribing to a free version you can expect to receive a newsletter two times a month - usually on Tuesdays, sometimes on Wednesdays. The free version also gives you the weekly Sunday Digest with summaries and links to all the content from the bundle, that was published throughout the week.

If you wish to silence some of the newsletters you can always change preferences on your account page (a link is being sent with every issue). You can opt-out from everything except Ask Jerry, or - you can go all in and decide later!


The paid subscription of Every bundle costs $20 (or $1 for 30 days trial and then $200 per year) and gives you access to the most in-depth articles from a variety of other business/productivity newsletters.

If you’re only interested in Ask Jerry - the paid subscription won’t get you any perks, but you should definitely consider exploring the other newsletters in the bundle. If you find what you like - the price will be worth it!

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