Writing

What will the taxes be if I exercise my startup options?

This post walks step-by-step through a case study that estimates the tax impact of exercising startup stock options. I made this for myself, so I figured I’d share. It’s long and boring, but also possibly helpful. Lawyer warning: Before you do anything, talk to a professional! This is a high-level summary to give you an … Continue reading What will the taxes be if I exercise my startup options? →

Four Reasons Why Your Company Needs An “Always Be Learning” Program

At each of my last few startups, I instituted a program where employees teach each other stuff. It’s called Always Be Learning or #ABL (because everything needs a mysterious hashtag). At Kickstarter, it started informally with a few people on the operations team teaching each other topics ranging from SQL to egg cookery, and grew … Continue reading Four Reasons Why Your Company Needs An “Always Be Learning” Program →

How To Value Your Startup Stock Options— Discount Value

In the last several years at Kickstarter and advising startups, I’ve spent a lot of time trying to build models for awarding stock options in the fairest ways possible, talking to startups about the models they use, and thinking about the different ways to value companies and options. This post explains one simple way to … Continue reading How To Value Your Startup Stock Options— Discount Value →

From Lawyer to Deploy

I’ve learned a ton of great stuff in the last year and I’ve had a lot of fun learning all of it. Most of it is not easy to just throw onto a webpage, but some of it is exactly that. So, I’m working on a website to display a lot of what I’ve learned … Continue reading From Lawyer to Deploy →

The wrong question: “I want to learn to code, what should I do?”

If you want to learn to code and build stuff and you’re starting by asking someone else what you should do, you’re already thinking about it the wrong way. Immediately, right now, with no preparation, in the blink of an eye, you can take a huge step toward your goal by realizing that you don’t … Continue reading The wrong question: “I want to learn to code, what should I do?” →

Learn the Basics of Computer Science and Web Development

Two and a half years ago, I started doing every computer science and web development tutorial I could find. If I were starting again today, knowing what I now know, I’d do it something like this. Start with the basics of computer science and programming. Introduction to Computer Science I, David Malan, Harvard Extension School … Continue reading Learn the Basics of Computer Science and Web Development →

The common goal in compensation negotiations should be fairness

When negotiating compensation, the common goal most likely to lead to a successful, long-term employment relationship is fairness, not maximization by the employee or minimization by the employer. The compensation negotiation can set the tone for the relationship and is an early impression of company culture. Both sides want the relationship to be successful. Both … Continue reading The common goal in compensation negotiations should be fairness →

From Lawyer to Startups

My Poorly Executed But Successful Career Change How’d you get that job? That’s a question I’ve wanted to ask hundreds of people over the last twenty years. I would’ve loved to have heard their stories to help me make better decisions when managing my own career. In the last several years, for the first time, many … Continue reading From Lawyer to Startups →