CoverWallet Raises $18.5 Million Series B

CoverWallet, founded in 2016 by serial entrepreneur Inaki Berenguer, continues to be one of the fastest growing startups in New York City. It is focused on reinventing small business insurance, making it easier for small businesses to buy and manage their various policies, all online. Prior to CoverWallet, buying and managing the insurance policies small businesses need, has been a terribly tedious paper and pen process. None of this process had been digitally consolidated until now. 

This week CoverWallet announced its $18.5 million Series B investment led by Foundation Capital. The round also saw participation from existing investors such as Union Square Ventures, Index Ventures, CV Starr, and Two Sigma Ventures. CoverWallet was named one of the most entrepreneurial companies in the US by Entrepreneur Magazine, and has raised over $30 million to date.

Hacking for Defense and Diplomacy

Stanford University is pioneering in many ways, and one of the latest is in considering how to best pair "fuzzies" and "techies" to address some of our gravest societal challenges. Steve Blank, the legendary entrepreneurship professor who all but created the Lean Startup movement now accelerated by Eric Ries, has brought the customer development model to the industries of defense and diplomacy through his courses known as "Hack 4 Defense" and "Hack 4 Diplomacy."

In today's Net Politics blog for the Council on Foreign Relations, I outline how Blank partnered with two retired U.S. Army Colonels to bring together some of the most intractable problems from the U.S. Military, Defense, Intelligence, and Diplomatic communities together with some of the best of the best in tech. This pairing of political scientists and defense experts together with technologists is a tremendous example of hands on blending of fuzzies and techies.

This engagement brings together comparative advantage, and ensconces code deeply in context. It's not tech in search of a problem; rather problems are sourced from agencies drowning in them. In 2017 more than a dozen more universities will roll out their own H4D programs, creating a brilliant crowd-sourced approach to solving some of the most challenging problems in the world.

The Fuzzy and Techie of Neuroscience

Fuzzy and techie may be terms from Stanford University, and the title of my forthcoming book on the need for balance between the Liberal Arts and STEM, an end to the faux opposition. But they're also timeless terms that can describe the beauty and magic of many discoveries. Take, for example, the brilliance of Santiago Ramon y Cajal. According to Joanna Klein of the New York Times, he was "an artist, photographer, doctor, bodybuilder, scientist, chess player and publisher. He was also the father of modern neuroscience." He deftly merged art and science like so many great thinkers, and brought both the fuzzy and the techie into the field of neuroscience.

Cloudstitch On Data & Design

In the process of building an app or site there's usually a lot of repetition. If, for example, you're trying to create multiple screens for an app or a site, you're often left copying and pasting design elements. A Y-Combinator startup called Cloudstitch just made this a whole lot easier by allowing Google Spreadsheets and Microsoft Excel to link directly to Sketch, the design platform. Last week they also built a plugin for Framer, demonstrating how fungible this technology is.

Now, if you want to populate a design with live data, say name and bio information from a LinkedIn profile, you can simply add the data to fields in a Google Spreadsheet, and link that spreadsheet to Sketch. Sketch then replicates your design and populates each new element with data from the next row in the Spreadsheet. The result is that you can auto-generate dozens or hundreds of elements instantaneously all from the spreadsheet, rather than the design file. 

This is the type of new tool that is dramatically reducing the barrier to entry for non-technical folks to play major roles in the development of new tech tools. Whereas it once might have taken a back-end engineer, a front-end engineer, and a designer, today it can all be done by one person, and that person need not be very technical. This empowers designers to take their work along a greater spectrum, from development to design to near production. Companies like Cloudstitch are changing the game, and improving access for both fuzzies and techies

Automation and Human Substitution

MIT economist David Autor is one of the leader experts on our rapidly changing world of automation and potential for human labor substitution. In a wonderful article for the MIT Sloan Review entitled, "The Shifts – Great and Small– in Workplace Automation," he unpacks the reality that middle skill, highly-repeatable jobs (both cognitive and manual) are at risk of machine automation. But he also states that this overlooks the other reality; that when machines automate certain sub-sets of jobs, namely tasks, they complement other more human capabilities. When these human capabilities that we know more tacitly, such as abstract thinking, complex problem solving, empathy in dealing with others, managing human relationships, etc. are complemented, they amplify the comparative advantage of these more "fuzzy" abilities. The value of these abilities goes up as machines substitute away the routine, codifiable, machine-readable tasks. There are very real needs to be concerned over shrinking middle-skill jobs such as clerical or service work in retail, hospitality, or food services, for example, and we need to be thinking about how this affects income distribution and opportunity. Autor points out that middle-skill occupations such as admin office work, sales, and machine operative work has shrunk from 60% of jobs to 46% between 1979 and 2012. Meanwhile service occupations that are higher-touch human facing, management, and professional technician jobs have grown. The highly cited example of ATMs is another. While between 1995 and 2010 the US went from having 100,000 to 400,000 ATMs, heralded to eliminate the bank teller, but bank tellers over the same period grew from 500,000 to 550,000. While ATMs increased by 300%, bank tellers also grew by 10%. The human skills became higher-level importance, and banking became more relationship-based.

How are our schools and education system helping these individuals up-skill (and also low-ego into trying new things). We can't build a wall to keep the robots out, so how do we consider how these automations will enhance the human condition? How can we align our skills with their gaps, so we complement one another? We need people to be technically literate, but we also need to co-invest in our creativity, breadth of thinking, and problem solving. We need to develop the capacity for becoming both more fuzzy, and more techie.

Are you a Fuzzy or a Techie? Both.

The myth that you're either a "Fuzzy" or a "Techie" is a prevalent one. As evidenced by the many questions on Quora, we think of this as an either/or phenomenon. You either get an English degree or you're a gifted coder with every job at his or her feet. The truth is it's far more complicated and those with breadth of exposure, passion, and curiosity are poised for success. Many "techies" read great literature and play the violin, while many "fuzzies" are eminently quantitative in how they structure historic data sets in the social sciences. Being technical doesn't mean being narrow, or having rote thinking. Look at a systems engineer, for example. Nor does being fuzzy mean that you have no ability to manage data. Look at every PhD in economics or political science to see the quantitative requirements prevalent in all modern social science. 

What's it like to be a Fuzzy at Stanford? 

What is a Fuzzy at Stanford? 

What's the proportion of Fuzzies and Techies on Quora and campus?

Democratization of the Tech Tools

Having grown up in Palo Alto, California, I've had the real privilege of seeing first-hand the incredible changes in technology over the past twenty-five years. What used to require a greater mastery of infrastructure is now being democratized and packaged up. The Full-Stack Developer has given way to the Full-Stack Integrator, someone who can master the macro assembly of the pieces. For example, as I've geared up to launch my book The Fuzzy and the Techie, which comes out with Houghton Mifflin Harcourt in April, to use the Silicon Valley phrase, I'm "eating my own dog food." I'm using these very tools that I write about and talk about their accessibility. 

Here's a list of some of the tools I've found helpful to launch a book: Amazing overview of tech learning resources out there. Curated list of the best of for learning everything front-end, back-end, data science, etc. Bento creates "tracks" where all you have to do is follow their lessons that point you to YouTube, Coursera, Udacity, Code School, Codecademy, Treehouse, and other amazing resources to learn everything you need to know.

Sublime Text: Incredible visual code editor that allows for stylized error checking across any language you could be learning or trying to develop in. Great integration and ease of getting saved, pre-written chunks of code from GitHub's online open source repositories (repos) to your editor. Great way to run web scrapes off LinkedIn if you need email addresses. By using LinkedIn Premium (free trial for a month) you can easily pull most email addresses you need. For about $150 you can get credits to scrape up to around 10,000 email addresses. Skrapp is out of Paris. 

PersistIQ: Easy email automation or drip email platform for sending out emails in a non-annoying, non-HTML way. Send simple customized text emails in bulk to those people you want to reach.

Facebook Pixel: Simple Javascript you add to your website HTML to know who's been visiting your site. From there you can generate "Custom Audiences" and "Lookalike Audiences" on Facebook Ads Platform to retarget people who have visited your site. These audiences take into account common features or likes in your audience, and extrapolate probabilistically across a certain percentage of a market, like the US, that you want to target. For example, 1000 pixel hits can be extrapolated out into a "Lookalike" audience of one-percent of America. 

Facebook Canvas Ads: Great mobile optimized Facebook ad format that is highly immersive. Moreover automatic scrolling puts the engaged user onto your URL through scroll rather than clickthrough. Once they hit your site, they hit your Facebook Pixel, where you build audience.

Sketch: Photoshop 2.0 that's much, much easier to learn. Auto art boards make it simple to develop for any size format or screen, and you can export easily to Desktop, or to other apps like InVision or Framer or Zeplin to be able to take designs to the next step of interaction prototype. Sketch is out of The Hague, Holland. 

Noun Project: If you need beautiful, simple vector graphics of over 150,000 different items and icons, you can download them from the Noun Project, manipulate them in Sketch, and incorporate them into your design assets. 

Canva: Create great infographics or visuals for social media or Facebook Canvas Ads. Canva has great basic tools for image generation, and you can always export and bring them into Sketch if you want to customize them further before you add to your site or social media, already size formatted for Instagram, etc. Canva is from Sydney, Australia.

Framer: After you export your Sketch files, you can create interaction prototyping super easy by either manipulating the visual image and seeing how the code changes in the editor, or by manipulating the code and seeing how it changes the image. The code is CoffeeScript, which is a simpler syntax of Javascript. The CoffeeScript compiles to Javascript but isn't really production ready. Framer gets you very close to deployed product but then you need a developer to connect the dots to make it fully functional and ready for use. A place like UpWork you can hire that. Framer is from Holland.

Zeplin: Another tool like Framer. You can export your Sketch files to Zeplin and Zeplin autogenerates the CSS. CSS is the style code for the front-end design of your website. Rather than having to specify image dimensions and colors, Zeplin generates this CSS automatically upon upload. All you need to do is point your developer to Zeplin and it's all ready for them. Zeplin is from Istanbul, Turkey.

Cloudstitch: If you want to change content on a site dynamically, it's a pain. The way of serving content is called a CMS or a content management system. Cloudstitch creates a CMS that can autoupdate and run the content on your website, but do it off a Google Spreadsheet or Excel. What this means is if you're a restaurant owner and you want to sub in or change menu items, no more talking to your webmaster. Literally all you have to do is update your Google Doc that through Cloudstitch is attached to your website. Basically it turns Google Docs into CMS.

PSD2HTML: If you're close to deployment but not quite there, as in you've created all the Sketch files or even taken a stab at interactions in Zeplin, PSD2HTML will take you to the finish line. For about $100-300 per page they will connect these final dots and make it HTML ready. PSD to HTML refers to the file types for Photoshop to HTML which is web-ready code. They do more than just Photoshop, for example they work with Sketch, and all sorts of email automation, etc. 

Squarespace: If you get fed up with creating a customized site all on your own, you can always fall back on a great option like Squarespace to generate a great website, like this one, in a few hours to a few days worth of your time. All the tools are there, you just need to iterate on designs a bit to make sure it looks how you like. Sketch is a great design tool for these tweaks. 

The Fuzzy and the Techie: If this has been useful, please pre-order a copy of my book on the importance of the Liberal Arts in addition to STEM, the human behind our technology. We need equal consideration for context and code, ethics and algorithms, data and our biases, or in other words, Fuzzies and Techies. 

Faux Opposition: STEM vs. Liberal Arts

As highlighted recently in CBC News out of Toronto, about "Why more and more Torontonians are shelling out $10K for coding crash courses" there are tremendous new opportunities for those who low-ego, up-skill, and take on the challenges of learning something new. New bootcamps for every skill, from design to user experience to product management to front and back end development, are empowering people from all walks of life to make their entré into tech. But the logic fails when we think that studying anything before was a mistake because there wasn't always a directly related vocational output on the back-end. If you study psychology and then don't work as a psychologist for 40 years is that a failure? Absolutely not. The exposure to a breadth of ideas, problem solving, complex thinking, confidence, and everything else that goes with an underlying education is exactly what makes aptitude for learning new skills quickly so facile. We ought to encourage STEM literacy and technical engagement, but rather than question the merit of everything done prior we ought to recognize that education is more holistic. My new book, The Fuzzy and the Techie: Why the Liberal Arts Will Rule the Digital World looks at how timeless and timely skills are not oppositional or mutually exclusive, why it's not a question of Liberal Arts vs. STEM, but rather how we preserve and engage the fuzzy and the techie together. To build leaders and societies, to apply our tools to intractable problems, we need people from all backgrounds and educations, learning and applying tech to their foundations.

A "Useless" Liberal Arts Degree... or Two

After spending three years of graduate school at Columbia University, where I studied everything from the history of Afghanistan to the legal aspects of U.S. foreign economic policy, I have no doubt that having more, rather than fewer, interests, has helped me in my career. In my piece for Columbia You entitled "Value of Liberal Arts, Even in Silicon Valley," I argue that this breadth of graduate exposure, on top of my undergraduate studies in political science, have only helped me see the bigger picture for how our timely technology tools can be put to more timeless use. We need more Python developers reading Pushkin, and more James Joyce scholars writing Java. More SQL queries on Salinger, and Ruby on Rails for Rushdie. More fuzzies and techies.

Arts and Humanities in our Techie World

As Laura Bradley of Vanity Fair outlines in her recent article, "What Donald Trump's Arts and Humanities Cuts Would Cost America," Big Bird is back on the proverbial chopping block... except that this time he's not, because Sesame Street already left PBS for the more well-heeled HBO. Where did all the soundbites go?

Trump has proposed cutting public funding to outlets such as the National Endowment for the Arts, National Endowment for the Humanities, and Corporation for Public Broadcasting, which funds PBS. The funding cuts would save the government a whopping 0.16% on the U.S. budget. But when government borrowing costs are significantly lower than private borrowing costs, does this privatization of public goods even make sense? It saves a paltry amount of money relative to the national debt, and the cost of capital is far lower for a government borrower than a private one to fund the same programming. But then privatization of the Arts and Humanities in Trump's case is perhaps only admitting the obvious; that someone else is better at the job than he is.

We need more investment in flexible education like the Liberal Arts, not less. We need more consideration for the cultural tools that help foster shared values in America, not less. The counterintuitive truth in our techie world is that we need more fuzzies, engineers with an appreciation for humanities, and more artists learning to code. 

"Low-Egoing" Is As Important as "Up-Skilling"

Claire Cain Miller had a great recent piece in the New York Times entitled "Why Men Don’t Want the Jobs Done Mostly by Women," highlighting how as Harvard's Larry Katz states, men have "retrospective wait unemployment." Men wait for the job they used to have. But in today's extremely fast-moving world, low-egoing is as critical as up-skilling. As General Assembly founder and sociology major Matt Brimer said in an interview for my forthcoming book, The Fuzzy and the Techie: Why the Liberal Arts Will Rule the Digital World, "your education should always in beta." In non-engineering speak, you're never done learning. We live in a world where developing a passion for continuing education, and learning to love learning is increasingly vital. While policymakers call for narrow vocational STEM training –for commendable reason with the very real skills gap that does exist in the short-run– we must also consider the longer-term implications. Creating expectations that technical literacy is the antidote to irrelevance overlooks the fact that the world is only accelerating. We need critical thinkers and learners more than ever. The Liberal Arts and STEM are not oppositional, they are mutually concurrent. We need both. We need sociologists writing Python and R, and we need engineers reading Kant.  

False Dichotomy of STEM versus Liberal Arts

The debates of Charles Percy Snow continue on over 60 years after he delivered his "Two Cultures" lecture at Cambridge University. A novelist and physicist by training, Snow lamented the growing chasm between the sciences and the humanities. Today, we still perpetuate this "either or" mentality instead of considering their mutual, concurrent benefit. Increasingly we have political scientists who are highly statistically competent, and mechanical engineers who are shrewdly versed in "design thinking." In other words, "fuzzies" are becoming more techie, and "techies" are becoming more fuzzy. Rather than label types of study as one or the other, an either or choice, we ought to be encouraging students to blend humanism and technical literacy. 

Allison Schrager in Quartz highlights research showing longer-term payout based on college major and even suggests that "Degree-specific pricing is one way to convey value to students." In other words, charge a philosophy major less and an engineering major more. The sooner we can internalize that we need our engineers to understand ethics and philosophy, and we need our english majors to understand the basics of statistics and web development, we can remedy once and for all the division between our "Two Cultures." The Liberal Arts ought to embrace STEM, and the widespread calls for STEM might also consider that knowing how to build everything, but not why we build anything, leaves us in a no better societal position. Indeed, you can do anything, fuzzy or techie. Even if you study political science or philosophy. Just look at Ben Silbermann who founded Pinterest, or Stewart Butterfield who founded Slack. They studied Political Science and Philosophy respectively. Not everyone in Silicon Valley is a "techie," nor is it the antidote.  

The Fuzzy/Techie Economist

The Economist ran a great piece on the "art and science of economics," looking at both the need for hard and soft, both methods and questions. In the era of increasing technical capacity and the need for "evidence-based" approaches, have we gone too far in considering how we prove rather than why we ask? Keynes wrote that a master economist ought to be a "mathematician, historian, statesman, philosopher," in other words both a fuzzy and a techie, but today the primacy of the techie has diminished the role of context. We spend less time understanding the political climate in which analysis is performed, and more time considering our methods of proof. The article points to Cambridge applied economics professor Hamish Low who confirms that, "Disciplines are now defined too much by methods rather than by questions." In my forthcoming book, The Fuzzy and the Techie, I argue that we need both hard and soft, methods and questions. We need rigor of approach, but also context for how and why it matters.

Finalist for FT/McKinsey Bracken Bower Prize

This week I had the honor to attend the 2016 Business Book of the Year Awards dinner at London's National Gallery. Alongside the Book of the Year award, offered annually by the Financial Times and McKinsey & Company, they offer the Bracken Bower Prize for the best business book proposal by an author under 35. Along with Igor Pejic of Austria, and Nora Rosendahl of Finland, my book proposal for The Fuzzy and the Techie: Why the Liberal Arts Will Rule the Digital World, was a Finalist for the Bracken Bower Prize, and an excerpt from the proposal was published in the Financial Times on Friday November 18, 2016. The 2016 competition for the Bracken Bower Prize featured 80 nominations from 22 countries. 

This year's FT Business Book of the Year Award went to Sebastian Mallaby for his superb and comprehensive book, The Man Who Knew, about the life and policies of Alan Greenspan.

CoverWallet Raises $7.8M Series A

Today, CoverWallet announces that it has raised a $7.8M Series A investment, led by Union Square Ventures and Index Ventures. They have raised $9.5M to date, from new and existing investors Highland Capital Partners, Two Sigma Ventures, and Founder Collective. Union Square has invested in other companies such as Twitter, LendingClub, Kickstarter, Tumblr, and Twilio. Index has invested in companies such as Slack, Dropbox, Skype, MetroMile, and Wealthfront. 

CoverWallet is reinventing how small businesses find and manage their various insurance policies, and to this end, CoverWallet has hired former CEO of online auto insurance company Goji, Jim Ermilio, who joins as President of Insurance. In addition to running Goji, he was also Executive VP and General Counsel of Commerce Insurance, which was acquired for $2.2 billion. 

John Buttrick, partner at Union Square Ventures, is also joining the Board of CoverWallet. He's led other USV investments in companies such as FundingCircle, LendingClub, RealtyShares, and SigFig, and is an immensely talented investor and advisor in the financial services sector. 

It's an incredibly exciting day to be working with Inaki and Rashmi!!

Short-Listed for the Bracken Bower Prize

I'm very excited to announce that my proposed book, The Fuzzy and the Techie, has been short-listed for the Bracken Bower Prize for the best business book proposal of 2016 for an author under the age of 35. The Prize is put forth by the Financial Times, and McKinsey, and named after two prominent figures in each respective organization, Brendan Bracken, who was Chairman of the FT from 1945 to 1958, and Marvin Bower, who was Managing Director of McKinsey from 1950 to 1967. In its first year, the Bracken Bower Prize received over 90 submissions from 33 countries. The award is presented annually along with the Financial Times and McKinsey's Book of the Year Award. This year it is in London's National Gallery, and presented by Lionel Barber of the FT, and Dominic Barton of McKinsey. 

Humans, Not Data, Failed to Predict Trump

Aaron Timms, Director of Content at PreData, authored a great piece in today's Fortune entitled "Was Donald Trump's Surprise Win a Failure of Big Data? Not Really." In the piece, he makes the great point that humans, not big data, failed us. Polling data has never been infallible, nor has it ever been predictive. Human biases shape every aspect of its framing, and its interpretation. That we "got it wrong" is not a failure of polling data, it is a failure of our interpretation of polling data. It's the pundits, not the big data, that got it wrong. It was a failure of Data Literacy in an era of Data Science. It was the primacy of the Techie over the Fuzzy, or a belief in the apotheosis of code at the expense of context. As Timms smartly argues, we must bridge this divide between human and machine, data literacy and data science, context and code, and Fuzzy and Techie. 

Race to the Bottom of the Brain Stem

Since I met Tristan Harris in 2005, he's always been a reasoned iconoclast who has stood for something. After college at Stanford, I recall seeing him with matted hair in downtown Palo Alto. He told me he'd been sleeping on floors in self-imposed hardship to keep himself focused on the most important thing at the time, which was launching his company, Apture. At Apture he sought to bring more depth and context to the web, ultimately signing up the who's who of the publishing world before selling the technology to Google in his early 20s. At Google he became a product philosopher, and began to consider the power that product designers and developers wield, and the responsibilities that come with it. "Never before in history have the decisions of a handful of designers (mostly men, white, living in SF, aged 25–35) working at 3 companies”—Google, Apple, and Facebook—“had so much impact on how millions of people around the world spend their attention … We should feel an enormous responsibility to get this right,” he says in a fantastic new Atlantic article about the importance of more humanity in our technology

We are at an inflection point where the ubiquity of our technology, and the speed with which it's impacting the far reaches of our society call for greater attention not just to how we build it, but why it matters, and how it extends and contributes to the achievement of human goals. Lest we refocus on these important issues, the habit-inducing bits of our technology in our attention economy are quickly leading to, as Tristan says, "a race to the bottom of the brain stem." 

Death of the App... Birth of New WYSISYG

As the Slack API makes writing platform specific conversational chat bots easier, and as YC churns out new companies like Prompt, making a Twilio-like Software Development Kit (SDK) that enables easy cross-platform development, there will be an explosion of conversational AIs built over the coming months not dissimilar from the Apple July 2008 App Store launch. Moreover, as Slack has developed an $80 million fund to support bots on their platform, there is a coming race for platform dominance. On April 12, Facebook will host its F8 Developer Conference, and I would suspect them to move heavily into this space as well. I suspect Facebook will launch their own SDK or app store where chat bots can be built atop Facebook Messenger, trying to pull attention away from other systems like Slack and their Slack Fund. We are at the dawn of the end of the app-era, and in the future chat-based ecosystem, what you say is what you get. 

The new WYSIWYG is here. What you say, not what you see, matters.  

The Startup Jam Session

Jam sessions used to refer to bands. Today, I often find myself in conversation with a group of entrepreneurs about "having a jam session," nailing down ideas. If startups are the new version of the band, the after-school get-together, the creative moment, then today's jam session you don't need a lead guitarist, a bassist, and a drummer. What you need is a Hacker, a Hustler, and a Designer, a techie, a business lead, and someone to help communicate the story. The backend architect holds the beat, drops the bass, and provides the drum line. The front end designer is the lead guitarist, taking you out to the edge, up the frets, and to a place you didn't see coming. The hustler helps get the band gigs, and helps you get studio time to lay down your hit tracks.

The startup jam session is the new jam session, a creative outlet for today's millennial.