This really shocked me. Suddenly all of my friends had their hands out, expecting me to buy drinks and meals for them, all the time. They did nothing to help me with my business, and for the first few years, it was a lot of work and no money. Made me angry and I dropped most of them.

Now I’m vague with people about my work.

I’ve been looking for this comment. He’s in a C level role, yet says on at least two of these - suddenly out of cash, or cash flow issues. At that level he should have been fully aware and been either part of the success or failure. He takes credit for the success of a few, needs to take responsibility for the ones that didn’t. Typical to spin as if it’s not his fault.

Does the Office Manager handle payroll? Wonder if she sees what others are making and they’ve discussed and decided he should be making more?

Regardless, I’ve been in the position of having to limit increases because the money wasn’t there and understand you can’t just bump him up because he asked.

I’d discuss what you can do for him now, and perhaps what else he needs to do to get more in the future, but it’s reasonable for employees to expect an annual increase as well as a bonus.

Workday is overkill for 12 people. Less than 800 employees it’s too much.

There’s a number of smaller providers that should cost a fraction of what you’re paying for Workday.

We used OnPay. Very basic, simple, took less than 10 minutes to run the payroll. They also had a benefits broker and we were able to get a choice of plans through them.

I know many people that say they would never work for another startup. Expected to put in long hours in the hope it will pay off someday and in the majority of them, it never does.

Would you still take the job if the company folds in a few years and the equity is worth nothing? How much do you believe in the product and it’s ability to succeed?

If you set up the proper company, you can pay yourself below the limit and put any remaining proceeds into a tax deferred account. You need a good accountant to set all that up for you. Don’t try to do that by yourself.