In this post Justin Jackson shares his struggles, doubts, and uncertainties about where to take his startup. Sometimes we put too much financial pressure on a startup too soon and it fails — not because of lack of product/market fit, but because of financially poor choices.

It’s been exciting to build and grow our app on the side. But it’s also been hard. With hundreds of paying customers, we’re dedicating more of our time to serving them. But, the business isn’t earning enough to pay us for our time.

It’s been particularly challenging for me. Since 2016, I’ve supported myself with M4Devs and other courses. But my revenue’s fallen this year as I’ve dedicated more time to Transistor.

Justin Jackson shared some personal insights and lessons learned in this post — and quoted Des Traynor, co-founder of Intercom saying:

A founder is spending 60 months of their best years in their startup (instead of their career). That is a substantial upfront investment; it’s like a seed round, but instead of money, it’s your life.

And the bootstrappers dilemma…

Can I get this to scale, while paying my bills, without burning out? This is why many founders end up raising venture capital.

In this special episode of JS Party, we’re sharing a full-length episode of our new show, Away from Keyboard. This show explores the human side of creative work. In this episode, Tim talks with Justin Jackson about his parents, dealing with depression, and a new business he’s co-founded.

I first heard of Justin Jackson about six years ago. Back then, he was consulting full-time for a company with the dream of going independent. Fast forward to 2018, and after building a successful business, he’s now embarking on a new adventure. Justin talks about his parents, dealing with depression, and a new business he’s co-founded.