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Garion Hall operates AbbyWinters, a popular adult entertainment website. Topics of the discussion include: the high price of moving a pornography site to AWS how to manage engineers when you don’t know much about engineering the difficulties of scaling search the myths of porn viruses why to start your own payment processor Our conversation was originally recorded for Software Engineering Daily but I am a coward and afraid of losing listeners/advertisers on that channel.

Vint Cerf is Chief Internet Evangelist at Google. He contributes to global policy development and continued spread of the Internet. Questions: What will the world look like in 5 years? What are the biggest problems associated with rapid spread and development of the Internet? Does blockchain technology present any solutions to these problems Why are cats so interested in blockchain? Are you worried about artificial intelligence like Stephen Hawking and Elon Musk? What is the “digital dark age”?

“I could forgive everyone who had ever hurt me and I could have power over that pain.” Right-click to download. Eva Kor is a Holocaust survivor and forgiveness advocate. She writes about life in Auschwitz concentration camp, where she and her twin sister were subjected to the experimentation of Dr. Mengele. Forgiveness is the tool she uses to overcome the pain which haunted her through most of her life. This is a crucial lesson: if Eva has healed from such a hellish scenario through forgiveness, anyone who is having trouble overcoming their own pain should consider trying it themselves. Why does forgiveness have such incredible power? “This is what happens to human beings. When we get hurt, we have a tendency to want to reach out and hurt back. The tragedy of it is that by hurting the people who hurt us does not make our pain go away. That is what I find that is amazing. People think that by subjecting the perpetrator to pain, it will make our pain lesson.” “I asked myself many years ago: if every single Nazi would have been killed after I had been liberated, would my life have changed one iota? The answer is no. I still would have been an orphan, suffering from illness and malnutrition.” Eva has forgiven Mengele, the doctor who performed horrific experiments on her while she was in the concentration camp. Her forgiveness is accompanied by pity. “I feel sorry for him. Any person who gets up in the morning and has no human understanding of what they are doing that inflicting pain on others is what they have on their mind, is not a happy human being. The Nazis were not happy people.” Years after the Holocaust, Eva became friends with Doctor Munsch, a Nazi doctor who had worked with Doctor Mengele. Doctor Munsch provided her with insight into what things were like for Nazis who got swept up in their role in the Holocaust, and who later were haunted with deep regret. “All the Nazi doctors got drunk at night because they could not cope with what happened during the day. He said the only other person that did not get drunk was Dr. Mengele. Mengele tried to justify what he was doing. He was telling Dr. Munsch that these kids would have been killed eventually and he was doing them a favor by keeping them alive longer.” “Some of the other twins looked at Dr. Mengele as a father figure. I never went that far. But it was a complex relationship, and I don’t think it has been explored much.” “Some of them liked him and said he was kind to them. He gave them chocolate and cookies. But I was always angry with him. I never got any chocolate and cookies from Mengele but I didn’t really want any. I looked at him as an enemy. However, I was emotionally and mentally aware that he would keep us alive only as long as he wanted us alive.” Eva was resolved to survive the experimentation which made her horribly ill. “I refused to die. I made a silent pledge to stay alive.” After escaping the Holocaust, Eva dealt with a different set of struggles. In Israel, nobody knew how to talk abut the Holocaust. For the most part, they didn’t talk about it, and Eva felt some ostracism. Then, when she first moved to the United States, she didn’t speak English. But gradually she learned to survive. And once she learned to forgive, she thrived. “I believe that there is a higher level of functioning on an emotional and intellectual level. I could not changed what happened to me or my sister. But I could change how I related to it.” “I could forgive everyone who had ever hurt me, and that I could have power over that pain, power over Mengele–it was a very interesting thought.” “Many Jews reject me because in Jewish tradition, they are saying that the perpetrator must repent and ask for forgiveness. That is giving the perpetrator power over my life, and that to me is crazy.” “I want people to understand that we all have power over our life. If we forgive those who hurt us, then they lose the tools to hurt me.”

“In trying to do anything substantive in life, you are going to have to understand that your adversaries are going to feel just as justified as you do.” Adrian Lamo is a threat analyst and hacker, currently working with ProjectVIGILANT in Washington, DC. Right-click to download. In 2010, Adrian informed the US Army that Bradley Manning had provided more than 260,000 documents to Wikileaks. “In the moment, I didn’t see it as pivotal in my life. I was focusing on the quantity of documents leaked.” “Many people say that there is an inability to point to any direct damage or loss of human life as a result of the leaks. That’s not a result of the leaks being harmless, it’s a result of fast groundwork and action to mitigate the leaks that the United States took in the months leading up to their release.” Why does the government need to classify some activities? What if we just open-sourced the military and declassified all documents? “There is some information that is not readily evaluatable by the public. There are things that you have to have some experience in national security to be able to judge if something is appropriate or safe. If you are approaching it from the point of view of John Q. Public without any context into how the national security process happens, sometimes it does look bad. But the whole picture is not being seen.” “The irony is that [the public] really can’t handle the truth. The truth is something that requires context. It requires involvement and internalization of it. You have to have a commitment to the process, to the importance of what is happening. It’s not something where you can just have a civilian review board look at it tabula rasa and say ‘let’s have some oversight of SEAL Team 6 by this collection of random activists.'” In a past life, Adrian was a “helpful hacker”. He would find security vulnerabilities in big corporations, which were accessible via web browser, then notify the companies of their weaknesses and offer to help fix them free of charge. Several technology companies were helpful and receptive to his infiltrations. But The New York Times responded with primitive ire, pressing charges against Adrian. “I don’t blame the New York Times. I understand the corporate mentality that led to their actions. I had always said that I knew what I was doing was illegal. The fact that it was helpful didn’t make it any less illegal.” Our broader world is so conservative that even the icons we look to as symbolic of fast, advanced societal change often make decisions that are grounded in outdated feelings and beliefs. The New York Times is supposed to be a bastion of progressive, activist thought–they should have been able to comprehend Adrian’s helpful behavior and the motivations behind it. “To that, all I can say is that their editorial mentality and their corporate mentality enjoy a certain cognitive dissonance.” There is a pessimistic narrative of fear around technology. Whether Anonymous is lamenting how 1984 has become a reality, or Occupy activists are decrying financial innovation, or robot-fearing Luddites are complaining that the impending shadow of flying food delivery drones portends a future where we will all be hunted down like in Terminator, the public is sure about one thing: the future is scary. In contrast to the usual offhanded comparison between our world and 1984, Adrian is in a position to give me a nuanced view on the topic of surveillance. “The irony is that I can speak to that from both sides of the table. During my hacking days I lived my life under the assumption that I was never not under surveillance. During the past five years, I’ve been very conscious that my movements are closely watched by people in the hacker and activist community who would like to see revenge exercised for my actions in the Wikileaks case and the Manning case.” “I basically behave as if the NSA is after me except its these extremely tolerant anti-surveillance people who don’t see the irony in their actions, who don’t see the way that they trivialize the value of my life through their rhetoric, saying ‘yeah, somebody should definitely put a bullet in him.’ It’s the same kind of rhetoric that trivializes the value of the life of those who are not completely with us, and so are therefore against us, the ‘terrorists'; both sides use this kind of rhetoric, that kind of trivialization of the lives of their enemies and they are unconscious of the irony that they are doing the exact same thing that they accuse the other side of doing.” Since we were talking about the specifics of modern surveillance, I asked Adrian about  the best way to form a mental framework around the Snowden case. “I wrote an answer on Quora that said that Snowden is essentially much more fracked than people think he is. He has most likely had far more of his secrets pried loose than he realizes. Russia has a world-class intelligence shop. He has likely been manipulated in ways that he does not even realize. I don’t think that he missed the significance of the fact that Russia is extending his asylum year by year. They don’t make any long-term commitments to him.” “If you look at the history of the relationship between Russian and Western intelligence, when they have this sort of situation, when they have this sort of high-value target, what usually happens is that the United States gets their hands on somebody that Russia values more than Snowden, and a trade will be made, probably covered as some kind of violation of the terms of Snowden’s asylum, and that will be the end of his run as a free man.” “The aiding the enemy charge was ridiculous in Manning’s case, but it would very much fit Snowden’s. He went to China first then Russia. You can’t go to aiding the enemy any more unless you went to some Sunni tribesman in Waziristan and tried to shop the material.” What about the argument that these programs impact people in ways that people can’t understand or evaluate, and that the public needed to know about them in order to pass judgment on them? What if the only avenue Snowden saw to expose those programs was an avenue that coincidentally “aided the enemy”? “The only avenue he saw was to approach a country that exercises these programs with much less restraint.” “He didn’t try [to take steps within his job at the NSA]. He skipped straight directly to defect. That, I have very little respect for. It’s an action that requires–I hesitate to say bravery–but moral certitude. It’s not an action that shows he made a genuine effort to work within the system. By not doing so, he really denigrates all the people who have worked within the system, who have availed themselves of these outlets, who have tried to affect change within the rule of law.” “There have been Freedom of Information Act requests about his actions, and none of them reflect an effort to work within the system.” This runs contrary to the common belief that Snowden made strong efforts to make changes from within the NSA. “In the hacker community people assume I have the government’s interests in mind. On the government side, people assume I’m playing both sides in some way. But people listen.” “I’ve tried to work within the system, and I feel like I’ve had some success in trying to prove that not all hackers are at the extremes of society. In the government, there is some common ground to be found if only the poisoned relationship with hackers could be fixed.” To illustrate this point of supposed enemies working together, Adrian pointed out how after World War II, the German scientists who helped get the US get to the moon were formerly aiding the Nazis in trying to kill Americans. Adrian has publicly disclosed his 2010 diagnosis with Asperger’s. I asked him if he thought people diagnosed with Asperger’s developed more acute symptoms after being diagnosed, because the diagnosis medically sanctifies antisocial behavior. “When I was diagnosed, it was something of a relief. I could feel that I was no longer weird–I had an actual formal diagnosis for some of the odd aspects of my behavior. When I was young I had to learn social cues consciously in order to emulate certain reactions that came naturally to neurotypical people. I would hazard to say that the social reactions that one has to emulate consciously are more real than the ones that someone’s brain wires them into automatically without any conscious thought.” “I certainly have never used it as an excuse for any particular behavior. We all own our actions and our behavior and much like I never felt ‘helpful hacking’ excused it as an illegal act, I haven’t felt that Asperger’s as a diagnosis excuses antisocial acts.” Adrian once overdosed on amphetamines he had been prescribed. I was also once prescribed stimulants for ADHD. The drugs were explained to me as being very well-understood, and deterministic in how they would affect my body. But the reality is that they are more of a black box. We do understand how some of the inputs and outputs relate, but we have a weak understanding of the reasons why. This is much different than how well we understand a computer, which is a man-made, thoroughly understood system. “Most of neuropharmacology is essentially guesswork. We know that lower levels of Serotonin are correlated with depression. We know that restricting Serotonin reuptake is associated with remission of depression. But there are many drugs that work on other receptors.” “We’re just

 “Carefully examine your assumptions. Many of those are not necessarily wrong, but temporarily eliminating them can expand horizons.” Right-click to download. Dima Korolev is an engineer and data scientist who has built many products and worked at Google, Microsoft, and Facebook. He isn’t shy about expressing opinions that may be misunderstood or taken offensively. This interview was an opportunity to ask him about some of those opinions in detail. “I started at about age 15 with microware. I enjoyed algorithms. My first few jobs had to do with software for microware and computer. My first real software job was in 2004.” “I’m happy I did not grow up in the US. I think the US culture growing up-wise is more about impressing your immediate parents, teachers, and peer group. Which is essentially terrible for someone like me who tries to do their own things. “It kills creativity quite a bit. Those spikes of people who want to grow further are rarer in the US. People are more polished, but also more demotivated.” “The US has commercialized the idea of raising children and educating them to a huge degree. Parents assume that the more money they invest in their kids, the better the education they will have.” Since moving to the US, Dima has moved among different cities and seen how the engineering styles and cultures differ from place to place. He compared the places he has lived in terms of lifestyle, personal productivity, and hiring employees for a software company. “Seattle data-driven companies are more vertical. Companies in California are more things that spread, like Mongo or Redis.” Dima has considered how these native differences would affect potential users in those areas. “If the best way to build a company in the next few years is to hire people in California, I will be in California. I’m going to be where the business requires me to be. If I need to be in Seattle, or Europe, or Asia, let’s see how that works.” We explored some broken aspects of tech culture. Why is there a lack of women in tech? What prejudices do Indians suffer in Silicon Valley? Why are there so few Mexicans in tech? As two white males in tech, Dima and I have not suffered from much discrimination directly. But we are compelled to talk about it. Discrimination leads to weaker companies, disenfranchised employees, and a world that is less pleasant to live in that it could be. Next, we talked about some engineering trends–Node.js and big data. “New languages emerge every day like quantum particles. Some of them stick. I would expect a new programming language once in a while to disrupt the industry. Node happened to be one of those languages. 90% of the speculations about why this happened with Node, instead of Go or Python or Ruby–they are just speculation.” “If I have to give my number one reason why it’s popular, it would be the paradigm of being single threaded eliminating many of the ways you could shoot yourself in the foot. It’s harder to run into concurrency issues. But Node is young enough that we have not seen the flaws of the language and the environment around it.” Dima compared Node to the early days of Ruby on Rails, and contrasted those two frameworks with .NET’s inability to reach the same level of popularity. How effectively are companies taking advantage of their own data? “Technologically, we are still very primitive. I hope to fix it. You cannot build an established product without data pipelines.” “A friend of mine said a really great phrase: ‘remember those times in early 1990’s when every single brick-and-mortar store wanted a webmaster and a small website. Now they want to have a data scientist.’ It’s good for an industry when an attitude precedes the technology.” “We are witnessing the emergence of CEOs realizing that they need to understand their data.” To close our interview, Dima gave a broadly applicable piece of wisdom. “Carefully examine your assumptions. Many of those are not necessarily wrong, but temporarily eliminating them can expand horizons.”

“Two-sided marketplaces are very defensible businesses once you get the wheels spinning. You become a preferred way of clearing a transaction over time.” Right-click to download. “When I was 14 years old making thousands of dollars a month it definitely got to my head a little bit. Over time I realized that money is not everything and I pulled back on it, but it definitely bred some jealousy in high school.” “People definitely thought I got lucky, not realizing how hard I worked, that I stayed up until 3 or 4 in the morning. There was a lot of self-sacrifice. My friends were out drinking and smoking on weekends while I was behind a computer screen. It definitely didn’t come free, by any means.” “I’ve had the unfortunate experience as being featured on the Yahoo home page as a success story. There were about 3000 comments on the post, and most of them were very negative, people taking their own personal failings and frustration on me. I stopped reading through them.” Two-sided marketplaces are a theme across Matt’s most successful businesses. “Everything we’ve started we’ve tried to charge money for on day 1. We’ve never tried to build consumer webapps to sell to Facebook for a billion dollars.” “The last three businesses were all marketplaces. Two-sided marketplaces are very defensible businesses once you get the wheels spinning. You become a preferred way of clearing a transaction over time.” “Look at eBay, it’s a very old business. But you look at their financial filings–it’s a very nice company. Look at Craigslist, it’s the #1 place to get an apartment in San Francisco. It’s not because other people haven’t built websites with better UIs and better backends. Craigslist is where all the liquidity is, so it’s hard to dislodge.” “I like businesses that create a lot of value in the world and take a small transaction fee. At 99designs we have paid out tens of millions of dollars to designers. At Flippa we’ve helped people sell hundreds of millions of dollars worth of websites and domain names, taking only a small transaction fee. And at Hired we have helped hundreds of companies find fantastic engineers, designers, and product managers for a fraction of the fee of traditional recruiters.” “We’re ultimately just a conduit which money flows through.” “The genesis for Hired was our own frustrations with recruiting engineers at 99designs. As the company was scaling we were doing all the traditional things: job ads, recruiters, LinkedIn…at one point we were using thirty different recruiting agencies. I didn’t think they were earning the value they were charging.” “I went on AngelList and went through 450 different recruiting and HR startups with the hope of finding something, anything better, but everyone was playing around the edges of the problem. There were startups doing video interviews, applicant tracking, background checks, personality and cultural quizzes, a bunch of companies selling scraped data. Nobody was saying I’m just going to get paid if I put a warm body in a seat.” “Over $300 billion put into headhunting and recruiting fees every single year. Why isn’t there a single go-to place where I as a CEO or CTO can login and view the 400 best engineers who are interested in jobs in a given week? So we decided to create it.”

The biggest impediment to people’s success is that they oftentimes forget that the external signs of success–the external validation–has nothing to do with you as a person. Rafe Furst has started businesses, studied cancer, and earned degrees in Computer Science and Symbolic Systems. We started off by talking about our shared past–professional poker. Right-click to download. “Poker is really a zero sum game. For me to win, somebody else has to lose. What we see is, the market for poker has become very efficient. You don’t have to spend thirty years of your life on the road risking life and limb. In the course of a year, you can play the same number of hands online and learn to become a world-class player.” “It’s more like a video game. The kind of skills you need are more geared towards young video game players. It’s become more quantitative. In a similar way, you can look at what happened in Wall Street to mutual funds when eTrade and Schwab came in.” “Over time, when you have a zero sum game and open up the market, it becomes more efficient. The edge that I used to have [in poker] is gone. A lot of my friends–they can’t compete anymore.” But can anyone compete? Poker has become an increasingly fluctuative, painful career for most players due to the hypercompetition. “There will always be some great games…to get into the juicy games, you have to be likable. There is a unicorn game effect.” Why aren’t there more new games? Why are we still playing with 52 card boring decks? “With new games, the edge can be bigger as people are figuring out the rules.  It’s hard to be a world-class expert in every single game. There’s always an evolution and invention of new games. This leaves an opportunity for people who are really good thinkers.”   “Humans have a risk aversion bias. We would rather not lose $100 than take a coin flip for $200. Enough people have to be comfortable enough with a risk to play it together.” Are there situations in poker that cannot be thoroughly solved? Does a player have to make mistakes sometimes? “You can’t fully solve some problems analytically. You have to take a probabilistic or heuristic approach. Over time you get more confidence in your strategy.” “In Artificial Intelligence, there are a range of techniques that are probabilistic. Bayesian reasoning, for example. At the end of the day, you have a to do as good a job as you can at making a probabilistic conclusion.” Crowdfunder is Rafe’s fourth company. “We’ve been operating Crowdfunder to bring investment funding to everyday citizens. This is not for idea stage–it is for actual companies. On Crowdfunder you can offer people investment opportunity and tell them why its a good opportunity.” “Neil Young had a vision for bringing back high-definition audio. He created this product called Pono, a high-definition digital music player. He launched it on Kickstarter and validated the marketplace. Several months later, they were ready to raise investment. In a matter of several days they had millions of dollars of investment interest.” Rafe concluded by offering a broadly applicable piece of wisdom. “The biggest impediment to people’s success is that they oftentimes forget that the external signs of success–the external validation–has nothing to do with you as a person. You can remind yourself, when things are not going well, to not beat yourself up.” “I’ve had many ups and many downs. I’ve learned it the hard way. When you’ve had big setbacks and big failures, it’s hard not to take that personally. But I come back to–there’s always folks that know you best, who love you and support you.”

“The way it actually works is that you have an idea in mind, and science throws something in your direction and you have to pivot.” Between the university and the corporate world there are as many tensions as there are synergies. Inna Vishik is a physicist finishing up her postdoc at MIT. Among other things, she writes about how research priorities within academia differ from those within a corporation. Right-click to download. “In some ways academic research is fundamentally different from industrial research. The main difference is the degree of openness. In industry, there are trade secrets. In the current dichotomy between academia and industry, where they are fairly separate–they sort of have distinct roles.” “This is not the only workable paradigm. In the early part of the twentieth century, there was more basic research happening within industry, within Bell Labs for example.” “Another model is private foundations. That is kind of an intermediate model that is closer to academic research, but I guess the distinction is where the money comes from and how the institution arises.” “I study exotic materials. The way people decide to study a new exotic material is that a new one gets discovered randomly, or theorized. ” “Everything I do would not be done in industry. The fact that it doesn’t have applications in a five year or twenty year horizon is a problem. The way it actually works is that you have an idea in mind, and science throws something in your direction and you have to pivot. I don’t think that would fly in a situation where an end product is required.” What are the fundamental problems in academia, whether or not they could be fixed? “There are scientific problems and there are personnel problems. On the scientific side, funding is often very trend-driven. There is more funding for the latest, hottest topics. It is important to push the boundaries of science and be open to new things, but at the same time there are unsolved things in the older topics.” When funding leaves one area, sometimes it never comes back. “The personnel problem is bigger. The job market is sort of like professional sports. There might be one or two job openings, and you might need to go anywhere in the country where there are those jobs. That was great back in the day when scientists had portable spouses, but in modern times that isn’t a reality. Furthermore, in America, what we have seen in the past century is an increasing urbanization. More people live in cities, but universities are often in little podunk towns.” Bill Gates is incentivizing publications to tear down their paywalls. Science Exchange allows you to offload experiments to a marketplace.  Will these types of developments affect how research is conducted going forward? “Paywalls are a big deal. There was a move in congress recently that if you receive grant money, your publications must be open to the public. Open access seems like a good idea and potentially it is, but there are some things to keep in mind.” “Most publications are very arcane. They are directed to a specific group of people. How many people would be reading these? Most people would rather read journalism, or a more digestible piece written by the scientists [who are publishing in the paywalled journal].” “If all of the publications were free, it would come down to the authors, or the scientists to get things published. When pushing for open access, people need to think about the negative consequences that might have on the authors of the papers, and weigh that against the fact that most people would not read these scientific journals.” “Crowdfunding of science is another idea that sounds great–if you are not in science. How much can you actually earn in a Kickstarter campaign, especially for something esoteric? A couple thousand dollars?” “It’s similar to people who have educational startups and are trying to disrupt the education system without consulting with teachers, and seeing what’s feasible in that space. The change may have to come from within.” According to Steven Weinberg, particle accelerators incubate and stimulate technology as much as war does.  Inna expressed skepticism that this is true, but gave the quote some credibility. “Throughout history we have seen that war pushes technology in every single conflict. But who wants to wish for more war? The best thing you can hope for is some concerted effort among thousands of scientists to solve difficult science and engineering problems. It might not yield the same degree of positive returns, but it has almost zero negative consequences.” What causes scientists to leave academia for industry? “The calculation is more about the relative quality of positions, where quality is measured by all sorts of metrics–freedom, income, family life.” “For me personally it’s almost exclusively about quality of position I can get hired for, as well as geography. Within academia, there is a sort of inaccurate idea that people leave mostly for the money. That’s not necessarily true. It’s a host of personal reasons.” Inna also gave her take on why Quora is so useful. “Information is fundamentally a social construct. To qualify as information, someone needs to share it one way or another. In that sense, the idea that someone will read what I write and be able to understand a concept better is very empowering. This connection between information and social is one of the reasons why Quora works so well.” In closing, Inna discussed a problem that plagues both academia and industry. “There’s a big discussion of women in STEM. Within academic Physics, one of the biggest problems is how much it is talked about. It has a negative impact on how women perceive the field. Whenever I tell a female I am a physicist, they say ‘wow, there are not a lot of women there.’ That’s all they have heard about the field, and it really colors how they think about entering it.” “Implicitly within that, there is some message that women are not as good for some biological reasons.”

“In brain surgery, there are no winners, there are only survivors. I didn’t die, and I’m grateful. As far as I’m concerned I’m supposed to be dead.” Mahbod Moghadam is a founder of Genius, a platform for annotating the web. Right-click to download. “Genius was originally an art project. Then it got traction. We did Y-Combinator and raised money from Andreeson-Horowitz. I was the first full-time employee.” “Then I had health problems. I had a brain tumor and I had to have brain surgery a year and a half ago. After that, it started to be too much to me. Then I got in trouble for writing annotations on Elliot Rodgers’ manifesto, and I decided to resign.” Mahbod’s humorous, distinctive personality is not always understood or well-received. “I’m always trying to be funny. In tech especially, there are a lot of people who have never been funny in their entire lives–and they’ve never even tried. It’s kind of tricky–you have to put stuff on the line. In Czarist Russia, the czar would kill his court jester every couple of months. It was the most dangerous job you could have.” “I’m not the only one who suffers from this.” Mahbod referred to Trevor Noah, the new host of The Daily Show, who has been raked against the coals for vaguely antisemitic joke tweets. In a TechCrunch interview a few years ago, the Genius founders joked about taking prescription stimulants. I asked him whether drugs were significant at Genius, and about the acceptance of drugs in the wider technology culture. “This is more of jokes and rhetoric taken seriously. Everyone keeps quoting our TechCrunch Disrupt interview. We weren’t even taking it seriously. We wore sunglasses onstage as a joke. Nobody in the audience was listening, nobody was paying attention. We made some jokes about Vyvanse, it’s not indicative of anything in the culture.” “Everyone got carried away about our jokes and three and a half years later people are still talking about it.” “Here’s a thing about tech culture. It’s supposed to be about challenging hierarchies and disruption. Tech has turned into dinosaur worship and nepotism. We’re all sitting around worshiping these rich old guys. To keep up the facade of disruption, we talk about drugs. Doing drugs doesn’t make you rebellious, it makes you part of the system.” Mahbod told the story of his brain tumor. “I started getting the serious symptoms in April 2013. The brain surgery happened in October 2013. That whole summer I was a mess. My left hand was shaking uncontrollably. The left side of my face was paralyzed. I had a full batch of interns to manage. The shaking of my hand made it really hard to type.” “The week before I finally went to the doctor, I was a mess. I was sleeping 14 hours a day, had dark circles under my eyes.” “They had to try the MRI 3 or 4 times because I was shaking so much. Immediately they said to go to the emergency room right now. I was such a mess I didn’t even have my cell phone. They let me use the hospital phone to call my co-founders. The first thing I said was ‘hey guys, can you bring my cell phone?'” “At that point the tumor had deteriorated my mind so much that I didn’t know what was going on. When the anesthesiologist was explaining to me how the anesthesia was going to work, I was on Tinder.” “They said the tumor could blow up at any moment.” “In brain surgery, there are no winners, there are only survivors. I didn’t die, and I’m grateful. As far as I’m concerned I’m supposed to be dead.” We talked about a variety of other topics–venture capital, streaming music services, and whether musical innovation has stagnated. In closing, Mahbod provided some wisdom, and lamented that many of the people tech are misguided. “Don’t sit there and quote your heroes. Let’s get rid of this gerontocracy, this kissing-old-person-ass in tech. I’m a huge fan of technology, but I’m hoping that the tech bubble crashes just to get rid of all these fakers. I think it’s going to be really good for the Internet when the current bubble crashes.”

  “I’m a storyteller and I believe that the best way to change someone’s mind about anything is to tell them a story.” Right-click to download the podcast. After abandoning a career in law, Cristina Hartmann is pursuing a career as a full-time writer. She is also deaf and blind. We corresponded over a shared Google Document where she gave me long-form answers to my written questions.  Because everything was already written, the entire conversation has been copied to this post. Thanks to Jessica Su for reading her answers and doing a great job. Jeff: I want to start off with a quote from one of your answers. You write: “Most people have never met anyone like me. I’d go as far as to say a lot of people are afraid of me. The worst thing is that I understand why. I’m their walking nightmare: someone whose perceptions are so different that they can’t possibly start to relate. Funny thing is, I understand them far better than they understand me.” Tell me more about this quote, and how this sort of interaction affects you. Christina: The thing is that … most people assume that others’ perceptions are similar if not identical to theirs. They depend on auditory and visual cues for many social interactions. For example, before talking to a stranger, you tend to make eye contact. It gives you implicit permission to talk to that person. When people encounter someone like me–which isn’t often to begin with–whose visual and auditory perceptions aren’t all that great … they don’t know what to do. They don’t know if they should shake my hand. They don’t know how to talk to me. They don’t know how to touch me. What most people perceive to be ordinary quote-unquote rules for social interactions aren’t there anymore. I make people uncomfortable because the rules no longer apply. They don’t know what to do. A lot of people hate not knowing what to do, so they either resent it or avoid it. Other people just assume that a life without sight or sound is a terrible life. I’ve even had people suggest suicide to me as a viable option, which, by the way, isn’t really good advice for anyone. I don’t think they were trying to be cruel, but some people are just so attuned to the sensory worlds that the prospect of losing their sight and hearing is too awful to even consider. From their vantage point, no life seems better than life without sound or sight. I think they’d think differently if they were actually in my shoes. Jeff: How do you feel about those interactions, where people suggest suicide? My first reaction is always anger. To blithely suggest suicide to anyone is really an insensitive thing to do. Suicide isn’t something anyone should take lightly, particularly when they don’t know a lot of facts about that person’s life. My second reaction is a deep sense of sadness that there are people out there who assume my life isn’t worth living, that nothingness is better than what I have. It’s a depressing thought that I try not to indulge in very often. My third reaction is disgust. These people who have such cavalier attitude toward suicide see it as an easy way out. It’s not. Even if a person stop living, that person leaves behind others who loved them. If I decided to commit suicide, I’d be leaving behind a family who’d be crushed by my choice, friends who would question what they could’ve done to save me, and two cats who won’t get fed because I’m gone. Even if I wanted to off myself, I couldn’t do it in good conscience. I’d leave behind a lot more hurt than I’d cure. I don’t take these people seriously, but the mere existence of those people depresses me a bit. To be honest, I hate the fact that I make people uncomfortable and afraid. That’s the last thing I want … I’d just like people to be relaxed and cheerful around me. I also hate the fact that people think my life isn’t worth living. I just want a toned-down and easy interaction, but that’s not always possible. But, there’s not a whole lot I can do about other people’s discomfort toward me. I can’t change what I am. If I want to get all psychoanalytic on myself, I’d suppose a lot of my drive comes from the desire to prove people wrong, to prove that my life is worth something. Maybe I won’t ever become Picasso or a master cellist, but I can do some stuff. And … you know, I’ve done a lot of things that I’m proud of. I’ve traveled to a lot of places. I’ve learned a lot of things. I’ve met a lot of people. I’ve had a lot of great experiences. I’ll have to get off the psychologist’s armchair and settle for that. Jeff: I understand that your deafness and blindness have affected who you are, and I do want to talk about that–but I also want to talk about who you are outside of that. What are you doing day-to-day as an occupation? What are your goals and pursuits? Christina: Well, I’m a writer … or, more accurately, trying to be one. In a weird way, my disability has given me the freedom to do what I want with my life. I get enough money from the government to survive, so I write. My life is tediously ordinary. I get up, feed the cats, make breakfast. I read a little before I write … and sometimes I end up writing more on Quora than I should. Bad for business. I cook a lot–and right now I’m really into braising meats–and try to keep my place reasonably tidy and clean, which I’m usually not so successful at. Boring, ordinary stuff, really. Right now, I’m finishing up a book that has been a long time in the works. It’s called “The Formula,” which is about a nerdy computer science student who becomes … da da dum! … a pick-up artist! I’ll admit that I had entirely too much fun creating my own pick-up technique, which I hope is an improvement on existing PUA approaches. There’s also a lot of other things in this book, like gaming and the financial industry, but pick-up is at the heart of this novel. I took a lot of wrong turns and ran into a few dead ends with this book–which is my second, by the way–but I think I’ve found my niche in terms of stories I want to write. I discovered that science fiction is something I love to read, but not necessarily something I’m good at writing. I’m more into contemporary issues that relate to the Internet and our culture. In terms of my goals and prospects, I’ll admit to being entirely too single-minded. My shorter-term goal is to finish “The Formula” (probably in the next two weeks) and shop it around for traditional publishing. I’d absolutely love it if I could get this one on the bookshelves somewhere. Jeff: Why don’t you self-publish? Isn’t that more lucrative and straightforward? Dealing with gatekeepers seems like a big negative of the publishing industry. Christina: I self-published The Secret Value of Zero, so I’m pretty well-aware of the upsides and downsides of self-publishing in general. Self-publishing is great if you’re good at publicity and are targeting a niche audience. For example, that’s how Fifty Shades of Grey jumped ship from self-published to commercial publishing … the author had a pretty concentrated audience of erotic readers who liked Twilight fan fiction. If you have a niche audience, your publicity push is much easier since you can go to speciality websites, contact certain blogs, et cetera. Self-publishing is a do-it-yourself project at its biggest. You’re not just the writer, you’re also the publicist, you’re also the one handling the fomatting, you’re the one managing the different sales platform. It’s great for people who can do many of those things very well and I’m not really one of them. The thing about my book, The Formula, is that it has a more general audience. It’s more of a coming-of-age story of a nerdy computer science student who desperately wants to quote-unquote better himself and gets involved in the pick-up artist and seduction community. That’s more of a general fiction kind of book, so I’d have a really, really hard time marketing that as a self-published book. Not just that, but I think this book has a shot at making it big since there’s not very many–if any, since I can’t find any–fiction books out there that takes a hard and in-depth look at the seduction community. Of course, you could argue that a lot of the PUA manuals are fiction, but we won’t go there. I really believe in this book so I want to get it out there to as many people as possible and commercial publishing is–bar none–still the best way to do that, distribution-wise and publicity-wise. Publishing–either self-publishing or commercial–is kind of a devil’s bargain. With commercial publishing, you sacrifice some profit margins for a far bigger audience reach and a more polished product. With self-publishing, you maintain a higher profit, but you’ll have a smaller audience size and it’s very difficult to turn out a product that is equally polished and diversified as a commercial publisher’s. It is indeed possible–some self-published authors do this–but I don’t have enough patience or attention to detail to be able to do a smash-up job on formatting, marketing, and all that. Being self-published can be very rewarding, but it’s also very, very hard and requires a lot of overhead … and it’s just not something I’m skilled enough at. I’m rather curious to see how agents and publishers will react to this book. Hopefully, it’ll be a positive reaction, but we’ll see. My longer-term goals are in

Right-click to download the podcast episode. Jeff Nelson had a problem. “In 2006 I was working on the Google Accounts team. I was writing a browser extension, and what I was finding over and over again was that restarting Firefox in Ubuntu was a particularly slow operation–like 45 seconds. At the time, there wasn’t a way to reload an extension and dynamically start the extension without resetting the browser, and this was really slowing me down as a developer.” “What I did was find a way to restart Firefox faster.” Jeff forked a Linux distribution called Puppy Linux and began using it for his development. “Puppy Linux is designed from the ground up to run in RAM entirely, and this is different than other Linux extensions. That has enormous advantages from a performance perspective, because you eliminate I/O as a bottleneck. The Firefox restart went from 45 seconds to less than 2 seconds.” As with many innovations, what began as a narrow solution to the inventor’s problem showed broader promise over time.  Starting in 2006, Jeff led a campaign for his vision of a webtop. Repeatedly spurned by management, he left the company in frustration before his ideas reached fruition. His vision has been carried out by other people. A modern Chromebook is a laptop running Chrome OS as its operating system. The device is selling exceptionally well. “It’s more of a system than a device. When you are using a Chromebook, you shouldn’t need an offline Unix environment. That was never the intent. It is this online environment that allows you to access all of the services on the network. It is the hardware in your hands, plus all of the services we are delivering to you.” Jeff feels he has been written out of history. The most vocal Googlers who have addressed Jeff’s complaints claim he deserves no credit. They believe that his thread of innovation was disjoint from that which birthed an actual consumer product. “A lot of this controversy where some people are saying that I shouldn’t get credit comes from the fact that people feel like I am taking credit away from them. That’s just not the case. I’m putting an accomplishment that I did on my resume.” “After I had built the initial prototype, I was so impressed that I brought it in and showed it around to some of my coworkers, as well as the director of consumer products I was reporting to, David Jeske. He kind of resisted it.” “It was developed as a raw prototype, that had to be online all the time.” You couldn’t use Chromebook on an airplane. “Because the team didn’t want to pursue this as project, I ran it by myself.” After several more months of solo pursuit, he sent a prototype of his operating system around the company. “At that point product management got involved, because there was a powerful response. It did become a project. The main guy on the Chrome team, Mike Jazayeri got involved [as a PM]. Eventually we presented to Larry Page on the whole concept.” This momentum proved temporary. “It was December 2007 where I made the decision that it wasn’t happening. I was getting too much pushback from my own boss.” “My own boss didn’t like the concept and didn’t want me to keep working on it. We had presented to Larry Page, Jeff Huber, Brian Rakowski. We had even taken it outside of Google, to HP and ASUS. It was going extremely well, except that the person who didn’t support the idea was my own boss.” “I did attempt to change teams, and that soured my relationship with my direct manager even more. He wanted me to stay on the team and keep doing what I was doing. My own manager didn’t want to let me go.” “It was company politics. People have this amazingly high regard for Google, but in the end, it’s a company. The same kind of corporate interplay nonsense that you have to deal with at any other company still occurs at Google.” Michael O. Church’s description of “software politics” echoed in the words of Jeff Nelson. “Some of that amazingly high regard for Google as a perfect company is not entirely well-placed. It’s still a real company with real problems and real people working there.” “I had exhausted all of my options. I knew that without going over the head of my manager, I couldn’t change teams. It came down to the fact that I wasn’t having fun anymore, so I left Google.” Since Jeff Nelson left Google, Chrome has taken off as a browser and an operating system. In the meantime, Jeff has taken criticism for trying to claim credit for his work. Were the Chrome team’s efforts completely agnostic of Jeff Nelson’s work? That is unlikely. Mike Jazayeri worked closely with Jeff Nelson when the product had positive internal momentum at Google. Jazayeri  also worked with the Chrome OS team. At a minimum, the cross-pollination between Nelson and Jazayeri has impacted the trajectory of Chrome. “I don’t want to claim that when I invented Chromebook I wrote every line of code.” “I worked on it for a year and half, I wrote two patents on it. I left Google in 2008, and those patents were actually filed in 2009, a year after I left the company.” “If there is any animosity coming from the Chrome team about why I have this accomplishment on my resume, all it would take is two words from Larry Page and it would clear this up. I am getting slammed by these one or two guys that seem to think they know what happened, when they really don’t know what happened.” “To some extent, the only reason we are even talking about this is that I happened to write the patents and Google decided to file them. If not for that, we wouldn’t even be talking–everyone would think I am this crazy guy who claimed to create this project. The purpose of a patent isn’t to back up your resume, but in this case it has become that.” “People in software don’t think about intellectual property ownership as the guy who created technology, they think of the guy who is working on it right now.” “The guy who worked on it eight years ago–they ignore that. There is that disconnect because people in software don’t view innovation in terms of the guy who started the idea, who wrote the first version.” Jeff emphasized that he is not looking for a zero-sum form of credit. He doesn’t want to subtract from the claims of anyone else. “The other innovations–the people that created them deserve credit as well.” A crucial question is whether Chrome would be as successful if not for Jeff Nelson. “I don’t think so. I was the first person to build this project. We had meetings up and down management.” “I called my initial prototype Guppy. When the Chrome team got involved, we created a new project called Google OS. In sometime around March 2008, there was a new project created called Penguin, which was similar to Google OS, but didn’t use a window manager. It ran entirely in a browser.” “Around July 2009, they launched Polar Bear. It brought back a window manager, and looked more like Google OS. Offline mode came around 2009 as well.” “My theory is that Google may be concerned with something like an intellectual property battle. I think they are worried that they will lose ground if they give me credit for this.” “They should just clarify exactly why these patents are in my name, why they filed them. It would be a non-issue at that point.” Since leaving Google, Jeff Nelson has recalibrated his career goals toward starting a machine learning company. “I’ve been working for the man for a long time, and I want to go back to my roots of trying to start my own company, take an idea to fruition, and know that I’m building my own company and can take it to the next level. I’m trying to build a team of really exceptional people.” “The market as a whole has started to appreciate machine learning. What a lot of companies are doing now is kind of naive. I think that there’s a next level that a lot of companies–even Fortune 500 companies–haven’t appreciated at this point. Over the past month, I’ve been trying to meet with as many companies as I can to identify the big problems that aren’t being solved yet.” “A lot of companies jumped into this Big Data hype without understanding that they actually had to do something with that data.” “After leaving Google, I didn’t want to just go get a job. I wanted to try to build my own company. That’s a very big decision to make. It’s easy to get a job in Silicon Valley. It’s not easy to start a company.” “Google has this extraordinary mythology of being the best company to work for ever. When you make the decision to leave, it’s to some extent difficult to recover and decide where to go next. You are leaving this company that has been perceived as Charlie and the Chocolate Factory.”

Michelle Roses writes on Quora about motherhood, relationships, Judaism, and life lessons. “Quora has been pretty therapeutic. It’s been a way to write about experiences and connect with people who like reading them, or who can relate to them.” “I don’t usually write answers or share unless it is something significant. I don’t have many joke answers–I have to feel some kind of connection to the question, that I can either add to or comment on in a different way.” We compared our respective Jewish experiences. Though both of us have had our conflicts with the religion, we differ in that she has found a Jewish identity she is comfortable with. “I was raised Jewish in the south. It’s not as prevalent, so growing up I was a minority when it came to religion. That’s affected me a lot. What was hammered into me was: you have to learn these traditions. You have to learn all this stuff so that you can carry it on.” “The thing that was missing for me was spirituality.” “I still don’t hear a lot about the spirituality. It’s still all about learning the traditions, learning the prayers, learning the holidays and history. It never becomes about a relationship with God. I think that’s why there are so many Jews that find a different path.” Michelle told me about her experience as a television anchor. It was a good excuse for me to ask for some advice around interviewing. “It’s about having a conversation more than asking questions and getting answers. You are leading a person on a specific train of thought. When that happens, people actually say more than they would if you asked them questions that are very specific.” “People just want to have a conversation, and the more comfortable you can get them, the more information they will give you.” Right-click to download.

“We are capturing the world’s knowledge in a way that is different than anywhere else.” Jonathan Brill is the Writer Relations lead at Quora. He came on The Quoracast to talk about his background and his role in the Quora community. Throughout much of his origin story Jonathan worked in Sales and Marketing. “I took a retail clerk job in high school, and the person who ran the chain of stores was an old salesperson at Xerox. He was able to teach me the communication style to maximize opportunities.” “Early on I was pretty interested in what made the business world work.” He has studied the entire history of business, from the robber barons and the seedy beginnings of IBM, to the modern, unique models of Facebook and Quora. The more things have changed, the more they have stayed the same. “In traditional business, there were three parts of the business. You either made stuff, sold stuff, or were administrative. I pegged myself early on that I would be in the sell-side.” “You have to go out and meet with people and explain [the product] in a way that people can understand. I gravitated towards the idea that I wanted to work with people directly and only on groundbeaking new technology that would have to be explained, where the benefit wasn’t necessarily intuitive.” Quora upended his conventional understanding of businesses. “In businesses like Quora, there isn’t necessarily a sell-side, or a distribution arm. Facebook is a good model. Salespeople for the advertising product were there from the start, but it would be weird to call them core to the business. There were lots of companies that sold advertising, but Facebook is different because of the level of engagement.” “Overwhelmingly, the value of Facebook’s business is on the make-stuff side of the house.” While I was delving into his background, I found a surprising lack of material about Jonathan online. He told me this was in accordance with his past desire to keep a light digital footprint. “Prior to joining Quora, I was a business-to-business salesperson. One of the things you have to be careful of when you are representing a company is allowing people to be biased against the company because of something you wrote. I felt like putting too much of myself out there might have been a liability.” “I kind of grew out of that over the past couple of years. But even then I had to be very careful about what I said.” I proposed that maybe the world is moving in a direction where users benefit from disclosing more about themselves online. Specifically, I was thinking of James Altucher, who rose from the ashes of his embarrassing failures by writing about them candidly. “I think it’s completely the opposite,” said Jonathan. “Everyone should worry a lot more about what they are putting online. Having a digital footprint is like having a credit history. Having a bad one is better than having none at all, but you don’t want to have a bad one.” The purpose of Jonathan’s role at Quora is to act as an intermediary between the users and the engineering team. “The principal mission for me is to positively impact the writing experience at Quora by providing feedback from the writers into the product team, and working in a closer way with people who are doing a lot of writing.” “There are things that I can impact that the product team cannot exactly do.” Jonathan contrasted the experiences of Top Writers with the rest of Quora’s user base. “The experience of writing on Quora may be the same, but the Top Writers are writing more, and spending more time on the site. Even before I joined the company, I was probably on Quora upwards of 20 or 30 hours per week, just having the app open. I don’t use Facebook or LinkedIn the same way. My experience [on Quora] is unique. If I’m spending 10 hours a day in my feed, I need something different than someone who is checking it for 15 or 20 minutes per day while they look for something to write about.” In a discussion about how Quora is growing into the mainstream, he pointed to LinkedIn as an analog. “There are some places where knowledge of Quora is assumed. And in some places not as many people know about it. Facebook has achieved critical mass globally and is in every language. Quora is in English only, and we are still in a phase of early growth.” “From the time Adam started the company, he has been consistent that the mission of Quora is to build a place where we are capturing the world’s knowledge in a way that is different than anywhere else.” “The hardest thing for most people is finding out what to write about.” When blogging, Jonathan argued, 80% of the time is not spent writing. Much of it is spent on formatting, distribution, and other ancillary activities. “Writing on Quora is fundamentally different. If you are looking to write in volume and you want to get a lot of people reading what you write, it’s difficult to find a better place than Quora.” Right-click to download the episode.

Laura Hale is a PhD student at the University of Canberra. She is currently working on a thesis about social media methodologies. She came on the Quoracast to talk about her pursuit of an effective strategy to studying social media. “It helps explain my world.” “For me, playing with the data is very relevant to what I do. At some level, it’s easier to do stuff on a short-term basis. I can just grab a set of data and work on it.” From an early age, Laura actively studied the social world around her. “My dad said that teachers tend to call on boys more than girls, and I started tracking that. I showed the data to the teachers and they were not amused.” “The higher-level point of my thesis is to develop a methodology for looking at social media data. Many times you can use smaller data sets to make decisions about data. They don’t need to have huge patterns with all sorts of math. You can do things like mean, median, mode.” Laura has applied this in her research into correlations on Quora. “The problem with Quora data is that there is no public API. And you also cannot scrape data. But if you keep repeating little experiments you can begin to get an idea about what variables matter. I went through posts with pictures and counted them manually. Once I have the data, I look for patterns. Graphs are helpful.” “At this point, because I have done so many of these things, I have developed a sense. If something doesn’t fit, I have a pretty good idea of it. When you are getting the same consistent results time after time after time, there is enough truth in it that things can be reliable.” “The results are nice, but the methodology is more important to me.” Right-click to download.

Cyndi Perlman Fink is a writer and entrepreneur. During the first Internet boom, she sold her company Cyberdiet for $22 million. “I was working 24 hours a day on this website. It was my passion. My partner was a registered dietician. We were always putting up new articles and thinking. My husband would walk in and say ‘I don’t understand what you are doing, you aren’t making any money.'” Cyndi taught herself programming when she was 50 years old. Then she built her business with the skills she acquired. “I am a firm believer that any problem can be solved. I believed I could teach myself programming and I went out and bought books. I would sit there with the books open for hours. And if I couldn’t get it, I would just do it over and over again until I got it.” “Eventually I knew I could do everything myself when a problem came up and I knew how to fix it without looking at the books.” “When we started, we knew the site was going to be diet and health related. We knew we would never sell vitamins and potions and lotions. We wanted to give people menus, and support, and information. We had a community, and it was so vibrant and people loved it so much, that we finally had to start splitting it into groups and subgroups.” “One of the fellows on the site was over 300 pounds and couldn’t even walk out of his door. He was housebound. We started working with him, and he went from not being able to walk half a block to hiking the Pacific Crest Trail. Cyberdiet changed his life.” “The first month we had 426 visitors. By the end of the first year we had over two million. That was with no advertising.” “Then we were in Newsweek, Time, and Playboy. Forbes Magazine picked us as its best website of the year. That was a milestone. As the years went by we got more attention.” She showed me the award she got from Forbes. It was a golden computer mouse. “The site was crashing under its own weight. We had to keep ramping up with more servers. We didn’t mind putting in the money and the time.” Cyndi regrets going to work for the company that ended up buying Cyberdiet. “I went to work for the company that bought Cyberdiet. What I took away from that experience was that when you sell your company, you should walk away.  They changed it so much. There were ads everywhere, and they blinked. Remember the blinking ads?” “That was the wild west. Nobody knew anything.” Right-click to download.

“It’s a classic case where you have to be contrarian. It seems like the worst idea in the world to start a cloud hosting business. We didn’t know any better.” Moisey Uretsky is the cofounder of Digital Ocean, a leading cloud hosting provider based in New York. “It’s the usual immigrant story. My parents moved to America when we were four or five. We were poor and didn’t have much money so our parents focused on education.” Moisey told me about his early years, and how he started working on technology with his brother Ben. “I was bored during my first summer break and my brother had a job at a data center company and I just started reading books about it. Two weeks later he told me to take over as a sysadmin. From there we started our first company.” Prior to Digital Ocean, Moisey worked on ServerStack, a hosting business similar to Digital Ocean. He also tried to start a hedge fund analytics company, which he had difficulty making successful. “I did make one sale. I had some sales experience from ServerStack. The first year was just me working and pretending to be four people. But ultimately, product-market fit in that category is extremely complicated. It’s pretty much a nightmare. I don’t envy any financial services startup.” Moisey has built on the learnings from ServerStack and his financial services company. “It was tremendously formative. We made every single classic business mistake. This was a decade ago when there wasn’t much of a New York City startup community. We didn’t understand how to attract customers or market properly. We weren’t able to capture the success that was available in the space. It’s easy to start, but it’s hard to scale.” Digital Ocean was founded in a time when the field was rife with competition. Amazon Web Services, Heroku, Google App Engine, Rackspace, and others had created a market that seemed saturated. “It’s a classic case where you have to be contrarian. It seems like the worst idea in the world to start a cloud hosting business. We didn’t know any better.” “What was missing from all the other providers was simplicity. I have a background as a developer and a sysadmin, and yet they were still too complicated for me.” “With AWS, the learning curve is very steep. It could be a little daunting for people just starting out. There are a lot of things that are no longer relevant that you are forced to think about. These are carryovers from days when hard drives were counted in megabytes not gigabytes.” Everyone else was putting engineering first, and not product first. “If you get a bunch of engineers together, often times you are going to get an engineering-focused solution. We always went backwards from the product side instead of the engineering side.” Moisey found himself personally delighted by the product that Digital Ocean was building. “It took us about six months to build Digital Ocean. When we spun up that first server, I was like ‘this is amazing, all I want to do is build a Rails app and spin up some more servers.’ We knew that if we could deliver that feeling to other customers we were on to something.” He pointed out similarities and differences between Digital Ocean and Heroku. The two companies both allow easy onboarding for someone looking to deploy an application to a hosted environment. But Digital Ocean offers more options for simple yet advanced configuration–a huge upside for businesses that need to iron out small problems that magnify upon a business’s event of scale. “When you get past the point of hitting product-market fit, you can experience really fast dramatic growth. At that point, you want to be more hands-on. All of those 1% errors that you could ignore with 100 users, they begin to creep into the picture.” “With Heroku, it’s a bit more curated, but when it doesn’t fit your product, you might need to go find something else.” This spectrum between ease of use and configurability parallels the spectrum from small business use cases to large business use cases.  “That’s why AWS is so large.” Large businesses require lots of knobs to turn, so those customers historically have had to turn to Amazon Web Services. Digital Ocean has found a sweet spot along that configurability/ease-of-use spectrum. Digital Ocean was started as a spinoff project from ServerStack. This strategy leveraged both the hardware and the domain expertise which the Uretskys already had. “If you look at start-ups that have hardware as well as software–it’s a lot harder. If you have never bled in a data center, you don’t know about the problems you are going to encounter.” “We ran two companies at the same time. Eventually, Digital Ocean had to acquire Server Stack. Server Stack was like the incubator for Digital Ocean. We learned from the mistakes we made. Without the experience of Server Stack, we would not have been able to build Digital Ocean into what it is today.” Digital Ocean’s customer service complements its easy-to-use product offerings. I asked if it was difficult to scale the support team. “The way to scale anything is you get a good product. If you have a good product, you get less support questions. If you hire aggressively, you get less support questions. It’s a thing you put into your mission statement early on. When we didn’t have much funding, there was probably a 50% chance that I would be answering a customer’s support question.” Moisey told me about his experience growing up with his eventual cofounder Ben. “We came to America, and we were always passionate about computers, but we were really poor. We got a computer when we were 13 and used AOL and a dial-up modem. My mom was starting to use Visual Basic, and I stole her book and printed out the huge Windows API because I wanted to make my own app. I got about halfway through. It was doing stupid stuff that kids do. Cracking software and whatnot.” “We always had a strong work ethic. One thing leads to another, I never had a resume, never worked a job. You never see things from the perspective of an employee if you’ve never been one. You always think about how you can push forward.” “For me and Ben, it was a situation where he had a job and I stopped by to learn stuff and he gave me a job. The company we were working for was going out of business. Working with family is a unique dynamic. One thing that I can say for certain is that whatever the dynamic is with the brothers, that will be the dynamic within the office.” Locating a tech company in New York has its perks as well as its hazards. “Ten years ago, it would have been [difficult]. But today, you have a large number of local VCs and Silicon Valley VCs with local offices. The thing is, the best people are always hard to find. The benefit to New York is that there are people that get burnt out on other cities. And there all of these offices for Twitter and Facebook and Google,” and employees are sometimes willing to leave those companies for Digital Ocean. “Technically speaking, we should be in San Francisco. But we love New York.” I asked a question about what sort of economic boom we are in, which he answered with subtlety. “The internet as a whole is still growing. Developers as a whole are growing more as a sector than any other degree. And we’ve been doing this for twelve years. Because we’ve already gone through a downturn, and it didn’t really affect what we were doing, we’re optimistic.” “Until you can stream HD right to your Oculus Rift, we haven’t reached peak internet usage.  There’s still a lot of growth in the emerging markets. Globalization had a lot of negatives and a lot of positives. We can really be a part of that globalization of information.” Right-click to download.

“Anyone should be able to innovate and express themselves at any time. The barrier to them is going to go down to almost zero. That’s what all of technology is for.” Nancy Hua is the CEO of Apptimize, a company developing software which equips developers with A/B testing and analytics for their Android and iOS applications. Coming out of school, Nancy pursued algorithmic trading. “When I was at MIT I interned at Merill Lynch. That’s when I got interested in finance. I could tell that it was the kind of thing I would like.” “With algorithmic trading I could tell that it had immediate feedback. When I was a kid I always wanted to do science. I didn’t acknowledge other options in the universe. The minute I tried research, I instantly realized it was not what I could do. I need something that is instantly competitive and gives feedback in what I’m doing.” That type of quick feedback was the same feeling that users of Apptimize would later be empowered by. “I left finance because I knew what the future was going to look like if I stayed, and it wasn’t exciting to me.” “When I think about the people who are having the most impact in the world, I don’t think about the richest people. I think about the scientists and the innovators.” Nancy disagreed with the unsubtle condemnations of algorithmic trading, exemplified by Michael Lewis’s Flash Boys. “There are different types of algorithmic trading. The type that we were doing was really good for the world. Most people don’t know why capital markets or financial instruments exist. But to have a really good first-world economy, you need this kind of structure.” “It’s automating things that people are doing on the floor. Nobody actually trades in the pit any more.” There is a distinct contrast between the cadence of algorithmic trading and that of running a web 2.0 company. “I had no idea what starting a business meant. Algorithmic trading is about challenging yourself, and it’s isolated. You have your team, and all the data that’s coming in from the exchanges, but you don’t have customers. It’s much more insular.” “People definitely get addicted to it. There’s a tighter feedback loop than in my current business, so in that sense it was easier. But I like that [operating a business] is harder. You have to make a bigger bet on the future.” Nancy described the origin story of Apptimize. “My co-founder and I were working on a lot of different projects when we made our AB testing framework. We prematurely made this thing because we had an app that needed AB testing.” “We had some friends that had an app called Robot Invader, who put our framework on it. And all of a sudden we were installed in tens of thousands of users.” “I liked that we could let people innovate better and faster.” “We let anyone change their apps in real-time for AB testing and optimization and targeting. It’s how all of the top apps in the app store work.” “Think about your favorite app. Do you know how many product iterations it took to make it so good? It’s probably hundreds or thousands. The average product does not have time for that.” “It can take a start-up on average two dozen iterations to get users. If you are waiting for 24 product iterations, your product is going to die before it gets off the ground.” “A lot of the AB testing that our users are doing is to free up developer time.  The apps that don’t have AB testing infrastructure set up are in a period of constant redesign. They push out an app, and then they don’t work on it any more because they are building a new version of an app. That’s kind of crazy because you aren’t learning about what you have done.” “It’s much more efficient.” “The main thing I learned from The Lean Startup is that you want to instantly validate what you have done. As part of the development process, you have to instantly see that it affects metrics, and that you can test a hypothesis.” “You need to see your users using your product, and you need to know what they do. What are they doing the first three minutes they are using your product? What were they doing before they used your product?” Apptimize supports developers who need this sort of speedy testing and validation. “I like the idea of eliminating developer time as much as possible. The vast majority of what we think we need developers for are not what we need developers for.” Anyone armed with Apptimize can alter functionality of an application despite not having a technical background. “Anyone should be able to innovate and express themselves at any time. The barrier to them is going to go down to almost zero. That’s what all of technology is for.” “All you will need eventually is your own creativity and a web browser.” The current culture at Apptimize is ideal to Nancy. “You start a company or join a small company so you can have a big impact the culture. To only work with exactly the people you want to work with you have to start a company.” One theme at the company is self-improvement. “I’m aggressive about making sure I’m getting better. If you don’t improve dramatically in an environment like ours over time, you are going to get crushed. The environment gets more competitive over time.” I asked if she agreed with the Peter Thiel philosophy that competition is for losers. “Comparisons are odious. But you need to always think about comparative advantage. When I think about competition, it’s a signal if we are losing a competition, that we are doing something wrong.” Nancy quoted Box CEO Aaron Levie when describing how she thinks about Apptimize’s existential risk. “I want to be the one disrupting other industries, not being disrupted. The only way to do that is to know more than everyone else, and to not be disrupted. I’m always worried about something coming out of left field and disrupting my industry.” “I want to make sure we are a driver of that change, and not just a passive recipient.” While she doesn’t believe that Silicon Valley is in a bubble, she does point to certain thematic fundamental risks among some companies. “A lot of these companies don’t have a vision. Some start-ups have a product, but then they need to manufacture a vision. In those cases, they should really think about whether they want to pursue that into a whole company.” In closing, Nancy provided a piece of wisdom that aligns with her two primary goals in life: to enable and empower people, and to connect with people. “There’s more that you have in common with anyone in the human race, even if you really hate them, than you would with someone who is not a human being. We’re really programmed to think we aren’t like each other and won’t get along. That’s just not true–it matters what happens to someone, even if they don’t have the interests or privileges of your situation.” “We are all responsible for those random people that we never see.” “It’s hard for people to think on that level. Fifty years ago, there’s nothing you could do to effectively help that suffering. But now, that’s not true. We have a lot of wealth and a lot of resources and we can all help each other if we can change how we think about it.” Right-click to download.

“The education system in India has created dreams and ambitions, but by not having the right markets and institutions, it has made people desperate.” Balaji Viswanathan is an entrepreneur, writer, and engineer. He writes about education, technology, and the changing social landscape of India. Among his many pursuits, teaching others gives Balaji the most energy. His current platform for educating others is MBA Bootcamp. “We try to provide a way to provide an aggressive MBA program online, and to find ways to fix the education system. The education system is broken in terms of accessibility.” Balaji started an online university several years ago that did not work out, and he sees modern MOOCs repeating some of the same mistakes that he made. “The primary mistake is going after the big mass of people. Coursera is going after hundreds of thousands of people, and there is no exclusivity. People don’t take it seriously. If you make the entry barrier low, the exit barrier is low.” MBA Bootcamp seeks to correct some of those problems. “People go to school to make networks, and the existing online schools do not focus on making networks.” “A hybrid approach is needed. Everyone in an MBA class has a similar purpose. The people are all pre-vetted.” When something is pre-vetted, you don’t need to wonder whether the person next to you in class is a jerk. “Many of the MBA programs are at such a price point that it prices out 99% of the entrepreneurial people. That’s why we want to bridge the gap. The traditional model is so expensive. But there are some benefits. But it is very expensive to pay for to network.” The key to a successful online education platform is to be selective on the right criteria. “The vetting could be on entrepreneurial abilities rather than money.” “There is no perfect standard for vetting. But we want to filter on the entrepreneurial mindset. To do that, you have to show what the previous things you have started are. You could have written a book, created an album, created software.” Balaji’s first funded company was Zingfin, which used social media data to predict stock market trends. He told me the story behind Zingfin’s creation and its inability to succeed as a product. “In 2008 Lehman crashed. That day, I was interviewing for a subprime trading desk at Barclay’s.” “Before that time, I was very active in an investment club at Microsoft. I was doing some day trading in oil and gold. I started writing blog posts about the coming recession. The week Lehman crashed, I shorted the entire financial sector.” “Within Microsoft, people had worries and fears about the coming crash. But the broader market sentiment did not have access to that insight.” This was the inspiration for Zingfin. Zingfin was a compelling product with obvious potential for value-add. But it faced immense technical and market challenges. “I botched one of the sales rounds. In a video we made, I was poking fun at how financial advisors were overpaid. It went against us.” The bank he was trying to sell Zingfin to took it personally and was offended. “They saw that we were not in the right mindset for them. This is how sales can fall through in the enterprise. If your messaging is even a little problematic, they can kill it.” “We were caught with a product that needed to be deepened, and no funding.” I asked Balaji if social media will ever be securitized. Will there ever be a day when I can buy a call option on Justin Bieber’s number of Likes or Retweets? “A stock is something that creates value. A stock market is not a zero-sum game. But betting on Justin Bieber is a zero-sum game. If one person wins another has to lose.” “Philosophically I’m against this, but someday there may be markets for it. When there is much more randomness involved, it is pure gambling.” “If someone could prove it’s not totally random, it could make more sense.” Balaji describes himself as having had “way too much school.” Despite having two masters degrees, he believes college is unnecessary for 99% of people; universities are institutions that are largely outdated. “The whole lecture concept came from sermons. University was never meant to be a place to teach career skills.” “Some of the ancient universities were completely free. People could come and have all these discussions. The only reason people came was to explore knowledge. There was a bunch of things they created in that place.” “99% of us don’t care that much about philosophical aspects–we need career skills.” If something like Quora could provide the philosophical knowledge, and another platform could let people network, and something else provided career skills, we wouldn’t need traditional universities so much. “We spend the best four years of our lives in college. That is a time when we should be building stuff. The model I have been trying to propose the last few years involves building stuff.” There are exciting projections about how the developing world will change over the next few decades. Billions of people are coming online for the first time. I asked Balaji how these projections would play out in reality. “For India there are a lot of challenges. How are we going to educate a huge mass of people who are ambitious? When the markets are open, people get much more ambitious, but the education system has not worked. People are poorly trained.” “When we are saying we will have 1 billion people coming online, how can we make sure these people have a job that gives them wages?” “oDesk’s model could be built in a way where the developing world could use. It makes everyone into entrepreneurs. As a freelancer, you are taking control of your life. But the quality control is so low.” “Nobody is going to give you a job. That 1950’s way of thinking is gone. That was a very unique time. In most of history, people have been entrepreneurs. That was how the world worked for thousands of years.” “That was the industrial revolution. In the post-industrial revolution, people have to start acting like entrepreneurs.” “The industrial revolution made college into a necessary institution. You go and study something for four years that prepares you for a lifelong career.” Now that is invalid. “People are going to change careers every five years. People are getting forced into entrepreneurship. A big corporation is not going to train you, it’s not going to give you a pension.” “Entrepreneurship is going to be the primary form of job creation.” “The education system in India has created dreams and ambitions, but by not having the right markets and institutions, it has made people desperate.” Right-click to download.

Jacob Jaber is the CEO of Philz Coffee, a coffee retailer with 17 locations around California. Philz is known for high-touch customer service, interesting blends, and lack of espresso. “My dad was running a grocery store, and experimenting with a lot of coffee varietals and all these special blends. We didn’t use much machinery and didn’t have espresso. I’ve been involved since I was ten years old.” “The best coffee in the world is the coffee that comes to your taste. At Philz, we have the platform to optimize for that. When you can talk to your barista or your chef, it’s a much more special experience. It may seem inefficient, but there is beauty in that inefficiency.” “It’s really special. The concept is tightly tied to our values and our philosophy, and we love it.” There have been three waves of coffee: the home brew wave of Folgers; the second wave of Starbucks; and now the third wave of high-touch coffee shops. “Starbucks revolutionized the way people think about coffee. They are part of the second wave. There’s this third wave: the artisanal micro-roasters that put a lot of care into crafting the perfect cup, and procuring the highest quality beans. However, Philz is different–we are in the people business. And many people in the third wave think they are in the coffee business.” “Our vision is to reinvent the coffee experience.” An example of that reinvention is the lack of espresso at Philz. “A lot of times it’s not about what you do, it’s about what you don’t do. We’ve converted a lot of latte drinkers into Philz drinkers.” As Starbucks grew, the culture became diluted.  Jacob is focused on scaling the culture at Philz correctly. “In the beginning, when my dad and I were working alone as baristas for 14 hours a day, we did great. It was hard, but we cared, it was ours, and we were committed to delivering a great customer experience. Bringing on our first employee was easy because we were right there with them.” “Culture is the collection of normalized behaviors that occur regularly. First and foremost, you need a strong commitment to hiring people with the right values. And you want to have a training process that represents the culture of the company. We make sure our trainer is a cultural ambassador.” “We spend several thousands of dollars to train one individual.” Maintaining the culture at Philz is about simplicity and repetition. “I don’t say a lot of different things. I say the same things over and over again. Every conversation is an opportunity to reinforce why we do what we do.” Jacob emphasized that he was not intimidated by the challenges of scale. “Business is common sense, not rocket science.” “I get inspiration from people, but not so much from companies.” His biggest influence is his father, Phil. “My dad is basic–he’s authentic.” Prior to becoming CEO, Jacob was occasionally fired by his father. “In the early days of being a barista, he kicked me out in front of a line. I was almost crying. There were some arguments and disagreements over the years, but it’s gotten better.” “When I was 16 or 17, I had to work 7 days a week, and some days when I’d finally get a day off, he’d call me in.” “Every kid will disagree with their parents. I wanted to do a lot of things my own way.” As a teenager, Jacob was not motivated by academics. But he excelled in work and hobbies. “I wanted to get an outside experience. I worked at Abercrombie as a greeter. They told me they wanted me to just stay at the front and sell everything.” “I never liked school. I hated it because I was forced to learn what I wasn’t interested from people who weren’t interesting. I used to play a computer game called Diablo. At first I sucked, but after eight months I was top ten. I can be incredibly focused.” “I’ve always been motivated by excellence, impact, and learning.” “There are a lot of similarities between games and business. Business isn’t complicated. What has helped me at Philz is my lack of experience. I come at things with a fresh perspective.” “I imagine the best-case scenario and I aim for it. I learned that from the gaming. The game has taught me resilience and determination, and those are the same things that make someone successful at business.” “I spend probably an hour a month looking at financials. I spend all my time with people. The output is the financials. I reward people for giving customers and team members a great experience.” “Don’t focus on the results, focus on the inputs.” “We don’t have a fear of money. We focus on doing what’s right, because we know it will reward us in the long run.” “It’s simple. It’s all hard work. There’s no easy way out. You gotta work smart, and you gotta work your tail off. The simplest things matter.” “Retail is tough. Every business has it’s own challenges. You can’t scale authentic human interaction. You have to hire great people, give them some guidance, and give them freedom. It’s not easy, but it’s really rewarding.” “Being able to walk into our 50th or 60th shop where people are happy to be there–that’s success to me.” Another scalability concern is providing food to customers. Many coffee shops fumble and wind up with subpar options. “Food is very important. It’s the second highest sales item after coffee. I’m passionate about health and quality ingredients. But we never want food to overshadow the coffee experience, and we don’t want to prepare, so we want to find great partners–craftsmen who can provide the highest quality.” Much of Jacob’s spare time is spent educating himself. Since he is young, he welcomes advice with a measured humility. “I love learning so I read a lot. I love Quora. It’s one of the best websites in the world.” “You gotta be smart enough to recognize when you don’t know it all. You gotta have responsibility and have people who believe in you. You gotta be open-minded, especially to elders. When you have those things, age is less important.” “The issue is that you don’t know what you don’t know. But you also gotta be careful of getting too much feedback from the experienced folks. A lot of times, experienced folks have less of an open mind.” “I’ve always thought for myself. I’ve never just taken what somebody’s said and believed it.” His parting wisdom was to be authentic. “Presentation is not as important as authenticity. I’m not the most tactful person, but I speak my mind.” “You should be kind. Be authentic.” Right-click to download.  

Stan Hanks was the founding CTO of Enron Broadband, which collapsed with the rest of Enron when the corporation went bankrupt in 2001. Stan left the company prior to the collapse, when he started to grow suspicious of the company’s strategy and leadership. “At the time, one of our big recruiting challenges was hiring people in a highly competitive market. We actually had to compete with Google on hiring. This was ’96 or ’97 and we had wireless Internet everywhere in the building.” “The corporate culture was always to hire the best and the brightest, and to make them prove they were the best and the brightest.” Stan led an ambitious project to enable trading of bandwidth. Broadband as a commodity. “To make this work, we had to get more bandwidth than we knew what to do with, and we had to create applications that required so much bandwidth that you could not use them in a non-commodity environment.” “I was building the biggest IP network in the world. We were trying to find places to build capacity that nobody else had ever built. We had guys digging holes, laying fiber.” “To make commodity trading make sense, you have to find a way to commoditize it in a way that makes sense in the industry. You have to find a pain point. In coal, or soy beans, the product is fungible–you can say ‘this is grade A, it has these characteristics, it provides this value.’ You know what it is, you can trade on price exclusively.” “In the case of bandwidth, the price benchmark we used was not relevant to anyone in the industry. Over the course of time, that could have been rectified, but that was not the way things worked out.” The bandwidth trading project was Enron’s equivalent of a moonshot project. But it was not an unprecedented challenge. “Enron had created markets before. They had created markets for carbon transfer credits, and weather derivatives.” Some of the technology worked, but Enron presented it as working even better. Enron’s mission was to optimize the stock price. Perception was prioritized over actualized technology. “A lot of the things that transpired in the analyst conference in 2000 that sent a lot of people to jail talked about things in specific ways.” “It was not possible to deliver on some of the technical promises. The streaming video–it worked, but it had issues. The server for Real Player had this huge memory leak, for example.” “It was still a long way from being there. Saying ‘we have an architecture defined’ is different than saying ‘we have a finished building’.” But upper management interpreted the situation selectively. Like the mark-to-market accounting with which Enron cooked its books, the plans for Enron Broadband were treated as a finished product. “There was a characterization between what happened at WorldCom and what happened at Enron. At WorldCom, they misreported some revenue accidentally, and didn’t have the moxie to step up and restate things. At Enron, it just felt different. The tone and tenor was more of a carnie side show, where the game is rigged, and you know the game is rigged. You think you can knock the milk bottles over, but we’re gonna take your money anyway.” “Overnight, our head count doubled. And there was a shift where decisions were no longer being made on the basis of long-term thinking. They were being made on the basis of mark-to-market accounting, and a trader’s book of business. But if you don’t actually have the bandwidth in place, you can’t sell it.” “We had equipment, and stuff sitting in warehouses waiting to be deployed. But we had a real clear misunderstanding of what the business that we were in was looking like, and how we had to manage that relative to a traditional Enron business.” “I had very candid talks with both CEOs, and I got resources allocated, and scientists and engineers. But there’s this feeling–an inconvenient truth. We really had to do something, we couldn’t just claim that it was done. And the extent to which that involved effort beyond what was imagined by the folks in Houston was really daunting.” “The tipping point was when we started treating the entire business like a trading book. We had purchased this stuff that was sitting in warehouses but we couldn’t get permission to deploy it because it screwed up the way the books looked. And that’s really where things shifted, and nobody in the C-suite was willing to stand up and say anything.” With traders taking precedent over technologists, Enron became a financial abstraction of its former self. “The guys on the trade floor–some of them had engineering degrees. But Enron was a case of greed. People acted in accordance with their compensation. It made it really hard to form teams.” “We ridiculously compensated people for making money for the company on paper. It was a real difference between how Skilling ran the company versus his predecessor.” As technology has advanced, so has the potential for financial obfuscation. I asked Stan whether he thought there could be a corrupt technology company like Enron on the market today. “I look at where the money comes from in these companies, and it makes you wonder.” “I think of a herd mentality a whole lot. There were so many people building networks, and all of these guys talked as though they were going to get all of the bandwidth that existed. You couldn’t make any sense of it. As soon as someone cuts the price, everyone has to and it’s a race to the bottom. The telecom nuclear winter of 2001-2005.” “I’m skeptical of herd mentality in everything.” Right-click to download.