Tag Archives: startups


How To Dig Out From A Career Failure

When I entered the venture capital business in 1982, Route 128 in Boston was as much a breeding ground for startups as Silicon Valley. That is no longer the case. I believe the Valley’s tolerance for failure allowed it to overtake Boston as the world’s technology center. In the Valley, you’re respected for taking a risk even when you fail. In Boston, like most everywhere else in the world, you’re thought to be stupid if you fail. Unfortunately many young people have misinterpreted the Valley’s tolerance for failure as a desire for it. I think of this when former students come by my home office to ask for advice after their startups have failed. First step on the ladder I […]

How Do I Choose Where To Work?

When it comes to deciding where you’re going to work, the quality of the company trumps everything else. After Wealthfront developed a Startup Compensation Tool allowing people to compare their salary and equity compensation packages against the market, our clients and readers asked us how they could identify a great company to work for. My students at the Stanford Graduate School of Business frequently ask me this question, too. The Patina of Success My answer is: You should most focus on success. You get more credit than you deserve for being part of a successful company, and less credit than you deserve for being part of an unsuccessful company. Success will help propel your career, whether you want to join the […]

Managing A Silicon Valley Windfall

Sudden money – such as comes with an IPO or an acquisition – is a good thing, right? Yes, but it’s often accompanied by stress. People who have been working within a constrained budget, steadily paying off college loans and sizable Silicon Valley mortgages, suddenly find themselves with a seemingly limitless number of options for spending their money. In this recent Quora post, Wealthfront Director of Research Jeff Rosenberger answered the question: “What advice would you give to someone who has the opportunity to cash in some of his private company stock in the low seven digits?” Jeff offered a three-step plan. Divest your stock “Unless you have an informational advantage that tells you your company stock is meaningfully under-valued […]

The 12 Crucial Questions About Stock Options

Next time someone offers you 100,000 options to join their company, don’t get too excited. Over my 30-year career in Silicon Valley, I’ve watched many employees fall into the trap of focusing on the number of options they were offered. (Quick definition: A stock option is the right, but not the obligation, to buy a share of the company stock at some point in the future at the exercise price.) In truth, the raw number is a way that companies play on employees’ naiveté. What really matters is the percentage of the company the options represent, and the rapidity with which they vest. When you receive an offer to join a company, ask these 12 questions to ascertain the attractiveness […]