"Look, if I drink any more Espresso, my head will explode!"

I am back at Peet's Coffee discussing job search strategies with Ying and Yang, the nicknames I have given to my two former summer interns. They are out in the real world now, and have decided to split from their current jobs at big, boring companies. Both are interviewing at Internet startups in Silicon Valley. For some strange reason, they are meeting me again for additional job search advice.

"So why do you guys drink this? It tastes like motor oil!"

Yang fires back, "How would you know, Joe? That cheap gin you drink killed your taste buds years ago." Actually, it wasn't gin, but I didn't want to talk about my years of going to Grateful Dead concerts.

Ying chimes in, "So Joe, we both have gone pretty far down the interview road at these startups. No illusions - will be 70 hour weeks for a while. We took your advice about stock options, and we are negotiating some protection if they get taken out. We want to get some of our stock vested!"

"Good move!" I shout. I bet no one else at those companies has thought of what happens to their stock options if the company gets bought out. They could be in for a rude shock.

"So, who are you interviewing with?" I ask in my leading question' voice.

"The engineering managers, who else?" replies Yang. "Sounds like a lead in to another Wisdom of Joe' lecture." v "No, just curious...but how can you tell if these companies are going to make it by talking just to the engineering managers?" I ask.

"So far they have only had us interview the engineering guys, so what's the big deal?" snaps Yang.

I start in on another monologue that even John Galt would be proud of. "You are going to be working your butts off for the next two years. Make it count. If the job looks good, talk to several other departments, especially in marketing and sales channels."

"Why?" Yang asks. "What do I ask a marketing guy? Why would he or she want to interview me?

"Look, marketing is simple in theory, extremely tough in practice; sort of like using Java in the real world. If the marketing and sales guys know what they are doing, then all your 70 hour weeks will give you a shot at that big win'. If they are clowns, then the tightest code you can write will be for nothing. Look what happened to Apple toward the end - the inability to market their products against WinTel negated the efforts of a lot of good engineers. So ask a couple of questions about marketing strategies. Lots of marketing guys in Internet startups came from big computer companies where they really didn't do anything except show up in a suit and regurgitate the company line."

"So how did those guys end up at the hot startups?" asks Yang, who has come down from his espresso high long enough to look worried.

"They had good resumes and references that made them sound great. The fact that the references themselves were not that great was never checked out. Look, I can ask you in an interview to hack up some Java code and know in a few minutes if you are good. Marketing guys can scam their way for quite a while, sometimes for a whole career. So, how do you know if a marketing guy knows what he is talking about? Meet the Director of Marketing or the senior product guy associated with your product. Ask him some basic stuff. Who is the competition now and who do they think it will be in two years? Why is his product better than the other guy's? What keeps him awake at night worrying? And, the most important question, the elevator speech. If he had only 30 seconds, like in an elevator, explain what his product is, what it does and why it is better than the competition. Any marketing guy that will make a startup happen has already developed an elevator speech. They need it when they have a chance encounter with a potential customer, investor or reporter. If the marketing guy doesn't answer those questions in a way that you are comfortable with, then there are problems ahead."

"So," says Ying, "You are asking us to interview them as hard as they interview us."

"You know, most young programmers in Silicon Valley know more about the San Francisco 49ers that they watch for 3 hours a week, than they know about the startup they will be putting in 12 hours a day for. And one last tip, meet the president of the company. Ask him or her about what they see the company doing. Is it an IPO candidate or will it be taken out by Microsoft or Cisco? Ask the toughest questions you can think of, like what was their worst business failure and what did they learn from it? If they can't handle an engineer asking those questions, then there are bigger problems. Move on."

"So Joe, you seem like a smart guy, but you aren't at a startup that will make you rich!" fires Yang in his normal sarcastic tone.

"Well, that reminds me of THE most important factor in hitting the Big One at a startup: blind luck. Even with the best team, it's a roll of the dice."

"Great," says Ying. "Maybe I should just stay at this boring company I'm at and do the 9 to 5 thing."

"You won't," I reply. "The brass ring is out there, go for it. And if the dice roll your way, at least give me a ride in the Ferrari!"