From Apple to Bill Fenwick’s impact on my life

Bill Fenwick’s fingerprints are all over my life:

from the Apple devices that I use too many times a day (he incorporated Apple for Steve Jobs),

to the social media platform I plan to use to share this blog post (his firm, Fenwick and West, took Facebook public in 2012);

to the decentralized social media platform I am building,, that attempts to address some of the shortcomings he articulated with current social media;

to the relationships I’ve formed with the community here in Fayetteville, Arkansas, by employing his advice about how to treat people;

and even to the newfound health I enjoy lately after he told me to lose weight because people would always discount my capabilities if I did not.

Bill Fenwick’s death in late 2021 was one of the many that occurred during COVID without the world taking enough notice, but I remember him every day because of the lessons he taught me as my mentor and friend. Looking back, I laugh at myself for not asking him more about Steve Jobs. Everyone else seemed to ask Bill for these stories but I preferred hearing his other stories. I loved it when he would reveal more personal things, such as when he told me how much he loved feeling his kids’ hands on his head and shoulders while he drove his family around (“there were no kids’ seat belt law those days, Henry,” he would remind me, not letting me think that he broke the law in even a trivial way). More than stories though, I loved getting his advice and when he taught me things that may have been basic to him but were life-changing to me. Showing how mysterious life is though, if not for a chance encounter with an ad in a college newspaper back in 1998, I would never have met Bill Fenwick at all and all of those nice moments with Bill would never have come to pass. And more importantly, who is to say how I would have survived one of the worst moments of my life if he wasn’t there to help me?

I made my first visit to Bill’s home back in 2010 during one of the hardest periods of my life. Despite my urgent need to get his advice, the surprise I received after arriving at the address he gave me for his home kept me from going inside. I wasn’t sure I came to the right place. Prior to this visit, I had always met him at Fenwick and West’s offices in Mountain View, Peet’s Coffee in Town & Country Village in Palo Alto or some other public place. I imagined Bill living in a huge, fancy Silicon Valley house; the house I arrived at looked like something a retired school teacher might inhabit—not the man who incorporated Apple for Steve Jobs and invented the shrink-wrap software license. I had successfully pitched him for legal representation for my startup and written for his blog, ValleyZen, but I was more nervous about this upcoming meeting than any of the interactions I’d had with Bill since I first met him fresh out of undergrad in 1998. And for good reason: I was being threatened with Singaporean jail for the actions of my cofounder. As I sat in my rental car outside of this small, but charming, 3BR Palo Alto home, I nervously debated whether or not I should actually go up and ring the doorbell—I was sure I was at the wrong address but I was late and I really needed to talk to Bill. I finally got out and walked to his door, unaware that I would make that walk from the sidewalk to his front door many times over the next 10+ years. When I knocked, it was Bill and he greeted me the same way he did every time: with a firm handshake, a direct look in my eyes with his piercing blue ones and a friendly hello.

When I first met Bill in 1998, I had no expectation that I would ever interact with him again, let alone get advice about staying out of Singaporean jail over his kitchen table. I only knew Bill because I had randomly run across an ad for California’s Judicial Fellowship in UCLA’s student paper, the Daily Bruin. I wasn’t a regular reader of the paper because I was a commuting student who was only on campus a few days a week but for some reason, I picked up a paper that day and saw an ad on one of the last pages for California’s Capital Fellowships program, graduate fellowships for each branch of government (State Senate, State Assembly, Executive and Judicial). The only one with a deadline I could make in time was the Judicial fellowship but it also had the fewest slots: 5.

I would eventually learn the odds were even worse. The Director of the program, Donna Hoenig-Couch, later told me the interview panel had already decided on the 5 people they would choose for the Fellowship by the time of my interview, which was the last of the day. Donna told me that they were all tired and eager for the last interview to be done so they could go home. But the area I proposed to study and assist the Judicial Council with—how to adapt the legal system to the emerging Internet—was compelling enough to get me the final fellowship slot. Luck upon luck; sometimes these are the things that form the foundation of our lives. How scary and wonderful.

It was during this Judicial Fellowship that I met Bill Fenwick, who was a member of the California Judicial Council’s Court Technology Committee. I remember feeling very intimidated by Bill; I was ill-prepared to interact with Bill and the other judges who comprised the committee because of an almost overwhelming case of imposter syndrome stemming from a background filled with immigrant trauma and lower, middle-class neglect. Interacting with Bill was even worse because I could tell all the other judges were a bit scared or intimidated by him. I didn’t have enough knowledge of the world to have full context and appreciation for who Bill Fenwick was; I just knew he scared the people I was scared of and that was enough for me. When I was at his memorial service, it was amazing the number of people who also said they were intimidated by Bill when they first met him. Yet, like me, they all found him to be very gentle and friendly when they stopped being blinded by their intimidation. The thing that stood out at his memorial was how much people felt that Bill believed in them despite them not feeling worthy of his confidence. I think Bill and other good leaders do this: they inspire us to be the people they see us to be.

Despite Bill’s friendliness, the memory of the other judges’ intimidation stuck with me. If those judges were afraid of him, surely they must know something and I should keep my distance too, I thought. This meant I never tried working for Bill’s firm, Fenwick and West. Thankfully, I don’t think he was offended that I never interviewed with his firm while attending Stanford Law School. I didn’t interview with Fenwick and West because I was worried he would feel like I was trying to take advantage of our acquiantence. I later hired his firm when I was at Tenjin so I feel like I made up for that oversight eventually.

After law school, and after my brief stint at Cleary Gottlieb where I attempted to be a corporate lawyer whose job it was to make rich people richer, I interacted more with Bill. I had moved to Hong Kong in 2006 and started a company, Socialutions, that tried to use technology in a socially impactful way. Our first project, WikiEnterprise, was an early combination of Kickstarter and Basecamp: Build it + Fund it on one platform. I pitched Bill for legal representation but ended up choosing to work with Aaron Alter at Wilson Sonsini. Bill and I continued to stay in touch while I lived in Hong Kong to build Socialutions and I would have coffee with him several times a year whenever I flew to San Francisco. Between 2006-2010, I would chat with Bill about what I was seeing in Asia with regard to Internet technologies and how it compared to what was happening in the U.S. I also wrote those pieces for the ValleyZen blog he did with Drue Kataoka (which ended up getting me a freelance writing contract with CNNGo). I remember he was excited for me when I told him Joi Ito, Reid Hoffman and the National Research Foundation of Singapore were going to invest in Socialutions so we could build a user-generated content sharing and licensing platform utilizing Creative Commons licenses called CreationMix. Prophetically, however, both Bill and Aaron Alter weren’t as excited as I thought they would be because of prior experiences in Singapore.

And so it was that Singapore took me to Bill’s door in 2010. At that time, it felt like my world was falling apart because my CTO cofounder stole money and had disappeared; leaving me and my other cofounders in a very bad position: no money, the team about to be evicted from our home office in Singapore, and an angry Singaporean fund manager who didn’t want to be blamed for what happened to the National Research Foundation’s first investment from its new high profile venture with Joi Ito and Reid Hoffman. I was concerned because I was being asked to sign documents with names and dates that were not accurate. This especially concerned me because one of those names was Lawrence Lessig, who was sitting on my startup’s Board of Directors1 to my knowledge, this was the first time he sat on a private company’s board of directors. At the time, Lawrence Lessig was the Director for Harvard’s Edmond J. Safra’s Center for Ethics. I was horrified at the idea of signing anything with Professor Lessig’s name on it that was not completely accurate. But I was also being pressured to sign and threats were being made about the legal consequences I would face as a result of my cofounder’s actions. Faced with what felt like impossible choices, I reached out to Bill and asked if he could help me. He said he could and he did. And I’m still reaping the benefits of his kindness more than a decade later.

As part of rebuilding my life in the aftermath of what happened in Singapore, I moved from Asia back to San Francisco to help Yat Siu and David Kim establish Animoca Brands in the United States. I’ll always be grateful to them both for giving me that job and opportunity during a really low point in my life. That opportunity allowed me to build a career in mobile gaming and analytics that I appreciate every single day.

The other thing that was instrumental in rebuilding my life was Bill’s continued support and advice. When I moved back to San Francisco, Bill invited me to a discussion group, Serious Conversations, that would have an outsized impact on my life and on my current passion project, It was at Serious Conversations in 2016 that I first learned about The DAO blockchain project from Steve Omohundro. It was also there that I heard Bill express what I’ll call “Innovator’s Remorse” at what the Internet had become. “The damn Internet” became a phrase I often heard Bill utter when talking about the dumpster fire that social media had become by the time Trump got elected. I think Trump’s use of social media to gain the Presidency really brought home to Bill the dark side of the innovation that he had championed for so long. I met other innovators at Serious Conversations who expressed Innovator’s Remorse, but Bill’s stuck with me the most.

Every innovator is a salesman to some degree. Bill was no different. Bill told me once how he used to sell produce out of the back of a pickup truck or even out of a basket when he was younger in Kentucky. People think of Bill as a great lawyer, and I think he was (although how does one really measure that?). But I think he was also a great salesperson. At his memorial service, I heard some people mention how effective he was in court. I think he had a great ability to “sell” his story and his view to the jury. He would later go on to use the same persuasive power to articulate the benefits of the Internet to a variety of policymakers, regulators, judges and other important people. In his later years, during Serious Conversations, I heard him express regret at unreservedly championing something that’s had such awful, unintended consequences. I don’t think Bill and other proponents of the Internet reckoned with the dismal state of public education, the decline of civility and common norms and the desire of bad actors to exploit the vulnerability brought by connectivity in furtherance of their various criminal acts or clandestine state activities.

One specific flaw of the network that Bill focused on, and one that directly impacts my work on, is the costless nature of publishing information on social media and the Internet. Prior to the Internet, distribution of information or media had a cost. With that cost reduced to zero, the information marketplace that Bill and other Internet pioneers had imagined, turned into the worst sort of public commons: polluted, dangerous, overcrowded and hostile to civil discourse. If USPS had to deliver mail to your house for free for anyone who put your address on an item, can you imagine what your mailbox and doorstep would look like? Yet, this is the state of our inbox and our timelines and feeds today. The costs of publishing bad information or propaganda are close to zero so our information marketplace is being looted and abused by bad actors. Perhaps I am guilty of hindsight bias but I don’t think the market incentives supported the publishing of bad information in quite the same way when online usage was metered in the early days of Compuserve, AOL, Prodigy, independent BBSs and other online communities.

These historical precedents are one of the reasons why I want to try building a decentralized “Twitter” on the blockchain. Publishing on the blockchain has a cost. Currently, it costs less than 1 cent (x<US$0.0001) to post on Creating a publishing cost, however small, may not be the magical panacea but I think it is important to try different things if we want different results. The important thing for is to ensure a user gets enough value from the site, community and technology that they will want to pay that fractional cost to post and share information on I believe we can do this, especially as more people recognize the value of decentralized social media and the need to support it to create a viable alternative to centralized social media.

There are other aspects of, less related to a specific concern of Bill’s, that I believe also have the potential to improve social media and create this additional user value:

Information cannot be erased once written to the blockchain (this makes censorship difficult and it ensures that information stays available for fact checking and other verification);

Use of Creative Commons and ISCN in machine readable format (to empower usage, verify ownership, enable interoperability and allow for AI/automated processing),

Ownership of content (so creators can sell their work or share in the advertising proceeds via smart contract on the blockchain); and

Decentralized content management by the users.2 Jonathan Zittrain discusses this topic in his recent Atlantic article. There, he outlines some approaches Facebook and other centralized social media platforms might take to decentralize their content management, However, to me, that’s like pushing a lion to become vegetarian:  these social media platforms are centralized in architecture, design and management.  The idea that you can graft a decentralized process, that relies on a culture and community supportive of decentralization onto organizations architected to concentrate power around itself and its CEO, does not take adequate account of history and human behavior.

All of these are less directly related to one of Bill’s specific complaints but they all try to drive outcomes that I know mattered to him: democracy and freedom of speech; fairness for the little guy; accurate information; and a productive discourse and exchange of views. I will discuss these other aspects of in more detail in future posts.

More generally, the fact that I am working on and not at a digital advertising company right now is due to Bill and the impact of his recent death. When someone you care about and admire passes away, it can prompt a period of serious self-reflection. When Bill passed away, I became determined to try and use the skills and lessons he taught me in a way that I thought would make him feel like the time he invested in me was worthwhile. I didn’t feel like that working in mobile advertising, which these days seems all about tracking users who have asked not to be tracked. This is why I was so happy when the opportunity came along to work on

I will talk about it more in future installments of the #depubdiaries, but was developed out of necessity because a very important, pro-democracy newspaper, The Apple Daily, was shut down in Hong Kong. Hong Kong is the canary in the coal mine for our Western freedom of press and expression. When I was living in Hong Kong from 2006-2010, it felt like one of the freest places on earth; how horrifying to see it turned into something opposite within a few short years. We should all take note of how quickly the frameworks of freedom can be torn down when centralized. Of course, it will seem hypothetical and far fetched to think our freedom of press and expression here in the United States will be taken away…until it is too late. We must engage in vigorous experiments to defend and bolster these freedoms because equally vigorous experiments are under way to take these freedoms from us, whether by design or as an unintended consequence of the various machinations of the 1% for profit and power.

I’d like to think of as Bill’s bridge to the blockchain. He was an integral part of the computer revolution that transformed our society from the late 70s to today. In fact, I think you can replace Kevin Bacon with Bill Fenwick and reach every innovator in the past 150 years and for the next 150 years within 7 degrees. Although Bill Fenwick passed before was launched, I would like to think that this connection to the blockchain will be one that will make him proud. I will try my best to make it so.

I spoke at Bill’s memorial service on December 10, 2021 and my written remembrance of him is below. This article will be published to the blockchain through the LikeCoin WordPress plugin and I would like for that remembrance to accompany this blog post on the blockchain forever.

Thanks for everything, Bill. I will always remember your kindness and pay it forward 🙏

Spoken at Bill Fenwick’s Memorial on December 10, 2021

Bill taught me so much. Much of what is good in my life I attribute to the lessons he taught me. As his student, as we remember him today and honor his memory, I would like to reflect on the most important things that Bill taught me.

I have seen the value of these lessons by implementing them in my own life and seeing the results. Some of these are pretty verbatim and you might hear the echoes of Bill. Others are things he taught me in many ways, with many different words, so I’m paraphrasing and summarizing.

In the end, Bill did not place his faith in innovation or the law despite spending much of his life engaged in technology and legal innovation. Instead, he placed his faith in kindness as the only way to create meaningful change. So be kind, be helpful when you see the need;

We’re not going to innovate our way out of our problems;

Being part of a community, especially if you want to be a leader, means being willing to do the grunt work if you see that there is something that needs to be done;

Make an extra effort to acknowledge those who might otherwise be ignored. Treat everyone as a real person;

Everyone has a bad day. Extend the benefit of the doubt;

Friendship is not about exchanging gifts; friendship is the gift itself. Bill tried to be very intentional about the help he provided. I think sometimes that confused people who expected him to throw money at their problems. Bill was a teacher at heart and he really felt like you hurt a person’s ability to be independent if you helped them in the wrong way;

Look for community and once you find it, be an active and engaged member of the community;

Don’t be a slave to perception but be aware of how things are perceived because perception shapes a person’s reality;

Have an open mind. Be open to being wrong. Intelligence is most often not about biological capability but more about mindset. It’s hard to learn if you think you already know. Stay curious. Continue to evolve;

Be realistic. Don’t be a sucker; and

Don’t buy bagged popcorn.3 One of the times I remember seeing Bill at his most indignant is when someone brought bagged popcorn as a snack. He was offended at the high markup and thought it was a very foolish thing to spend money on. To this day, I cannot bring myself to buy bagged popcorn because of his reaction 🤣

I always got the sense that Bill would get a bit self-conscious when people talked about his great professional accomplishments. That’s why I would like to make sure we remember him for his kindness. I don’t think he would mind that at all. Let’s all try to honor his memory by being kind to our fellow human beings, even the ones who vote for the other party and all that entails these days. Thank you.

Want to get started with

Watch these community-created instruction videos for and take back ownership of your social media today.

We have a Twitter integration so all your tweets will be backed up to the blockchain forever! 🥳

Video 1; Video 2

(the young are the future of web3)

2 responses to “From Apple to Bill Fenwick’s impact on my life”

  1. This was a wonderful read Henry, thank you. I miss Bill and think of him often.

  2. Henry, I was immensely happy that you were able to attend Bill’s memorial, and contribute so beautifully to the event by sharing your memories of his impact on you, and your life and career. It’s very settling to see you add to those stories here, bringing memories of Bill’s measured grace and caring ways – thank you.

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