A few years ago I wrote about one of my favorite product sayings: “Half, Not Half-Assed“, which comes from my favorite book on product development & teamwork, Getting Real (from the team behind Basecamp). I actually first got hooked into this thinking when I saw one of the Basecamp founders, Jason Fried, talk at a web design conference back in 2004 and it was a pivotal moment in my career (thanks Jason!).

I was reminded of that idea today, as I was working on a side project (an internal tool for USV). In this particular case, we had built a version of this tool a few years ago, but basically abandoned it because we could not build a good workflow around it. Looking back, the diagnosis on why was that it was overbuilt: too complicated, too much. And implemented in a way such that we just didn’t bother to keep up with it. In other words, half-assed, rather than “half”.

In version 2.0, I cut the scope and complexity down by 90%. Every new piece of detail went through the filter of “what’s the trade-off between nice to have and this will be sustainable to maintain.” But further, it was really easy to make design decisions because most of them had been made already before, and the key technical challenges had been worked through.

So it was very easy to build version 2 in a lighter, leaner, meaner way.

I am a big fan of iterating and taking things step by step. And in this particular case, it was that process that led the version 1 to be really interesting, but also a bit meandering, bloated and off target. Because the iterations were also an exploration.

This time, It felt good to do an iteration that started over, but from the place of wisdom of having built it all once before. Iterating from scratch. Very satisfying in its simplicity, and hopefully it will be on-target this time!

Today I’m finally switching off of Capital One because of their broken integration with Plaid. For those who don’t know, Plaid is a service that makes it easy for apps to connect to your bank account. So, if you want to do anything interesting that your bank doesn’t offer (spending analytics, smart transfers, etc) and you want to use a cool app to help you with that, you need Plaid to do it. Capital One has been notoriously bad with its Plaid integration, and people (including me) are frustrated.

I have been a long-time Capital One customer, from back when the online savings product was with ING bank. I originally joined for low fees and better than average interest rates. But I ended up staying because of how easy Capital One makes it to open and manage multiple accounts.

It has been a long journey for me to manage personal finances. For a long time, I had jobs that didn’t pay very well and managed to rack up a substantial amount of debt in my 20s. For the past 10 years I’ve managed that down, and a key tool for doing that has been breaking my financial life up into separate buckets, for various saving and spending goals, and automating as much as possible. This is a trick I learned from the amazing Ramit Sethi and his I Will Teach You to be Rich blog, which I read regularly back in the day.

The way I set it up is roughly this:

Paycheck comes in, gets split 3 ways (this is handled at the Justworks layer): 1/ primary spending account, 2/ overflow spending account, 3/ recurring bills & savings account. Each of these three accounts are at different institutions.

From there, all major bills (mortgage, insurance, car payment, utilities, childcare, etc) are paid from the recurring bills and savings account. And further, that account (until recently at Capital One) splits further into a bunch of smaller savings accounts for dedicated purposes (vacations, home improvements, certain kids activities, general savings, etc — I have about 8 of these I use regularly, and the transfers also happen automatically. I also auto-stash into my Stash account on a weekly basis.

The overflow spending account is for non-recurring large items (for example, some kids activity or a medical bill).

The regular spending is for things like groceries, eating out, random purchases. Essentially, what is left over after big things are handled.

It has been a lot of work to set all of this up in a way that makes sense. But it has been worth it, because now we have a system that keeps everything organized — not just in terms of budget categories and analysis, but in terms of actual accounts which we can spend out of and save towards.

And even so, using additional tools to help (like Personal Capital for overall analysis, or Zeta for couples-based tracking, or Astra for smart transfers) has not worked because of the broken Plaid integration with Capital One. So enough of that; goodbye Capital One.

The broader point is that financial analysis isn’t enough. Moving money is a core part of managing it. I don’t know how typical a setup mine is, but I have accounts at 5 different institutions just for basic spending and saving, not counting credit cards, investment accounts or crypto. I heard recently that the average consumer has accounts at 4+ financial institutions — I don’t believe this is a high-end phenomenon.

When I look out at the landscape of personal financial products, so many of them focus either on analyzing money or managing/moving it, but not both. Doing this in a holistic manner is difficult, especially with accounts across institutions. But it seems to me that it is the key to having an actually organized and manageable financial life.

I am feeling reflective at the beginning of this new year, as often happens to me. Today and yesterday especially so, as the kids are back to school but USV is still on break, so I have a few really free days to catch up, reflect and think.

I’m about to go out on a walk with Frannie, as we did yesterday. There is something so simple and helpful about just getting outside, getting some fresh air (especially in New England in the winter, but it really works anywhere), and moving the body a bit. Just the simple act of going outside is surprisingly powerful.

I am reminded this morning of our dear friend Sam who passed away nearly 13 years ago. Sam was a person who felt the world more than most people, both the beautiful and the painful. I remember from his service a story about the importance to him of the concept of “Write, and Go Outside.” I don’t remember perfectly, but I believe it was a teacher of his who gave him this mantra as a way to help when things felt tough. The idea has really stuck with me.

Write, and Go Outside feels especially important at a time in the world where it is so easy to “consume (read) and stay inside”. Both the “write” and “go outside” parts are about choosing a singular focus and a physical act, unplugged from other distractions. Both tend to make you feel good, for that reason and others.

Yesterday, I mentioned the Volt Planner, which I use every year to make long-, medium- and short-term plans. One of my goals for 2019 was to spend more time outside, in particular with my family. I have done a decent job of that and will step that up this year. One of my goals for 2020 is to focus more on writing, in all of its forms.

With both of those goals in mind, I’m hitting publish here and heading outside for walk.

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.

As I make my way through the various predictions & reflections that accompany the new year, one stands out: the EFF’s 2019 Year In Review, entitled “Dodging Bullets on the Path to a Decentralized Future“. I have long been disappointed that there have seemed to be two separate and parallel conversations going on: the “traditional” digital rights / internet freedom community talking about “re-decentralizing the web” and the blockchain/crypto community working on the same thing. I like the EFF’s recent work because they are connecting the two conversations, and their year in review is a good place to start on that.

A key link in the EFF review is to Cory Doctorow’s work on Adversarial Interoperability, which studies the history of interoperability of technical systems and all of the commercial, legal and policy battles that haven ensued because of it.

In this post in the Adversarial Interoperability series, Cory details the different kinds of interoperability and the dynamics around them. His mantra is “Fix the Internet, not the Tech Companies” and I couldn’t agree more.

I believe, and we have said at USV many times, that driving interoperability is the best and most effective way to limit the power of big tech companies, and that in today’s environment we should focus on “breaking up the data, not the companies.”.

When I talk to regulators, lawmakers and policymakers, I often use this diagram (credit to Placeholder for the underlying graphic):

Which shows that from a historical perspective, these “open” or “interoperability” technologies have been the driver in breaking up each era’s dominant monopoly.

It’s the same today, and Cory’s and EFF’s excellent work on the subject adds a lot of depth to the analysis.