Read How I Made $75,000 As A First Time Author

The SponsorMyBook website was live from October 2013 to January 2015. Because the book, Creativity For Sale, has it’s own website. This will serve as the resting place for SponsorMyBook.

Conceiving The Idea

I like to refer to 2013 as “the year of the burrito.” Why? It’s not because I ate a burrito every day and talked about it on social media (though that does sound deliciously fun). 2013 was “the year of the burrito” because while eating at a TexMex place with my friend Dave Cohen, the decision was made to write my first book.

We’d only hung out a few times before, but this burrito-filled lunch would be different. I was just coming back from an amazing event in Fargo, North Dakota where I wrote this article about feeling lost. I had recently made the decision to hang up my final t-shirt for IWearYourShirt and I was feeling pretty down in the dumps (something I’d hoped guacamole and steak wrapped in a flour tortilla would help).

One thing I’m not even sure my friend Dave knew at the time: I was $100,000 in debt and only had $9 (total) in my bank accounts. So, technically, my net worth at that lunch was -$99,991. Needless to say, I’d be letting Dave buy the burritos.

Let it be known this wasn’t a lunch meeting about writing a book. It wasn’t a lunch meeting I expected anything from. It was simply an opportunity for me to escape my thoughts for an hour with a friend.

As we enjoyed our lunch I told Dave how I was feeling. I told him I didn’t know what to do next. I told him I felt lost. I told him I felt like I was in a creative slump. If you’re keeping track of the burrito; at this point I’d probably eaten the first quarter of it.

Dave started to ask me questions about what I wanted to be doing and I didn’t really have an answer for him. Then he asked, as I got about halfway done with my burrito:

“Why don’t you write a book about your story?”

Write a book about my story? I was a failure. IWearYourShirt had generated over $1,000,000 since 2008, but I didn’t have any of that money left. In fact, I had to take a personal loan and max out all my credit cards to keep IWearYourShirt afloat for the final year. Why would anyone care to read a story about my failed business?

I didn’t necessarily lay all of those thoughts out to Dave, but what I did say was this: “People have told me to write a book about my story, but it doesn’t have a happy ending. I didn’t go through a struggle and then end up with $20M in the bank.” Then Dave said something I’ll never forget: “Not every book needs a happy ending.”

Mind = Blown.

I was nearing 3/4 completion of my burrito and thoughts of writing a book start to dance around my head. I could share a ton of lessons I learned along my entrepreneurial journey. I could share things I’d always wanted to share, but didn’t feel were right to talk about while promoting a different company each day. But would people care? Would someone actually buy a book written by me? I’m not a writer. Who am I to write a book? Did a little bit of ranch dressing end up in my burrito? I hate ranch dressing.

Dave’s Infinite Wisdom

After voicing a few of the concerns that were dancing around in my head, especially one about not knowing how my story would end in the book, Dave told me that many authors have no clue how their books will end before they start writing. But, they just start writing and see where their authoring journey takes them.

At this point I was nearly done with my burrito and I was feeling really good about the story I could share. Whether it was the dopamine response from the food, Dave’s thoughts and calming presence, or a mix of both, I had some mental momentum.

We finished up our lunch and I told Dave: “I’m going to do it. I’m going to write a book. I’m going to become an author.” We bro-hugged and went our separate ways (and yes, Dave paid for lunch in case you were keeping score at home).

The Drive Home

When an idea enters my brain the neurons start to fire like a fireworks finale on the 4th of July. The entire drive home from lunch I was consumed with thoughts of doing something unique with my book. Putting some twist on it, that was a reflection of the way I’d done things in previous years with IWearYourShirt and BuyMyLastName. I couldn’t simply write a book and put it up for sale on Amazon. It had to be different.

Then it hit me, while sitting at a red light. I’ve had so many other projects sponsored, why not my book? It’s a logical step in my story. I have a good rolodex of companies that have sponsored me before. What if I offered sponsorships on the pages throughout the book? I’d never seen that done before (maybe for good reason….).

And then I thought about the IWearYourShirt pricing model I’d come up with in 2008. (The “Bumpsale” pricing as I call it now.) What if there were sponsorships on every page of the book and the price changed per page? The front of the book would be the most valuable real estate, since a lot of people don’t finish reading books. So what if I picked a price to sponsor Page #1 and as you got further in the book the price got lower. Heck, I could probably even get sponsors for the front and back covers of the book (and charge more for those).

It was at this point I was pulling into my driveway. Have you ever ended up at your destination, but aren’t able to recall much of the drive? Yep, that’s the exact feeling I had. Luckily my car seemed in perfect condition and I was dragging a fence or tree branches behind it.

Running The Numbers

Because I’m not a mathematician, I popped open my laptop and created an excel spreadsheet. I quickly threw a couple numbers in columns and rows.

I decided I would write a 200-page book. It felt like the right length. It felt like 200 sponsors would be obtainable. I had thought about doing 365 pages (to honor the original IWearYourShirt pricing), but that seemed like too long of a book to write, even if I used an enormous font size throughout.

An illustrated version of the conception of SponsorMyBook (by Caroline Winegeart):

The Year of the Burrito Eating my way through my sorrows Mmm guacamole I could write a book I'm going to be an author!

The original sketches of the SponsorMyBook website.

SponsorMyBook Sketch SponsorMyBook Sketch SponsorMyBook Sketch SponsorMyBook Sketch SponsorMyBook Sketch SponsorMyBook Sketch

As I crunched a few numbers I randomly tried making the last page $3 and wanted to see what I’d end up with at Page #1 if I increased each page’s value by $3. I can’t explain why I chose $3, but I guessed it would end up around $600 on Page #1 (200 * 3?).

Sure enough it did. Starting on Page #1 at $600 and decreasing the price per page by $3 ($597, $594, $591, etc) ended up with Page #200 priced at $3. If all the pages got sponsored I’d stand to make $60,000. Let’s roll with it!

Reaching Out To My Trust Circle

I’d hadn’t yet written this article about trust circles, but it was something I’d done over the years with all my ideas. That is, emailing a small group of people (not close friends or family) and asking for their unbiased feedback about an idea.

I emailed a handful of people about this idea. Some of them were existing authors and some were just fellow entrepreneurs. In that email I asked about book publishers and book agents, thinking I might need to find those people while getting my book sponsored.

The response was overwhelmingly similar and it went something like this: “Jason, don’t waste your time with book publishers. They won’t do anything for a first-time author and probably won’t give you any money. You’ll have to do all the work marketing your book. You have a community, just self-publish and keep 100% of your revenue.”

Well, that was all I needed to hear.

I decided I wouldn’t bother trying to convince a book publisher or book agent that my book would be worth their time. Instead, I gave myself permission to write my own book. I gave myself permission to market my book in my own unique way (trying to get it sponsored before even writing the book…). All my other projects had been done on my own, SponsorMyBook would be no different.

Buying The Domain Is Always The Beginning

Once I had fully committed to this idea it was time to name it. I’d been calling it SponsorMyBook in all my notes, but hadn’t even checked if the domain was available. Three clicks later and I owned SponsorMyBook.com. To be honest, I was kind of surprised it was still available, but then again, I was also surprised when BuyMyLastName.com was available.

I spent some time sketching out loose wireframes for the SponsorMyBook website in my notebook. The original sketches are shown at left. These sketches were sent to a freelance designer I was using for all my projects at the time. Within a week I had a fully designed website, ready for implementation.

(If you’re keeping track at home, yes, I still only had about $9 in my bank account at this time. I asked the designer if I could pay him once the first few sponsors paid. Luckily he agreed… Not that I could have paid him anyway.)

Now that I had a finished design I reached out to my friend Conrad to ask if he could help bring SponsorMyBook to life. I’d worked with Conrad on a few previous projects, one of which included using Shopify as an e-commerce platform that could be customized. I figured this could be an easy project (hah, sorry Conrad!) since it was somewhat similar to what we worked on before.

Conrad, being the awesome friend that he is, stepped up to the plate and knocked the project out of the park. Within a few days the Page Sponsorship purchase process was ready. The Cover Sponsorships were ready to be bought. Things were really coming together. Now it was time to put in the real work.

Sending Over 2,000 Emails

Before I started the public push to get sponsorships for SponsorMyBook, I shared the project with about 50 friends. These were all people that had sponsored other projects I’d done and people I thought would be intrigued by this project.

So I created a Google Spreadsheet, put their names and emails in it, and then started emailing them about the project. My pitch was that they were getting first dibs on the first 10 pages of the book before it was being announced publicly. Out of those 50 emails about half of the people (politely) declined right away. Four people said yes immediately (thank you James P, Bryan B, Michael G, Mike W).

This was enough proof for me that people would pay for the page sponsorships. This also afforded me the ability to pay my designer and have more than $9 in my bank account (truthfully, not that much more…).

I launched SponsorMyBook to my email list and on social media. Over 100 pages were sold in the first few hours and my Shopify account had quickly collected over $10,000. F*&k yes!

For the next few weeks and months I fielded a crapload of emails. Between emails I sent pitching previous sponsors and companies I liked, and the requests that came in from my email list and social media, I estimate that I sent over 2,000 emails in five months. Many people didn’t quite understand what I was doing with SponsorMyBook. Many wanted to get on board but didn’t have a project to promote. Needless to say, it took an incredible amount of work to land all 200 sponsorships.

Many people have emailed me since launching SponsorMyBook asking how they can get their book sponsored. The answer is simple: Send 2,000 emails. Okay, maybe it’s not that simple, but hard work and persistence pays off.

Landing The Cover Sponsors

Thankfully GoStats and Design Extensions jumped on the opportunity to sponsor the inside cover flaps of the book without much cajoling from me.

The back cover sponsor is where Dave Cohen makes his way back into the story. During the months that I’d been hustling to fill my book with sponsors he and I had shared a few more meals together (eating burritos, pounds of smoked meats, and more). The more we talked about my book the more it seemed we should try to work together. At the time, Dave was working for a company called Round Table Companies (RTC). If you’ve already seen my book or clicked the SponsorMyBook website image above, then you know they stepped up to sponsor the back cover of my book. Dave’s involvement in the push for me to write a book and the actual services that RTC provided were absolutely integral in making my authoring journey a successful one.

The front cover sponsor, on the other hand, was quite a different story.

I’d had people kicking the tires on the front cover sponsorship, but at a price tag of $20,000 the tire kicking typically didn’t last long. I took a few phone calls with interested companies, but none of them felt like a good fit for my book and for my story (yes, I’m saying I turned down a few $20,000 sponsorships).

There were two companies that I had decided would be the final contenders for the front cover sponsorship. Either one of them would bite, or the cover would go without a sponsor. Those two companies were MOO and Treehouse. (You may already know how this story turns out, but let me share two videos with you regardless.)

I knew that an email wouldn’t be enough to convince a company to spend $20,000. I knew my book would be about creativity. I knew I had to do something unique to get the attention of these two companies. But which one to pitch first?

I flipped a coin. Heads was Treehouse and tails was MOO. The coin landed on tails. MOO would be the first pitch.

I grabbed my notebook and wrote down a few ideas on how to pitch MOO. Then it hit me: Why not write a message on a bunch of business cards and then have MOO print the cards (hoping they’d quality check them and read the message)?

A few hours later I had finished writing my cryptic message and designing the cards. Then I placed the order on their site. About a week later the MOO cards showed up at my door. No note. No response via email. Nothing. “That’s okay” I told myself. My intention was to film a video anyway. After a full day of filming, this is what I ended up with:

Not bad right? Unique? Creative? Interesting? I thought so too! Alas… MOO did not.

I emailed them, tweeted them, posted on their Facebook page. Nothing. I finally filed a customer support ticket just to try to catch the ear of someone at their company. A nice gentleman and I exchanged a few emails. He said he would try to pass the video to the marketing team but couldn’t promise anything. He was correct. MOO wasn’t interested.

Bummer.

But now I had the company on the other side of the coin: Treehouse. My girlfriend had been using Treehouse right around this same time to teach herself CSS and a few other things. She had told me how awesome their online classes were and how much fun it was.

So I went back to my notebook. I wrote down a few ideas, but one thing I kept finding myself doing was sketching the Treehouse logo (a tree frog’s hand.. Paw? Do frogs have hands or paws?). As I finished sketching I decided that’s what I’d do: Sketch out the front cover sponsorship pitch and make that the subject of the video.

Enter the Treehouse pitch video:

Once the video was done I emailed it to Treehouse’s founder Ryan Carson. We’d previously exchanged emails before, but now I had something really out-of-the-box to share. And it worked. Just twenty minutes after emailing him the link to the video he Cc’d someone else at Treehouse and said something to the effect of “let’s chat.”

Now, I can’t share the exact amount Treehouse paid, but it wasn’t $20,000 and it wasn’t $9. Just know it was something in between those two.

I was ecstatic. Treehouse embodied everything I’d eventually talk about in my book and was a perfect fit for the demographic of people I’d imagined would read my book (creative entrepreneurs).

From There, The Rest Is History

There are plenty of other stories to share and lessons learned on the SponsorMyBook journey. The most important thing for me though, was that I wasn’t willing to give up on the dream of getting my book fully sponsored. I wanted to achieve my goal and I wasn’t going to let anything stop me.

Creativity For Sale hasn’t gone on to become a best seller. It hasn’t been on the Wall Street Journal or New York Times lists. It also hasn’t been in the hands of anyone famous. But is has impacted creative entrepreneurs around the world. Over 10,000 people have purchased or downloaded the book. And hundreds of those people have emailed or messaged me saying my little book has made a huge impact on their lives.

To me, that’s all the validation I will ever need.

Thank you to everyone involved in making SponsorMyBook a success. My friends and family. The sponsors of the book. The supporters of the back (on a page in the back). And to everyone who’s bought the book. It means the world to me. Thank you.

Useful Links:

Buy Creativity For Sale on Amazon.com

Get a free 14-day trial with Treehouse