Since launching With Jack I’ve stuck to semi-regular updates. Usually I write a blog post every fortnight or so, but life got in the way.

3 months ago I wrote With Jack’s year in review post. This was after only 4 months in business—1 of which was a soft launch. After putting my 81st customer on cover this week, I looked at some of the same figures that lead to that post.

Whenever people ask, “How’s Jack going?”, I’m never sure what to respond with. Do I tell them how many customers I have? Focus on the conversion rate? Or do I be upfront and say “It’s going well, but it’s not yet supporting me full-time”?

In August I launched With Jack. I wouldn’t say I was embarrassed by it—I was proud to get to the point of shipping because it had been a long slog. But I purposely launched with a bare bones business model.

Last week I celebrated putting my 50th freelancer on cover, but I want to start at the beginning and share how I won my first three customers.