We’re Running Web 2018 With Web 2008 Dashboards. And That’s a Problem.

The dashboards we look at to monitor the health of our products are lagging the experiences our user communities are having.

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Back and forth flame wars on Twitter, Facebook and elsewhere register as “engagement” and high clickthrough on “new comment” mobile notifications. As cortisol levels spike and keyboards get punched and one or more users eventually abandon the service, or feel a little angrier, or radicalize into an identity at odds with where they started out, just because that’s what makes them feel like part of a tribe.

“Time on site” and “minutes of video watched” are up-and-to-the-right indicators. More is better, caveated that we also measure “short clicks” and other indications that the user can’t find something to do or isn’t getting the right answer. But so long as they’re watching more, reading more, going deeper down the rabbit hole, that’s fine. A user eating snacks engineered to take advantage of our sweet, salty urges. Diabetes and weight gain be damned.

How did our product make you feel? Measured infrequently with user research studies, pop-up surveys, NPS questions. Next wave of startups trying to use your phone’s camera and sensors to calculate emotional response. But ahead of that we’re still flying pretty blind as product designers to understand and process the realtime emotional impact of a user experience and factor that into the algorithm. This happens slowly, often as a derivative function, as personalization understands what you seem to like or dislike, but even that is too basic and behaves like a servant, not a guardian or instructor.

Maybe the most exciting roles right now at Instagram, Facebook, Twitter, YouTube and the like are about creating the metrics of 2018 and beyond. As Jack Dorsey said, defining what is a Healthy Conversation. I’m hopeful. I want to see these sorts of metrics show up on CEO Dashboards, in Board decks, as part of the default Chartbeat implementation.

Or maybe it will be the nonprofits like the Center for Humane Technology or Mozilla that can figure this out and layer their own tools over our internet experiences using browsers and plugins to alter, slow or block the mechanics of attention vacuuming. Even forward-thinking and scrupulous teams are going to need help understanding the tradeoffs inherent in *not* maximizing for a short-term exploitive growth hack or business goal.

Keep an eye on the dashboards and analytics tools because that’s where the durable truths about an organizations priorities are depicted. And we’re still using Web 2.0 hammers to build our Web 3.0 house.

A Nutrition Label for Internet Privacy. And Apple Should Lead the Way.

WANT: a more standardized, human-readable format for conveying Privacy Policies and Terms of Service.

FDA Nutrition Labels, which were only first required within the last few decades and underwent a reformatting a couple years back, seem to be a reasonable direction to follow.


There’s a site called TOSDR (Terms of Service Didn’t Read) which tries to simplify this complexity into a summary [Wired article].

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That’s an ok start but I’d prefer to see this integrated into the products themselves versus third party destination. Apple is in a great position to drive standardization here – what if 2018 was year of the Privacy Label in the iOS App Store? Elevate this display to the same level of importance as User Reviews. Perhaps even factor into App Store ranking and promotion. Would Tim Cook go so far as to say that Apple shouldn’t promote any app that abuses user data? Of course one challenge is that even Apple doesn’t know what’s truly being done with user data.

Simplification – and notification of changes to policies in a way that updates the label, not just a bunch of legalese – is a start towards helping consumers make their own decisions about what products to use, to trust. And would aid digital literacy. [sidenote, can we stop calling it “digital literacy” – characterizing those who don’t live and breather the minutiae of tech as illiterate is *NOT* a great way to encourage learning or show respect]

So whether it’s Apple or the US Govt who takes the lead, let’s get a simplified, standardized way to present digital nutrition data.

In Living Color: Pantone’s Palette and Popular Culture

Forget “person of the year,” how about “color of the year?” #MAGA Red would definitely win for 2015 and it seems somewhat fitting that only a year before that, the blackest black possible was invented (and subsequently licensed by an artist for his exclusive use).


This NYTimes article on color king Pantone was just plain fun – filled with lush tones and genesis stories for the seminal colors of our recent history.


It’s also a business story, noting how the company has expanded their own brand into Pantone notebooks, products and even a children’s book. Seriously, this children’s book is gorgeous. No judgment if you order it for yourself!


Colors impact us in ways we’re not always conscious of – for example, pink prisons result in fewer behavioral issues for incarcerated juveniles. There’s been other research about red, blue and green offices walls being best for sales, collaboration, conflict resolution respectively. So when you go back to your office on Monday, consider what tone your tones are setting. And maybe go all Vamp?

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And When My Time Is Up, Have I Done Enough: Fred Wilson’s Post on ‘Time & Money’

Like many in the venture community, especially us newer investors, I enjoy Fred Wilson’s “process” posts, where he shares a POV on the practice of our profession. Even more than his answers, it’s his questions I find so valuable, because those questions are universally applicable while his answers might differ from my answers, just as USV and Homebrew are different. But asking myself Fred’s questions clarifies my own approach.


In his recent entry “Time and Money,” Fred covers the relationship between the two in working with, and supporting, a company. Like we do at the seed stage, USV almost always plays the role of “lead investor.”

He writes: “Time is a valuable resource for all parties and it should be a factor that both sides include in the deal making analysis. But it often is not.”

And later: “The truth about these situations is a few seed investors will massively over deliver and the rest will massively disappoint.”

And finally: “If one has time to evaluate the time commitment issue as part of an investment process, it becomes a bit easier for both sides to get this right. A rushed financing makes it harder and can lead to miscalculations on both sides.”

All of this resonates with me and I see it every day in our deal-making and deal-servicing. How we wanted to spend our time was actually one of the very first things that Satya and I discussed because we believe multiple fund model decisions flow from that clarity.

  • We spend 51%+ of our time with our current portfolio – that’s what it takes to deliver against our commitments to the founders we’ve backed, and they are always our priority. I’m suspect of any early stage lead investor who isn’t willing or interested to spend the majority of their time with their companies (even though I see them pretty frequently in the market). It also means we don’t invest in people we don’t want to spend time with, even if it could be a profitable investment.


  • Invest at the seed but don’t disappear at the A – we continue leaning in to support a company operationally until at least the Series B (this includes sitting on their Board, setting aside weekly/biweekly time to help them and their management team, riding the ups and downs with them to help the CEO grow as the longterm leader of the startup). After that milestone we move from the Board Room to speed dial since we know the company quite well by then and they have a Series A and Series B investor at the table. We’re not a “stay on the Board until the end” firm but we are atypical for seed stage funds who more typically don’t take Board responsibilities and step off at the A.

Some venture friends goodnaturedly tell us we work too hard for our ownership (or maybe more specifically too long, since we don’t just pass the company to the Series A lead and say “good luck”). For us that’s a feature, not a bug – we really enjoy getting these startups to a stable foundation, enjoy seeing them scale and grow. And because it benefits them, we believe it’ll payoff in our returns and reputation.

  • We spend time on investments where we won’t make money – this isn’t unique. Almost all of the investors whom we respect *will* throw “good time after bad” because it’s the responsibility they have to the founders, because helping a company land for a .5x-2x return can help a portfolio vs just taking a 0x, and because it’s where you earn the reputation that will help get you into the next 100x opportunity. So like Fred says is his post, you try to judge how much time you can or should spend on an investment but there’s always a floor above 0, no matter how hard the situation has become.

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Your fund can be any size but your time is limited by physics. Being intentional about how you commit it over multiple years and multiple companies is ultimately more important than ownership targets, reserve ratios or carry structure. And if you start with a service mentality – that your primary obligations are to your founders – you’re starting off with a pretty good true north.


The SF Scooter Wars & Proposal for Urban Safe Harbor Zones

In case you haven’t heard, civil war broke out in San Francisco last month, and it’s over dockless scooters. Battery-powered single-rider scooters which can be signed out using a mobile app and then left wherever the rider disembarks. The economics only work when you’ve got a density of riders so multiple companies descended on San Francisco, each hoping to beat the other in a landgrab. My understanding is that most (all?) of them launched without any particular outreach to SF city government, preferring to take an “ask for forgiveness” approach given that (a) they’re not illegal, (b) regulatory impact falls between multiple agencies and (c) venture-backed startups live and die on growth.

[*since publishing, one person reached out to say at least two of the scooter companies reached out to one of the city departments pre-launch and got implicit ok. I don’t have details to confirm one way or the other.]


So what happened? Like pigeons these scooters flocked, creating at best a visual detritus, and, at worst, blocking doors, sidewalks, disability accessibility and so on. The scooter companies insisted this was the riders’ fault – their apps clearly say to park the vehicles out of the way and to not ride on sidewalks. And shortly social media, tech blog and local politicians were all making noise about our city’s latest transportation option.

I fell into the camp of “ugh,” at least with regards to the clumsy launch that shoved all of the usage externalities on to non-riders. When they blocked my way I *gently* pushed them aside with a kick, and I hungered for a creative street art stickering project to turn Lime into SLime and Bird into Turd.

At the same time, it’s clear these scooters – or something like them – will be part of our future urban landscape. They make sense, are fun to ride and will be a puzzle piece in solving sprawl. So the companies are likely to go through some back and forth with the city before everyone arrives at some sort of productive conclusion.

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But what could entrepreneurs and regulators take away from this spat? Should every urban startup go through an approval process just to operate (separate from business licensing, etc)? That sounds horrible and overreaching. And would also favor deep pocketed companies who post-launch would gladly support new regulations as a way of keeping potential additional entrants at bay. On the other hand, the “simply ask forgiveness” playbook sure feels very 2014 and out of step with where we want our tech values to settle post-bro.

What if city officials created a type of “Urban Startup Safe Harbor” where new products could be trialed for a limited period of time over a particular density. Startups would agree to proactively “file notice” of a test and share resulting data with the city. All tests are approved on an opt-out basis. That is, if the public official overseeing the Safe Harbor initiative has concerns, they can block the test but a judge will review the materials and rule within a few business days. The test can stay private for up to 28 days or so, after which the basic information will be made public by the city.

I’ve lived in SF for 20 years and am now raising a family within its boundaries. There are a host of growth challenges facing this town and technology companies need to be part of the solution. Not just by creating jobs but by coming to the table and building frameworks and transparency that take all citizens into account.

The Empty Chair at the Table During Meetings: Who Should Be In The Room That Isn’t

When you sit at a management meeting are you representing yourself or someone who isn’t in the room? I was recently chatting with a startup CTO, who recently joined his company’s Board, about the responsibilities of being a Director. That it’s not a role about advocating for your own interests but instead trying to make the best decisions on behalf of the company. There’s a great passage about this from a podcast with USV’s Fred Wilson and Reboot’s Jerry Colonna:

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I also recently came across another variation of this “who isn’t in the room” metaphor in a conversation Greylock’s Reid Hoffman had with Starbucks’ Howard Schultz.

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I really like these ideas as guardrails to make sure that as individuals and as groups, you’re not making decisions that run in opposition – strategically or ethically – to the constituencies which aren’t – or can’t be – represented in management conversations.

For VCs, Your Thesis Is Your Portfolio Page, Everything Else is Just Hopes and Dreams

“We invest in rebellious outliers.” “We invest in the Future of Work.” “We invest in frontier technologies.” “We invest in diverse founders.” “We invest with social good in mind.”

I hear, read, see examples every day of investors espousing differentiated theses with regards to why they exist. Why a founder should take their dollars. And why a LP should give them theirs. Sometimes there’s substance behind these statements; others are rickety content marketing or breathless trend hopping. Fortunately there’s a source of eventual truth! Your portfolio page. Your portfolio page is your thesis. It’s where you’ve committed dollars, not just Medium posts. It’s who has actually taken your checks, not the deals you wish you were in.

One challenge for seed investors especially is that your portfolio page is a lagging indicator of your interests. Startups often don’t announce their initial funding for quarters or years, which leads to the “oh I didn’t know you guys invested in that area” challenge for early funds like ours.

So we network, we write blog posts, we research, we tweet. And hope to continue adding amazing companies to our portfolio page. Because the portfolio page is real.


Photo by abigail low on Unsplash

YouTube Lets People Decide Their Own Truths – And That Was Once a Good Thing

The most intense week of my life occurred in the spring of 2009. A small group of tech folks were in Baghdad – and not just the Green Zone. We traveled across the city to meet with government, military, NGOs, professors and students. It was the kids who made the most impact upon me, specifically a 17 year old girl. I still remember what she told me about YouTube, where I was running product at the time.

She was very thankful for YouTube. First, because it made her feel connected to other teenagers across the world. She saw that even though her circumstances were quite crazy, that at a human level she was no different than a boy in Tokyo, or a girl in San Paolo. Friends, parents, school, crushes. YouTube turned her into a global citizen.

Second, she told me that YouTube was valuable because it allowed her to develop her own sense of the truth. She’d grown up in a repressive regime that historically limited her access to information. But YouTube provided her with first-person perspectives, citizen journalism that captured what was really taking place in her country. And news clips from around the world to add context to the explosions she heard nightly.

Nine years later we look at platforms like YouTube and wonder whether the “truths” they’re telling are really lies. Conspiracy theories, divisive content, deceptively edited video which is a minority of the content on the site, but exacerbated by algorithms, engagement and our own temperaments. All significant problems to be sure and these companies will be judged ultimately by their ability to adapt to these new understandings. But I hope we can still create global citizens and I hope we can still empower people to develop their own sense of truth. My Iraqi friend would be 25 now. I wonder if she’s still in Baghdad or did she move far away. I wish I could talk to her again. I hope she’s ok.


Photo by Jay Wennington on Unsplash


Giving Visionary Women Their Due

Even though I finished reading Emily Chang’s Brotopia last month, it’s lingered. One passage in particular — Jennifer Hyman, CEO of Rent the Runway, talking about how we call many men in tech “visionary” but fail to apply this characteristic as often (or at all) to women.

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Reflecting on Jennifer’s assertion, I thought of our experience with theSkimm, one of the most dynamic audience companies out there today and a startup we were fortunate to first back in 2013. While reading Brotopia, we were also helping theSkimm finish up their new financing, with Google Ventures and Spanx founder Sara Blakely joining the cap table. Over the past five years, I’ve witnessed theSkimm be underestimated by the venture capital industry, by pundits and press. During that time I’ve heard many male media founders lauded as “visionary” – Jonah Peretti, Shane Smith, Bill Simmons. They certainly deserve it. I’ve rarely heard Carly Zakin and Danielle Weisberg described the same way. They deserve it too.

“Visionary” is defined as “thinking about or planning the future with imagination or wisdom.” What, in my mind, makes them visionary when it comes to theSkimm?

  1. Email as Format – at a time when they were being told to just try and grow on the back of Facebook and other social platform, they took a medium decried as moribund and reignited it.
  2. Smart Summarization as Wedge – helping make it easier to live smarter. Taking real news – not women’s news – and delivering it in a branded tone.
  3. Leveraging 1% Fans – the Skimmbassadors as a group, now 30,000 strong, which helps drive the passion and provides a realtime focus group.
  4. Paid App – One of Apple’s Top Five Highest Grossing News Apps since the day it launched. A $2.99/mth product delivering a seven-figure revenue stream… and growing.
  5. Calendar Integration – The app integrates into your calendar and posts things coming up you need to know about – ranging from entertainment and lifestyle events, to activism and political deadlines.

Some of this ground was completely new to the industry. Some was shared by similar thinkers such as Mike Allen and The Week. But the package is unique. And that’s why 7+ million active readers start their day with theSkimm. A number that’s almost all US-based, professional and aspiring professional. A number that’s the equivalent of a Top Five news network.

Digiday recently did a podcast with Carly and Danielle and it’s a lively snapshot of how they think about the present and the future of theSkimm (transcript). Listening to it I thought one thing – visionary.

Congrats to the team on their fundraise and here’s to being underestimated!