I started and bootstrapped my second tech startup 8 years ago. We saw constant growth and reached just under 2M in sales until 2012 when we were hit by some challenges out of our control, including a bogus patent troll suit (which was eventually dismissed). Being bootstrapped, we just didn't have too much of a safety net in place to deal with these issues. While I have been able to hold things together from then to now, it has been more 'survival mode' than anything else. I have tried a LOT of things, but it's all been on the cheap. Advisors have told me to cut back which I have. Since then it has been a constant struggle and sales have been heading downward. I am pretty much alone as I have no investors. While I still think our company has a lot of potential, I have not yet been able to make a rebound happen. Our direct competitors are funded companies, and it's tough to go up against them without any funding and in a defensive position. The investor types I talk to have always communicated that we make too much for an angel and not enough for a VC. I have cut back pretty much all I can (we have always been pretty lean anyway). I have what I think are some great and innovative ideas, but I don't feel I have the time and funding to make them happen. On my own, I am feeling less and less we will be able to bounce back. I have no idea what I will do if I have to shut things down. I have literally poured my life into my business to keep it going, so stakes are incredibly high for me and my family. I want to be pro-active and make sure I have things in order so that if it gets to the point where it needs to be shut down, I am not scrambling to find a plan B. Additionally, I am not even sure how to shut down a business of this magnitude with many nuts and bolts. Does it have to go bankrupt? Do you just shut down the website? Has anyone else gone through something similar?

I'm sorry to hear that. I completely understand what it's like to pour your heart and soul into a business for many years, because I've done it several times. Some were successful in some were not.

Here's what I recommend:
1) You may have already done this, but if not deeply analyze if there is some sort of pivot you can do to increase sales without having to take investor money. This recent Entrepreneur magazine article talked about how I did this with a site that was on the rocks:

2) See if you can bring on a cofounder type partner,who has specialized knowledge in the crucial areas that you lack that are holding sales from growing. In exchange for a significant amount of equity, they can pour a bunch of new energy and enthusiasm into the company, which might be the thing you need right now after 8 years.

3) if that doesn't work: every business has competitors.The assets your company has are usually significantly more valuable to a competitor,then if you were to attempt to sell them to a new entrant to the market. For example, you probably have a significantly sized customer email list, that a competitor would be interested in purchasing. You may control certain parts of the market that a competitor does not, which would make it desirable to them. If you haven't done so already, I would recommend contacting the other CEOs in your industry and finding out what their situations and needs are.

4) if that doesn't work, then you would look at what pieces of the company you could sell to others that might still have value, before shutting it down.

I hope this helps.

Answered 7 years ago

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