
Why Only 12% of VCs Can Be Considered Successful. Max.
Continuing our recent series on The Catharsis is Understanding How VC Really Works, it was only recently, spurred by Quora, I really thought through just how many VC partners can really be considered a success. Turns out math says it can’t be that many. No matter how it may look from the outside. . Why? Well… […]

What is it Like to Negotiate a VC Round?
Over the years I’ve written extensively about the downsides of convertible notes for startups such as here, here and here. The truth is that I’ve been warning about convertible notes since 2010 it was first declared that “convertible notes have won.” Today I want to talk about how a VC thinks about equity pricing on your […]

An Insider’s Guide to Convertible Debt vs. Equity
In the annals of Blog Posts About Things I Don’t Care About, Convertible Debt versus Equity is high on the Top 10 List. It’s not higher than How to Have a Great Bored [sic] Meeting, but it’s high up there. I mean, whatever, right? All that matters is investing in great companies at a fair, […]

One Simple Paragraph Every Entrepreneur Should Add to Their Convertible Notes
I’m so tired of seeing young entrepreneurs get screwed by their angel investors on convertible notes and I know I can’t convince you not to do it so I’d like to offer one simple bit of advice to help you avoid getting screwed (at least on one part of your note). When you do a […]

Some Career Advice for Aspiring Tech CEOs
You’ve never been a CEO but might like to be one some day. But how? Nobody sees you as a CEO since you’ve never been one? I wrote this conundrum and the need to take charge of how the market define your skills in my much-read blog post on “personal branding.” If you don’t create the […]

Be Careful About Being a Meddling Startup CEO
I recently wrote a post talking about how some VCs meddle in operating company decisions or some executive teams are too reliant on VCs to jump in and make hard calls for them. Fred Wilson also wrote on a similar topic in his usual more succinct manner, with a great quote being: “One thing I […]

Why Most Online Video Companies Will Fail
I live in LA and fund startups. So you can imagine that I see a lot of video startups. Most will fail. I repeat the same mantra to every one I see. “You can’t build a large online video company. You have to build a large online tech company that distributes video.” I try to […]

Here’s What The @NYTimes Should Teach Its Writers About Social Media
Not everybody likes the NY Times. I happen to be a long-time fan and paid subscriber. I mostly read the op eds and have for years. I count amongst my favorite people to read from the left & the right as David Brooks, Thomas Friedman & Paul Krugman (and was a big fan of the late […]

One Weird Trick to Build a Personal Brand
My long-time friend Jason Lemkin is on the verge of launching a spectacular SaaS conference called SaaStr this week. What Jason has achieved in no time flat in VC is astounding. Without inventing the browser he has single-handedly created a personal VC brand on a shoestring. And as I’ve written about before – building a […]

How to Build Online Relationships into Meaningful Networks
I was waiting for my son’s basketball game to start this morning and with the morning’s emails all drained I turned to Twitter and saw this Tweet from Marshall Kirkpatick Test: open your twitter stream, look at the 1st item in it, think of something to say in response, say it. Theory: it’s really that […]

The Most Misunderstood Facts About Building a Business on YouTube
Any reader of this blog for a period of time will know that I’ve been long YouTube for years. Along with Greycroft, I was the first institutional investor in Maker Studios (sold to Disney for nearly $1 billion) and am still the largest investor in Mitu Network, the largest online video producer of Latino content. […]

Blogging for the Hell of It, Not Blogging to Stay Relevant
I used to love blogging. For me it was always a creative outlet. I love sitting down – often in “one take*” like a classic film – and capturing what was on my mind at the moment. What I loved about it was that my thoughts were instantly in the ether, I would get quick […]

The Silent Benefits of PR
I’ve been having this PR discussion with three separate portfolio companies at once so I thought I’d just publish my thoughts more broadly. I have written many times about PR so if you want a deep dive on the “how” of PR you may enjoy reading some of these posts. PR is an insanely valuable […]

The Silent Killer – The Company Your Community Never Created
I was at a dinner recently in Chicago and the table discussion was about building great companies outside of Silicon Valley. Of course this can be done and of course I am a big proponent of the rise of startup centers across the country as the Internet has moved from the “infrastructure phase” to the “application […]

The Audacious Plan to Make Electricity as Easy as WiFi
When I first met Meredith Perry she was 24. That was three months ago this week. Today I’m handing her the largest A-round check I’ve ever written as a VC as we lead her $10 million A-Round at uBeam. As I’ve written about recently, at Upfront Ventures we started talking a couple of years ago about […]