From Rags to (hopefully) Riches

1. Be as transparent with your employees and other stakeholders as you can be. At one point, we had to tell everyone in the company that coming to work was optional and that the next payroll was in doubt because of our cash issues. Even though it was bad news, they appreciated the transparency. In hindsight, I would have been much more communicative than I had been.

2. Cultivate a trusted adviser or mentor outside of the workplace. I think people should do this anyway but it helped me a great deal to have someone I could talk to about the issues I was facing and dispassionately help me evaluate the scenarios and available options.

3. Remember whom you work for and where your fiduciary duties lie. Yes, you ultimately work for yourself. But, as a founder or management team member, you may have fiduciary duties to shareholders, both common and preferred, to employees, creditors and customers. Their interests can diverge even in the best of times and especially so when things start going pear-shaped. I made some painful decisions that ruined a friendship but were for the ultimate good of the company and satisfied my fiduciary and ethical obligations — and, to reiterate No. 2 above, I’m glad I had a trusted adviser to help me make sense of things during such an emotionally fraught period.

4. Accelerate non-advertising revenue models. This is a more practical recommendation. Even if your usage and advertising metrics are growing nicely, now is the time to accelerate development of non ad-based models and prioritize the other revenue streams more highly. Your investors and potential investors and acquirers will appreciate this. Not only that but they are likely to discount your ad-based revenues anyway, so any momentum you can show outside of ads will bolster your story.

5. What doesn’t kill you will only make you stronger. Easy to say, hard to live through. But just keep telling yourself this when things really, really suck.

6. Pray! Seriously, luck plays a big role. Do whatever you can to make your own luck.