Help: My startup is great but Im suffering. I'm a sole founder and been in and out of depression. I don't think it's supposed to feel this way. Maybe I'm not suited for this. Shutting down is impossible to conceive of. Where do I draw the line?

There are business brokers out there that can help sell your company to entities that are more willing to operate companies that generate cash flow

Get some friends and do fun stuff when your not working. Enjoy life, live, laugh, adventure. Life isn’t all about work; your company is important and not only provides self fulfillment, but also a much needed income; enjoy some of your success man, just make sure its not in excess. 🙂

Running a profitable but small B2B as a solo founder, currently 4 years in.

I’ve been there for the first few years and only recently starting to come out of the depression. In my case the pressure was put on by one individual at our largest enterprise client – once I decided to stop working with that person then I felt more relaxed within a few days. Fast forward a year, the client is still with us and the individual at that company has been fired.

I still have days of doubt and depression but they are in the minority now. I’m still contemplating a choice between:

Continuing on my own and growing the business at my own pace.
Selling (which will commit me to at least 3 years of co-operating/working with the new buyer).
Stop all new development and sales, in effect stopping new business (but maintaining existing revenue) and allowing existing clients to wind-down and move elsewhere in their own time.

Option 3 has the benefit of allowing me to continue receiving income for another 6-12 months (whilst people move away), but removes all stress once the decision is made and communicated to them. It also cuts all my development cost so for those 6-12 months it’s 95% profit which would be enough to live off for 5 years. Only problem is I’m in my early 30’s so I’d need to get into work/new start-up again to live beyond this.

In any case, you probably have the same options above, and you aren’t alone in going though this. Just think about your priorities and remember that you are the only person who can look after you.

This is why co-founders can be great. If your startup is profitable and has employees. Can you find a passionate one to bring up as co-founder? or failing that someone from outside? Co-founders don’t have to be at the beginning.get a co-founder/coo role. Give them what they would have had if they started with 10% shares, pre any dilution. Over three year vest one year cliff. Make sure a laser checks it out. Probably helpful if you can be open and tell your new co-founders about the depression so they can help.