The Last Four Years

I haven’t shared an update here on what I have been up to since the end of the Obama Administration, so now’s a good time to write some of this down.

Like many, I was extremely worried by Donald Trump’s election to the Presidency. Doing all I could to get to a different result in 2020 drove much of my work since 2017. I also tried to extend my non-profit work and grow my fundraising ability because I came to the sad realization that my fundraising ability is worth at least as much, if not more, than my strategic advice to the non-profits I care about (and I am not very good at fundraising).

All of the projects below were overlapping, and most were not full-time. They combined to be a ridiculous amount of work sometimes, and nearly no work at other times. The list below is in somewhat chronological order.

  • Thanks to Megan Smith and Tom Perez, I got to help bring in Raffi Krikorian to be the first Chief Technology Officer of the Democratic National Committee (DNC). Tom understood the value of tech and how badly Democrats were being beaten in this regard. He helped re-up tech within the DNC and the team has done amazing stuff under Raffi and Lindsey Schuh Cortes, and now Nellwyn Thomas and Kat Atwater.

  • Thanks to Mike Yang, Haley van Dÿck and Mikey Dickerson, I helped found and was its General Counsel for the first year. Alloy’s mission was to help improve data and technology for the progressive ecosystem. We were originally focused on legal data sharing among progressive organizations and campaigns, but once the Democratic Data Exchange (DDx) got up and running, and based on feedback from potential users, we shifted to improving basic data availability and update frequency, as well as voter registration. The wonderful Kendall Burman took over as General Counsel on January 1st, 2020. Alloy is now in talks with CiviTech to have them carry on our mission. I’m thankful for the incredible people we were able to hire, many of whom I had not met before, and for the fact that Alloy seems to have had a positive impact on the election and Georgia runoffs through its set of partners.

  • While working on the tech and data side for Dems and progressives, I also got drawn into, and did some funding of, and fundraising for, a wide set of organizations and candidates. One of the most amazing things to come out of 2016 was the incredible set of new organizations and candidates. The narrow 2016 loss to the person who would become one of the worst presidents in American history was also a catalyst for a bunch of more established organizations to do great work. I am really grateful to the many, many people who shared their wisdom and time as I was getting up to speed (I still am). I am also grateful to the folks who did the work of registering a record breaking number of new voters, helped to elect good candidates, including President Biden, and then protected those victories against the efforts to undo them. Before 2016 I had no idea of the richness and variety of people and organizations that are part of the big tent of the progressive community and Democratic party. It looks chaotic at times, but I was constantly blown away by the talented, committed people who work in politics. Many do so without much compensation or limelight, and nearly everyone I met shared a basic common purpose that was tied to getting real benefits for people.

  • Thanks to Eric Goldman, Adelin Cai, Clara Tsao, and Denelle Dixon-Thayer, I got to help found the Trust & Safety Professional Association (TSPA) and the Trust & Safety Foundation Project (TSF). I’ve wanted to do something like this for fifteen years but it took others to push for their formation.  I had the good fortune of getting to know some great Cognizant folks, including Kristen Titus and Davis Abraham, and many others while fundraising for TSPA and TSF. And then I got to talk to many old friends and make some new ones as we considered who would be the perfect first Executive Director. I couldn’t be happier that Charlotte Willner took the job. Being so immersed in a community I have been around for a long time was deeply satisfying. And the collective “FINALLY!!!” we heard on launching underscored to me that community building is important and should never be put off.

  • I’ve also spent a good amount of time working as a Board Member at Creative Commons and Data & Society. They are two great organizations from which I have learnt a lot. I am the Board lead for fundraising at both places, and so have been asking many of my friends for money to support their wonderful missions. Being a Board Member is also something I am still learning, and I have been thankful to get to watch others who are better at it than I, and to have such an intimate view of these two very different organizations during these exceptional times. I still also exist as a fanboy for the work that Creative Commons and Data & Society each do, so it is great to feel like I am helping them achieve their goals.

  • More recently, thanks to Yohannes Abraham, DJ Patil, David Recordon, Ginny Hunt, Mina Hsiang, Eric Hysen, Clarence Wardell and many others, I was lucky to get to work on the Biden Transition (and with my old friend and mentor Nicole Wong). That was a huge privilege and again underscored that working with a great team, on hard problems, with one clear purpose is a wonderful experience. I am so pleased for the folks who are going into government (and will try to write more about some of them soon). If you want to learn more about transitions, Transition Lab is a fabulous podcast and episode 46 (!!) is with  Yohannes.

I would not have thought in 2016 that I would have spent a large portion of the next four years in politics and political tech. Nor would I have thought I would have helped found three non-profits. So while I continue to be on the Board at Alloy, Creative Commons, Data & Society, TSPA and TSF, I really don’t know what the next of these updates will look like. After President Biden’s heartwarming inauguration, I am very hopeful for us all.

Finally, if you got this far and are wondering what to donate to in the new year with the hellishness of COVID still in full swing, please consider using this tool to find your local food bank and donate. I have a longer and slightly older list of COVID charities here, but know that many are having a very hard time getting basics like food and shelter, so please be generous.

First Amendment and Earlyish Content Moderation

This thread got long, so here is a perhaps more easily read copy of it:

One thing that came up on #InLieuOfFun that I didn't get the chance to answer was @klonick asking about whether the earlyish content moderation was based on "First Amendment Norms." I think the answer to that is a bit more complicated than it may seem.

Am speaking from my experience at Google (outside counsel 2000-3, inside 2003-9) and Twitter (2009-13). Others may have used different approaches.

By "First Amendment Norms" I take @Klonick to mean that the platforms were thinking about what a govt might be OK banning under 1st Am jurisprudence in the US.

Of course, the platforms aren't govt & 1st Am doesn't speak to what govts ban, only what they cannot. But still...

To restate, "1st Am Norms" might be something like platforms ~only~ removing what was removable under US 1st Am jurisprudence ~and~ had been generally made illegal in the US (or elsewhere if doing geo-removals), irrespective of 47 USC 230.

First, lots of content removal was simply not cognizable under 1st Am analysis. Spam was a significant issue for Google's various products & Twitter. I don't know of a jurisdiction where spam is illegal & it is unclear whether a govt banning it would survive 1st Am.

Nevertheless, spam removal (both by hand and automated) was/is extremely important and was done on the basis of improving user experience / usefulness of the products.

Similarly, nudity & porn were sometimes banned for similar reasons. Some types of products (video) might be overrun by porn and be unwelcome for other uses / users if porn was not discouraged through removal, especially early. And yet, the 1st Am is quite porn-friendly.

There were also some places that might look like they fit 1st Am norms but were really the platforms deferring to courts. For example, a court order for the removal of defamation would result in removal (irrespective of §230 immunity).

You can square that w/ 1st Am norms but the analysis was not based on what types of defamation or other causes of action the 1st Am would allow, but rather deferring to courts of competent jurisdiction in democracyish places.* <- this last bit was complicated + inexact.

Where we refused, it was often about fairness, justice, human rights, or jurisdictional distance from the service, not the 1st Am per se.

All of that said, I do think there were times when we look to the 1st Am (and freedom of expression exceptions more generally) to try to grapple with what the right policy was for each product.

For example, understanding what types of threats we would remove from Blogger, we used US precedent to guide our rules. My memory is hazy as to why, but I believe it stemmed from two factors: (a) that we felt that we were relatively new to analyzing this stuff but that

the Courts had more experience drawing those lines, and (b) that the Courts and Congress, being part of a functioning democracy, might reflect the general will of the people. These were overly simplistic ideas but that's my memory.

In summary: while I think there is something to the idea that 1st Am norms were important, I think the bigger impetus was trying to effectively build the products for our then users -- to have the product do the job the user wanted -- within legal/ethical constraints. But...

But, we did all of that from a particular set of perspectives (and that's what the 1st Am norms are probably part of) that was nowhere near diverse enough given the eventual reach and importance of our products.

I'd love the read of others doing or observing this work at the time on whether I'm misremembering/misstating @nicolewong @goldman @delbius @jilliancyork @adelin @rmack @mattcutts @clean_freak @helloyouths @dswillner +many more + those who aren't on Twitter… (please tag more)

And, in case you want to see the question I'm referring to, from @Klonick on #InLieuOfFun look here at minute 22:11 (though the whole conversation was good):

Product Counsel: Origin Story

This post is co-authored by Nicole Wong and I.

One of the best jobs either of us have ever had, didn’t exist before we had it.

We both started as lawyers in Silicon Valley firms. Alexander joined Google in May of 2003 as an IP Counsel. Less than a year later, Nicole joined as Senior Compliance Counsel. For both of us, the pitch was some combination of a bunch of our favorite areas of law, including privacy, content, consumer protection, copyright, open source, and jurisdictional issues as the company’s product ambitions and international footprint grew. As in many start ups, our actual jobs were to do whatever needed to get done.

Gmail launched in April 2004 (on April Fools Day -- don’t do that) and that marked the beginning of Google’s explosion in terms of number of products, including Book Search, Maps, Chat, and the acquisitions of DoubleClick and YouTube. Google grew not only in terms of its product offerings, but in number of users, revenue, the number of countries it was in, and its impact in the world. The stakes got MUCH higher while product, operational and, of course, legal complexity exploded.

We both set to work trying to figure out how to help Googlers launch successful products that were legal (at least in the countries where we operated). We each had some experience with this as outside counsel, and we were both pretty unsatisfied with the typical model of legal review for products.

That model was taken from big companies which historically treated legal review like part of an assembly line (towards the end). The product teams would develop products and then check in with a line of legal subject matter experts for sign-off before launch. For example, a product that matched people to their perfect pet might get designed, written, tested, and be ready to launch when it was then taken for review by a commercial lawyer for the terms of service, an intellectual property lawyer for trademark and copyright clearance, a patent lawyer in case anything new had been invented, a regulatory attorney for regulatory compliance (sometimes including privacy), and maybe an export control lawyer and a similar set of experts in the countries where the product was launching. Law firms are typically departmentalized in similar ways, aligning along legal subject matter specialization, and consequently smaller companies who don’t have in-house counsel often need to hire multiple specialized lawyers.

There are four major problems with this process:
  1. legal approval in each area is binary and too late: by the time the product is built, there is a large amount of pressure to launch with little ability to make more than cosmetic changes to the product;
  2. legal approval is too fragmented: a product might need several different legal approvals (or rounds of consultation and then approval) from in-house and/or outside counsel. That would take too long and be very inefficient for a product team, which would have to explain the product to each new counsel. On top of that, no counsel would be able to weigh risks across domains to come up with more holistic tradeoffs.
  3. legal would understand the law but not necessarily the product: dividing up legal counsel by area of legal specialization means that each lawyer has a depth in law and a breadth in products.
  4. legal becomes “them” versus the product team’s “us”: last minute binary review by people who don’t know the product or the product team unnecessarily forces misalignment between the team trying to get something done for the users and the business, and the lawyers. That misalignment can result in all sorts of bad, from simple misunderstandings to adversarial behavior.
Taking our lead from Google’s first lawyer Kulpreet Rana and the way many commercial legal teams already functioned, we started working at the beginning of the product process rather than the end. We joined product teams and tried to get deep understanding of the product goals early, so that we could help them meet those goals with the right legal considerations. That meant going to a lot of meetings where product teams struggled to define and execute on new product and feature designs, raising legal issues, and working through alternatives. We tried to help our teams remove obstacles to their launches and refine launch processes so that the teams could deliver more easily and understand legal constraints that would result in us later blocking launch. We consolidated legal review so that the team could get answers from fewer lawyers and feel that those lawyers could properly balance risks and benefits in a holistic way. That meant that each of us would be responsible for a set of products on the core legal issues those products would face at launch.

This approach is not without downsides. Perhaps the biggest is that product depth can come at the expense of legal depth, which meant that we sometimes incurred costs working with outside counsel and experts in legal areas and countries outside of our expertise or missed legal issues. However, we remain convinced that the vast majority of significant mistakes in-house departments make in our industry are the result of not understanding the product rather than not understanding the law. Another downside is that while being part of the “us” of a team is satisfying, can result in a much better understanding of a product, and better teamwork in identifying and fixing problems, it can also mean you are in the team “groupthink” as opposed to removed from it. Careful attention must be paid to all of the ways to reduce groupthink and it is imperative that you actively seek input from folks outside the bubble if you are going to effectively understand the various impacts your product decisions are likely to have in the world. We found it really helpful to discuss product features with advocacy organizations and they frequently improved the products. But, there were also definitely times we screwed up.

The actual role of “product counsel” grew out of the fact that our previous job descriptions didn’t make much sense given how we were doing our jobs. So we started thinking through names. Originally, we liked “launch counsel” because it was active, aligned with what our teams were trying to do, and could describe a bunch of different areas of law. Eventually we settled on “product counsel” because it was even more descriptive of the alignment we hoped for, and was tied to the whole lifecycle of a product from idea generation through maintenance and refinement, not just launch.

Our first job posting was in February 2004. It read:

Google is looking for experienced and entrepreneurial attorneys to develop and implement legal policies and approaches for new and existing products. The Product Counsel will be responsible for a portfolio of Google products across many legal subject areas including privacy, security, content regulation, consumer protection and intellectual property. Indeed, the only product legal matters with which this position will not be deeply involved are those that are strictly patent or transactional in nature, which are handled by other existing Google lawyers.

Passion for and deep understanding of internet.
Very strong academic credentials.
Solid understanding of Internet architecture and operation.
Ability to respond to questions/issues spontaneously.
Demonstrated ability to manage multiple matters in a time-sensitive environment.
Strong interpersonal and team skills.
Excellent interpersonal skills, dynamic and highly team-oriented.
Flexibility and willingness to work on a broad variety of legal matters.
Superior English language writing and oral communication skills.
Sense of humor and commitment to professionalism and collegiality are required.
California Bar

Note the many mistakes in that posting. For example, the Internet is referred to with both lower-case and upper-case capitalization (back then I was incorrectly not capitalizing it). Ug.

Even so, we were very fortunate to recruit an amazing set of folks at Google to become the first Product Counsel. Some of the originals who defined the role were: Glenn Brown, Trevor Callaghan, Halimah DeLaine, Brian Downing, Gitanjli Duggal, William Farris, Mia Garlick, Milana Homsi, Susan Infantino, Daphne Keller, Lance Kavanaugh, Courtney Power, Nikhil Shanbhag, Tu Tsao, and Mike Yang (in alphabetical order). The team was eventually about forty-strong by the time we left and worked across many countries. The idea of it spread relatively quickly in the industry and now LinkedIN lists thousands of product counsel.

Product Counsel, particularly when we were still doing it and not just managing people doing it, was one of the best jobs we have ever had.

COVID-19 Donation List

This list is designed to help people give money in a time of COVID-19. There are many many many great projects out there helping people. Sometimes they need people to help with specific skills or equipment but all also need money. For each category listed below, there are some recommended charitable organizations. There are also some writeups, many of which were sources of recommendations. Please give generously.

This list is somewhat long so to help you find something that resonates with you. BUT, if you don’t have the time or inclination to look through the whole list, you can donate to the World Health Organization fund or Feeding America easily (just click & donate) or choose a local community foundation fund from this map. If you have an extra second, please tweet or otherwise share that you donated (feel free to tag me and I’ll retweet). Being vocal about donating will encourage others to do the same and increase the value of your donation.

One other note specifically for those of you (like me) who are privileged to have a Donor Advised Fund (DAF). You may have funded that DAF a while ago with the intention of figuring out how to give away the money over time. You may not have given much away because: life. Now is a very good time to use your DAF to help. You put money in to give it away, not to watch it grow. Your money NOW can make a big difference. Please consider choosing a goal that meets the urgency of this crisis and pushing yourself to give that goal away. Each recommendation below includes the organizations’ EIN so that you can easily give from your DAF (I generally give unrestricted funds, but you can also specify programs when you submit). I have also included recommendations from some DAFs and community foundations at the end. [If you don’t know what a Donor Advised Fund is, don’t worry, you are normal! You don’t have to know about them but if you’d like to, here are some resources: explainer from Wikipedia, explainer from Fidelity (a provider of them), and a critical take from the NYT.]

Finally, this is an evolving draft. If you have suggestions or questions, shoot me a note. I’m @amac on Twitter.


Hospitals, Doctors, Nurses & the Front Line
This is a large fund (>$100M so far) that is run through the UN Foundation.
EIN: 58-2368165 (UN Foundation)

EIN: 58-2106707

Developing country care & testing.
EIN: 04-3567502

Supplies to medical professionals to help them protect themselves.
EIN: 95-1831116

Logistics and shipping for front line supplies.

EIN: 13-3433452

EIN: 56-2273242

Resources for health systems focusing on resolving inequity.
EIN: 45-0484533

Meals from local restaurants to health workers.
EIN: 27-3521132  (through World Central Kitchen)

Food & Other Relief For Economically Disadvantaged
Community Foundations have a history of local giving and the staff to review potential grantees and get the money quickly in times of crisis. Consider giving to your local one (found via the map above) and/or one in a community that you care about. For example, for me that’s the Maine Community Foundation (donate EIN: 01-0391479), they have already given a wave of money to good local institutions.

They also run the very good Find Your Local Food Bank resource, which allows you to give locally.
EIN: 36-3673599

Many seniors use this program.
EIN: 23-7447812

Keeping children fed.
EIN: 06-0726487

EIN: 52-1367538

They also fund Frontline Foods (see above).
EIN: 27-3521132

Gives cash to people who need it.
EIN: 27-1661997

“Emergency financial relief for students, immigrants, and workers left out”
EIN: 20-8993652

Update: @mredshirtshaw has a good thread on a number of South Dakota Tribes' COVID-19 funds. She points to South Dakota because of the lack of a shelter-in-place order there.

Refugees and Displaced People
Consider directing your donation to the Matamoros Project.
EIN: 81-5163032

Sidewalk School [donate]
EIN: 80-3405530

Update: A friend who knows more than I do about refugee issues points to the following two orgs:
International Rescue Committee, Signpost Project [donate]
EIN: 13-5660870
Signpost is designed to help refugees get good information during the crisis which the IRC's president says is one of the most pressing problems.

Refugee Advocacy Lab at Refugees International + International Refugee Assistance Project (IRAP)[donate: Refugees International or IRAP]
EINs: 52-1224516 (Refugees International) or 82-2167556 (IRAP)
Matching refugees with healthcare experiences with states that need healthcare workers and the certifications they need to practice, thereby helping both.

I have a friend who works specifically with communities on the El Paso / Juarez border. There they recommend:
The ACLU also has a good article about donating in this category.

I don't have a perfect recommendation to directly help those in prisons and jails but Civil Rights Corps [donate] and Institute for Constitutional Advocacy and Protection [donate] are fighting some of the legal battles around this. Please ping me if you have others.
Update: The Reform Alliance has a special COVID-19 action page to attempt to get governmental attention to this problem. Thanks @rklau.

Domestic Abuse
RAINN runs the US National Sexual Assault Hotline.
EIN: 52-1886511

EIN: 91-1081344

EIN: 77-0155782

EIN: 13-1760110

Keeping children fed (also in Food above).
EIN: 06-0726487

Also in Food above.
EIN: 52-1367538

EIN: 13-3468427

US Focus on learning.
EIN: 52-1779606

Miscellaneous and Support
Creative Commons provides the licensing infrastructure for a lot of the open content being relied on in this crisis and was part of creating the Open COVID Pledge to help ensure that people fighting COVID can worry less about patent lawsuits. Disclaimer: I am a Board Member.
EIN: 04-3585301

Tech is becoming even more important now. Data & Society studies and critically unpacks the social implications of data-centric technologies & automation so that their impact is less harmful / more beneficial. Disclaimer: I am a Board Member.
EIN: 46-2904827

Good information is critical to combating COVID and journalists are risking their lives to get it to us. 
EIN: 13-3081500

Support their just launched fund to give legal support to local and regional reporters.
EIN: 52-0972043

Other Good Writeups & Resources
Community Foundations have expertise to help get money to local charities in times of crisis. This map will help you find one in an area that you care about.

Amelia Nierenberg, Don’t Need That $1,200 Stimulus Check? Here Are Places to Donate It, New York Times, March 27, 2020 but updated as well.
Great round up and source of a bunch of the above.

Before COVID-19 was the focus but still very relevant.

Denise Hearn, COVID-19 — where to give money now, April 2, 2020.
Bloomberg Beta, Schmidt Futures, and The Stanford Center on Philanthropy and Civil Society put this together.

Update: Isaac Chotiner, The Danger of COVID-19 for Refugees, April 10, 2020.
Q&A with David Miliband, the president and C.E.O. of the International Rescue Committee about the specific issues raised by COVID-19 in refugee communities where he highlights disinformation as an important issue.

Disaster Philanthropy, COVID-19 Coronavirus, April 13, 2020.

Fidelity Charitable, How to help: Novel Coronavirus.

10 Years of Retweet

10 years ago today, Twitter launched “native retweet” and significantly changed how people experienced the Twitter timeline. IMHO it was a huge and relatively gutsy change. I’m writing this post to explain what changed, and why I like a particularly controversial aspect of it -- strangers in the timeline -- so much. I hope it will encourage others who were at Twitter at the time to share their stories.

First off, imagine the Twitter of early 2009. It was a simpler Twitter in SOOOOO many ways. Timelines were a reverse chronological set of 140 character tweets. There were no ads. No images. And no mobile phone client from Twitter.  Barack Obama had just been inaugurated.

Late 2008 screenshot from Huynh, Terence,
Twitter releases new design, more customisable,
TechGeek, Sept 20, 2008
People were already retweeting each other through a convention of using the letters “RT” and the original user’s username, and then the tweet. Retweeting the President’s election victory tweet would have been something like “RT @BarackObama We just made history. All of this happened because you gave your time, talent and passion. All of this happened because of you. Thanks.” If you followed me and I retweeted that, you’d see my avatar and that text. Nothing would link my Tweet back to the original, and there was nothing stopping me from editing the original and misquoting it. In fact, even that retweet of @BarackObama would have needed editing so that it could fit in the 140 characters. Still, the convention was used and useful.

On August 13, 2009 @biz made a short blog post pre-announcing a new retweet feature so that the Twitter client developers (none of whom worked at the company or were paid by Twitter) would be ready for it when it rolled out on At least one of those developers already had a retweet button that made retweeting easier, but the new feature @biz announced was different. It was simple and revolutionary. Now when I retweeted @BarackObama my followers would see his tweet as if they too were followers of @BarackObama for that instant. They would see his Tweet as if they followed him -- in their regular timeline -- but with an acknowledgement to me, and as if it had been tweeted when I hit the retweet button. As @Biz described it:

"Let’s say you follow @jessverr, @biz (that’s me), and @gregpass but you don’t follow @ev. However, I do follow @ev and the birth of his baby boy was so momentous that I retweeted it to all my followers.

Imagine that my simple sketch is your Twitter timeline. You’d see @ev’s tweet even though you don’t follow him because you follow me and I really wanted you to have the information that I have." Photo and quotation from Stone, Biz, Project Retweet: Phase One, Twitter Blog, Aug. 13, 2009.

It made retweeting much easier,* but it also meant that users saw the faces of people they didn’t follow in their timeline (internally we called this the "strangers in the timeline" phenomenon). Retweets were also displayed based on the time of retweet, not the time of the original tweet (even though the timestamp was still the original one), so it looked like the tweets were being displayed out of order. Here’s what it looked like when it rolled out later that year (with a special dialog box to explain to people why they were seeing strange new avatars).

Screenshot by See-ming Lee CC-BY-SA
This was (and is) a big deal for a whole bunch of reasons, but the one that I really appreciate today is that seeing strangers in my timeline made it so much easier for me to find and follow new interesting people. @Ev’s blog post from the time summarizes a lot of the other benefits and concerns that people had about the idea, including his description of the blowback he knew Twitter would face over putting strangers in peoples' timelines. He wrote, “The drawback is that it may be a little surprising (unpleasant even, for some) to discover avatars of people they don't follow in their timeline.” Which avatar to show, the original tweeter's or the retweeter's was a significant discussion and I am really glad the team chose to show the original tweeter as I think it has led directly to my timeline getting better and better over the years.

Anyhow, I’ll leave the rest of the stories about this to others who were closer to the decision and implementation. For now I just want to thank the folks that were there and call them out so that they (hopefully) tell more of the story. My memory is hazy, but I think at least @zhanna, @alissa, @cw, @goldman, @ev, and @biz would have good memories of it. Please share, tell the inside story, and add more folks I missed.

* Despite the ridiculous title, this Buzzfeed article has some good discussion from folks on the cons of the convenience and speed of the retweet button, and ways to think about slowing the spread of harmful retweet cycles while preserving the good. 

Advice for new General Counsels (GCs)

Here’s some advice I give first-time General Counsels (GC) or, as the kids today call themselves, Chief Legal Officers. These are written from my perspective as someone who had worked as an Associate at a law firm and in-house at Google before going to Twitter as the GC. Your mileage should vary.

Being a GC is lonely, you need colleagues.
Once you become a GC you have no colleagues. Your CEO and Board are your boss. You may have lawyers who work for you, but you are their boss. Your colleagues are the other members of the management team, but they don’t really care about legal stuff the way you do. They’ll be friends, but you need to also have GC friends, and you’ll need to find them outside of the company.

Eventually (on my last day), I formed a network of SF Tech GCs that would have been WONDERFUL to have had before I left. At the time I met with a bunch of peers outside of work and they were a godsend. These folks should be struggling like you. That way you’ll feel free to ask them anything and you’ll be as helpful to them as they are to you. They are your support group as well as your knowledge base. Plus they’ll remember being as clueless as you, which will make them good teachers. These are not your mentors. You need good mentors too, but these are your colleagues.

Arabella Mansfield, 1870.
Public Domain image from Wikipedia.
You are the boss and the end of the line.
When you are the GC, you are it. Yes you can “escalate” things to your CEO or Board but doing that a bunch will not build respect with either. For many hard decisions, you are the decision maker. You cannot just let something slide or say “here are three options.” You are being paid to be responsible for this stuff and have an opinion. Also, there are some things that only you can do, especially before you have a team. When the CEO is freaking out about the CFO deciding to go to your biggest competitor, talking to somebody else likely will not cut it. Vacation purity will go down. Stress will go up. You will need a way to deal with that and it is very important that it is not alcohol, drugs, or other bad things.

You are your company.
If you come from being an outside counsel, you may misunderstand the ethical issues involved in being at a company. At an outside firm you might have had a bunch of ways to distance yourself from a bad thing that a firm clients does. You might not work on their matters. Or not advise them on that subject matter. And, in any case, even bad actors need legal defense. When you are in-house that is no longer the case. You are your company. If they do something unethical or illegal, that is you doing it. Another way to say that is that there is no they, only we. So… you need to be VERY comfortable with the company you are joining. Both what they are now and how they might change over the time you are there. Your only remedy will likely be to quit quietly. Quitting quietly is not a good remedy. Especially if you need the job and the money it provides.

Interior of H.A. Goodrich & Co.'s Store. Public Domain
illustration from Fitchburg, Massachusetts
Past and Present
via Internet Archive.

You are the establishment.
You likely came from being a part of a team and not being in the very senior part of management. You might even have complained about the Partners or the management team at your last company. That ends now. You are the management. If the company has a problem, then it is your problem. You whining is not a good thing. You are not a victim and you need to fix what you don’t like, not complain about it. That goes for even things that the CEO or Board do that you don’t agree with. Make sure you had your say. Quit if you need to, but if you are not going to quit, you need to take ownership of it with the rest of management.

You work for the Board (and the CEO).
GCs have a weird dual reporting structure because they represent the corporation, not any particular person in the corporation. Your day-to-day boss is the CEO, but the Board is also your boss and you need a relationship with the Board. This can be tricky because the CEO often thinks of themselves as the only person who “reports” to the Board. You need to have your own relationship with the Board for a bunch of reasons and a wise CEO will understand that your relationship with the Board is helpful to them as well. You should help the CEO manage getting the board deck together and with the basic stuff that goes comes with managing the Board. In that sense you will act a bit like a Chief of Staff and Executive Assistant. You have a legal role too, and may be the Board Secretary as well, but you should do the other, more mundane stuff as well in order to ensure that you are part of the company having a good relationship with its Board. For example, you should have periodic informal meetings with your board members. You should know how many kids they have and where they like to take vacations. FWIW, CFO’s have a similar need for that type of direct relationship.

Crocker Block. Public Domain
illustration from Fitchburg,
Massachusetts Past and Present

via Internet Archive.
You are also an owner of the company & member of the management team. 

Your CEO and the rest of the team will look to you for your legal opinion. That is very important. If you screw that up, you will not be GC for very long.

However, you are also (hopefully) a significant owner of the company through your stock grant, as well as a member of the senior management team. In those roles the CEO is looking for you to have an opinion on what is the right thing for the company to do. If you come from being an outside counsel, you may be used to giving opinions of the form: “Doing X is a legal risk.” or perhaps “Doing X is a legal risk and I would quantify it in the following way.” Once you are a GC you need to be ready to say things like: “Doing X is a legal risk but is important for us to do because Y” or “Doing X is a legal risk that is not worth pursuing because Y.” What you fill in for Y will not be legal analysis but business, customer, user, employee, etc. analysis. Get to know those parts of your business and start making contributions that have nothing to do with legal.

Be careful about acting in your non-legal capacity.
Now that I’ve told you not to only act like a lawyer, I need to flag some important pitfalls. First, you need to do a good job of labeling and calibrating your non-legal advice. You’ll make more mistakes and tread on other management team members expertise in your non-legal role. If you are not clear about it, the management team may start treating your non-legal advice like your legal advice (or vice versa), and that is usually unhelpful. This can be as simple as saying, “this isn’t a legal issue but…” or “there is nothing legal that requires X but…” and “here I’m speaking directly about our legal requirements under the contract.” You needn’t do it all the time, but being able to be clear can help a lot.

Second, we lawyers are somewhat spoiled by the protections that our legal advice affords us under the law. We can have conversations with people that won’t be revealed in lawsuits. When you venture out into the world of non-legal advice those protections fade away. Some lawyers have gotten into bad habits based on their attorney-client relationships and have gotten used to saying really dumb things in email that they (a) don’t mean, and (b) would never let a client say in email. Remember that your non-legal work is not protected by your special status as an attorney. Do what you tell your clients to do. Imagine your email on the front page of the Wall Street Journal.
Legal is a cost center.
If you came from a firm, legal advising was the profit center. Lawyers were extremely important and probably ran the show. That is not true now. You are a support service. Act like it. Don’t waste your clients time (ie. arrive to meetings on time, with an agenda, etc.). Respond to their emails. Do the things you said you were going to do when you said you were going to do them. Provide value. Make sure your internal clients are happy. And, understand that winning at the Supreme Court and establishing precedent are not the purpose of your business. They shouldn’t be your purpose.

Thurgood Marshall, 1976.
Public Domain image from the
Library of Congress via Wikipedia.
Set yourself up to be constructive.
Some people say GCs shouldn’t say no. I strongly disagree. There will be times when you need to say a flat no. Those times will be bad for the company and for you. But the flat no you enforce may be a moment where you are providing your greatest value to the company. Don’t shy away from those times, but don’t welcome them either.

Try to set yourself up so that you do not get into a flat no situation by understanding legal issues early, and by understanding product goals enough to suggest solutions that will meet the product goals and legal constraints.

Understanding legal issues early, particularly in a startup, means having a very good understanding of who is working on what. Many startups spend a large amount of time transitioning from everyone knowing everything to having processes so that people can know what they need to know. That in-between stage is a hard one for the GC. If you find out about a feature launch from reviewing the launch blog post, you are likely too late for a product redesign. Your product team will have spent a bunch of time working and dreaming about the feature implemented exactly the way they have implemented it. They will be looking to you to say yes (or no). That may be a valuable “no” but it will hurt a lot. And if you say “yes but…” then at that point you may only be putting lipstick on a pig. It is FAR better to be able to understand what is going on when the feature is just an idea. Product managers, designers, and engineers are really good with constraints. They design within them all the time. Having them understand the legal constraints and desires when designing is essential. To do that, you need to be really in tune with whatever part of your company first thinks up new features. Google’s first lawyer, Kulpreet Rana’s practice of taking one afternoon a week to just wander around introducing himself to people and asking them what they were working on is brilliant in that respect (and also helps with the culture points below).

Equally importantly, once you see a legal issue, don’t just issue spot. Know enough about what the teams are trying to do to get your hands dirty in a design setting to help them understand the legal constraints and design within them. Sometimes this looks like working with the engineers to implement variable public domain rights for very old books in Google Books and embedding local copyright law into code. Sometimes it is jumping from a legal constraint to value creation, such as when Glenn Brown, Zahavah Levine, and I helped design the YouTube DMCA system to also allow content providers to leave content up and get a share of revenue. There is almost always more than one way to do something. Help your product teams choose the way that helps users and will survive legal challenges.

You have a decision to make about who to hire when.
As you build your team, you need to decide who to hire when. You will eventually be middle management and do very little legal thinking. You also came into this job not knowing most of the legal areas you will supervise. Do you hire what you know first, or what you don’t? Do you start building with someone who could be the next GC, or someone more junior who can churn through more basic stuff so you don’t have to? If the company is getting bigger, do you start with an employment lawyer? There is no right answer, other than that employment lawyers tend to get hired really early because very few GCs love dealing with employment issues, and good employment lawyers are really good.

Your team(s) are everything.
As your team grows and perhaps you take on a few extra responsibilities (public policy, trust & safety, communications, corporate development, business development, human resources, etc.) because you are a competent leader at a growing company, your teams will be much more important than you in terms of the company’s success. Many lawyers never get management training and didn’t start out life wanting to be managers. That is your life now. It is difficult and you need to want to do it extremely well. That means training, intentional focus, and making sacrifices on other things to make sure that you are doing the management part well. It also means understanding, valuing, and actually achieving diversity from the get-go. Start growing your leaders and empowering them. Get out of the way.

If you don’t like management and would prefer to be doing law stuff, being a GC probably isn’t the right job for you.
Clara Shortridge Foltz. Public Domain
image from History of the Bench and
Bar of of California
 via Internet Archive.

You define the culture of the Legal department, and likely the culture and ethics of the company.
Many of you will get the privilege of being at a very small company, or being the first or second attorney at the company. When I joined Twitter we were around 50 people and had one other intrepid lawyer (the great @tyip!). You will define the relationship between the company and legal. You will define what legal is. Those are probably your most important jobs other than ensuring the company continues to exist. If you establish that legal should be consulted last, heard to say no, and then overruled by others without consequences, that will be the way legal is treated by the company for a very long time. If you are teammates who provide value and help get stuff launched, it will be hard to lose that reputation. Make sure that legal’s relationship with the company is something you focus on. Have goals. Do things that help. For example, Ben Lee and I created the Innovators Patent Agreement as a way to signal to engineers that Twitter was in line with their ethics on patents so that legal could contribute to the company’s #1 priority of hiring great engineers. Another one of my favorite hacks is to set up a desk by wherever your team gets coffee for the post lunch afternoon coffee time. Sit there. Answer questions. (Yes, it is amazing how many engineers have “friends” with weird legal issues and need to be told to get a lawyer.) Being a GC is not a popularity contest, but you need to be known and you need to make sure people understand you are on their team, especially when you disagree with them.

GCs are also often the oldest and/or people who have the biggest vocabulary for ethics at the company. I don’t think we are necessarily the folks who care the most about ethics or have the best ethical compass, but we have the hubris / common sense to have been thinking about ethics and how it applies to our work for a long time. That often makes the GC the de facto Chief Ethics Officer. The important part of that often unofficial role is to understand the difference between ethics or values, and law. When a GC says something is OK to do, we sometimes mean legally OK but the company will frequently hear that it is both legally and ethically good. Ideally everyone at the company is thinking about ethics and your founders, CEO, Board, and management team all provide a solid tone from the top on ethics. That is not always the case. You should ensure that you are the backstop on ethics. Consider making that part of your job official. Definitely talk to the company about its ethical responsibilities and always consider those in your analysis. “That’s legal but completely unethical” is extremely important advice from a GC.

You are not an impostor. Nobody was born a GC. No GC knows every area of law. There is no perfect way to manage people. There is no secret to being a GC that is not something that was learned through trial and error on the job. The truly incredible GCs that I have met may have been better at the job than I but they weren’t superhuman. They started out just like me and you.

Finally, have fun. I found being a GC to be really interesting, challenging, and rewarding. I still love the various teams I helped build. I still have trouble not referring to my old companies with the pronouns “us” or “we.” Being a GC can be a phenomenal job (but it is only a job). Congratulations and good luck!

P.S. Thank you to the SFGCs email list for their useful comments on a working draft of this paper. Ken Carter and others on that list have grown it and made it into something great since I left SF. If you are an SF GC, DM me on Twitter (@amac) and I’ll forward to the right person to add you. If you are a D.C. GC, I’d also love to hear from you.

P.P.S. I got another great suggestion for a pic to add to this post, Laura de Force Gordon.
Laura de Force Gordon
Public Domain image via Wikipedia.