Steves Blog

Hi, I’m and I live in Toronto. I write a popular website builders guide.

I also released two albums last year. This is a good first song to listen to.

You can follow me on Twitter here.

Transsexuality at Coachella: Why the ‘We Exist’ Video is Powerful

Arcade Fire’s video for ‘We Exist’ has Andrew Garfield, playing a transsexual, showing up at Coachella:



Here’s the thing:

We know that this video is good for Andrew Garfields career. It gives him credibility and acts as a counterbalance to having just starred in Spiderman (a major blockbuster).

We know that rednecks beating up a transsexual feels a bit obvious and contrived (and no matter how it’s spun, it’s a bit self-sabotaging for Garfields character to go to a redneck bar).

We know that a rock video taking a stand and “speaking out” against an issue is practically a cliche and has been done a hundred times before.

We know that the politics of sexuality is talked about an awful lot. And that sometimes it feels over-discussed.

We know all these arguments. And in the next few days they will be recycled endlessly in any discussion of this video.

But all these arguments will miss the real power behind this video: which is the universality of overcoming shame.

You don’t have to be a transsexual to know how horrible it is to feel shame. And you don’t have to be a transsexual to know how hard it is to work through shame.

Shame is something every self-aware person eventually has to work through. It’s as much the process of becoming an adult as anything else.

And that’s why everyone gets goosebumps when Andrew Garfield starts heaving and breathing heavily walking up the stage at Coachella.

It’s because we all know the power of what is being exposed here: it’s shame, and it’s coming out publicly.

Note: I’m still not sure the last line of this post is clear. My point is that the way to work through shame is to expose it. Shame is most powerful when it’s held deep inside someone. When it’s exposed publicly, shame loses power. 

Published May 16th, 2014.

The Determined Founder Paradox

 “I would have said awhile ago that intelligence was the most important characteristic of founders, but I’m now sure that that is wrong and that determination is the most important thing.”

- Sam Altman, CNN interview

Here’s a mind-bender for you: try to imagine someone determined towards an unknown goal.

It’s difficult to wrap your head around that, isn’t it?

Why is that?

It’s because determination assumes a firm purpose. Without purpose, determination doesn’t make any sense.

And this is where determination gets tricky for many startup founders: most startups don’t begin with a clear sense of purpose.

It’s why we pivot. It’s why we ship early and often. We do these things so we can create and refine a vision and purpose. It’s why Paul Graham said this:

“The popular image of the visionary is someone with a clear view of the future, but empirically it may be better to have a blurry one.”

- Paul Graham, essay

And so founders have to be determined towards a blurry purpose. This is a paradox.

Paradoxes are tough. They make us squirm. They don’t make sense in our head. We try to avoid paradoxes with easy answers or by becoming ideological (“it has to be only this way!”).

And yet the challenge for a founder is to live within a paradox: to be determined towards a blurry vision.



It’s probably worth explicitly saying this: I am not saying Paul Graham and Sam Altman are opposed (they’re not), nor is this a criticism of either of them. If anything, I’m piggy backing their thoughts. My only point is to emphasize what makes being a founder so challenging.

Published May 13th, 2014.

Marc Andreessen on Bubbles

Marc Andreessen was recently on the very excellent (and cerebral) A16Z podcast. He discussed equity bubbles in terms of fighting the last war and psychological scarring. This is my summary of what he said.

For Marc Andreessen there are three major equity bubbles and crashes in the entire 20th century: the great depression (1929), the inflation of the 1970s (1969) and the dot com bubble (1999).

You might notice that each equity bubble is about 40 years apart, or roughly the span of a generation.

That’s because, according to Andreessen, people who experience an equity bubble develop a strong emotional urge to be in a constant paranoid panic about whatever went wrong last time.

He calls this psychological scarring or fighting the last war.

Historically, what follows is that the paranoid panic prevents the equity bubble from reoccurring within that generation.

We are now 14 years since the dot com bubble and people have been screaming about bubbles for the last ten years.

For Andreessen, all this screaming would suggest that the dot-com bubble generation is not even closed to having passed through.

Listen to the full podcast (on iTunes):

Published May 6th, 2014.

Introducing … Index!

I’d like to introduce you to something I’ve been working on. It’s called Index.

Index helps you discover awesome things in Toronto. To start, it has concert listings. Shortly, I’ll be adding listings for Live Comedy, Theatre, Classes and Teachers.

I love Toronto. It feels like something cool is always happening. Neil deGrasse Tyson is giving a lecture at University of Toronto. Everdale farms is bringing fresh fruits and veggies to the Annex once a week. My friend Cassie is putting on an improv show.

These things are awesome. And I want to make it easier to discover them when they happen.

And thats what I hope Index will do.

Published March 25th, 2014.

Would Apple have come up with iBeacon if they didn’t have retail stores?

I doubt it.

I have a hunch Apple needed to understand retail before they executed iBeacon. And I think this tells you a basic truth about innovation.

In order to innovate in an industry, you need to have a deep understanding of it.

Apple has spent 12 years creating a deep understanding of retail by continually pushing themselves beyond conventional retail. They have the kind of deep understanding of retail that can only come from years of doing it in a radical way.

It is this deep understanding that gave them the sharp insight to know exactly where to apply iBeacon: retail.

They were scratching their own itch.

PS: it’s crucial not to gloss over “deep understanding”. Deep understanding is illusive and is only gained from application.

Published December 16th, 2013.

Are you Idea Guy?

“Hi! I’m Idea Guy”

My favourite stereotype in the world of startups is Idea Guy.

You know him: Idea Guy has no technical understanding but is guns-a-blazing with his amazing idea (which you can hear after you sign his NDA). Idea Guy throws down $30K on his first MVP, while his developers (who’ve been through this many times before) mutter amongst themselves about how delusional his product is.

Idea Guy’s problem is this: he’s caught the scent of opportunity but don’t understand the rules of the game.

It’s easy (and fun) to mock Idea Guy. What is hard to do is to self-reflect and ask, in what ways am I Idea Guy? Because we all are from time to time.

Maybe you run a startup that knows SEO is a major opportunity and wants to hire a consultant. But instead of doing the work of understanding what type of SEO consultant you need, you just randomly email people and throw money at the problem.

Maybe you run a startup with a design problem and instead of doing the work of finding out what makes a great designer, you try to solve the problem quickly by hiring.

Or maybe you don’t run a startup, but you’re always talking about how you could have made so much money if you bought Bitcoins two months ago (or you’re salivating at Tesla stock price). You’ve caught the scent of opportunity, but perhaps you don’t actually understand the rules of the game.

Don’t be Idea Guy. Take him as an example of the way you didn’t go and recognize the scent of opportunity for what it is: a call to dive deeper and understand the rules of the game.

Published November 29th, 2013.

Carl Jung

My own understanding is the sole treasure I possess, and the greatest.

- Carl Jung

Published November 26th, 2013.

Tobias Lutke on the Future of Commerce

Tobias Lutke, CEO of Shopify, on building a business in the highly competitive space of commerce (from his interview on This Week in Startups):

“To build a business that is fundamentally good at thriving in chaotic environments is to experiment and try out a lot of stuff.”

And on the future of commerce:

“Why is Kickstarter successful? I don’t think it has anything to do with crowdfunding. I think that’s a complete misattribution of its success. Kickstarter is successful because it forces the product creator to create a video about the product.

If the people who create the product, tell you … the reason why they went there, why they built it and why this is product needed to come into existence … you have a much more powerful thing.

And that is the problem that [traditional retail] has. When you go into Best Buy they won’t tell you the product story. And [there isn't a] channel between people who create things and the consumers who buy things. There is a [distribution] layer that is just a historical construct that can be shattered. And if it could be shattered it can be very powerful”

Lutke is a very sharp guy and Shopify is the best tool for creating your own online store. Shopifys ambitions are clear- they want to be there for the future of POS too. I for one, am excited to see where they go.

Published September 20th, 2013.

My Newest Project: Locally Sourced

I’m really excited to introduce you to my newest project: Locally Sourced. Just in time for summer, Locally Sourced is an easy way to discover farm shares across Toronto.

Let me know what you think!

Published May 13th, 2013.

The only business class I ever took

One semester, when I was an undergrad, I decided to try out a business class: Business 101. At the end of the semester, our professor assigned us a final paper on Business Ethics.

I sunk my teeth into the assignment. Like most young students, I had strong opinions and reveled in the opportunity to express them.

The professor ended up giving me a 75%. I was choked. I told the professor I thought it was unfair and that he should change my grade.

He explained that I had gone beyond what was required but that I had formatted the title page wrong.

This meant that students who gave textbook “business ethics” answers would be getting better grades than me. I told him that was stupid. He was unfazed. He said you just have to learn to do your title pages correctly.

I left his office steaming that a formatting error could be considered more important than engaging the content.

That was the last business class I took in my undergrad.

Today, Ramit Sethi made a point on his blog that made me want to stand up and clap:

I just don’t care that much about proofreading. I catch 99% of my own errors, and even when I publish something that has mistakes, nobody cares.

I agree big time and it’s cool to hear this from such a prominent writer. Proofreading is too often about exercising control rather than focussing on things that move the needle.

That’s why when you ask for feedback on writing, you’ll receive minor grammar fixes rather than feedback on the actual content.

Or why business professors will dock marks if you format your title page wrong (even if you did a good job!).


Published March 11th, 2013.

New Design

Yesterday I found myself on Medium, Evan Williams’ newest project. It’s a unique take on publishing and I could definitely see myself using it.

Beyond the concept, Medium has stunning design work. I liked it so much that I decided to redesign this blog that afternoon (taking generous portions of inspiration from Medium). It’s not a perfect redesign but it was a fun way to spend an afternoon! Need some inspiration? Try checking out Medium.

Published February 22nd, 2013.

Breaking the Pattern

It’s happened a million times.

A client comes to you with a project. She’s enthusiastic. You get excited about doing a great job on the project. You both establish that the goal of the project is to move more widgets. You’re both optimistic about where this is going.

Three months later, the project is wrapping up. You no longer feel connected to the higher level goal of moving more widgets. For you, the project has become, “deliver a functioning ecommerce website.”

By now the client is overloading you with, what you interpret as, granular feedback. You are both exhausted and just want the project to ship. You both have secretly started to resent each other (just a little bit).

This is not the exception. This is the rule for every software project.

Finding a hundred, little, unsexy ways to fight back against this reality is the right place to begin any conversation about hiring developers or starting a company.

Published January 21st, 2013.

I’d rather freelance for non-profits than startups

When I tell people in the Toronto startup community that I freelance primarily for non-profits I get a lot of patronizing looks. I’ll hear things like:

You shouldn’t take non-profit clients- they’re too much of a headache

Dude, they don’t pay well enough

They don’t understand what you do- so they’re disrespectful of your time

What I want to say (but usually don’t) is that I think my startup friends are full of shit. In fact, if you take the above quotes and apply it to my startup clients THAT would actually accurate.

So let’s take each of these quotes and apply it to startups:

They don’t understand what you do- so they’re disrespectful of your time

This past summer a startup client asked me to come in and work the next week in their offices. I said I would, and did some creative scheduling to free up the week. The Sunday before I started work I received a text message at 10:30pm:

Hey, we don’t need you this week.

Less than 10 hours before I was set to start work. Thanks for respecting my time.

You shouldn’t take non-profit startup clients- they’re too much of a headache

A good chunk of my startup clients are moving too “quickly” to supply appropriate documentation or feedback. So as a designer, it can be difficult to ascertain clear goals from the outset of projects.

In fact, in many cases, I have found that “goals” are developed as we iterate through my mockups. I’ll end up going through several rounds of mockups before the client has an “aha” moment and is able to articulate the goal.

It’s frustrating to have to help clients “sound-out” a goal through mockups. Clients that do the hard-work of thinking through a project before they hire a designer are much better to work for.

Dude, they don’t pay well enough

Guess what? No non-profit has ever asked me to work for equity. Startups always look to subsidize my work with “equity.”

So in conclusion, Clients that are consistent, clear communicators are my favorite clients. I love working with them. Startups that complain about a “talent shortage” should work on getting good at project management and communication. People will want to work with you if you’re good at that.

But in the meantime, I’ll keep working with my non-profits clients.

Disclaimers: I’m not trying to make a hard and fast rule about startups. There are certainly great startups to work for. This is just based on my anecdotal experience as a freelancer. This post also is probably more accurately titled “why freelancing for startups sucks sometimes” as I don’t really touch on positive non-profit experiences at all.

Published December 2nd, 2012.

Business lit

While browsing the business section in Chapters I came across this Guy Kawasaki book. Note the absolutely glowing endorsement from Woz. It reminded me of a quote from a business publisher (found in the the Failure Issue of HBR).

In fairness, I’ve never read anything by Kawasaki :)

Published August 14th, 2012.

Technology doesn’t change the world

Wired: What’s the biggest surprise technology will deliver?

Jobs: The problem is I’m older now. It’s 1995. I’m 40 years old. Technology doesn’t change the world. It really doesn’t.

Wired: That’s going to break people’s hearts.

Jobs: I’m sorry, it’s true. We’re born, we live for a brief instant, and we die. It’s been happening for a long time. Technology is not changing it much – if at all.

From the 1995 Wired interview. Emphasis my own.

This is not a quote that makes you want to leap out of bed in the morning. But at a time where tech startups are celebrated on magazine covers, I think it’s a clear eyed and sober statement.

The startup world is big and exciting. Being part of it gives you a sense of exhilaration and endless possibilities (see: billion dollar buyouts) that the rest of the economy seems short on.

This momentum and flurry can develop into a broader, higher-level optimism in technology.

The kind of optimism that tells you technology brings us closer together.

Or that it’s democratizing nations.

Or that it will develop super-intelligence (admittedly I don’t know much about this).

Technology becomes a convenient stand-in tool for how we will reshape the world. And at a certain point we start to confuse technological optimism with technological worship. It all starts to get a little fuzzy.

Jobs quote, whether he meant it this way or not, is a reminder to reel in overshot optimism. Technology solves a lot of problems. But it is an insufficient answer for what it means to be human. I find it instructive to keep that in mind.

Published July 30th, 2012.

Design your organic listing

Recently, I’ve become interested in adding Microformats to my sites to augment my listings in Google.

It’s got me thinking about Google listings. Listings are actually remarkably compact. If you take a close look, there is a lot of information condensed in a very small area. It’s an interesting design challenge.

I wanted to see how if I could “design” my Google listings. I came up with four variations:

1) Pack it all in - I think this is as much info as you can put into your listing. This is great because you get almost twice as much real estate on the page. The downside (maybe?) is that it’s awfully convoluted. The searcher is looking specifically for a “OnePager Review” and my listing is offeringa lot of superflous information.

2) A little trimmer – I took off the ” | Site Builder Report” as I don’t think it’s relevant to searchers (although it might be if I was a big brand like “Wal-Mart”). I also removed the date. I know the date can be very helpful when searching but I don’t like the way it comes before the description– it’s not very clean.

3) Getting rid of my face - I’d bet that having a face in the SERPs would result in a higher CTR. But I also think it’s superflous. This version gets out of the way and only presents the user with relevant info.

4) Google Classic - The classic, elegant Google listing. You don’t get much real estate on the page. It’s beautiful in it’s simplicity, but it’s likely not enough info to be effective.

This should be tested!

In the past I’ve spent tons of time trying to optimize Adwords ads but hadn’t really considered optimizing my organic listing.

I’d like to try a multivariant test to see what generates clickthroughs. I’d use Google Webmaster Tools which allows you to see impressions and clicks per keyword. Unfortunately, it’d be highly unscientific at best. There’s just too many variables: it’s hard to pin down when exactly Google updates your listings and your position in rankings can shift at anytime.

Published June 21st, 2012.

After two months, here’s what I’ve learned about the Toronto startup community

Two months ago I had an opportunity to have coffee with Seth Kravitz, a leader in the Chicago startup community. At the time I was getting ready to move to Toronto, a city I had never lived in before.

I asked Seth if he had any advice.

He suggested I try to meet as many people in Toronto possible and build my network. He recommended I resist getting a full time job: just take my time and build relationships.

So that’s what I set out to do. I’ve spent the last two months in Toronto trying to meet everyone possible. Here’s what I’ve learned.

1. People are generous with their time

I left Chicago with a short list of people that Seth (and my buddy Jaret Manuel) said I should meet up with.

From that list I sent out a couple tweets. A couple emails. Everyone responded and nearly everyone was available to chat.

Each time I met up with someone I would ask who they thought I should meet next. From there, my list ballooned.

2. People are doing cool things in Toronto

One of my first meetups was with Heather Payne the founder of Ladies Learning Code. An organization doing something totally unique (growing quickly too). And it’s here in TO. Awesome.

I met Paul Dowman at a meetup. Paul is building a Rails consulting company. Paul was super helpful and introduced me to a wealth of contacts in Toronto. Those contacts in turn landed me an (awesome) contracting job.

One of my buddies Daniel McGrady just launched an awesome product, Built here in Toronto. Two days after launching they were on top of Hacker News.

The list could go on. My main point is that from a newcomers perspective, there’s many pockets of exciting things in Toronto.

3. Three things to check out if you’re new to Toronto

Networking in a new city means Meetup will become your new tool. It takes some time and effort to get involved, but here’s three great places to start:

Rails Pub NightIf you’re into Rails, you probably already know about Rails Pub Nite. But if not, know that it’s a can’t miss event. You’ll meet great dev’s in a relaxed atmosphere. Unspace runs the event and they’re awesome. I had a chance to hang out with their team one evening and had one of the most candid, best conversations about Toronto’s startup scene.

Lean Coffee TOLean Coffee TO came highly recommended to me. It’s like a relaxed group conversation. Everyone just sits in a circle and shares startup experiences. I find it instructive and helpful. I guarantee you’ll learn something if you attend.

Toronto Startup Digest - This is not a meetup. It’s a mailing list curated by Will Lam. But if you’re new to Toronto, I highly recommend it. Every Monday morning Will emails out the next weeks events in Toronto. It’s got me to several events I wouldn’t have otherwise.


Published June 3rd, 2012.

Stop asking the question

One of the of best parts of attending Code Academy has been the amount of talks and meetups I’ve been to around Chicago. At many talks though, I’ve heard a similar question being asked: “what makes an entrepreneur?”

So far I’ve heard lots of different answers:

  • “Someone not risk adverse”
  • “Someone with a bias towards action”
  • “Someone who just has a deep passion to do one thing”
  • “Someone who can listen to customers and build what they want”
  • Etc.

Here’s the thing: every time we ask that question I think we’re really asking “do I have what it takes to be an entrepreneur?” and we take whatever answers we’re given and we match it up against ourselves.

Playing this game is a bad idea. It’s bad because we’re poor judges of ourselves. Most of us underestimate what we’re capable of. So I think it’s  best to just stop speculating whether or not you have what it takes to be an entrepreneur.

And best way to stop speculating? I’d bet it’s getting started and doing something …

Published January 25th, 2012.

3 Observations about my first week at Code Academy

I’ve been taking a 11 week course at Code Academy. Code Academy is a collaborative, immersive program that teaches Ruby on Rails for web app development.

1. Being an out-of-towner  (I’m from Toronto) has afforded me a kind of tunnel vision. I  have very little to do for next 11 weeks except learn Ruby on Rails and get involved with the Chicago tech community. It’s refreshing to have a focused lifestyle around one goal (there’s a clarity to it I guess).

2. I feel better about doing work on weekends. This is a weird one. I love working but sometimes feel guilty if I do it too much. My inner voice will say “Steve, don’t be lame. Stop working. Go hang out with people. Have fun.” … the awesome thing at Code Academy is I am in community with a bunch of people who seem to relish working. On both Saturday and Sunday, the classroom had people learning to code …. it may possible that we’re a community of enablers :)

3. I’ve regained an appetite for learning new web technologies. Two thoughts on why:

  • Being a freelance web designer in the past, I did much of my work in isolation. It’s easier to get excited about new technologies when you’re talking about it in a community of people.
  • Learning new langauges (Ruby on Rails) maybe gives ne confidence to learn other new things I may have been neglecting.

Published January 16th, 2012.