You don't get to 500 million friends without a tragicomic story
October 25, 2010 4:52 PM   Subscribe

My brother needs my help launching his website! Problem: it was designed in iWeb, he's a sensitive artist, and it just gets worse from there.

My brother went to art school for painting a billion years ago, prefers to work in secret--'no looking until it's finished' sort of thing--and is quite sensitive to criticism. A few years ago, he started talking about launching a niche social networking website: let's say it's for jock engineers. He started talking to online jocks about this, all of whom say it's a great idea, and would love to have a place to show off what they've developed.

And that's when he started designing it in iWeb. He shelved actively developing the project for a few years, during which time I transitioned from a tech journalist to a web writer-content strategist; I fell in love with IA along the way, so I know a bit, but not too much.

He spoke with a developer two years ago, who wanted $25K; he re-approached my brother this year and said that it'd be much cheaper now, since the price of software has gone down. I gently suggested he talk to other developers before deciding anything—maybe even outsourcing it, since my IT husband is from another country and knows people who'd do it for a fraction of the cost—but before we knew it, he'd given him $7000.

I finally saw the iWeb design, and it's even worse than I imagined. Apparently, he expects to launch in three months. He asked for help fixing it up and launching it, but I have no idea where to start.

He says he has no more money to hire a designer. He's working 40 hours and taking one class a week, and says he has no time to flip through Don't Make Me Think. If I say a word like wireframes, sitemaps, and personas, he either makes me sell him on these very basic ideas, or says I'm just overly complicating things.

He refuses to learn Dreamweaver because "he'd have to start over from scratch," and is considering giving the developer Photoshop files. However, he doesn't understand how the developer would be able to figure out how the pages are connected, since there aren't any hyperlinks within Photoshop documents. When I asked about his marketing plan, he said he 'probably wouldn't go the normal way of advertising, which is expensive.' He only knows about a few other social networking sites.

He wrote me a sad email last night stating that I was the closest thing he has to a collaborator, even though he is impossible to work with; he really just wants validation for his work. In any other circumstance, I'd run for the hills, but because he's my brother, I genuinely want him to succeed. I just can't imagine it happening with this. (There's also a boatload of pressure from our mother that I offer him unlimited help. Also, he lives a few blocks away, hates his day job and sees this as a way out, etc.)

How can I be of help? Or be clear that I can't offer much help because I can't say anything without either of us going crazy? Or just let go of my aesthetic and professional standards and lighten up on the whole deal? If it was your website, what would you want to know?
posted by blazingunicorn to Computers & Internet (25 answers total) 2 users marked this as a favorite
If it was my website, I would want it to be a good experience for the end user. From your description, this website sounds like a hot mess.

Honestly, it sounds like he's just going to have to fall flat on his face in order for him to learn his lesson. There's mad competition for social networking sites, and you have to present something that's damn near flawless, or else you won't get any users. If he really wants his site to have a decent shot at success, he's going to have to do some moonlighting and learn all the things he's trying to avoid. It sounds like he's not even willing to try, seeing as he "can't" read one of the most slender volumes on UX design in existence.
posted by Anima Mundi at 5:06 PM on October 25, 2010 [6 favorites]

Brother, I'm too busy right now.
posted by k8t at 5:14 PM on October 25, 2010

This really is a minefield for all sorts of reasons, but there are two principal ones.

The first (and, really, the crux of the matter): the technical side. You can't write a social networking site— or, really, any site worth its while these days in static HTML, whether it comes from the bowels of iWeb, Dreamweaver or even (god forbid) Microsoft Word's 'save as HTML' feature. Common sense dictates that at the least you throw either a passable or custom skin on Wordpress/Movable Type/whatever CMS, hack it a bit and hope for the best. Real sense says you get someone in to write you a custom CMS, start small and build on it if the site becomes popular, but as you and even your brother appears to recognise, this — done properly — tends to require a not inconsiderable sum of money.

But really, the second problem is that this is for your brother. Even if you were a bona fide expert in every programming language known to man, this would still probably be a fairly minor time sink for you (it sounds like a slightly more advanced version of what all graphic designers would recognise as Word Art syndrome), given the inexperience and unrealistic expectations your brother has. As it is, you don't appear to have those skills, so at best you would be able to undertake a pretty torturous process and come out with a hodgepodge of a site that in all likelihood wouldn't really be what his project needs.

I see two real options; either you dodge it, citing time constraints or lack of knowledge, or you sit him down and explain that you can't directly help him with his project because you don't have the development experience, and that this needs to be properly thought out and executed to have any hope of working. Trying to turn ‘the HTMLs? photoshop? PEOPLES!?’ into a fully functional website isn't entirely dissimilar to hoping a drunken sketch on the back of a cocktail napkin to magically become the ceiling of the Sistine chapel by force of will alone.
posted by jaffacakerhubarb at 5:19 PM on October 25, 2010

I would want to know that this was not feasible as specced. I would want to know this while I could still get some value out of my 7K, assuming the developer has not started yet. This project can probably be rescued with, I dunno, a Ning or buddypress or Drupal implementation or something. Who is the developer and do you know anything about their skill set?
posted by DarlingBri at 5:21 PM on October 25, 2010 [1 favorite]

Sound like another hopeless visionary looking for an easy way out. I've been there myself. Looking back I think the most integer(?) thing you can do is to be honest, try to get his head out of the clouds and his expectations in check. Unfortunately, if he's anything like me, he won't listen.

I don't want to be a pessimist, but your time may be best spent figuring out how to pick him up when he (eventually) falls.
posted by spr at 5:22 PM on October 25, 2010 [1 favorite]

A social networking site under $25K ? iWeb ? Dreamweaver ? Working with close family members ? Find an excuse so you won't have to do it. Do not compromise your relationship with your brother for a project that is doomed to fail.
posted by agregoire at 5:37 PM on October 25, 2010 [5 favorites]

I sent you a MeMail. I feel bad for your brother but mostly I feel terrible you're in this stuck in this middle.
posted by DarlingBri at 5:38 PM on October 25, 2010

I've seen this in so many realms: the deficient outsider misunderstanding what it takes to make a website, code software, start a magazine, write a book, make clothes, write a screenplay, become a model, put on a stageplay, repair a car. It's the secretive-don't-have-the-time-too-embarrassed-not-willing-to-learn part that makes this a group of related stories and the dragging people along but not letting them really help.

Get out and send him a phonograph and some Coltrane vinyl so he has something to go with the drinks and the misery when his project fails.
posted by Mo Nickels at 5:38 PM on October 25, 2010 [1 favorite]

Please try to ocnvey to him that, in web development, ideas are essentially worthless, execution is what counts.
posted by signal at 5:39 PM on October 25, 2010

Anecdote 1: Remember the Simpsons episode where they go to Itchy & Scratchy Land and the robot cat opens its cranium to show circuits and tubes and Marge says to Homer: "See all those chips and stuff? That's why your robot never worked."

Invite a third party over to assess the site. Let them be blunt and frank, and let them detail in a high level manner what is missing for it to work and what it might cost. It'll hurt, but you'll be able to say "these guys know more than me, and they're telling us we're a long way off from having something that can go live, and I don't have the means to get you there, and neither do you."

Anecdote 2: A common theme on Dragon's Den/Shark Tank is when someone says they've spent X thousand of dollars of their live savings on a project that is going nowhere and everyone tells them STOP WASTING YOUR MONEY AND YOUR TIME BEFORE IT KILLS YOU, and that's the only reason they were able to get on the show to begin with. Don't let your brother be that person.
posted by furtive at 5:54 PM on October 25, 2010 [1 favorite]

My approach in this kind of situation would be to say my piece, without holding anything back, exactly once, and then keep it at arm's length. Invite him over for coffee or something and lay out all your concerns. Make clear you are NOT his collaborator (that way lies madness).
posted by adamrice at 6:11 PM on October 25, 2010

You're a kind person for wanting to protect a dreamer like your brother but for this project to survive you'd have to take it over. I don't mean to be harsh but let's recap: your brother isn't familiar with programming, user interface, advertising, the economics of social software, and ideas like his are a dime a dozen. You could do it but it would cost hundreds of thousands of dollars.

I think that primarily you should try to minimise the harm from this endeavor and be ready to pick up the pieces. Try to recover that $7k and do what you can to ensure he doesn't waste further money on this. That means doing what you can to become trusted as part of his project, even if that means not being entirely honest for the time being. Be surprised when his project fails, and during the project suggest cheap alternatives to whatever expensive ideas he has. Perhaps a slow steady realisation is the only way he'll learn, so you could allow that by getting a techie to set up a instance (it's free software, like twitter). Alternatively you could get him to get more humble by watching episodes of the Dragons Den where clueless people get shot down (it's a tedious show but it keeps making this same point repeatedly).

He's trying to replace his current job with a better one but this won't work so talk about other ideas he has because it sounds like he needs a dream.
posted by holloway at 6:13 PM on October 25, 2010 [1 favorite]

Has someone done a feasibility study? Has the market been analyzed? Who is the project manager? Who is the solution designer? Who is doing creative? When are you bringing this to market? What's the exit strategy? Who is hosting this site? What about revenue channels?

These are just a few of the questions I'd bring to him and would want an answer to before sinking any of my time and energy into this project. I'm guessing, from your description, he doesn't (and won't) answer these.

I'd also want a prospectus.
posted by TheBones at 6:19 PM on October 25, 2010

Your best approach - and I say this as someone who's been in your shoes - is to give your brother a realistic assessment of what it will take to get this out the door. Don't address issues like his terrible front-end, or the viability of Yet Another Social Networking website. Focus on the nuts and bolts of what it will take to get it done.

Start with putting together an estimate of how much time it's going to take to get this project finished. Let's say you ballpark it at 400 person-hours of work. That's one hour a day, every day, for over a year. Or it's ten weeks at 40 hours/week. Twenty weeks (five months) working it as a part-time job, 20 hours/week.

That's skilled programmer labor, as well. You can't afford (nor can he expect you) to volunteer 20 hours/week for five months. Get a reasonable estimate on freelance programmers' rates. Build up an estimate of cost from there.

Basically, treat this as a project a valuable customer has brought to you. You don't want to say "I can't," you want to say "I can, but here is what it will cost you, and why."

Then - this is the most important part - let him make the decision.

If he wants to take out a ridiculous loan to get this done, then let him. If he wants to drop everything and dedicate the next year of his life to learning the skills it will take to do it himself, then let him. He's an adult; he gets to make his own decisions.

But my experience is that most people, when faced with the cold hard facts, sensibly back away from the project. Frame this as "putting it on the back burner" for now.
posted by ErikaB at 7:13 PM on October 25, 2010

Response by poster: Thank you for your support! He's only told me that the developer is finishing up this site, and he can't even remember what CMS it's going to be in. Everytime I ask him about the developer's skill set or anything about deliverables, he says, 'that doesn't matter right now.'

I know the site can't be written in Dreamweaver; he's just 'designing' a few static pages for the 'feel' of the site, but even with a different design it'd be fairly unusable.

TheBones: he'd say a project manager is just for 'those sites with millions of dollars.' Yes, Mo, he's totally in that realm--when this is done, he's going to finish his screenplay that he won't discuss until he's done with the first draft!
posted by blazingunicorn at 7:19 PM on October 25, 2010

It looks like the developer might use Drupal but of course that doesn't change anything.
posted by holloway at 7:34 PM on October 25, 2010

If you go to , it looks like a drupal install for sure.
posted by jenkinsEar at 7:45 PM on October 25, 2010

Like the perfect girlfriend, he's idealized all of this.
He's built this up as a way to have freedom to be RICH and you're standing in his way. Your Mom sees it as a way to get him independent (and possibly well off herself.)

Ask your brother why if his idea/web site is so important, that he won't slow down to hear your criticism. Tell him that you're scared that he'll interpret your opinons as crushing his dreams of freedom.

Be very succinct. Give him your opinion with written solutions that he can read them later on:
• He's not prepared for business. (business plan, development)
• He hasn't done any marketing studies. (It's not I'll build it and they'll come)
• Ideas grow on trees, it takes perseverance to completion. (Could anyone do this?)

Ask him, how are you (or anyone else) supposed to support him, without him being able to be rational about those three elements. Be willing to estimate how much of your time it'll take for anything he wants to frame out conceptually - along with the cost.
posted by filmgeek at 8:12 PM on October 25, 2010

Disclaimer: I know nothing.

It sounds like he wants a way for members of a hobby community to post photos of projects. The doesn't need a full-fledged social networking site, and maybe he doesn't even really have a concept of what a social networking site would require. Posting photos of projects among a smallish hobbyist community could be done with a forum, provided the forum can handle image posts, right? Could you look into something like phpBB?
posted by LobsterMitten at 8:35 PM on October 25, 2010

This isn't a technology question it's a psychology one.

I cringe very time I hear this old story. Despite how heartbraking your story is, it's an old one. Someone who feels unhappy/dissatisfied with their current life hatches a plan, but is afraid to tell anyone so they halfass it in a number of critical ways, fail, and get even more unhappy and unsatisfied with life.

They also never make movies about these stories because they never have happy endings.

First I'd try to talk him out of it. I know you've tried. Maybe scare/intimidate him out of it. Yeah it sounds mean, but it's better than him going through with his current plan. Tell him you can't waste time helping him until he writes up a proper business plan that he would feel confident giving to a bank loan officer or a venture capitalist. Keep pushing back on that every time he asks for help/advice/etc.

If he's allergic to criticism he's in trouble because there is no way on this green earth that you can launch a web site without getting some brutal criticism. So maybe point that out.

If talking him down doesn't work just try to limit the damage. It's a bit of a cliche but get him a copy of The 4-hour workweek. There are a good number of solid tips there on how to float a business idea on the cheap to see if it will fail/succeed before dropping a life savings on it.

If he's not going to spend any money on marketing (the surest sign of doom of any web site) then encourage him to start the buzz on his project. Have him start a blog where he writes about the topics that would interest his potential audience. It's a no-brainer. He can do it for free (Wordpress), is like free marketing, and will help him flush out his ideas with the eager public. What will probably happen is that the blog will get little to no notice and he can find out his idea isn't going to happen without spending any money. On the other hand if it does get traction and he does get a lot of interest then he will have taken care of his marketing and can turn his readers into clients and investors.

If he can't/won't do any of that then just talk to him about his backup plan, make sure he's prepared for failure and that he's not spending money he can't afford. You know, if it just happens that it doesn't become wildly fabulously popular. And then support him, listen to his troubles and take him out for a beer.
posted by Ookseer at 10:01 PM on October 25, 2010

> he re-approached my brother this year and said that it'd be much cheaper now, since the price of software has gone down

I just wanted to note that in my personal opinion, if he literally used those exact words, that was an outrageous lie.
posted by AmbroseChapel at 10:20 PM on October 25, 2010 [3 favorites]

Response by poster: > Your Mom sees it as a way to get him independent (and possibly well off herself.)

Hell no: she just wants him to be happy, and knows that if he doesn't do this, he'll be even more bitter. She's being realistic (albeit enabling, by cosigning the loan).

Sadly, he DOES seem to see this as a possible ticket out of his day job. He has already given this guy the money; the quote about the software was a huge red flag for me, and my brother didn't have a good response when I explained that it made no sense.

It's really hard for me to wrap my head around the idea of not doing any research whatsoever around a business idea; thinking that the coding part is the only aspect that warrants professional attention; sinking money into something with no source of revenue, no business plan, and thinking that you could make money off of it.

Thank you so much for the suggestions and feedback. I'm oscillating between writing a detailed opinion and trying to get away with "sorry I'm too busy" for as long as I can.
posted by blazingunicorn at 1:46 AM on October 26, 2010

writing a detailed opinion is only going to make things worse - the advice you give won't be taken, and everything you say will be questioned, and it will quickly become a time sink as big as if you'd take on the entire development project.

Make sure you'll be "too busy" from now on, or you'll get the blame for the eventual and unavoidable failure of the site.
posted by DreamerFi at 3:09 AM on October 26, 2010

This sounds like a disaster you should extricate yourself from as soon as possible, to me.
posted by empath at 6:07 AM on October 26, 2010

Your mom has no business pushing you into this faux-project (the part of your post that pissed me off the most.)

You have a job yourself, right? And a life of your own? You don't have time to write a "detailed opinion," and especially not for free. Don't let your unhappy vampire relatives suck the life out of you.

Go about your business. His website idea sounds like some kind of adolescent boyz klub.
posted by BostonTerrier at 6:11 AM on October 26, 2010

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