Visual Technologies: No Longer Optional

Each year, a small set of technologies graduate from academia and hackerdom to the real world. Most recently, chatbots, VR, 3d scanning, drones and visual object recognition have earned their mortarboards.

For investors, founders, technologists and artists it is critically important to keep tabs on what’s graduating and when optimally to begin experimenting with new technologies or novel approaches to old problems.

And therefore it is important to know where to look. Every day we are inundated with tech news, investor news, M&A news. But where do you go, online or IRL for clarity in where things are and where they are headed? In fact, the most inspiring people I know dedicate a material chunk of their attention to constantly honing their sources on inspiration and information. I try to do the same.

There are a handful of great meetups and conferences that achieve an elusive marriage of science, enterprise and pragmatic application. Finding them, participating in their communities and molding your learnings into tangible business and creative products is something I spend a fair amount of time on.

At my company, Kontor visual technologies are an essential part of the service we build for architects and designers. Our customers thrive on our constant improvements in image search and content presentation. We keep our eyes on what’s next in 3d modeling, VR, AR, image intelligence and many other areas. And to do that, we seek venues and networking opportunities to learn and share.

In 2016 I’d venture to say that no matter what you are building, visual technologies need to be part of your (ahem) vision. Immersive experiences must be part of any media offering. Visual intelligence must be part of any smart platform. Hardware and software businesses have to be current on what’s possible and what’s on the verge of possibility.

It’s my privilege to be involved again this year in the LDV Vision Summit, as I have been since its inception. Its founder, Evan Nisselson of LDV Capital, brings together startups, innovative big companies and a host of individuals who are driving visual technologies forward at a breakneck pace, all with a grounding in pragmatism and cooperative learning about what the near future holds. This event gets better every year; if you are reading this and able to get to NYC next week, you most certainly should attend. Join us and tell me about your predictions for the near future and what you are doing about them.

(cross-posted on Medium)

Roadmapping to Nowhere

(with Jennifer Gormley)

Product roadmap meetings — here’s the ideal: You and four other people cram into a small conference room that’s also stuffed with Post-it notes, whiteboards, and maybe even a slide deck. The scent of dry erase markers hangs in the air. It’s the fragrance of promise, a bouquet of hope. The idea is to come up with a plan for what the team is going to build in the next couple of quarters. A clean, prioritized list with strong consensus behind it. Ideas flow freely and fall into place like they were sent down from upon high.

Now, here’s the reality: You say, “We’ve got 37 great feature ideas to run through and plot out against our dev resources, user needs, and product vision. We need to explain to the board why we’re doing what we’re doing and stick to the plan. So I think the best way to…” and then everyone in the room interrupts you at the same time:

The Engineer: “Uhhh, yeah. We don’t really have any resources available with all these bugs the designers are flagging. Seriously, I can’t put it on a half pixel.”

The Designer: “If you’re going to tell me again we can’t do Feature 19 — that animated kitten gif for the users who get on the leaderboard — then I don’t really need to be here. And you all know I like blue, so make all the new features blue.”

The CFO: “He’s right. We don’t have any resources — since they are mostly playing
foosball in the lobby…”

The CEO: “Well, I’ve already sold Features 35, 36, 12, and eight to our new client in my last meeting with them, so those go to the top of the list…. And I have 2 more to add that their secretary’s cousin thought would be cool…. But of course we can do those after the four I just listed get finished in Q1. I can be reasonable.”

The onslaught draws a sigh out of you as you wonder if it is okay to drink at 10:17 am. As you uncap a marker and pass the sticky notes around, it’s clear that this effort failed before you all even squeezed into the room.

Product Design is fraught with best guesses, good ideas nestled among complex bad ones, and tenuous relationships with distant, sometimes theoretical users. Product roadmapping sessions are a strange mix of passion, interpersonal influence, poor planning, and misdirected energies. We’ve been in what must be hundreds of product meetings, and come up with one universal truth: Product Design = Hard. There’s no getting around that. Creating product roadmaps, however, well that can be easy. Seriously. Easy.

Recently, we faced the challenge of road mapping exactly 37 features with a new team. We didn’t want to make the same mistakes we had each made with previous teams, which almost always went like the example above. With this new team, we had just launched v1.0 of the product together. And remarkably, we all still liked each other. We even felt good about moving to the next phase; our product was in the market and feedback was coming in, mostly positive.

We looked at the blank sheet of paper upon where next year’s plan was about to unfold, and we thought: instead of tackling things the usual way, let’s take the personal passions out of it. Questions immediately clouded the way. This time, can we make — with a new, unsullied team — a less contentious, more productive, and more confident (team wide) roadmap? Could we filter out personal biases and focus only on goals (for our company, for our users, for our bottom line)? What basic math would result in a non-controversial, prioritized list to tackle with available resources? And could we use the list to make smart choices about spending more on developers, with quantifiable market impact?

Hell yeah, we could — and it actually works.

We considered 5 key perspectives:

  • Market Perception: Are we a leader? Do we have feature parity with others?
  • Cost Savings: Does the feature make things more efficient for internal ops? Solve technical debt that is becoming costly?
  • Key Vertical Differentiator: Does the feature clearly distinguish us among competitors?
  • End User UX Perception: How great is the UX for the bulk of our users?
  • Administrator UX Perception: How great is the UX for our purchase decision makers?

…and one overarching key driver:

  • Revenue Generation Potential: Obvs.

We began by asking the senior subject matter expert in relevant departments to rate each of the 37 features from the perspective of their team. These ratings were done based only on the title and brief description of the feature, because we didn’t want to spend a lot of time building specs or wireframes at this early stage. Ratings were done on a scale of 1–5 (with one being little to no potential impact, and five being high to “we better do it or else” potential impact). They did this in a vacuum. That is, no one knew how the others were rating things.

The benefit of this blind rating, done only in one’s area of focus, is that no one is influenced by the others’ numbers. Groupthink becomes negligible, and features which might otherwise overlap on a feature/value matrix begin to come into stark contrast with one another. When we reassembled to look at the features and their ratings as a group, it was clear something remarkable was happening. We’d cleared away all the extraneous debate and laid bare the priorities our collective brain deemed most critical to work on. Magic — or is it math?

Our Mathematics of Roadmapping:

For each feature we calculate a “Feature Score” (FS) as:

FS = (average of perspective scores) x (revenue generation score/5)

The first multiplier is a simple average of all the perspectives, each equally weighted. The second term overlays revenue on a normalized basis. By “normalize,” we mean we divide the revenue rating by the number of possible points so it’s value is never greater than 1. In this way, revenue can significantly boost or limit the FS but its impact doesn’t overshadow the average of the feature perspectives. Let’s take this for a spin.


  • Feature 1: “Improve User Registration” had an average score of 2.6 and a revenue score of 5, giving it a 2.6 FS
  • Feature 2: “Real-time Chat” had an average score of 1.2 and a revenue score of 1, giving it a 0.24 FS
  • Feature 3: “Offline Sync for Native Mobile Apps” had an average score of 2 and a revenue score of 3, giving it a 1.2 FS

By normalizing the revenue generation score (n/5) we can see the subtle variations in priority among all the features. Although the CTO wouldn’t have rated user registration improvements as a high-priority project, a balanced perspective shows it to be very important to take on. We have seen that natural patterns and affinities begin to emerge, like a focus on collaboration tool features, or on internal content authoring efficiencies. These roll up into easier market discussions, client pitches, and board reviews of the company vision.

This also works well when thinking about “themed” releases. If, for example, the next major market release has a “social” theme, the team can filter out features that don’t fit “social,” and then conduct the exercise. The result will be a prioritized set of projects that accomplish the theme.

Our approach has worked well for small teams, particularly so for startups. They tend to be constantly responding to changing priorities and moving targets, yet they need a roadmap to guide 3–6 months worth of development. For larger teams, it’s likely that more complex math, a different approach to averages, or laying in additional team perspectives would be more suitable. The inputs are not one-size-fits-all, but we think this technique is, and we urge you to try it. This alone isn’t a recipe for product success, but it might just save your team’s sanity, and get you a roadmap everyone believes in.

So, instead of the contentious clamor described earlier, imagine a quiet afternoon plugging in the data from your team. They provide accurate scores from their perspectives quickly and easily. You save hours avoiding the hair-pulling, passionate, but unproductive debates that devolve into eye-rolls over the designer’s animated cat gif. You come together to review the early plotting with a sense of order already on the table, making roadmapping actually easy.

When it comes to imagining and building great products, we wouldn’t trade the passion of startup teams for anything. And any tool or process that converts those strong feelings into a viable plan — or working code — is a great thing. So, in your next product roadmap session, give this math a chance. It takes the passion out of the planning and puts it where it belongs — into the work. Now stop sniffing those whiteboard markers and get to it.

Living Room UX, not SUX

The Web is abuzz this week with anticipation of the upcoming Apple Television rollout and how it’s going to revolutionize the way we interact with television programming from the couch.

While I agree that’s going to happen, I think the reasons are not as intuitive as the analysts believe. Apple isn’t going to do something we haven’t seen before, at least not yet. And, the living room TV content revolution has largely already happened.

Cable TV is a giant set of brotherly monopolies in the US. As Henry Blodgett points out, there is a history lesson to be taken from the fate of the newspaper industry. But that’s already an old story-  what the market wants is on-demand content with a great user experience (UX). It’s sad and infuriating that there is no competition in unified set top boxes or a way to accomplish delivery of all TV content. I’d pay for this, and so might you. For years innovation in television UX has taken a back seat to everything else in television while every other manner of consumer device has benefitted from faster hardware and smart interaction design. But how revolutionary can entrepreneurs be when the very core of the content ecosystem is locked? Just ask Boxee, Logitech, Roku and many others. Consumers have a binary choice: deal with crappy cable boxes or “cut the cord.”  More and more are cutting the cord. And getting everything they need from their screens.

So Apple can’t solve this. But- if they have partnered with cable providers as the swirling rumor mill supposes, Apple will be able to bring a decent user experience to television, in a way that the $99 Apple TV in my living room fails to do. Google failed at this marginally, too. Cable company set top boxes fail at it spectacularly.

One has to wonder who is responsible for cable box UX in OEM deals with Cablevision and Time Warner. Are they given shoddy second-hand hardware to work with? Terrible design teams? A mandate to frustrate their end users? Perhaps a crash quota of 2 kernel panics per week? Craziness, right? And yet, this is how much cable company television user interfaces suck.

If it takes the magical shimmer of Apple’s Television to break free, so be it. Apple doesn’t need to do more than provide a decent, modern touch-friendly experience to push the cable guys out of the UI business forever. But let’s hope and do our best to ensure that we don’t trade a bunch of regional monopolies for an international one. Give TV consumers a choice of great UX’s from which to choose, and I think they will continue to pay for cable subscriptions and suffer the advertising that makes the whole think tick. At least for a while.

Bring on great living room experiences powered by innovators who care about responsiveness, intuitive design, and have studied the art of user experience. Give me UX, not SUX.

PyCon 2012

I am excited to be in Santa Clara this week for company business and for PyCon 2012.

In recent years I have seen a tremendous lift in the size of the Python community and the innovation coming out of it, and I am thrilled to be a part of it. On Sunday I’m giving a “poster” presentation on this very topic; I’ll be engaging with the community here on why a Python-based stack is the right fit for our efforts at my new startup, Happify.

Beyond the obvious energy and creativity coming out of Python, my thesis is that NYC is becoming a center of great Python work in startups. Thanks to open-source frameworks like, a growing talent pool of xooglers and Bay-area expats, and the sheer number of funded early-stage companies embracing Python (for it’s readability, productivity/fun, and good-enough performance), it is a natural and solid choice for NYC startup efforts. I am jazzed about becoming more involved with the NYC Python scene and contributing wherever I can.

If you are at PyCon, please say hi. I’ll post about my experience here when I am back in NYC.


Looking back over the few posts on this dusty old blog, I’m amused and chagrined to see that I’ve mostly written about leaving old opportunities to pursue new ones. And here I am writing that post once again. But this year I’ll be writing more here.

I spent 2010/2011 building the technology platform and team at Bookish, and it was an amazing experience. But, for me it came to an end. I miss the team and the irreverent vision we shared, and the inspiration it brought me. As is always the case, ideas are cheap, money is out there and the hardest part is surrounding yourself with the right set of amazing collaborators.

Last year was busy.

  • We worked our butts off on Bookish.
  • I started the NYC SproutCore meetup and hosted several events.
  • I pursued speaking more aggressively, notably at MySQL Conf and Surge.
  • I was quoted in the WSJ and featured on GigOM with a headline that included the words “Harsh Mistress.”
  • I mentored at SeedCamp NYC and IBM SmartCamp.
  • I wrote a bunch of code outside of work and learned some new stacks and tools for the hell of it.
  • I got pretty excited about these wind synthesizer patches and wrote some music, soon to be released into the wild I think. I was quoted on the developer’s site.
  • I kept off the 15 pounds I lost in March.
  • I learned a LOT.

But there are a lot of things I didn’t do. I didn’t play or write enough music. And although I talked about it a lot and was on the scene, I didn’t found a company. Well, not until mid-December, so that doesn’t count.

So in 2012 I’ll do both those things, and write about my experiences here at least 12 times. I hope you’ll read and comment. Happy New Year!

Moving on to My Next Big Thing

I’ve started, edited, then deleted and started this post from scratch a few times now. Nothing clever worked. So, straight to the point. Three weeks ago, I moved on from 2 years of building a very awesome hyperlocal news aggregation platform at to my Next Big Thing.

I’ve left to pursue a remarkable new opportunity that I can’t discuss quite yet; not because I don’t want to, but because, dammit, they won’t let me! It’s got some key facets that ultimately pulled me away from the killer team at OI: it’s in a space that will impact everyone I know, it challenges me to build apps that I will want to use every day, the scale will require some clever architecture that’s stretching my thinking, and it presents a true startup-business-building challenge for me. BTW, we’re hiring Scala and Ruby developers, so get in touch.

I am beyond proud of what we have accomplished at, and of what the team I’m leaving continues to build there. The OI platform is in great shape. The public API is impressive and live and it’s one of the best out there, powering hyperlocal for huge sites like The next phases of its evolution are in the best possible hands. I’m incredibly thankful for the experiences of the past 2 years, and grateful to the team that made them possible.

ASSERT: Learn by Testing

My 6-year-old daughter received a microscope kit as a gift. It’s not the 50’s-style die-cast behemoth I had as a kid, with all it’s frustrating sample mounting and focus issues. No, this is 2009, and this perfect kids’ ‘scope requires no focusing and is small enough for her to wear as a necklace. And, it’s pink which makes the necklace prospect all the more attractive.

I’ve been teaching her a little bit about science and encouraging her questions. But really, I am passive, watching her formulate theories and test them. Our freezer is full of “samples” from the last Brooklyn snowfall.

She is learning to learn by testing, to come up with an assertion she believes to be correct, and then by observation rule it in or out. The application to programming and building systems is obvious, but easy to forget. I’ve sometimes fallen into the trap of assuming something is true, and relying on that assumption without a proper assertion and test. With the overwhelming amount of reading material available on what works and what doesn’t from “cloud computing” to scaling Ruby, from development environments to search algorithms, it’s easy to fall back on assumptions, most often and dangerously someone else’s assumptions. Watching my daughter’s inner scientist emerge has been a good reminder for me.

I now assert, and have proven, that even New York City snow is made of ice crystals and melts at room temperature.