Matt Wensing

@mattwensing.bsky.social

Working @ Customer.io. Started two startups previously. I’ve been called relentless.

there's a buffer zone of 'good faith' that delays negative feedback for a while never assume that you must be doing the right thing because the other shoe hasn't dropped "but no one is complaining so far..." is very dangerous rationalisation

one thing i keep thinking about is how there is simply no way to design a constitutional system that can resist authoritarian incursion if participants in that system do not actually care that much

No data hunch: one driver of longevity is keeping a peak life experience ahead of you in your mind's eye. My current: the day we get to welcome all of our college-age kids back to our empty nest for an amazing Christmas. This will be December 2029.

When it comes to the war between Ukraine and Russia, let’s say you could not trust your own eyes—how does an American choose to trust the testimony and witness of Vladimir Putin over Volodymyr Zelenskyy?

It’s hard to reconcile these facts: I just spent 4 days skiing with 2 of our kids and it was one of the best experiences we’ll ever have together. This trip was spontaneous; ergo, it almost didn’t happen at all. How could I have almost missed out on something so amazing? It’s all so fragile.

How to close an enterprise deal: Bring in some new tech Quickly discover who loves it *Find out who doesn’t like it *Figure out who isn’t saying they don’t like it *Eventually learn why the CXO doesn’t like it *Get them all to like it Success Most people skip the * and fail.

Feels unlikely with 78 followers on here, but ... We are fielding offers from anyone that might be interested in buying Summit as tech ($0 MRR). A very well-featured low-code platform with 5 years of ideas baked in. If you or someone you know might be interested, holler.

Very surprising, but true: I've learned more in the last 3 days at Customer.io than I did in the last 30 days of running my own startup. When all else fails, one guiding light to follow: am I learning, am I growing, and if not, where can I go to keep learning and growing?