First of all, good for Pinterest. Even though that kind of investment milestone is so rare it’s almost like winning the lottery, it’s inspiring and amazing to see startups achieve this type of success.

I’m sure we’re about to see a flood of articles and posts about if this is another sign of a tech bubble, if Pinterest is really worth that valuation, how they haven’t established a revenue model, how they infringe on copyright, and other various attempts to knock them down. It should be noted that these days, that’s probably a big sign of success to receive that kind of criticism.

The biggest implication of this though is that an investment at a $1.5B valuation means that Pinterest is virtually taking themselves out of being an acquisition target. For investors to get any sort of positive return on that money, they’re looking at a multibillion dollar deal. The only companies that have the cash and business fit to be interested at that price are Google and Amazon, and until Pinterest is generating a ton of revenue it is tough to justify for those companies.

There are a few more things I find interesting about Pinterest along with this news.

Not an overnight success

Pinterest has been portrayed by many as being an overnight success. In reality, it’s been a four year journey, although it’s quite true that it accelerated exponentially in the last year.
 

Pinterest is not a mobile-first company

A great deal of the “hot startups” lately are mobile-first companies like Instagram, and a lot of the startup advice is that mobile is the future. While mobile is obviously important to Pinterest and their future, the company originally pivoted from being an iPhone app to being a desktop-driven experience where it took off. How many times has that happened successfully?
 

Huge valuation without much technical difficulty

Don’t get me wrong, obviously there are technical challenges involved in scaling to the size of Pinterest, but their initial product was not a challenging technical problem. Like Instagram, they took something that was already being done by many other services but designed it better and made it a great experience. That IS challenging, but not for hardcore technical reasons.
 

Another Valuable Company Built on the back of Facebook

Facebook’s platform and access to the social graph has been a huge boon for many businesses. However, thus far Zynga is really the only company anyone can point to that really grew to a billion dollar company thanks to the Facebook platform. Pinterest may be the second company that can fit into that class now. While it’s not an app that lives inside Facebook, and you can sign up with Twitter or email, it’s clear that Facebook was a major piece of Pinterest getting viral exponential growth.
 

Where’s the revenue?

As I pointed out above, we’ll probably see many upcoming articles about Pinterest’s lack of revenue so far. But to be fair, they have barely tried. The product obviously has a very natural fit with ecommerce, so it will be interesting to see how they can profit from being the source of discovery for so many purchases.

Overall, raising an investment round like this does not mean Pinterest is assured long-term success. They need to keep innovating and pushing forward, but this investment should give them plenty of runway to go for it on their own and become an important independent company.

You can follow me on Pinterest as well.

Joe’s immediate reaction was “Would you rather have 200 $5 million dollar houses, or Instagram?”

A great question. For the record, I think Facebook paying $1 billion to take out their most threatening future competitor was worth it no matter what happens to Instagram within Facebook’s control. Just think about how better positioned Yahoo! would be today had it acquired Facebook for $1 billion back when they almost did a few years ago. Yahoo! could have either leveraged Facebook to massive success, or killed Facebook off and they’d still own more of the consumer and advertising market they’ve lost to Facebook.

Whether you agree or not, that’s still a lot of money. What could Facebook have bought instead of Instagram? Let’s explore…

1. 200 $5 million houses in Palo Alto
2. 1,000 $1 million houses
3. A used B-2 Bomber
4. The New York Times Company (valued at $967 Million)
5. All 66 of the most recent YCombinator Startups (gotta be a breakout startup in there right?)
6. Yahoo!’s Core US Business
7. AOL’s Patent Portfolio
8. All the Facebook Mafia Companies: Path, Quora, Asana, Causes, GoodRx
9. Yelp (when the stock drops a little)
10. Every other mobile photo or video sharing application
11. Pinterest (maybe)
12. Foursquare
13. AppNexus
14. Spotify
15. Rovio (Angry Birds)
16. Gilt Groupe
17. Tumblr
18. 2 million of the New iPads
19. Myspace, Friendster, Orkut, Bebo, and you’d still have about $990M in cash leftover
20. The San Francisco 49ers (change name to San Francisco Likes)
21. A small country (How about the Maldives?)
22. A $20,000 hotel room every night for 137 years
23. Ten $100M yachts (one for each of Zuckerberg’s direct reports!)
24. Pay for 48 hours of the military activity against Afghanistan and Iraq
25. Send a $20 bill to all 50 million Instagram user bribing them to use Facebook’s mobile app for photo sharing

If you were Facebook, would you buy any of those things instead of Instagram?

Another album and a couple of years of solid listening later, including an amazing live concert at Edgefield near Portland, and I’m still as excited about Bon Iver as ever.

While it’s not the full band, this live session of Justin Vernon and bandmatte Sean Carey intimately captures how amazing they are. It’s the kind of thing you watch and just wish you had that kind of talent. Enjoy.

Post Summary:
We just launched a new web experience for Fantuition. Check it out and play some of our prediction games for topics you love. For the back story on Fantuition, keep reading…

A Change of Course
About a year after starting up a company to take on the problem of local recommendations called GuideMe, it became clear that we hadn’t generated the amount of user traction we had hoped and we didn’t have the path to get there. We made the decision to end our development on GuideMe in September.

Even though GuideMe as a product had failed, the team and our great investors still had a desire to work together and take another crack at a different problem. We took a step back and opened our eyes to look at numerous problems and opportunities that could have been interesting to pursue. However, I couldn’t get past one idea that had been in my mind for a few years.

The Problem
Everyone who knows me is aware that I’m a big sports fan, and more specifically an Oregon Ducks fan.

Over the years I’d played fantasy football/basketball/baseball/golf, various pick’em games, March Madness pools, and other assorted games. Like many sports fans, these fantasy games provided me an additional way to engage with the sports I was already watching.

All was not perfect though, as I found that there were two major problems for me with the fantasy sports experience.

1. Amount of Time Required – In order to succeed at most fantasy games you need to spend a significant amount of time researching players, analyzing matchups, scouting the waiver wire, reading news, and managing your roster. Some players who have a lot of free time actually enjoy this, but there is a large percentage of fantasy players who don’t have the time. Additionally, so many sports fans I know don’t play fantasy sports specifically due to this time commitment.
2. Caring About All Teams – The other major issue I’ve had with fantasy sports is that while I follow the full league action, I tend to only focus and watch the teams I actually care about. For example, in the NBA I primarily follow the Portland Trailblazers. When I play fantasy basketball I will have 0-1 Blazers on my fantasy team, which really doesn’t tie into my personal fan passion for the team.

The Solution
These two frustrations led me to question why there wasn’t a simpler game to play that could also be focused on specific teams. Why can’t I play a game based on just the Oregon Ducks or the Portland Trailblazers? And why can’t I play with more than just nine other people in my league?

Obviously a simpler game focused on one team wouldn’t work in the traditional “manage a roster” fantasy format, and I wanted something that required less time, so the game itself needed to be totally different.

In thinking deeper about this, it became clear that fans of a specific team talk about and predict a pretty consistent set of questions. Who’s going to win this weekend? What’s the final score going to be? Which player is going to have a great game? Player X had a great game last week, will he keep it up?

Turning these questions into a game seemed to make total sense to me. We’re already talking about these questions with each other, so let’s actually compete around who can predict the upcoming game the best!

This basic idea to create a simple prediction game for specific teams had been rolling around in my head for a few years. I wanted to make it quick, fun, social, and let people feel like they are engaging with their team and fanbase. However, it had never gotten past the concept phase.

When the opportunity to revisit this idea came up after shutting GuideMe down, the changed internet landscape had seen casual game success and monetization, the rise of mobile time killing, and “2nd screen” mobile usage for TV watching. The time seemed ripe to strike, and with the additional ideas from our investors and Joe (the rest of the team) we quickly built a mobile web prototype called Fantuition in late October.

It was clear right away that playing Fantuition in a very basic form for Oregon Ducks Football was a lot of fun for us and our close friends. We cared more about the games we were watching, we could discuss our predictions socially, and we were learning more about our favorite team. It wasn’t long before people we didn’t know were signing up, and users were suggesting that the format would work for other sports and their favorite reality TV shows.

Fast forward a couple of months and we’ve got a lot more users, a third employee, a number of different games going, a full website, and a ton of ideas about where to take the product and games that we need to go execute.

The ability to play casual social games about all the teams we care about, the reality TV shows we watch, and the award shows or other non-scripted special events we attend needs to exist. So we’re building it.

Give the new Fantuition site a try and send us some feedback.

It was an amazing game against Wisconsin, and the Ducks continued to push the envelope with their explosive offense and style. Great season. Go Ducks!

One of the biggest problems with photo sharing apps so far is that they all tend to only allow you to share one photo at a time. While this keeps the quality of photos shared high, it creates some problems.

It’s a painful process if you want to share multiple photos from an event, as part of a theme, or just to get photos off your phone and put them in a place they can be shared without the painful process of downloading them to a computer and then uploading them somewhere.

Tonight Mike Arrington broke the news that the team at self-photo taking startup DailyBooth recently launched a photo sharing app called Batch for the iPhone.

I downloaded Batch and immediately loved it for the following reasons:

• The design is beautiful. I love the handwritten instructions that overlay the screen in certain areas, and it walks you through how to use the application really well.
• Uploading photos in a batch is great. The first time I got to touch multiple photos and have them uploaded at once I saw the value in the speed and simplicity of sharing the photos in a batch.
• Automatic friend connection via Facebook makes it nice to not have to worry about building up my social graph. As friends join Batch, we’ll just get connected. Simple. This has some downsides in that you can’t customize who you follow or don’t follow yet, but I prefer it over having to start from scratch and manually choose everything and hope my friends find me.
• You can see the future potential if batches from one event or location are grouped automatically and viewable together. It could nicely fulfill the promise of Color that never came to be.

If you have an iPhone and share photos, give Batch a try in the app store.

Every entrepreneur and investor takes something different away from shutting down a company. I’m glad to see more people are choosing transparency and dialoge to share unfiltered experiences and extract lessons to be learned. The startup ecosystem is better off as a result. – Bryce Roberts

I posted recently about how much there is to be learned from the stories of startups failing. As investor Bryce Roberts from OATV points out, this postmortem from former OATV investment GameLayers is very detailed with a wealth of knowledge.

There’s personal stories, videos, pitch decks, charts, and pictures that really take you through the ups and downs of the GameLayers startup experience. It’s definitely a worthwhile read.

There’s been numerous news reports about Google considering “buying” Yahoo!, or at least teaming up with private equity companies to do so.

While most of the articles at least mention in passing that it’d be unlikely for this to pass government review, I haven’t seen many people actually discuss why Google is involved.

Why wouldn’t a Google acquisition of Yahoo! pass government review? Well, if the Department of Justice wouldn’t pass the search deal that Google and Yahoo! worked up in 2008 where SOME of Yahoo!’s search results were powered by Google, then why would they actually let Google take part in buying all of Yahoo!?

In fact, many thought that Google knew in 2008 it wouldn’t pass government review, but tried to do the deal just so Yahoo! would turn down Microsoft and waste a lot of Yahoo!’s internal time (and it worked). I sat in many meetings at Yahoo! that were spent talking about the tests we were running with Google and how we were going to implement the deal.

There hasn’t been enough change in search market share for anyone to seriously even think it could pass. I’m not entirely sure if Google being only part of an ownership group with private equity firms would change the government’s view, but I doubt it.

Which leaves us asking, why is anyone even taking Google’s interest seriously?

I can’t answer why anyone is taking Google seriously, besides the fact that they are one of the only players who actually have the cash to do something around Yahoo!.

It just seems like any major involvement on there part is going to just raise big red flags with the governments of the world and will never pass “go”.

Why would Google get involved then?

I feel like there are two obvious answers to this one.

1. Google can pretend to at least have interest in Yahoo! to draw out how quickly something happens here. The more time Yahoo! is in limbo, and the more time Microsoft spends figuring out what to do about it, the better that is for Google to continue to separate itself from them.
2. Google can go as far as even floating prices out there to try and get others (Microsoft) to feel like they have to pay more in order to get Yahoo!. The more money someone spends on Yahoo!, the better that is for Google.

I suppose it is possible that Google really does want to keep Yahoo! out of Microsoft’s hands, but it seems like Microsoft having to acquire and digest Yahoo! would just allow Google to accelerate ahead even further ahead. It’s all just a ruse to waste time by complicating matters and drive up the price. Well played Google.

Kudos to Gabriel for being open and sharing his fundraising experience.

At the recent TechStars Demo Day, Gary Vaynerchuk spoke about his concern with the current trend of celebrating the startups who raise money.

It’s easy to understand why the media, investors, and us all as individuals in the startup/tech world tend to focus on the stories of fundraising and hot startups. It’s positive, exciting, and it fuels the dreams of so many involved.

Gary’s point seems to be that we should celebrate the startup that knows how to make money instead of raise money. It’s a good point, but I think when startups make money at scale that’s celebrated quite a bit by everyone.

The problem I see is that these stories paint a picture that everything is great out there in startup-land, it’s easy to raise money, and that if you follow some simple steps you can also raise money and get on Techcrunch.

Besides the inaccurate picture that’s painted, there’s frankly not much to be learned from hearing about a hot startup with a strong team, that’s executed their product well, and raised money from A+ investors. While it’s a feel good story, there’s not much in that story that’s easy to learn from or duplicate.

Where there is something to be learned is from the startups that aren’t making it. The startups who are not finding product/market fit, the ones who can’t raise money, who are having team problems, or are failing for some other reason.

I’ve learned far more from the few startup postmortems that founders have posted than I’ve learned from the thousands of “Startup X raises investment” stories that have been published this year.

These stories are somewhat hard to find, as founders are often less excited to publicly talk about their failures. However, it’s also because there is no publication that’s really giving these companies and founders a voice.

The solution is a blog that specifically covers startups that have failed, are currently struggling, or that were on their way down before pivoting to find success. This isn’t meant to be a site that gossips or mocks these startups like F—edcompany.com did back in 2000, but one that seeks to pull out the lessons to be learned and positive experiences that can be drawn from them.

I’m tempted to start such a blog, but I’m busy working on my own company and don’t need the additional distraction. Who’s up for building a publication that could be very valuable for the good of the tech world?