What I’ve lost by not looking for investment

Photo by Eric Gjerde

Yesterday I laid out why I'm not looking for investment. I'm comfortable in my choice, but it wasn't easy. The investment process brings a lot more than cash; here's what I'm losing by avoiding it.


Convincing someone to give you money forces you to get very specific, and flesh out your business plan. Defending it against hostile questions makes it stronger. Once you've raise money, having somebody who remembers your promises breathing down your neck keeps you focused. My biggest weakness is that I'm too prone to stay in my comfort zone, working on technical experiments and neglecting everything else you need to build a business. I try to self-police that tendency, but there's nothing like having an outsider's view to keep you on track.


I spend a lot of my week dealing with paperwork, doing website housekeeping, taxes, system administration, arranging travel and meetings, and all the other tasks that could be handled by somebody else if I had funding. I'd have to spend time managing investors instead, but at least the rest of my schedule could be devoted to customer support and product development.

Advice and Influence

Most investors want to convince you they're 'smart money', but from what I've experienced, not many actually bring much to the table beyond dollars. When they do though, it can make a massive difference. They can give advice that saves months of development time, and set up deals that bring in crucial revenue. The key is identifying the people who have the will and the ability to help like that. The only way to do this is by looking for a track record, and knowing entrepreneurs you trust that they've worked with before. A well-known brand is definitely not enough. In my experience the superstar firms are less eager to roll up their sleeves, they're less hungry, though the clout of their name as a credential can make up for a lot of that when it comes to making deals.

Why I’m not looking for investment

Photo by Matt Katzenberger

The short answer? I don't have a good enough idea.

Living in San Francisco, in the current angel investment bubble, with a (tiny-but-nice) acquisition by Apple under my belt, and big plans to change the world, I sometimes feel like a freak of nature because I'm not hunting for funding. Why did I make that decision?

I spent the first year after I left Apple aiming to build a VC-backed company. I had a plausible story, built a complete prototype, deployed pilot installations, and sat in numerous boardrooms pitching partners. The trouble was, it was a terrible idea. I was following in the footsteps of Tacit, VisiblePath and multiple other enterprise email analysis failures. I had no comprehension of the torture of the enterprise sales cycle. The idea of analyzing email fundamentally creeped people out, no matter how strongly I protected privacy. In the classical model of how the process works, I would have got all this feedback from the VCs I pitched to. Aside from being pointed towards Tacit by one partner, I learned everything by painful trial-and-error. VCs loved the idea, they were deluged with email messages and made their livings through their personal connections.

The lesson I drew from that was that I was an idiot. I should be listening to customers and discount what I heard from investors. Get customer traction, revenue, and ideally a profit, and the opportunity would sell itself to potential funders. Obviously that also cut down the range of opportunities I could chase, but what I'd discovered in my unfunded year was that it's possible to build a lot with very little cash. By building fully-functioning prototypes, I could learn what users responded to, as well as what was technically possible.

The trouble is, after a couple of years of operating like this, I'm addicted. I've had many failures, along with a few partial successes, but I'm become so much better at understanding what people need, what's possible, and executing a solution. My failures are becoming faster and far more interesting. I may be living on Ramen noodles, but it's an amazing opportunity to learn. Just the process of fund-raising itself would take a massive amount of time away from that, and then explaining every month where their money's going, why I'm fishing with strawberries, and planning for the next round would take even more. 

That's still a worthwhile use of time if the funding is going towards rocket boosters to strap onto a killer idea. I don't think it's lack of confidence that's telling me none of the approaches I'm working on has crossed the threshold where it's worth it though. There's funding available, I just don't think the strings attached make up for the help. Better to live frugally, consult when I have to, and focus on learning. The more progress I can make, the more I can learn before I need to buckle in to the rocket sled, the better. I'm looking forward to honing my ideas until I can build the real business I dream of, whether that's fully boot-strapped or with the help of investors.

Gadhafi’s Speech Transcript

Word cloud

I was surprised to find that there were no transcripts available of Gadhafi's long speech on Tuesday (February 22nd), so after looking into transcription services I decided to bite the bullet and go through the whole 70 minutes myself. It was a deeply unpleasant experience, but it seems worthwhile to capture his words in an accessible form, since the world is facing so many tough choices in how to deal with him. I don't want to say he's crazy, that seems too easy, but the benevolent mask he obviously tries for keeps slipping as he nakedly threatens his 'people'.


It's a Google document that anyone can edit, so I'm hoping people who know the area much better than me will correct the many mistakes, especially with the place and people names. I also hope it does some good.

I generated a word cloud from the speech, to help me understand what the key obsessions were. People was a key verbal tic, as were 'youth', 'revolution' and 'rats'. Benghazi is obviously preying on his mind too, and he kept coming back to security. I can't claim to make sense of his speech at all, but it feels like the only avenue to understanding what's going on in his mind.

The Portraits of Three Novels

The books I love have their own unique souls, but I struggle to communicate what they are. I can describe the plot, or talk about the themes and the language, but there's an essence that's hard to get across. I find word visualizations a fresh way of capturing that flavor, but I've never been able to get the results I can picture in my minds eye. That drove me to build Wordlings, an experimental service for creating graphical word clouds. Here's what I came up with when I applied it to some of my favorite novels.

Kidnapped, by Robert Louis Stevenson

Carefully disguised as an adventure story, this is actually a beautifully-drawn portrait of friendship. The psychology of the protagonists' relationship veers between suspicion and reliance, anger and affection, in a way it's rare to read. Here's Stevenson's dissection of the tangled reaction to a dependent friend:

The thought of a separation ran always the stronger in my mind; and the more I approved of it, the more ashamed I grew of my approval. It would be a fine, handsome, generous thing, indeed, for Alan to turn round and say to me: "Go, I am in the most danger, and my company only increases yours." But for me to turn to the friend who certainly loved me, and say to him: "You are in great danger, I am in but little; your friendship is a burden; go, take your risks and bear your hardships alone—-" no,that was impossible; and even to think of it privily to myself, made my cheeks to burn.
And yet Alan had behaved like a child, and (what is worse) a treacherous child. Wheedling my money from me while I lay half-conscious was scarce better than theft; and yet here he was trudging by my side, without a penny to his name, and by what I could see, quite blithe to sponge upon the money he had driven me to beg. True, I was ready to share it with him; but it made me rage to see him count upon my readiness.

What jumps out from the word cloud is the centrality of Alan to the book. With his accidental companion David as the narrator, you can see how the interplay between them comes out in the frequent invocation of his name. You can also see how plain Stevenson's language is; "Back", "Down", "Man", "Like". It's why the book flows so easily, despite the depth of ideas it wrestles with. That made the ship that Alan and David were thrown together on feel like the right outline for the cloud, gliding through the water apparently effortlessly, while in fact relying on an exquisitely well-organized web of rigging. 

Pride and Prejudice, by Jane Austen

I'm a late-comer to Austen, only discovering this book when I was a teenager. I would read a few pages to my girlfriend every night, and the book's world became part of our private language. I'd always liked to think I was Darcy, I can certainly match his pig-headedness, but in my darker moments I feared the unwitting ridiculousness of Collins was a better match. The older I get, the more happy I'd be to just achieve Bingley's quiet decency and contentment. There's a lot to be said for nice, but dim.

It's fitting that names dominate the cloud, since the novel is like a pool shark's trick shot, as actions and reactions cascade in an intricate yet believable way. Austen's genius is the way she sketches characters who behave like actual people, but still contrives to arrange events to produce a satisfying outcome for them all. Her dark wit and cutting sarcasm make the happy endings palatable to a cheerful pessimist like me.

The shape to choose was obvious. The 1995 BBC mini-series left Jennifer Ehle indelibly as my personal picture of Lizzy, minxing from underneath her bonnet and curls. I was so hooked, I even forced my old D&D group to watch it, and even they were sold. As one of them said afterwards, "Man, that was the Star Wars of costume dramas!".

Oliver Twist, by Charles Dickens

Despite fears that he's better-known than read, I keep coming back to Dickens. His long-winded style forces me to switch gears, and the barrage of words is like a punch in the jaw compared to Austen's sweet smile while she sticks a stiletto in your ribs. It's effective though, and like reading David Foster Wallace, once you get accept the rhythm the chaos starts to make strange sense. He's unashamedly sentimental, which I appreciate, since I enjoy those sort of illusions even if I struggle to believe them.

The book revolves around power, authority and punishment, with the final chapter taking obvious pleasure in meting out lashes and rewards, sketching the future lives of even minor characters. I wonder if part of the wild success of his books was related to the audience's hunger for this sort of settling of scores? It's the same pleasure I get reading Sherlock Holmes, the relief of believing the world can make sense and is more than just one damn thing after another.

The authority is there in the words that pop out – 'gentleman', 'boy', 'old', 'Jew', 'young', 'lady'. Roles and positions are central to the action. The silhouette seemed to capture the spirit that Dickens was fighting against, self-satisfied and in charge, though I wish I'd found one with the true beadle's hat.


I'm finding this a rewarding experiment, if only for the way it's forcing me to look at my best-loved books in a new light. I'd love to hear about any you're able to create with Wordlings, and what you learned, so do let me know.

Hello Social World

Photo by Dr Case

These days it doesn't make much sense to build a consumer site with its own private account system. If users sign in using Twitter or Facebook, you can have them easily spread the word on what they're doing in your application through tweets or wall posts. The old 'enter details'/'email confirmation'/'click link' process was a leaky funnel that lost potential users too, and was a pain to implement, since automated emails alone are an art in themselves.

I wanted to use this approach on one of my sites, but I couldn't find a good example. Especially in the Rails/Sinatra world there were plenty of building blocks available for doing the individual tasks, like authenticating through Twitter or Facebook, calling their APIs, and storing data, but nothing that showed how to use them together. So, because I needed to build it anyway and it would be a good Ruby learning exercise, I set out to create a minimal-but-complete template that handled user creation, authentication, custom data storage and external sharing. In the spirit of the classic 'Hello World' code examples, here's Hello Social World.

You can try a live demo at http://hellosocialworld.heroku.com/. It's built to do the bare minimum you need for a modern social site, letting users log in, edit some data they own on your site, and then share the results with their friends on Twitter or Facebook. The data in this case is just the user's favorite color, but imagine replacing that with whatever content they actually create on your site; blog posts, photo galleries, comments, etc. It's deliberately left with zero styling, so you can add your own view code.

I was really impressed by the elegance of Ruby and the Sinatra framework. Aside from the API keys, all the code's in a single 440 line file, and 120 of those lines are comments. This is possible because the gems handle most of the heavy lifting for me. It feels very productive to focus on my application logic instead of writing boilerplate code. There were moments of frustration when things went wrong, the black box nature of gems makes them tough to debug, but there seems to be a big enough community using them that they mostly just work.

I'll be using this template heavily myself over the next few weeks, which will hopefully give me ideas on improvements, but let me know if you have bug reports or suggestions. I'm looking forward to hearing people's thoughts on this approach to a turn-key social site too. 

Ruby on Rails first impressions

Photo by Afternoon Sunlight

Ruby on Rails has often attracted me, but I've never had a strong enough reason to dive in. This afternoon, as I unhappily contemplated writing yet another web app with Twitter authentication in PHP, I finally caved. I did think about trying Django instead, since I'm using Python heavily in the back end, but the examples I found felt a bit too bondage-and-discipline for a UI that I want to rapidly iterate on. So, five years after the rest of the world, here's what I discovered in my explorations.

Fantastic Documentation. I read through the first few chapters of the Rails Tutorial book to get a feel for how things worked. It's task-oriented, hands-on, focused on things I care about and generally nicely written. All of the code and examples Just Worked, and from the footnotes this is obviously an actively maintained and tested guide.

Arrgghh Version Changes. With my confidence boosted by working with the tutorial, I set out to integrate this open-source Twitter OAuth module. None of the directions worked, some of them didn't even make sense based on what I'd learned. What is 'script/generate'? Is that like 'rails generate'? After digging I realized it was created for Rails 2 and I was on 3. How big a change could that be? I eventually got things working, but I had to hack so many things manually, from the option loading to the database migration, it was obviously a massive shift in the way things were done. In a way it's really refreshing to find a community so willing to radically clean up things between versions, but it does orphan valuable external projects like this.

Everything's There. It is really nice to have a single, standard way to do most tasks. Since git is the recommended source tool, deploying to Heroku becomes very easy to explain. When things work, they just work. There seems to be One True Way for everything from laying out project files to which source code control system and database to use, and that feels very Apple-esque. The un-hackerish secret I learned from Mr Jobs was that denying people choices saves a lot of confusion and explaining. This is definitely very constraining at times, but when it works it gives a great user experience. I know there's nothing here that I couldn't technically be doing with PHP, but getting it all out of the box and easily google-able (because everyone's using a similar setup) makes a big difference.

I'm pretty happy with my progress today, I have a basic Twitter authentication cycle working, and I'm definitely discovering parts of Ruby that make me smile. I don't know if RoR will become my framework of choice going forward, but it definitely seems a strong fit for a lot of my tasks.

Have you seen this bike?


Some of my friends have had their bike stolen, by thieves who broke through two locked doors and cut through a chain to get to it. The bike is pretty unique, an A2B electric 'Metro' model which I very rarely see around the city, so if you're near San Francisco and spot one of these in unusual circumstances or for sale, please get in touch. There's some distinctive orange tape on several parts, and they have a serial number to check if it's the same one.

They live near the top of a steep hill near me, in Haight, and use the bike to get to the Caltrain station for a commute to the valley, and it will cost several thousand dollars to replace, so it's a real problem for them. The thieves were pretty brazen, breaking into an occupied apartment building during the night, and didn't take the keys or charger so they'll be lugging it around.

The police are involved, and they'll be scouring for this online too, but since this is such a rotten thing to happen, any help from my readers is much appreciated.