Path 2 feels like one of the most lovingly crafted apps I’ve used, with nifty animations and careful attention paid to quickly surfacing what information a user is likely to include in a post. For instance, the app has a spring-loaded composer button for creating and sharing content that’s just a really cool and efficient experience (pictured below, but you’ll need to use it to see what I mean).

When it first launched a year ago, Path wasn’t much of a social network — users could only share with 50 people, there were no comments or even ways to share photos to Facebook — and it didn’t do anything as a mobile photo app that was different from the zillions of other options. It wasn’t a failure, but it only got about a million users, less than might be expected for such a high-profile app.

The new version of Path (for both iPhone and Android) also doesn’t offer any feature that you can’t get from other tools like Foursquare, WakeMate, SoundTracking, Facebook and Instagram, but it combines them all into one sleek interface for telling people what you’re doing.

Path has smoothed some of its awkward friending stuff out — now you can connect to 150 people, and you can friend them instead of just sending them your content. But the new app adds some more implicit and automated interactions that make it so you’d really only want to use it with your closest friends and family.

In fact, Path CEO Dave Morin says he prefers to call users’ Path connections “loved ones” rather than “friends.”

For instance, if you open Path in a place you don’t usually use the app, it will automatically send out a location update about the neighborhood where you’re located. Or if you visit other users’ profiles, they each get an in-app notification saying you came by. If you click on a song someone’s shared, you see who else has ever played it.

And yes, you can even tell the app each night when you go to sleep and then reach for it first thing to show it you’ve woken up, and all that is dutifully recorded on your profile. (Eventually Path wants to integrate with more precise self-tracking tools.)

This is the kind of sharing that would only be OK with loved ones; for anyone else, it would be more like stalking and/or inviting yourself to be stalked.

In multiple ways, the new Path echoes the latest features announced by Morin’s former employer Facebook. Each Path user now has the option to set a “cover photo” as the background of their profile, and all this automated sharing has a parallel in Facebook’s new “frictionless” tools for developers like Spotify.

Do we really want to automatically spray out updates about everything we do? Morin thinks so — but he argued it makes more sense in a private and mobile setting like Path than on Facebook.

Crowded Room — which was developed inside of the mega-Internet conglomerate IAC and is available for iPhone, Android and HTML5 — fits into the category of social discovery apps. It helps users find people to befriend and date, based on the venues they check in at and plan to go to.

Crowded Room users — who are generally shown with a profile picture, first name and age — get a personalized list of suggested people and recommended venues based on their history and interests.

Users can indicate their future plans with a “might go” button, which is intended to build critical mass around meeting up at a certain spot. (Other apps — like Ditto, which hasn’t really taken off — have tried similar ideas of future check-ins.)

Crowded Room users can also “shortlist” each other, which is kind of like privately indicating you have a crush on someone. If two users both put each other on their shortlists, they get a notification.

In related news, I recently wrote about Proust, a social journaling service also out of IAC.

Many industry pundits have talked about the Consumerization of the Enterprise — the idea that enterprise users expect the mobility, integration and ease of consumer technologies in their work lives. People often cite the move to user-purchased mobile devices like the iPhone or user-provisioned collaboration services like Box, DropBox and Yammer as evidence of this phenomenon. And because many of these services have freemium models, IT departments are finding that huge numbers of their employees are already using these services for business purposes in addition to personal ones. So in many ways, consumer expectations are driving the ways enterprise CIOs think.

But what about the other side of the phenomenon? Eddie Murphy’s character Billy Ray Valentine influenced Dan Aykroyd’s character, Louis Winthorphe, III, as much as the reverse. What’s less discussed — but equally fascinating — is the impact of enterprise requirements on the consumerization trend.

Many of the aforementioned start-ups initially focused entirely on end-user needs, providing simple user interfaces and sign-ups, and building multi-million user customer bases in the process. But as these vendors switched focus from user acquisition to monetization, they realized some IT department requirements are legitimate, and more importantly, are barriers to sale.

The most recent example: Box. Box founder Aaron Levie probably never imagined his company would be working with enterprise IT directors in designing his product roadmap when he started his file sharing company, but nonetheless it recently announced partnerships and integrations around identity federation, mobile security, e-discovery, and other IT-centric areas.

In contrast, DropBox has continued to focus heavily on end-user adoption with limited IT focus. Indeed, their total reported user counts dwarf those of Box or any other service. Yet the CIOs I’ve spoken with had a proliferation of users on DropBox and Box when they decided to standardize on a collaboration service. Despite the fact that their companies may have had more DropBox users, Box’s enterprise functionality tipped the scale in its favor. So while user adoption gets you in the door, without some enterprization you don’t get the sale.

Similarly, for Google’s Enterprise team, bringing Gmail to companies involved a lot more than just learning how to charge for the service. Google has spent the past several years trading places with Microsoft, investing in policy management, security, compliance and other IT-centric functionality to address early inhibitors to adoption. And it has worked. Analyst firm Gartner now sees Google as a viable alternative to Exchange for enterprise collaboration.

Indeed, even in the truly consumerized world of mobile devices, iPhones and Androids don’t roam free in most large companies. Many security-sensitive organizations are investing in Mobile Device Management (MDM) solutions like those from Good, MobileIron, Zenprise and Symantec, to bring enterprise manageability to smartphones.

The Enterprization of these traditionally consumer apps is going to center around three legitimate enterprise requirements:

1. Data ownership: While enterprises are excited to leverage the flexibility and fluidity of cloud apps, the idea of an enterprise’s intellectual property spread across hundreds of cloud services, many times in user-provisioned accounts where the enterprise has no access, is scary. What if the company is involved in a lawsuit and has to put a user’s data on legal hold? How can the company recover data if the cloud service loses it? And most importantly, how can the company get its data back if it wants to change services? Tough questions if the data is trapped behind a user’s personal cloud account.
2. Data security: Similarly, the thought of sensitive customer information living in cloud accounts where users choose passwords like “password” or, for the more secure, “password1,” is nerve-wracking to a security officer. How can the company ensure that its data is protected with strong passwords? When an employee leaves, how can the company revoke access to all cloud apps at once? Without company administrative rights, the enterprise is dependent on the judgment of the user.
3. Data compliance: Whether data is stored on your G:\ drive or in Gmail, if it’s work-related, for the most part the same compliance rules apply. While SOX, FRCP and GLBA are not as sexy as FourSquare, Angry Birds and AirBnB, they are still critical for most companies. How can companies meet regulatory requirements around searchability, records retention, logging and other areas?

The real challenge as start-ups address the needs of enterprises is to maintain the core value that earned users in the first place. If they add every feature IT asks for, will the products lose their usability? If they make it easier to lock down access to the systems with two-factor logins when you can’t remember one factor, will users revolt? If these tools were used to get around IT, will the fact that they can now be monitored scare users away?

Time will tell. But this grand experiment would make the “Trading Places” brothers proud. And a lot more than $1 is at stake.

Nick Mehta is CEO of LiveOffice and has served in senior operating roles in the enterprise and consumer technology markets for much of his career. He spent more than five years at Symantec Corporation and Veritas Software Corporation (now Symantec), where he served as vice president and general manager of the Enterprise Vault information archiving and discovery software business.

Google+ VP of Product Bradley Horowitz replied in an interview yesterday: “We will compete on features — including simplicity. We are absolutely in a feature race, and I think we will run that race.”

Technology companies tend to talk about how innovative and incomparable their strategies are, so that’s a pretty rare admission.

Horowitz added, “If I had to say what fraction of Google+ is launched right now, we’ve just got the very basic foundation in place. Profiles, circle editor and stream, that’s sort of the minimum viable set of features that you need to start doing interesting things.”

I talked to Horowitz in advance of his appearance at our AsiaD conference next week, held Oct. 19-21 in Hong Kong. He said to expect new stuff to be announced there. In fact, he said to expect new features to launch every week through the end of this year — for instance, see today’s real-time search announcement.

As for whether Google+ usage is fluctuating or falling, as many watchers have speculated, Horowitz brushed them aside, saying external measurements can’t grasp the “dark matter” of Google+.

This dark matter consists of private sharing, which continues to account for two-thirds of all Google+ activity. In fact, Horowitz said, that number is “trending slightly up.”

Horowitz asked for observers to have a little patience while Google+ is being built, saying the project was never intended for such a large audience or so much scrutiny at this stage.

Shortly after I spoke with Horowitz at Google’s campus yesterday, Google engineer Steve Yegge published a scathing critique of Google’s lack of a platform strategy that was particularly hard on Google+, calling it “a knee-jerk reaction, a study in short-term thinking, predicated on the incorrect notion that Facebook is successful because they built a great product.” Yegge later said the post was intended for internal eyes only, but in addition to critiquing Google+, he apparently also had a bit of trouble using the site, and accidentally posted his manifesto on his public Google+ page. Google declined to comment on Yegge’s post.

Since Yegge’s critique wasn’t out when I visited Google yesterday, I wasn’t able to ask Horowitz what he thought of it, but his responses to my various questions might help fill in the gaps. First, Horowitz does think Google+ is a larger platform play rather than just a product, in that it will be a layer on top of all of Google’s products. And second, his team severely “underestimated the appetite for this product,” and it is currently rushing to push out all sorts of things users are asking for, as well as other stuff they haven’t anticipated.

I’m not sure those answers would suffice for Yegge, who would have preferred that Google have invited developers to be part of Google+ from the beginning, so that it could reap the benefits of being a service-oriented platform, as Amazon has through its Amazon Web Services for other developers.

Still, Yegge’s key examples of platform companies, Facebook and Amazon, only built their platforms after they had success with their own products — a social network and an e-commerce site. While some companies, like Foursquare, build their own products on top of their APIs, the usual pattern is product first, platform later.

Anyways, enough with a phantom argument between two people who work at the same company!

In my interview with Horowitz yesterday, I asked whether he thinks people are using Google+ because it’s an alternative to other social networks with a more precise structure for sharing.

“I think in the early going there was a lot of looking for an alternative,” Horowitz replied. “But I think increasingly the people who are using Google+ are the people using Google. They’re not looking for an alternative to anything, they’re looking for a better experience on Google.”

This idea of Google+ as a utility might be expressed as a button on Google Maps that helps a user send directions to attendees of a party, Horowitz said.

So does that make Google+ just a utility on top of the Google products people already use?

“That’s one rendering of it,” said Horowitz. “But there’s a stream, there’s a circle, a profile, there’s Hangouts, there’s games. It is both a means of communication and a destination.”

Zynga unveiled a slate of new products today, and mobile was a central theme.

In addition to announcing a new online games platform, three new Facebook games and one new game on Google+, Zynga also revealed five mobile games.

Three of the games — Zynga Poker, Words With Friends and FarmVille Express — will utilize HTML5 technology and run on Facebook’s iPad app and mobile Web sites. Those games are expected to launch tonight.

A fourth game is Mafia ShakeDown; the fifth is Dream Zoo, a standalone mobile game that is Zynga’s first zoo-themed game.

Dream Zoo will challenge players to pet, feed, bathe and breed all sorts of animals, from rainbow giraffes to polka-dotted flamingos and electric-green elephants.

In an interview at Zynga’s event, Chief Mobile Officer David Ko told me it will be the first time Zynga is incorporating location-based check-ins — similar to Foursquare or Facebook Places — into a mobile game.

He said the game will rely on Facebook’s data, allowing users to check in based on where they are playing the game.

In a follow-up interview, Ya-Bing Chu, the general manager of Words With Friends, told me users will get rare items in the game for going to a particular location, but generally, Zynga will be experimenting to see what users end up liking.

In the game, players will be expected to complete expeditions, but he said you could envision how that could overlap into real life, like going to a city park or even a real-life zoo. ”We aren’t sure what will work,” he said.

Zynga’s mobile announcements today can be considered a major push, given that Zynga has been slow to roll out aggressive plans in mobile. Dream Zoo and Mafia ShakeDown are expected to launch shortly.

Here’s USV principal’s Fred Wilson’s comment, via email: “Union Square Ventures is very fortunate to be able to add Andy Weissman to our partnership and we think he is a perfect fit for the entrepreneurs we want to work with and the sectors we want to participate in.” (More below.)

That will cause a small ripple in startupland, because Weissman was the one steering Betaworks’ investment portfolio. His partner John Borthwick handled the operational parts of the business, which has founded and/or nurtured startups like Summize, TweetDeck, Chartbeat and Bitly.

With Weissman’s departure, Betaworks’s focus will change. “Though we will continue to do seed stage investments, our primary focus will be on building the core capabilities of the companies that we acquire and grow in-house,” Borthwick said told his employees via email today. Betabeat first reported the news.

What Borthwick didn’t explain in his email is that he and Weissman had previously planned on raising a “sidecar fund” that would essentially split Betaworks into two businesses: An operating company run by Borthwick and an early-stage VC shop run by Weissman.

But that plan was discarded this summer, at least in part because of opposition from Betaworks’ investors, who include RRE Ventures, Intel, AOL and the New York Times. Investors argued that they had put money into a company where investing was only a component of the plan, not a full-time occupation; by raising a new investment fund, they argued, Betaworks would essentially be competing against some of its backers.

People familiar with the company say that the plan’s collapse didn’t lead directly to Weissman’s departure. But the backstory does provide context to his move to become a full-time venture capitalist.

When Weissman lands at Union Square, he’ll have plenty of money to work with. The firm, which has made a series of lucrative bets in high-profile Web 2.0 start-ups including Twitter, Zynga, Foursquare and Tumblr, is in the midst of raising a new $150-$200 million fund.

Four-year-old Betaworks, which now has more than 80 employees, ought to have plenty of money to work with, too. In addition to the $28 million it has raised to date, the company has also been able to turn some of its investments into cash via secondary market sales.

Most notably, it has recently sold Twitter shares it acquired in 2008, when the company bought search engine Summize. That alone should provide a nice cushion for Betaworks if it needs it: Twitter’s value has shot up from $100 million to $8.4 billion over the last three years.

And speaking of ripples, here’s one I’m guessing Weissman may enjoy:

Instead of checking in, Gowalla users will now create “stories” when they meet up to hang out together. These are basically group check-ins, as on Facebook where a user can tag multiple friends at a place. After that, any tagged person can contribute photos and other content to the story, capturing it as a communal experience.

On the flip side, visitors (who don’t even have to be logged in) will be able to visit Gowalla to see local guides that are aggregated from their friends’ “stories,” as well as highlights from local users and content from sponsors and partners. Gowalla is seeding the service with information on 60 cities that will be dynamically updated with new user entries from within their geographies.

As soon as its new app gets approved, Gowalla will be relaunching with upgrades to its iPhone, Android and Web versions (though users can continue to check in through the old versions).

Gowalla CEO Josh Williams said in an interview today at the TechCrunch Disrupt conference that he’s interested to test his hypothesis that “social content has value to observers.”

But don’t call it “the ‘p’ word — a pivot,” Williams begged. “It’s not like we’re doing a music streaming service!”

What might be difficult about this transition is that Gowalla is setting itself up to serve two separate audiences: Content creators and content consumers — groups whose interests and motivations may be quite different. For instance, I could see the new Gowalla guides being really interesting when I travel, but perhaps less so in my home city. There will also be a delicate dance between aggregating public “stories” and those that are published to friends only.

Williams said Gowalla has about two million registered users, with hundreds of thousands of them having used the service in the last couple weeks.

CityPockets, which is only about a year old, is acquiring the company in an all-stock transaction. As part of the deal, DealBurner founder Jason Fertel will become director of engineering.

Both Groupon and LivingSocial are pushing aggressively to roll out offers that can be purchased and redeemed immediately, rather than having to wait a day. Currently, users must search for offers, rather than having deals pushed to them automatically, based on their location.

Today, CityPockets lets users manage their daily deals purchases in one place, whether they were bought from Groupon, LivingSocial or any of about 30 other providers. In April, it launched a marketplace that allows people to sell deals that they are unlikely to use.

Co-founder Cheryl Yeoh said that with the addition of DealBurner, the goal will be for users to be able to buy those unwanted vouchers on the go, and use them immediately for a restaurant or spa they might be visiting — whether it’s new or something someone else bought but won’t be using.

“I see it going to a more mobile solution, where you can buy and redeem instantly, rather than having to wait for a day. It’s the aggregation of past, present and instant,” she said.

Yeoh said DealBurner will aggregate the secondary marketplace with offers from both Groupon Now and LivingSocial Instant, which are the company’s respective marketplaces for same-day offers.

If you sign up for DealBurner and link your Foursquare and other check-in services to the app, it will send you a text message when one of these deals is available for your location, eliminating the need to have to manually open multiple applications and look for deals around you.

Foursquare and other services are already aggregating offers and showing them in their apps. Yeoh says CityPockets isn’t trying to compete with Foursquare, since it is trying to be a more comprehensive service.

Yeoh says CityPockets currently has 100,000 vouchers loaded into its system, with a cumulative value of about $5 million. She said that the average user has purchased 24 deals, of which nine are unused and still valid. That’s way above the four deals that Groupon reports as the average for its customer.

Yeoh launched the company with Jhony Fung at LaunchBox Digital’s Fall 2010 incubator program and has raised $750,000 from Great Oaks Venture Capital. With the addition of DealBurner’s Fertel, there will now be five employees.

That’s not a novel idea, but it may be a well-timed one: A new start-up called BuzzMob today is launching an iPhone app to help users meet and interact with people around them.

Irvine, Calif.-based BuzzMob’s approach is this: Users create “Rings” around geographical areas — from a single building to a three-mile-wide area. That place gets a virtual wall that includes a live stream of posts, tips and pictures from users who are in the location (as validated by GPS) and join the Ring. Rings can be public or password-protected.

There’s no notion of a check-in like with Foursquare, which launched its own events feature last week, but rather a series of ongoing conversations around a place or experience.

BuzzMob doesn’t require real names, and in order to avoid the loneliness problem of similar products like Color, it allows users to view, but not participate in, Rings in other locations.

The eventual goal is that venues and event promoters will create their own Rings — though BuzzMob hasn’t scored any of those deals yet. The self-funded company’s app is also a little bit rough around the edges compared to competitors like Yobongo, LAL and Hot Potato (which was bought by Facebook and subsequently shut down).

According to LinkedIn, 87 of the 641 people who say they currently work at Twitter were formerly employed by Google. (Twitter said this week that it has 600 employees, so that number’s a bit off, but probably in the general neighborhood.)

Early Google employees don’t get as much credit as those of, say, PayPal, for founding and funding a new generation of start-ups. But former Googlers seem to have made a practice of infiltrating promising new tech companies as they look for the next big thing.

At one point last year, it was noted that 200 former Googlers worked at Facebook, making up 12.5 percent of its staff at the time, including top executives like Sheryl Sandberg and many of the product people Facebook brought in through acquisitions.

Something similar seems to be happening at Twitter, though it’s still much smaller. CEO Dick Costolo was with Google after it acquired his start-up FeedBurner (but some say that means he’s not truly born-and-bred Google). Co-founders Evan Williams and Biz Stone (both no longer in operational roles) were also formerly at Google, though again, Williams came in through an acquisition (of his Pyra Labs, which made Blogger).

The Google influence seems especially prevalent on Twitter’s product team. Satya Patel, who is director of product management, was formerly a well-respected Googler, and nearly every Twitter product manager seems to have had some history at the Plex — save for the four who were recently let go.

Twitter creative director Doug Bowman came from Google (in fact, he left in a huff), as did general counsel Alex Macgillivray and VP Katie Jacobs Stanton, who leads international strategy.

Glenn Otis Brown, Twitter’s newly added director of business development for media, was formerly products counsel at Google and head of music partnerships at YouTube.

Twitter spokeswoman Carolyn Penner, who herself came to Twitter from Google, said she could not provide any specific numbers about how many of her coworkers matched that description.

A Twitter insider said that Twitter’s Googliness is less apparent than Facebook’s, because fewer members of the core leadership team came from Google. Even if head honcho Costolo did stop through Mountain View en route to hipper San Francisco, execs Jack Dorsey (executive chairman in charge of product), Adam Bain (revenue), Ali Rowghani (CFO) and Michael Abbott (engineering) did not work at Google.

Google isn’t entirely happy to be spawning other people’s workforces. The company has famously paid dearly to keep its top employees from departing to take roles at Facebook, and more recently, Twitter. Twitter and Google have been partners in the past, but more recently have had testy relations over renegotiating a data distribution deal.

Thomas Korte, the ringleader of start-up incubator AngelPad and an early Googler, noted in a recent conversation that following former Googlers’ successful infiltration of Twitter, Square and Foursquare seem likely to be the next ex-Googler targets.

Korte pointed out that Foursquare recently hired the well-connected and respected former Googlers Morgan Missen and Benjy Weinberger (both actually worked at Twitter en route!) and Square recently appointed former Googler Megan Quinn as its director of products.

Besides the beginnings of strong referral networks, Korte added, these up-and-coming companies have one other thing going for them: “They’re the only ones that can cough up the salaries to match Google,” he said.

Groupon coupons — both daily deals and Groupon Now deals — started appearing today within the Foursquare “Explore” tab in its mobile apps, which helps users find interesting things to do nearby. They seem to have been first noticed by the independent blog About Foursquare.

A representative for Foursquare said the Groupon deals are available in Chicago today, and should be available for the rest of the U.S. and Canada by Sunday.

Earlier this month, Foursquare added five other daily deal sites: LivingSocial, Gilt Groupe, AT&T, Zozi and BuyWithMe.

Time will tell, but it seems likely users will be compelled by deals that are timely, targeted to their tastes and nearby.