Entrepreneur and startup advisor Eric Ries yesterday wrote an impassioned blog post at Startup Lessons Learned asking startups and other companies to “stop lying on stage” about their accomplishments, and to be more honest about their failures. Among other things, he mentioned a blog post last week from Wesabe co-founder Marc Hedlund that went into detail about why the company failed and its competitor (Mint) succeeded. Now Ries’s plea has sparked another failure post-mortem, from Standout Jobs co-founder Ben Yoskovitz, who wrote a post today about his company’s shortcomings.

Yoskovitz, who has since become the co-founder of a Montreal-based seed fund/incubator known as Year One Labs, sold the job-related startup he founded with investor and entrepreneur Austin Hill in May for an undisclosed price, but makes it clear in his post that the company more or less failed to achieve what he had hoped to achieve. Why? The founder names several factors, including:

• Bad timing. “Our timing was terrible. We launched the paying version of our application in the fall of 2008 about 5 minutes before the economy collapsed.”
• Not fast enough. “I had an exceptionally strong team… but in reality we didn’t code and launch fast enough. We didn’t get product into customers’ hands fast enough.”
• Too much money. “Raising the money felt like winning. It felt like all (or most of) the justification we needed. It set us on a path of building a bigger product than we should have, and committing (falsely) to our own assumptions of what would work, without fully testing them.”

Yoskovitz also mentions that he didn’t make it easy enough for users to do what they wanted to do with the site, in part because Standout Jobs was trying to change user behavior in ways that the company thought would be better. The reality is that most users don’t like to change, and Standout Jobs didn’t manage to convince them otherwise. Marc Hedlund mentions a similar point in his post-mortem: Despite being first to market, and being revenue-positive, Hedlund says Wesabe failed because it simply made things too difficult and complicated for users, while its competitor Mint made them very simple, and simple almost always wins.

Another point the Standout Jobs founder mentions is that he didn’t have a strong enough understanding of the market he was attacking before he launched the service. “I see countless entrepreneurs make the same mistake,” he says. “They look at a market objectively and think, “I can fix that!” only to realize when they get neck-deep into it that there are a whole bunch of issues they didn’t understand.” As it turns out, this is almost the exact same advice given by Paul Biggar in another recent startup post-mortem — a post about the failure of NewsTilt earlier this year — when he admits that he didn’t really know much about the market he was trying to fix.

Final word goes to Marc Hedlund:

You’ll hear a lot about why company A won and company B lost in any market, and in my experience, a lot of the theories thrown about — even or especially by the participants — are utter crap. A domain name doesn’t win you a market; launching second or fifth or tenth doesn’t lose you a market. You can’t blame your competitors or your board or the lack of or excess of investment. Focus on what really matters: making users happy with your product as quickly as you can, and helping them as much as you can after that.

If you want to explore some more examples of the startup post-mortem oeuvre, ChubbyBrain has put together a list (hat tip to Paul Kedrosky for pointing that one out) that includes an analysis from investor Roger Ehrenberg about why one of his startups failed, as well as founder Scott Rafer’s post-mortem on the failure of Lookery (which he blames in large part on an over-dependence on Facebook). In a nice touch, Chubby Brain has even included its own failure post-mortem as part of the list.

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Post and thumbnail photos courtesy of Flickr user Alex Proimos

I’m constantly surprised at the cutely obvious names of some web services – finding a brand name that’s sublimely obvious but if successful is very likely to be as linguistically ubiquitous as ‘googling’ or ‘hoovering’. Shoeboxed may just well be one such brand – I wonder if in five years time, we’ll be ‘shoeboxing’? Infact, most of us probably already are…

Launched around a year ago, Shoeboxed provides a simple service for uploading, storing and organizing all those paper receipts that are stuffed into real shoeboxes around our homes and offices, into over-sized wallets and purses, largely lost or disorganized until summoned by our accountants and tax authorities!

Shoeboxed encourages users to digitize their receipts with a scanner, before uploading the resultant image to the service. For those who don’t wish to spend their time scanning potentially hundreds of receipts, the company offers a mail-in program that is essentially a Netflix-style user experience; you mail in receipts, Shoeboxed scans and organizes; receipts are returned to you with an envelope for subsequent mail-ins.

What’s actually more useful than storing and archiving a receipt’s image, is what can be done with the related metadata. After all you could even use Flickr, Scrnshots or Skitch to privately store receipts. Shoeboxed will allow you to categorize, name, quantify and analyze your purchases. This data can be exported to other applications (Excel, Quicken) or as a report to understand your personal metrics.

The pricing plans seem reasonable, ranging from free to $60/month, though the basic package lacks the mail-in option, it’s a useful enough set of features. The high-end package is most likely quite valuable for workers generating several hundred receipts each month. In this case, the time spent on ordinarily organizing this could be converted back into billable time by outsourcing this activity to Shoeboxed.

To an extent, it’s difficult not to see Shoeboxed as a simply a great feature or product of a broader service. For example, Wesabe enables users to share and analyze their spending patterns; in this context adding Shoeboxed-like features to Wesabe would be immensely valuable. Perhaps, Shoeboxed future includes more automated and crowdsourced analysis of your spending or indeed deeper integration (and maybe acquisition?) by broader financial web services and even encouraging integration with tax authorities in various countries.

In the meantime, Shoeboxed’s basic mail-in plan appears to be a useful and valuable starting point to experiment with – though international mail-in is supported, receipts aren’t returned but destroyed by the company.

For many web workers, it could provide a simple solution to an irritating problem.

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By taking financial applications off the desktop, this next generation of services is pushing two separate innovations. It’s putting data on the Net in a way in which that information can be aggregated (think how powerful a tool like Mint’s analysis of Starbucks spending in various regions could be if a Starbucks investors could see that amount grow or decrease over time) while also allowing complete access to that data from anywhere. That’s an important benefit for those trying to stay on a budget or even for monitoring an account for fraud. As mobile browsing improves this will become even more prevalent.

Many of the sites don’t support more advanced financial transactions, such as tracking a mortgage or following investment accounts, although Geezeo and Yodlee do and several others, such as Mint, say they are adding those features in the coming months. Even more interesting are the sites such as Voyant and BoulevardR, which give users a holistic picture of their financial goals, tracking how current savings rates and spending will affect retirement or plans to buy a boat at age 50.

Into this growing hodge-podge of services (there’s a BarCamp in San Fransisco devoted solely to personal finance in March, and the inaugural Money:Tech Conference next week) comes Quicken, which launched its Quicken Online product earlier this month. So far it’s the only one I found that’s charging a subscription fee for its services ($2.99 per month), but it’s also a known brand in the space. Wesabe plans to charge subscription fees, but has yet to do so.

The subscription model is going up against what are essentially two different models built around advertising. In one, the site act as a lead generator for financial planners and products; in the other, advertisers are putting banners and other such ads directly onto the site.

While the lead generation-supported sites seem less trustworthy (is the annuity Bank A offers really the best product or did the bank just pay more than the other providers?), their creators are trying to strike a balance between getting paid and providing a useful, free service to consumers. Sites such as Mint push financial products only if they save a user money, while a site like Voyant allows a community of users to rate the benefits of a financial product being offered. Geezeo is close to this model; it offers users the opportunity to comparison shop among different financial products.

Others seem to have a murkier view of their plans for monetization. The CEO of recently funded SpendView Nikhil Roy tells me that the site will take advertising based on whether the product can help the customer save money or the planet. Others tell me they are focused on getting users rather than revenue. As the economy slows, more users may be inclined to try the sites, but if those without solid financial footing slip, it could trip up the entire sector for a long time to come.

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I particularly enjoy writing longer articles about these topics so I can examine them in greater depth and detail.  It’s a different style of writing than I do here on jkOnTheRun and I’d like to do more of those types of articles.  I have been a consultant for a very long time which has kept my writing career a part-time endeavor and I’d like to change that.  I can only imagine how sweet it would be to write full-time, that would really be fulfilling for me.  Of course doing that requires some paying writing gigs since my family insists on eating regularly.

Doesn’t this sound like something your company needs and in a hurry?  Ping me an email at jk AT jkontherun DOT com and let’s get a discussion going about it.  You need it, I can do it and all we need is a go ahead so what are you waiting for?

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Rafat Ali at paidContent has an excellent roundup of the takeaways from various stories on the news.

So now we have an example to parrot of an Internet show moving to TV — except not really, because the show’s writers’ TV backgrounds was what made the show noteworthy — and besides, they only took it online after failing to get it on TV originally. So. In my experience watching quarterlife, our reviewer Karina Longworth’s assessment rings true:

quarterlife mostly uses videoblogging as a catalyst for violating the old show-don’t-tell rule through constant, literal narration…. Ironically, with every narrative event mediated through Dylan’s diary, quarterlife often prevents the viewer from having that experience of interpreting what the characters are thinking by looking at an actor’s face.

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I was one of the many loyal enthusiasts that pre-ordered Leopard and couldn’t wait to install it on all my Macs. Unfortunately for me, it didn’t work out that way.

If you haven’t heard of the installation problems with Leopard yet, there are a few. It seems the very popular third-party application Application Enhancer does not work well (at all) with Mac OS X Leopard.

I did a quick inventory of my software, and sure enough I had APE installed (along with several APE plugins). After attempting to uninstall APE, I was almost ready to try my Leopard upgrade and noticed a blog post about Logitech Control Center mouse software issues.

Of course I have two Logitech mice, and have the Logitech Control Center installed. It appears Logitech Control Center uses APE in the background. Logitech has instructions on removing the old software and installing a new version. Unfortunately, their instructions are flawed as they reference downloading and opening a DMG file and running an uninstaller, and upon downloading the zip archive from their software download page I only found an installer application.

Their online help mentions a manual uninstall, but does not give the instructions. After several unsuccessful attempts to find the instructions via Google, I decided to take matters into my own hands. I have removed most preference panes and locations that APE or Logitech appear in my hard drive (through the shell) but am still not convinced it is completely removed. When I try to run the updated Logitech software installation, it promptly gives me an error and quits.

So, I’m left to do an Archive and Install which will likely leave me having to reinstall several applications and clean off enough hard drive space to have two concurrent System folders (at least until the installation has completed). With only 10 GB free on my 100 GB hard drive, that will be hard.

I hope to have my backup complete tonight and will remove most of the files (like my massive iTunes collection) in order to perform the upgrade.

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But those who have watched him over the years know that if Mr Chambers (aged 54) is upbeat today, it is in that gratefully relieved way of somebody in middle age who finds that he can still get his numbers up at all. Just recall Mr Chambers during the first half of his tenure, which coincided perfectly with the internet boom at its most youthfully optimistic.

Normally the venerable publication tends to be more incisive but this time around banks to much on wishy-washy analysts. For instance, it doesn’t take into account the attack of the quasi-clones from Asia. Or the fact that the network growth is coming from Asia, where price pressures are intense and could and will have detrimental impact on Cisco’s gross margins. Or the fact that its competitor, Juniper Networks is no wall flower, and despite some hiccups with the NetScreen merger has managed to take market share from Cisco.

Like most of those on the wrong side of the 50s, Cisco has gone for a nip-and-tuck. Buying Linksys was a quick way to make the revenue growth look pretty again. At the same time, it takes care of the fact that gross margins are down below the whopping 70% mark. That gross margin irked the carriers who secretly complain that Cisco is gouging cash when they are gasping for breath. Or the fact, that the security breaches in Cisco’s IOS are as routine as Yankees blowing a 3-0 lead. (Okay, I am still upset about that one!) Here, The Economist scores. Linksys is a near term fix: the company will face competitive price pressures from rivals, and will eventually become a drag. But right now it makes everything look peachy, as they say in West Virginia.

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