Mark Suster is a former entrepreneur, now VC so he really has been on “both sides the table”. His blog is an amazing source content, mostly about venture capital and entrepreneurship, so as his newsletter.
Tressie is no longer publishing this newsletter -- but she has a different one called "essaying", here: https://narrowscale.com/newsletters/essaying-by-tressie-mcmillan-cottom.html
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“My weekly newsletter is full great things to read (some but not all which were written by me) and GIFs and the occasional product endorsement. It arrives in your inbox on Fridays, just when you’ve run out internet for the week.”