Last Saturday was gorgeous in Boston, so I spent most of the day at the Microsoft NERD Center with a bunch of product managers, product marketers, and product developers for ProductCamp Boston. It was fantastic.

Like ~70% of the other attendees, this was my first ProductCamp. I have to say, it’s exactly what I expected from a conference created by and for product people: democratic, efficient, well-communicated, and nothing extravagant. ProductCamp Boston follows the unconference model. Any participant can volunteer to lead a session, and every participant is allotted an equal number of votes, which helps determine which sessions get larger meeting spaces. The calendar is distributed the night before the event so people have time to plan accordingly. I got a long, detailed email several days in advance that outlined everything you’d hope to know (including alternative driving directions due to a last-minute closure of Memorial Drive).

Registration was quick, and I was pleasantly surprised when ProductCamp gave me the choice of a rebate on my registration or a donation to the One Fund Boston (I donated). Wifi was reliable and passwords were easily found. Volunteers were stationed where they needed to be so no one was roaming around the NERD Center. Ample food was made available for breakfast and lunch, and they fed all 300 of us with startling efficiency. I’m relatively new to product, so a lot of what I heard was an affirmation of previous thoughts and conversations.

The morning keynote session was all about big data, a topic I’ve grown increasingly familiar with at MyEnergy. The speaker, Dr. Leslie Ament of Hypatia Research Group, was clearly an authority on the matter, and a good public speaker, but I do wish she knew more about incorporating design into big data (and presentation design).

In my first breakout session, I was handed a 48-point checklist by Alyssa Dver of the responsibilities and skills required of a product manager. It’s that rare combination of effective communications, financial acumen, market knowledge, process development, interpersonal skills, and technical prowess. Small wonder there aren’t more product managers.

Following that, I heard about the dismal state of B2B product marketing and got a great batch of tips from eZuce’s Christina Inge (slides here). She advocated a shift from the old “features vs. benefits” discussion to one of “you-centered” vs. “other-centered.” Her general thinking—and I agree—is that your marketing must be directed at and made relevant to your customers and other stakeholders, instead of marketing to yourself. It’s okay to talk about features so long as you frame it in a way that puts the user/customer at the center of the message. “We added screensharing because you asked.” “Our new infrastructure keep your data more secure and let you access information twice as fast as before.”

After lunch, I found myself captivated by Neil Baron, who shared his experiences bringing a successful chemical product to market. He explained how Chekhov’s gun applies to product marketing: essentially, if you promise to deliver value, do it. Whether that value refers to the product itself, or an informational webinar, deliver the benefits and information you promise.

I had to leave early, so unfortunately I missed a late addition focused on product management in startups. Overall, it was a morning (and part of the afternoon) very well spent. It was a great way to learn and network, and I’m sure I’ll be attending next year.

With the week now over, there’s been time to look back and reflect on all that’s happened. I grieve for the families, friends, and neighborhoods of the displaced, injured, and slain, and I mean no disrespect when I say that this week has been truly inspiring. There have been so many feel-good stories, it’s impossible not to be proud of my hometown. I’ve always said that Boston is a city that punches above its weight, and last week stands as a remarkable example of how this city responds to adversity.

The stories of first responders rushing towards the explosion site and marathoners heading straight for the hospital to give blood on Monday. The makeshift memorials on Tuesday. The interfaith service on Thursday. And then Friday, something I’ve certainly never seen or read about in my lifetime: the city-wide lockdown to assist in a dangerous manhunt. Boston was thrust onto a global stage on Monday, and we showed the world what makes us great.

For its part, the Boston startup community banded together to help out. Fundraise.com set up a donation page, and had to upwardly revise the goal three times. Musically inclined members of a handful of startups got together for Techies Rock for Boston, a rock show that donated a portion of its proceeds to the One Fund Boston. Wayne Chang, founder of Twitter-acquired Crashlytics, basically live-tweeted the entire manhunt well ahead of the local news.

Then there’s the story of Jeff Bauman, the bombing victim who lost both his legs, whose first actions after waking up in the hospital were to help identify the bombers. (Help him pay his medical bills here.)

People saw how Boston handled itself, and the goodwill radiated outward. The NYPD came into town to cook burgers for Boston’s first responders who had been on the scene for nearly 24 straight hours. The Chicago Tribune sent pizza to the Boston Globe, who did a fantastic job keeping the public informed and took down their paywall for the weekend. Too many restaurants to list have donated food or proceeds to victims and policemen.

The Red Sox paid a classy tribute to all the officers involved before the start of Saturday’s game against the Royals, and FCC Chairman Julius Genachowski didn’t even mind when David Ortiz passionately declared, “This is our fucking city!” (Genachowski is from Brookline.) Later in the game, Neil Diamond decided to show up at Fenway Park to lead our unofficial sing-a-long anthem of “Sweet Caroline” in person.

We’re not done yet. It’s not over. The lockdown cost the city’s economy in estimated $333 million. Our beautiful Copley Square neighborhood has been closed for a week and treated as a crime scene. Mayor Menino recently announced his five-point plan to reopen the area, and some businesses have announced that they’ll reopen as soon as tomorrow.

So here’s what I’m asking: if you live in or near the city of Boston, make the time to go to Copley Square as soon as you can. Go shopping there. Grab a drink (two if you find a cop). Go out to dinner. Those stores and their employees needs your patronage. Be generous with your tipping.

If you don’t live in Boston, plan a trip to visit. Come with friends and family. We’ve got good shopping, beaches, history, dining, sports, and fine art. Go walk the Freedom Trail. Ride a Duck Tour. Take a boat ride out to Spectacle Island. Catch a game at Fenway (tickets still available!). Visit the Isabella Stewart Gardner Museum. Whatever you end up doing, I’m sure you’ll be pleasantly surprised by what the city has to offer.

Update: Check out this extremely helpful map put together by local startup Promoboxx on which retailers are open in the Back Bay: http://engine.promoboxx.com/client/backtobackbay/

Photo Credit: Blixt A. via Compfight cc

By and large, the cloud provides improved access and collaboration to documents and media. But, there seems to be at least one use case that takes a bit of a step back in the cloud: families.

Sara and I combined our iTunes and iPhoto libraries years ago because it made sense. We listen to a lot of the same music, and most new photos are important to both of us. (Here’s an awkward question to avoid: “Should we keep the honeymoon pictures on your laptop or mine?”) Then along came the cloud and there appeared to be a better solution to storing hundreds of gigabytes on an external HDD. For a reasonable $10/month, I had all the music, and I would save my favorite playlists offline to my phone.

Now, Sara has a few options: She can continue using our iTunes library, but iTunes 11 isn’t exactly Apple’s finest work. She can sign into Spotify on her devices with my credentials, but there’s no sense of ownership there. Or, she can sign up for a second Spotify account and subscribe to her favorite playlists of mine (and anyone else). Considering how much of the same music we listen to, it doesn’t really seem justified to pay for a second subscription, but that’s what we’re doing.

Here’s the rub: with their playlist subscription and collaboration features, Spotify is actually one of the best examples of how families can use the cloud. For most cloud subscription services, the best solution is “sign in as another user.” I completely understand if my wife doesn’t want to have to sign in to her apps as her husband. That’s not exactly progressive. And certain services (looking at you, Apple) discourage you from this behavior. Sharing iBooks is next to impossible (it requires cords!) but guess what—reading is a social activity.

So what can be done? Why aren’t there true family accounts for the cloud? I would gladly pay a premium for the ability to associate two email accounts with an Apple ID, Spotify, Dropbox, Flickr, or other personal cloud accounts. I’d probably do it for Netflix too, because our combined recommendations are becoming insane. (“Because you watched Grey’s Anatomy and The Grey, we think you’ll like Dr. Doolittle 2.”)

How are other couples and families dealing with this?

I recently finished reading Grand Central: How a Train Station Transformed America. It’s a fantastic, easy read that tells the story of the terminal from the rise of railroad commuting in the middle of the 19th century to through its salvation in the 1960s and its recent renaissance in the 21st century. I’m a sucker for civil engineering reads because at their root, they’re all stories of willful people designing innovative solutions to problems with sweeping impacts to society.

Reading about Grand Central, I was reminded of a few of a business lessons that pervade across the startup community.

Grand Central under construction in the 1900s

1. Start with the problem.

In 1902 Manhattan suffered its worst railroad accident. A train headed into New York City crashed at 56th Street, killing 15 and injuring 36 more. At that point in time, 177,450 trains powered by coal and steam traveled through the unlit Park Avenue Tunnel every weekday—one every 45 seconds during rush hour. In addressing the issues that caused the crash, New York Central’s Chief Engineer William J. Wilgus devised several ingenius solutions. He electrified the track, which yielded several game-changing benefits, most notably the ability to develop the land on top of the tunnels leading to the station.

The best products—and the best companies—address real problems, and success follows.

2. Skate to where the puck is going.

Cornelius Vanderbilt, the lead financier for Grand Central Terminal, made his name in steamboats. He took his first railroad trip in 1833 which derailed and nearly killed him. When he was approached to invest in the Harlem line, he replied, “I would be a fool to sink my money in a business that sets out to compete with steamboats.” Yet, by the 1840s, he saw the writing on the wall and had begun investing in railroads. Now there’s a statue of him in front of Grand Central.

Steve Jobs famously quoted Wayne Gretzky’s strategy of “skating to where the puck is going to be, not where it’s been.” When the iPod was just a music player, Jobs denied a claim that they would add video playback as a feature, saying, “It’s about the music, stupid.” Obviously, it eventually became about more than music for Apple and its iDevices.

3. Iterate. Don’t jump right to infinite scale.

The first building to bear the name Grand Central was completed in 1871. Grand Central Depot was built at 42nd Street, well north of the commercial center of New York at that point. Vanderbilt said the building would suffice for a century, but in less than 30 years, the city had outgrown Grand Central Depot’s capacity. In 1898, after Grand Central Depot was denounced as being “considered adequate in Sandusky, Ohio,” a facelift was in order. Just a few years later, the renovated building was torn down and replaced by the Grand Central that still exists today. The railroad company, long before it was in fashion, built, measured, and learned.

Grand Central Depot in 1871, “neither grand nor central”

The train station that exists at 42nd Street has evolved through iteration in name, scale, and technology. A station that handled 100 million people annually was inconceivable—not to mention unnecessary—when Grand Central Depot was commissioned. Electrified tracks certainly weren’t a viable option in the 1870s. Ever the innovator, Wilgus built some futureproofing features into his station. Grand Central was intentionally built with a super-strong foundation so that it might one day support a tower over the station itself.

4. Don’t worry about technical debt, until you have to.

Park Avenue tracks in the 1870s

Steam locomotives made all the sense in the world in the 19th century. Leading up to the 1902 crash, people knew that the Park Avenue Tunnel had its inherent flaws. Too many tracks intersected too closely together, and a dozen bridges were required for passengers and carriages to cross over the sunken tracks. It was incredibly disruptive to the city. Coal and steam powered trains running through an unlit tunnel created health and visibility dangers. Eventually, the technical debt of breakneck urban expansion in New York combined with growing popularity of railroad travel came to a head and the viable, responsible option presented itself to transition to new technology.

5. Someone will tell you you’re crazy long before you’re proven right.

The Times said that Vanderbilt’s Grand Central Depot “can only by a stretch of courtesy be called either central or grand” given that it was still an hour north of City Hall, then the center of New York. When William J. Wilgus proposed the electrification of the tracks, he had his detractors. His biographer wrote, “No existing railroad electrification anywhere in the world approached the scale of the Central’s project or provided a model to duplicate.” Of course, both men ended up being proved right—in epic proportions.

Grand Central, interrupting the New York City grid

Grand Central’s subsurface rights between Lexington and Madison and East 42nd and 47th Streets now defines “Midtown.” Thanks to an elevated roadway, Grand Central is uniquely positioned as one of very few buildings to interrupt New York City’s gridded road system, giving it one of the most enviable vantages in the city. Electric train tracks inevitably won the day and have allowed for all kinds of transit development, both above and below ground.

There are countless lessons to be learned from the way Grand Central has redefined itself over time. These are the handful that resonated with me. The book was inspiring, and I can’t wait to revisit the building during my next trip to New York.

all images via Grand Central: How a Train Station Transformed America

image via pierofix via Compfight

I’ve been trying to figure out what to do with my photo library for a while. First, I had to tackle the issue of combining my photo library with my wife’s—they were our pictures now. We ended up with a 40+ GB iPhoto library that couldn’t really fit on our MacBook Airs and leave room to do anything else. We ended up moving it to a 1TB hard drive that’s plugged into the USB port on our AirPort Extreme. This was nice because (1) it let both of us access the photos from either machine (2) it freed up significant hard drive space (3) it could be accessed anywhere via Back to My Mac.

In theory.

What really happened is we took all of our pictures—our college years, the wedding, the honeymoon, our holidays and trips together, all the memories—and put them out of reach. Have you ever tried launching a 40+ GB iPhoto library over Wifi? Not so great. And interacting with the contents of said library is even worse. Just scrolling through events triggers the Beach Ball of Impatience.

It was so bad that we all but stopped using our Nikon D40. In the back of our minds we knew that after all the post-production we’d just lock those photos in a virtual crate and ship them to an offsite archive. We hardly ever reopened iPhoto to sync with our Photo Streams, and we have precious little local storage on our phones to store all the old albums.

The time had come for a better way. I wanted a way to browse all my photos from my various connected devices. I wanted to be able to share my photos with others. And, if possible, I wanted to be able to make collaborative albums with friends. I had recently discovered Dropbox’s photo upload feature, so I started there. I’ve always liked Dropbox. It’s very intuitive, you can get a generous amount of space for free before you have to start paying, and it integrates nicely with all my devices (unlike, say, Amazon Cloud Drive).

So I plunked down $9.99 to buy 100GB of cloud storage this month and started moving my albums there. The trick to using Dropbox and keeping hard drive space free is the Selective Sync option under Preferences:

Selective Sync under Preferences > Advanced in Dropbox

My Photo Stream camera uploads get instantly uploaded and are locally available on all devices, but the old photo albums themselves are only accessible with an Internet connection. Plus, with Dropbox’s sharing features, I can control who gets to view and edit different album folders.

However, Dropbox only uses thumbnail view for the Camera Uploads folder, not its sub-folders. So when I browsed through an old album, I was really looking at useless filenames and very small thumbnails. Yesterday, I discovered DropPics, a $1.99 app which supports thumbnail view and a few other photo-friendly features. Check out the difference:

I’m feeling pretty good about the setup now. All my photos are available on any device, wherever I go, and it doesn’t crash my computer to view them. It’s easy enough to group photos into albums, and when I do touch up photos, I can do that locally via Lightroom and then upload them to Dropbox.

This is clearly not the only solution for a cloud-based photo library, so I’m curious to know what others use.

We’ve been on the verge of an Apple television set for a few years now. Hype and speculation were fueled by a mention in Walter Isaacson’s Steve Jobs 2011 biography that Jobs wanted to invent an integrated television that fit into the ever-expanding Apple ecosystem. More recently, one analyst reporting from CES 2013 called the latest batch of smart TVs underwhelming, and declared it an opportunity for Apple.

But why exactly does Apple need to release a television set? Let’s look at some pros and cons:

Pros

1. Apple excels at hardware-software integration, and they insist on end-to-end control of the user experience and engineering process.
2. TVs are big ticket items, so it would do wonders for Apple’s top line. By most estimates, the starting price for an Apple television would well exceed its two most popular devices, the iPad and iPhone, and even a portion of its Mac product line.
3. Every Apple television sold is another Samsung television sitting in a warehouse or showroom floor.

Cons

1. The margins on televisions historically are around 10–20%. Granted, Apple has a habit of industry outperformance with its premium brand and manufacturing advantages, but it’s hard to imagine a television not dragging down Apple’s margins of nearly 45%.
2. The upgrade cycle on TVs does not fit well into Apple’s upgrade cycle. Most people replace their phone every ~2 years and their computer every ~3 years. For TVs, the most aggressive households upgrade every 4–5 years.
3. Apple faces an enormous uphill battle to get cable companies and content producers to play nicely here. They pulled it off in the music industry, but the television/movie industries seem even more resistant to change. Amazon, Netflix, Hulu, and Apple itself are all struggling to secure reliable video content agreements that don’t suck for users, and it’s been going on for years.

So here’s my devil’s advocate argument: What if the long-rumored Apple television were just the existing Apple TV, with some spec changes? Presumably, an Apple television would differentiate itself through the user interface, and that would most likely center on Siri—and possibly gestures. If you added a front-facing camera and a microphone to Apple TV, why would Apple need to go through the trouble of manufacturing the screen too? Open up the device to support third party apps, and you’re good to go. Now you’ve got a box that you could retail for $199 that lets you stream and rent music and videos, access photos and your other cloud-based media, play console-quality games, and browse a curated web. Advantages? Customers are more likely to purchase multiples for the household and upgrade their hardware more regularly. It also plays nicely with Apple’s goal of expanding its presence in emerging markets, where big screen TVs are less of the norm. Apple would also command a stronger margin on an Apple TV that relies on fairly basic components and skips the large panels of glass.

The only thing missing would be the live cable stream, which presumably could be added to the box as well. If you pay for cable, your current TV doesn’t handle the live stream. With all the effort being put into smart TVs, why don’t we just demote it to being a monitor and put the intelligence elsewhere, in a device that you can upgrade more regularly?

The downsides to this plan? You still have that crazy TV remote on your coffee table, and Apple would have to be specific about where you place the Apple TV relative to your viewing angle. And, yes, they would probably make less money, but they would grow their profits. Maybe I’m crazy, but I’m not totally sold on the obvious need for Apple to start selling me a TV.

Some journeys should not be measured by time or distance. For example, I left my old job in corporate consulting for 72 days and traveled a net of 440 feet to my new job at MyEnergy. Clearly, that doesn’t really do it justice.

What happened in between was a complete professional overhaul that allowed me to change industries, develop new skills, expand my network, and forge a new path for myself. Here’s how I did it:

1. Find a catalyst.

I suppose that technically I could have found a startup job on my own, but it would have taken months—if not years—and been no fun at all. After all, I had mentally made the decision to leave my old job in April, and hadn’t made any measurable progress in six months. Boston Startup School accelerated my transition by exposing me to the right people and putting me in the environment to get shit done. It made all the difference. Your catalyst could come in a number of forms. It could be a single class, a talk, an internship, or a coffee meeting.

2. Meet new people.

Startups are most assuredly a community, and in a city like Boston, it’s a pretty tight-knit community. Everyone knows everyone else, so the right connections can get you the introductions that get you the opportunities you’re looking for. You meet these people at community meetups, industry conferences, parties, demo days, and coffee shops. For the most part, these are not private events, and you can find them online. In Boston, you can go to Greenhorn Connect, the BostInno calendar, Boston TweetUp, or VentureFizz (to name a few) to find startup events. See below: the dark blue cluster is my “old” network and the purple and light blue clusters are the Boston startup community.

I began to tiptoe into the startup pool by attending (and then teaching) classes at Intelligent.ly, then ultimately decided to apply to Boston Startup School, which is where I was introduced to MyEnergy.

3. Acquire New Skills

Liam Neeson would do great in startups, because they’re are looking for a particular set of skills. Marketers need their growth hacking; developers need their actual hacking; designers need their front-end; and salespeople need their improv. But that’s just the beginning. Everyone in a startup needs to understand how to work with people on other teams, in close quarters, and in stressful situations. If you’re an early team member, you’ll probably be involved in the hiring process for future employees. You’ll inevitably be asked to do things beyond your job description (assuming you have one to begin with), so you’ll need to be prepared to deal with those challenges. What’s more, you also need to understand how to deploy all these skills in a fast-paced environment. Good startups (the kind you want to work for) employ methodologies with names like lean, agile, Scrum, and Kanban. Get comfortable with them.

My professional background gave me strong communication and managerial skills, but I wanted to be better at implementation, so I learned UX/UI skills like Photoshop, Illustrator, HTML, and CSS. I’m no expert, but I have enough of an understanding to know what’s possible, and I’m much better prepared to have productive conversations with developers.

4. Ask Yourself Questions

Startups aren’t for everyone. That’s not a knock on people who aren’t interested in startups. Entrepreneurialism has been described as a disease, something you have and can’t suppress. Working at a startup probably means taking less pay than you’d make in a traditional corporate role, accepting equity in a company that statistically has a 90% chance of failure, and dealing with the constant fear that your strategy is all wrong. First, you have to determine if you’ve got “the startup bug.” Quitting your old job is the easy part. The hard part is figuring out what to do next. What do you have to learn to get where you want to be? This question begets about 20 others. You will (or at least should) have countless conversations about how to prioritize compensation, culture, mission, and responsibility.

I wanted to work at a company where I could build things. I wanted a company solving a worthy problem, playing in an attractive market, led by an impressive team, following a sound process. I found one in MyEnergy. The company aims to lower energy consumption by helping people understand their utility bills. I will be responsible for building out their account management process with utilities and their national user rewards program. It’s a tall order, but it’s a perfect mix of work I’m good at today, and work I want to be good at in the future.

I’d be lying if I said I wasn’t a little nervous, but it’s an absolute thrill to know what I want to be doing and to be in a position to do it.

I used to work at a local video rental store (Google it if you’re too young). Monday nights were always big because we had to get the store ready for new release Tuesdays. There was a schedule, and every Tuesday we’d rotate out the new releases wall, adding the newest titles that just came in and demoting the oldest ones to the regular shelves organized by genre that filled the rest of the store. We also had to change out the movie posters in the front of the store that were used to draw passers-by.

You could almost tell by the way a customer entered the store whether they were going to get a new release or an old movie from the genre aisles. New release renters walked in more casually because they were preparing to browse the new release section. They were the majority of customers. But other customers walked in with purpose because they know where they’re going and what they wanted to see.

Here’s the thing: customers at that old rental store knew that Tuesday was new release day. Sometimes people would just stop by on their way home from work to browse the new releases. They might not see anything they want to rent, but they came into the store.

Today, Netflix doesn’t give customers a reason to go to their site unless they specifically want to watch a movie at that moment. This is wrong. What control does Netflix have over its monthly active user metric? They can’t make people want to watch more movies, but they can make people want to visit the site more, and make it easier to build out their Instant Queues (the feature that drives repeat visits). With tens of thousands of movies available for instant streaming, Netflix creates a paralysis of choice. I know I’ve wasted upwards of 30 minutes browsing through Netflix looking for the right movie to rent. It’s no fun.

Plus, Netflix has a user experience challenge with the expiration of its content agreements. Have you ever gone to Netflix to re-watch an old movie only to discover that it’s no longer available to stream? It’s discouraging. By embracing a release schedule, Netflix can address this.

Imagine if every Tuesday you could go to Netflix and right there on the homepage it shows 20 New Titles (curated by Netflix as some combination of new releases and recent additions). And just below that, an Expiring Soon section. It takes all of 5 minutes to go and update your queue accordingly, or maybe you just start watching Hot Tub Time Machine right then and there because it’s going to leave Netflix at the end of the week.

Currently, there’s no telling when Netflix will add new titles or beef up its back catalog, so most times you browse the new releases you leave disappointed because they’re the same new releases as a month ago. And when Netflix does sign a new content agreement, they could add hundreds if not thousands of movies at once (the benefits of digital distribution right?) except even if you knew when this would happen, it’s impossible to parse through all the titles. Netflix should separate its content acquisition strategy from its release strategy. They need to build in a reason for people to come to the site more regularly.

Current Netflix subscribers: Would you come to Netflix more often if you could reliably check the new additions once a week?