This is squarely a very personal post, and I will try to keep it short and sweet. As a disclaimer, I do not intend this post to be read and/or interpreted as talking down to anyone or being disrespectful. Yet, I need to make this point clearly because I hear it a lot directed at me, and I think it leads others to drawing the wrong lessons and conclusions from my experience. With all that, here the few misconceptions I hear often lately:
1/ “Twitter must help you make investments.” NOPE. I have been using Twitter heavily now for over 12 years. It is how I navigate across the web. In the past decade, it has become an unofficial system of reputation and social record in the startup tech ecosystem. But, having an active and engaged Twitter presence has nearly zero impact on how investment opportunities come to me. Founders I want to work with do not care one bit about what happens on Twitter. Rather, the medium helps me share ideas, meet other folks (many friendships have been started on Twitter), and learn from others. Taking out the act of making investments, I do feel Twitter is critical for most startup investors, and participating in the network in a genuine way takes time, investment, and giving back as much as you take. A subject for another post, perhaps.
2/ “You used writing and content to enter the VC sector.” NOPE. While I was working in various startups, I would write because I was interested in a variety of topics. The act of writing helped me understand the new worlds around me. It just so happened that over time lots of LPs and VCs would subscribe to my work; then I would email with them; then I would meet them; then I consulted with a few; and then I thought one of them would surely hire me. That did not happen. Yet, I have people coming to me (or recommended to talk to me) about using writing as a wedge into VC. My response back is that one should write if there are interested in the craft, but thinking that writing a post or sending a tweet can be a strategy for getting into an investment career is simply not realistic.
3/ “You made great early investments, and you must know what you’re doing.” NOPE. In the first two Haystack funds, there was tremendous success, but there was no way to know at the time what the shape of these companies would be. Absolutely no way. What I did do, however, was focus on relationships and people. I built relationships on Twitter for many years. Then I forged them in real life. And then I tried to help tons of people, and tons of people helped me. I can’t think of another ecosystem in the world where super smart and experienced folks will meet you and guide you. I would have 30+ of these types of meetings a week for long time while I was struggling to find my way. But the only way to get really going is to get into the game with a small foot in the door, and then you have to get lucky and show enough value to get invited into the room to learn by osmosis. It can’t be engineered, in my opinion. It’s not fair that it isn’t open to everyone, but helping out others constantly is a good way to increase the amount of opportunities that may come your way.
In the last year, I’ve had lots of people knock on my door asking for advice about getting into venture. It is a humbling thing now to have someone knock on my door. And when they come inside, often I hear some or all of these misconceptions about the path to get there by looking back at what I did. But the story isn’t this way in reality. Twitter won’t help you get into VC or get better at making investments — neither will writing a blog post — and neither will being seen as an expert or company builder or operator or fill-in-the-blank. The only thing one can control is the goodwill they put into world, how they handle the people they meet, how they help others, and how to monitor the serendipity of the Bay Area ecosystem to notice the point at which it may tip in your favor.