In the past three years, I’ve put countless hours into The Art of Ass-Kicking. It’s been a lot of work, but also tremendously rewarding, both personally and professionally. More than a hobby, this blog has become an integral part of my life. I write to internalize what I’ve learned, and to share with with you, my readers.

In the early spring of 2013, I was thinking about where I could take the blog next, and after a conversation with Kai Davis, decided to publish a book that represented by best ideas, stories and strategies.

Over the course of many months, I put together a book that spans three major themes: focusing our Minds, strengthening our Bodies, and increasing the impact of our Work. I edited and rewrote thirty-one essays (representing over 50k words), designed a cover and three pieces of original quote typography, recruited Sebastian Marshall to write a foreword, and navigated the Amazon Kindle Publishing program.

Today, I’m thrilled to announce that my book is now available for download on Amazon as a Kindle ebook.
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My book is currently being edited for a V2 release
Note: through October 22nd, there’s also a special giveaway related to the book launch. Scroll down to learn more. Continue reading

One lesson I’ve learned is that launching always takes longer than you think. If I got paid every time I heard a founder say their product was “two to three weeks away from launch” I could start angel investing.

Case in point: it’s been over a month since I said I was almost done with my cool YC-related project.

Well, better late than never is my motto. Last week I put up what I called the Unofficial Guidebook for Y Combinator Applicants at In it, I shared everything I’ve learned from applying to Y Combinator, getting in, going through the program, understanding more about how the YC partners think and connecting with other founders.

I had friends who were applying to Y Combinator and asked for my advice so I would review their application. But I felt like most of my best advice was about how think about applying rather than specific feedback on their application. I wrote up a Google Doc on my thoughts on each section (team, idea, distribution, video, etc) and over the past few months have fleshed it out to what it is now – a 20,000 word guide on every aspect of the YC application process.

I put it up on Hacker News and in 24 hours got 6,500+ unique visitors spending over three-and-a-half minutes per visit. It was really great to know that people were digging my stuff.

After that, I worked closely with the awesome team at Hyperink, (a YC company that’s transforming publishing) and we were able to put together a beautifully laid out and carefully edited 92 page document that’s available as a free PDF download and also in mobi and epub versions in just 10 days.

It took longer than I expected – because I went through and re-edited several sections to make it as clear and readable as possible. I also integrated feedback from various YC partners who commented on the content. The Hyperink team did an amazing job turning things around quickly and professionally.

The result is something I’m proud to share with you.

Get your free copy of Guide to YC here.

I hope you enjoy the guide and I’d love to hear any feedback you have on the book. Please rest assured: regular blog posting will resume shortly.

Photo credit by Nils Öhman

There’s only a week left in November so it’s a little late for doing a NaNoWriMo post but I figure better late than never…

For those of you who aren’t familiar with the awesomeness that is National Novel Writing Month, it’s exactly what it sounds like – people from across the US (and now abroad) get together and collectively write a novel. It’s a great experience and I highly recommend it. (So does Lifehacker!)

For those of you going through it now, here’s an email I wrote to a family friend (middle school student) looking for advice on her first NaNoWriMo. Might be just what you need to get across the finish line. Keep writing!

NaNoWriMo Poster

Hey Family-Friend’s-Name,

Thanks for reaching out! It’s great to hear that you are doing Nanowrimo. I tried and failed to do it in 2006 (got to 35,000 words) and tried again in 2009 and was able to do it successfully.

The hardest part for me wasn’t finding the time to write, it was coming up with enough words to actually get to 50,000.

1) Give your story a lot of twists and turns.

I’m not someone who likes to do a lot of description. I’m a dialog and action kind of writer so I really needed a lot of side plots to the keep things going.

A piece of advice I often hear about fiction writing is to make sure your main character is always has a goal in mind and keep throwing obstacles at him/her that they have to overcome. Don’t make it easy for your character to get what they want!

2) Write what you know

My first novel was a modern sci-fi thriller which I found interesting but there was too much I didn’t know to write a good book. For example – if you are a regular person, what’s a reasonably realistic way for you to get a bunch of weapons on the black market? I’ve never done this and would have to spend a lot of time researching it on the internet. I had a lot of questions like this in my first novel and this slowed me down. You gotta keep pumping out words!

My successful novel was a fantasy novel. This worked a lot better because I read a lot of fantasy growing up and you really do get to just make things up as you go a long since it’s your book and your world, things can work however you want (with regards to magic, dragons, trolls, etc)

If you read a lot of a certain type of book, it’ll be easier to write a book in that style. Also it’d probably be a bit easier to have a main character close to your age or younger, than to write about someone who is 50 or 60, since it’s harder to understand what kind of stuff they deal with / think about.

3) Go off on tangents.

This is similar to lesson number one, but more specific. I think I had a couple sections of the book that were totally random. Sometimes I got really into describing something – like the history of an ancient tribe of elves. Almost like a story within a story.

But you can get even more random. I think in one part of my novel some random character starts talking and all of a sudden its a list of stuff I have to for work or a journal entry about how I’m feeling about living in San Francisco. Totally random, doesn’t make any sense.

But again, it’s your book and you’re allowed to do that if you want.

4) Write consistently.

Its 1667 words a day. That’s a good amount, but not crazy. I wrote basically on my train to work, my lunch break and my train home, plus spent time at night and on weekends writing. You will have to spend a lot of time writing, ideally with a keyboard instead of by hand, to get this book done. It’s a lot easier of you just do 1667 a day and not have to play catchup. That’s really demoralizing. So write everyday!

I hope this wasn’t too long and was helpful. Let me know if you have any other questions.


It’s good to celebrate milestones so here’s one: I passed one full year of “real” blogging in August. (I realize it’s now September but better late than not at all!)

My first post was called “Things I’ve Learned in 3 Weeks at a Startup“. I had just started at isocket and I can still remember how excited I was to soak up all this new knowledge about marketing, board meetings, customer support and user testing.

Blogging was a great way for me to share what I was learning, retain the knowledge and build up a brand/network in the startup community. One year later it’s amazing to see where the blog has taken me. It’s made me smarter, happier and more lucky.

I promise that this blog is NOT going to become a blog about blogging – that would be both annoyingly meta and really uninteresting. But still – a man must discuss his craft from time to time and this is the place to do it. I’ve tried to take my own advice (particularly #4, #6 and #9) here as well. So anyway – here are 9 lessons I’ve learned from the past year of blogging:

1] Consistency matters

From August 2010 through July 2011 I put down over 140 posts, which is one every 2.6 days. My worst month was October 2010 (6 posts) and I was most prolific in April 2011 (17 posts). I believe a big part of my blog’s success has just been posting on a regular basis – it’s not easy but it’s worth it.

2] Be flexible about what counts as a post

If someone told me a year ago that I’d need to publish a blog post every few days for a year, I’d be pretty intimidated. “Where the hell am I going to find the time / material to put out so much content?” is what I’d be thinking. But not every blog post has to be a huge 21-item list or an epic, 3-part personal journey. I’ve posted dozens of quotes and videos – and a handful of podcasts, link roundups and interviews as well. Being flexible about your posts will help you keep your rhythm going.

3] Keep multiple posts brewing

There are at least 4 blog post drafts in my WordPress admin. Sometimes you’re in inspiration mode and sometimes you’re in editing/publishing mode. If you have a great idea for a blog, pull up Evernote or Notepad/Textedit and get the core concepts down. If your momentum holds, finish the post. If not, you can save it for later, when you aren’t feeling so inspired, but you can take a nugget of an idea and polish it off.

4] Don’t judge your posts too harshly before posting

Everyone’s got an inner editor/critic. I like to beat mine senseless whenever it tries to make me uncertain about posting. My number 1, number 3 and number 7 posts of all-time (based on pageviews) were posts that I wrote off-the cuff and wasn’t sure if they’d resonate with readers. Apparently they did – and it would have been a shame if I canned them because I judged them too harshly. Like Sebastian Marshall says: you get judged by your best work, not your bad work. So post freely – there’s little downside (as long as you’re writing something obscene or offensive) and big upside.

5] Be easy to get in touch with and responsive

This blog is my home base online. Jason Shen HQ. All of my online accounts point to this site and I’ve made it easy to get a hold of me. I post my personal gmail account on my sidebar and on my about page – none of that contact form nonsense. I think I’ve gotten unwanted email less than a dozen times in the past year. I have, however, gotten lots of very interesting email from readers that has turned into friendships, coaching clients, new roommates, advice/mentorship, job offers and more. I respond to every reader email I get (so far) and I’ve found this approach to be quite valuable.

6] It’s all about your readers

At the end of the day, you get value by providing it. I always try to make my posts actionable and filled with useful information/advice. There are other ways to provide value (humor, shock value, etc) but however you do it, make sure your blog serves your readers.

7] Finding your voice takes time

I’d like to think that blog has developed a strong, original and authentic writing style over time. You can really hear it in certain posts, like Winning Isn’t Normal or Loud. Arrogant. Rebellious. Asian and my post on gymnastics lessons learned on fear. My voice isn’t something I “worked on” but it is something that just happened as I wrote more.

8] Ditto for your audience

“Know your audience” is the advice given to every blogger out there. For a long time I struggled with this – who was I writing for? This requires both work and time on your part. Because I talk to my readers and respond to all my comments I’ve gotten a feel for the kinds of people who check this site out. They’re 18-35 year olds, skewed male, who are interested in pushing themselves personally and professionally. And over time, I’ve been able to tailor my writing to them. Which reminds me – I should probably take this time to do a survey or something just to refine my understanding even further.

9] It’s ok to get personal

This blog isn’t just about startups, personal challenges, psychology and winning. It’s a reflection of who I am. It’s not a complete picture of me: I don’t discuss my relationship with my family, or my weirdly vivid dreams or my favorite iPad games. (Though on second thought, those topics could all potentially make good blog posts if done right). The point here is that it’s ok for you to get a little personal on your blog. Trust your instincts. I ask email subscribers what they want me to write about, and I’ve been surprised by the number of responses that are just “I don’t want to give you suggestions – just write about stuff you’re doing, and stuff you’re interested in.”

So one thing I had sort of meant to do is write about how my experience has been blogging 5 days a week (as I outlined in my post “Writing More”). I plan on doing a full recap after the four weeks eventually but here’s something interesting: a minute-by-minute break down of how I write my blog posts.

I tracked exactly what I was doing in 5 minute increments for two posts and here are results. I was honestly surprised at how long it took me to write each post – but that’s the power of actually measuring what you do, right?

First breakdown:

Step Up and Deliver: What Gymnastics Taught Me About Performing Under Pressure

This was definitely going to be a substantial post, though I didn’t realize how big it would be at the time. It’s funny how taxing an exercise writing can be. You’re not just hitting keys on a keyboard – it’s like doing pushups with your mind. You get tired and need to recharge. The dashed lines delineate different writing “sessions” – sometimes it was the same day sometimes it was a different days.

10 mins – getting bullet points for post in shower
10 mins – rapidly putting down an intro in wordpress
10 mins – listing bullet points in wordpress
20 mins – watching youtube videos of jordan, paul hamm, li xiao peng, jonathon horton looking for clutch performances,
10 mins cleaning intro, organizing bullet points, embedding video
10 mins distraction watching unrelated videos
20 mins – fleshing out the first half of the bullet points
10 mins – fleshing out half of the first bullet point
10 mins – more distractions
20 mins – more fleshing out

10 mins – re-reading, editing, adding picture
20 mins of editing
10 mins – final touches

Total time: 170 mins (2 hrs 50 mins)

Second breakdown:

How Blogging Can Increase Your Luck Surface Area

This post originated as a response to a question posed on an email list – so it has a different profile, which is why I thought it would be a good one to look at. I dashed off the original email quickly and then thought it would make a good post – but of course it would require a bit of touching up. It turned out that I would spend 7x the amount of time it took to write the original email to finish a post.

15 mins – writing email response to question from the list

10 mins – added two 2 paragraphs

5 mins – reread, kill intro
20 mins – write new intro / 1st half
10 mins – reading posts from Lingbo, who I quote
15 mins – writing more
10 mins – getting a picture, formatting it, getting photo credits
10 mins – adding in links to certain sections, formatting changes for quoted sections
25 mins – edits, clarifications, making it tighter, adding more links, scheduling post

Total time: 120 mins (2 hrs)