A Chat With Dr. Jonathan Reichental, Best-Selling Author, and Former Chief Information Officer of Palo Alto
A Chat With Dr. Jonathan Reichental, Best-Selling Author, and Former Chief Information Officer of Palo Alto
Smart cities, astronomy, open data, and what's on his home screen. (20 min read)
Homescreens is a publication about how we interact with our most intimate possession, our phones. Each week I interview founders and creators across industries, and we reflect on the apps they use, how they’re organized, and their philosophy on notifications and mindfulness. Check out the end of the interview for a full recap and links to all the apps and media discussed.
Dr. Jonathan Reichental has been helping organizations leverage technology to solve complex business problems for almost 30 years. He is formerly the Chief Information Officer for the City of Palo Alto and now serves as the CEO of Human Future, a global technology consultancy, advisory, and education firm. In 2017, he was named one of the top 100 CIOs in the world, and in 2016 one of the top 20 most influential CIOs in the United States.
Jonathan is also a popular blogger, podcaster, and writer, and recently published his newest book, Smart Cities for Dummies, and its iconic yellow binding can be found online and in most bookstores. Let’s meet Jonathan, learn about the CIO role, pick his brain on smart cities, and of course find out what’s on his home screen. What follows is our interview, edited for length and clarity.
Jason: I don’t even know where to start. You’re an author, former CIO for Palo Alto, professor, and now you're the founder and CEO of Human Future. Walk me through some of your highlights and what led you to become the CIO of one of the biggest tech hubs in the country. I’ll hand the mic over to you!
Jonathan: I'm a tech guy all the way. I was programming when I was, I think, 11 or 12 years old, and part of it was because of my older brother, who brought a Commodore 64 home. I remember using the mouse for the very first time, using Paint on the Macintosh, and being absolutely blown away, spending hours doing it, I was hooked! My passion has stayed ever since.
It's a case of looking up to your older brother. I loved it as a ten-year-old standing behind him, as he's programming, about seven years older than me. It's funny, it's just like a language when you're a kid, you pick it up so fast, you know. I knew my for loops, and my if statements, and everything pretty good as a 12-year-old. And then, I wrote my first program.
Jason: What was that?
Jonathan: Do you remember — it still sells, there's a form of it today — do you remember Speak and Spell?
Jason: Yeah, absolutely!
Jonathan: It was the first, and I'll say it in really liberal quotes, “artificial intelligence device,” you know? It gives you words, and it gets harder as you get better and stuff. Anyway, I wrote the version for the Commodore 64, and I sold it in Europe (I'm an immigrant). And so I was hooked! I made, I think, about $150 for it. I always tell people: there was a kid, I think he was 13 or 14, that wrote some software a few years ago. Yahoo bought it for well over $10 million. And back in the 80s, I got $150 [laughs], it's all about place and time, right? And while I had other interests: I'm a musician, I can fly planes and things, the underlying trend was my interest in technology; particularly, I love making and building things, which is probably what gets you excited as well.
Anyway, I grew up in Ireland, where all this happened, and then I had a chance in my 20s to come to the United States to get a Green Card, and I went to work for Coopers and Lybrand as an IT Field Services guy. I grew pretty quick through the organization and stayed there for 15 years. My last job with them was incredible, I was the Director of Technology and Innovation for the firm, and it was focused on evaluating new technologies. As people got to know me, they started to bring me out to clients. So I would go out with an engagement team to Disney, or Lockheed Martin, or Mars, or any number of big corporations in America.
And then about 2007-2008, of course, the recession hit. And one of the things that PricewaterhouseCoopers [“PwC”] wanted to do was outsource all of it. And I was thinking to myself, you know, that doesn't sound like a lot of fun! I don't think my job was at risk; being the Director of Technology and Innovation wasn't really an outsourceable job, but they were offering packages to leave, and I decided this was my chance. I said — you know what, I should use this opportunity to take a nice package and pursue my next thing. And I became the CIO with O'Reilly Media, working for Tim O'Reilly over in Sebastopol in Northern California.
I went from a firm of globally over 100,000 people to sort of a family business with barely 300 people. And that was a culture shock — I'm telling you frickin culture shock. But it was fun. I made some good friends there who I still talk to today.
Then I got this call from a headhunter. I was about a year and a half or so into my work with O'Reilly Media, and this headhunter called me and said they've been keeping an eye on me, and they thought I could make a good CIO for a city. And I said, which city? “Palo Alto.” And I said — that's interesting, the birthplace of Silicon Valley, right? So, I did some interviews and met the city manager, and I took the opportunity. It was a weird next step for me because, while I was interested in government and cities, I never imagined myself working in it. There was this huge curiosity about what's it like to work in government, number one. But number two is, how does a city work? Who looks after the traffic signals, the water systems, and how does the power get distributed? You know, as a technology guy, it was fascinating to me. A city is really like 10, or 20, or 30, businesses — a city is not one business, like Salesforce or Microsoft.
I really got into the depth of this world, and it's often said, you join a business or an organization with the intent to make an impact on it. And certainly, we changed the city, but what was really interesting is, it really changed me. I found out a lot about myself, who I am, and what I love. I fell in love with cities, and I got this real passion for the future of our cities. When I joined in 2011, I said, “I want to make Palo Alto the number one digital city in America.” We weren't using the term “Smart City” really that much; the term at the time was “Digital City.” People were like — yeah, whatever, Jonathan — you're just talking, you don't know anything. Honestly, within two years, Government Technology Magazine, and the Center for Digital Innovation out of Sacramento, named the city of Palo Alto the number one digital city in America. People were absolutely blown away. So yeah, I’m very proud of my team and my colleagues.
And, people wanted to know, what did you do? How are you doing it? So I got all these invitations to speak at events and started to be invited all around the world. I spoke at the Ministry of Finance in Paris, spoke in many places in China, Australia, and South America. Then, I started getting asked to speak and consult with leaders in the Middle East in Dubai, and Abu Dhabi, and Qatar. I really built this love and this passion. Finally, in my fifth or sixth year in the city, I said, — I probably should do this full time, or this is taking over my life. So I started my exit plan from the city of Palo Alto, and the city manager was leaving after 35 years, and I said, that's a good time for me. So in December 2018, I left the city at the same time as he retired.
Then I had all sorts of options: I could have gone into academia because I was also teaching, I could have gone to another city, I even could have gone to a tech company — Oracle was courting me and made me a formal offer to be one of their senior execs around smart cities. But, something was gnawing at me — maybe this is the chance to try my own thing. So in January of 2019, I said — I'm still young enough, still got energy and interest, let me go ahead and try my own thing. So I started this boutique firm called Human Future. And it's focused on three areas: education, consulting (traditional government consulting), and the third one is I set up an investment portfolio, investing my expertise and time, and I get some equity. Right now, I have 11 social impact companies that I'm involved in various stages, and that takes me to today.
If you were to ask me, what's the thread in all of this? Well, there's two. Clearly, I'm a technology guy. I love the era in which we live right now, the fourth industrial revolution, digitalization, artificial intelligence, pretty incredible time to be alive. But the other one is education. Education is at the core of who I am, and I love helping people be successful, and I love taking people on the learning journey. Those are the two items that are sort of the connective tissue of who I am.
Jason: That's an incredible journey. In your first two years in Palo Alto, what kind of accomplishments did you guys have?
Jonathan: We had a pretty progressive cloud-first, mobile-first strategy. And I have to tell you, back in 2011-2012, this was pretty novel. Governments were not even talking about the cloud. Even social media wasn't something that governments were using, it was really Barack Obama, who demonstrated that you could use social media for political purposes, and it actually could be useful for government. After that, we started to adopt this idea of cloud-first. We did the statistics at the time, and something like 90% of people had a smartphone. Up until I arrived, if you wanted to interact with the city, you had to go to City Hall and fill out some paperwork. This was all pretty new for the city to think about: online services and apps and digitizing things.
And then I think the third component was, I introduced the idea that data was an untapped resource for the city. We had a data strategy to do something called Open Data by Default, which means that any data that we would collect we'd make immediately available to the community. The status quo was if you want data or information from a city, you have to request it. And in fact, cities were so bad at it that we had to create laws at the federal level. We created the Freedom of Information Act, which requires the government to give away information that they store. And in California, we have a deeper one called The California Public Records Act, which requires that any public data is made available to anyone who wants it. If you had a reason to see my email, which technically is a public record, you could say, “I want to see Jonathan's email for all the past year, please send it to me,” and the city would be required to either send it within five days or at a minimum give an update within five days. And so my logic was, let's not have people ask for it, let's just make it available. And today, there's an open data global movement.
So in order to support our open data strategy, we created a Data Portal by which people could request data. We upgraded our websites to have a lot of digital services; you could do things like report crime report issues, potholes or graffiti, or trash on the ground. As time went by, we had an increased amount of apps and digital services, and by the time I left, I think we had in the region about 90 different digital services you could do in a small city like Palo Alto. When we created a new 911 system, we did it with two other cities with Mountain View and Los Altos. We shared the coast, and then we were able to actually do things like, and this is a sort of a cliche example: if the police were chasing the bad guy in one jurisdiction, and they went over the border, the information could be transferred to the other police department, and they could continue to chase.
We converted all our analog traffic signals into digital traffic signals. So rather than being lights on electrical circuits, every light became a node on the internet. So you can basically control every single state of every light in the community, and this is cool for doing things like optimization, monitoring your traffic load, and all sorts of cool things like that. But we went further, we were one of the first cities in the country to implement a dynamic traffic signaling system, which means it has cameras on it that detects traffic volume in real-time and adjusts the schedule of the lights according to the amount of traffic.
Jason: That makes perfect sense, and that last point is super interesting, how the traffic signals can respond to fluctuations in traffic. Down the line, do you see that interfacing with autonomous vehicles, where it can divert a vehicle down a lower traffic area? What's the future look like from your perspective?
Jonathan: Well, the future of transportation is autonomous vehicles: cars and trucks, all being completely driven by artificial intelligence. Everything we do now is just a stepping stone; it’s transitional. It's just doing something that's going to help us in the short term, but that's not the long term game. You might think it's the city's responsibility to make it easier for vehicles to know which are more optimized paths to drive, but it's been companies like Google and Apple that have really helped people find better pathways. And the role of the city, in that case, is to become a data provider essentially. I think you have incremental steps, you have this dynamic traffic signaling system, but the long game is autonomous vehicles, and all of this doesn't matter because the cars will figure it out; they'll negotiate amongst each other, and they'll figure out the best path to optimize traffic.
Jason: Very interesting! I want to jump into your phone now, and the first thing I noticed is your background of Jupiter. I don't know if I am thinking too much into this, but what was your thought making this your background? I'm a little bit of a history buff, especially with ancient Roman history, and Jupiter personified the Roman state, where they would swear oaths to Jupiter.
Jonathan: No, I mean, there's something to it, but it's not quite as awesome as your description. First of all, I love astronomy, I love physics, and science. These are topics that are just very appealing to me. I am fascinated by the universe, by existence and consciousness. If you look out beyond the solar system, you get into the galaxy level, and things become really wacky. But just in our own solar system, you know, we have these cool planets: Saturn and Jupiter are these massive, Jovian places, largely made up of gases with a rock solid center. Their scale just is mind-blowing. It's beautiful. And I have to say, a few years ago when I dabbled a little bit in astronomy myself, I bought my own telescope, and you can see the moon, you see the craters, friggin awesome! You see red colors of iron on Mars, and you can see the rings of Saturn with your own eyes in real-time. And then you see the red spot on Jupiter, and you're like — I can't believe I'm looking at this in real-time. It's just absolutely spectacular. So I think the nature of the image is its beauty and represents my deep interests and how I think about my role and what it means to be human and conscious. We're lucky to be a part of this.
Jason: Absolutely. I love that explanation. Tell me about Scannable. What’s your workflow look like?
Jonathan: One of the things I will say about Scannable is, you click the icon, and it starts scanning. There's no menu or anything. It’s really one of the simplest apps I've ever seen. And, you know, if you're not careful, it'll scan whatever your phone was pointing at immediately. I come from a time when we used to have big scanning machines, we used to have fax machines, and if you wanted to send a person a signed document, you either fax it, or you have to run it through a scanner. Today, I'm a big user of DocuSign, but for pure speed, if you have a document that you want to get to somebody with markups or with a signature, Scannable is hard to beat. And, it's really hard to beat free, there's no advertising, I didn't even know what their business model is. It's a high-end scanning application. It sharpens the text, and it whitens the background. I've taken pictures of pretty crappy forms, and the PDF that it creates is better than the original form! I use it every day for contracts for applications, tax forms, so for me, it’s a go-to app.
Jason: That's cool. I’ll check that out. Right next to that, we have Knowable, which is the first time I've seen this app. It looks like a cross between audiobooks and something like MasterClass or Coursera, correct me if I'm wrong.
Jonathan: One hundred percent. It is a cross between Audible and MasterClass. Knowable is only about a year-old startup. It was started by a couple of serial entrepreneurs who have already been very successful. They wanted to create a high-quality learning platform for audio. Not podcasting, and not video like MasterClass, but right in the center, where you could be out for a jog or in the gym and learn something just by listening to somebody. So, the idea obviously has resonated, and they got a huge VC investment, they made TechCrunch news, and it was a pretty high profile story of how these two serial entrepreneurs yet again, hit the jackpot with at least the VC cash.
They were trying to assemble in the first few months, a group of educators who would be interesting to launch the platform with, and I was asked to be one of those first educators. And so I said — yeah, let's give it a shot! So I have one flagship course there called Ace the Next Revolution, and it's about an hour and a half audio course on the nature of the fourth industrial revolution. Every time somebody downloads it, I get paid. Coincidentally, they are moving to a subscription model, starting I think November 1st, so rather than each author getting paid for every download, you'll get a percentage based on people's listening habits on the platform.
Jason: Ah, so like a Spotify or Apple Music deal?
Jonathan: Yeah, very much. Like, I'm very active on LinkedIn Learning, and the way it works is, people or your enterprise can sign up for $29 a month, and you every time people watch my course, I get a royalty. It's an interesting formula based on the overall number of participants and ecosystem, so I'll see how Knowable goes. That's the reason I have the app.
Jason: I just poked around with it for a little bit before we hopped on this call, and I saw courses with everything from nutrition and mindfulness to launching a startup. I even saw Alexis Ohanian was there — looks pretty cool. The first thing that stood out was that it's audio first, which I'm a big fan of. I can't think of another platform that's operating in that space. I'll keep my eye on that for sure. Do you listen to any audiobooks or podcasts yourself?
Jonathan: I'm a very big podcast listener. One of the reasons is because I try to get a 30 minute to one hour walk every single day, and some days I'm happy to just listen to the birds and take in the quietness, but other days I want to learn something, or I want to be inspired, or even laugh.
Star Talk is one that you know, it's very relevant to your question earlier about the Jupiter image. Star Talk is Neil deGrasse Tyson, a pretty well-known astrophysicist; he's super bright and knowledgeable, and the other co-host is a comedian, they kind of play off each other. I like that. I also like Hidden Brain, from NPR, love Radiolab, I don't know if you know that one?
Jason: I always see that podcast recommended, and other people mentioned it, but I haven't listened to it myself. What's the premise?
Jonathan: It's two guys, both are really curious. One of them is a young fellow, and one is a sort of a very distinguished, longtime radio guy, but they're both very, very accomplished. And they take a question. Like, “What happened before the Big Bang?” And they just talk to people and find people who research this topic. They're really quirky and funny. I think what drew me to them very early on is they’re called Radiolab, right? So it's like a radio laboratory, and they actually play with sound a lot. If you're listening with headphones, they use a lot of stereo effects, and they use very interesting editing. It's very unusual how they actually edit and produce the show.
Jason: I like that kind of thing. Have you listened to Twenty Thousand Hertz? They talk about a range of different topics related to sound, and they also have very interesting edits. Check that one out, it's pretty interesting.
Jonathan: I'll check that out. I'll give you a quick few others here: Here's the Thing with Alec Baldwin, it's a very old school, fireside chat. Alex Baldwin will interview Woody Allen or whoever; there’s a bit of a Hollywood slant to it. I listen to Recode Decode with that Kara Swisher, she's good, she's probing. And the final one I would share is my own, called Drinking Wine Talking Tech. What’s it about? It’s about drinking wine and fucking tech! [laughs] Myself and my colleague Tom O'Malley, every week we interview somebody, and we'll have a topic. So if we want to talk about blockchain, we'll bring on someone who's good at blockchain. If we want artificial intelligence, we'll bring somebody on. We do it in seasons. It’s hard work to make good quality, you've got to put some time into it, so we produce a pretty good quality podcast. We'll probably do season five starting in January. We did it for fun, and it's actually really popular. The subheading is “From the front seat of Silicon Valley” because we're giving a perspective of Silicon Valley from our perspectives and people love that. Our biggest audience is the U.S., but our second biggest audience has often been in Japan.
Jason: Really? Very cool, I'll definitely have to check it out. You have Skype on your home screen. Is that for the podcast? I don't see Skype very often anymore.
Jonathan: Yeah, they did upgrade recently, but eventually, Microsoft's roadmap is to merge it with Teams. Skype enterprise is being replaced by Teams, but there's still a pretty big following of Skype on the consumer side. And that takes me to why I have it on my screen, it's because my father lives in Ireland, and he is a Skype user. We can have free calls over video, so I really have only one user, which is my dad. And we are pretty much moving away from it because now we use WhatsApp, which is the standard now basically for calls and videos. It's probably gonna disappear from my home screen pretty soon. I mean, I do my podcast using Anchor, it's a completely different application.
Jason: What's your experience with Anchor?
Jonathan: There are a few reasons why Anchor is kind of interesting. First of all, Anchor is completely free; there is no catch, there is no small print. They sell if you want to advertise, they will bring you sponsors, and they will take a little commission off the sponsorship, so it's convenient. If you don't want sponsors, you can use the platform entirely for free, there's no upper limit on file size or limited number of episodes. But the real winner is because I actually don't record in Anchor. Other people record in Anchor, but I record in Audacity, and then I just import the audio files into Anchor. What I love about Anchor is how easy it is to distribute your podcast to every premium platform almost instantly. All you gotta do is dump your file, hit publish, and boom, it's on all these platforms. So if you were thinking about a podcast version of this, Anchor would be perfect for you.
Jason: Are there any other apps that we didn't talk about that you want to highlight tucked away on different screens?
Jonathan: I'm not a big user of apps like I don't have a lot, I live kind of on the home screen here. Google Photos is awesome. I've been in the IT industry for 30 years and to think about where we've come to an idea like that. First of all, it’s technically free. Secondly, unlimited in terms of the number of photographs, you can technically upload 50 terabytes. I love taking photographs, I’m an amateur photographer, and I just love the fact that I don't have to ever worry about where my photographs are or if they're being backed up
I have a currency converter called XE, and it's friggin awesome, just for easily converting any currency to any currency.
I guess the last one I'll share with you is Kaiser Permanente. That's my health care provider, and now, because of the pandemic, my complete interaction with my medical system is by app. I see my doctor on my phone, I get my prescriptions over my phone and I look at test results.
Jason: It's incredible how quickly they were able to transition to telemedicine when we were forced. Jonathan, I thoroughly enjoyed this, and I really appreciate your time. I had a ton of fun!
Jonathan: I really appreciate this. It's a lot of fun. I think I think you're onto an interesting idea that will probably build a nice following over the next few years.
Endnote
Thanks for reading my interview with Jonathan. You can find him on Twitter at @Reichental and if the future of cities is intriguing to you, pick up a copy of his new book Smart Cities for Dummies here.
Lastly, if you enjoyed this interview, consider sharing it with someone and subscribing if you haven’t already. New interviews are published every Friday morning. If you have an interesting story to tell and home screen to show off, submit a request at www.homescreens.co.
📱 App, Product, & Media Recap
🦋 Evernote Scannable - Scan contracts, receipts, business cards, and any paper that comes your way. Save or share documents instantly and move on.
🔊 Knowable - Audio Courses - Knowable is a growing library of audio courses led by the world's most trusted experts.
⭐️ StarTalk - The StarTalk podcast network bridges the intersection between science, pop culture and comedy with clarity, humor and passion.
🧠 Hidden Brain - Shankar Vedantam uses science and storytelling to reveal the unconscious patterns that drive human behavior
📻 Radiolab - The show is known for its deep-dive journalism and innovative sound design.
🎤 Here's The Thing with Alec Baldwin - Alec Baldwin takes listeners into the lives of artists, policy makers and performers.
🍷 Drinking Wine Talking Tech - Dr. Jonathan Reichental and Tom O'Malley drink wine and discuss emerging technologies from their front seat in Palo Alto, California
⚓️ Anchor - Anchor is the easiest way to make a podcast, brought to you by Spotify.
💲 XE Currency Converter - from rates to charts to global money transfers, XE puts all your currency needs into one app!