(re-posted from The Hack Academy)

Ever since coming back from bouncing around the world, I’ve been mulling over the cost of constantly changing up a routine. While traveling around is amazing, with change abounding – it’s really hard create a flow to your day. I find when people both work and travel, they tend to do neither one particularly well.

With these thoughts in mind, I popped open Manage Your Day To Day: Build Your Routine, Find Your Focus, and Sharpen Your Creative Mind, a book which was highly recommended to me by a friend.

The Book

The book is authored by self help gurus 99u, and it had a profound influence on me – specifically about structuring my day for maximum productivity. Below are the top 10 things that I learned from the book.

1. Start Your Day With Flow

My biggest take away from the book is to start your day with an un-interrupted period of creative work, ideally for 90 minutes. This sets a good pattern for the day and we tend to do our best quality work when we are well rested.

This period, ideally should require no external inputs and should focus on work which contributes to your long term goals. So this would exclude meetings, responding to emails or picking up the phone.

The book suggests working on projects which are well defined like writing a blog post or coding up a portion of a website during this period.

I’ve been trying to do this for the past week and have noticed I’m significantly more productive and happy overall with how my day has gone!

2. Associative Triggers Tell Us To Work Or Play, Choose Your’s Wisely

The book also mentions that associative triggers tell us if we should work or play.

Why else do people let their guard down with a beer in their hand but not in the office? Our brains have learned over time that we socialize in a bar but we get shit done in the office.

If we’re working from home or in even in the office, the book suggests establishing the triggers which tell our brains what mode we’d like to operate in. If we do the same routine over and over before we get down to productivity, our brains learn what should follow after the routine is completed. If the routine isn’t completed, our brains will actually crave the completion of the routine and be frustrated with us if we don’t complete it.

For me – my productivity routine has become cleaning my desk, setting up a cup of coffee next to my laptop and putting on some light background music before getting to work.

3. Build Renewal Into Your Day And Week

Sleeping on the job

Why is it that I’m not nearly as productive on Thursday as I am on Monday? I think this stems from being renewed on Monday but feeling somewhat exhausted from the week on a Thursday.

According to section authored in the book by Tony Schwartz, our capacity for work is limited and we need to guard this capacity to work on the most pressing things and renew this capacity each day and each week.

We can build this renewal into our day via breaks, naps, exercise, walks and lunch. We can build this renewal into our week by doing fun things which are completely unrelated to work – for me this includes dancing, cooking and just doing a thai dinner watching a movie.

4. Establish Hard Edges To Your Day

The book also suggests creating a routine for our work day which includes hard lines to start and end our day.

Work generally fills up the space allotted to it, so if we have a lot of time allocated to a task, we tend to slack on the task until our deadline hits.

He also feels that the hard edges make us naturally prioritize doing things outside of work, which ensures we are renewed for work the next day. He mentions that workaholics are much less productive at work than those who take time in the nights and weekends to renew themselves.

5. Harness The Power of Frequency

We are what we repeatedly do. Excellence then, is not an act, but a habit – Aristotle

According to the section of the book authored by Gretchen Rubin, we tend to over-estimate what we can do in a short period and underestimate what we can do in a long period, provided we work slowly and consistently.

She suggests embracing working in small increments for months on end, realizing that in the end the frequency will pay off. Slow and steady wins the race.

She mentions several other pros to frequency:

A. It makes starting easier: picking up where you left of is easier than starting fresh

B. It keeps the pressure off: when you’re producing something everyday, we are more at ease with just getting a rough draft out. We can just pick up where w left off tomorrow.

C. It sparks creativity. When we work on something regularly, you can’t help but think about the project in the back of your mind. The times when we usually get our best creative thoughts is usually not during the time which isn’t dedicated to the task but rather in the time where we are focussing on something else – for me, this is usually on a walk or in the shower!

D. Frequency nurtures frequency: When you get accustomed to working in short blocks, you give yourself permission to work in a short block more frequently – you don’t need to block off a day to getting something done!

6. Realize the Cost Of Distractions

If we’ve established that our focus is really a limited commodity, we should be doing everything possible to harness this focus and only direct it to the things which matter most.

Unfortunately, most of us – myself included, tempt ourselves with distractions nearby and allow ourselves to be drawn away from our big tasks to checking facebook, email or our phone, thinking “it will just be a minute.”

The problem is that we don’t realize that the minute is really a lot more than a minute since the shift in focus causes us to completely lose our train of thought and worse – lose our flow. Further switching tasks can send us down a rabbit hole where since we are already distracted for 1 minutes, we allow ourselves to be distracted for 2 or 3 and to do our carry out our full “distraction routine”! For me my distraction routine goes from email -> facebook -> Tech Meme -> Hacker News. The routine is hard wired in my head, once 1 is checked, I crave checking the rest…

There have been many studies which have shown we all suck at multi-tasking. One showed that the human mind can only truly multi-task when it comes to automatic behavior like walking. Another showed that people took 25% longer to read a textbook when they were constantly being pinged with IMs.

I need to banish multi-tasking from my life. But first, just give me a sec… there’s a shinny thing over there.

7. Tame Your Email, Facebook + Smart Phone


Once we realize the cost of distractions, we need to re-work our tools to harness our focus rather than take it away. While technology has allowed us to stay better connected than ever before, this connectedness is also causing us to lose our creative focus. The biggest culprits are email, social media and our smart phones. Apparently, we on average spend 28% of our day on email alone!

Dan Ariely suggests that we have gotten addicted to email, social media and our smart phones through “random re-enforcement”. Mr Ariely explains that while normally it isn’t that exciting to see updates on our smart phone or our email – from time to time, it’s very exciting. This excitement, which happens at random intervals causes us to keep coming back to check for new things all the time, hoping to find something exciting. Before we know it we’ve established a routine of checking for an excitement when we have a lull of activity.

Mr Ariely suggests that the best way to get out of this habit is to keep these temptations as far away from ourselves as possible. Therefore he suggests sticking to defined times for checking email and closing our email and facebook while we focus. He also suggests turning off your smart phone.

8. Appreciate Actively Doing Nothing

You can do anything, but not everything” - David Allen

Next time you ride the bus – play this game, count the number of people NOT looking at one of their digital devices. I’ll give you $5 of you count over 20%. I’ve noticed that we look at our phone constantly and one of the book’s authors, Scott Belsky, suggests that there is a significant cost in doing this.

He says that as a culture, we have made processing information at our fingertips such a priority, that we have de-priorized the world which is directly in front of us and minimized the value in doing nothing.

This causes us to be less present in the moment and become both much less accessible to others, reflect less on ideas which are already brewing and miss opportunities which are right in front of us.

This constant processing of information also takes away from a natural process of reflection which most of us engage in when we are not being stimulated. This causes us not to draw the connections, which would otherwise be obvious, if we would just reflect on them in unstructured moments.

9. Let Go Of Perfectionism

The perfect is the enemy of the good. - Voltaire

I had an old boss, Mark Mydland, who constantly encouraged us to not let the the goal of creating something great, get in the way of moving the ball forward.

The book too harps on perfectionism, stating the perfectionism often paralyzes people in their creative workflow. These are some of the problems:

A. Refusal to start: since the end product must look amazing, there is a very high bar to starting any project, since it must look amazing at the end.

B. Refusal to finish: since the end product needs to be perfect, projects tend to drag out almost infinitely.

I’ve personally found that a better approach is to look at everything as a “work in progress.” Is this blog post done? No! It could be edited for the next 10 years – but is it good enough to publish on some low traffic blog which only my mother reads (hi mom!) – absolutely!

10. Invest in Building Willpower


At the end of the day a lot of these habits come down to nurturing the self discipline to follow them. This requires developing our self control muscles.

Studies have shown that willpower has a finite capacity and if we exhaust all our willpower, we will give into temptation much more easily.

We can however increase the size of our willpower reservoir by strengthening our habits in other areas of our lives un-related to work. This can include exercising when we say we will, going to sleep when we tell ourselves to or even just developing the habit of flossing!

If we increase the size of our willpower reservoir, we will find that our capacity for doing hard work will naturally go up as well.

PS – Habit Change Is Hard

One thing to note – as I typed out this list, I broke almost every single habit! I checked my email first, I got distracted, I was a perfectionist about re-writing this list, etc etc. While it’s good to have high ideals, I’m also starting to understand that many bad habits have been developed over years and years, and to replace them, will similarly require years and years of practice.

Rand Fishkin’s closing presentation at Mozcon left me thinking. In it Rand gave a scathing review of current internet marketing practices and gave a strong call to action that if you really want people to talk about your stuff, you need to be Transparent, Authentic, Generous, Fun, Empathetic and Exceptional.

While each one of these principles are super interesting, it’s the principle of Generosity that has stuck with me the most. I’m realizing that all the companies that I admire for their marketing, have a strong component of generosity.

Below are the ones which I think stand out, and why I think generosity makes good business sense.



Dropbox, from the time they launched, gave everyone a free 2GB of storage space. While this may seem like nothing right now, when they launched in 2008 it was quite the hoopla. Not only did they give you 2GB but every time you helped them by telling others about dropbox, they helped you by giving you another 250MB of storage space. This created viral growth and allowed Dropbox to get in foot in the door to potential customers for their paid SKU.

They currently make more than 240 million annually only 5 years since launching.

Macklemore & Ryan Lewis


Macklemore giving Seattle a shout out

In a world where hip pop is dominated by rappers talking about “their ho’s in different area codes” and each seems to just be striving to amass more and more bling, Macklemore has been rapping about social issues and standing out from the pack.  In the process he has created anthems for under-represented communities including thirft shop shoppers and gay marriage supporters.

Further, Macklemore takes every opportunity possible to mention Seattle as an awesome place to be – including using Seattle as the backdrop of every video, mentioning Seattle in many songs and praising the city in interviews. Naturally, every Seattle-ite pays Macklemore the same respect and Tweets/Shares and shouts out Macklemore whenever possible.

On his home turf of Seattle, all of their concerts sold out within 15 minutes.


Lululemon yoga class in store

Yoga in a Lululemon store

How do you get girls to spend $100 on yoga pants? By making a damn good set of yoga pants, riding the yoga wave and through smart marketing.  Lululemon provides no sales but has managed to create a raving fan base.

The get the word out about their great product, lulu gives a 15% discount to any fitness instructor, causing the majority of yoga instructors to always be decked out in lululemon. This naturally shows their students what they should wear if they too would like to become an expert.

Lulu also puts on free fitness themed events like scavenger hunts and yoga in the park.  They also provide free yoga classes in their stores throughout the country. This has helped the company to become associated with everything yoga represents including fitness, health and good looks.

I currently think of them as one of the most exciting companies which has come out of Canada.


Who could forget the creators of TAGFEE?!

Moz maintains generosity as one of their tenants. They demonstrate it in numerous ways including: providing free lessons on SEO, free webinars, free recordings of some conference sessions, free video tutorials and free guides to SEO best practices.  They also regularly recommend competitor products and let users use their product for free for a limited time.

All these practices pay dividends in various ways including making thought leaders in internet marketing. They also allow Moz to get a foot in the door to people who are interested in SEO and Internet marketing. Once the user gets serious enough about SEO, it will seem natural to use Moz’s tools.

Moz was also nice enough to give away a Roger figurine, the Moz mascot, to every Mozcon attendee.  Since everyone loves the company so much, it has led all the participants to take him home + snap photos of Roger in different settings and share out the photos via social media, causing the buzz from the conference to last much longer than it would have otherwise.

A site showing Roger all over the world has even popped up. These are a few of my favorites:

Roger in a datacenter

Roger in a datacenter

Roger on Coke

Roger made some friends

Why Does This Work?

When somebody pays me a compliment, it feels natural to pay them a compliment right back.  When somebody smiles at me, naturally I smile at them as well. If somebody gives me a gift for a birthday, normally they they receive one as well when their birthday rolls around. Reciprocity just seems to be human nature.

When a business provides us something for free, I think it naturally leaves the customer searching to reciprocate in some manner.  It then feels natural to tweet out the brand, recommend them to a friend or start using the product when you’re ready.

I’m going to try to think of ways to be generous in all my marketing efforts going forward. Not only does it feel good, it’s good for business!

Should You Outsource?

Should you outsource?

I’ve gotten in the habit of paying freelancers to help me do things. While I would prefer not to spend the money, I figure that most talented founders could be commanding great consulting rates – so it seems silly to work on tasks that someone else could do for much less.

That being said, I’ve found it consistently difficult to muster up the courage to pay for things when there isn’t a lot of revenue coming in. While difficult, I think it’s necessary to pay freelancers to do some of our work in order to guard our time and rid ourselves of as much work as we possibly can.

I’ve spoken about the merits of outsourcing with a lot of friends. Many are excited about jumping on-board but don’t know where to start. So, I decided to write my ultimate guide to growing your startup with freelancers.  Below, I go through the types of work I have been successful with outsourcing, the best place to find freelancers and give 9 lessons I’ve learned along the way.

The Types Of Work You Can Outsource

Before we get started, just to wet your appetite a little, I thought I’d share a few things freelancers have been helping me with lately.

  • I recently wanted to convert a new WordPress blog design into a functional WordPress theme, so I found a developer in Greece and paid him $20 an hour for 8 hours of his time to code it up.
  • I was afraid to publish blog posts on my personal blog before they were edited so I found a US based work from home mom to edit them at a rate of $10 an hour. She usually takes 30 minutes (or $5) to edit each post.  She edited this one in 50 minutes! (Thanks Crystal!)
  • I wanted to chat with people who have taken an online course, so I paid them $2 each to speak with them for 10 minutes! One simple request on Mechanical Turk had them calling me rather than the other way around!
  • I had a request for 10 paintings to be stretched and framed for a bulk purchase on  Art Sumo, so I found a laid off painting framer with 20 years of experience frame them all for for a whopping $100!

Where To Find Freelancers

I’ve found oDesk, Craigslist and Mechanical Turk to be the best places to find quality freelancers. I use oDesk for finding developers or virtual assistants, Mechanical Turk for doing market research and then I use Craigslist for everything else.

oDesk: oDesk is a goldmine for finding quality developers in hard-to-reach places. It provides a complete package: searching for freelancers, arranging contracts, interviewing them, and then tracking their time when they are working!

Craigslist: Craigslist can be amazing for finding people to do odd jobs in addition to freelancers. Two tips: some cities charge for placements, so just post jobs in the gigs section (which is free). And – if you’re ok with freelancers working from anywhere – be sure to add the freelance wanted post to other Craigslists located around the world. Canada in particular is a great place to find talent since the population is highly educated but there are fewer tech jobs in general.

Mechanical Turk: Mechanical Turk is a great tool to do customer research. While I initially assumed that the site was filled with Indians trying to make a buck, it turns out that the majority of workers are from a wide income range in the US. For specific details, I’d suggest checking out Customer dev labs’ overview of doing customer research via Mechanical Turk.

9 Practical Tips

I suggest you follow these nine practices when hiring freelancers:

1. Interview through sample projects

Finding freelancers can take a lot of time. Not only do you need to post the job and review each submission, but the back and forth required to vet candidates can be time consuming. I am therefore a fan of interviewing candidates through work samples which takes a maximum of an hour’s work to produce.

Interviewing a freelance writer? Have them write a 500 word blog post. Interviewing a front end developer? Have them code up a static HTML page from a PSD. Interviewing an editor? Send them a poorly written blog post and ask them to edit it.

While it’s possible that some candidates will refuse to do samples, I’ve found that this itself is a good test of the attitude that you’ll deal with over time. If the sample work took a lot of time, or I thought I might use it, I’ve paid candidates for interview samples. Even if it is $20 per sample, it’s probably money well spent since it can save you a significant amount of time in by glancing over samples, rather than spending hours interviewing all the various candidates.

2. Get developers from Eastern Europe

I have consistently found that the best developers come from Eastern Europe, and it’s best to work with individual developers rather than working with an organization.

I have found that organizations provide little additional value over direct contact with the developer. Further – they also introduce complexity and cost since they ask you to communicate with two people, rather than one. They also cost more than dealing with the developer directly since they include a management overhead.

I highly recommend searching for developers from Eastern Europe (Russia, Moldova, Ukraine, etc.) For some reason Eastern Europe seems to be full of developers with great attitudes who are meticulous about their work. One friend theorized that the old USSR used to have a great math education program and this has created a very logical culture in ex-soviet countries. Go figure!

Beware of firms from India who promise the moon and tell you they can get the work done very quickly. I have nothing against Indians, but it seems like the word got out in India that you can swindle lots of American companies by promising big and filling projects with people who barely code. Most of my friends who have outsourced development to India have seen their projects end in tears.

3. Outsource front-end but not back-end

Building software is fundamentally about communication. Communicating what to develop is pretty difficult and normally requires specifications, walkthroughs, lots of discussions and iterations until things are just right. Because of the communication cost, I have avoided outsourcing back-end work as the amount of communication required to get it right is usually very high.

I’ve found it much easier to outsource front end development work since the PSD provides a very clear picture of the expected end product.

4. Pay hourly but ballpark

Freelancers typically like to be paid by the hour since it provides assurances that if the scope changes, the freelancer will be fairly compensated. I therefore am fine with hourly rates, but am sure for each task which is assigned to the freelancer to ballpark the time allotted to it before any work is done.

Ball parking/estimating the time for each task is important since you’ll be the one paying for it if it goes overtime, but it also helps to clarify assumptions which may naturally be lost in communication.

5. Use tools to track time

Since I pay by the hour, I like to use all means to ensure that I am paying only for the work that’s being done. If the freelancer is on the clock, but they are playing Solitaire, I want to be sure I’m not paying for it.

This is why I require all freelancers working for me to track their desktop using freelancer time tracking tools which take screenshots of their desktop as they work. Luckily, oDesk provides this automatically.

I find that capturing a desktop results in every freelancer actually logging fewer hours than exist in any working day, since they don’t expect you to pay for hours they spend surfing the internet. It results in getting billed for just 4 hours out of an 8 hour work day.

6. Look to the Philippines, the US or Canada for assistants

I have had the best results working with Virtual Assistants who are located in the Philippines, the US, or in Canada.

Many Filipinos speak fluent English, have a great work ethic, are University educated and are looking for virtual work.  Several have also told me that making $5/hr is a lucrative salary in the Philippines! This makes them ideal for the type of administrative work that I despise but is necessary like internet research and posting to social media sites.

For more involved work, I suggest hiring a VA located in North America. While their rate will be higher than those overseas, I find that work from home mothers or college students can provide reasonable rates and are very happy for the work.

7. Make your project stand out

oDesk and other outsourcing sites are filled with projects which sound scummy – projects like “Write a 100 page eBook from these 5 Wikipedia entries.” So I highly recommend that you make your project stand out by selling the perks of the position and the importance of the work.

Freelancers, like every other employee, want to work on interesting projects which actually are contributing to moving society forward.  So if your project is interesting, please do sell it! You will get more applications overall and the ones that you do will tend to come from better quality candidates. If you sell it well enough, you might even get people who volunteer to work for you for free!

8. Be good to your people

While it’s just good karma to treat your employees well, there are other perks that come with keeping your people happy. Your people are more likely to do good work, charge lower rates and take your follow-up projects if they like you. Word gets out about how to treat your employees – especially when a rating system, like on oDesk, is in place.

To harness the relationship, I suggest investing the time to get to know the freelancer and their goals at the onset of the relationship. Be reasonable about expectations and if there is a way for you to give them work that will help with their goals, by all means do it.

9. Fire Fast:

Freelancers, like every employee, need to be set up for success and managed with clearly defined expectations and deadlines.

That said, I have found that if a freelancer misses a deadline or falls short of your expectations in an early task, it is usually an indicator that they’ll continue to be troubling to work with on down the line. Low performing employees can soak up a lot of your time when they miss deadlines and cause a lot of back and forth when details come out sub-par.

When somebody is consistently not performing to your level of expectations, it’s a good idea to let them go sooner rather than later.

Final Thoughts

If you can find the right people, I think you’ll be surprised at just how affordable it can be to have freelancers work for you. Heck, if you can hire the right people and create the right system – you REALLY can sit on a beach while you make money.

Personally, I’m just happy with freeing up some time to focus on other important things.

If you have any additional tips for working with freelancers, please do share them to the comments.

I’m confused.

I am a huge fan of learning new things. I feel that in this ever changing world, the person who learns the fastest is going to be the one ahead at the end of the day.

So I was extremely excited to observe the explosion of online learning startups. With these online choices, I no longer had to sneak into my local universities and sit awkwardly with 18 year olds to learn about the wonders of Greek mythology, but I could just stumble over to Coursera and hunker down for an hour to get my fix.

There’s one big problem: a recent study showed that 90% of students who start any online only class, drop out before the end of the class. While I initially thought that this was isolated to free courses online, traditional universities that offer online courses have experienced a similar dropout trend as well.

Do we just lack discipline?

I myself have been no better at taking my online classes, despite signing up for Steve Blank’s course on building startups. It took six months for me to work my way through it. While I have gotten an immense amount of value out of it, I could never dedicate myself to watching the videos.

Traditional learning environments know that we lack discipline and force exams, quizzes and essays on us to verify that we are actually learning things.  As a society though, isn’t it a little sad that we need these re-enforcements because we just can’t discipline ourselves to learn something for our own sake?

Perhaps overall we just can’t get ourselves to do what would be good for us. Apparently 70% of gym signups over-estimate how many times they will go to the gym and really, who keeps their New Year’s resolutions?

Can We Hack Ourselves to Learn?

Interestingly enough, Columbia University’s Community College Research Center found that “students in hybrid classes — those that blended online instruction with a face-to-face component performed as well academically as those in traditional classes.”

Perhaps seeing people on a regular basis serves as another level of accountability and naturally creates a sense of commitment to each other. I experienced this myself when a group of my friends all decided to take the Gamification course on Coursera. When together, it was natural to ask each other if we had done the assignments or watched the other lectures. Saying “oops, nope” shamed us enough to do the other required work on our own.

For online education to provide a societal change, we need to start thinking about what we can do to get people to learn en masse. I’m pretty confident that somebody will come along that will determine a way to hack the social/psychological dynamics to get people really engaged and ultimately get online learning to cross the chasm. Here’s hoping…

Embrace Upsetting People

February 6, 2013 — 2 Comments

I’ve learned that you need to be ok with upsetting people from time to time to if you are going to attempt to lead a movement.

On Friday, I accidentally published a blog post, which discusses absurd paintings which have sold for over a million dollars on the Art Sumo blog. Although, I share a view that the art which caters to the rich is somewhat odd, I felt that the post could make me look silly and I did not want to ruffle too many feathers when launching artsumo.com, so I decided not to publish it.

Since publishing it, the post has gone on to make the digg homepage and garner the most traffic that artsumo has ever seen: about 50,000 visitors in the last 4 days, with over 500 shares between Facebook and Twitter.

I’ve found it particularly interesting that different discussion forums have very different takes on it.  Some can’t find enough 4 letter words for me (I got an email that started with “whoever wrote this article is an artless cunt”), while other forums completely agree with the spirit of the article.

I witnessed the same experience when I published a post sharing my view that entrepreneurs shouldn’t get an MBA. Half loved it, it half loudly expressed their displeasure.

These experiences have taught me that any discussion which challenges the status quo will give a voice to a certain group of people, but will probably piss off a lot of people who don’t share your world view as well.  While it would be nice to get the former without the latter, I don’t think it is possible. So, from now on, I’m going to be embrace ruffling a few feathers.

Blogging title photoI am approximately 2 months into blogging and I thought I’d share some surprises that I have learned along the way. Below are the top five surprises I’ve learned in the past couple of months.  In short I am sold on the value of blogging.

Surprise #1: The Best Blog Posts are the Easiest to Write

While few of us are the CEOs of large companies or the thought leader in our niche, we all have subjects that we investigate deeply from time to time. I am learning that:

  1. I am able to produce my best blog posts on the subjects which I have recently researched, learned or discussed.
  2. When a topic is fresh, blog posts discussing that topic are actually the easiest ones to produce. If a blog post is too hard to write, I probably don’t have anything personally interesting to share.
  3. Writing the posts allows me to solidify my own understanding of the topic.

Surprise #2: Nobody Likes Criticism In Blog Posts

The Internet has provided everyone with a megaphone. Two months ago, I didn’t really understand that even constructive criticism, when given online, comes across as somebody shouting at you in the loudest possible way.

I learned this lesson through a post discussing some suggestions for improving Start-up Weekend. I typed it after attending a Start-Up weekend and leaving the weekend exhausted and confused about the experience. Blogging on some suggestions was both a nice way for me to vent and to solidify my thoughts on the subject, while providing some suggestions to the weekend organizers.

Boy was I wrong. Unfortunately, the suggestions came off as public criticism and it wasn’t greatly appreciated by the start-up weekend team, who I hold in high regard. If I really wanted to help, I should have just sent them an email. I think it would have been much more positively received. Sorry guys!

Surprise #3: Controversy Breeds Traffic

I published a post called “Hey Entrepreneur – Please Don’t Get an MBA” on October 11th. While I knew it was controversial, I also thought that it was honest. The subject clearly resonated with some people as it reached #3 on the Hacker News homepage and became #1 on the entrepreneur sub-reddit. It also sparked a whole slew of comments all over the web and a rebuttal blog post by Mike Gozzo, which got picked up by Venturebeat. Needless to say, the post caused a huge spike in traffic.

People were very passionate about the subject and they clearly sit on either side of the fence. It’s fascinating to me that while my blog post was filled with comments telling that I’m wrong, the rebuttal post is also filled with comments telling him he’s wrong.

It seems that if you should expect some amount of criticism for saying anything controversial online. Further, controversy is very tempting since it has the potential to drive so much traffic.

Surprise #4: Posts Which Discuss Your Start-up Convert The Best

I’ve found that posts which mention concepts around which Art Sumo are based or things that I’ve learned from Art Sumo produce the number of conversions. Specifically, the two posts which directly mentioned Art Sumo drew many more signups than the MBA  article, even though the drew significantly less traffic.

While the MBA post drove quite a bit of traffic to my personal blog, almost none of it resulted in signups on Art Sumo. While signups on Art Sumo were not my goal in blogging, they sure are nice.

Recent Traffic

This is how blog traffic has looked over the past 2 months. The spikes correspond to posts.

Signups on Art Sumo

This is a graph of signups on Art Sumo,  Note the largest spikes correspond to posts which mentioned Art Sumo

Surprise #5: You Will Be Ripped Off!

I spent a good while writing a blog post discussing The Rise of Curation. It probably took me approximately 10 hours to produce. It was validating to see it reach the top spot on the Entrepreneur subreddit.

I was surprised to wake up the next day to see that the post had been translated into Mandarin and posted to five different Chinese blogs. What’s incredible is that they actually changed some of the images and switched out the video and inserted their own.  I slowly starting seeing that Art Sumo was getting signups from China!  While they removed most mentions to naysawn.com, they left in the links to Art Sumo, since those links were crucial to the content.

I have since learned that any popular internet blog is scraped, translated and re-published. It seems many people have realized that a good business strategy is just to localize content which other people are producing. There’s really very little you can do about it. Perhaps it is a sign of progress, if you’re being ripped off, at least people think your content is good enough to be posted somewhere else!

What has surprised you about your blogging efforts?  I would great appreciate learning anything you have found interesting along the way. 

Thanks Sean for the cover photo.

I’ve had an interesting two years bouncing around the world while building Art Sumo. While I initially left Microsoft with a plan to build a company where the cost of living was lower, I’ve decided that it is worth the higher cost of living to live in a startup hub. Below, I will share with you my story and lead you through my reasons of why I have changed my thinking.

Leaving Seattle

When I left Microsoft, I initially thought that internet entrepreneurs should live where the cost of living is best. To create a good internet company, don’t you just need a good internet connection? If you just need a good internet connection, wouldn’t it be better to live in some of the places best known for their quality of life?

Prior to moving to Seattle, I had lived in Montreal, where it is actually hard to walk down the street without bumping into something fun to do. It was no surprise that once I had the golden handcuffs removed, I set out to hop around the world finding fun spots to live, far away from Seattle – which is hardly known for its nightlife (no offense west coast lovers!). while building a company,

So – for the past two years I have lived, for at least 2 months at a time, in places which could be considered anything but startup hubs. They are all places where the quality of life is really good and the startup community is next to non-existent. Specifically the journey has been from Seattle -> Istanbul, Turkey -> Granada, Spain -> Montreal, Canada -> Anloga, Ghana -> Berlin, Germany -> Seattle, Wa -> Santiago, Chile -> Seattle. I’ll mention a few highlights below.

Granada, Spain

Granada Skyline

Granada Skyline

My girlfriend, Lindsey, and I spent 2 months living in Granada, Spain.

A few friends had told me that Granada was one of the cheapest places to live in Spain. They sure were right that the cost of living in Granada is very low, so low that you can have a meal for 2 euros! A fully furnished 2 bedroom apartment, in the center of Granda cost 500 euros a month. Tim Ferris is right: you can live in some of the coolest places in the world for very cheap. In addition, everyone we met was extremely nice and very interested in us. In fact, Lindsey and I probably made more friends in a single week in Granada than in an entire year in Seattle.

That said, after a couple of weeks, I started to understand why the cost of living is so low – almost no one works in Granada. The unemployment rate in Spain for those under 25 is currently at 50%. Therefore, you can find students or elderly people in Granada, but next to no working professionals. Unemployment is so common that many people ask if you work rather than what you do. Since most are unemployed, our new friends had plenty of time to hang out, go to the beach, go dancing and introduce us to all the best tapas places in town.

We, however, found it very challenging to relate to almost anyone on a professional level. While we were able to find great internet connections in Granada, it didn’t seem to me that internet thinking had crept into the public psyche in Spain. Whenever I explained to people that I had an internet business, they were very surprised to learn that you could make a living online. While I encouraged those with degrees in Computer Science to apply their skills via freelancing and building websites, they preferred to study for a year to take a test which would give them the opportunity of having the government pay for them to teach computer science to others.

While we had a great time, professionally we advanced very little by being in Granada.

Montreal, Canada

Montreal Streets

On the streets of Montreal, with Safa and Nika

I spent 3 months living in Montreal next, trying to take Art Sumo to the next level. I always had fond memories of Montreal from college and had been going back every summer. It’s hard not to enjoy life in Montreal in the summer. Festivals abound and just by walking up the street, I found myself always running into things to do.

I became pretty immersed in the small startup scene that exists in Montreal. This included attending the Startup festival, hanging out at Notman house, and hitting up the startup events in town. I learned that there are crazy government incentives for running a small business in Canada. In fact, almost every entrepreneur I spoke with mentioned that in some way, shape or form, they had received some government assistance for running their companies. While this sounds like a good thing, it actually allows Canadian startups to be less ambitious, since to make the same amount of money as their American counterparts, they need to earn less.

There certainly are the beginnings of a startup ecosystem in Montreal, complete with incubators, conferences, government support, and a small venture capital community. I was pretty impressed with it and blogged about the perks of bootstrapping in Montreal. I may still come back some day, because I do love the city.

Anloga, Ghana

Naysawn in Ghana

Me in Ghana with Elvis and Vegas

After 3 months in Montreal, I jumped on a plane to Ghana, which is located in Western Africa. My girlfriend, Lindsey, had been leading a micro-finance team handing out loans in rural Africa and it seemed like a good opportunity to interact with artists, hang out with her, and see Africa for the first time. I had the hope that I’d be able to iterate on the site from a 3G internet connection.

While Ghana proved to be a fantastic place to get art and meet artists, I quickly learned that it was not the right place to be running an internet company. While many say that Ghana is one of the most developed countries in Africa, I began to appreciate the niceties that we take for granted in the first world that enable business people to be productive. In Africa, such niceties as electricity or a stable internet connection were not things I was able to rely on. The power would go out for days at a time and the internet would routinely go out without much explanation.

Ghana was amazing for other reasons, including the opportunity to meet artists and hear their stories as it is overflowing with artistic talent.  It was however pretty hard to do anything online let alone grow an internet business.

Santiago, Chile

Start-up Chile

Some of the Start-up Chile Crew

In Ghana I received notice that I was accepted in Startup Chile. The offer of Startup Chile was pretty compelling: 40K worth of business expenses to live in Chile among hundeds of other international entrepreneurs. It was too compelling to turn down, so I packed up my bags and arrived in Chile in the middle of January.

I found Santiago to be pretty awesome but still probably not the best place to be running an internet company. Start-up Chile was a great experience. Being in SUP provided a community of entrepreneurs, a co-working space, a network, and a friend pool from day one. However, it did lack a few key elements that the Start-up Chile program itself is trying to solve by paying entrepreneurs to relocate to Chile. These include: 1 – an actual tech sector with big companies and numerous programmers and, 2 – a community of mentors that can help you get to the next level.

In Chile, I also began to realize that it feels a little odd living in a place building a product to be used in another location. I found that meeting with customers, advisors, investors or colleagues to be so much harder when they occur over Skype and that people just did not feel the same desire to help me out when I wasn’t physically near them. The start-up community in Startup Chile filled some gaps, but I struggled finding mentors within the internet professional community who could help me learn in all the subjects which I wanted to master. I started to understand why the government feels the need to pay entrepreneurs to come to Chile since there really is a cost for not being somewhere where internet entrepreneurship is cool, practiced and established.

Back in Seattle

Therefore, after a year and a half of moving around the world, I am very happy to be back in Seattle and I plan to stay put for the next year or two. While Seattle is not Sillicon Valley, it contains all the elements of a vibrant start-up ecosystem.

After living in many locations where I have felt like an extreme outlier, I’ve realized that you are doing yourself a disservice by living in a location where you are not surrounded by like minded peers. Without peers, who can will you learn from? Who will question your current strategy? Who will push you to the next level? Jim Rohn says that we are the average of the five people you hang out with the most. If you live in a place with a great startup ecosystem, odds are that those five people will be pretty accomplished. This will naturally teach you new things and cause you to up your game.

Do you agree that it makes sense to live in a Startup Hub?  Please share your thoughts in the comments. 

ps. This blog post started as a comment on Joel Gascoigne’s blog.  He’s a great read, check him out!


The Magic of Providing Less

November 1, 2012 — 5 Comments

I’ve noticed a trend among Internet startups: while some continue to focus on providing an endless amount of choice, many have determined that they can compete by providing fewer, well-thought out choices. My company, Art Sumo, clearly took this approach and it’s been working pretty well for us. Below I offer a few reasons why we decided to offer less, and outline the strategy of curation by looking at a couple of other startups who are succeeding by providing fewer options as well.

Why would fewer be better?

In The Paradox of Choice: Why More Is Less, American psychologist Barry Schwartz reasoned that a certain anxiety sets in when consumers are confronted with too many choices. Rather than feel empowered by the number of choices at their disposal, consumers often feel paralyzed by them as they feel they need to research all the options available in order to make a decision.

Further, in his TED Talk, Schwartz describes a recent experience purchasing a pair of jeans. When Schwartz summoned a sales person for assistance, rather than just being asked his dimensions, the salesperson asked: “Would you like bootcut or straight cut, acid wash or clean wash, worker or casual, etc.?” Feeling overwhelmed by the experience and not as happy about the jeans he finally bought, Schwartz decided to investigate the issue thoroughly by writing a book. Schwartz concluded that, although in the end he actually purchased an objectively better pair of jeans than he could have purchased in the 80s, when there were fewer options, he wasn’t as happy with his decision. This is his TED talk:

While we assume that more choices allows us to customize exactly what we want, in cases where we don’t really know what we want, sometimes choice can be more of a burden than a help.

Art Sumo

When I was starting out with Art Sumo, I had a vested interest in providing fewer options and trying to get away with it. More options meant more inventory, more artists to deal with, and a much larger risk with an idea that was still unproven.

Art Sumo

The Art Sumo homepage

So to start out, with Groupon on the rise, we decided to focus on offering less options but providing them in a curated manner. Our strategy would be to send out a single painting a day to our customer base and make it available for sale. My hope was that people would stay subscribed to keep looking at interesting art on a daily basis and, if they ever loved a painting, they would feel an urgency to buy it.

After launching, many gallery owners told us that the experience matches more closely with how people actually look at art in a gallery. Most art aficionados generally examine paintings one by one before falling in love with any single one; if they do decide they like one, they might ask themselves if it matches their interior. It is pretty rare to walk into a gallery and say something like “I need a painting, between 20-30 inches wide with a white exterior, inspired by Van Gogh,” like some art sites facilitate.

While we are gaining traction we are sticking with this strategy since it is working. Art, when it is presented in this manner, sells when it has not sold when presented in other channels.


Filling an online marketplace is tough in any niche. It’s particularly challenging in online dating where there are many more men than women looking for dates, everyone wants to date the same people and people only want to date until they end up in a relationship.


The Grouper Homepage

Observing these challenges, Grouper decided to curate the dating experience. Rather than providing a searchable, online database, like typical online dating sites, Grouper uses the information contained on your Facebook profile to pair you up on a blind date with one person of the opposite sex that best matches you. To ease the pressure, increase the odds of a good match, and make it feel less like “blind dating,” they ask both the guy and the girl to bring two friends each to the bar.

I love the idea since not only is it a more natural way and fun way to date, it’s also a great business strategy! By curating the experience and pairing up just two people they need remarkably fewer people in their database to be of service. In fact, Grouper just needs two people in a single locale to provide their users with value.

Jack Threads

The story of Jason Ross and Jack Threads is pretty awesome. Jason thought that there should be a market for designer men’s clothing at a discount. To test interest without investing too much in inventory, Jason created a site which provided a deal a day service of fashionable item a day. Users could purchase only the item shown on the site each day. Since the deals were so good, users signed up in the thousands.


The current Jackthreads homepage

With the market proven, Jason hustled conferences, got exposure on many blogs, and managed to build an email list of 350,000 members in a single year!  With many more members, Jason changed the site to a flash sale, similar to Gilt, so as to provide an impetus to buy urgently, but providing more options to his large list of members.

How To Scale

While curation is great for all the reasons stated above, it does have a big glaring problem: Scale! While people may enjoy fewer options, this means that there are fewer opportunities to sell. And fewer opportunities to sell means it is harder to make money.

Therefore, while Jack Threads, Woot, and Groupon all started out with the model of providing a single item a day and fewer choices, once their lists become large enough, they started expanding and providing more options to customers. While this might seem like it is counter-productive to the whole curated experience, all these sites have done it in an intelligent way which I don’t believe has harmed their curated offering. Groupon, for example, still provides one custom local deal in your inbox each day. However, right next to their promoted deal of the day, they offer other options for you as well. This has allowed Groupon to scale all the way to an IPO.

Do you agree with the strategy of providing fewer options early on? Please share your thoughts in the comments or on hackernews.


I recently hit the Hacker News homepage for a post which discussed my favorite startups from Start-up Chile, it was on the homepage for a couple of hours.  I’ll break down how useful this traffic was below because to my surprise, while the post generated over 3700 visitors, only 10% of them viewed more than 1 page.

The Traffic

The spike from Hacker News sent in about 3700 visitors with the following breakdown:

It also generated:

  • 43 Tweets
  • 33 Likes, 14 Comments and 13 Shares on Facebook
  • 52 upvotes on Hackernews
  • 30 upvotes on Reddit
  • 60 signups on Art Sumo (a nice spike)
This is the traffic to naysawn.com by hour:
Total Visitors by hour

Total visitors by hour

BUT Only 10% of Visitors Viewed More Than 1 Page

While the post generated a lot of traffic, 90% of the visitors bounced.

Here is the engagement breakdown from Google Analytics:

Engagement Numbers

Google Analytics Reports That 90% Left Within 10s

Edit: After publishing this article, Fred correctly pointed out that Google Analytics reports users spent 0 seconds on the page if they leave within a single page view.  Therefore this graph above is deceptive.  All that it shows is that 90% of users left the site within viewing a single page.

Engagement Differed Widely By Source

While Hacker News and Reddit sent the most traffic in terms of the percentage of the total traffic they sent, each was also more likely to have users only view a single page on the siter. I suspect this may be because people generally are opening less links when browsing Facebook and Twitter than when they are browsing Reddit or Hacker News.

  • Reddit: 6.7% viewed more than 1 page
  • Hacker News: 8.6% viewed more than 1 page
  • Twitter: 11.7% viewed more than 1 page
  • Facebook: 25.7% viewed more than 1 page

Hacker News and Reddit nonetheless dwarfed Facebook and Twitter in the raw counts of users who viewed more than 1 page.

Over 10 seconds Breakdown

Reddit and Hacker News still sent the most users who viewed more than 1 page

Useful but Not Incredible

Although only 6.7% of Reddit users and 8.6% of Hacker News read more than one page, they were still a great bunch. Many found the content compelling enough to sign up on the various start-ups, which were mentioned in the post, tweet it out or sign up on Art Sumo. This all came from just 300 visitors out of more than 3000 who first landed on the site.

Do these percentages match your own experience?  Please leave a comment or join the discussion below on hacker news.

Some prospective MBAs

Some prospective MBAs

It seems that every time I am at a crossroad in my life, I contemplate getting an MBA.

In my head it sounds something like this: “By joining an MBA program you can quit your job to hang out with other smart and ambitious people. You will get to put your life on hold, your parents and friends will respect your decision, and you’ll be able to pretend that you’re taking a step in the direction of starting a company.”

You can probably guess that I have ultimately decided against getting one. I think you should decide against it too – if you would be getting one primarily as a first step to starting a business . My reasons are as follow:

1. What You Actually Learn

While MBA programs do contain courses in leadership, negotiation, and case studies which will no doubt prove useful post graduation, much of the actual content of the program focus on corporate skills and how to network to get a job. While useful for Fortune 500 companies, I question how vital they are to web-based start-ups?  Even if they will be useful down the road, how useful will they be when just starting out?  If they will be useful down the road, will you recall the material when the time arises?

For a web-based start-up, I personally would find it more useful to learn the ins and outs of topics such as customer acquisition, viral loops, search engine optimization, web development, customer development, UX design, and strategies to reach hard to reach people. While some of these may be included in an MBA program, they clearly are not the focus.

Furthermore, for a person who is motivated to teach themselves, many of these topics can be found online for free. The number of online video course platforms is exploding with a new one being announced every day.  You can use materials on LyndaTree HouseUdemy and Creative Live for technical knowledge while taking free University coursers on CourseraUdacity and EdX for the theoretical knowledge. Steve Blank is even currently teaching a free course on how to build a startup on Udacity!

2. Tuition Costs

Excluding cost of living, tuition from a top-five business school is easily over $100,000. While you could go to a cheaper school, I really believe that going to anything that isn’t in the top 10 somewhat defeats the whole purpose of going to a business school – to building a network and a good stamp on your resume.

Bootstrapping a start-up is actually dramatically cheaper. The highest cost in most internet-based start-ups is salaries of the team, so long as you are willing to downsize your lifestyle, you can live on your savings while you and your co-founders are creating the company and not drawing a salary..

The cost of an MBA was a huge hindrance to me and I was extremely wary of the consequences of graduating in debt. I felt that the biggest asset I possessed was the ability to bootstrap a business, while not taking on capital until the idea was proven.

3. Time Commitment

While most MBA programs last two years, after shelling out $150,000 to receive a degree, wouldn’t it be tempting to sign with a company who would pick up a good portion of the bill for you? I recently learned that  graduates in the top programs are frequently offered signing bonus from their first post-degree employer, who pays for a good portion of the cost of the degree. However, these signing bonuses come with the condition that you commit to stay at the company for at least a year or two. If you accept such an offer, the timeline to getting an MBA starts to look more like a four year commitment than two.

I personally felt that if I were to sign with a company after an MBA program, it would not be particularly easy to leave a steady paycheck behind in order to start my own company.  Four years after the degree, I would likely have other financial obligations tying me down (i.e. mortgages, family, car) that would make it more difficult to take the leap.

4. The Wrong Network

MBA alumni often cite their network and connections are the most important perks from the program. Many say that if they ever needed to find a job, a simple phone call is all it takes to get an interview. While this is great if you want an interview, how useful with a network of mid-level executives at Fortune 500 Companies like Sony, Yoplait, Amazon, Microsoft be to a bootstrapped entrepreneur?

I question the network’s ability to get you to the next level.  I would rather have a network of like minded entrepreneurs who are a step or two ahead which would help me reach the next level – ie a network from YCombinator alumni, rather than Harvard MBA alumni. I have also found that entrepreneurs really respect other entrepreneurs are happy to open doors once you are already have started a company.

5. Few MBA’s Start Businesses

Despite everything learned about business in MBA programs only 5% of graduates go on to start a business upon graduation!

Perhaps these are some of the reasons: 1 – Most of other graduates are going to be going to 100K+ paying jobs, 2 – the tuition from the program will land most in debt and 3 – by ones early 30s, most need to draw a salary to support your life style and family.

My Suggestion:

If you are currently debating getting an MBA, a vacation or a start-up – I would highly suggest taking a vacation + seeing how you feel about it. Every time I have contemplated entering an MBA program, I have always arrived to the conclusion that I was ultimately interested in a vacation that looked respectable on my resume.  If any of this ring true for you, I would encourage to give entrepreneurship a shot and define your own path through life rather than one, which some institution has crafted up into a nice and socially acceptable package.

I’m sure not everyone will agree with these conclusions. If you disagree, please do tell me why I’m wrong in the comments or in the comments on Hacker News.