I remember it vividly. About two years ago I was getting ready for bed and chatting with Kim about my side hustles. The optimism was high, and I said something like this:

I really think I could charge, man, maybe up to $25/mo for this!

Whatever the reason, I lacked confidence in my products. I was charging, at most, about $5/mo for my best tool. At one point I was on a pure “pay what you want” approach. While it did teach me a lot about pricing, it was yet another manifestation of my fragile belief in how good my products were.

Nine days ago, we rolled out a $169/mo plan for SendView.

Two days ago, we got our first user at that level.

What changed? Patrick.

He came on board a little over a year ago and, while he’s helped in a ton of ways, that’s the biggest. Because, yeah, I have a knack for products and an ability to built them simply and quickly. But he’s got a great instinct for the true value of those things in the market which has helped me overcome some of that self doubt.