Dancing with the Devil: A Founder’s Guide to Working with Legal

In my experience, most founders and other business folks think of Legal as a cost center related to risk management, a line item under G&A, an operating expense. I think that’s completely wrong-headed–regardless of the accounting rules. Done right, Legal can be a powerful ally in scaling your business, one that’s better conceptualized as COGS. […]

Uncomfortable Connection

We spend more of our lives with our co-workers than we do with our own family. I realized this uncomfortable truth long before I was a lawyer working 80-hour weeks. Even at a modest 40 hours a week it holds true for all practical purposes, and the reality of that lived experience takes its toll […]

Leaving the Unicorn

There’s a reason that people want to work for the proverbial Silicon Valley unicorn–and it’s not the shot at the equity prize. Oh, of course, that dream is present. We all gotta eat. But most professionals who have the chops to be hired by a fast-paced startup are smart enough to recognize that they’re not […]

Managing Equity Dilution from Convertible Notes

Raising startup capital by issuing convertible notes to early investors is a great way to get money in the door quickly. The great benefit is that most of the difficult negotiation gets kicked down the field a ways to the hoped for institutional round of venture financing. But can you really defer all those uncomfortable […]