From failed course to bestselling book – the making of The College Entrepreneur

No use, I could not get back to sleep. The first light of day was starting to shine through my window. What in the world was I doing up at 5am on a Sunday? One of my favorite Steven Pressfield quotes from the War of Art echoed in my mind:

I remember rolling the last page out and adding it to the stack that was the finished manuscript. Nobody knew I was done. Nobody cared. But I knew. I felt like a dragon I’d been fighting all my life had just dropped dead at my feet and gasped out its last sulfuric breath.  

Rest in peace, motherfucker.

Today, I too had slain a dragon.

It was launch day for my book, and though I was too excited to sleep, I felt confident in what I was doing and what I had created. It wasn’t perfect, but it was ready.

Everything was in place, the book was listed on Amazon, a free promotion was set up. I was registered to promote my book on a few different websites while it was free. I had an amazing team of people ready to download, share and review the book.

This day did not magically happen; it was the result of a few years of honing an idea, experiments and a few epic fails.

This is the story of the creation of The College Entrepreneur. I’ll share the highlights and the lowlights of this journey, and the lessons I learned in the process.

The College Entrepreneur

Why start?

I didn’t know this was going to be a book at first. This idea took many different forms over the past few years.

The main drive came from a problem I had sensed for years. I graduated from the University of Utah in 2010, at the peak of the Recession. Many of my friends had graduated around that time as well. After a lifetime of following the instructions of “get good grades and you’ll get a good job when you arrive in ‘the real world’,” it seemed like ‘the real world’ was not holding up it’s end of the bargain.

The game had changed, and I felt students needed a new plan.

I spent 8 years at the University of Utah in one form or another. I earned both my Bachelor’s and Master’s degrees there. I also worked as a student employee, intern, full-time advisor and even adjunct faculty. This time and diverse experience in higher education, along with experience working with startups and small businesses, inspired me to present a new strategy to anyone seeking to improve themselves through education.

But I was not quite sure what to do with this knowledge.

Overcoming fear

Throughout this whole process, the biggest resistance I faced was internal. I was afraid to share this idea.

After 3 years of being involved in the dialogue around entrepreneurship, it seemed that many brilliant people thought young kids should avoid college alltogether. It was a huge debt sink and was not a good investment of time or money. Someone looking to get into entrepreneurship or any kind of competitive career should simply self-educate themselves through the process of starting a project of their own.

I think this is a great idea, and it is something that every young person should consider before committing to a university. A semester’s worth of tuition could easily buy you over a year living in Chiang Mai, Thailand, where you would be immersed in a community of young entrepreneurs and hustlers trying to build wealth online. Even if entrepreneurship is not your thing, a year of travel and exposure to different ideas, lifestyles and perspectives can be life-changing.

While I agree that the university system is fundamentally flawed right now, I don’t think we can afford to wait for the system to correct itself. But I do believe that students have the power to take control of their education and make their university work for them.

I was afraid that the ideas in my book would attract flack from both sides of the argument. The entrepreneurs would assume I’m taking the side of the university and encouraging young people to shackle themselves with debt. Those of the university would think I am just encouraging students to extract as much value as possible and drop out of the system.

There was also a more subtle thought pattern that I have struggled against for my entire entrepreneurial career. I was afraid I was not worthy to talk about this topic, even though I have experience, perhaps it’s not enough to encourage people to start their own business, or that my experience at a university would not translate to something that could be useful for others.

This fear held me back at many stages. It was a subtle resistance to work through during the whole creation process, and it likely stifled my marketing a bit. I didn’t speak as loudly about the book or reach out to as many people because of the doubts I harbored about people’s response.

I think many people face similar problems when writing their first book. Here’s a few ways I overcame these blocks.

  • Work through it – In the beginning, it will be difficult to overcome fears and doubts, and in the early stages, you won’t have much evidence to the contrary. At this point, your best bet is just to push yourself through and start creating. Act despite the feeling and start to develop your ideas. Through the process of creation, you’ll start to refine your ideas and build confidence in what you are doing.
  • Write a letter to yourself – This sounds corny, but on days when I was stressed or uncertain, I wrote a letter to myself reminding me of everything I had done to get me to this point. I would praise myself and encourage myself to continue. In this process, you need to be your own biggest cheerleader and provide your own emotional support. This letter tactic helped me press on.
  • Talk to people – I set up calls with friends, colleagues and others that I found participating in the discussion on higher education, and I asked their opinions on some of my ideas. At first, it took a while to get the thoughts to click in others or frame them in a way that was easily understood, but as I continued with the conversations, I found better ways to explain myself. This helped build confidence in the project and gave me a better frame for my writing.

Early Stages

At first, I did not set out to create a book. I was aiming for an online course. It seemed like the best format for me at the time. Marketplaces like Udemy have millions of users. I decided it would be best to go where there are a lot of people already.

I had a few core lessons and stories that I wanted to build the course around, but I also had to tease out many of the other ideas over time.

The first step was writing the ideas I wanted to cover in Evernote and adding notes or comments underneath the main points as they came to mind.

Organized with Trello

To keep organized while creating the course, I used Trello. You can use it to organize all kinds of work you are doing; it’s great for teams and for individuals. Plus it’s free.

If you are new to Trello and would like a little more depth on how to make the most of this amazing tool, check out this extensive guide for getting the most out of Trello here.

Trello board

Using lists in Trello

I mapped out the main sections and ideas in lists and had individual lessons in cards. Each list represented a “part” of the course. This was really nice to drag ideas between the lists and visualize the overall structure for the course.

I have seen other authors use the different lists as a way to visualize the status of each chapter. So the first list would be “drafting,” another would be “complete” and so on.

Using the cards in Trello

Each card would have the working title of the chapter as its name. I would attach the Google doc where I was writing the outline for the lesson and the link to the slides I created in Prezi for the lesson to the card as well as any articles, images, or other ideas for the lesson in the card.

Having the chapters in separate docs in the early stages was helpful. I eventually combined all of the documents into 1 master document once it was ready for editing, but I don’t recommend doing it until you are finished with your draft and want it all in one place. Google docs seems to get clunky when dealing with larger documents. It would scroll more slowly and strange formatting errors would appear.

There were a lot of different lessons to keep track of, so I used the labeling system in Trello to have a system of colors that would help me quickly determine the status of the lesson in the cards without having to go into each one individually.

Trello lists and lables

In April 2015, I had finished all of the recorded materials for the first round of my course. But unfortunately since I was living in a small bungalow in Thailand, most of the audio was filled with bird or bug noises that were distracting. Despite some attempts to try and clean up the audio, the course was not ready to launch as is.


I decided to shelve the project until I was in a better place for recording. It was nearly half a year before I picked it back up again. It was difficult to return to the course; it felt like I had already failed and there was not a place for these ideas.

I returned to Thailand for a conference in October of 2015 and spent 2 months in Chaing Mai. It was there I found the motivation to finish the course. It was only a matter of re-recording most of the presentations and fixing up a few of them.

I was determined to have excellent sound quality this time. I used the comforter from my bed in my apartment to muffle the echoes by pulling it over my head and recording. I had to unplug any other electronics that buzzed like my fridge and turn off the air conditioning.

Luckily, the lessons were only about 3-5 minutes long, which was about all I could survive in the heat of Thailand with a blanket over my head. I would record, emerge covered in sweat, turn on the AC and edit the lesson. Once the lesson was solid, I would return to another round of recording.

The course was re-created in 2 sweaty weekends and launched shortly after.

Lessons from the second course launch

The course was good; it contained a lot of the same ideas that the completed book now had, but I did not like how it was framed. I focused on helping students on a “job search” instead of on developing an entrepreneurial mindset, and the course was lacking in stories to give it flavor. It would just share the information point blank without the context of a story.

The title of the course was “How to get your university to pay you to job hunt,” which is a mouthful and still not very clear on the value it delivers. This made it difficult to position in front of the right people and share the message.

Most of these defects were rooted in my fear. I avoided discussing entrepreneurship because I was not sure I deserved to talk about that topic and kept my own story out of the picture for a similar reason. This left the course feeling stale, making it harder to muster the energy to promote it.

Another problem was that I usually worked on the course after a long day of working. I believe you only have so much smartness in a day, and I find that usually by 5 or 6 pm, mine is mostly spent. Creative work is challenging and demanding, and deserves the best that you have to offer. Personally, I found myself to be sharpest in the mornings, and if I ever create another course or revisit this one I’ll work on it in the mornings.

Waking up early is a pain for most people, but I think a lot of that is because the first thing most people end up doing is heading to work for someone else. I find that waking up early to invest in yourself can be much more gratifying. If you want to learn more about the power that you can harness in the early morning, I recommend checking out The Miracle Morning by Hal Elrod.

So despite improved audio quality and some refined content, the idea had not yet hit the mark for me.

Becoming the book

A few months after launching the course, I was introduced to Self-Publishing School and Book Launch by Chandler Bolt.

I had wanted to write a book, but I didn’t think it would be for a few years. Self-Publishing School helped me build the confidence to commit to the project and also gave detailed instructions for what to do at each stage of book creation, from mapping out your ideas to launching on Amazon.

Unlike the course, my book was my main priority while I was writing it. The first work I would do in the mornings was focus on writing 1000 words a day. I would open up the Trello board, pick one of the lessons and begin filling it out with more details.

A big lesson here is how valuable it can be to map and outline your ideas thoroughly before you begin heavily investing your time in writing.

I went back to the Trello board that contained all of my notes and scripts for my course, and began turning the outlines for lessons into chapters. The writing process at this point was fairly simple. Since most of the book’s content had been mapped out, it was just a matter of putting in the work.

If you can have your ideas organized on something like the Trello board I mentioned earlier, it will prevent you from getting writer’s block or getting lost in what you are creating. Since I had outlines for each chapter I had to write leftover from the lessons I recorded, it was easy to drop into writing every day.

Connecting to readers with storytelling

As I mentioned earlier, a big element that I thought was missing from my course were stories that exemplified the ideas and made them more relatable to the average student. I began reading “Wired For Story by Lisa Cron” to improve my storytelling skills. Though this book focuses on writing fiction, the lessons can be applied to all kinds of writing. Here’s a few of my highlights:

  • Your book idea should be easily summarized in a few sentences.
  • Storytelling is more important than beautiful writing.
  • The story should start in the middle of the action or foreshadow the main problem and upcoming conflict. People crave the conflict in a story.
  • The protagonist in the story needs to have a goal and obvious reasons to pursue that goal.
  • Readers assume that everything the writer tells them is on a need-to-know basis. Everything you write should add to your main point or enhance the story. Anything else is just a distraction for your readers.

I opened up each chapter with a short story, usually from my own life, that served as an example for the concept I wanted to teach.

Every entrepreneur has a unique journey, they have different challenges and inherent strengths, they want to make an impact in different ways. I knew that my experience was was not enough to fully capture the idea I wanted to share.

To bring some diversity into the book, I reached out to many other young entrepreneurs and influencers to add their stories to the project. I tried to paint a broad picture of both male and female entrepreneurs across the world that offered different products or services and used different strategies to grow their business.

This added a lot of personality to the book, and it also helped with the early marketing. By adding more stories into the chapters and making them the heroes of the book, it enrolled some early fans to help promote the book.

Building anticipation for the book

You can’t just list your book on Amazon and expect sales to automatically happen. You need to engineer a launch that pushes you above the noise and allows your book to get noticed by the target audience.

Once the rough draft was completed, I began to get the book in front of people and started preparing for my launch.

I started with a few very early readers to see how they responded to the ideas and the flow of the book. I enlisted a few close friends who had the patience to read through my un-edited work. These early readers yielded some very surprising insights. They pointed out some lines and statements that were resonating with them and some areas where they were confused or simply bored. This early feedback helped me refine the draft and gave some good points to discuss with my editor.

Before I started actively collecting emails for the book launch, I began to tell the story of my book on social media and gave people the opportunity to participate in its creation. I started by proposing several different titles and subtitles for the book and asked my friends to vote on their favorite. This was valuable in so many ways: the title that ended up winning was not what I would have chosen on my own, and it started to get people excited about the upcoming launch.

I used the same tactic with my book cover. This attracted a wealth of comments and fresh ideas for the design. Again I was surprised by how different the response was from what I thought was the best cover. We ended up using the colors and fonts from one design and the graphics and layout from another for the final product. Without this early input, the cover and title would likely have been very different.

Facebook voting on cover design

One of the most successful moves to promote the book was a short video I made right after receiving my first physical proof of the book. When I set out to write this book, I didn’t think I would be able to have a physical copy at the launch. Many people had a similar expectation and thought the book was only going to be a digital release.

I enrolled in Amazon’s Create Space program, which allows you to print books on demand. I didn’t need to order thousands up front and figure out where to keep them. If someone ordered a book online, it would be printed and shipped on the spot.

I ordered my first proof to make sure it looked good. When it arrived, I was blown away. The book was much thicker than I expected it to be, and the formatting and cover design looked great. I recorded a simple video to share my excitement.

This video of me holding a physical copy of the book made the process feel “real” to everyone. I believe many people thought it was just going to be a digital release and discounted the book in their minds because of it. The video showing the physical book and my excitement for it energized my audience.

Building the launch team

I didn’t have a large brand, email list or social media following to draw on to help with the book launch. But I did have contacts at several universities and friends with brothers, sisters, sons and daughters who were heading to college soon.

Many of my friends graduated somewhere around 2010 at the peak of the recession. They understood the challenges of getting a good job after graduation and were excited to see and support the book.

I created a simple landing page that talked about the book and offered the book for free to anyone who would help with the launch. I posted a link to the page on social media and asked for the support of anyone willing to leave a review.

There was a good initial response, but to really grow the list, I had to hustle. I reached out to people by email, messenger, phone and in person to enroll them to help one-by-one. I found that many people were willing to help with a personal request from me, so I made this my top priority in the weeks leading up to the launch.

I sent a few emails out before the launch, welcoming people to the launch team, reminding them about the launch, and telling stories of how the book was coming along. I also used some animated GIF images to add some entertainment value to the email.

How to get a little help from your friends

I had a lot of friends and colleagues who were excited that I was writing a book, though it was not relevant to them at this point in their lives. They wanted to support me, but I thought it would be challenging to get them to take action online.

The day before launch (June 18th, 2016), I hosted a BBQ at my house, offering a nice beer from Epic Brewery if they would come, check out the book and leave a review on Amazon. I knew my friends would be excited to come enjoy some food and fun while supporting me at the same time.

The book was on Amazon even though it had not officially launched yet, and people were able to leave reviews. I wanted to collect some early reviews to qualify for some book promotion sites (Self-Publishing School has a huge list of these and discounts to many of them).

I had the book on display, so people could give it a quick read and come up with some good things to mention in their review.

Book launch BBQ

The BBQ was a big success and I had collected a lot of reviews online. There was however, one big setback.

  • I had my laptop out so it was easy for people to log into their Amazon account and leave a review. But Amazon detected that all of these reviews were coming from the same IP address, which made it look suspicious, and many of my reviews were removed. Still a majority of the people that came left a review from their phone, and these ones were not removed.

Creating a personal connection with postcards

As I continued to promote the book, more and more friends, teachers and mentors from different stages of my life came forward to help. They were excited I was writing a book and wanted to support me.

These personal relationships were crucial to the book’s success. But they weren’t exactly the target audience for the book, so it did not make sense to use incentives related to the book to encourage them to take action. Personal connections needed a personal touch.

The solution was the postcard campaign. I created a landing page that offered a handwritten postcard for anyone that reviewed the book during the launch week. One big lesson in the book outlines the power that a handwritten “thank you” card can have on people who have helped you. It makes them feel great and invites more of what you are thankful for in your life.

I saw a few benefits from this campaign idea.

  • Almost nobody sends or receives postcards any more so a physical card could last for years on a fridge, desk or cork board, and serve as a conversation piece.
  • There’s a lot of noise on social media, email and online in general. I thought using a low-tech tactic would make this launch more memorable and meaningful to those who participated.

Launch day

Launch day was June 19th. With Amazon’s Kindle Direct Publishing Select program, you are allowed to sell your book for free for up to 5 days. I launched with a free promotion and listed my book on a dozen or more free promotion sites.

The work does not end on the first day. You need to keep your audience engaged and excited. I continued to share little updates and tell the story of the book.

When a big influencer like Chris Guillebeau shared the book, I would take a screenshot and let my list know so they could celebrate the big win. Because of this, I was able to get a lot more leverage out of a tweet that was likely buried quickly in Twitter, but once I re-shared it on Facebook, it was liked, commented on and shared, which consistently pushed it back up the feed and helped me reach more of my audience.


Switching from free to paid

One tricky part of a launch is switching from the free store to the paid store. If your free promotion does well, then you’ll have some momentum to carry into the paid store. But you need to work hard to keep interest up and continue to get sales and reviews.

Pricing your book at 99 cents qualifies you for other book promotion sites, and you’ll likely still have some stragglers on your email list that have not yet purchased the book or left a review. 99 cents is practically free, so it’s still an easy sell for most, but it still counts as a purchase which will help keep you high in the Amazon rankings and get you more exposure.

I continued to share stories about the book and tried to create a sense of competition in the book launch. I noticed that I was right behind a Bill O’Reilly book in one of the categories my book was listed in. Bill is a very polarizing character and made a perfect “opponent” in the store. This energized some people to buy the book or leave a review to try and “beat” Bill.


Becoming a bestseller

To make bestseller, you need to hit #1 in a category in Amazon. It’s important to do your homework on the different categories that exist and find a few that your book will be relevant to and perform well in. With a strong launch, it’s possible to hold the top spot in a few different categories for at least a few days.

Being at the top will also make you appear on the “Hot new releases” tab in similar categories, which spreads your reach and boost your sales.

After experimenting with a few different categories, I found a good niche that I could dominate. After refreshing the Amazon page for the 38,000th time, I saw the tag.


What’s next?

The dragon may have been slain; the book was launched, but this is just the start of something bigger. Though a book can be a very profitable creation, it should serve as the foundation for something bigger. It should attract customers to your business, or promote a brand or service.

Though I won’t be retiring on book royalties anytime soon, it has opened up opportunities for me to do workshops, events and classroom visits at various universities. The coming year, I will focus on developing these workshops and traveling to as many universities as possible to speak with students, share these ideas and be a bigger service to student entrepreneurs.


Writing a book is difficult, but not as difficult as you might think. There’s never been a better time in history to write one. The barriers that once made being an author so difficult have almost completely dissolved.

With an idea, some grit and consistent action, you too can write a book.

Good luck! And please follow up if this helps you in your journey.


Kyle Gray
Kyle Gray is the founder of Conversion Cake, where he helps small businesses and startups with content marketing strategy and sales funnels. He is also the author of “The College Entrepreneur” a guide that teaches students how to build an entrepreneurial skillset while in school and use their university’s resources to help them build something amazing.