I'm the director and lead designer of a small London based web design studio where we design and build websites for people and businesses all over the world. I specialise in user interface design with my style of design being clean, simple and modern. We also often build 'responsive' websites, the latest technique for creating mobile and tablet friendly websites. I spend most of my time in Photoshop creating my designs, or writing HTML/CSS to make my designs ready to be put on the web.
I would say start with the design. When creating the designs you should certainly have the core functionality in mind and mapped out - this will allow the designer to design all the elements you need. Handing complete designs to a developer will allow them to be more efficient in building functionality around the designs as the whole site will be clearer in their mind and overall it will shorten the length of the project.
Both could work. Ad space will only generate you money if you have a large amount of traffic visiting your site - no one will want to advertise on your site if there is only 3 people visiting each day and if its pay per click advertising from Google AdSense (for example) then you won't make money from 3 people clicking on the ads. Another thing I would say with ads is don't overdo it - especially if you're a new site. Only start to slowly implement ads once you have the users and don't do it in a way that is annoying or looks like you're spamming - you'll only start to lose your new users. An app could work, although obviously there has to be the demand for your site and people really want to view it, even on the go on their mobile device. If you're a 'free site', then charging for an app wouldn't be too sensible -- at that point you wouldn't really be a free site anymore. An app for a free site should be used to encourage users to visit your site from their phone - not as a source of revenue. Plus an app will cost you money to develop, whereas advertising on your site is completely free to setup. Both could work down the line - the ads would probably come first. But again, both rely on strong demand for your website.
In most circumstances its not my position to say anything - I'm paid by the hour or per project to carry out work as the client instructs. Whether or not the concept is successful down the line doesn't really have much to do with me, unless the client is offering a percentage share of future profits which has been offered to me a few times. On this occasion I would probably decline taking on the job if I didn't think the concept was strong. Its much easier to work as a designer and become excited by a project if its something you believe in. Of course with any project if there is anything obvious that I think can be easily changed to help improve the concept I will always give my advice. Ideally I want everything I work on to be successful, as it reflects well on myself and my work and it means I can display it proudly in my portfolio. There have been times where I've been approached to work on sites that I really don't think have been well thought through and I've kindly declined the offer to work on them - to give you a recent example the client provided a 1 page brief, their favourite font and told me they want a million users within 1 year! At that point I know it would be a difficult project and a difficult client! I've also been offered work on sites that I wouldn't necessarily want in my portfolio - adult websites, marijuana growing websites etc. If I'm going to spend my time working hard on a project, I really want it to be something I can display in my portfolio to help attract other work from reputable and professional clients.
The two most common mistakes I see with startups are not valuing how important their web presence is and not looking out for the finer details in launching a website. I may be biased, but nowadays a website really is the first port of call for nearly every potential customer - even if you're primarily an offline business. Serious amounts of money should be budgeted for a website - it should be a priority and not just another item on the startup checklist. My second point of concentrating on the finer details of a website is similar - healthy amounts of time and energy should be spent getting a website just perfect! Don't cut corners and more importantly don't let designers/developers cut corners - make sure to question anyone who tells you something isn't possible! I'm probably an extreme case doing what I do, but small things like wrongly aligned text or too much margin around a photo really make a difference. Websites should be pixel perfect! If you're a startup seeking investment or trying to impress eagle eyed potential customers then a sloppy looking website that looks like its been rushed can do you more damage than you'll ever imagine!
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Radio program/music director
Jobstr looks great! I signed up using the form and have an answered a few questions now - I can't see anything I would change. Its very easy to use and very easy to find what you are looking for, both of which are very important!
First you need users - regular users that you can get visiting on a regular basis. If you think of any big successful website, they wouldn't be worth anything without their users. Which leads to the next question - how do you get users? Well you need something appealing, something that users actually need or want - you have to offer them something to keep them coming back. Maybe a lively forum where they can discuss a topic and become part of a community, maybe a blog with regular interesting news. You have to have something interesting to offer them. Once you have these users you can look at beginning to make some money - selling advertising space, selling goods or downloads, selling subscriptions to the site, becoming an affiliate marketer and taking a cut from sales. There are various ways of making money but if you think about any of them, not one would work without regular traffic (and quite a lot of it!)
I don't think I know of any crazy popular site's whose design is 'crap', because I honestly think if a site is that badly designed it really can't be popular! There are definitely some big sites that could be better designed in order to improve the user experience - Facebook and eBay both come to mind. I can't help but feel that as they've been built more and more features have been added to them and more stuff squeezed onto the page - they feel top heavy and busy and it can take a while to find what you are looking for. Facebook in particular - they seem to focus all of their energy on the timeline and newsfeed - trying to change a privacy setting can take ages when it really shouldn't!
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