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My history of (mostly failed) side projects and startups (gabrielweinberg.com)
316 points by taylorwc 2201 days ago | hide | past | web | 81 comments | favorite

As a builder of digital things, the 3 things I have the most trouble communicating to non-builders are:

- how hard it is

- how much time it takes

- how long it takes to become successful

So instead of trying to explain it, I may just send them to this blog post, which shows all 3. Thank you, Gabriel!

(Now if only you would remove that Mojo Badge business from blocking your great content.)

Thx--I may do that (remove it). I was alpha testing it for a friend.

Update: removed.

While those three things are certainly true and Gabriel's post does a great job of showing them, don't forget: anyone can do it.

Among my non-startup friends, there seems to be this pre-conception that people are working in some day-job and one day, have some crazy idea that nobody else has thought of and go and start a company and become successful.

Good to see several people writing recently (from experience) about how this couldn't be farther from the truth. While it may happen from time to time, it's clear that most founders of successful (technology) startups have built a long-term lifestyle around working really hard, for a really long time, on a bunch of their own ideas and projects. Especially true given what we know about how much of a role luck and timing plays in the success of startups.

Thanks for the post, Gabriel.

"Ship often. Ship lousy stuff, but ship. Ship constantly." - Godin from http://the99percent.com/tips/6249/seth-godin-the-truth-about...

An overnight success, 15 years in the making. The lesson here is that you only really need to be successful once, so keep trying.

Yup. One of Mark Cuban's finest lessons: http://blogmaverick.com/2005/05/30/success-and-motivation-yo...

Why did Google blacklist all of your Tldscan sites? Was it just because your sites' content was updated automatically? Or was it because you did something wrong for SEO?

Here's my (completely unsubstantiated) theory. It happend literally the day after crossing $500 & 50K views in adsense. I'm guessing one of those was a trigger for manual review by some contractor, perhaps overseas. They looked at my sites for 3 sec, found them to be cookie-cutter and decided to blacklist the account. I get the impression they shoot first, ask questions later. I didn't feel like dealing with it all or starting over so I just moved on to other things.

I talked to someone from Google at I/O who should know and he claimed they don't play "Whack a mole" with websites. They will tweak their ranking algorithm to punish the behavior they see in a web site they don't want to be ranked.

That was probably me. We have two sides to the webspam team at Google: engineering and manual. We definitely prefer to write algorithms so that we avoid dealing with individual websites--the idea is that you strive to fix the root cause of an issue, not to tackle specific sites. However, if we see a website that violates our guidelines and that gets past the algorithms, we are willing to take manual action. Where possible, we use the output of the manual team not only to reduce spam itself, but to train the next iteration of algorithms.

For example, one of the big issues in blackhat spam this past year was illegally hacked sites. Our algorithms weren't doing the best job on hacked sites, so the manual team kept an eye out for hacked sites to remove them (and often to alert the website owners that they'd been hacked). The data generated by the manual team helped us build and deploy multiple new algorithms to detect hacked sites, leading to a 90% reduction in the number of hacked sites showing up in Google's search results in the past few months. That decrease in hacked spam in turn frees up the manual team to tackle the next bleeding-edge technique the spammers use.

I suspect every major search engine uses similar approaches: try to stop the majority of spam with algorithms, but be willing to take action in the mean time while engineers work to improve the algorithms.

Great to know. Out of curiosity, in this particular case, did you save supposed violations for each site, or did you blacklist all of them based on a few?

It varies for different cases depending on a lot of factors like severity, impact on users, etc. In the particular case from above, to find out the history of what might have happened, I just picked a domain at random and dug into its history to find the autogenerated pages with tons of typos for each domain.

I kinda thought one example would make the point. Does it help that much more to give another example? I can look more up. For http://www.bigbadblogdirectory.com/ it looks like you were autogenerating typos not just for websites, but for popular blogs. So http://www.bigbadblogdirectory.com/jeffmatthewsisnotmakingth... looks like it had

(I had to cut out the vast majority of the typos because the comment was too long for HN.)

jeffmatthewsisnotmakingthisup.blogspoot.com, jeffmatthewsisnotmakingthisup.bloyspot.com, jegfmatthewsisnotmakingthisup.blogspot.com, jeffmatthewsisnomakingthisup.blogspot.com, jeffmatthwesisnotmakingthisup.blogspot.com, jeffmatthewsisnotmakingthisup.nlogspot.com, jeffmatthewsisnotmakingthisup.blogspot.ccom, jeffmatthewsisnotmakingthisup.bligspot.com, jeffmatthewsisnotakingthisup.blogspot.com, jeffmatthewsisnotmakinghtisup.blogspot.com, jeffmatthewsisnotmacingthisup.blogspot.com, jdffmatthewsisnotmakingthisup.blogspot.com, jeffmatthewsisnot akingthisup.blogspot.com, ieffmatthewsisnotmakingthisup.blogspot.com, jeffmatthewsisnotmakingthisup/blogspot.com, jeffmatthewsisnotmajingthisup.blogspot.com, jeffmatthewsisnotmakingthishp.blogspot.com, jeff atthewsisnotmakingthisup.blogspot.com, jeffmatthewsisnotmakingthisup.blogspot/com, jeffmatthewwisnotmakingthisup.blogspot.com."

I could post more examples from the other domains, but my point is that this is the sort of thing that users dislike and complain about. If you were a blogger and saw pages like this ranking for your name or your site's name, you probably wouldn't be happy either. From looking at a few domains, I don't think that we overgeneralized from a few pages in this case.

I know that you've moved on and the domains are shut down now. And I'm not trying to be cantankerous. I'm just trying to say that from our point of view there's good reasons to take action on sites like this so that users don't complain to us.

So, basically what you're saying is I went wrong with the typos? I got really excited by my algo and was overzealous with adding it. I believe I did take it off of the sites I issued re-inclusion requests for, but they never got re-included and I never got any messages back (to my knowledge). Also, they were not on every one of those domains.

Each site took a long time to make actually. They either involved generating a data set from scratch or piecing together and parsing other large data sets. This one in particular, I was crawling the Web for feed discovery and was planning on adding stuff like grouping the best posts by category, etc.

Yeah, would love to know about some others, e.g. japanese2englishdictionary.com, idnscan.com, serverslist.com. Also, did you actually get any complaints about this or was it triggered by some other threshold/thing? On a side note, I still get requests about exposing some of this data, i.e. sites behind ip addresses or lists of domains matching some criteria. In any case, thx for the info!

I can understand the need to take action. I just think it could have been handled better. If typos were the problem, I would have removed them immediately if someone told me, and that could have been automated. In retrospect, it seems pretty obvious, but it wasn't at the time.

The typos were definitely going overboard. I can understand the appeal of "I've got this great tool--what can I do with it?" But we get a lot of complaints about typo spam, so that's a sensitive issue. I definitely would have done less of that.

There's also a class of folks we call navigation spammers who try to show up for tons of domain name queries. I can give you some history to provide context. In the old days, when you searched for [myspace.com] we'd show a single result as if someone had done the query [info:myspace.com]. The problem is that people would misspell it and do the query [mypsace.com], and then we'd end up either show no result or (usually) a low-quality typo-squatting url. So we made url queries be a string search, so [myspace.com] would return 10 results. That way if someone misspelled the query, they might get the exact-match bad url at #1, but they'd probably get the right answer somewhere else in the top 10. Overall, the change was a big win, because 10% of our queries are misspelled. But if you're showing 10 results for url queries, now there's an opportunity for spammers to SEO for url queries and get dregs of traffic from the #2 to #10 positions. Now we're getting closer to present-day, so I'll just say we've made algorithmic changes to reduce the impact of that.

But you were hitting a bunch of different factors: tons of typos, specifically for misspelled url queries, autogenerated content, lots of different domain names that looked to have a fair amount of overlap (expireddomainscan.com, registereddomainscan.com, refundeddomainscan.com, etc.). If you were doing this again, I'd recommend fewer domain names and putting more UI/value-add work on the individual domains.

Matt Cutts often tells us this - but he talks specifically from a search web spam perspective, I suspect the Adsense team have different rules and probably can (and do) "play Whack a mole" when appropriate.

Interesting, but in this case it wasn't that it was ranked lower, but that one day I had 25 domains indexed fine and the next day they were no where to be found, i.e. not in the index at all. And I had plenty of other domains (not in that adsense account) that were still ranked fine.

Lies, damned lies.

I don't think that was the issue. The fact is that if you've got dozens of websites, each of which has lists of domains/IPs like http://www.mattcutts.com/images/verypopularwebsites-com.png , that is the sort of thing that users complain about and don't want showing up when they do a search. Especially if sites have autogenerated boilerplate content for each one of those links.

I mean, if you're auto-generating a page that has this text: "Elcorillord.com

Common misspellings and typos: Elcroillord.com, Elcorilolrd.com, Elcori.lord.com, Elcofillord.com, www.elcorillord.com, lEcorillord.com, Elcotillord.com, Elcorillor.com, Elcoeillord.com, Elcori,lord.com, Wlcorillord.com, Elcorjllord.com, Elcorillord.coom, Elocrillord.com, Elcor8llord.com, Elvorillord.com, Elcorillprd.com, Elcorillord.cim, Elcorillorf.com, Elcorilloed.com, Elorillord.com, Elckrillord.com, Elcoriplord.com, Elcorillord.ckm, Elcorillord.cm, Elcorillord.ccom, Epcorillord.com, Elcoril;ord.com, Elcoirllord.com, Elcoriillord.com, Elforillord.com, 3lcorillord.com, Elcorollord.com, Elcorillordd.com, Elcorill0rd.com, Elcorillord/com, Elcoriolord.com, Ekcorillord.com, Elcorillord.xom, Elcorillord.co, Elcorilord.com, Elcoillord.com, 4lcorillord.com, Elcoriloord.com, Elcorillorr.com, Eldorillord.com, Elcorillord..com, Elcorrillord.com, http://www.elcorillord.com, El orillord.com, E.corillord.com, Elcorillord. om, Elcorilllrd.com, Elcorillrod.com, Elcoriklord.com, Elcorillorrd.com, Elcorillordcom, Elcorillkrd.com, Elcorillord.om, Elcorlilord.com, Elco4illord.com, Elcorillrd.com, Elcprillord.com, Elcodillord.com, Elcorillordc.om, Ecorillord.com, Elcoorillord.com, Slcorillord.com, Elcorillorx.com, Elcorill9rd.com, Elcorilpord.com, Elcorillord.cpm, Elcorillord.fom, Elco5illord.com, Elc9rillord.com, Elcorillird.com, Elcirillord.com, Elcorillord.clm, Elcorillors.com, Elcorillord.vom, Elcorullord.com, Elcorillord.comm, Elcorillord.c9m, Eocorillord.com, Elcorilloord.com, Elcourillourd.com, E,corillord.com, Elcorkllord.com, Elcorillodr.com, Elcorillodd.com, Elcorillord,com, Elcorillotd.com, Elcorillod.com, Elcorillor.dcom, Elcor9llord.com, Elc0rillord.com, Elcoril,ord.com, Elcorilllord.com, Elcorillo5d.com, EElcorillord.com, Elxorillord.com, E;corillord.com, Elcori;lord.com, Elcorllord.com, Elccorillord.com, Elcrillord.com, Elcoril.ord.com, Elcorilkord.com, Elcorillord.cmo, Ellcorillord.com, Eclorillord.com, Elcorillo4d.com, Rlcorillord.com, wwwelcorillord.com, Elclrillord.com, ElcorillordLcom, Dlcorillord.com, Elcorillofd.com, Elcorillore.com, Elcorillord;com, lcorillord.com, Elcorillorc.com, Elcorillord.c0m, Elcorillord.dom, Elcorillord.ocm."

Surely you have to see where many people would consider that either keyword stuffing, gibberish or typo spam.

Thanks Matt. I was building a business off of these domains and realized that Google rankings were the biggest wildcard, and really didn't want any trouble. So I read the Webmaster guidelines closely and often and didn't think I was violating them.

However, I realize some were closer to the line and I should have focused on being less cookie-cutter and more useful in the domains that were really better (more farther along). I had always intended on coming back and working more on each, but wanted to get placeholders up quickly because it takes a while to get backlinks and indexed.

I guess I'm saying I had hoped I would have at least been contacted with a warning and what was found objectionable before just being totally blacklisted with no reason given. I would have also hoped that each site would have been addressed individually. If I had been contacted and you had said, hey, you need to remove these misspellings off of these sites, I would have done it immediately.

Here are some comments on the above though. Again, from my perspective these weren't violating the guidelines because the pages were useful from the user's perspective and there were no hidden tricks going on.

First off, there were actually many categories of sites, domains was just one of them. Others were sports stats, definitions, language, medical, and addresses. For each site I made, I was modelling it off of other sites that had gotten great Google rankings for years. I had hoped to eventually improve the UX on those sites and get similar rankings. For domains, I'm talking mainly about who.is and domaintools.com.

Each domain had a static site index, and that's what you linked to above in the screen shot. The extensive ones weren't really meant to be browsed, but just so search engines could find the pages (pre my knowledge of sitemaps). It's no different than any of the other static sitemaps, e.g. http://who.is/whois_index/index.php, and most of them looked better than the screenshot.

That one in particular came from the code for the streetsandzips site that was a big tag cloud. I was trying to find ways to make the static site better, and that was one of them. It looks better when the fonts are of different sizes :). I had intended for that site to make them different sizes based on the traffic numbers, so Google, Facebook, would be really big, etc. On the streetsandzips site the bigger cities are bigger.

In fact, I believe I evolved the sites so that those (site index) pages had noindex,follow on them such that they wouldn't come up on search results. I also added a search engine (Google custom search) on each page as well. I don't remember if I got to the tag cloud sizes for this particular domain at the time of blacklisting.

As for the misspellings, I did mess around with those, but not on all sites, and I believe at the time they were blacklisted that had been removed from most of the domains, if not all.

Common misspelling and typos as you know is a tool that people provide to those who buy domains. I built it for that purpose, and wanted to see how many people were actually searching for this stuff, so added it to some of the domains. Turns out, a lot of people do. I didn't just tack it on to the footer or cloak it or whatever; I put it in with a purpose that people ask for, e.g. common misspellings and typos.

Additionally from the users perspective, if they got to this page by typing in one of those misspellings, they were getting a big link to the official site at top and then more information about that site, e.g. siteadvisor rating, traffic, etc. So it was essentially functioning as one-click Did you mean x.

I'm happy to answer more questions about it. But it is pretty clear that it was still shoot first and ask questions later. No one ever contacted me about anything. I wasn't trying to hide anything from Google. It was all in my personal adsense account.

I can understand from a search engine perspective, banning sites. But given I already had a relationship with Google, I expected to be contacted. In fact, at one point I had a call with an Adsense guy from Google trying to help me better optimize my sites for Google! He looked at them and had no issues with them, so I thought I was fine.

Also, IIRC I submitted at least one re-inclusion request after being banned, and never heard a response back from that either. Before submitting that request I did a top to bottom review and tried to remove anything even close to the line, including misspellings I believe.

From what I've seen Google doesn't contact people :) My guess is they also have a policy of not sharing reasons for getting blacklisted, to ensure they're not giving spammers an easy way to fix their website.

They claim they respond to all "Site reconsideration" requests. I had to file one once, they did respond, but with a very non-informative and unhelpful response.

Yeah, in retrospect I should have taken it slower and not gotten as close to the line in the first place. It's totally my fault, and I'm not bitter. As you can tell from the OP, I've had a lot of failure, and I similarly learned from this one.

The tricky part is that the math works out something along the lines of there being ~200,000,000 domains and there being ~20,000 Google employees. At a simplistic level that works out to 10,000 domains per Google employee. Which means that even if Google stopped doing everything else and everyone at Google spent all their time talking to webmasters, they'd each have to answer 10,000 peoples' questions about rankings, how to make their site, whether they have ranking issues, etc. That's oversimplifying somewhat because there's lots of parked domains, but not too much--you'd be surprised how many people want to talk about their parked domains and why they aren't ranked the way they want. My team is vastly smaller than the number of Google employees, of course. And our first order of business has to be worrying about what users see when they search; talking to webmasters is the secondary priority.

The net effect is that we haven't found a way to talk 1:1 with every webmaster, and I'm not sure whether that's possible. The story of webmaster communication for the last few years at Google has been trying to improve scalability of the info. The earliest Google webmaster communicator ("GoogleGuy") answered questions on a webmaster forum. In 2005 I started a blog, which has the advantage of permalinks for posts like http://www.mattcutts.com/blog/seo-mistakes-autogenerated-doo... . We tried doing live webmaster chats, but that would only reach 400-500 webmasters at a time.

The most scalable thing I've found so far is making videos. Here's a video that came out last month about the dangers of autogenerating pages for example: http://www.youtube.com/watch?v=A8bgpWtVHo4 . We're at almost 300 videos now, and we're getting closer to 3M total views on our webmaster video channel. The hope is that this additional guidance helps people self-identify what can cause issues to avoid or to correct them without needing to talk to Google.

The other big tool that has been helpful is http://google.com/webmasters/ . That provides tools to identify the common errors/mistakes that webmasters make (crawl errors, 404 pages, canonicalization, robots.txt issues, identifying hacked sites using the "Fetch as Googlebot" feature, etc.). That helps with many of the straightforward issues, but of course it doesn't solve the issue with "sheer number of webmasters who have ranking questions vs. number of Googlers." If anyone has suggestions on how to tackle communication with webmasters in a more scalable way, I'd appreciate feedback on how to do better on that.

I think the best scalable thing that you could do would be to generate a lot more useful automated warnings via all registered channels. And then have a process you outline somewhere on timelines and how to correct. I think the biggest hassle from the user perspective is it all feels like a black hole and black box.

I understand the argument behind keeping it a black box, but it doesn't need to be as much of a blackhole. For example, in this case the following could have happened:

1) Site triggers some alarm for violating something.

2) Just those site(s) get strongly penalized.

3) Automatic emails go out in the message centers of Google Webmaster tools, analytics, adsense, and Gmail -- wherever the sites show up registered. In my case, it would have been all of the above.

4) The messages indicate the nature of the violation, that there is a penalty in effect.

5) There is a link to click on if you think you've corrected the errors.

6) If you click it, it auto-checks your site in y days and sends you another message that it passed or not.

7) If not corrected, it stays penalized or there are a series of penalties until full blacklisting.

That's all automated, i.e. scalable. I understand there are some tricky bits about how much to reveal about why things were penalized and what not, but I think those could be worked around usefully.

Matt wrote a blog post about this http://www.mattcutts.com/blog/notifying-webmasters-of-penalt... and published a YouTube video http://www.youtube.com/watch?v=hTI1TSmKmps

Google attempts to determine whether you deserve a warning; the goal is to notify honest folks, without notifying real "bad guy" spammers that they've been caught. Naturally, the algorithm gets it wrong sometimes... detecting wrongdoing is easier than detecting intent.

Were you blacklisted from Google Search or Google AdSense or both? Google AdSense's blacklist policy is totally separate from Google Search; Google AdSense's policy is to blacklist people on suspicion of wrong-doing (guilty unless proven innocent).

I'm not about the "unless proven innocent" part in Adsense. It seems to me that when they think you're guily, that's it.

Thx--just Google search actually.

First, Matt Cutts is awesome. I don't think this can be disputed.

Second, we're doing our part to spread what we're learning about running a top 500 website (Stack Overflow) with the community, in the form of http://webmasters.stackexchange.com

Do we make mistakes? You bet we do. Just the other day I accidentally disallowed all questions on Stack Overflow from being spidered in robots.txt. That.. was .. not a good day.

The videos are great. Also, webmaster central has a ton of great info.

However, I interact with a lot of customers who seem put off by webmaster central. It seems to be a very outdated interface. I understand it's important to be clear and concise when explaining these issues. But if you look around the web 2.0 world at people providing similar information there's a harsh contrast.

Put simply, webmaster central is small text with a dark appearance and little or no graphics. In my experience and testing this harbors a mentality of "This is too complex". Users seem to encounter long wordy pages with no graphics and convinced themselves it's beyond them, before they begin to read.

Making a page lighter and throwing in a few visual aids goes a long way in curbing this issue, as well as making the information easier to understand and more fun to read.

It seems like a small thing, but it scales to become overwhelming when you consider that most people who encounter a page like this and dismiss it at a glance start looking for an email us link or a contact phone number.

This is my experience anyway. Perhaps your results may vary.

Morr, thanks for the feedback--I'm talking to that team in 45 minutes, and I'll pass on the advice. The webmaster console has evolved a lot through the years, but I'd be the first to admit that it's a lot of info on a relatively small amount of pages. Lately the philosophy has moved more toward "Let's try to set up the tools to solve the most common questions or problems that come up." That could work better than a passive panel of information that doesn't tell you what to do about all the info you see.

The idea is still percolating, but I think it's got a lot of potential.

In my case some clicks worth over $2 (if I remember correctly) triggered manual review. They sent me canned email about tos etc.

The funny part is that the domain in question was already expired when email arrived because I've decided to stop this venture.

I wonder how many otherwise viable little businesses fall victim to this heavy handed approach.

Is this one of the reasons DDG got started?

Well, it did push me onto other things, though I wasn't (at least consciously) looking to get back at Google.

Maybe this can help . . .

I have a few websites that automatically make new posts. As of 10/14, they all show 0 pages indexed in Google. Previously they would get a few thousand visitors per day.

I guess Google feels as though they violate their terms and removed them. It seems to me it was a manual removal.

I received no emails in webmaster tools about the removal.

"I have a few websites that automatically make new posts."

Making a bunch of autogenerated sites has its risks. For example, if you were just taking a bunch of MP3 names or Hot Trends queries and then scraping twitter for mentions of those phrases and slapping that all up on a website with scripts, that tends to cruft up our index with autogenerated content that users complain about and that violates our quality guidelines. Likewise, if all you were doing was scraping Twitter for phrases like sad or heartbroken or heartless and throwing that scraped Twitter content up on a webpage with a script, users would also complain about that autogenerated content and it would violate our guidelines. Would that be helpful insight?

As a concrete case to discuss, what about something like http://poeet.com/

I made this over a weekend. And the people whose poetry is being captured love it. But it is auto-generated in the sense you're talking about.

It actually went down for a bit and I got a bunch of complaints, enough that I got it back up relatively quickly.

Theres a clear difference between your site http://poeet.com and a clean cut case of auto generated spam. Your site is actually quite creative where it is aggregating content from a twitter hashtag and indexing short poems that may otherwise go unnoticed, you are also showing the users original tweet and @user and not manipulating anything. The original poster was likely scraping content, not providing citation and for the means of having the duplicate content wrapped around ads.

Matt - I agree autogenerated content is a problem and is polluting the search results so I'm glad you guys have taken action. But what about sites like bibleknowledgebookstore.com and articlesubmissionreview.com that are buying links, creating fake content, and spamming web 2.0 profile pages and forums? How come tactics like these are not only working, but dominating competitive markets? What's the point in going after high quality editorial links when sites are rewarded for essentially spamming?

Don't forget Google needs content publishers for Adsense. Surely that is the only reason brain liquifying content mills like ehow don't get the slap down? This junk is ridiculous (and this was one of the first pages I looked at):


How to Plan a Happy Blended Family How to Harmony in Your New Blended Family How to have harmony in your new Blended Family How to Achieve Harmony in a Blended Family How to Nurture A Blended Family How to Successfully Manage a Blended Family

WTF is this junk? Why does ehow.com get 3 million Google visitors a day? The mind boggles!

Great question, though ehow is created by user submission and paid article writers not an individual scraping other users content, publishing it, and not linking back IE $100 plagiarism. I do agree though that eHow is PURE junk and nothing but a site to generate ad revenue. I am not sure if they offer users who submit articles any profit sharing but they are being jipped as well. eHow is by the people behind Enom and a few other networks who give Google a ton of dough for advertising.

Matt, you completely rock. Those are fine examples. :)

xpose2000, happy to help without getting uncomfortably specific. ;)

Yep, pretty interesting. And although at first I didn't, I have to agree that a list of failed projects is not a bad indicator for success. At least it shows that you keep trying.

As for mine:

1. Mefeedia.com Built it out for 2 years, then sold it because it wasn't going where I wanted it to go.

2. Poorbuthappy.com Lots of traffic for travel forums, but the community got out of hand so I had to close it.

Those where the 2 main projects where there was an expectation of it possibly becoming something big-ish.

Wow, great list! My biggest take away was all of the times he says "perhaps I should have stuck with it". You never know where a project can go unless you stick with it.

Back to hacking at my project...

Absolutely. That is one of my biggest lessons learned.

This is very interesting. I think that the more failure you had in the past, the more likely you will have success in the future. I also had some previous side-projects experiences which did not work but I learnt so many things from these projects!


Why did this fail, really? This should be a runaway success. There are millions of people out there that can barely figure out their cameras, let alone understand the concept behind facebook or picasa or flickr or whatever could be considered "competition".

Even with a founder departure, this is a valid idea... why didn't you continue to peruse it?

Yeah, I do think the idea is good, but I didn't want to do the sales work my parter was doing and I'm not nearly as passionate about it as DDG.

This is another important lesson for entrepreneurs and hackers to learn. Sometimes, you have to cut loose even good ideas, in the service of the best of your ideas or the one you feel most passionately about.

You'll have dozens, or hundreds, of ideas during your entrepreneurial development...but, any one of them will probably require absolute focus and dedication to make it really work.

I wonder how many were done while holding down a regular job? From his linked in profile, it looks like he's being doing startups for a while.

Pretty cool.

Been doing startups right out of college. Only had a "regular job" for one year, Aug 2001-Aug 2002. From 2001-2005 I also did consulting to pay the bills, but would try hard to keep it to 4hr a day max. From 2005-2006 I was also in a graduate program, which I treated as secondary to my startup (but still did it)--sort of equivalent to the consulting.

Awesome. I've been trying to figure out exactly how I'm going to feel when trying to work on startup. Your post seems more realistic and kind of shows me exactly what I should be expecting.

Thanks for this.

One quick question: I'm not a uber geek. Ie I like the business side of the equation too. Is this a good thing or a bad thing ?

Not a Bad Thing, per se. I will tell you this: I recently launched a company with my cofounder who has had prior success. She had to do both the technical and business aspects. The startup we are building ATM wouldn't be a success if it hadn't been for her business experience - but I will also echo my side: she didn't do any of the programming; it is clear my skill and knowledge are deeper. So, in short, this startup really wouldn't be much without either. However, it's easier to be technical and acquire the business knowledge than the other way around, IMHO.

So, the better question is: what kind of startup are you building? If it's a technology startup, you will either need to commit to learning your technology space or finding a technical co-founder. Committing to learning the technology will teach you a lot about your interests, you will either love it or not - if you don't love it, you won't succeed technically (you might business wise, there are plenty of companies with shitty technology that make money).

Just some thoughts from a non-business oriented intellectual and programmer.

Would be even more interesting to know the details of why Gabriel failed to stick with some of the ideas. A Posterous-type service in 2001 sounds like it could have been a bigger success than the Names Database.

Nth clubs sounds like it could work with a bit of incentive for club pros to recommend it...

I wish I had a good reason for ditching the public inbox. I don't. The proximate cause IIRC was I moved my server and had a disk failure. But that really isn't an excuse because I'm sure I had backups.

It actually got traffic too. I don't know what to say other than that it didn't feel like a startup at the time.

nth Club isn't a bad idea -- it just requires sales work that I don't want to do. I thought my partner (who is into golf) would be doing it, but that just has turned out not to be the case.


In Googling "namesdatabase" I've come across some old claims of allegedly dubious practices of the site that occurred while you were running it. I know your reputation is stellar here and that you contribute much to the community so I was more than a bit surprised.

May I ask, have you addressed these allegations somewhere? I'd like to give you the benefit of the doubt, so I'm wondering where I can read your side of the story. Is there an HN thread or blog post you can point me towards? Many thanks.

Happy to answer questions. I think these address most things:





I think a lot of it stems from either misunderstanding, edge cases (http://www.gabrielweinberg.com/blog/2010/02/one-in-a-million...), or just a fundamental problem with the idea of referring friends.

Thanks for the links and your transparency. I will read up. Just to clarify - the reason I see this as relevant is because I'm a regular DDG user and put a lot of trust in your privacy claims (no logging of queries, etc).

Yup, I understand. If you're ever in Philadelphia, feel free to stop by and I can show you no logging in real time. As for NDB, the biggest points from my perspective are that:

--you could opt-out from emails or remove yourself from the database at any time.

--you could see a detailed explanation of how every aspect of the site worked before signing up, on a page I spent countless hours writing and tweaking.

--similarly, there was a vast support system that answered almost any faq.

--you could see the whole database on our static site before signing up.

I'm intrigued by the issues raised by selling a company which has personal data like in the case of NDB.

When you sold NDB did you have any concerns about how the new owners would treat members and their data? Knowing what has happened since (which--for some people at least--seems to be controversial) the sale would you do anything differently if you could?

A few years ago I had a company approach me to sell a small site I was running but I was never quite convinced they weren't just spammers/scammers wanting a customer list and felt like I owed my users more than that.

Definitely. The buyers were a public company who had recently bought classmates.com, were changing out the management, and had wanted to make it into a better site so-to-speak. I haven't substantiated any of the post claims, so I can't really speak to what happened. However, I would say that I think it really makes a difference if the team is going to stay or not.

Very very inspiring post. I've built and released only two web sites and just a couple of C++/C projects in storage area (of course nothing successful), so I have way to go...

It be would interesting to know what did you learn of each these projects? Which project do you consider the most important from learning perspective?

It's all very incremental. I certainly learned a bit from each, but probably learned the most from my first "real" startup, learnection. It was first major failure (really ever) and I took it pretty hard at the time.

I wonder if the lesson from this is perhaps narrow but deep rather than wide but shallow?

And just imagine there are people, most people actually, that think they have This Great Idea and don't want to tell anyone about it without an NDA because they think you will steal it.

I like hearing about these and would be interested in hearing more, but can't imagine everyone would want HN flooded with personal failure histories. Is it worth cataloguing them somewhere, with potential for HNers to comment on or takeover or try again?

Call it something like 'Start Up Down'?

What do people think? Obviously not really something that's going to become a lucrative venture but it wouldn't be tough to create either.

It would be very interesting to add information about when you were working with advisors/mentors and when you were purely working on your own.

I haven't had nearly as many at-bats as you have, but enough to know that I personally can't get very far on my own without an experienced voice guiding me past a lot of dumb ideas.

At learnection I had a board of my uncle and another VC guy, who were helpful but I didn't use them at all to the degree I should have. Other than that, no real advisors/mentors.

For Zoofoo, Email client, Yahoo store thing, Namesdatabase & Kangadoo I worked with the same partner. The "Wall" (never launched) was with a different partner. And nth Club was with another partner. The rest is/was solo.

For those who missed , Andy Brice interviewed some startup/projects founders who failed :


I'd like to see how much was made or lost on each of these, enough to do angel investing after all of that. I know the $500/day was mentioned, but just curious. Was the bulk of the money made that is now invested from these startups, or some other income?

Not counting my time here, I lost about 30K on learnection, 5-10K (not sure) on Twenty Questions, 10K on Kangadoo. Other than that, it didn't cost me anything to start the others. As for upside, made a few thousand on the ebook, 5-10K on nth Club, and not sure the total on Tldscan (the $500/day max) one. Nothing else made much besides selling NDB.

Looks like you were startupping since 2000. Except NamesDatabase there haven't been any other exits. So how did you feed yourself until then? I am guessing your later projects were taken care by that exit.

Real job for one year. Then consulting. Then exit. Also, my wife has a job.


This makes me feel better. I've built and released 4 webapps with another in dev and they all seem to be perfect failures, which I've been thinking is perhaps a sign...

How did you decide when it was time to stop and try something else?

In the past, no particular process, which was part of the problem. Now, I'd do this: http://www.gabrielweinberg.com/blog/2010/05/to-pivot-or-not-...

Are there links for the two episodes of "Twenty Questions"?

Nope--not online any more.

would be interesting to see what sort of traction you got with each service. i.e. did you quit when they only had 100 users, or was it more like 100,000

Really varied across the board, but nothing with anything close to 100K users. For the ones that didn't launch, obviously none :). I can't remember exact numbers for the old stuff, but pretty much everything got a decent amount of SEO traffic that I could play with (run tests on). Decent amount is several hundred to a few thousand uniques a day. More recent stuff more on the order of 100s of users.

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