Hacker Tourism

Tech strategy consigliere.

Read this first

Two things I wish someone had told me about starting a consultancy

I made lots of mistakes building Unspace. Advance warning will not give you immunity, but G.I. Joe taught us that “knowing is half the battle.”

Billable Viking Hours

  1. There is a chasm of sorrow that starts the moment you hire your first employee and lasts until your team is roughly 10 people

    How many founding partners do you have? Call that n. Stay n big as long as you possibly can. You will soon look back at this era as simpler times that you wish you could go back to.

    If any of your founding partners are not going to stick around, this is precisely when you should figure that out. If you stay n-big for two years, that’s not a bad thing. You’ll figure out what your values are and one day notice that you have a culture.

    It’s very rare for a company to suddenly become design-first if there’s no founding design partner. During the early days you might notice that you...

Continue reading →


How to tell your friend that their startup idea sucks

Someone on Hacker News asked “How do I tell my friend his startup idea sucks” and as it happens, this is something I have a lot of experience with.

Your friend is lucky to have a friend that is willing to tell them the truth; most people are cowards when it comes to saying the most important things until it’s already too late. We’re trained from birth to tell people what we think that they want to hear because it feels good to tell someone that they’re brilliant.

Giving someone the hard truth feels awful. Yet if we only ever tell someone that their idea is great, what do we do when their next idea is actually great? “This one is really really great!” “Last time I was lying but this time it’s actually great!”

A startup is a temporary business structure that exists only to prove or disprove a hypothesis about a market...

Continue reading →


How many watches can one person wear?

Forget “eyeballs”. With so many eager Pebble clones on the horizon, could wrist real-estate bottleneck the Internet of Things?

Synchronize Swatches

At 35 years old, I just barely sneak in at the tail end of Generation X — and most of my friends that are similar in age don’t wear watches.

“Kids” younger than me? They really don’t wear watches. Like… at all.

I didn’t wear a watch for many years, but I grew to really love the design aesthetics of the Nixon Rotolog:

Nixon Rotolog

Later, I fell hard for the LIP Diode:

LIP Diode

Both of these beautiful watches now collect dust because I’m completely dependent upon my Pebble. It’s dorky looking, but it has dramatically improved the quality of my life in a very simple way: my phone no longer rings or vibrates, ever.

There are two dramatic ramifications of this, both of which massively over-shadow any particular...

Continue reading →


Gun bag: good art makes us uncomfortable

Last year, I bought my ex a purse that could get her killed.

Guardian Angel, by Vlieger & Vandam

She’d seen Vlieger & Vandam’s “Guardian Angel” bag at MoMA, and finding the one she wanted to surprise her with became a quest. She was a design expert living in Netherlands, and I don’t know anything about handbags but I was happy to be with someone quirky enough to appreciate such a polarizing accessory.

As soon as we had it in hand, I started to get nervous. The bag was in the US and we live in Canada. I was afraid that shipping it would result in customs cutting into it like morons, so we planned to bring it home from a wedding. That’s when we saw the warning tag attached to the bag with a little chain:

To avoid any problems don’t take your Guardian Angel bag on a plane as hand luggage or to a bank to get cash

Jesus Christ: we’re trapped in the most paranoid country on...

Continue reading →


Introverts: you probably aren’t crazy (but you might be highly sensitive)

Susan Cain’s “Quiet” educated people about the introvert’s social interaction patterns, specifically our need to balance social time with time alone to recharge. While accurate, this is a narrow perspective that ignores the role of what Dr. Elaine N. Aron describes as the “highly sensitive person”.

Paraphrasing from Wikipedia:

A highly sensitive person (HSP) is a person having the innate trait of high sensory processing sensitivity. HSPs comprise about a fifth of the population (equal numbers in men and women) and may process sensory data much more deeply and thoroughly due to a biological difference in their nervous systems. This is a specific trait, with key consequences for how we view people, that in the past has often been confused with innate shyness, social anxiety problems, inhibitedness, social phobia and innate fearfulness, and...

Continue reading →


Value pricing is easy

I used to be a dyed-in-the-wool true believer in “time and materials” hourly billing. I’ve now come full circle, and you should too.

The Price is Right

You already have an hourly rate, so take that number and multiply it by your best estimate of the number of hours it will take to do the work.

$150/hour x 100 hours = $15,000

Now, take that number and double it. Then round up to the nearest 4, in thousands.

($15,000 x 2) + $4000 = $34,000

That’s it; you’re done. That’s what the project will cost.

Everyone is happier.


My rationale in support of time and materials was reasonable: estimates are guesses and in a fixed price project, one party always wins and one party always loses. It’s usually the vendor that ends up taking a bath. If you do great work for your client on an hourly basis, they will happily to ask you to do more.

On paper, this sounds great and...

Continue reading →


Bitmaker Labs forced to halt operations mid-term by the Ontario government

Last week, BitMaker Labs was helping 25 aspiring programmers learn how to build sophisticated web applications in Rails. This week, their efforts are being criminalized.

freedom-of-speech-cc-by-jennifer-moo.jpg

First: I’m an organizer in the Toronto Ruby community. I am not legally affiliated with Bitmaker Labs, but I’ve met with them to discuss their program and I have several friends that were enrolled in the 2nd cohort.

I’m not qualified to say what the Ministry of Training, Colleges and Universities (MTCU) would consider a desirable outcome, or what about Bitmaker specifically provoked their wrath. I do know that we have a desperate shortage of Rails developers in Toronto, that my friends — enthusiastic future tech leaders, having a blast in the program — are demoralized, displaced and unemployed.

I worry for programs run by HackerYou and Ladies Learning Code; there are many similar programs running...

Continue reading →


The Future of Authority

Jesse Hirsh’s excellent TEDx talk on “hacking reality” deserves your attention in light of the ongoing NSA PRISM scandal.

What I like about Jesse’s eerily prescient statements is that he attempts to provoke a subtle, non-partisan activism in his audience. His words compel the listener to visualize their own legacy inside a future in which they do not act against authority.

Absent is the patronizing and smug “I told you so” attitude common in tech media; instead, Jesse points out that the predictable trajectory of centralized power does not make it right or desirable.

Jesse reminds us that on the Internet, even being an observer has an impact. In doing so, he cunningly teaches what Emma Goldman said: “The most violent element in society is ignorance.”

“That first impression that comes from a Google search result is sadly far more powerful and...

Continue reading →


My big performance secret is pinball

I suspect that my love of pinball seems like a harmless anachronism to many people; throwback fun that fits comfortably with my other “eccentric” hobbies like film photography and collecting records. Don’t be fooled: life can be gamed, and pinball is a cheat code.

Ground Kontrol

Scientists say that chewing gum elevates your brain function for a short time period.

I do some of my best thinking (alone) in the shower, but practicality dictates that a shower should only last a short time. Similarly, I enjoy doing dishes; it’s a mindless activity that lets me use my hands, and I can take pride in a job well done. Everyone appreciates it and is generally happy to leave you alone with your thoughts.

Eventually you run out of warm water and all of the dishes are clean. What do you do when all of the gum has been chewed?

“I have come here to chew bubblegum and kick ass…...

Continue reading →


How I became a meddler

A story in which a gifted connector assembled 20 notable smart people in a 14th-century English cottage for three days to figure out how to make the world a better place, one passion project at a time.

20130422-0022.jpg

First, let me introduce the idea of a Meddle: a new approach to solving hard problems that I believe you should be excited about. You can Meddle, too — and it’s important that you do.

Excerpted from the Meddle website:

Each Meddle is a unique gathering of brilliant people, invited to come together and tackle a specific issue. The issue can be anything, in any field, on any scale.

The aim of each Meddle is to conceive, develop and present something that ‘moves the needle’ on the chosen issue. It might be a website or a white paper. It might be a product prototype or a schools roadshow.

We curate and facilitate the event. We choose a wonderful location – which could be anywhere...

Continue reading →