Dear Mom:

You asked me to write to let you know if I arrived safely in iCloud-land. Well, I’m here and I’m in one piece, although unfortunately some of my things didn’t make it here with me, such as my calendar. It was a pretty hellish journey, I’ll tell you. There were a couple of long stops where I wasn’t sure I was going to make it the rest of the way, and we almost crashed a couple of times. The whole trip took about 16 hours! I think you’ll like it here in iCloud-land and I hope to see you here soon. But I hope you can find a less hectic day to travel.

Love, Wade

If I had to write a postcard home about my experiences switching over to iOS 5 and iCloud on Wednesday, that would the sanitized version. The honest version would include a lot more swear words.

Don’t get me wrong—the new version of Apple’s mobile operating system and the cloud-based sharing service that goes along with it are great. They make your iPhone, iPad, and Mac even more useful than they were before. If you’re an Apple customer who hasn’t already upgraded, I don’t want to discourage you from doing so. But I do want to summarize my tale of iCloud and iCal woe, in the hope of saving you a little heartache along the way.

Some of this story came out yesterday in an article in Talking Points Memo. Tech reporter Sarah Lai Stirland had come across the series of increasingly ticked-off tweets that I penned Wednesday as I attempted to get my whole menagerie of Apple devices upgraded to the latest specs. She called me up Thursday morning to ask for more of my tale, and I gave her an earful.

The new iCloud settings menu on the iPhone

But looking back on my tweets and my talk with Stirland, I regret playing the indignant card, because the truth is that I predicted all of this months ago, and, at least to some extent, brought it on myself. (I honestly only blame Apple a little—more on that below.)

I figured it was the duty of every self-respecting alpha geek to download iOS 5 the moment it was available Wednesday morning. Unfortunately, tens of millions of other iPhone, iPad, and iPod Touch owners were doing the same thing at the same time. So that was problem number one—the parts of the upgrade process that depended on Apple’s servers went in fits and starts.

The first order of business was to upgrade Lion, the operating system on my MacBook Pro, to the latest iCloud-compatible version (10.7.2) and to upgrade iTunes, long the master program in the Apple universe, to version 10.5. That all went fine. Next came my iPhone 4. That’s where the snags started, for me and a lot of other folks. Before iTunes can put iOS 5 on your iPhone, iPad, or iPod touch, it has to back up key data such as contacts and calendar appointments and completely erase the device itself, including all of your music, movies, books, and other media. Then it installs iOS 5, restores the data from the backup, restarts the device, and re-syncs your media material from iTunes. The restore part is what kept failing for me. The restore process would appear to be on the verge of finishing, but then it would fail, giving me cryptic messages like … Next Page »

Comments (14) | Reprints | Share:          

This is the second in a series of profiles of Y Combinator Winters 2011 (YC W11) startups.

Whatever your thoughts about modern technology and whether it’s making life better or just busier, you can’t say that no one feels your pain.

In fact, hundreds of new startups pop up every year to fix perceived pain points in the way we organize our digital lives—and no small fraction of them seem to come from Y Combinator, the Mountain View, CA-based venture incubator. Yesterday, I wrote about Taskforce, a YC Winter 2011 company that has created a Gmail widget that helps you regain control of your inbox by converting e-mails into to-do items. Today, I’m putting the spotlight on Noteleaf, another two-man Y Combinator startup with a service that sends you key details about your business contacts when you need them most: right before you meet with them.

Noteleaf is a simple, set-it-and-forget-it tool that leverages your existing online calendar and social networking accounts. When you sign up, you give the service your cell phone number, as well as permission to connect to your Google Calendar and your LinkedIn account. Then the company’s software scours your upcoming appointments for the names of the people you’ll be meeting with, and looks up those people on LinkedIn.

Exactly 10 minutes before a meeting, Noteleaf sends you a text message with a link to a mobile Web page with your contact’s profile. The page includes their photo, work history, recent tweets, a link to your e-mail correspondence with that person and a Google Map showing the location of the meeting. It’s like that no-nonsense secretary Mrs. Landingham on The West Wing, handing you a briefing book just as you go into your next big negotiation.

“It’s especially useful for people who book a lot of meetings,” says Noteleaf co-founder Jake Klamka. “Maybe you booked this meeting two weeks ago. You didn’t need the info an hour ago, but now it’s 10 minutes before the meeting, and you are rushing, and you really need it. We are going to present it to you in one compact, quick-to-review package.”

I’ve tried Noteleaf and it works well—although, as with all software, things can occasionally go haywire (more on that in a moment). Perhaps the coolest feature is that once you’ve created your Noteleaf account, you never have to touch it again. The system checks your calendar on its own, and you don’t have to do anything special to prompt a meeting reminder. The company’s driving philosophy, Klamka says, is “don’t make people do any extra work, and send them the right information at the right time.”

The service has some limitations, which mostly reflect how new it is—Klamka says Noteleaf, like most YC companies, adheres to the lean-startup mantra of “launch early and get feedback.” So far, the service can only connect with your Google Calendar, so if you use Apple’s iCal or Microsoft’s Outlook as your datebook, you’re out of luck (unless you do a bit of extra work to sync Google Calendar with your existing calendar application). And the 10-minute warning time is fixed—you can’t change it to, say, 30 minutes or 5 minutes.

But what’s remarkable about Noteleaf is how much goes on behind the scenes to make sure you’re armed with the key information you need before each meeting. In particular, in a reflection of no-extra-work philosophy, the software uses some pretty sophisticated tricks to read your standard calendar entries and figure out who you’re meeting with. It makes life easier for Noteleaf if you include a contact’s full name in a calendar entry, but it’s not necessary.

Klamka was trained in math and high-energy physics, and he says that work involved learning how to write machine-learning algorithms that extract the signal from the noise in physics experiments. Co-founder Wil Chung has a computer science background and has worked on similar signal problems, Klamka says. “Whereas somebody else would have seen this [calendar] problem and said, ‘I am going to have the user enter an e-mail address [for every meeting participant], we thought we could do something interesting by using algorithms and natural-language processing and heuristics to extract the signal in this. We want to add value without you having to change your behavior in any way.”

That means, first, identifying the names in calendar entries, and then retrieving the right profile information for that name. If you type “Lunch at Four Seasons with Simon” into your Google Calendar, in other words, Noteleaf has to figure out not only … Next Page »

Comments | Reprints | Share:          

Big partnerships are often a key to success for startups. Especially one that plays in a crowded consumer tech sector like Cozi, which makes software for helping busy families manage their daily schedules, chores, and activities.

The Seattle-based company is announcing some new deals today, ones that could have a substantial impact on its business. Cozi has formed strategic partnerships with AOL, Intel, Working Mother, FlyLady, and Punchbowl. Financial details weren’t given, but I got the gist of how the partnerships work from Cozi CEO and co-founder Robbie Cape.

For AOL, Cape says, Cozi has created a family organizer for MyDaily.com, a news and information portal aimed at women. For Intel, Cozi has developed an online calendar and to-do list platform optimized for netbooks. For WorkingMother.com and FlyLady.net—news and mentoring sites for busy moms—the company provides access to co-branded versions of its family calendar and other tools. (That means the Cozi brand appears together with the individual site’s brand.) Lastly, Punchbowl, a Boston-area party-planning startup, has integrated Cozi into its online event-organizing software, and Cozi links to Punchbowl whenever people enter a party or event on their Cozi calendar.

The basic agreement is that these other companies use their big distribution channels to get more customers to use Cozi’s free tools, while Cozi drives advertising sales for those impressions—and shares the revenue from those ads with its partners. It’s a similar arrangement to Cozi’s existing partnerships with companies like Dell, Nestle, Gannett, MeadWestvaco, and Meredith Corporation.

“Cozi continues to establish itself as the way to help families manage the chaos of family life,” Cape says.

Indeed, the company has taken an interesting road to the present. Cozi was formed in 2005 by Cape and Jan Miksovsky, both ex-Microsofties. It moved its software from PCs to the Web—and more recently to mobile devices like the iPhone and Android phones—all the while chasing families as its main customers. It has weathered the current recession and now has some 3 million registered members, and 30 employees—up from 23 in March of this year.

Still, the company has a long way to go; it’s not profitable yet, and it has raised … Next Page »

Comments | Reprints | Share:          

I recently had a good chat with Robbie Cape, the founder and CEO of Seattle-based Cozi. We talked about some key issues in tech startups and entrepreneurship, as well as the deal his company just landed in April with computer giant Dell—one that is helping drive some much-needed business to his consumer-focused startup.

The basic idea of Cozi is free software to help families coordinate their calendars, activities, to-do lists, and chores, and stay in touch better. The Web-based service can be accessed on PCs, laptops, and mobile devices like the iPhone, Windows smartphones, and BlackBerry. The recent Dell partnership means Cozi’s software comes pre-loaded on Dell’s new Studio One 19 machines (its touch screen desktop). The companies also formed a partnership earlier this year in which Dell ships Cozi’s software on other types of PCs through its retail partners.

Cape, a 12-year Microsoft veteran, founded Cozi back in 2005, and the company released its first product in early 2007. The startup has raised some $16 million from angel investors, family members, and the media company Gannett. It now has about 1.5 million customers spread among half a million families worldwide. Cozi’s revenues come from co-branding relationships and direct advertising.

Within the challenging space of Web-based consumer software, Cape had some valuable insights to share. Here’s a quick rundown:

—On how the Dell deal came about: “When we decided to integrate into family life, we spent two weeks considering doing a hardware play,” Cape says. “So much of our vision was related to there being computers, flatscreens throughout home where people could access Cozi. For our first user experience in 2007, we built it to run on Dell Studio One. One of the first calls we made was to Dell. We were talking to the team who report to the CTO, and they said they were looking out 2-3 years. They were like, ‘This would be perfect for us, let’s keep talking.’”

—On the effects of Dell on Cozi’s business: “They’ve given us incredible exposure through their retail machines. They’re signing up 1,000 new family members a day,” Cape says. “Orders are a lot higher than they thought they’d be. Retail response has been phenomenal. We’re seeing signups come through the Dell Touch machine. I’m amazed at how much focus the Cozi application is getting. There are a variety of different apps on the machine—Cozi isn’t front and center.” As for how significant Dell is to … Next Page »

Comments (2) | Reprints | Share:          

Boston’s Spring Partners, a venture-backed Web software startup founded by five former executives from mobile marketing firm Third Screen Media, announced today that it’s opening beta testing of its first product, Springpad, to the general public. Springpad is a Web-based personal information management system that helps users create annotated lists or “notebooks” around dozens of themes such as pet care, prescriptions, holiday gift planning, receipts, and recipes.

Comments | Reprints | Share:          

Bedford, MA-based TimeTrade, which makes a personal appointment scheduling system called TimeDriver, is expected to announce tomorrow that its software has been integrated with Salesforce.com’s suite of Web-based customer relationship management applications. TimeDriver for Salesforce will be unveiled next week at Salesforce’s DreamForce conference in San Francisco and will be available to users of Salesforce’s Force.com AppExchange by the end of the year, the company will announce.

Comments | Reprints | Share:          

Waltham, MA-based Commonwealth Capital Partners is the lead investor in a $5 million Series A venture round for Tungle, a maker of free Web-based calendar groupware, the Montreal-based startup announced today. Existing investors JLA Ventures and Desjardins Venture Capital also contributed to the round, which will be used to—you guessed it—”accelerate the company’s marketing and engineering activities.”

Comments | Reprints | Share:          

You get home from a big business trip to San Francisco, you’re talking with a friend from out of town, and you find out that he was just there too. If you’d known, you could have met up! It’s a common scenario—and it shouldn’t happen as often anymore.

After all, you probably keep an electronic calendar that includes details about your upcoming trips. And most calendars these days allow you to share your appointment data with other people’s calendars, over the Web or corporate networks. There ought to be a central exchange where your calendar program can go to find out whether any of your friends (or colleagues, or potential clients or customers) are going to be in the same area as you at the same time.

Well, now there is. It’s called LuckyCal, and it’s being built by a Lexington, MA-based startup that’s one of the first 10 companies to receive a grant from Facebook’ $10 million “fbFund.” Announced last year, the fbFund is run by Facebook with money from Accel Partners and The Founders Fund, and is designed to support independent developers working on applications for the Facebook Platform (the subject of my interview last week with Facebook senior platform manager Dave Morin). LuckyCal got the largest possible grant from the fbFund: $250,000, to be doled out in installments as the startup meets usership milestones.

But, while LuckyCal’s Facebook application is an important part of its offerings, you can use the service even if you don’t have a Facebook account, by giving it access to your desktop- or Web-based calendars and address books and inviting friends to share their own data. LuckyCal’s matching algorithms suck in all this information, along with public event listings from sources such as Ticketmaster, and spit out what the company calls “lucky” events: confluences that you can then decide whether to act upon. Say you’re going to Minneapolis-St. Paul next weekend. LuckyCal might see from your address book that you have a cousin there, and suggest that you give her a call; and it might know from the interests you’ve listed on your LuckyCal profile that you love public radio, and send you a link to purchase tickets to a live broadcast of “A Prairie Home Companion.”

When I first heard about LuckyCal’s service, it reminded me of 1990s-era predictions about “intelligent agents” that would scour the Internet, making your travel arrangements, negotiating appointments, doing your holiday shopping, and the like. A full-blown agent would require a level of artificial intelligence that’s still way beyond what computer science can accomplish. But LuckyCal does something very similar, just by crunching together the standard data that can be extracted today from productivity applications like Outlook and iCal and Web platforms like Facebook and Gmail.

It’s a no-brainer, in a way. But nobody had done it. “Calendars have been around for a very long time,” observes LuckyCal’s 37-year-old CEO and co-founder Sanjay Vakil, a Canadian-born entrepreneur and software architect who’s a veteran of local startups like Ambient Devices and PatientKeeper. “Electronic calendars have been around for a reasonably long time. And online calendars have been around for 8 to 10 years now. Yet nobody has tried to do this—to solve the simple problem of ‘Here’s where I’m going, show me what’s available while I’m there.”

Facebook, where members are already eager to make connections, is an obvious place to try out the model—and so far, a couple hundred Facebook users have signed up for LuckyCal. But ultimately, Vakil sees the software as something that could go beyond the social-networking crowd to become a money-saving tool for big organizations whose employees travel regularly. The fbFund grant comes at a key moment, helping the startup get its idea working first in a friendly environment (and perhaps helping it to earn a bit of money on Ticketmaster commissions along the way). But long-term, Vakil says, the business model is more about licensing LuckyCal’s services to big corporate customers.

Vakil says he’s been thinking about better ways to interact with event information for several years—ever since he worked at Ambient, a Cambridge, MA, startup that sells wireless information displays such as the Ambient Orb, which glows red or green according to the direction of the Dow Jones Industrial Average, and the Ambient Scorecast, which shows the progress of baseball games, hit by hit. (Vakil wrote the code for the latter device.)

“LuckyCal came out of a meeting with David Rose,” Ambient’s director and chair, Vakil says. “We had this idea for the Ambient Clock—a device that would take calendar information and show it on an analog wall clock. If you had an appointment between 2:00 and 3:00 it would fill in that pie piece. But we looked at the data real people put into their calendars, and on average it’s only about one event per day. What do you do with the rest of the clock? Why not try to … Next Page »

Comments (1) | Reprints | Share: