What do you think indicates the success of an entrepreneur? How hard you’re willing to work and how forgiving your family is? How long you can last eating nothing but instant ramen? How many people you know who wear a suit regularly?

It’s a mystical formula, and every successful entrepreneur will seem like an outlier, with some unique background or opportunity that you can’t possibly identify with. I even found myself saying the other day “Well, if I’d chosen to go to Stanford for grad school, and I were a few years older, and…”

Having said that, successful startups have certain qualities in common among their founders, and this triangle — which I stumbled across in Simon Middleton’s excellent “Build a Brand in 30 Days” book — totally resonated with what I’ve observed and learnt, so I decided to share it with you.

(Derail: The aforementioned book is terribly named. I randomly saw it in Borders, as part of my regular management/business porn browsing, and a quick flick through redeemed it. It’s not a 30-step “learn PHP in 24 hours!!” style brand intensive so much as a guide for small business owners and entrepreneurs on how to figure out what you’re all about, and how to present that to your potential customers. I haven’t got to the online section yet, so I may change my mind…)

The triangle of success

Here’s Simon’s exercise. It can work for individuals or teams.

First, write down your talents. What are you good at? What do you have a proven track record in? If a stranger read your CV, what would they think? What do your friends and business acquaintances say you absolutely rock at?

(Your friends might laud your event planning skills to the skies – you’re the one who always gets the trips and parties together without any stress or fuss. Your coworkers or boss might have no clue about that, but describe you as a deeply logical and analytical person. It’s interesting to get both sides, and I have always been surprised as to how people describe me.)

Second, write down your passions. No matter what they are, how silly or idealistic, just get them out. Are you a die-hard scrapbooker? A World of Warcraft fanatic? Are you drawn to helping others, working with children, preserving the environment? If you won the lottery, what would you do? Make a list of the hobbies, side projects, volunteer activities and events you have been involved in over the last year (or whichever time period makes sense) – do you notice a surprising theme?

Now look at both lists. Is there a magical connection? Are you by any chance a deeply skilled database engineer and also fortunate enough to have a true passion for data storage? Is your talent in visual communication and design, and you really love creating new illustrations and flowing presentations? Maybe you’re the go-to party planner among your friends, and you happen to have a deep love of the romantic, especially weddings.

If there’s no obvious connection, maybe there’s a more subtle one – you’re really good at solving hard problems and allocating resources, and you’re passionate about your business idea, so your talent will come into play while actually running the business. Or you can develop the skills and credentials needed to follow your passion, such as doing a degree or course, getting more experience, or simply giving it a go and learning. If you have a solid track record in a field but aren’t sure how to connect that to what gets you really motivated, the next point may come in handy: turn it on its head, and think about the problems and solutions that relate to both areas, and maybe you’ll discover something interesting.

The final step is: assuming you have a business (/idea), what is the evidence of a market? What problems and solutions do your potential customers face, and what supports the theory that your idea is The One? A great situation here is when you are your market, and you have a strong belief you are not an outlier; many technological projects and companies have been started simply to scratch a personal itch.

Combine these three elements and you get:

If all three are aligned, you’re in an awesome place, better off than most. But even if two are aligned and the third needs work, you’ve got a great foundation – and you know what needs fixing! You can now answer the question “Who’s the first hire” with confidence. If you’re over in one corner of the triangle, don’t give up, but use the answers above as a base for your next steps.

Which is the least important? This is totally arguable and there are counter-examples of just about any configuration.

Highly skilled people without a true passion for the idea, but with a great market demand and obvious direction to go in, can get caught up in the process of running a startup and develop a passion — often because their customers have one, and after a while, you see everything through your customers’ eyes. Whenever I see a really dull-looking startup I chastise myself for judging, and realise that to those knee-deep in that particular problem, it’s probably surprisingly interesting.

People driven by passion and a need, but without the skills needed to excel at it, can still do pretty well. You can buy in a lot of skills, finance and legal being the obvious two. The issue with this setup is getting the initial traction – why would people come to you, trust you over others, or invest in you? Assuming that everyone is good at something, you might be surprised how your apparently useless skills have a way of making themselves useful later down the line. (The number of times I end up using skills I learned from improv in the totally unrelated world of software is frightening.)

If you have passion, and skill, but no market, you could be in a sticky situation — but especially if you have passion, there are likely others that do, which means there are customers, and you just have to figure out what they would pay money for. It’s wise to use customer development strategies and rapid iteration so you can try stuff out, figure out if customers would buy it, and pivot (which is just trendy-speak for ‘change what you’re doing’) if they won’t.

So that’s the triangle of success, and a quick three-step self-evaluation process. Make it your smoke test before you dive headfirst into an idea you care little about, with no guarantee anyone else ever will, and lack the ability to execute.

In amongst all this discussion of whether the web is dead, kicked off by the eponymous Wired article, it’s hard not to feel either depressed and defensive or jubilantly optimistic — depending on which pie you have fingers in.

Apps are great. You have control, you can do a lot more with native code, you only need to worry about a single launch platform (to some greater or lesser extent), you can easily make money, you can have an offline experience.

The web is great. You have control, you can iterate, you can experiment with pricing and revenue models, you can pull in elements of other services on the fly, you can share.

The argument is often phrased as a closed vs open fight, a standards vs haphazard war. Of course if you control a walled garden you can specify exactly what playing inside it should feel like. The key element is that it’s walled; if nobody else can come and play, you hinder your own progress as well as your competitors’.

That’s why I was excited to see the Lifehacker Android Pack. Apps? Yup. Closed? Sure. But the very fact that an app broke out of the garden to become a secondary marketplace – to fix all that’s wrong with the primary marketplace – and that it’s possible to do things like recommend a ‘pack’ of apps through what is, itself, an app — that’s pretty cool.

We’ve heard before that plugging holes is not sustainable; of course not. Building on top of another service and hoping they don’t fix the problem you’re solving? Very tricky if you’re a startup looking to take millions of other people’s money. Absolutely fine if you’re an experiment that’s patching up a serious flaw until the powers that be notice you and offer to buy your duct-tape from you.

And apps like AppBrain, ironically, embody what I love about the web. Got data? Got an API? Mix it up and republish it and add your own value on top, then let the world enjoy it. Most of the recent few years’ shift in landscape and thinking wouldn’t have happened without the concept of an API suddenly becoming hot stuff, and the concept of a freely-accessible API being deeply ingrained alongside. But it makes so much sense. Why limit yourself to what your own company’s brains can think up, when people the world over are begging to do stuff with your data?

Anyway, this is why I’m excited by the Chrome web store, as it has the potential to marry up a lot of these concepts – though maybe not initially. But it’s the thought and the attitude that counts, right?

10K Apart is a nifty little contest I heard about from @limedaring (and if you haven’t seen her work or her co-founder post, I thoroughly recommend doing so). The concept’s pretty much as it says on the tin: do something nifty in under 10K. Of course, most of the highly interesting-looking apps submitted so far make liberal use of the “external API” provision; these days, you can outsource the logic, so why not?

The deadline’s on the 25th (next Wednesday) so if you have time but lack inspiration, here are ten things I would be looking at building if I weren’t so busy performing advanced CPR on FestBuzz. (Which, by the way, has up to date listings now! So it’s *half* done…)

In no particular order, and with no particular guarantee any of these are achievable within 10K (but several probably are):

Collaborative short story improv/writing

Much like those round-robin fold-over note stories you used to do as a kid (surely they had a proper name). Each successive visitor adds a sentence blindly, or with the last sentence only on view. At some predetermined N sentences, the entirety is revealed and everyone who submitted a part is notified. Probably needs some kind of web database API.

Minify/10K This

Meta-apps are fun. Could you write an app that, given another app, minifies it and tells you if it’s under 10K, with suggestions for compression? I’m sure you could.

Petrol Money Jar

For the love of god, give this a better name. This is something that could be 10K, probably won’t be, but could qualify as part of the X.com PayPal developer challenge too. Bumming lifts off friends all the time gives you a residual level of guilt. Automatically pay your mates via PayPal when they’re filling up at the petrol station; simplest version is just a pre-filled one-click “Give my driver $10″ button, but think of what you could do with geo and mobile. Track the journey, track the exact petrol station and thus the gas price, enter in the car’s make and model to get the average mpg, and get exact petrol division. Kapow.

Twitterfluff

Enter a website you like (RSS feed) or account that you follow more or less religiously. Enter a time period. Twitterfluff retweets for you every day/few hours with a randomly generated commentary comment to make it look less artificial. E.g. “RT @TechCrunch AT&T Still Not Connecting Calls http://tcrn.ch/abcDE << SO true!!”

Siteroulette

Did you ever visit that site where you typed in a Google search and got the search the person before you had typed in? Kind of like that, but with URLs instead (filtered!), or youtube videos, or…

Beautiful Reddit

Take Reddit. Make it look nice. Similarly, Hacker News (which is beautiful in its elegance, but still, this is a design contest and I’d love to see what concepts people could come up with).

Paper on a Plane

I haven’t found a good implementation of this, though I’m looking. It definitely is relevant to my interests. Anyway, a good, Instapaper-esque but-using-HTML5-LocalStorage-probably, way of saving articles to read later – so when I’m on a plane, I can catch up on the longer, meatier stuff. And, one day, videos too. (A girl can dream.)

Presentation Mode

A conference-style presentation view of tweets, and possibly other social media mentions, of a keyword (conference hashtag) – ideally with some filtering, especially for repeats. Seen this done a lot, always ugly (even the one I built). App for monitoring audience Q&A via twitter on the same hashtag would be cool, too, e.g. with Google Moderator style voting.

Super Magic Awesome Boredom Eliminator 2000

This idea comes from “Hmm, what’s a nifty web API I could use that nobody else might be tapping”. Use Directed Edge’s recommendations API and Netflix’s dataset [or anyone's, really] plus some radical 1950s soapbox style design to create an app where users type in something they enjoy, and the Super Magic Awesome Boredom Eliminator 2000 tells them what they should watch/do next. Add user suggestions for extra sparkle.

Note: I spent an entire evening hacking around with the Facebook API to see if I could work some sorcery here to do with liking and friends and recommendations and stuff, but no dice. In case you were going to try.

URL! URL! URL!

A mix of the above, and siteroulette, with your own personal sprinkling of inspiration. Kind of like Alltop but basically reduced to a big shiny red button. Pick a category (heck – you could use Alltop to seed it). Voila – a constant URLfest of cool links within that category. Whether tweetmeme, personal twitter feed, the Technorati, or Reddit’s /img section seeds it – all you have to do is press play. Possibly better as a Chrome extension; possibly already exists as a Chrome extension. Oh well.

If you do implement any of these ideas, ever, give me a shout – I’m interested to see what turns up. Good sailin’ to ye.

However, idly musing on my longer term ambitions and ideas, a thought crystallised. While thinking big is definitely the path to changing the world, thinking too big can stop you even getting off the ground in the first place. Businesses evolve and rewrite their raison d’être on a constant basis – start with something safe, something that will a) work, b) get built, c) launch, d) have customers and e) get bigger. I’ve seen startups with grandiose dreams stuck at all stages of this iterative cycle without the rocket fuel to propel themselves around again.

In other words: execute! But to execute you need to pick something executable in the first place.

On a more individual level this thinking leads me to the conclusion: there’s no shame or harm in creating a small, successful business and then doing your Big Idea. In fact, while a lot of the media successes are focused on first-time college kids, there are plenty of serial entrepreneurs who aren’t learning everything for the first time, and doing jolly well as a result.

‘Safe’ is a curse word in a world where risk is everything, and I don’t advocate starting a franchise of Subway or anything like that. Even things like starting up a coding or design consultancy, selling handmade jewellery on Etsy, or becoming a paid blogger all – to me – count as baby steps on the entrepreneurial ladder. Course, I’ve done two of the three so maybe I’m biased. (I had an eBay shop, not Etsy.) Depending on your day job, a lot of the relevant experience might already be yours – but don’t underestimate the differences between flying solo and with a harness.

If you’re burning with a big idea, the time and team are right, and you have money to play with, by all means go for the gold. If not, think of how many of today’s successes started as small, experimental, safe side projects – “let’s build a website to scratch that itch” rather than “great idea, let’s raise $5mm” – and just get out there trying stuff that can give you a winning formula to base your future efforts on, or fail quickly enough that it doesn’t matter.

I’m personally going to try out idea iteration – spending two week cycles on each idea in my ideas book, long enough to build a prototype and do some acid testing, short enough to avoid tunnel vision. The test? If after two weeks I don’t want to change tracks, I’m on to something ;)

I’m working on a wee project combining video and music of the times, and I’d love to collect memories from the time. Wow, that makes it sound like history… Anyway, we all have fond flashbacks to the age of heat reactive tie-dye shirts, and although my middle-of-the-road upbringing is chock full of happy reminiscences, I want more variety!

So, if you have a story, a memory, a moment to share from around 1992 to 2000 – for me, my high school years – and especially if it’s closely related to (or described by) a song popular in the same time period – please share it with me :) You can comment here/on Facebook, or email me (mail at jennielees dot net). Oh, and it doesn’t have to be meaningful or funny – just true.

Hmm, should I start a site to collect these or keep them private?

Here’s mine: our endless school assembly pop culture parodies. I remember dressing up as Mikey from Boyzone (I secretly wanted to be Ronan), doing a Grease ripoff for a departing Latin teacher that was, in retrospect, dangerously suggestive, and for some reason I posed as Renton from Trainspotting in front of our class blackboard in N3. God knows why. Anyway, cue montage! I wonder if kids these days do the same type of thing…

I’m fortunate enough to have lived in and around three lovely cities in my lifetime; Brighton, Edinburgh and San Francisco. Cambridge was pretty nice, too, inspiring yet overwhelming (and suffocating) in its way. Recently, my management coach (for I am growed up and have such things) advised me to travel as much as I can now — to visit the places I’ve always wanted to visit, to live in new countries, to have these sought-after experiences.

So, I shall.

Living in a different country is a fun experience, no matter how similar the country to your own. Even living in Scotland was a change from England — accents, customs, friendliness, the health service… America is a step beyond, a strange mirror country where things are sort-of-but-not-quite the same. On returning to the UK, I see it clearer than ever before. It’s not just that cars drive on the wrong side of the road, it’s the traffic customs around crossing in certain places. It’s not that the health service is totally different, it’s that doctors’ offices have credit card terminals at the front.

Stephen Fry puts it far better than I ever could, and hits the nail on the head — it’s not just that things are superficially different, but under the skin, that’s where it’s interesting.

The next adventure is to go somewhere totally different. In a way, it seems that it would be easier to learn a completely new culture than to do a botch job of assimilating one slightly but not quite the same. But we shall see. For now, I am enjoying the comfort of an old friend in Edinburgh, and secretly plotting my eventual growing of roots here.

I’m no secret admirer of O’Reilly’s fantastic technical books, so when I saw there was a new iPhone app book coming out, I got pretty excited. I’ve been meaning to dive into iPhone app development for a while now, and the advent of the magical piece of magic iPad has certainly made me more keen to do so.

Enter ‘iPhone App Development: The Missing Manual‘. (Book website)

This book by Craig Hockenberry does a really decent job of conveying the experience of being an iPhone app developer, not just the technical documentation. It contains details on Japanese tax treaties, beta testing and bug-hunting, MVC and paper prototyping. It’s more like a course on the lifecycle of an app than a detailed lesson in programming for the iPhone, something that the other iPhone books I’ve read have handled in a fairly clunky manner.

Any criticisms I have for the book’s content are not really the fault of the author, but more the ’standard’ way of teaching iPhone programming, and the constraints within which a tutor must work. Number one, I am fed up of flashlights. Seriously. I’m also pretty bored with the whole “Create an app without any code!” approach.

It seems every single newbie tutorial out there tries to schizophrenically assume you have little to no programming experience, and would rather build something with as little of that nasty code as possible, while also jumping in with details on the square brackets and types and inheritance from the get go. I don’t know. There must be a better way.

Craig’s book actually handled this better than most, and I found myself bookmarking nuggets of wisdom early on, which is useful. Let’s just say, however, I’m not following it through from start to finish. Rather, I’m using it side-by-side with the iPhone Developer’s Cookbook, which is a real joy in the ‘I just want to build cool shit’ department.

If you’re the sort of person who likes following a single tutorial through without branching off on tangents though, I think you’d be more than pleased with the Missing Manual. You’ll definitely deep-dive into some nifty Objective-C syntax and Cocoa Touch specifics, tools and tricks that are used by actual developers (no, really, I googled some of them!). You’ll learn a lot about designing, testing and releasing your app along the way, too, which is great.

I’d love to see this book done as a class, actually, it definitely reads to me that way and I think it could be nicely broken into work segments. I aim to finish it and see how long the whole thing takes, for sure. I’m learning a lot, and not just about flashlights — I just can’t help it if I get distracted every once in a while and make a twitter app or tip calculator to pass the time…

Definitely worth a buy if you’re starting out with iPhone app development and ideally have some OO experience, just don’t expect it to be your only go-to book.

Also in today’s reading, two lovely nuggets of wisdom from comments on a Fred Wilson piece on the ‘hopes and dreams’ phase (a phase that Scottish businesses either get stuck in, or never experience):

The temptation to quit will be greatest just before you are about to succeed.

If you find yourself driving off a cliff, stop driving.

Contradictory, and yet not; there’s a difference between thinking you’re driving off a cliff, and actually doing so.

I recently idly tweeted an idea which flitted through my head while considering the pros and cons of “E-School”, the Founder Institute. People asked for more, so here it is!

To build a business you need to build a product. While technical types often find the process of knocking up a quick demo webapp a walk in the park, one way a non-technical person can quickly gain feedback and respect is to build a prototype themselves.

If you have an idea for a web application – whether it’s a shopping site with a twist, an iPhone app that shows you nearby tweets, a game to teach children about finances, or a global treasure hunt – chances are you can build an early version to get the idea across quite quickly, even without much of a background in computer science.

Today’s tools are accessible and almost universal, but they can be really daunting if you don’t know where to begin. The value of creating your first prototype yourself in terms of feedback, understanding the problems you’ll have, and even the exercise of trimming down the feature set and figuring out the MVP (minimum viable product) is far, far greater than the time saved outsourcing it to the Philippines.

But where are the tools to teach you how?

There’s stuff to turn hackers into entrepreneurs, but connecting entrepreneurs with the tools hackers have at their fingertips seems much less common.

Here are some of the ideas I have around creating a resource (offline workshops? week-long intensive? online course? incubator? unconference? wiki? website/blog? book?) to help people without a technical background build a prototype of their idea quickly, and get feedback on it.

Methods

• How to design, structure and plan a web application (see below for how to build)
• Rapid prototyping, iteration, and agile development (i.e. build it quickly, get feedback, change it)
• Minimum viable product and how to figure out what should be in your prototype
• Ways to test out your application; how to find initial users and get feedback (Real stories)
• Feedback channels for prototyping before you’ve written a line of code
• How to pull off an awesome investor demo (Interviews)

Technology and Tools

• Product and feature design techniques
• How to make the most of paper prototypes
• What’s wireframing and why should I bother? Won’t the designer do that?
• Designing an awesome user experience
• Visual design basics (Analysing/Breakdown of beautifully designed prototypes)
• How to make things look good and feel polished without a degree in graphics
• Readily available tools and products you can use to speed this along

Getting Help

• Ideally, build everything yourself; it really helps your credibility and teaches you a hell of a lot along the way. If this isn’t an option for whatever reason,
• How to outsource the building of a prototype
• How to find a developer and/or designer
• Once the prototype is built and you’re happy, how to find the right rockstar lead developer to take it forward

I’d love to hear some feedback on this idea and information on areas you particularly want to learn more about (whether I included them or not) — and how you’d like to consume the information.

Cheers,
Jen

The Founder Institute’s Bay Area semester is coming up, and I initially started frothing at the mouth at the chance. After all, it’s opportunities like this which drove me to Silicon Valley in the first place… right?

Maybe not.

The Founder Institute’s programme looks fantastic. And very useful. Educational. Focusing. Intensive. An invaluable way for an entrepreneur to get a full picture of the business side of startups, the real driver behind the roadmap, etc.

It also looks extremely familiar.

In Edinburgh I have to admit I was a training junkie. I did EPIS, NESTA, the Ken Morse workshops, Ignite Cambridge, and Astia (UK and US). Plus some fantastic one-off sessions such as Bill Joos’ pitch training workshop which will undoubtedly be the reason I successfully raise capital.

But at some point, the wheels have to come off, and you gotta put all the training to work.

Reviewing the Founder Institute’s curriculum, there’s stuff in there I’ve seen time and again in the past. (Which is encouraging, rather than offputting.) There’s actually sessions missing that I think would be interesting, such as focusing on lean methods like customer development and metrics-based iteration, though a lot of it is common sense once you know the basic principles.

The main value of doing a programme like this one – especially this one, as it’s compatible with a day job – is forcing you to put aside time and focus on your startup, to make it a reality. And, primarily, the fantastic networking (and investment) opportunities. But, you know, I have those through Astia – and I haven’t used them yet, because I’m not ready to.

So, for me personally, the only real gain I might get from the Institute is a cofounder and mentor. I could definitely use a mentor, but there are ways to reach out to people that don’t involve a fee and equity, and a huge time commitment that I would rather not have right now.

So, dear Founder Institute, don’t take this the wrong way. It’s not you, it’s me. Maybe we can catch up in a year or so? Great. I’ll call you.

(Aside: If you’re not me, especially if you have a solid idea and little real exposure to the business side of things, you really should do the Founder Institute or something similar. It looks to be very useful, for the right person. And if you think I’m deranged and should change my mind, feel free to comment.)