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Big Ideas For Small Business Owners & Their Websites

You Never Know What Will Help

It’s often difficult to predict which arts of our lives will lead us to entrepreneurial success further down the line.

Take Jeff Chapin as an example. He’s the co-founder of a mattress company called Casper, which has done more than $100M in their two short years of existence. One of the keys to Casper’s success was the inside knowledge that Jeff brought to the table, after years of helping mattress companies optimize their organizations.

But Chapin didn’t necessarily do that job with an eye on revolutionizing the mattress industry with a multi-million dollar startup. From 2004 to 2008 he was just a guy with a job. Then he left that job, and spent five years traveling around the world working in developing countries.

It was Neil Parikh, previous founder of Consignd, who eventually approached Chapin about the idea for Casper. Neil had gone to med school with Chapin’s fiancé, and knew that Jeff understood the mattress industry. And so it was that a job he’d had nearly half a decade before became a new gateway into the startup world, and the secret sauce behind Casper’s success.

The lesson here is simple. Don’t begrudge whatever you’re doing today. Even if it doesn’t seem big or important, it could be the foundation upon which you build the next great thing. Every experience teaches us something.


How I Wrote a Bestseller In a Day (and More Importantly, Why)

Have you ever had an idea for a product or service that was just so great you knew the world would love it? Were you ever surprised when after weeks of work, and hundreds or even thousands of dollars invested, nobody seemed to want what you were selling?

Most business owners have done this at one point or another. When I was getting started, I did it several times. Our knee-jerk reaction is to dive into developing a product or service based on whether or not we think there’s demand for it. But the better way is to first confirm the demand, then spend money developing the solution.

I’d heard this philosophy many times, from many of the entrepreneurs I admired most. But it didn’t sink in on a fundamental level until I watched episode 16 of The Tim Ferriss Experiment on iTunes. There, Tim Ferriss and Noah Kagan coach a budding yoga instructor through some considerations regarding her young business. I won’t ruin the “ah-ha” moment by trying to explain it. Instead, do yourself a favor and simply buy the non-HD season pass on iTunes. It’s the best $13 you’ll spend on entertainment, and truly learning this lesson could save you thousands of times the cost of the videos over the course of your business.

I saw that episode while house-sitting in France, pondering what my next project should be. I’d recently discovered a passion for cooking, and for weeks I’d been thinking about building a website just for people who cook while they travel. The video made me think about how I could test the interest in that topic before even building the website.

There are at least two methods commonly used to test ideas for validity. The first, detailed nicely in chapter 10 of The 4-Hour Workweek, is to put up a simple landing page with either an email sign-up or a fake “Buy Now” button, then drive traffic to it and watch what happens. The second is to use a crowdfunding platform like Crowdrise or Kickstarter, where people literally vote with their money, showing you whether or not they like what you’re building.

I didn’t have enough connections in this new travel / cooking industry to drive significant traffic to a landing page, and I didn’t want to spend a bunch of money on ads. As for crowdfunding, I knew from interviews with other entrepreneurs that successful crowdfunding builds on an established audience, and a unique selling proposition. Developing those can take months, so that was out.

Then I hit on the idea of a simple Kindle book. Amazon has an enormous audience searching for new and interesting books every day. Publishing through Amazon is free, and they’ve got built-in analytics to tell you how well your book is performing.

I had never published a book with Kindle Direct Publishing before, but I’d read Guy Kawasaki’s book on self publishing, APE, and knew it wasn’t difficult. I could whip together an e-book with a simple cover, and some old blog posts for content, offer it up for free in the Kindle store, then judge the interest-level based on the number of downloads.

I set a baseline goal of ten downloads over the course of two days, with a stretch goal of 100 downloads throughout my five-day test. If I hit either of those two numbers, I’d consider the idea valid enough to proceed to the next step in testing.

Notice I said proceed to the next step in testing. That’s because free downloads prove people are willing to pay attention. They don’t necessarily prove people are willing to pay money. More intense testing (like a full-on crowdfunding campaign) would be a good idea before investing serious capital in building out any cooking courses, or video series.

Making the Kindle Book

Publishing was easy. I started by creating a Kindle Direct Publishing account. It’s linked to your normal Amazon account, so it doesn’t take more than about five minutes to set up. Then came the more complicated process of digging into the market, and creating a product to perform well within it.

Step 1: Market Research

I thought about my blog and how I could potentially make money from it. An information product could work well, either a cookbook or an e-course of some kind. I chose a price point of $20, and began combing through the Kindle Best Sellers for e-books that are in the cooking or travel sections, and were listed at or above $20.

The price point wasn’t arbitrary. Amazon offers two royalty rates for writers: 35% and 70%. If you opt for 70% your book can be no more than $9.95. But if you opt for 35% you can price as high as $200. This means that if you can sell your book for more than $20 you’re better to go with the 35% royalty rate, and price higher. It’s got the secondary benefit of positioning your book as a high-ticket item, which is good in building a strong, valuable brand.

I was also thinking about selling off of Amazon in the future. I wanted to see if people were willing to pay more than $20 in general for an electronic cookbook.

I combed through the bestseller pages, taking a small screenshot of every title I found that was both a bestseller and priced in my target zone. When I was finished I had about fifty thumbnails of best-selling e-books that were over $20. I also had a good idea of what the market looked like. For example, I knew then that cookbooks in the “Professional” category could be priced much higher than those in the international category and still perform well. I’d also seen some interesting specialty books, like books on knife-skills or bread-making, which gave me ideas on what people were interested in.

After confirming that my target price was feasible, my next step was to use my research to get an idea of what my own book cover should look like. I dumped all of my thumbnails in a single folder so I could see them all side by side and examine them in bulk.

Screen Shot 2016-02-17 at 4.33.15 PM

Immediately, I removed any that had either a famous face (one I recognized) on the cover, or a famous name in the title. Those authors had already invested heavily in building audience trust and brand recognition, so their books were likely to sell better and at higher prices than mine would.

I took the two or three-dozen books that remained, and examined their covers. There seemed to be two overall designs. One which was dominated by a picture of food, and one which was dominated by a plane background and contracting type, with some simple illustrations mixed in.

Because I didn’t want to spend any money on stock food imagery, I decided to opt for the second type. I also happened to like that version better since it looks cleaner, the titles are easier to read, and it wouldn’t lock me into presenting a certain type of food.

Step 2: Cover Design

I once spent a few weeks living with writing coach in England. There, I learned both the art of creating compelling covers.

I’m sure that a professional book designer would have some notes for me on the cover below. But in my mind it checked a few important boxes.

First, it was easily legible. On Amazon your real estate is the size of a postage stamp, and you’re competing with other postage stamp-sized book covers to catch the reader’s attention. Simple and readable is better than beautiful, but unreadable.

Second, it was intriguing while staying vague. I don’t yet know what kinds of stories my website-to-be would focus on, so I don’t want to get too specific right off the bat. I’m gauging whether or not there are people who identify as travelers, and cooks, and this cover communicates that well.


The cover quote is (perhaps obviously) mine. I own, so it’s technically not a fake quote either. Do you see how tricky marketing can be? I put the whole thing together in Adobe Illustrator, using vector illustrations from

Step 3: Draft the Intro

After my book cover was done, I set about drafting my introduction. The intro was going to be the only real content I’d write just for the book. All the rest would be copied and pasted blog posts. So I wrote it with an eye on two things.

First, I tried to explain clearly who the book was intended for. Not just to intrigue the right readers, but to keep the wrong readers from downloading it and throwing off my test.

Second, and I think more importantly, I plainly explained the experiment I was running. I don’t think you get any points for being cunning when it comes to building an audience, and I didn’t want to disappoint people on our very first interaction.

I told them that the book was unfinished, and that it simply contained a bunch of old blog articles duplicated over and over again until it was roughly the length of the book I’d like to write. I told them what I wanted to write about, and said if they were interested in reading about those things that they should download the book to help me in my experiment. Then I invited them to read what was there (they weren’t bad blog posts), and thanked them for their time.

I’m not sure I can emphasize this enough. The goal was not to trick people into downloading something. People don’t like being tricked, and they especially don’t like having their time wasted. By being honest up front, you may decrease the initial interest in what you’re offering, but you also mitigate against damaging your reputation.

Step 4: Create the e-Book

To create the e-book I picked a few of my favorite essays that I’d written on food and travel, and copied them into a scrivener file. Scrivener is a professional writing tool that can easily be used to export into e-book formats.

I did a little basic work to remove photos, and references to embedded videos, then simply duplicated the posts over and over again until the book was approximately the length I was looking for. I did that because I know Amazon shares length statistics in the product description, and I wanted the test-subject to be as close as possible to the real thing.

A Youtube video showed me how to quickly export the book as a .mobi file, which is the best format for uploading Amazon Kindle books. And with that final detail I was off to the races.

Step 5: Publishing


After filling out some basic info about the book (title, author, description, etc…) I set the price at $25 and waited for it to go live. The next morning, I enrolled the book in KDP Select program, which allows you to promote your book as $0 for five days out of every 90.

This gets you some added visibility on Amazon, and of course because the book is free, it’s much more likely to move. That makes it more likely that it will get reviews, which in turn makes it more likely to sell once the promotion is over.

Once my book was in the Kindle store, priced at $0, I had a friend write a single five-star review. Then there was nothing to do but wait.


I filled the time with important things like long walks in the Brittany countryside, sawing stacks of wood for the oversized fireplace in the house I was sitting, and binge-watching the entire first season of House.

Basically, I did everything I could to avoid any further work on the project until the market had either verified or rejected the idea.

Recall that my goal was four downloads per day, or ten over the course of three days with a stretch goal of 100.

The book got 50 downloads in the first day alone, and surpassed my stretch goal by the third day, rising to #10 in the Bestsellers list of Cooking Reference books before I finally pulled it.


All told there were more than 160 downloads in the first three days. Now that’s a far, far cry from a New York Times best seller, and even if it weren’t free, those numbers wouldn’t bring in much money. But they’d passed my litmus test, and to have done that with zero personal marketing, one review, and a hastily put together book meant that there was likely a good deal more that was possible with some legitimate time and effort.

I’d verified at least a baseline interest int he market, and could justify moving to the next step in testing. And so it was that Cooking Travelers was born.



Find Your Failure Points Before They Find You

I woke up to sunshine streaming through huge picture windows that looked out over the French countryside. Back home in New England, the streets were covered with ice and snow. But here I saw nothing but endless green cow pastures beneath a dome of jewel-blue sky. I’d chosen the right time to try pet-sitting in Europe.

As I walked down the stairs to get breakfast going, I noticed a strange sound coming from the living room, like fingernails on rough plastic. I looked over in time to see the cat, Ella, perched atop the house’s internet router, which itself lay on a waist-high table near the front door. She stretched her front legs, stepping off the router, nudging it close to the edge of the table as she went.

My heart stopped. I hadn’t realized until that moment how unbelievably screwed I’d be if the internet suddenly blinked out.

My business would be put on hold until I could get the router fixed, that was certain. While I was completely location independent, I still had to show up in order to make money. No internet, no income.

I wouldn’t know where to buy a replacement, since I’d relied on Google maps to get me around, and even if I did it’d be difficult since I was in the French countryside and didn’t speak one lick of the language.

Depending too heavily on any given thing — whether it’s a single technology, client, or revenue stream — puts us in a bad position. As business owners we want to be independent, and that means existing in a state of non-dependence.

Is there any single thing you could lose that would create a domino failure effect?

Are you relying too heavily on any single person (including yourself), or technology (like a specific social media platform)? If so, how could you shift to a state of lower dependence.

Figuring it out ahead of time will help keep you from ending up trapped.

Now, if you’ll excuse me, I’m off to brush up on my français.

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