Travelogue: Riyadh

I recently traveled to Riyadh, Saudi Arabia, to speak at the RiseUp Summit Saudi.  I had spoken at the RiseUp Summit in 2019 in Cairo, so when the organizers asked me if I would be willing to travel to Riyadh for their first event in Saudi Arabia, I checked the calendar, saw that it wouldn’t … Continue reading Travelogue: Riyadh

Always Search For The Mechanism Of Action

I’m a weirdo. I don’t mind admitting my eccentricity, because I believe that some of my unusual habits help me in life. One of these habits is my obsession with figuring out the mechanism of action. I don’t remember the details of when I first learned the term, though I believe it was in the … Continue reading Always Search For The Mechanism Of Action

Choosing a VC based on valuation is like hiring the cheapest job candidate

We’re in a buyer’s market for capital these days, which means that every day I read headlines about how Startup X raised Y million at a Z billion-dollar valuation from Funds A, B, and Tiger Global. It’s very easy for first-time entrepreneurs to read these headlines and think that the most important number is Z, … Continue reading Choosing a VC based on valuation is like hiring the cheapest job candidate

The Ultimate Startup Success Plan (based on 10 years of data)

First Round Capital, the first and foremost of the “micro” VC funds, recently released a retrospective set of lessons learned based on 10 years of investing data.  It’s an incredible trove of data, some of which I love, some of which makes me feel uneasy.  But since I always believe in working with the world … Continue reading The Ultimate Startup Success Plan (based on 10 years of data)

The Only 4 Reasons Investors Say “Yes”

Alex Schiff is a great guy and the creator of one of my favorite products, Fetchnotes.  I met him when he was raising money for Fetchnotes (in the end, I decided not to invest because while I loved the simplicity of the product, I concluded that there weren’t enough self-organizing people like me to represent … Continue reading The Only 4 Reasons Investors Say “Yes”

The Value of Investors: Why I Focus On Helping Entrepreneurs

From Peter Thiel’s recent Reddit AMA: “As an investor, I think one must always maintain a certain amount of humility. There is only so much we can do to help the companies in which we invest. And because of this, the act of making the investment (rather than the ability to fix things later) remains … Continue reading The Value of Investors: Why I Focus On Helping Entrepreneurs

What’s It Like To Judge A Pitch Competition

I enjoyed reading a recent Fortune article that provided a behind-the-scenes glimpse of the judges at a Rice University startup competition.  It didn’t hurt that my old friend Robert Winter was prominently mentioned! http://bit.ly/UffMcc However, I think it’s hard for a reporter to truly understand the dynamics of a judging team.  I’ve been a competition … Continue reading What’s It Like To Judge A Pitch Competition

When you raise a lot of money, you raise the degree of difficulty

Investors are fond of telling entrepreneurs about how dangerous it is to raise too much money too early on.  We advise entrepreneurs to minimize fundraising until they achieve product-market fit, and are ready for scaling up. The problem is, entrepreneurs don’t want to hear it.  It’s like telling Americans to lose weight by eating less … Continue reading When you raise a lot of money, you raise the degree of difficulty

The Power of Surprise

Humans love to be surprised (as long as the surprise isn’t a nasty shock). As thinking creatures, our ability to develop an accurate working model of the world depends on our ability to spot the unexpected. Surprise is a great mechanism for rewarding that ability. Wharton conducted a study of viral videos.  They had research … Continue reading The Power of Surprise

Why You Should Focus On Building Your Reputation

After writing about the importance of reputational capital, I realized that in many cases, it’s more important to focus on building your reputation. The key insight is this: As an entrepreneur, your control over the financial outcome of your startup is limited.  Luck is a necessary but insufficient factor in nearly every startup success. On … Continue reading Why You Should Focus On Building Your Reputation