Sorry, you can’t. The decision to fund a company is a combination of a lot of human factors—an assessment of one group of humans by another group of humans, fraught with apples-to-oranges comparisons. Yet, everyone’s got an opinion about how a company measures up, especially the founder. (If you want mine, I’m doing a little consulting now.) So, how do you know what truth is? The other day, I had a difficult conversation with a founder who clearly felt like VCs were the problem in her fundraising process. The fundraising process sucks for about a million reasons—not the least of which is that ..read more

"Boy, do I have a lot to learn!" - Worst startup pitch, ever, right? Yet, that probably the closest thing to truth you could say in a pitch--and I'd argue that the kind of people you should be backing are the people who can admit this and who never stop learning. We don't do that a lot in the startup world. We reinforce the opposite--often out of necessity. We've all seen this happen... ? Founders leave the company before the exit, or move out of the CEO role. ? Investors move from one firm to another or start companies. ? Employees jump from one startup to another. In every one of those case ..read more

There are more active VCs alive today than have ever existed in the history of modern human existence—and that dates back 300,000 years! That means a lot of competition for the best deals and more difficulty in standing out. Add on the fact that some people theorize that the need for venture capital dollars will peak, or potentially already has, and then decline because of the ever-decreasing cost of technology infrastructure as well as the increasing capability of AI to replace expensive humans. If we ever do get to the one-person unicorn, that’s going to be a lot of people trying to beat ou ..read more

I’ve been coaching a lot of non-partner VC professionals and their number one challenge (besides taking obligatory meetings that their GP throws over the fence at the last minute—GPs, why do you do this? Stop wasting your team’s time and a founder’s time. Just pass when you think it’s a pass.) is trying to figure out how to get in front of the best founders with a title like Senior Associate or, potentially worse, Investor, which everyone assumes means Senior Associate. Don’t get me wrong. There are very smart, likable, and helpful people in these junior roles—but compared to a partner, if yo ..read more

Over a decade ago, when I was working for First Round Capital, we opened our doors for “Open Office Hours”—a series of open meetings where any founder could come in and chat with us for 20 minutes each. We met quite a few smart folks. I’m not sure we backed any of the founders—but that wasn’t the point. We made connections, hopefully made a good impression, and potentially helped founders along their journeys with some advice or connections. It’s an approach to the community that I’ve tried to emulate—to make myself available to founders wherever I can, but it’s not easy to scale. I couldn’t ..read more

Say what you will about VCs, but we’re a mostly predictable bunch. You know what our incentives are and we care enough about our reputation within the ecosystem to not do anything too terrible—usually. Still, there are a lot of downsides to taking venture money—the push to grow at all costs, our desire to be all up in your business, literally, and sometimes, we’re kind of obnoxious. That’s why when you come upon someone outside the traditional ecosystem, there might be a lot of compelling reasons to take their money. I’m not talking about active angels. I’m talking about what someone I know r ..read more

When people describe what they hate about networking, they often use the word “transactional” in a negative way. No one likes to sell or be sold anything—or to be only valued for your ability to exchange goods and services right there on the spot. That, however, is a very privileged perspective on time. People who can take the time to “get to know each other” without demanding anything right off the bat have both extra time and also enough stability in their lives to be able to forgo short term needs for long term benefit. You never hear a homeless person suggesting that you “see if there’s a ..read more

Two weeks ago, I opened X/Twitter and got pushed an ad for an anti-trans movie produced by PragerU and that was my final straw with this cesspool. I immediately requested my Twitter archive of over 63,000 tweets over 16 and a half years. Not surprisingly, it took nearly two weeks for me to receive a link to it given how understaffed the company is. Once I got it, I deleted my account. I’m gone from Twitter for as long as Elon Musk continues to own it. I’m sad about it—but actually more sad about what it has become more so than actually hitting delete. Twitter used to be a great community and ..read more

I find level setting to be one of the most difficult things to do around any task or skill. Just how good is good? What are the best people accomplishing? How do you measure it? It comes up a lot with my coaching clients who aspire to be top VCs and are trying to figure out how to self-assess and goal set. I figured the best way to go about answering would be to ask the best of the best. Over the last couple of weeks, I asked everyone who has been on the Forbes Midas List over the last three years what their activity and accomplishment actually looks like in the functional areas of the job. B ..read more

I’ve made over 100 investments in my career and nearly half of those went into diverse teams. I’ll be the first to back up the notion that diverse founders have just as much ambition, drive, intellectual horsepower, creativity—you name it—than anyone else. In fact, you could make the argument that, because of their lack of advantages in other areas, the ones who make it to a venture pitch actually have more of these raw ingredients because they’ve had to in order to make it to the same destination as their straight white male counterparts. There is, however, an advantage that some founders hav ..read more