Startup 1: a product for online shopping sites to use to help customers make complex purchasing decisions. It was difficult to use (required user take a questionnaire) and was one more cost for ecommerce sites to consider. I was there only for a short, 70-hour-a-week stint as a contractor. The company and people seemed nice enough, but I've never seen a market for what they made.

Startup 2: Took a job as a manager of "professional services" (before I understood what that meant) for a business banking software startup. It had VC cash and was burning through it faster than it was getting customers. They sold, likely very cheaply, to a competitor eventually. I'd have stayed longer, but the "professional services" essentially meant travel, contrary to what I understood in the interview, so I left fairly quickly. The company just tried growing staff and office space faster than their revenues. I don't really know how or if the founders did on the sale, but it wasn't the huge success hoped for.

Startup 3: Mine! A rental listing site. Partnered with a "business" guy who couldn't really offer much. Went after a market just dripping with competitors, including rent.com, apartments.com and some guy named Craig. Faced chicken/egg problem in multiple ways. Hard to convince savvy landlords to list if no one else has. Hard to convince savvy landlords to list if no renters visit the site. Hard to convince renters to visit if no properties are on the site. Hard to convince search engines to rank me for much if no listings on my new site.

#3 wasn't all bad. I did get people to list and get organic traffic, but just not enough to sustain the project. I worked the longest and learned the most from the rental site. As a professional, coding a web app from CSS to the database, managing customers and system administration stretched me and helped me like nothing I'd done before.

And that's why I'm looking to make my future #4 a success. :-)

Basically the guy was making $200K a month from a myspace layout site(was the top result on Google), felt like he was on top of the world(bought a few BMWs cash), then he decided to improve the user experience and completely redesigned the site.

Well he forgot to do an htaccess redirect, and overnight he lost almost all of his traffic, since Google kicked him down to page 8, since w/o htaccess they felt he was a brand new site.

Then he spent $30K buying SEO, and only got up to page 5.

Then he tried to get some help by partnering up with some guy from Australia, and the guy stole his site(had access to the server), and released it as a $20 script template, so overnight there were hundreds of clones.

So within a few months, he went down from making $200K a month to $5K a month.

Seriously once Andrew throws up the site on mixergy, you have to go watch it.

He was using php before, and his entire structure was the usual ?p=123

along with what matt said, does this mean they put it on a new domain? why would they do that?

So basically as far as Google was concerned, the only page that was still working from the old site was the index page, and even that was completely different.

There's a lot to learn from these stories, as you can see from vaksel's comment here.

Startup 1: Lucision - process-flow based document organization for law firms. http://www.memestreams.net/users/jello/blogid315504 Saved money and moved to India to build a prototype. Lawyer friend bailed.

End State: The Beach. The Himalayas. The Dalai Lama's birthday party.

Startup 2: Upon return to states, kept the company name, changed the tune - http://www.lucision.com Web-based appliance for slot machine analytics. Focused on tribal market. Raised seed money, lots of industry press, beta install at one casino, integrated with leading casino management system. Slugged it out for two years as salesman and developer, and doomed self to failure with a front-heavy pricing model (coulda signed up many casinos for a monthly fee), bizarre denial about the reality of a two year sales cycle, gross underestimation of competition, FOSS stack in an MS centric market, being a lone founder after the first three months, selling to the gaming market from Atlanta (why!?) when I should have been in Vegas, too much time spent very ineffectively trying to raise money, and figuring out what the hell I was doing. Should have failed way, way sooner.

End State: "Hey, with my experience I can now get good jobs!"

Startup 3: http://www.starcaller.com Star Caller - went to beach to relax after a couple years of intense international consulting, surfing buddy is a film hustler... a startup happened. Didn't go full time on it, learned a lot about producing multimedia and the film industry. Think we coulda made this work if we were in LA - we had leads, just not a thick pipeline. Still get calls from studios to pitch them campaigns - decline. Was always a sideline.

End State: "Hey, cool - I know about (prematurely) scaling things using AWS!"

Startup 4: Cloud Stenography http://www.cloudstenography.com - prototyped a web-based Apache Pig GUI. Early abort - after some good interest, decided I had insufficient personal savings to even think about pursuing a company.

End State: "Hey, I know Hadoop - I can get a job in Silicon Valley in big data!" Moved to Silicon Valley.

I've lost a lot of money tanking startups, but its worked out reasonably well career wise. I can't sit in a classroom for more than 15 minutes without going nuts, so I figure I got my street MBA and some technical skills. Did a lot of consulting in between. Can't say I regret anything other than not moving to Silicon Valley sooner.

My next company will be with talented people from my network, in silicon valley, solving a data problem that cures someone's pain.

Are you talking about yourself there ? It almost looks like a third-person narrative.