I haven’t been writing much here, of late. Lately, I’ve been traveling, much more than I prefer to. Some of it was for work, some of it was an annual trip I take with old friends. Most recently, it was a much-needed family trip. As the first days of that trip sunk in, it dawned on me — I hadn’t had a trip, a planned vacation, for this duration, without having any work I needed to do, for at least five (5) years — if not more. Now, that’s mostly because of my own doing and not being great with setting those boundaries in the past.
This time, I needed it. Of course, I did some work, work reading, and light emailing and phone while I was away, but I really love investing, so it doesn’t feel like work, especially when good people are involved. But, for what seemed like months leading up to this trip, I felt overrun, over-scheduled, over-programmed, over-emailed, over-meeting’d, over-talked, and over-committed to speaking events. By the tail end of it, I realized — again — it was all of my own doing, not creating the time and space to step back, to pause, to reflect, and to ask: “Why am I being invited to speak at 2-3 events per week? WTF is going on?”
What’s going on is that there are more and more “tech events” accelerating in quantity. It’s not a bad thing, but it’s easy to get caught up in all of it. Dinners, fireside chats, community meet-ups. For the last 18 months, I’ve been consciously trying to do more of this, partly because I like speaking publicly, and partly I wanted to see what it was like. I think I’ve had my fill for now. In today’s environment, it’s hard to take the nuanced position of being long-term bullish on technology but also simultaneously puzzled by the price of assets (in this case, equity) today.
I’m excited for the summer because I have very clear objectives. Not much travel. I am nearing the tail end of Haystack Fund #2, which invested at a more aggressive pace than Haystack #1, but I need to wind that down a bit and take time to reflect on what I’ve learned, the mistakes I’ve made, and to read about the rest of the world to see where my mind wonders. Before May, while I gained a quicker draw at decision-making and filtering investment opportunities, I noticed my point of view as to how parts of the world would be shaped started to dull. I just reacted to what was presented to me. Additionally, during this time, deal flow referrals and emails seemed to spike without warning. I couldn’t keep up. For a while, I lamented that any “picking abilities” I once may have had felt out of grasp, lost in the noise of emails, texts, and tweets about new companies, new rounds closing. Everything had a ticking time clock attached to it, so the easiest response was to investigate what I knew instead of broadening my scope of knowledge.
Over the past 18 months, if you subscribe to this blog, you may have also noticed that when I did write, I wrote more about the mechanics of raising venture capital, how LPs work, why VCs make various decisions that seem odd, etc. That’s because in VC there’s investing, what we all envision it to be, and there’s also a business of VC, which I had to learn. Like you, I’ve had 100s of LPs (investors in funds) tell me “no” or “come back when you have a bigger fund.” While a VC may often understand the business model of a startup business he/she is evaluating, very rarely do entrepreneurs understand the business model of VC as an industry (and how it’s changing), and I believe that disconnect fuels at least half of the misunderstandings between both sides. So, in a small way, I try to explain what I’m going through in the hopes that it helps the next founder understand where I’m coming from — and in turn, the process reinforces to me where that founder may be coming from.
All of this rambling is a long-winded way of saying “i’m back” to write more this summer, to reflect more, to subscribe to the mantra “less meetings, more tweeting,” or at least more writing. A seed round is closing in a few days? Cool. You’d love to meet up live in the next week. Sound great. Except, it likely won’t happen this summer, because if I don’t stop a bit to write down the learnings and mistakes, I’ll keep making them.
I kept a notebook of all the things I wanted to write about, and now I’ve replenished my creative reserves for the summer to do just that. As a teaser, I have one page in the notebook with the headline “Things You Don’t Want To Hear.” I’m lucky to have this outlet, free of editorial control, to voice my points of view, and to work with colleagues who encourage me to do so vs being concerned about “staying on message.” I also won’t fall into the content-marketing zone — I won’t add pictures to my tweets, use canny titles, or schedule them for you to read them at optimal times, or opine on the latest topic du jour. Most of the writing is for me. If you happen to read it, I hope you like it — and I hope you have a great summer.