Articles

I've written hundreds of articles about technology, advertising, digital media, photography, venture capital, fundraising, and more, and been quoted or featured in Fast Company, Wired, Fortune, MIT Technology Review, AdAge, Digiday, The Next Web, Forbes, Crain's, and more.

 

Technology and Venture Capital

Why your homescreen will change
How new technologies to see, interact with and understand the world - image recognition, voice interfaces, and machine learning - will change mobile operating systems.

Bots, the new-new-old thing
Why are bots notable? Not because of what they are, but because of what they can do.

Algorithms and The Pursuit of Advertising
Instagram's shift to an algorithmic feed is an age-old story playing out yet again. And Snapchat? Coming soon.

The Entrepreneur's 2016 Gift Guide
What to get now to start planning for 2016.

Why is a shoe company a "startup"?
On the role of technology in startups, and why shoes, furniture, mattresses, clothes, food, and "non-tech" businesses are the hot startups of the moment.

The future of big data, ad blocking and tracking
Is big data a big asset or a big liability? That's up to us. Let's consider how we are using data to make better products and ads while dealing with security, privacy, and tracking.

Artificial Intelligence in Fintech
The financial services industry has seen the buzz over artifical intelligence before, but will the result be different this time?

Small (and Big) Data
Data abstinence and artificial intelligence.

How the Future of Mobile Apps Impacts Ads and Brands
The future of mobile apps will create new avenues for mobile ads. But it all starts with user experiences.

Users, meet Advertisers
The shift from a product people love to a product advertisers love is tough. But that should be expected.

Peak Password
Why the password needs to be replaced

Apple Watch
I'm more excited about Apple's watches than their phones. Here's why.

23 Things I've Learned as a VC
Looking back at three years in venture

Why Mobile Unbundling Isn't Inevitable
The state of mobile app unbundling today, and how app extensions, deep linking, and notifications could alter the rationale for unbundling.

The Internet of Things is about people, not things.
A talk I gave at Startup Iceland, 2014

The State of Programmatic Advertising
... will be defined by the sites we make popular and the ad units made to fit them.

Why Deep Linking Matters
Mobile apps are adding back the structure of the web, bit by bit.

The Peer-to-Peer Movement
Signs of how peer-to-peer technologies will disrupt the centralization of the Internet.

Card Architecture and Card Design
Cards are not the first form of embedding interactivity, but it's the one with the biggest future. Look beyond the design of cards to the architecture behind them.

Publishing as a Product, Pageviews as Users, and What The Shift Means
Re-thinking publishers as "intent engines", and what it takes to get there

The mobile single-purpose app strategy
Thin wedges can be valuable icebergs.

Fundraising for Entrepreneurs
Slides from a talk about Fundraising for Early-stage Entrepreneurs I gave at Carnegie Mellon University's Tepper School of Business, Feb 14, 2014

It's a fascinating time to be a publisher
An overview of digital publishers today.

Mobile messaging, brands, and adtech
Mobile communication apps may not appear to be adtech companies. But then, neither did social networks.

Feedback from Founders
I surveyed all the entrepreneurs I've met about what I did right AND wrong as a VC. Here's what they said.

Angellist Syndicates is crowdfunding without the crowd. For now.
It's impossible to think about Angellist Syndicates without looking at the broader picture of equity crowdfunding.

A VC's take on CGI 2013
Thoughts from Clinton Global Initiative by a tech venture capitalist.

The most interesting companies in advertising are built for people first, marketers second.
If you want to figure out the future of adtech, look to where consumer technology is going.

Why it's hard for startups to hack brands and agencies for growth
There's a difference between business development and selling.

Hardware is Feeding the World
Software might be eating the world, but hardware is feeding the world.

International First
Perhaps instead of web-first, or mobile-first, we should think about international-first and what that means.

I want to…
When you think “I want to..”, what do you do?

Context First
The next set of winners in web services will use the organizing principle of “context first” to build on top of social platforms, mobile platforms and data platforms to rethink how their business operates.

Intent Data, the Key to Internet Marketing
Detailing how first-party digital intent data can be used by marketers and advertisers, and why intent data is not the same as social data. Startup idea enclosed.

How crowdfunding could impact the venture capital industry
What happens when everybody’s a venture capitalist? The crowd is waiting to disrupt yet another industry, and the time is now for the venture industry to take advantage of it.

Why digital intent matters
A glimpse into why we’re going to hear a lot more about “intent” in digital marketing.

The best technology fades into the background
The best technology fades into the background, because people don’t care about tech, they care about what it does.

Intent Engines, Sponsored Actions, and Internet Marketing (why Pinterest, Polyvore, and Personal et. al. matter)
Social services as intent engines, and why they are important to advertisers.

Tim Tebow and the Minimum Viable Offense
The idea of a minimum viable product doesn’t apply just to startups.

How to start charging for what you make
A summary of a short talk I gave at Tribecon 2011

Facebook's potential Adsense competitor
In a “world where more stuff is known by more people”, how will social data link with ads across the web? Here’s one idea.

The real challenges technology companies face today are human, not technical.
And that’s a normal part of the cycle, not a failure of venture capital or innovation.

Information, Intelligence, and Wisdom. There’s a business in every part of the stack.
Data is great. Analytics are great. But the applications of data are even better.

The Missing Loop in Health Hacking
Health hacking technology and communities are all missing something. Today’s product and community diversity is a sign of immature products and value propositions, but tomorrow’s diversity will be a sign of competitive differentiation.

Bankers always maneuver faster than regulators (Facebook and Wall Street)
Everyone’s going to pay attention to Facebook raising $500 million. But pay much more attention to where the money is coming from.

The kids are alright.
Studies about generational differences matter. But not in the way we typically interpret them.

Why we create without getting paid
Why do people spend time creating without getting paid? Three big reasons, in my mind: 1) creating is a form of entertainment, 2) it’s never been easier to create and publish for free, and 3) creating creates. We can say yes without having to convince anyone else to say yes. And it’s great. But shifting from free to paid isn’t as easy as we may expect.

Doing Good is Good Business
Doing good is good business. “Social good” can be the base of a strong business model, and I believe we’re steadily coming closer to a point where a business without a “social good” is not a sustainable business. And I’m not talking about environmentally, culturally or morally sustainable, but strategically, economically and financially sustainable.

Where Meaning Meets Business
“Where meaning meets business” is a simple construct that can help us allocate our money, time, attention and love; why should we do things that don’t matter?

Financial Models Are (Still) Always Wrong: Create One Anyway
After a lot of interest from entrepreneurs for a simplified version of that model, today I’m releasing a streamlined version that will make it easier for entrepreneurs to start understanding the equation underlying their businesses.

The Passing of the Polymath
Once admired for their breadth of knowledge and ability, polymaths are now ironically mocked for the exact same quality. Why?

The data revolution in baseball continues.
On technology and data-driven decision-making in baseball.

A “Personal API” could be a modularized, standardized interface for collaboration.
Continuing the conceptual thinking around a “personal API”

Financial Models Are Always Wrong: Create One Anyway.
Why is creating a financial model important?

How to Fail - 25 Lessons Learned through Failure
Close observation and unfortunate first-hand personal experiences have taught me many lessons about why companies fail. Here’s 25.

Photography

On Photography (in 2016)
What happens when photography technology diffuses into society?

Why does real photography matter?
The impact of selfies and computational photography on professional photography today.

The key to winning Instagram
"You have to be interested to take interesting pictures."

Beyond Better Images
I'm excited about technologies that help us create better photos, not just better images.

Software is Eating the Camera
How software is changing the form and substance of cameras and photos

The Future of Mobile Photography Apps
iOS 8, Android L, and the implications for mobile photography

Social photography is changing stock photography.
From Shutterstock, to Getty, to EyeEm and 500px, social photography is having an impact on stock photography.

How a single sentence changed how I see
On a spring Saturday a year ago I sat down for a photography portfolio review at International Center of Photography. What I learned applies far outside the world of photography.

From Photogram to Instagram
Behind changes in mediums and messages, from the photogram to the instagram

The Filter Future
Digging a bit into Vine and Instagram, here’s the path to the next round of innovation in consumer photography. And it’s not in “filters” in the current sense of the word.

Tell Stories
Share snippets, and enjoy it. But don’t stop there. Share stories also.

Photographing Summer in Boston with the Camera You Have on You
A recent feature in Gizmodo talking about how I shoot

The Lytro isn’t a new camera, it’s a new medium.
The Lytro is a discontinuity in digital camera evolution.

Everyone is a photojournalist.
... and that’s ok. Because even though everyone is a photojournalist in their own way, the dedicated photojournalist still has a valuable role to play.

The deluge of the amateur photographer, redux.
Retracing an old discussion about the impact of the deluge of the amateur, linking together yesterday’s fair take by the NY Times with a post of mine from September 2007

DSLRs are SUVs
Do people really want bigger cameras? No, and that’s why the micro 4/3 innovation is important, not as a sign that micro 4/3 is the solution the mass market wants, but that DSLRs aren’t really what the mass market wants, either.

Unbundling the Photography Industry, Redux
Break down the stack of services in the photography industry and imagine a photography sales platform that operates as a search engine through the internet’s warehouse of images; the current issues in the photography industry are signs of long-term pressures and hints of the industry’s future.

Lesson 4: Connect with context and content
It’s always been about creating great content, but there’s now a larger opportunity than ever to deliver great context.

Everyone is a photographer.
Photography as communication, not just art.

Travel

Caught in the Act
Reykjavik, Iceland

Blue
Southern Peninsula, Iceland

Bias for Curiosity
San Francisco, CA

My Cities, 2016
22 cities and 72 nights away from home.

How to Pack for a Family Trip (and the 10,000 things I packed)
I'm joking, I don't think it was actually 10,000 things. But it felt like it.

My Cities, 2015
23 cities and 141 nights away from home.

Minimal Mode
Non-stuff is easier than non-self. We blame the demands of daily work and family life for making zen (and minimalism) unattainable, but the real reason is more raw: fear, ambition, desire, jealousy.

New Orleans, The Food
72 hours of New Orleans food

Do Lectures, Australia
Talking about esoteric technology? Easy. Talking about my life? Hard.

My Cities, 2014
28 cities and 148 nights away from home.

14 from 2014
Fourteen photos from 2014 to summarize the year.

Retreating
Copake Lake, NY

Kansas
Where twisters come from.

20 Things I Pack for Living
What I use to live when I travel.

The Do Lectures
Cardigan, Wales

Moving on from kbs Ventures
After a great three years at kbs+ Ventures, the time has come for me to move on. I'm excited to announce that I recently resigned to pursue new endeavors.

Milford, CT
Woodmont Beach

London, England
What I do when I'm in London

The Great Saunter
Manhattan, New York, NY

Up in the Air
The nostalgia of the airplane window photo

Reykjavik, Iceland
Exploring Castles in the Sky

DLD 2014
Munich, Germany

CES
Las Vegas, NV

My Cities, 2013
30 cities and 109 nights away from home.

13 from 2013
Thirteen photos from 2013 to summarize the year.

Hidden Valley, PA
Winter Wonderland.

Pittsburgh, PA
Urban Nature.

Naples, FL
Boomtown.

New Paltz, NY
What laid down the path.

Los Angeles, CA
Living in public.

Venice, Italy
Peering past the tourists.

Tuscany, Italy
Getting lost is part of the fun.

Rome, Italy
Using the frame I brought with me.

Escaping The City
It's amazing how many great escapes are available outside NYC.

Tanglewood
How to do Tanglewood right.

Milford, CT
How Sundays are supposed to be lived.

Burlington, Vermont
Americana.

Eagle Bridge, NY
Using what we have.

Sag Harbor, NY
From a 25 mile ride from Sag Harbor to Amagansett and back.

Hudson River Valley, NY
Adventures out of NYC

Providence, Rhode Island
Walking the streets of Providence

San Francisco, CA
The sights of business travel.

Richmond, VA
Venturing outside the bubble.

New Orleans, LA
What I recommend in NOLA

Montauk, NY
There's something wonderful about exploring a place out of season.

Austin, Texas
Before the world arrives.

St. Augustine, FL
Pulled to the edge.

Berlin, Germany
Forever unknown.

DLD 2013
Munich, Germany

My Cities, 2012
28 cities and 97 nights away from home on a quiet year.

Paris, France
Understanding Paris's "love locks".

A Week at a Colorado Dude Ranch
Black Mountain Ranch, CO

Spending Thanksgiving Giving Back
Panajachel, Guatemala

Unsilent Night, 2011
New York, NY

I love the street food in Asia.
What I love about street stall eateries in Asian cities.

Making Myself Uncomfortable (A Zombie’s Journey)
A story about a zombie's early morning flight from New Orleans to San Francisco.

The Tuttle Club
A note about Tuttle, my new favorite ritual in London.

Three days hiking in the Rila Mountains, Bulgaria (a story untold)
An improvised three days hiking in the Rila Mountains in Bulgaria.

Looking out, looking in.
A hot, languid day train from Bulgaria to Romania, (Veliko Tarnovo to Bucharest via Ruse)

An introvert, in the wild.
Introverts live differently than extroverts. Not surprisingly, they also travel differently. Trust me, I know.

Creating the means to match the spirit (How to Plan for Travel)
Responding to a request to outline the logistics of a nomadic life beyond the small matter of what to pack.

One night on a train from Istanbul to Sofia
Snippets from an overnight train ride on the Bosphorus Express from Istanbul, Turkey to Sofia, Bulgaria on my current little jaunt.

Street Art from Istanbul, Turkey
A request for street art, fulfilled.

Modern Flaneurs
The term flaneur may date back to another era, but it’s an idea and an action more relevant today than ever.

How to Pack for a Nomadic Life (and the 79 things I packed).
The 79 things I packed for a trip around the world.

My Cities 2008
72 different cities in 5 countries.

Centralia, PA
A smoldering ghost town tucked away in Pennsylvania.

Cultural Tourism
Bangalore, India

Wow
Half Dome, Yosemite, CA

Obstacles
Crianlarich, Scotland

Where tourists and travelers meet
Inversnaid, Scotland

Trail Magic
Drymen, Scotland

Get On The Bus
Puerto Vallarta, Mexico

The Crew
Glasgow, Scotland

A Misplaced Day
Arlington, VA

Winter Camping
Dolly Sods Wilderness Area, West Virginia

Hello, 2007
Virginia Beach, VA