Moving Weaknesses into the Strengths Column

A few months ago, I started working with a coach, which is something I probably should have done a long time ago. We recommend it broadly for CEOs/leaders in our portfolio for a reason.

Last week, we were talking about my strengths and weaknesses, and Alisa suggested something simple, yet profound, which was: looking for ways to move things that I know to be weaknesses into the strengths column, by changing how I approach them.

In my case, I tend to be stronger at collaborative work, and somewhat weaker at solo work (this is a generalization but a decent enough one for these purposes). Said differently: I really give and gain a lot of energy when working collaboratively / live on things with others, and have a harder time prioritizing and motivating on things totally on my own.

So, one way to handle that knowledge is to work on ways to improve directly on those solo things -- for example, by blocking time on the calendar more effectively, making better use of AI tools to speed certain tasks up, etc. It's obvious to begin by focusing in this direction, which you could bucket as the "strengthen the weakness" approach.

A perhaps less obvious approach would be to "move the weakness to a strength".

For example: every quarter at USV we update our internal valuations of all of our holdings, and each partner does this independently for the investments they manage. For no good reason, I tend to fall behind on this and do it at the last minute, and it's annoying for everyone.

Today, I got on with one of our fantastic finance team members, and together we went through my list. This had a multi-part benefit: 1/ it got done, and quickly; 2/ by doing it together, we actually investigated a flagged a few things that required follow-up from others on our team and 3/ it was fun.

So, what we have decided to do going forward is: rather than the finance team bugging me to remember to do these myself each quarter, we're just going to pre-book a 30 minute call to do it together, which will be a much better approach for all the reasons I mentioned above.

In this particular case, I feel so so lucky to have the benefit of an amazing team at USV, where I can really leverage this particular strength area (not just my own, but ours as a team).

But regardless of the particulars of any person's strengths and weaknesses, I'm intrigued by this idea that in addition to just focusing on improving our weaknesses, we can also look for opportunities to replace a weakness with a strength, and that may end up being the more realistic / effective path.


Verified Personal Content

For the last 15 or so years, I've been blogging occasionally on this website. Unfortunately, towards the end of last year, I lost control of my long-term domain name, nickgrossman-dot-is (intentionally not linking to it here). This was a dumb mistake; I just missed the renewal notice and someone else claimed it. Painful lesson learned.

At the time, I was bummed but figured it would just be on me to rebuild SEO to the **real** Nick Grossman blog. But, oddly, the new registrant has taken the extra step of republishing fake versions of my old content on the site, presumably in an attempt to retain SEO the old posts. Notably, all of the content has been slightly modified -- just enough, I guess, to sidestep any takedown claims based on copyright infringement.

So, what started out as an annoying and unfortunate situation has taken a turn to something more ugly: at best, an attempt to farm some referral links; in the middle, a shakedown effort; and at worst, an attempt at some kind of slow-motion identity theft.

All of this has gotten me thinking about ways in which the new decentralized media stack can help address some of these problems.

If we look at a platform like Mirror, which is a new publishing platform built on crypto rails, there are two main components: 1) Ethereum for identity and economics, and 2) Arweave for permanent data storage. Much of the attention thus far has been focused on the first prong: economics. Mirror's Ethereum bones mean that potentially unlimited forms of economics can be built into publications. For example: Emily Segal crowdfunded a Novel; Matthew Chaim is experimenting with publishing an album and a number of associated NFTs; and Jarod Dicker is experimenting with channeling economic flows through to authors and inspirations who contributed to new content. Mirror is becoming an incredible playground for the economics of content.

While the focus on economics is really exciting, there has been less focus on the implications of the identity and perma-storage aspects of the stack. Identities on Mirror are Ethereum wallets, and all of the content is archived -- in a verified and permanent way -- in the arweave network.

What that means is that, for every post, there is a blockchain-verified, permanent, immutable, record of who published what, when. Data stored in arweave cannot be changed; it can only be referenced. Every post in Mirror creates a permanent, reference-able, linkage between the identity of the author, the time of publication, and the content of the post. You'll notice that every post has a footer that looks like this:

For my use case of a hijacked domain name and republished fake content: if I had published my original blog on Mirror/arweave, there'd be a permanent record of the real/original content. For that to matter, though, "the internet" would need to learn to trust & reference the archival version of content, not modified copies.

Of course, a version of this exists today with the Internet Archive, which is an invaluable resource (and presumably, the way the new owner of my domain scraped all the old content....). While the Internet Archive is an incredible resource, it has not yet become deeply linked with other forms of publishing and identity on the web. In the case of Mirror, given the native linking between on-chain identity and content, a vibrant ecosystem is much more likely to develop around this kind of verified content.

More broadly, verified content feels like an important primitive in re-establishing trust online. Deepfakes, identity theft, social media bots, etc -- these are all affronts to our sense of reality online, and our ability to trust platforms and people. Just as the economic aspects of Mirror have been at the forefront so far, they have also been for crypto broadly.

While it's true that crypto networks introduce new forms of economics (speculation, payments, crowdfunding, etc) -- the underlying feature that enables them is trust in data. Crypto assets have value because we trust the data systems that generate them. I am excited that we are now starting to explore applying these same concepts to a broader set of online assets -- critically important ones: identity and content.

(note: this post has been cross-posted to Mirror here)


Getting Right for What's to Come

Fred and Albert just posted their annual posts on predictions and issues to tackle for the coming decade. Both are great, and thinking about all that we will need to do to in the coming decade is both inspiring and intimidating.

Before I can even think about those kinds of things and how to approach them, I need to look on the personal side and check in to make sure that I have as strong a foundation as possible, like putting on your own oxygen mask before helping others:

Everyone has their own challenges and issues to work on, so here I will just note some resources that have been helpful to me, in no particular order:

  1. Getting professional help. I have written before that one of the breakthrough moments for me was when I realized I could seek and get help where I needed it. In my case, it was a great therapist and a great accountant. But the big idea is that it's ok to get help. You deserve it.

  2. Dry January. For the past few years I have quit alcohol for the month of January and it always feels great. The holidays can be a bit much, and a lot of us consume more than we should anyway. Dry January is, at the very least, a good opportunity to explore the role of alcohol (or lack of it) in your life.

  3. This NYT piece on procrastination is great. I have always struggled with this, and I completely agree with the main idea here which is that procrastination is an emotional issue (avoiding unpleasant feelings, self doubt, etc) not a discipline or self control issue.

  4. James Clear and Atomic Habits. I've only skimmed James' book Atomic Habits, but he's great on twitter and seems spot-on to me with his analysis of how to create positive habits.

  5. Work Clean by Dan Charnas. In this book, Dan studies how great chefs manage their workspaces and apply those lessons to other forms of work.

  6. Alex Iskold's Self-care: 8 Tips for Founders to take care of themselves - great lessons here and Alex talks about this stuff from a place of real personal honesty and empathy.

  7. The Volt Planner by Kate Matsudaira. For the past 4 years I have used the Volt Planner, which guides you though yearly, monthly and weekly goal setting. I have found it to be supremely helpful in a world where there are a lot of things competing for your attention and it can be hard to focus.

  8. Brad Feld's mantra to Simply Begin Again - simple and really helpful.

Whatever issue you are tackling, I hope you can find the resources to help.

As I look out at the new year and the coming decade, I want to have all the energy and leverage I can to make good things happen, and that starts at home with building a strong foundation, whatever that means to you. A little better every day.


Saying Sorry

As I turned to write this, I was in the middle of reviewing a document a friend had asked me to look at a little while ago. In somewhat typical fashion, I had not done it right away, and had basically forgotten about it until he pinged me again, and even then I didn't get to it right away.  

I feel terrible about that, and as I reflect on things as part of Yom Kippur today, I realize that one of the things I feel the worst about over the past year is being a bad communicator. I have let things drop and haven't been responsive.  At the end of the day, it's a matter of respect and I have not done a good enough job.

So for the many of you out there (including readers of this blog -- notice no new posts for about 5 months...) who I've done this to, I am sorry. I will do better.


Setting up a system

Like most people, I have struggled over the years to comes up with a organizational/productivity system that works for me.  Disclaimer: I do not yet have it down perfectly, and am not claiming guru status.  But I do have a few things that have worked pretty well, and I have noticed some things that others do that seem to work, so I will share those here.

I have a somewhat elaborate system which I will explain below, but at the end of the day it all boils down to a single strategy: getting things into my calendar.  The other main thing I try to solve for is simply not forgetting things.  I live in a constant stream of emails and meetings, and it's easy to forget something important.  So a goal here is to help ensure that I don't forget things and ultimately, that I'm focused on the most important thing most of the time.

I live by the calendar and generally obey it.  This is a trick I learned from Fred, who doesn't use any productivity system except for brute force email and calendaring everything.  Getting something into my calendar is the most sure-fire way that it will get done -- having a date and time attached to something gives it a lot more weight than a wishy-washy entry on a list of to-dos or "priorities".

Working backwards from the calendar as ultimate do-place, I have a few tricks for capturing and prioritizing, loosely based on the "Getting Things Done" theory of capture/clarify/organize/etc.   As much as possible, I try to get big things out of my Inbox and into a place where I can see and organize.  For this I use Trello.  I have a board I use every day that looks like this:

From right to left:

The main show here is the "priorities" list, where I try to pluck out the important big things on my plate -- this helps me make sure I am not forgetting something.  Roughly daily, I review this list, sort it, and make sure things are in my calendar to do.

Another list in my Trello is "meetings".  I use this list to capture high-level takeaways from meetings.  I am a big believer in the concept of the "commonplace book" and the value of taking notes and reviewing them over time.  For me this step is more about just general processing rather than to-dos, though there is a to-do component.  I take meeting notes by hand in a small notebook (currently a moleskine but in the old days I used a spiral bound), and always mark follow-ups with a "F/U" with a circle around it -- this is a trick I learned from Phil Myrick back when I worked at PPS.  As a way of processing the meeting notes, I make a card in trello for each meeting and add the follow-ups as checklist items (Dani has a system similar to this, using Notion, and I'm always impressed with how well it seems to help her process meetings).  For little things, I just do them right away, for bigger ones, I prioritize and calendar them.

On the left is the "Inbound" list.  I use this to capture fleeting thoughts, ideas and notes.  Things get on this list in two ways: 1) via Wunderlist, which I mainly use by phone -- I have found this to be the easiest and quickest way for me to jot something down on the go.  I use Zapier to move things from my main list in Wunderlist into "inbound" on Trello.  2) I use Trello's built-in email-to-board feature to get larger items out of my inbox and into Trello.   Again, the goal here is just to capture so I can process/prioritize later.

Another input into this system is my other notebook, the Ink+Volt Planner. I am on my third year of using this wonderful tool: it's a structured goal and priorities setting notebook that helps you create and reach yearly, monthly and weekly goals.   I find that the Ink+Volt, like meditation, helps me cut through the noise and see what's important more clearly.  I do a planner session every week (it's in the calendar), and use that to inform all of the above.

Having now written all of this, it seems pretty clear that this is a lot of work, and may be excessively complex.  My wife would probably describe this as "planning to plan", and just an elaborate mechanism for avoiding doing the actual stuff, or something like that.   That may indeed be so, and I often think about Fred's simple strategy of blast relentlessly through email and calendar everything.  It is impressive and seems to work.  Mostly, I use this system so that I am not just at the whims of my inbox.

For sure, my biggest weakness is email, which I still struggle with.  Albert has a system here, which seems to work for him, which is: using a set of predefined gmail filters, clear the inbox daily.  Not the entire inbox, but a few filtered versions (family, USV team, his portfolio companies).  I'm not there yet.

So, there you have it.  That's my system. It's a work in progress.  What's yours?


Getting the chills

One of the greatest things Frannie and I have in common is that we get the chills from music -- typically at the exact same time, triggered by the same musical... something.

For me it starts  at the back of my neck, and if it's really good, it spreads all over my back, head, and chest -- if it's really really good I end up with tears in my eyes.  I get it the most from vocal solos and tight harmonies, in particular R&B, gospel, and certain musicals. 

It'll happen and the two of us will look at each other and be like, wow.   

Apparently this is not just a random thing, but there is actually a lot of science to it.  I never really looked into it until today, but it even has a name: Frission, or more colloquially, a "skin orgasm".  Here is a good overview of the phenomenon, and here is a ton of assembled academic research on it.  There is even a subreddit devoted to it.

I experienced it this morning on my train ride into NYC, and of course immediately thought to blog about it and include a clip that attempted to communicate it.   As I read more about, a few things stood out: first, not everyone experiences it -- estimates vary but somewhere around half of people feel some sort of frission response that can include chills, welling throat, tears, etc.  Second, the experience is not just about music but also about meaning -- often times particularly sad passages cause the experience (eliciting a deep-seated survival instinct), so it often requires at least some conscious or sub-conscious attention to lyrics. And third: musical context matters -- it is often the result of a musical build-up over the course of a song, and an isolated passage on its own might not have the same effect.

Given all that as setup, here is the one that got me today.  The closing number from The Greatest Showman (which happens to be my daughter's favorite album right now, so is playing constantly in our house).  The part from 3:18 to the end is the kicker, but it's probably best to start from the beginning to get the whole build.

Best with good headphones, loud.  Curious to know if others get it too.  Enjoy!


Finding your discomfort zone

I have been down in DC the last few weeks, among other things, talking to lawmakers and regulators about cryptonetworks and cryptocurrencies.  As part of that, I've been spending a lot of time with attorneys -- specifically securities attorneys -- getting into depth on issues like the definition of an "investment contract" and case law like Howey, Reves and Forman. Separately, I've spent a bunch of time over the past 9 months helping USV portfolio companies getting ready for the EU's new privacy regulations, the GDPR.  As part of that I have spent a bunch of time with tech teams, attorneys and others unpacking not only what the regulations require in different cases and what it will take for companies to comply, but trying to think about ways to make data security and privacy compliance easier for small startups, assuming that new regulations in the US are looming. This is not a post about cryptocurrencies and whether all ICOs are securities, or about how we should be thinking about solving privacy and security problems online.  It's about getting comfortable in that sweet (& sour) spot where you know a little (or a lot) less than everyone else in the room about whatever problem you are trying to solve. I am not an attorney, am not a PhD computer scientist, am not an economist or monetary policy expert, and am not an MBA and don't have a background in finance. Yet every day I find myself in the middle of some set of issues drawing on all of these specialties, typically with people who are seasoned experts in one area or another.   It can be intimidating, but it's also incredibly stimulating and exhilarating. There have been many times during my career where I have stood at that crossroads and had an opportunity to either stay in the comfort zone or wade into the discomfort zone (starting at USV 6 years ago was one of those moments).  I'd like to say that I've always headed straight to the discomfort zone, but I can't say that that's true. It has taken time for me to get comfortable being uncomfortable. One of the great things about working in the discomfort zone is the ability to be honest about your limitations -- in a room full of lawyers, leading with "i'm not a lawyer and you guys are the experts, so..." can be really freeing.  Once you can do that, you can open yourself up to lots of interesting and important situations. A while back, I tried using this heuristic for prioritizing my time: what's the hardest thing I can be working on right now?  That has helped me guide myself to the discomfort zone more and more, which I will keep doing as much as I can.  


A bigger container

An idea I like from Zen Buddhism is becoming a Bigger Container.  My understanding of the idea is this: There are a lot of difficult/bad/sad/scary things going on in the world, ranging from serious global issues, war, famine, terrorism, etc; to things in your city like homelessness or joblessnes; to things in your family, like difficult relationships or substance abuse; to tiny things in your life like a daunting project at work, or your inbox, or going through bills or cleaning your desk. It's hard to open yourself up to all of these things, because the are overwhelming and scary.  So the easy thing to do is turn away - to avoid. Becoming a bigger container means making space within yourself to face an increasing number of these things, with compassion and without fear.  Being able to hold them and look them in the eye without any one of them grabbing control of you, carrying you away or breaking you. From the reading linked above:

"What is created, what grows, is the amount of life I can hold without it upsetting me, dominating me. At first this space is quite restricted, then it’s a bit bigger, and then it’s bigger still. It need never cease to grow. And the enlightened state is that enormous and compassionate space. But as long as we live we find there is a limit to our container’s size and it is at that point that we must practice. And how do we know where this cut-off point is? We are at that point when we feel any degree of upset, of anger. It’s no mystery at all. And the strength of our practice is how big that container gets."

When am most proud of myself, I am able to make space within myself to deal with hard things.  To look them in the eye, be with them, and not look away.  When I'm frustrated with myself, it's often because I'm avoiding doing this. The visualization that works for me is that when you become a bigger container -- when you can generate some perspective -- each of these individual things becomes smaller by comparison; less dominant. It can be hard to do sometimes but I find it to be a really useful construct.


You need a budget

I've written for a long time about my desire to re-build personal finance infrastructure in ways that benefit people with the least money.  We see new personal financial products all the time targeting high value customers, but it still feels like they are ignoring a huge, and important part of the market: people scraping by living paycheck-to-paycheck.  This is a huge slice of America and the world, and I believe that tools that serve this population well will not only make a huge positive social impact, they can build huge businesses. One such product that I've started using recently is the very aptly titled You Need a Budget.  I have tried nearly every app out there that tries to help people get a handle on their moment-to-moment finances, but this is the most thoughtfully designed (and I suspect, the most effective) one I've seen so far.

YNAB is full of product nuances that show that they've thought deeply about how people use money, and how to help people craft effective budgets.  The main idea, of course, is that you need to start with a budget.  The nuanced parts are the way YNAB helps track budget categories, map expenses against them, make tradeoffs when categories are overbudget, and start to understand new concepts like aging your money. Having used apps like Mint in the past, which work on the same ideas, I've found that YNAB has figured something new out, which is how to make tracking your money, and tending to your budget, a daily activity.  The YNAB mobile app makes it easy to categorize expenses as they come in, on a daily basis.  It's this daily check in that both makes the process less overwhelming (since you're only dealing with a handful of transactions at once) and potentially change-making, since you are reflecting on your budget and expenses in real time. Getting a grip on finances is hard.  It's emotional, complicated and often overwhelming.  I like the way YNAB demystifies the process and provides a real helping hand.  I hope we see more things like this come to market.


From a labor mindset to a capital mindset

I've been quiet on the blog lately -- writing is one of those things that's hard to build a habit for, but always pays big dividends when you do it.  Every time I've gotten into a good blogging rhythm I am undoubtedly surprised by the feedback I get (good and bad!), but more importantly, by the ripple effects.  Writing is capital -- you work to make it, and then it works for you. As someone who likes to work with his hands (both in the analog and digital worlds), I feel pretty deeply connected to both labor and to capital.  The process of making something (a table, an app, a blog post) can be deeply satisfying, and then the follow-on effects from that thing existing can (in the best cases) be very high leverage. I would say my hands-on nature is both a blessing and a curse when it comes to this.  Because I like "making stuff" I'm often drawn into projects where I might be better off hiring (or inspiring) someone else to do it, or delegating it somehow.  When it comes to producing capital, sometimes actually the less you "do", the more you can accomplish.  I think of this as learning to develop a Capital mindset, over a Labor mindset. Of course this relates to money as well. For the longest time -- I think this was just my foundational mental model -- I intuitively understood the idea that you work, and you get paid.  Labor.  Paid for your time.  Despite the fact that I have worked for a  long time in the software economy (and of course now, in venture capital), I had to overcome this idea of labor being the thing.  For instance, I spent a lot of time in my early twenties as a freelance developer, building apps (capital) for others, but just getting paid for my time. Maybe this is intuitively obvious to other people, but it has taken me some time to turn the corner and understand the value of, and the power of, capital.  **Especially** capital you can build through your own efforts, like writing, or coding, or making music, art, etc. I feel like it's an overall very powerful frame, and is especially helpful when it comes to prioritizing your own time & activities -- whether you are the CEO of a company, or a guy/gal sitting in your living room. With that in mind, here is my first blog post of 2018.  Here's to a great year, everyone.