10 Thing I Learned From Writing My First Book

One of the last things I ever thought I would do in life was to write a book. I don’t consider myself a writer or an author. I’d much rather write code than prose. I’m also an atrocious speller (the post is likely evidence of that). Despite all those things, I actually did write a book and I’m proud to say that it has been read by thousands of people from around the world. It has been almost 2 years since Shopify Empire was released. I recently started working on an updated version. Sitting down to write again flooded my memory and made me reflect on the process of creating the book. Writing Shopify Empire was one of the largest growing experiences of my life. The following is a list of 10 things I learned from writing and publishing my first book. I hope that some of these points help an aspiring author out there.

1 – English is hard (for me)

I regularly make the joke that I’m fluent in many languages, but the ones I’m most comfortable with are ones that machines can understand. Putting my feeling and words on a page can be difficult for me. To be honest I’ve put making this post off for way too long. There is something permanent to published text. Code is fluid and can be (and should be) changed as bugs are found and as requirements change. Taking the time to sit down and write has always been a struggle to overcome. I imagine that this is just an area that I need to continually work on and eventually will find comfort in. Until that time, English is hard.

2 – Organize your thoughts and get to work

Knowing where to start a project is often one of the hardest parts of the project. I was fortunate in the fact that my book had an organic growth path. As SEO Manager for Shopify grew in popularity, so did the support request and questions from customers. Following suggestions from Tim Ferriss, in the Four-hour work week, I created a series of canned email that supported common questions. I then took those canned emails and added more context to them and created a FAQ page for the app. The FAQ page grew into a series of support articles. At some point, I realized that the support articles were becoming less focused on SEO Manager, and more about SEO best practices for the Shopify platform. I eventually realized that I had enough content for a short eBook on the subject. The content was already semi-organized into topics. When I decided to take the plunge and create a book I realized that the content I had written could be used, but not directly plugged in.  

I created a Google doc with the major themes I wanted to touch on, along with concepts I wanted to teach in a chapter. After that, I sorted the chapters and sections into a logic order. Having this outline acted like a master list of things that needed to be written.

3 – Just keep writing

Having the list was helpful but also burdensome to look at – so much work. I approached the writing as I would approach building an app. I broke it down into smaller manageable pieces instead of taking it all on at once. Often times I would randomly pick a subsection to work on – whatever grabbed my attention and was on my mind. Once it was finished I would check it off the list. I wouldn’t worry about the flow between the sections, just focus on the point of getting my ideas down and focused on the subject matter. This lead to a much longer editing process (more on that later), but it granted me the ability to take on a project that would have been insurmountable if I focused on the big picture. When I write an app, I have a motto of “at least one code commit a day”. The constant forward momentum no matter how small is still forward progress and adds up over time.

4 – Use diagrams / examples when you can

During the writing process, I found myself trying to describe concepts that could be best demonstrated with diagrams and charts. At first, when I would come to a point where a chart could be used I would open up photoshop or other tools and start. This pulled me out of the writing process and I would lose my flow. Finally, I started to insert placeholders, like I would in my code when I write apps. Something that tells me to come back and do this later, but for now leave it and keep moving.

I found that screen capture images with callouts to specific buttons and area really gave impact to what I was describing on a page. I went through a few iterations of images during the editing process. Sometimes I went overboard with charts, graphs, and images. Finding the right balance to complement but not overwhelm was key. As they say, “a picture is worth a thousand words”. I would add “when done properly”.

5 – Editing is brutal

I’ve said it before and I stand by it, the editing process for this book was worse than the worse code review I have ever gone through. As covered above, the written English language is not a strong point for me. I will agree that the editing of Shopify Empire made me better, but damn it was hard! To edit, I would print out the book and take a red pen to it. I would read through every page, marking it up as a went. Often times with no computer in sight. I would go to locations with minimal distractions like a quiet park and read and redline. Sometimes I would make notes to myself in the margins. Once I finished the paper edits I would update the digital version and print it out again. The cycle of analog to digital would then restart. I did this 12 times before I felt that I was ready to send it to a real editor.

I searched for editors online but was blown away by the prices. Being 100% bootstrapped, I didn’t have 10 thousand dollars to throw at editing. I started to ask around and see if I knew anyone that could help out. As luck had it, my very good friend Rhian is an excellent writer and had some availability and was willing to take on the project. I had helped Rhian with some Shopify work, so she was familiar with the platform and had also used SEO Manager before. It was a great fit.

After the 12 rounds of edits that I did myself, I thought the final edits would be a quick process. I WAS WRONG. After Rhian’s first pass through the manuscript, I was blown away by how bad my writing skills were. It was so overwhelming that instead of making full book editing passes, the book had to again be broken down into smaller more manageable chunks. In some cases, we went through the book, paragraph by paragraph in the same room.

The most jarring portion of the editing process came when Rhian suggested that I drop an entire chapter from the book. I defended the chapter stating that it had taken me weeks to write and was the more difficult section of the book to articulate. Her response “I can tell, it doesn’t flow with the other portions of the book. It feels forced. It doesn’t add much value to the overall book. It needs to go”. I knew that there was some part of the book that was going to be trimmed down, but 27 consecutive pages, about 12% of the overall book, was something I didn’t expect!

Controlling my ego during the editing process was more difficult than watching the pages get removed. From a logical standpoint I knew that the book would be better for it, but at the same time, it emotionally felt very personal, like my work wasn’t good enough, like I wasn’t good enough. It was a struggle and a true exercise in managing my emotions. Thanks to Tim Ferriss, I had recently been reading some stoic philosophy. I’m sure some of those lessons helped me get through it.

Overall about 25% of the book was cut or drastically altered. This felt like a high number until a realized that this is fairly common in the non-fiction industry. I’m VERY happy with the end result and wouldn’t change a thing. The book and I are both better for it. The editing process went so well that Rhian joined me at venntov as my partner and COO. Talk about a win-win situation!

6 – Shut up and ship – it’s never “done”

Like all passion projects, this book could have gone on forever. I could have written more. It could have been edited more. I could have tested it with more focus groups. I could have done a million things that would have kept the book from going to press. Defining “done” is a difficult thing to do. Without having a finish line to cross there is no end to the race. When it comes to software development I have a motto I live by, “shut up and ship”. Simply but, make it happen. As my good friend JC once told me, “Don’t talk about it, be about it.” It was hard to call it done, but it had to become “real” at some point.

7 – You can outsource the cover art

When I had the book almost finished I started to think about the cover artwork. I’m dangerous with photoshop but I’m no graphic designer. I had budgeted some money to this portion of the project knowing that artwork is usually never cheap. I started to look around online for book cover artists and discovered the world of pre-make book covers. Sure a pre-made book cover might not be as cool as an original design, but when you are on a budget and you aren’t too particular they can be an amazing resource and at under $100, you can’t beat the price. I used a service called “Go On Write. For a small fee, the designer customized the cover with my name book title and tagline. I actually bought 6 covers and did some testing with friends, family and a few close customers. The winning cover became the cover of the book. It was the easiest portion of the book publishing process.

One of the covers that didn’t make it.

8 – Publishing is easy

When I started writing my book, I knew that I wanted to self-publish it. My original plan was to create and sell an eBook so I wouldn’t have to worry about physical inventory. Some of my other projects in the past involved physical inventory and it was always a mess to manage. Once I started to print the book out to manually edit it, I realized that I liked holding the paper in my hand and reading the words off a page. The book took on a different feeling. I know this is a bad comparison but it like knowing you’re going to be a parent, then holding your baby for the first time. I knew that I needed to have the book printed. I again started doing my research into self-publishing and came across Create Space.

Create Space makes the book publishing process easy by allowing you to download a word document template and a cover graphics template. After you have them filled out, you simply upload them into the system and order some books. The book proofs were delivered within a few days. It took a couple rounds of adjusting things to get the book layout just right. I actually redline edited the printed book also once it came, making note of all the little areas that could be changed to present things better in a physical book format. Once it was all done. A few clicks later and I had a case of books on their way to my office.


Create Space is owned by amazon, so they made it very easy to get Shopify Empire onto Amazon.com.

Selling the eBook version on Amazon Kindle and Apple books was also easy. I paid Create Space some money to have the book translated into kindle format and sold on Amazon.com. For Apple, I paid someone on fiverr to translate the book into the format that Apple wanted.

Once the books were on Amazon, Kindle, and Apple books, I opened a Shopify store – https://ShopifyEmpire.com. I used Shopify’s Digital Downloads app to sell PDF versions of the books, and I manually packed and shipped physical book orders from my office.

Overall getting my book into formats that people could consume was fun and somewhat easy to do. When I release a new version of my book, I will most likely follow these same steps.

9 – Books are magic

I’ve written and released dozens of programs and apps over my career. I expected this book release to be similar to an app release – I was dead wrong. I’ve learned that people react very differently to apps and books. These days, everyone uses programs and apps, but there is a disconnect from them. Apps are generally easy to install and use. How they work doesn’t concern most people. For the most part, apps are magical things, written by anonymous geeks who are part of “The Cloud”.

Most people understand what books are, what goes into them, and they understand the struggle of the writing process. Not everyone is a “writer” but most people write all the time – work reports, school work, text messages, emails, blog posts, Facebook posts, etc, so they can better appreciate books.

I can’t count the number of people who congratulated me on writing a book. I watched people connected with the folded pieces of paper in a way that I’ve never seen someone interact with my mobile apps or web projects.

My biggest surprise came when I was @ mentioned in a tweet from Daymon John, the man behind the hit show Shark Tank.

If you have a @Shopify store this is a MUST READ. @JoshHighland #SharkTools – Daymond John

I was also shocked to find that his tweet endorsing my book went to his Twitter, Facebook, and Instagram accounts. The message was sent to over a million people.

Entrepreneurs the world over would kill to be on Shark Tank or positively mentioned by one of the Sharks. To this day I am unsure of the situations that lead to Daymond John publicly endorsing my book. All I know is that I am extremely grateful and blessed that it happened. The other books that he has endorsed have helped shape me into the person I am today. It still blows my mind to see my book alongside Tim Ferriss, Gary Vaynerchuk, Malcolm Gladwell, Eric Ries, and Guy Kawasaki.

Apps may power the world, but BOOKS ARE MAGIC!

10 – Everyone should do it

It’s pretty common for an author to encourage everyone to write a book. I’m not an exception. I think everyone should do it, but do it for the right reasons. I wrote a book to stretch myself and to better help people understand a subject that I’m passionate about. I went into this effort with a budget, knowing that it was most likely going to cost me more than I made. Money wasn’t the motivation for me, neither was notoriety. I had zero expectations. It was a hobby. Not having expectations made the process fun, even though it was tough.

Before you write a book ask yourself these questions:

  • “Why do I want to write a book?”
  • “What am I hope to gain from writing a book?”
  • “Will this book help other people?”

If you can come up with honest answers to these questions, I think you should write a book.

As with many things, writing is a skill and something that I still struggle with, but it hasn’t stopped me and it shouldn’t stop you. LET’S DO THIS!

Becoming an Author – The launch of Shopify Empire

Shopify Empire SEO


Shopify Empire SEO BookWell, I did it. I wrote and released a book. “Shopify Empire” went live a few weeks ago and it’s been a whirlwind sense then.

I’ve written and released dozens of apps over my career. I expected this book release to be similar to an app release – I was wrong. I’ve learned that people react very differently to apps and books.

Almost everyone uses computers and apps everyday, but there is a disconnect from them. Apps are generally easy to install, and use. How they work, most people couldn’t tell you. Most people don’t write code, even less write SaaS products. For the most part, apps are magical things, written by anonymous geeks.

I think that most people understand what books are, what goes into them, and they understand the struggle of the writing process. Not everyone is a “writer” but most people write all the time – work reports, school work, text messages, emails, blog posts, Facebook, etc, so they can better appreciate books.

I’ve never thought of myself as a writer. I have a lot of thought and opinions, but putting them into written form has always been difficult for me. I’ve done a fair amount of public speaking, video, and podcasting, but always avoiding the written form whenever possible. To be completely honest the real magic happened during the editing process. It was basically worse than the worse code review I have even been through, but in the end the book is MUCH better for it, as am I.

Josh Highland book signingOne of my reasons for writing this book was to push myself to grow in a new direction. I think it’s done that in a major way. The process for me was much more difficult than creating an app, and oddly just as satisfying. I might not be the best writer in the world, but I no longer can make excuses to avoid writing and generating content.

I’m very grateful for the outpouring of support I have received. In the few short weeks that the book has been out, I’ve already been a guest on a Shopify podcast, done an #AMA event, and even did some book signing. I’m excited to see what the future holds as Shopify Empire gets into the hands of more people.

You can find Shopfy Empire at

My Goals For 2015


Keeping with tradition, here is the list of goals I have for 2015:

  • Be more mindful (meditate / don’t stress out)
  • Improve my work life balance (spend more quality time with family and friends)
  • Improve my cardio
  • Continue to pay off more debt
  • Launch my book, Shopify Empire
  • Become more involved in the Shopify community
  • Grow my Shopify app user base
  • Move more of my apps on to “the cloud”
  • Develop a platform independent SaaS product
  • Automate and delegate as much as possible
  • Reduce the amount of “Stuff” I have
  • Drive a Tesla Model S (test drive or rent one)
  • Have a conversation with Kevin Rose and Tim Ferriss
  • Sleep more
  • Blog more

2014 Year In Review



For the last few year I list the goals that I would like to achieve for the year. With this post I’d like to take some time and see how many of my 2014 goals I managed to achieve.

Get more involved in Bitcoin and other cryptocurrencies

2014 started off with massive bitcoin hype. I jumped in with both feet and built a bitcoin mining rig, I called it “miner threat”. The price tag for the parts was about $5500. After a few short months, the mining rig was costing more money to operate then we were mining. Overall, mining bitcoins was fun, but not profitable. I can say however that I used bitcoins to pay a ransom to Russian hackers! Grade: #win

Involve more wearable tech in my life

2014 was definitely the year of the wearable and I embraced it. This year I tried the following wearable devices.

Google Glass was the biggest loser of the bunch with few apps, poor battery life and limited usability. Everyone I know who had Glass has ditched it. My favorite wearable was the Misfit Shine. The Shine is a beautiful wearable and I loved wearing it. The down fall of the Shine was the poorly designed wristband that lead to me losing the tracker. I replaced the Shine with the Misfit Flash. The Flash is an extremely cheap version of the Shine, but features an improved wristband. Last week I received my Spire tracker. Spire is worn in the waistband of your pants and tracks your breathing patterns. It detects stress and calmness. I really like the Spire, and I’ll be interested to see the data of my breathing habits. Honorable mention goes to Muse, the brain wave tracker. Muse is very interesting, but hard for me to get into. I like the idea of training myself to live in a calmer state. Moving into 2015, the Misfit Flash, Muse and Spire are the only devices I plan on wearing on a daily basis. Grade: #epicWin

Work on educating people more about MFA and account security

Account security and MFA (multi-factor authentication) has been central to my day job for the last few years. Okta is a cloud identity solution that I help manage at Esri. MFA and MFA education is a key feature of Okta. In November I was honored to be presented with the Okta Atlas Award at the Okta user conference in San Francisco. Grade: #epicWin

Get more involved in the Shopify community

In 2013 I went to the first west coast Shopify meet-up and absolutely loved it. A few months into 2014 a Los Angeles Shopify meet-up group formed. I had the pleasure of  speaking about SEO and my upcoming book at one of the first meetings. You can see my presentation here. Grade: #win

Continue to automate more of my income

With the growth of my apps I was able to automate more of my income in 2014 than ever before. I’m getting closer to that 4-hour work week. Grade: #epicWin

Continue to pay off more debt

I read a great book called “I will teach you to be rich” by Ramit Sethi. It was one of those books that hit me hard. I’ve been following some of his advice and am working my way towards a debt free lifestyle. I’m using more automated tools to make that happen, and it feels great. Grade: #win

Launch another Shopify app

I totally smashed this goal by launching two Shopify apps in 2014 – SEO Scan Pro and Social Share Manager. Grade: #insanelyEpicWin

Continue to delegate more of my tasks

This is something that is really hard for me. I’m going to be honest on this one and admit that I just need to let go of somethings and trust others to help me. Grade: #fail

Finish and publish my SEO book

I knew that was on the list for 2014 and I really wanted to get it done. In August I really buckled down and started working hard on the book. The writing process was tough but was nothing compared to the editing process. My editor really helped refine the book into something that I’m truly proud of (thanks Rhian!). On December 29th 2014 I finished my first book. It’s been an amazing journey that has pushed me and forced me to grow. The book is in the publishing process and will be available soon. Grade: #win

Expand my SEO offerings to clients

In 2014, along with releasing two new SEO related Shopify apps, NewLeaf Labs also started to offer more personalized and hands on SEO consulting along with copy writing. Grade #win

Drive a Tesla Model S (at least a test drive or a rental)

Man, I totally blew this one. I had a Tesla model S lined up to rent but I never pulled the trigger on it. I guess I’m going to have to move this one to the 2015 list. Grade: #epicFail

Have a  conversation with Kevin Rose, and Tim Ferris

This is another one that didn’t happen for me, then again I didn’t really try hard for it. I did have a few twitter exchanges with Kevin Rose this year but I’m not counting those. Grade: #fail

Contribute to more charities

I’m proud of this one. This year I was able to contribute more to charitable causes than ever before. One of the charities that really grabbed my attention this year was The Pratyasha Foundation. My friend Kristin lives in India and started this non-profit to provide food, health care and hope to children in the slums of India. Money donated to them goes directly to the children. I encourage you to join me in supporting Kristin in her efforts. http://thepratyashafoundation.org. Grade: #epicWin

Over all 2014 was a hard year for me. It was a time of growth and change – becoming more of a grown up. Change is never easy. Despite the challenges I was able to accomplish most of my goals in 2014. I’m looking forward to the adventures  that 2015 holds as #jacksonHighland grows up and as my wife and I welcome our second son into the world.

I used bitcoins to pay a ransom

bitcoin-hackerThis post is going to be vague in some areas to protect the identities of the parties involved.

A person I know contacted me via facebook and asked if I was still involved with bitcoin. And this is where the story begins.

This person’s friend works for a business with sensitive personal data. The businesses computers got “hacked” and  their data was encrypted. The Russian hackers were asking for $500 USD worth of bitcoins to release the data. If the demand was not met in 72 hours, the price would become $1000 USD worth of bitcoin. Finally, if the ransom was not paid within the next 72 hours period, the data on the hard drive would be destroyed.

The business was crippled because their customer data was encrypted and they needed it for their day to day tasks. Of course they didn’t have any backups of this data.

They wanted to pay the money and move on with doing business but had no idea what bitcoins were, how to acquire them or how to use them.

I was asked if I could help out and facilitate the bitcoin payment. I wanted to check off the “paid a ransom” checkbox on my bucket list, and I had never seen ransomware in person, so I agreed to help.

I had the business owner send me the $500 via paypal. Once I received the money I used my coinbase.com account to purchase the 1.43 BTC ($500 USD at the time).

The hackers had a website setup on a tor network (anonymous and private network of computers). The website had detailed instructions and information on how to pay the ransom. They provided a bitcoin wallet address, along with a field for a transaction number.


I used coinbase to send the bitcoins to the wallet, and entered the transaction number into the website. After a few minutes the transaction was verified and complete.

The website updated with instructions on how to download the decryption software and keys needed to recover the data and remove the ransomware from the computer. I forwarded the information on the the business owner and his staff.


An hour later I got an email from the business owner telling me that the data was recovered and thanking me for my help. Everything worked out. The business owner got his data, the hackers got their bitcoins, and I get to tell the story of how I paid a ransom to russian hackers with bitcoin.