trendpreneur

I wrote this as a comment on SocialPenguin, but thought it worth republishing (in an edited form). It’s fully my intention when able to do so (i.e. not now) to work towards as much of this as I can.

The startup scene in Edinburgh is tight-knit and receptive. You can’t have an entrepreneurial scene that stretches across the whole of Scotland and still works; it’s too geographically spread. Companies need to be in the same building (yay for Appleton Tower), not the same country.

Even from my viewpoint here in Silicon Valley, which is around 50 miles north-south, you have a “San Francisco” community and a “Valley” community — the Valley community is even fragmented, but people make the effort to get to events in central places and co-work from a select few locations.

What we need in Scotland to echo some of the Valley feel is:
- Centralised hackerspace/coworking space large enough to support at least 100 entrepreneurs. Happy Hour every Friday, all local startups are invited. Mailing list for members. Standup “show and tell” demos every day.
- Bring EPIS back! And a similar YC-esque summer scheme targeted at students – do something meaningful in your summer holiday. Ideally lean-style, once compsci students cotton on they can make actual cash and wipe out their student loan in 3 months of summer work, they’ll all start doing it. We hope.
- More funding competitions and hackathon events with real sponsors and real prizes. Startup Weekend style.
- Role models that have actually made it, whether locally or from elsewhere with a good grasp of the Scottish scene and the challenges therein; when I was in Edinburgh there were a surprisingly small number of these around
- Similarly, advisors who have made it in the right sector (say, B2C web startups) and who have experience with Lean. Let’s get Eric Ries and Dave McClure in residence for 3 months, or the next best thing.
- Finally, forging links with angel groups that do invest in this kind of stuff and can overcome the geography, or a local angel syndicate that becomes well educated and aware of the huge opportunities in our space, so there’s a clear path to funding.

So, who’s with me?

I’ve been ruminating a lot lately on focus and what makes me most productive. Here’s a technique that I find effective for enabling you to really dive into one task without stifling your creativity.

My mind comes up with the craziest things while in the middle of other tasks, and I don’t want to follow every rabbit down its hole, nor lose track of these moments of inspiration. So a spin on GTD is needed to get the rabbits under control.

The solution: a parking lot.

(I’d say “car park”, but it doesn’t really sound right. This time, the Americans win.)

In brainstorming and planning sessions, a parking lot is an area — flipchart, whiteboard, post-its — where ideas and avenues whose time is not yet now are held for future consideration. When you’re done discussing whichever task is at hand, you return to the parking lot and pick out something else to discuss.

The parking lot for ideas works in much the same way.

In practice

I implement this pretty simply. I have a Google Doc titled “Parking Lot” (yes, I am a font of originality) and when I’m diving into a specific idea, anything that crosses my mind as a potential avenue for further explanation gets added to this doc.

For example, today’s parked ideas include ways to manage multiple Twitter accounts more effectively, a note to redesign a site I’ve been sitting on for some time, a reminder of an idea I’ve documented elsewhere but need to pull together, and the suggestion “create a parkinglot site to manage ideas better”.

I used to keep all this in a Moleskine notebook, and love the tactile feeling of scribbling exploratory notes down, but the fact I didn’t always carry it around — and couldn’t easily search and access its content — deprecated it in favour of the online doc.

Successful parking

Discipline is the hardest part of this process for me. When I’m on something really juicy, I want to abandon what I’m doing to really get stuck into the idea. If I revisit it a day or so later, the spark is often gone (which in itself is a great test of an idea, no?).

As with GTD methodology, the important part is knowing you’ll check and follow up on the parked concepts, whether at the weekend, at a hackathon or just late at night when you have itchy fingers.

Another important thing I’m personally aware of is that notes make a lot of sense when I write them, but less sense in future. Context, URLs, notepads or other docs with supporting thoughts (don’t want to clutter the lot too much) are all helpful so when I look back and see “Improve Twitter”, I can dive back into exactly what I was thinking when I wrote it.

Tools and platforms

This’d be an awesome first use-case for my robot brain, but that’s in the parking lot for now. (Ah, self-reference!)

Google Docs, as mentioned, works great but is pretty unsophisticated.

Evernote might well work for you, especially if you already have it in your workflow. Tie together a snapshot on a mobile phone with a note from a Chromebook with a full business plan .PDF…

Sometimes a bookmark manager like Pinboard with a note-to-self is all you need to rediscover an idea.

Moleskines and paper or post-its could work — I sometimes write notes and ideas in whiteboard marker on mirrors and windows around my house. Just be careful about cataloguing them!

Dropbox-based text editors across platforms would be an interesting spin on the Google Docs. You could drop supporting documents into the Dropbox folder, too, but it’s less full-featured than Evernote.

Update: Jay on Twitter points out Workflowy, which is an online list-writer app that looks good for this sort of thing, too.

Or for the console-savvy, text files on a remote server accessed with vi and screen over ssh could be all you need.

Ultimately, it doesn’t matter what tool you use — it’s what you put in that counts. As always.

So, park your ideas, focus, finish up and revisit the parking lot. With practice, this becomes second-nature, and you get a great list of things to do when the aforementioned itch strikes.

The setting: New York. My partner-in-crime Craig and I are on an impromptu vacation of sorts, realising it’d otherwise be 3 months until we saw each other again.

Friday evening, after an intense and heartfelt conversation: “Let’s get married!”

“Here? Now?”

“Why not? It’ll be cheaper and less hassle!”

18:42 – Update Facebook status to “Engaged”. The congratulations flood in.

We discovered that in the state of New York, a marriage license is available for $35. You can get married as soon as 24 hours after obtaining it, and as easily as just turning up at the City Clerk’s office with a witness. We sanity-checked: we had the right forms of ID. We could take an extra few days of emergency vacation. We knew a few people in the city we could theoretically ask to come along, though most of them were far enough removed acquaintances that they’d find it a little weird.

But then, of course, I got a little carried away. Think Bridezilla on a deadline.

“Let’s do it in Central Park! There’s this site – they do elopements. They could marry us anywhere!”

And so the crazy train started rolling.

We decided not to commit to anything before we had the license, just in case our pesky Britishness or my lack of passport caused problems. Nevertheless, we — ok, I — spent the weekend glued to Yelp and Google, researching everything, and even forced my shiny new fiancé to help me scout out Macy’s on 34th to lay the groundwork for the shopping spree of a lifetime.

As you can see from the photo above, we got the works. Tuxedo hire, dress, accessories, jewellery, bouquet, hairdo, photographer, limo and we even arrived at the pavilion by horse and carriage. Officiant and license, of course; champagne goes without saying; and a lovely dinner to round the evening off.

No veil, no cake, and no relatives squabbling over old feuds. No clichéd dance or cheesy toasts. Oh, we’ll have all that eventually – the family won’t let us get away without some kind of reception on our native shores – but it was nice to pull off something so personal and yes, insane, over 3000 miles away from home.

Pulling off the organisational feat of a lifetime

Most brides-to-be have a year or more to plan, I’m told.

I had 48 hours. We got the license at around 1:30pm on the Monday, and were married at 2pm on the Wednesday.

Before we had the license, I’d emailed cancellable stuff: the officiant, who was away all weekend, and two photographers, of whom I picked the most creative (and also cheapest). Sunday I finally had my first conversation with the officiant, who was lovely, but somewhat akin to the telephone calls I have with my grandmother – lots of repeating, shouting, and random irrelevancies about mainframe computers. Still, we didn’t have time to get a friend ordained by the ULC or find a sympathetic nondenominational minister, so she’d do. (And did, nicely.)

Also, as we’d extended our stay in New York an extra week, we spent much of the weekend panicking about ending up sleeping in cardboard boxes and walking home. The return flight I’d booked via Continental had a clause I’d completely missed, the telephone support guy being very understanding — “yeah, most people never read that stuff” — but similarly unhelpful: “you agreed to a non-refundable non-movable fare, madam”. And so, the first appearance of the star of this show, Mr Platinum Credit Card, to book a brand new flight from vayama (a site I’d not heard of but which was $1000+ cheaper than all alternatives on a one-way ticket).

For the accommodation, AirBnB superhosts came through like a dream. I’m a long-term user and fan of the service, but the problem with New York seemed to be a combination of unresponsiveness and price; we needed replies, like, now. Fortunately, after splitting our week in two, we found two places that were well-located, within budget and seemed nice — and they were both incredible. Our first host, Alastair, completely made us feel like family and cooked a fantastic breakfast for us every morning! I can’t big up AirBnB enough, even though the “standby” list got us nowhere.

48 hours to go…

Monday was an interesting day. While waiting at the Clerk’s office, I made appointments for hair, nails, and — thanks to the Yelping — managed to get a same-day appointment at a bridal boutique. This took a surprisingly small number of total calls — I love New York. Though it’s a little bizarre how some places are closed Mondays.

The boutique was a long shot, and more based on its promising Yelp reviews than my hope of finding a dress. I had a plan involving Macy’s, but thought I’d head along to see what it was like. The phone conversation pretty much went like this: “Do you have any off-the-rack dresses in a 12 or so? I need it for Wednesday” “Sure, we have a couple”. Hopes weren’t too high.

Amazingly, the Bridal Garden delivered. The assistant had already put two dresses aside, and the first one fit near-perfectly, was exactly the right length, and looked incredible. This was the moment when it hit me: not having the license in my hand, or arranging time and place with the officiant, but seeing myself in white. Wow. I’m getting married.

I couldn’t be choosy; I bought it, with a bonus 15% discount, and walked away with my new treasure wrapped in paper and plastic.

Alternatives I was considering include David’s Bridal, which is quite close to the Garden — I’d scouted it the day before, and not been impressed, but that’s possibly because the selection was so large it’s a little overwhelming. The dresses also felt fairly cheap, but it’d be a good one-stop shop for everything at once if you’re really in a hurry. Macy’s had some nice white dresses, and I hear J-Crew do a good bridal range (but there wasn’t one in New York that carried it).

We also managed to find a tuxedo rental place, Baldwin Formals, that came up from a Yelp search for “last minute tuxedo” and sure enough, offered a tuxedo package to be picked up Wednesday morning. And a couple of streets away in the Diamond District, a jeweller was preparing a couple of white gold rings for us at a price he haggled out of his manager — no doubt a show for the crazy Brits with the credit card, and I was crossing my fingers that the shop would even be there on Wednesday, but so many of the over-friendly, beckoning windows along that street were more offputting than encouraging.

24 hours to go…

Tuesday I had to head into work (we have an office in Chelsea) which made logistics interesting. I spent most of the day hunting sight-unseen for accessories, getting my nails done at Bliss 57 (online booking is awesome), and arranging the remaining pieces. I booked dinner via OpenTable. I was planning on using Uber for transportation, but New York traffic is what it is, so I picked a car service to take us to the park. I gave up at the horrendous price of bouquets on the phone, so ducked into the first flower shop I saw and asked them to create one. The price was still pretty horrendous. I guess white ribbon is hard to get or something.

Macy’s and Century 21 came through on the bag, jewellery, undies (who normally carries around a white strapless bra? Not I), umbrella and pashmina front, though I spent a futile hour in the Fashion District hunting down lace for an impromptu shawl that I decided was too costly in the end, and wasted more time hopping into a few bridal-looking shops in pursuit of hair accessories. I decided in the end to let my hair be, especially with the rain on the horizon. Note to self: don’t overcomplicate when you don’t have time to even complicate in the first place.

After work, thanks to New York’s late opening hours, I managed to triumphantly find a pair of shoes that fit — hurrah for searching in my size on the Internet beforehand, and boo for having size 11 feet in the first place — and we were ready to go. Whew.

6 hours to go…

Wednesday morning was a triumph of todo-list mastery, military precision, and SMS coordination. In jogging gear, I dashed from florist to hair salon to ATM to our home base to change, while Craig ran around a much better-planned route to pick up rings and tux. I briefly entertained the notion of ducking into a beauty bar for makeup, and then came to my senses as I saw the clock.

Amazingly, everything I’d bought at the last minute fitted, and bizarrely all the accessories I’d picked were the same exact shade of ivory as my dress (seriously, it’s spooky). Craig’s tux fitted like a charm, though the shop clearly thought he was off to a funeral rather than his own wedding; the rings existed, and weren’t made of tinfoil; my hair was still in one piece, and the makeup I’d had to buy didn’t make me look like a clown.

We stepped out of the trendy Hell’s Kitchen loft we were staying at, with a sendoff from our fabulous host (whose wife, a florist on the side, had made a buttonhole to match my bouquet!), and into the waiting car (yay, it turned up!).

Everything worked, and the day was full of small victories. Most of it was on time, and we’d long since given up on perfection so we didn’t care. The rain interfered a little, but not too much, and I was so stunned it was a) actually happening and b) not a complete disaster that I was happy to get soaked. The hem of my dress is coated in Central Park mud, and I still haven’t got around to organising a dry cleaning back at home, but we pulled it off — from ceremony to champagne to celebratory dinner — and I thank the Internet for making it all possible. Of course, nothing goes quite as planned: we gatecrashed the Plaza (if buying $26-a-glass champagne counts as ‘gatecrashing’) instead of a trip to the Brooklyn Bridge, but we were too happy to care.

Wednesday, 3:30PM – Update Facebook status to “Married”.

The “WTF”s flood in.

Afterword

This industry prides itself on long planning, expensive everything and over-the-top traditions. We had some traditions, bits and pieces that were feasible and meant something to us, but the joy of time pressure is it makes you realise what’s important. Our thinking went like this: what’s the minimum we need to make this happen? What’s the minimum we want? And what’s the icing that the silly female half of this dynamic duo would kind of really like?

We only needed a ceremony with a witness. We wanted, for various reasons, a funky location with plenty of photos to share with the many who couldn’t be there with us. And I, in my feminine frippery, wanted something nice to wear (having just said that Friday I’d be happy in jeans and a t-shirt… caught in hypocrisy!), and that entailed hair, shoes and all that jazz. Plus, I wanted a challenge.

You don’t need to bow to the demands of the wedding industry, but do note that as a cost-saving venture, doing everything at the absolute last minute does not come cheap. I doubt (well, after this experience, I think it highly improbable) you could organise a full reception for 100 people in 48 hours, but a quiet ceremony in a white dress is easy enough. Embossed invitations and a ceilidh band? Not so much, but why not give it a go. Just be careful if you’re on a budget!

I’m sure there are people out there with even crazier stories, and I can’t wait to hear them all.

This has been a long and personal post – regularly scheduled programming will resume shortly. Feel free to contact me on jennie at trendpreneur dot com if you are planning a similar crazy adventure and want to hear more or tell me your story.

This got too long for Twitter, where I extended my frantic googling and trial-downloading to take advantage of the time-honoured crowd. (Perhaps I should try Quora or other platforms, too?)

I want a robot brain.

More specifically, at least in my current task context (brainstorming, research and planning), I want an app that is a hybrid between the following:

• To-do list/task manager
• Project manager
• File, asset and research assistant
• Bookmarking service
• Inspiration library and mood board
• Portable note taker

OK, not asking for much.

Let’s dive into the use cases, though – I’m pretty certain there is some combination of existing apps that can do this, and part of the problem is finding the right app.

The big picture? Keeping track of my fledgling business ideas while keeping everything that inspires me in one place. The content I want to have at my fingertips ranges from PDFs to websites, online video, images, scrappy notes, code fragments and git links, even upcoming events.

Project brainstorming

Enable me to map out a project’s sub components and tasks while brainstorming – no need for a fully fledged GTD system, but a way to manage items in lists well at the top level is helpful. One issue here is the content is a mix of tasks and more “permanent” items, an example being:

• Register cool domain name (task)
• Domain name brainstorming (list of words and some URLs of domain name generators, maybe screenshots or pastes from those)
• Existing unused domains (list)
• Expiring domain searches (URLs, perhaps even calendar events!)

Low tech: Bullet points, post-its

Higher tech: Things, Google Tasks, Remember the Milk

Information collation

As seen in the example above, a key thing for me (and really, the first attribute I’m looking for in the Dream App) is managing a combination of notes, websites, pictures, perhaps even calendar events, emails, Google Docs and PDFs. All of these are technically attached to the main task “find a cool domain name” but I want to keep them sticking around for inspiration.

This leads on to the “mood board generator” kind of area where I can just have a task titled “New site!!” and attach a ton of images to it, then view them in awesome-style visualisations to create a mood board of what I want without any actual work. (This in itself is a quick weekend project I’ve been meaning to build…)

The main thing here is peace of mind. I want to go into my robot brain app and know that everything I ever thought would be relevant to my domain name search for a new social mobile location-based app with pirates is in there.

Low tech: Folders.

Better: “Research” tools – I’m currently trying Scrivener after evaluating a few others like Yojimbo which didn’t fit my head so well.

Information capture

The flipside of this is, of course, capture – and this is where I am banging my head a little bit with the current marketplace.

Here’s my ideal flow:

Ooh, cool Flickr picture! hit single button and it goes into brain

Ooh, nice informative TED video! hit single button and it goes into brain

Ooh, fun article on Hacker News with great comment thread about choosing a domain name! hit single button and it goes into brain

Ooh, nice apartment on Craiglist! hit single button and it goes into brain

Ooh, domain name generator site! hit sing-.. you get the idea

Here’s the magic I want to happen:

• When I magic-button a Flickr page, I want the image to get saved locally, the author name to be saved somewhere (for future attribution), and ideally the tags, title and description pre-populated (having a ton of 123859457595_3981201202o.jpg around is getting old)
• Similarly a Hacker News page should have the article link run through Readability and text saved locally, original URL saved, and the entire comment thread archived locally too.
• Craigslist pages should definitely be cached locally (whether it’s a cool apartment or a good deal you want to compare, expiring content is bad)
• A straight up bookmark (domain name generator site or web video) is fine to save as-is, importing Delicious tags would be a nice bonus. I actually dislike services that ‘bookmark’ by web clipping, but maybe that’s just me. I’d rather opt in to clipping the content (and automatically clip stuff like HN and Craigslist) than automatically try to cache everything.

To tag or not to tag? I don’t want tagging to be the user behaviour this centres around. We’re more intelligent than that. Maybe tags would be an extra bonus, but not the core way of finding information. (This is why Yojimbo is not working for me – my mind just doesn’t work that way.)

Low tech: Just use Delicious* or Evernote

Better: Custom pipeline between Delicious and end point which does cool stuff to specific content. (hmm, this is another standalone app…)

*I mean any delicious-like service here, though Delicious’ tag library is nice.

Note taking

Note taking should be as low friction as possible. Using an app on iPad, iPhone or Android, emailing myself, even SMSing… a Chrome app, a method of importing .txt files… there are a lot of places to take notes. I’d want to support as many as possible.

Low tech: import txt files from other note programs

Better: import emails, sync txt files via Dropbox from iPad/iPhone/Android apps (eg. Simplenote)

(Aside: the notion of a ‘universal capture’ tool has been tried many times, and I haven’t yet given all of the contenders in that space a go, but suffice it to say almost all the time when I want to grab a thought when I’m back at my desktop, I just email myself. I want to not do that.)

Challenges

There are a ton of UX and implementation challenges, but I think the biggest is simply going to be figuring out an easy way to navigate the content. My mental model basically has this as the root “item list” which itself leads into sub items, but this already throws up some issues: the world isn’t strictly a tree, and often you’ll find an item belongs in multiple categories (hello, labels/tags) or be looking for it in the wrong place.

How to deal with content from different sources is also an issue. For example, should quick notes taken on the iPad, and new bookmarks, fall into an “inbox” and need later processing? Or should you be able to save them directly to a topic (in which case you need the entire structure to be online somewhere)? Where does the data ultimately live – in the cloud, or locally? If you’re dealing with potential business ideas or other sensitive information, do you really want it in the cloud on someone else’s server?

Sharing is the third major point that springs to mind. Sometimes you want to share stuff (I want to share my folder of “Cool apartments on Craigslist” with my other half, but I don’t want him to see the collection of potential birthday present ideas in another folder). Sometimes you want to publish – throwing up my mood board to the designer working on my site, or a read-only collection of “how to learn Ruby” items to Hacker News. Sometimes you want stuff to be completely, utterly private. Hard to get right.

And so…

As mentioned above, I’m trying out Scrivener – it’s a writing app, and my ultimate goal is to come up with some proposal documents, so that just about works for me. It lacks in the universal capture department, though. So I’m continuing my search for other options – but it’s hard when it’s not quite clear what I’m looking for. A research tool with online capture? A bookmarking service with local annotations? A todo list with metadata?

Let’s just call it my dream robot brain, and leave it at that. (Though sadly there aren’t any relevant hits on Google for that, but the query does return this Asimov story. Enjoy.)

Addendum: Why don’t you build this yourself?

Maybe I shall. (Though right now, my skills would lead this to be a cloud app, which goes against my core “native app for data security” requirement… and yes, funny that a Chrome OS user would want a native Mac app, hm?)