The Truth About Convertible Debt at Startups and The Hidden Terms You Didn’t Understand

This article initially appeared on TechCrunch — with a minor update highlighted in red below.

How to Develop Your Fundraising Strategy

Raising money is hard. And when you’re relatively new to the process it’s easy to be confused by the process. There is all sorts of advice on the Internet about how to raise capital. Of course much of it is conflicting.

Entrepreneurshit. The Blog Post on What It’s Really Like.

It’s 4.50am. Sunday morning. And I couldn’t sleep. I have much on my mind since I just returned from a week on the road. 5 days. 3 cities.

Some Quick Sage Advice for Young Employees Early in Their Careers

My wife & I have a close friend who recently entered the workforce for his first-ever job. On his first day of work my wife was kind enough to write down words of wisdom from her years on the job.

Trello versus Asana

For the past several years I’ve undertaken many initiatives to “get more organized,” which basically means to make another attempt at implementing and running a solid task list that I can share with others with whom I collaborate.

Should Investors in the Same Round of Financing Ever Get Different Prices?

If you were on Twitter on Saturday you might have noticed a lively discussion with Dave McClure, Fred Wilson, Chris Dixon and myself. And a few others.

Why Startup Entrepreneurs Need to Communicate More Like George Bush Than Al Gore

This article originally appeared on TechCrunch.

It is election season.

What to do About that Chip on Your Shoulder?

I’m fond of saying that I look for entrepreneurs that have a chip on their shoulder. That they have something to prove. That they’re not afraid to stick their noses up to the establishment.

Rethinking Board Observers — The Role of the “Silent Observer”

It has always surprised me that founders were so quick to fight over how many board members there were and so quick to agree to have as many board observers as people wanted.

Why You Should Think Twice Before You Send That Intro Email

Intros. They’re the lifeblood of networking — the currency of mavens. They are your route to angel money. Your entrée to sales meetings.