“How much should I ask for?” Almost every single time I talk to a founder as they’re prepping their raise, this comes up—and it’s absolutely the wrong way to think about a round. The right question is, “How much do you need?” When you raise money, the way you should …...Read More

A recurring theme in a lot of my BSList posts is that, if an investor thinks they can make a boatload of money with you, they’ll go to all sorts of lengths to invest. That includes investing way earlier than they would normally, investing outside of scope, investing with their …...Read More

Everyone starts their fundraising the same way: 1) Open a shared Google Sheet. 2) List all the VCs you've ever heard of. 3) Ask a bunch of people who they know. 4) Find out very quickly this isn't very effective. First off, most people in the world can't name any …...Read More

Being a VC means not only honing your skills as a judge of character, assessor of business models, and calculator of risk, but it’s also a lot of difficult interpersonal communications, narrative creation, and long-term goal setting and positioning. While some of the hard skills and prerequisites to do the …...Read More

Almost 20 years ago, sometime after Fred Wilson started writing and just before Brad Feld jumped in, I started “blogging”. I put that in quotes because no one really calls it blogging anymore and there aren’t even that many people still doing it from those days. A few went pro …...Read More

All of our planning starts with the following two premises: 1) We’re not in the business of events, and so if we’re going to do something, it shouldn’t suck, because then we’re wasting everyone’s time, including our own. 2) Most startup events suck. Why? It’s overly simplistic to say that …...Read More

Last August, I passed the point at which I had spent literally half my entire life working in this asset class, having started at the General Motors pension fund doing institutional investments in venture funds and late-stage directs back in February of 2001. No matter how you slice it and …...Read More

It’s been a couple years since my last post here, and once again it’s December and I’ve been doing a fair bit of reflecting. I love this blog. I love writing. But I’ve decided to try something new. I’ve launched a newsletter called Focused Chaos. I’ll be writing there about …...Read More

Almost three years ago I wrote a blog post titled Hello, 2017. That was the last blog post I wrote. Since then I’ve been completely heads down building Highline Beta. It’s been quite the journey. Building a startup is basically an all-consuming experience, physically and mentally. The ups and downs …...Read More

2016 was one heck of a year. It started with a fairly big shakeup professionally. I didn’t end up taking much time off; instead I started meeting with lots of people and looking for my next adventure. In July, 2016 I announced the launch of my new startup, Highline BETA. …...Read More