It's amazing how much music reveals about you. I've known this at least since my first angel investment, Last.fm
I wish Spotify made it easier to see other people's top lists.
Here's mine. The one thing it clearly shows is that I'm getting older...
There's an assumption of security in technology that has never been true.
More and more of how we live, work, and play is intermediated by online services. Every time you get in your car. Every time you buy a coffee. Every time you pick up your phone. Book a flight. Wire some money. Watch a movie.
From unauthorized access to social engineering, the core fabric of online services is not secure. And that won't change for the foreseeable future. If anything, breaches will be bigger, more impactful, more costly.
The fact that one of the largest hotel chains in the world didn't find out that its guest database was leaking passport and credit card numbers is mind-boggling in its implications.
And so I want to encourage you to take one annoying but necessary step to protect yourself: use a password manager.
Most people use a primary password, or some tiered level of "more secure" passwords that are nevertheless the same between services.
You only need one breach for it to become a real problem.
I personally use 1Password, but I've heard good things about LastPass and maybe Dashlane.
Do it today.
Kapil Gupta MD, coach to athletes, CEOs, and perhaps most notably (in our world) reviewed very favorably by Naval Ravikant, tweeted this in response to my previous post and comment "Not everything is political":
Doesn't that feel right? It does to me.
And reminds me reflexively, media-addled mind that I am an owner/a slave of, of this somewhat less beautiful Simpsons quote:
It is an addiction of mind, this obsession with news and politics and media. The ingestion, processing (labeling, judging), regurgitation of information, data, the attempt to accumulate, to hoard "knowledge", to better and lecture and prescribe. And the belief that through this same process we can relieve the symptoms of the pain...
The process is the pain in the first place.
We forget that we give permission to being disturbed by meaningless things. But once you're in the mind-world, it is much harder to stop. Just like an addiction.
I have days that I live without. Where I am with the world. Where I see, touch, smell, taste, am more.
Interestingly it is those days that my connection to others is strong. Where I am fully there and others - strangers, too - unfailingly notice.
On days like these I seem to be able to live more smoothly. There can be no wrong. Mind is my tool, rather than I a tool of it.
These are not fleeting times, a few minutes, here or there. It goes a while if I don't hit... a bump. It feels less like a different "state" than what the mystics write, and more "hyper-real."
Oddly it is not practice that makes it better. It's just awareness. There is no tension in it.
But then I wake up another day and it is gone, disturbed by... I am not sure what. A "bump." Some event, some anxiety, some future plan the outcome of which matters so much. And then we're back on the merry-go-round.
I think it is a form of self-sabotage. Surely I am overthinking this. :)
Venture capital used to be a highly opaque industry. Very few firms, accessible only through network, intransparent decision-making processes. From the outside it looked slightly mystical and certainly very glamorous (it is not).
Thankfully much has changed. The first generation of VC bloggers, like Fred Wilson, Brad Feld, Fred Destin, and others, have contributed to making the industry much more transparent and approachable. And so much capital has flowed in that you can't really move for new firms.*
Venture is now universally discussed - almost overly so. If you're in tech, it's hard to escape "VC Twitter", which is its own little ecosystem. Some of it is content marketing (a lot of it is content marketing), but there are so many smart, well-intentioned, insightful people that are very open that founders can now follow and reach out easily.
A similar openness has been coming to the Limited Partner ecosystem. LPs are the capital behind the venture funds, which are turn managed by General Partners, the VCs themselves.
Sapphire Ventures launched OpenLP in 2016 to foster more transparency in the tech (LP) community. The site aggregates blog posts and other writings by a very diverse set of LPs. It also has a Twitter hashtag #openlp that lets you follow the conversation.
I love the opportunity of learning more about the motivations and decision-making processes in a part of our industry that used to be similarly opaque.
If you're in venture, or an interested founder or investor, check out OpenLP. I've found it fascinating. Much props to Sapphire for running it.
* In numbers, the amount of capital available has certainly grown faster than the amount of good companies to invest in. Not dissimilarly, the amount of founders now outstrips the availability of good engineers.
We are all so distracted. You glance at the phone during our meeting.
When was the last time you gave something your full attention?
By that I don't mean focusing your mind. That just means pushing your distraction to the edges. It is still there. But now also there's tension.
It's hard to live while stealing glances to the side.
Step one might be to undo the labels.
Just to look, without naming the thing. To just be with the thing. To grok it.
Fred has a great post about track record today.
It got me thinking about my (much shorter) venture career and what some of my most valuable mistakes have been.
The top one is probably getting seduced by traction. Early metrics are good - we all like them. But they de-risk an investment less than commonly presumed. Particularly when customer acquisition is paid marketing and it skews the "true" data you could be getting.
I'd much rather see something grow organically in the beginning, even if that growth is slower than what's possible using paid.
Traction also shouldn't supplant other considerations, like what the market's true prospects are. It's easy to believe that because one company is making this new thing work for a small group of early and passionate customers, it has the potential to be a category-defining innovation. Sometimes novelty is just novelty.
Traction also shouldn't outweigh the team's overall potential. I've compromised on team a few times in my career. Particularly when there was a ton of traction and the idea was really big. Compromising on team has always turned out to be a mistake.
I love audacious people, but there's a fine line that separates it from slightly delusional. Where the vision supplants the details, I am much more careful than previously. A great founder can find the right balance between keeping the big vision and sweating the small stuff.
And finally on team, personality matters a lot. Low agreeability is a trait of a lot of successful founders, but low emotional stability is pretty harmful.
The other lesson is that a geo focus sucks. I invested very widely early in my career - hardware, B2B, marketplaces, travel, mobile apps, commerce... I believed that Europe as a geography had too little depth to really select on anything but people (see above).
I think that is still largely true for the market as a whole. But as an individual or even a firm, there's now enough capital that the huge benefits of thesis-driven specialization outweigh the missed opportunities.
That's why I've been 100% focused on consumer/user-only investing for the past year and a half, and I think that's what I'll want to do for the rest of my career.
I'm sure I've made many other mistakes in the last five years of active venture investing (and ten as an angel). But these are the ones that immediately come to mind as the biggest lessons learned.
I finished the final volume of the Broken Earth trilogy today, The Stone Sky. It is my favorite book of the three, not least because it feels more raw, complex, and has an incredible narrative crescendo culminating in one of the most dramatic fantasy scenes I have ever read.
I have to admit that I was skeptical initially - the three consecutive Hugo wins to the same author? But I am wrong. N.K. Jemisin is a fabulous storyteller and these are more than deserved.
While never overtly political, it is a story of allegory set in a world after climate change, touching on slavery, inequality, prejudice, revolution, redemption. The two female protagonists are mother and daughter, with all the complexities that entails. The plot is driven by a race to save the world and to uncover the mystery of the planet's ailments and its heritage of dead civilizations.
If you enjoy good fantasy/sci-fi and haven't heard of the books, they're worth your time. Or you can just wait for the TV show - TNT is making at least the first volume.