JDR’s Newsletter – #10

Hello there,

This is a (roughly) weekly newsletter experiment containing links to things I’ve written and made, plus links to other interesting articles, reports and essays I’ve come across.

In case you haven’t already subscribed, you can do so through Tinyletter. You can find an archive of this and previous issues of my newsletter at news.jdr.fyi.

Thoughts, opinions and typos are my own.

My blog posts and articles

This week I wrote two articles for the Mattermark blog.

Series A Rounds Slip In Q2 As Dollar Volume And Deal Velocity Recede (Mattermark)

In line with the title, I find that Series A investing has slowed down significantly in Q2 of 2016 as compared to Q1, both in terms of dollar volume and the number of deals struck.

However, despite this, I also found that the median Series A round size remains basically unchanged since 2014, meaning that the fundamentals of the market for Series A-stage equity remain as strong as they were in the good ol’ days. However, this may change a bit.

Making Sense of Why Series A Investment Is Slowing (Mattermark)

In this post I try to make sense of the declines I identified in the first one. I cite global macroeconomic uncertainty as a likely cause of the slowdown in startup investing, while also delving a little deeper into the historical data on Series A investment over time. (i.e. If you want to see some nice longitudinal charts, this is the post to read.)

On The “Blanding” of Web & Mobile Design: Some Light Reading (jasondrowley.com)

Here I provide some really brief background on “flat” design and links to a couple of interesting articles. I suggest reading Charles Thaxton’s “Whither The Webpage” if you’re not going to click through to look at the other resources.

Against life hacks

Laurie Penny’s critique of life hacks and guilt-inducing “wellbeing ideology” for The Baffler is delightfully (or, depending on your disposition toward this sort of thing, depressingly) caustic but ultimately redeeming. She asserts that the Instagram photos of kale smoothies, post-workout selfies and self-congratulatory proclamations about mindfulness and spirituality is a symptom of a broader social disease, but ultimately ends up echoing the ideas David Foster Wallace touched on in his Kenyon commencement speech, “This is Water” (a full audio recording of which can be found here). The path toward sustainable wellness is not paved with yoga mats and washed with asparagus water, but found in the more quotidian and humdrum activities we perform, like getting out of bed every day to do something that furthers our goals and makes the world a slightly better place.

Other news and links

Best of

DuckDuckGo CEO & founder Gabriel Weinberg posted a list of dozens of mental models he repeatedly finds useful on Medium. The list is incredibly helpful if you’re looking to expand your cognitive toolbox, or to brush up on concepts that you’re a bit rusty on. Weinberg even included a how-to guide for using the list and links each concept to more resources (usually Wikipedia but often to blog content and essays from elsewhere).

Tech industry news & commentary

If you liked the pieces I wrote for Mattermark this week, you should check out Elad Gil’s post, “End of Cycle?” In it, he provides contrasting interpretations of the bloom in variety of companies that are receiving funding from VCs. On the one hand, it could mean that lots of industries are ripe for takeovers by tech companies, but on the other, it could just be a signal of desperation by investors thirsting for the next new thing. There’s a lot more in there, but I don’t want to bury the lede.

Bitcoin’s block reward halved on Saturday, meaning that every ten minutes, half as many bitcoins now enter circulation (12.5 bitcoins now) as compared to, say, Friday and the few previous years. This caused a significant spike in Bitcoin’s exchange rate over the past month or so. But, for one brief moment, Bitcoin was a less volatile currency than the post-Brexit British Pound.

Nieman Lab covers Audible’s rollout of Channels, its new mobile application that features curated audio content in, well, channels like “The Daily Rush”. This appears to be Audible’s first serious foray into the podcasting space, and it will be interesting to see whether its original content is attractive enough to get new subscribers for the Amazon-owned service.

bobg of Lab41 – the interdisciplinary lab in which the US’s intelligence agencies come together to discuss and work on problems related to Big Data – explains why there is a need for a a bullshit detector in conversations about artificial intelligence.

Maybe bobg should read Stephen Merity’s article, “It’s ML, not magic: simple questions you should ask to help reduce AI hype”, which was posted on July 3rd.

This week, The Atlantic revisited a January 2016 analysis from the Wall Street Journal which found that despite Millennials’ celebration of entrepreneurship and startup culture, business ownership by the under–30 set in the US is at a 25-year low. Derek Thomson, the Atlantic journalist behind the piece, concludes that student debt and reduced risk appetite among young people is to blame, but that there are also some bright spots.

In a breezy but informative post, Nidhi Shah explores the evolution of mobile application design from 1994 through 2016 for Growthbug. Major highlights include the lexical shift from “features” to “apps”, the simple but functionality-rich apps of the pre-smartphone era, Apple’s release of the iPhone and App Store and Google’s rollout of Android and Google Play stores, and the evolution of the mobile app and mobile game businesses. Worth checking out if you want a refresher.

Other design stuff

In a time when AI and “conversational UIs” are all the rage, Intercom published their 8 principles of bot design. Among them are the following guidelines: “Don’t pretend to be a human”, “Use [bot] interactions sparingly”, and “provide an escape hatch” (e.g. a human fallback) for when conversation between human and bot inevitably breaks down. (For a case study of good bot design, I recommend checking out X.ai, a scheduling bot I frequently use.)

UCLA designer Perre DiCarlo believes – and proves – that porting paper forms to the web is more complicated than copying and pasting. This is one of the most meticulous case studies of web form design I’ve seen yet.

JDR’s Newsletter – #8

Hello there,

This is a (roughly) weekly newsletter experiment containing links to things I’ve written and made, plus links to other interesting articles, reports and essays I’ve come across.

In case you haven’t already subscribed, you can do so through Tinyletter. You can find an archive of this and previous issues of my newsletter at news.jdr.fyi.

Thoughts, opinions and typos are my own.


My blog posts and articles

A Beginner’s Guide To VC (Mattermark)

This week, I compiled a list of some of the best resources I’ve used to learn about the venture capital industry over the past couple of years. It contains over 60 links to books, academic articles, explanations of common terminology and a list of influential VC blogs and podcasts. If there is anything that I may have left out, please let me know and I’ll be sure to add it if it’s a good fit.

3 Places To Start Learning About Marketplace Businesses (jasondrowley.com)

After the Mattermark piece, I received a lot of requests to provide resources on specific industry verticals. In what’s probably going to be an occasional series on my blog, I start with marketplace businesses. Here, I identify my essential list of readings from Version One Ventures, Benchmark’s Bill Gurley and product maestro Rishi Dean, all of which provide their own analytical frameworks for understanding and evaluating marketplace businesses.

Notes on Twilio, Line, and the Open (?) Window (jasondrowley.com)

On Thursday, Twilio, the cloud communications company, made its public debut on the NYSE. And boy what a debut it was. Priced at $15, opening at $23.99 and closing nearly 90% above its IPO price, investors from Sand Hill Road to Wall Street may feel tempted to proclaim the tech IPO window is open. 🎉 But as I point out in this post, one data point does not a trend make, and the next company on the IPO docket, Line, may curb some of that enthusiasm.

Brexit: History, Market Failure, Threat (jasondrowley.com)

Thursday’s vote for the United Kingdom to exit the European Union was certainly interesting. It’s tragic for some, and a point of elation for others… exactly what you’d expect from a highly contentious referendum. To me, though, the most interesting aspects of Brexit is the failure of prediction markets to anticipate the outcome and the impact the move may have on the scientific and tech communities in the UK and EU going forward. In this brief post, I share some of the best analysis of the prediction markets and science stories that I could find.

Other Tech News

Boston Dynamics Debuts SpotMini

Robotics company Boston Dynamics unveiled their new model, SpotMini in a Youtube video on Thursday. This smaller, nimbler successor to Big Dog and other models moves even more smoothly and has an attachable “neck” that can be held stable in space as the body moves around it. The unit in the video has a (presumably detachable) neck with a “mouth” that can grasp and manipulate delicate objects, but this mouth module could presumably be replaced by a camera or other sensor array. We’re definitely creeping into Uncanny Valley territory here.

After watching the SpotMini video, you might want to read this essay about the Uncanny Valley from n+1.

Elon Musk’s Company Bids For Elon Musk’s Company

In a move that would make even the best due diligence team die a little, Elon Musk’s Tesla announced a bid to acquire green energy installation company Solar City, of which Elon Musk is largest shareholder. Remember that Tesla is trying to expand its network of car battery charging stations and expand its “Power Wall” battery business, so the missions of the two companies are well aligned. This would move Tesla further down the road toward becoming the generalized energy infrastructure company it aims to be, if and only if SolarCity shareholders, Tesla shareholders, and in all likelihood some court feels as though there’s no conflict of interest here.


Other news and links

Best Of

Like most Chicagoans, I like giardiniera, the spicy mixture of pickled veggies and hot peppers usually served with Italian beef sandwiches. I made a batch using this recipe and it is diabolically good.

Patrick van Hoof published a guide to AI for designers. And, while on the subject of AI, it might be fun to check out The Scientific American’s reporting on Facebook’s AI and machine learning efforts. The piece goes into significantly more detail than reporting in the big tech press.

Tech Trends & Industry Commentary

In an essay on Medium, software engineer Laura Montoya helps to unpack the tension between diversity and “cultural fit” in the tech business.

Leigh Honeywell’s post about the problem of “rock stars” in the tech business is amazing. If you’re reading this, you’ve probably seen an a job listing or heard someone describe someone as a “rock star [developer/designer/sales person]”. According to Honeywell, a senior staff security engineer at Slack, this sort of characterization breeds the culture of narcissism and arrogance that tech is known for and even celebrates. I agree, and you should read her post.

It turns out that Uber drivers don’t make a lot of money, according to reporting on leaked internal data by Buzzfeed’s Caroline Donovan, but that shouldn’t have surprised anyone. Average wages: less than $13.25 per hour.

JDR’s Newsletter – #2

Hello there,

This is a (roughly) weekly newsletter experiment containing links to things I’ve written and made, plus links to other interesting articles, reports and essays I’ve come across.

In case you haven’t already subscribed, you can do so through Tinyletter. You can find an archive of this and previous issues of my newsletter at news.jdr.fyi.

Thoughts, opinions and typos are solely my own.

My blog posts and articles

VCs Spark High Times for American Cannabis (mattermark.com)

In my latest post for Mattermark I interviewed a number of folks operating in the rapidly-growing legal cannabis space. Driven by continued legalization for medical and recreational use, both entrepreneurs and investors are looking to capitalize on what some analysts believe could be a $100 billion market within the next decade. Special thanks to Ben Larson, co-founder of Oakland’s Gateway Incubator, and Keith McCarty, founder and CEO of Eaze, for speaking with me.

Recent Observations From Other People

Chris Dixon on bundling and the internet economic loop

The most recent post from Andreessen Horowitz partner Chris Dixon asserts that market and technical conditions are such that big companies are re-bundling (or vertically integrating) services. He cites competition as a key driver of this bundling phenomenon and presents a range of events and trends that may serve as nucleation points for further bundling activity.

(For the record, this is a textbook example of what institutional theorists DiMaggio and Powell call “structural isomorphism” in response to competition. Their 1983 paper is deftly summarized here.)

Mandy Brown on bots

In her latest letter on ro/text/chat bots, designer and media observer Mandy Brown highlights some potentially unsettling trends in the current surge in AI-enabled digital assistants. First, Brown brings up the issue of opacity in some of these interfaces. Unlike more transactionally designed user experiences that offer both textual and visual interaction models, such as Apple’s Siri, it’s more difficult to know where a bot sourced the information it serves as an authoritative answer to a user’s query. This is especially troublesome in interaction models that use solely the spoken word (such as Amazon Echo) or “secondary orality” (text that works like spoken language) such as the messaging-inspired interface of a service like Magic.

Second, Brown cites the caretaker/servant role AI has taken in science fiction and our lives today. Since many AIs are branded with female voices or names – Amazon’s Alexa, Apple’s Siri, and X.ai’s scheduling assistant Amy, all come to mind – Brown argues that this positioning “reveals the expectation that a generation of woman-gendered bots are being created to serve the needs of men.” Regardless of your stance, the gender issue Brown has called attention to is one that designers, engineers and marketers will have to be mindful of going forward.

William Storage on multidisciplinary thinking

In his contribution to an anthology of blog posts, books and academic articles promoting the benefits of multidisciplinary teams and polymathic people, Bill Storage traces the role of multidisciplinary thinking in the process of invention and innovation. He spends a good part of his post rehashing some of the core ideas of this school of thinking. He explains the strength of specialization in fields like research through expanding human knowledge in a depth-first fashion, but he also states that innovation happens when expertise in multiple fields overlaps and collides with one another.

Although what Storage says is not groundbreaking from a theoretical or academic standpoint, it serves as a reference to some good case studies, quotes and anecdotes, as well as validation to those who’ve chosen the more interdisciplinary path.

Podcast episodes of the week

“The Importance of Research” and “Choose Your Own (Negotiation) Adventure” from Nick Disabato and Kai Davis’s self-styled “crappy business podcast”, Make Money Online are two of the most informative podcast episodes I listened to in the last week. Although the advice and subject matter discussed in Make Money Online is geared toward independent consultants, contractors and other itinerantly employed folks, each episode has some strategic nugget that anyone can use.

Other news and links

Mandy Brown’s other writing, specifically her Letters section, is incredibly thoughtful

Square’s Q1 miss may not bode well for IPO hopes of other services with low margins

Julie Zhuo’s “Design, Illustrated in Three Charts”

Anthony Bourdain’s post about his visit to Chicago

Buzzfeed takes a deep dive into some leaked internal documents from Palantir, Silicon Valley’s [most secretive company”

Old but good: A brief history of venture capital and the investors who invest in the VCs on Venture Hacks (2010)

Vanity Fair calls out the tech press for not doing their diligence on Theranos

Y Combinator publishes startup trend analysis from its massive longitudinal dataset of applying startups in their longform blog, The Macro

A scientific look at why whiskey cannot be made to seem older than it actually is