So when the Stanford MBA, the ex­senior technology developer, or the former Chief Revenue Officer of a company is calling me and asking my advice on their next gig, you can see why I start with, "Are you ready to earn or to learn?" For most people it's learn. I only emphasize the question because I find it much more helpful to join a company with realistic expectations. My advice is often this: Make sure that what you get out of working at this company is one or several of the following: a great network of talented executives and VCs, more responsibility than your last job, specific industry or technical skills that will help you in what you do next, or a chance to partner with companies that will increase your industry relationships, etc. Learn now to earn later. When I was CEO of my first company (where I admittedly fucked up everything before I figured it all out), we initially calculated for people how much their options were eventually going to be worth. This was in 1999. A company called Ventro, with only $2 million in revenue, was trading at an $8 billion valuation. It was easy to do these calculations. Over time I realized that this created a rotten culture. Later, I took to telling people the following: "Join BuildOnline because you think you'll get great experience. Join because you like the mission of what we're doing. Join because if you do a good job we'll help you punch above your weight class and work in a more senior role. And if you ever feel in the year ahead of you that you won’t increase the value of your resume and you're not having fun, then go. Join because we pay well but not amazing. Stock options are the icing on the cake. They'll never make you rich. Don't join for the options." Obviously you should only take jobs that you enjoy and that let you be passionate about coming to work every day. That's a given. Don't blindly join a company without knowing why you'd join or asking the right questions. A friend recently called to ask for advice on becoming the CTO of a startup. He'd be employee number three. The company was being spun out of a larger company. I asked him how much of the company would be owned by the parent company and how much would be owned by management. He hadn't thought to ask. When we next spoke, he’d found out that the CEO had about 5% and there was no management option pool in place. My advice was ... Run! I said, "All the hard work is ahead. Why start the game with a company that has a structure that's likely to fail?" Another talented young man I recently met called to talk shop. He had an offer in NY, another with a well­known startup in the Bay area, and a third offer with a startup in LA. He also has his own company that he’d started six months earlier. He's not even 21. He wanted to know what to do. I told him that he needed to decide whether to learn or to earn. He's young enough to do either, but you need to know why you're doing it. I advised against the SF role because it was a bigger company and his role would be pushing paper from one side of his desk to the other. If you're going to learn, then at least go work somewhere exciting where you can really do