I love the Pomodoro Technique

The pomodoro method is startlingly simple 

About 18 months ago when I started working on my own, I learned about the pomodoro method.

Its is startling in simplicity. You can say it in a sentence:

Set a timer for 25 minutes to do a task or set of related tasks, then set a time for 5 minutes to take a break. 

Like so many things that sound simple, it quickly gets nuanced. Golf? Just hit the  ball into a hole. Profit? Just sell for more than it costs. Bitcoin? It is just an encrypted distributed ledger that solves the double spend problem of digital currency. Ok, ok, so some things just start out complex.

For the pomodoro method, some of the nuance is how you spend the breaks. I find the best days are when I basically stop working when the timer goes off. I struggle with how to incorporate the technique when I have lots of meetings, travel time, or many tasks scheduled. The classical approach calls for 15 minute breaks every three pomodoros, but I rarely do that. I’d like to incorporate it on days when I have continuous deep work.

Why I love this technique:

  1. It forces some accountability about the time I spend on things. Those 25 minutes are pretty small but long enough to be productive in deeper work, and it is amazing how quickly my internet-enhanced-ADHD monkey mind jumps off task. The ticking timer is the reminder: Oh yeah, I set out to do something.
  2. I get better at estimating time for tasks. Email in 1 hour? Sure. Easy. Then I measure the pomodoros. Yikes! Four pomodoros! Some days it takes six when I think it will take one. At least I know where my time goes.
  3. I love the breaks. The idea for breaks is: do anything but work. Walk, exercise, daydream, stare out the window like a spring-struck teenager… anything to allow the mind to be free of the intensity of the deep work. Before, I would castigate myself for taking too many breaks. Gotta be maximally productive! But I find days with pomodoros are more productive in doing the things that matter. And I feel better and more accomplished at the end of the day. I’m pretty sure the breaks are the reason why. They allow me to refresh and reset deeper intentions.

Pomodoros are a great foundation for productivity. They are also a great habit to improve the satisfaction of your day and week. I’m happy I found them and incorporated them into my daily life. 

Top 5 Tech Surprises in 2017 … and 2018

I like to reflect on what surprised us most over the year. It helps me understand conventional wisdom and the surprises that upset it… helpful if you want to defy conventional wisdom and be all disrupty & stuff.

1. Bitcoin Bites Back

Conventional wisdom last year: Blockchain is important but cryptocurrencies like bitcoin, not so much. Banks and other institutions will be the first to deploy blockchain technology.

Conventional wisdom now: What the hell just happened? Should I buy bitcoin or short it? This is like the dotcom bubble!

What happened: Bitcoin, Etherium and other cryptocurrencies had a run up in value like nothing we’ve ever seen. It makes the dotcom bubble of the 90s look quaint. Most notable so far is block.one, a blockchain startup that has raised $700 million and plans to continue to raise over $1 billion. The company has a beta product, consists of about 50 people in a distributed team that formed over the last 18 months. Unlike traditional startups, block.one didn’t sell equity shares in the company. They sold a cryptocurrency, called EOS, in an initial coin offering (ICO). By one estimate there were 1,500 ICOs in 2017. The total value of cryptocurrencies including bitcoin is worth over 30 times the value in January of 2017.

Oh, and the banks and other established companies? Turns out — surprise! — that big companies have already dealt with the problems blockchains solve. To be a good candidate to use blockchain you need to have a problem that requires of immutability of data, distributed operations, and lower transaction costs or coordination costs. If you don’t need all three, you probably don’t need blockchain. This new world will be built by startups, not banks. Right now, startups are racing to build the infrastructure to allow even more startups to build apps on blockchains.

Surprise in 2018? Conventional wisdom is looking to the 1990s dotcom playbook. A crash or further mania will be met with a chorus of “I told you so!” The biggest surprise would be price stability. It would be mind bending if the most popular cryptocurrency next year was a reliable, stably priced cryptocurrency, avoiding the dotcom bubble trap. A really easy to use, consumer-friendly version of a cryptocurrency would also be a surprise. Imagine cryptokitties but useful and easy. Another surprise could be a vulnerability in bitcoin or a quantum computer breakthrough that makes blockchains more vulnerable.

All hard to imagine in 2018, but not impossible.

2. 126 million Americans — Really?

Conventional wisdom last year: Facebook, Twitter and internet media are powerful political media. The Russians were involved in the DNC email hack. The two facts aren’t very connected and if are, it’s in an incidental way.

Conventional wisdom today: The Russians swung the election against Clinton and it might have been the decisive blow. They used social media, fake news, and hacking to do it.

What happened: When I first heard the Russians spent a few hundred thousand on Facebook ads, I admit I shrugged. Yes, it shouldn’t have happened, but it was a tiny amount in the grand scheme of things. Then came the revelations that as many as 126 million Americans were exposed to the ads and their viral effects — surely one of the most cost-effective ad spends ever.

We realized last year that our democracy & cohesion of our nation is at risk from the structure of the new media. Its not just about fake news. Its not just about cybersecurity. Our new tools can literally help tear our nation apart. 2017 was like a slow motion 9–11, realizing how some evil bastards used our own technology against us.

Surprise in 2018? It is possible the involvement of Russia goes much deeper than we know. Investigation by the FBI and Congress will reveal a lot this year and it could have surprises for how internet media is used to manipulate us. Also, this conversation goes beyond the Russians to our relationship with internet media. What if Facebook is right and the answer is more media engagement, not less?

3. #MeToo and Women’s Cultural Moment

Conventional wisdom last year: Silicon valley culture is mostly a meritocracy. We’re not really sure why women CEOs don’t get funded as much — maybe it’s their fault.

Conventional wisdom now: Silicon valley is mostly a meritocracy if you are a twenty-something male engineer — even better if you wear a hoodie and look like Zuck. If you’re female … wait, shit, were you hit on by VCs? We gotta do something about this!

What happened: In mid 2017 we were surprised that some slimeball VCs used their power to harass and assault women seeking funding and jobs. It shocked the industry and exposed the lack of process for vetting sexual harassment. We had a wave of resignations and the shuttering of at least one VC fund.

Just months later, similar allegations emerged in Hollywood and politics, but with much, much higher profile. We were reminded that, despite the rise of internet media (see #2 above), our culture still depends more on mass media created by Hollywood and politicians. They were the ones that created the awareness that generated a public groundswell demanding resignations and real change.

Surprise in 2018? I know its cynical, but a surprise would be real, meaningful, structural reform among venture capitalists. I fear that, like past cultural moments for women (remember Anita Hill and the year of the woman?), there will be serious backsliding in 2018. There doesn’t seem to be any organization behind #metoo and it will likely wither like the #occupy movement. We need to keep the pressure up in the tech community to implement changes like those suggested by Reid Hoffman and support SB244. That bill adds “investor” to the list of non-employee relationship with protections against sexual harassment. That list already includes teachers, landlords, lawyers, and social workers. Seems a minor thing to add “investor,” yet this bill has not made much progress since August when it was introduced.

4. Tech Turns Evil

Conventional wisdom last year: The technology industry is the darling of America. We might have some blemishes, but they are growing pains.

Conventional wisdom now: The tech industry is a source of many of the ills of society and the future is even more dire.

What happened: This was a year when the tech industry went from darling to demon. We are, in the darkest view, misogynists and racists who won’t hire or promote anyone who doesn’t look like us; monopolists who need to be muzzled (the Fiercesome Five); scofflaws (Uber, Bitcoin); left-wing overlords controlling the new medium (Facebook, Google, Twitter, Amazon); money-grubbing moguls who sell out our democracy for the sake of a scalable advertising system (Facebook, Twitter); con-artists (cryptocurrencies), and contributing to ills from unemployment, to teen suicide to low sperm count.

Here’s the thing. These criticisms are not all wrong.

As entrepreneurs and engineers we want to solve the problems. Monopolies? Let’s use a new platform like blockchain to tear them down. Screwed up media model that sells us to advertisers? Let’s reform it or remake it. Fake news? Let’s fix it. That’s all fine and good and lets keep doing it.

We also have to come to grips with the scale of impact technology is having on society. We are going to need more than just engineering solutions. Inside the industry, we need cultural change. And the big questions are for society, not just engineers, designers, and business people.

Unfortunately, the folks with levers of power in political society are not our fans. The president and many Republicans have their knives drawn. They might be supportive of being rich, but not for the things that made the tech industry rich in the first place: investment in government research, higher education, open trade, immigration & social diversity, helping small companies with capital (e.g. Small Business Admin role in early venture capital), and open access to networks (breaking up the Bells, net neutrality, local phone access).

Surprise in 2018? I see more opportunity for negative than positive. For all the press this year, it could get worse. What if company executives knew their service was harming people and did nothing or worse, covered it up in the interest of profit? It is what happened in the industries we love to hate: cigarettes, auto, oil, & pharmaceuticals. As bad as it was in 2017, it would be a surprise if we find infotech on that list. But it’s not impossible.

5. Peak Elon?

Conventional wisdom last year: Elon might be a genius, but he’s getting stretched thin with rockets, electric cars, and solar panels.

Conventional wisdom this year: Elon is a genius, but he’s getting stretched thin by rockets, electric cars, solar panels, … AND boring tunnels, hyper loop, trips to mars, and electric semi-trucks.

Elon Musk this year began mass production of an electric automobile and regular use of a rocket with vertical landing of its launch stage. He unveiled a new way to make tunnels, plans an electric semi-truck, and plans for the largest rocket ever conceived to take hundreds of people to Mars. Oh, and didn’t he launch some connect-your-brain-to-the-internet initiative too?

He has shown he can turn fantasies into reality, has received billions in financial backing, and revealed plans that would have made our heads explode five years ago — ok, admit it: the combination made our heads explode even this year. Hence, the reason it is one of the surprises of the year.

Surprise in 2018: It’s hard to imagine a similar combination of surprises in 2018 from Elon. A logical bet would be to say that no human can maintain focus on so many things and we have seen peak Elon this year. But logic wouldn’t have resulted in 2017 either.

Meditation for Slackers

A daily meditation practice is way easier than this!

Meditation for Slackers

I made meditation a daily habit after years of trying & failing. It was easier than I thought once I figured out four key insights.

  1. Redefine success. The media & religious idea of meditation (like the one above) is of something hard to do that brings total bliss. Growing up in a Hindu household in the US, those ideas were ingrained into me. It helped to realize my goal is not nirvana but awareness of my own thoughts, less anxiety and more happiness.
  2. Choose a daily event for the trigger. I had previously tried squeezing meditation into my schedule, only to abandon it when pressed for time. Inspired by tiny habits, I built my meditation habit after brushing my teeth in the morning. Once I committed, it quickly became second nature. What’s right for you? Right after you dress for the day? Yes. When you get home in the evening? Yes. When you get a moment between meetings? No. You want to start your habit based on another daily habit, not based on an idea of “when I get to it.” How about right before you go to bed? No, because you want to chain your meditation habit onto an existing one. Instead of doing it before you go to bed, think of something you do even before going to bed, like reading or brushing your teeth.
  3. Take just ten breaths — or five. I decided to start small. So small it was a bit embarrassing. I wanted something so trivial I could keep it up for at least six weeks. Ten breaths takes only 30–60 seconds or so and anyone can spare 1 minute from their day. Just count your breaths and don’t fight thoughts that enter your mind and re-center on your next breath. Having thoughts invade your mind is part of meditation. It is not the Hollywood and religious image of total lack of thought. (Yes, you may have those moments and it may feel like the photo of a monk in a blissed out state, but don’t worry if you never feel that way.) The magic of meditation is in how it makes you feel, not the images on a web page. Even 30 seconds of meditation is enough to feel better.
  4. Congratulate yourself. My goal in the beginning was to just sit and breath daily for six weeks. Each time I did it, I celebrated by say, “Yes, I did it another day.” Yes, I felt a bit silly taking just ten breaths, but I reminded myself that my goal was to build the habit and worth celebrating every day I did it.

That’s it. Once I took these steps for about six to eight weeks, I got into the habit of meditating for just a minute or so. Since then, I’ve slowly expanded my practice from ten breaths to about 15–20 minutes every day. But when I’m super rushed or even in the middle of other meditation techniques, I find myself coming back to “Just take ten mindful breaths.”

I hope what I learned helps you build your own meditation habit.

The Untold Story of Ridesharing – Part I

February 2017 marks the fifth anniversary of one of the most disruptive inventions ever. Ridesharing went from an idea ahead of its time in 1997, to a crazy idea in 2011, to cars on the streets in 2012. Today Uber, Lyft, and other ridesharing companies around the world like Didi, Grab, and Ola are worth tens of billions of dollars. Ridesharing is on course to overturn the world of automobiles to become the dominant mode of transportation in the world.

In Brad Stone’s book, The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley Are Changing the World, he says, “Ten years ago, the idea of getting into a stranger’s car, or a walking into a stranger’s home, would have seemed bizarre and dangerous, but today it’s as common as ordering a book online.” Sidecar’s story is included as the starting point of ridesharing, but it is important for the full story to be laid out.

Part I: Inspiration

The story started in 1997. I was waiting for my wife to pick me up from Mission Cliffs, a climbing gym in San Francisco. She was late. I was bored,gazing at cars driving by and fiddling with my phone. That was when it struck me. There were people driving around. Why couldn’t I convince one of them to take me home? If only they knew I needed a ride. Some might have even been going my way. Someday, I knew, my phone, messaging, and GPS would come together to make this possible. The buzz in the mobile world at the time was about an FCC mandate to make all mobile phones’ locations accessible to tracking for 911 emergency calls.

It started back before anyone thought it was possible. Back then the Nokia 1610 was popular, Titanic was the big hit … and I had hair.

A few years later, I convinced a friend, Neil Peretz, to help me figure out how to launch a company, which we called “vCar” for “virtual car.” Neil had a diverse background including being a lawyer, working in China, and starting his own company that pioneered email on a phone before Blackberry. “I think phones can replace the need for cars,” I said to him. After two months, though, I declared the project over. There was not a lot of interest in our service from consumers, who seemed content driving in the era of $.99 gasoline. In addition, we realized this idea would mean taking on two slow-moving bureaucracies. One was having to deal with the cell phone carriers to get access to location information. The second was dealing with regulators and politics. We read “Paratransit in America” by Robert Cerveros at UC Berkeley. It described the meteoric rise and fall of jitneys in 1920s America. Jitneys were a transportation innovation crushed by the political power of taxi and transit companies that used their influence to make jitneys illegal.

So I put the idea on the shelf, but figured I should apply for a patent. While I wasn’t sure if they’d be useful in the future, it couldn’t hurt. Plus, it was cool to have another patent. In the meantime, I put transportation behind me. Brightmail was doing well, I had just become a father to twins, and, like the rest of Silicon Valley, I was preoccupied with the aftermath of the disasters of the dot com crash and the 9–11 attacks.

It would take more than a decade before Ridesharing came into being.

Part II: How the “Sharing” got into “Ridesharing”

The Untold Story of Ridesharing — Part II: How the “Sharing” got into “Ridesharing”

Continued from Part I

Fast forward to 2007, I’d had twins, gotten divorced, sold Brightmail and taken the now-traditional, victory-lap sabbatical. I was ready to re-engage in the world of startups. Having children had changed my view of the world. The definition of what mattered was no longer measured by my own lifetime. I could imagine their lives and their children’s lives. Long range concerns like climate change loomed larger and I committed to do what I could to bend the curve of that impending disaster.

I wondered if we could get rid of private cars if we made carsharing more convenient. I had joined the board of City Carshare, a pioneer in the field, and was very familiar with the service. I tried an experiment. I sold my car and tried to just use carsharing, transit and taxis instead. It quickly became a nightmare. It was very hard to get two small kids to school each day. My daughter still remembers the short cut we’d take to the City Carshare location which involved a steep hill through the woods, a path now blocked with a “Danger ” sign. Taxis lacked toddler car seats, if they even bothered showing up. Transit didn’t go everywhere at convenient times. It seemed like owning a car was the way to go, so I gave up my experiment and bought a SUV, a green Toyota Highlander Hybrid.

There had to be another way to have big impact on transportation, I thought. In the era when Tesla was just getting off the ground and not yet run by Elon Musk, I wondered if it was possible to supercharge electrification of automobiles by re-engineering an existing auto company brand. I recruited a team with a plan to take over the luxury carmaker, Jaguar, and turn it into a electric car company. It was a bold, audacious idea. But it was too weird for the venture capital funders and I didn’t have the experience or reputation in the private equity world to raise funds for the idea. Plus, I was learning that electrification of cars was one of the hardest ways to have impact on the climate.

I led a project, The Gigaton Throwdown, to understand how to scale solutions to climate. We found electrifying cars is one of the most expensive ways to impact carbon emissions compared to alternatives like solar, wind, biofuels, and energy efficiency. Informed by that project and frustrated by the lack of support from investors, I killed the electric car company project.

The end of the car project left me thinking the real opportunity was using information technology to create a very scalable, capital efficient way to change transportation. In the summer of 2009, I taught at Singularity University and helped incubate a company to create peer-to-peer carsharing, Getaround. At the end of the summer I offered to invest in the nascent team and join as an executive chairman, but they turned me down, concerned I would exert too much control over their company. Annoyed at being rebuffed, I decided to experiment with P2P carsharing myself. A key obstacle was insurance. Personal insurance didn’t cover renting out your car to someone else and an insurance company could cancel your insurance if you did so.

In an effort to understand the issue, I met Dave Jones, an Assembly member in the California legislature. He asked, “Why don’t you tell me what changes are needed?” I sent him a note with ideas for how to change laws to allow P2P carsharing to exist, but didn’t think anything would come of it. A few weeks later, I got a call from his staffer, “Dave would like to introduce a bill using your ideas.” Wow. I was floored that it could be that easy. I took several trips to Sacramento to lobby and testify. It passed unanimously in both houses, and on September 29, 2010 Arnold Schwarzenegger signed the country’s first P2P carsharing law. It changed insurance rules to allow carsharing as long as an individual didn’t make more than the annual cost of owning or operating their car.

The new law created an important distinction that would become important years later with the invention of ridesharing. The idea of commercial use of a car revolved around making a profit. Prior to this law, thinking about profit referred to the per mile cost of operating a car. For years, the IRS had used a standard number like $.50/mile as an average cost of operating your vehicle — in the case that you didn’t keep receipts of your actual costs. AB1871 said profit would be measured annually, not per mile. A typical car costs about $6,000 to $8,000 per year. AB1871 allowed a car owner to make occasional income off their car without threatening their personal insurance. It was a new way of thinking about “not making a profit.”

I got a law passed that redefined what it means to make a profit from a car … and I learned an important lesson about innovation and the law.

AB1871 taught me an important lesson. Don’t worry so much about the law when you are innovating. I’d put a lot of effort into changing the law before creating and scaling the innovation of P2P carsharing, only to discover I didn’t think the innovation was that hot. I had spent months not just getting that law passed but doing a pilot with City Carshare with my Highlander, ripping out its dashboard to modify its innards to be compatible with City Carshare. It wasn’t a very scalable model and I killed the project. While I first thought insurance was the biggest risk, I learned over those nine months that it was secondary to more basic problems with the model.

The episode also taught me something about my own anger and pride. I held onto the carsharing project in part because I was angry at the Getaround team. Letting go of that project also let me leave the resentment behind. When I closed that door, others opened.

Next, I started working on ideas that would integrate many modes of transportation into one interface. I envisioned taxi, limo, buses, rail, carsharing, and carpooling all available in one integrated interface. It was, in 2011, an early version of what Google and Apple Maps would become. If you are curious, the patent applications we filed back then are still on file at the Patent Office and are publicly available. I still think the integration of various modes into one interface is a good idea. It’s where Google and Apple maps are headed.

The challenge with these sets of ideas was trying to get taxis to adopt new technology. I was wary of having to integrate with the legacy technology of the taxi industry. Integrating with legacy systems is almost always a nightmare and if you can avoid it, you do. I still had nightmares of integrating with legacy modems at FreeLoader and the rats nest of software to integrate with legacy newspaper systems after we were acquired by Individual, Inc. Plus taxis had the problem that they always prefer a street hail over a phone or computer request. The guy flagging on the street is a sure thing and doesn’t require drive time to get there.

I’d been hunting for the right combination to enable the future I saw of smartphones replacing the need to own a car. I hadn’t been able to assemble the pieces to something compelling, but they were about to come together.

Next Part III: The Birth of Sidecar and Ridesharing

The Untold Story of Ridesharing — Part III: The Birth of Sidecar and Ridesharing

Continued from Part II

One of my ongoing frustrations of this era was lack of great software developers to work with on my ideas. I felt the need to iterate with real products, but didn’t have a real software team to partner with. Then I ran across a small company based in Ann Arbor that seemed to have a similar vision of the future.

Jahan Khanna and his partner Adrian Fortino had built an Android based system to predict bus arrivals at the University of Michigan. I flew up to Ann Arbor twice to share my vision of a world where private cars are replaced by smartphone apps. “Let’s join forces,” I pitched to them. I would become CEO, and we would convert Jahan’s company, Shepherd Intelligent Systems, into the new company. By late fall, Jahan was living in San Francisco and had brought several of his fellow UMich developer friends with him.

We committed to trying ideas quickly. Our vision of the future was a shared ride service using smartphones that would route dynamically based on demand. The challenge was the same as all companies with big vision — How do we start and get traction now? Our first idea was to start with a fixed route that required use of a smartphone to order and pay. We called it “38 Air” because it mirrored the popular and overcrowded 38 Express bus that stopped outside our office. We spent a month on it before our lawyers told us it was 100% illegal. (Interestingly, this idea was launched years later by Chariot and other startups. Two things changed in the subsequent years. First, because of the new corporate commuter buses, San Francisco created a system that allowed private buses to pay to access public bus stops. Second, because of Sidecar, Lyft, and Uber, regulators became more open to innovation in transportation.)

Our first idea was inspired by the 38 Geary line.

38Air lasted only weeks. Next we tried a dynamic routed shuttle that a group of friends could coordinate. We envisioned friends going out on the town would use this service to split the cost of a limo. Jahan mocked up simple software and we tried it out with me as the driver in that same Highlander Hybrid. I picked up friends all over the city in route to Chambers, a bar in the Tenderloin. It sort of worked, but it was complicated. Too complicated. Next, we tried coordinating passengers to ride and split the cost of an Uber black car or taxi. That was even more complicated.

By now it was late in 2011 and our seed money was running low. Our first three ideas failed. One of the ideas we had been kicking around was to just allow any person to give rides without a commercial license. Uber required drivers to have licenses (known in California by its acronym, TCP) and that meant only black cars and limos. I’m rich and I thought they were pricey. For the 20 somethings I worked with who had just moved to San Francisco, the Uber price point was impossible. It was reserved for dates and desperate situations. Meanwhile we knew peer-to-peer carsharing was possible. Could something similar be done for rides?

A friend told me about an interesting service, Homobiles. It was car service started by a local queer leader for the LGBTQ community. It operated with no TCP licenses. Instead, volunteers drove their own cars with their own personal insurance. Patrons had to make a request via phone or text and could donate money but it was not required. I took homobiles to the airport for a trip to New York. It cost me $20 for a trip that normally cost $50 in a taxi. Wow. This system was cheaper than taxis, nevermind Uber. Homobiles had been in the press yet hadn’t been shut down. It seemed to be operating in a grey area of regulation by taking donations. We wondered, “Can we create a scalable, technology-enabled version of homobiles that could allow us to then create our shared ride vision?”

There were big challenges. Homobiles operated with no insurance coverage. Taxi and limos were covered for $750,000 to $1 million. They didn’t vet their drivers beyond personal references. And they operated like taxis, with orders coming in over the phone. There was no app, no turn-by-turn directions for drivers, no cash-less transactions, etc.

We thought, what if you could create a system that combined the convenience of Uber with the affordability of Homobiles, and the environmental benefits of carpooling and transit? That is what we set out to do with the first version of Sidecar. We also had to figure out how to operate in a grey area of the law. If we were clearly illegal, we’d get shut down immediately with no defense argument. I was not interested in slogging out a fight with regulators and lawmakers like I did with peer-to-peer carsharing.

So we designed our system with legal constraints in mind. Our payment system was donation based, like carpooling and Homobiles. There was a suggested amount to pay, but riders could dial it up or down. We defined “not making a profit” in the same way as I had for peer-to-peer carsharing — on an annual basis, not mileage. We used the new capabilities of doing electronic background checks on drivers, so they were as secure as San Francisco taxi drivers. We also told drivers we’d cover liability that wasn’t covered by their personal insurance up to $1 million, an arrangement similar to what I’d designed for peer-to-peer carsharing. And, of course, we had electronic payment through credit cards, GPS, and a rating system for drivers. Unlike Uber and taxis, our drivers were not professionals, so we gave them turn by turn directions to navigate the city.

Despite all the preparation, I was nervous that consumers wouldn’t be willing to get into a stranger’s car. On New Year’s Eve Jahan was out at 2am trying to get a ride home. Taxis were nowhere to be seen. Uber’s black car service was ridiculously priced. Desperate to get home, he waved down a guy doing pizza deliveries and convinced him to give him a ride home. It turned out he was delivering close to Jahan’s home anyway. Jahan tipped him $20. He called me the next morning practically yelling, “This is so going to work!”

The original version of Sidecar launched in February of 2012. Not very pretty but it did the job!

We introduced Sidecar in February 2012 and it was an instant hit. Everyone who tried it loved it. The hesitation of getting into a strange car turned out to be just momentary and people took comfort in all the precautions we took, like background checks. Archive.org captured that our website was live on Feb. 7, but I have to admit I don’t remember the exact date. We were so busy, we didn’t capture it ourselves!

The Sidecar vision was to become a multi-passenger, multi-stop ride service driven by everyday people — what eventually became Sidecar Shared Rides, Uberpool, and Lyft Line. In the spirit of getting to a minimum viable product (MVP), however, we stripped out the complexity of multiple passengers and stops. It would take years before we got to the original vision.

I called our invention, “Ridesharing.” It was like carsharing, but for rides, so “Ridesharing.” I liked the name because it was descriptive and aligned with the vision to one day allow strangers to share rides. It was also evocative of the sharing economy, a category that was gaining currency. The naming choice would get the attention of others who were doing carpooling, which was also called “ridesharing.” One carpooling company, Zimride, caught wind of it and quickly copied what we created. They called their version “Lyft.”

About a month later, one of our team overheard two people who he surmised were the founders of Zimride at The Creamery, a cafe in the SOMA neighborhood of San Francisco. It was blocks from Zimride offices. “I can’t believe how much traction Sidecar has,” said one. “I don’t know how we’ll ever catch up with them,” the other one replied. It was one of our first hints that Zimride was planning to compete with us. The very first hint, however, was that within the first weeks of Sidecar’s launch, we saw that Zimride founders and board members were using Sidecar. Curious, I called one of them and got a stammering response to the question, “You guys aren’t thinking of doing this are you?”

Five years after launching, ridesharing has taken over transportation even in small towns like Sonoma, California. I shot this parking space notice in February 2017.

The remaining part of the story has been told many times. Lyft launched with a big fuzzy hot pink mustache on the front of every one of their cars. They captured awareness and soon were growing faster than we were. UberX copied ridesharing, too. They both raised even more money to build on their existing funding advantage. And the rest, as they say, is history. Which is to say, we were history. We tried to make the category less capital intense through innovations and set a blistering pace of innovation that continued to beat Uber and Lyft, but were unable to overcome their money advantages to recruit drivers and riders. Today ridesharing famously remains one of the most capital hungry private investment categories.

Part IV: Silicon Valley’s Attitude Toward Patents

The Untold Story of Ridesharing — Part IV: Silicon Valley’s Attitude Toward Patents

Continued from Part III

When people ask what lessons I’ve learned from Sidecar, there are the obvious ones about competing against well funded companies and the role of marketing. But one factor isn’t widely discussed: Uber and Lyft violated our patent and we couldn’t do a thing about it. A different attitude about patents would have changed the history of the industry.

I didn’t think much of my patent until the late 2000s when I started thinking about transportation again. Patents had become valuable and had impact. At Brightmail I built the company around a key patent that ended up being seminal for email security. While at Brightmail, I didn’t think the patent helped us much. After the sale to Symantec, however, I heard from competitors it served as a barrier, and they spent a lot of time trying to avoid violating it.

In the fall of 2011, I sent notes to Uber executives offering to license our patents. We offered again to Lyft and Uber in 2012. The deal I had in mind would have given us revenue from the licensing and also put their ride service on a more comprehensive service that allowed people to share rides on Uber or Lyft or taxis and also order bus and transit rides. We wanted to create our Shared Ride service and leverage what Uber and Lyft had already created. Combined with access to carsharing and transit, it would replace the need for owning a car. But my vision of a grand deal didn’t last long because I either got cold silence or a “not interested” from both companies. I was flabbergasted. They were just going to walk over the patent and ignore it?

That began a series of efforts to try to figure out whether we could take action against Uber and Lyft. We learned some basic facts about how hard it is to litigate patents, so we put it aside to focus on the business. Then, as they continued to roll out services that infringed more and more on the patent, such as Lyft Line and Uberpool, we would look again. What we learned is that it is really, really hard to enforce patents these days. You have to be a large, well capitalized company with a dedicated legal staff. We got estimates ranging from $6 million to over $10 million to enforce a patent, not to mention the massive distraction of depositions, and “discovery,” the process of turning over documents related to a lawsuit. There was no way we could afford to sue Lyft or Uber and they knew it. So they just ignored us.

There was another factor. In Silicon Valley, enforcing a patent is seen as somehow uncouth and against the values of innovation. We heard from potential investors, some board members, and members of the startup community sentiment like, “We fight over markets, not over patents.”

Attitudes about patents have changed a lot. Silicon Valley culture is disdainful of patent claims.

Luckily for us, other industries cared more about patents. When we were forced to put the company up for sale in 2015, we realized the patent portfolio might be valuable outside the Silicon ethos. And indeed, in auto, retail, and more traditional industries, potential buyers did look at the patent as valuable. It helped us get to an asset sale to General Motors in January of 2016.

Well, that is the story. Its one that is still unfolding. With autonomous cars the cost of a ride will make ridesharing cheaper than owning a car, even cheaper than transit. The disruptions are going to be massive and widespread, affecting the automobile industry, wages and employment, city planning, real estate, insurance, even organ donation (the major source of healthy organs is, sadly, from auto accidents). It’s amazing to contemplate and I’m proud of my small part in helping it come to life.

(originally published on Medium March 1, 2017)

Top 5 Tech Surprises of 2016…plus predictions for 2017

1.Autonomous vehicles start getting real

The conventional wisdom was that autonomous cars would take a long time to deploy and would be a luxury feature for private car owners. Instead, we saw rapid technology innovation and capitulation to the idea that fleets will first deploy autonomous vehicles. Think ridesharing and freight service.

Tesla, Google, Uber, and auto makers hit major milestones getting to full autonomous vehicles. GM was the most aggressive in realizing it was behind on tech and business model. They overcame their NIH (not invented here) and bought Cruise (autonomous), Sidecar (ridesharing), and invested in Lyft. Otto, an autonomy startup bought by Uber, did the first commercial autonomous freight delivery on a large semi-truck.

In 2017 I see continued advancements in technology and the first commercial passenger trips on fully autonomous vehicles with no driver.

2. Internet media is YUGE!

We knew this would be a big year for internet media because of the election, but wow, what a year. Internet media didn’t just affect the election, it resulted in shots fired in a DC Pizzeria, a Pakistani minister escalated nuclear threats. Facebook admitted it had responsibility to slow the spread of fake news and took first steps to help. The line between manipulation and transparency was tested by Russian hackers and Wilileaks.

In 2017 we will come to terms with the fact that we have to fix internet media. We fixed email spam. We can fix this. If you want to help, let me know.

3. Virtual Reality bites

2016 was supposed to be the big breakout year for VR with the release of many headsets and content. Augmented reality (AR), meanwhile, was supposed to take longer to get to fruition.

Then Pokemon Go happened. Easy to build content (apps) on a cheap widespread hardware platform (smartphones) beat out sophisticated and high resolution content on purpose built expensive hardware (content on VR headsets). We re-learned an old lesson: PC v. mainframe and Mac; Internet v. ISO; VHS v. Betamax; and Android v. iPhone.

In 2017 we will see dedicated VR and AR headsets continue to struggle while apps and AR/VR hardware for smartphones get better and better.

4. Space available

Some ideas have been dreams for decades and two of them became reality in 2016. SpaceX did a successful vertical landing of a rocket, creating a pathway to make space more accessible by reducing the cost of launch. And a small private company, Lunar Express, got the rights to land on the moon, paving the way to a whole new way to explore other things in our solar system.

In 2017 we’ll see Virgin Galactic launch its first space tourists, starting with founder Sir Richard Branson.

5. She is always listening

We entered the year still thinking “privacy is dead.” But some things happened in 2016 that are freaking people out. There was the Russian hacking the Democrats and disclosure of billions of accounts hacked at Yahoo and elsewhere. We also saw that governments have a long reach into our lives. The US government insisted that Apple change its software to allow access to someone’s private phone and Facebook cooperated with the Chinese government to change its software to suit Chinese control. Finally, the Snowden movies (see both the Hollywood version and the documentary if you can), drove home to everyone how vulnerable we are.

During the Apple v. DOJ debate, I kept wondering about my new Alexa device from Amazon. It (she?) is always listening for the command prompt, “Alexa.” If a government could demand that Apple and Facebook change their software for higher levels of surveillance and control, why not ask Amazon or Google to modify their in-home assistants? Well, it is kind of happening in 2016. The first subpoena was issued to Amazon asking for information from an Alexa device. It’s not a request to actively record, but watch for that in the future.

In 2017, with a Nixionian president in office with the powers of the NSA, we’ll see cybersecurity adopted by liberals in the same way gun sales spiked after Obama’s election. Overblown? Maybe. Like the Snowden revelations, though, by the time you know about it, it will be too late to protect yourself. So now is the time to get on encrypted messaging like Signal or Whatsapp, get a VPN (virtual private network), and change your friggin passwords to something better.

Have a beautiful, peaceful, prosperous 2017.

And change your passwords, really. There are some surprises you really don’t want.

Update (Jan 3, 2017): I just went through many of the security improvement steps on this excellent Medium post and suggest you do too.

(this blog was originally published on Medium at https://medium.com/@SunilPaul/top-5-tech-surprises-of-2016-1c571ce7155d)