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.  

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.

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

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.  

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.

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