The plan was to land a quiet, easy day job and work on building a software business until I was making enough on the side to quit. But after five years, the plan was clearly not working. I was experiencing total boredom during the day, taking customer development phone calls at lunch, and grinding away at code at night — my passion and enthusiasm dried up quickly when nobody cared about what I was doing.
The day-job-pays-for-side-projects plan failed. So I quit my job.
An education in entrepreneurship
The rest of my story and how I grew my email list to over 3,000 people and made over $15,000 is really just me executing what I learned from these smart, successful business owners to the best of my ability.
Lesson #1: Choose your customers carefully
You should start with customers, not a product.
If you start with people, invest time in understanding the daily aches and pains of their lives, and you actually create a decent product to solve those problems, you will make money. It’s almost guaranteed.
So it follows if step one is to understand your customers, you should pick the customers that you want.
I decided I wanted my customers to have money and be inclined to spend it. They should also be working on things I'm interested in, so I don't get too bored making stuff for them later. (It does get boring fast. Just trust me on this.) They should also hang out on the web, because otherwise I would have no idea how to reach them.
There are other qualifications, but these are the most important.
It's easier to relate to people when you've already been in their shoes. It's easier to market to them, easier to understand their problems, and easier to identify pains big enough for you to solve and charge money for.
Lesson #2: Have some empathy for your customers
The next step is to really understand your customers and what they struggle with every day. Look for pain, anguish, guilt, and frustration. Take that pain away...and make $$$.
Don't do customer interviews. I used to do these, but people lie (usually to be nice). Instead, go read what they say on the sites where they hang out. The results will be more truthful.
I read hundreds, probably thousands, of articles and forum threads until I discovered some patterns. Here is one example of many articles I found filled with really frustrated people. I wanted to help them!
(P.S. If you want to build a repeatable process for finding business opportunities over and over again, and who doesn't, I recommend starting with this little essay by Amy Hoy. Good stuff.)
Sketching with CSS is born
You don't have to write software to solve someone's problem. There are other kinds of products. Sketching with CSS is a book/video/info product. Software is what I do, so it felt weird to me to start a company and not write software. But given all my past failures, I wanted to do something small that I could finish quickly.
Once I decided on my customers (web designers), their pain (the frustrations of designing in the browser), and a solution (an ebook with videos), I created a landing page and started growing my email list.
Lesson #3: Turns out entrepreneurship is a grind
I put my new landing page on the web_design subreddit, and I got 15 email addresses. Four of them might have been my mom using fake email addresses to make me feel better. Ouch.
I'm much better at growing my list now, but there is still never a magic moment when everything becomes easy. I'll spend a day writing a blog post like this and usually net a couple hundred email addresses. It's better than 15, but man, would my life be better if it was 10,000. I've given up on that ever happening, though. As it turns out, entrepreneurship is a grind.
I now have over 3,000 people on my mailing list, a far cry from 15. How did I do it?
This is where all the research I did paid off. First, I uncovered many great blog post ideas as I was reading articles and comment threads, so I have a pretty big list of ideas. Also as a result of my research, I know where web designers spend time. All I do is pick a topic from my list, write a really good blog post, and then share it in all the places where I know my customers will be.
I also put an email signup form at the bottom of every post.
Write a blog post, and promote it everywhere. I did that over and over and over and over again.
A few tactics for growing your list
You don't have to write blog posts if you don't want to. The most successful thing I did for growing my mailing list was the Ultimate Flexbox Cheat Sheet.
Give away a chapter. I did that and snagged 500 email addresses.
Write guest posts. I wrote one big guest post for Smashing Magazine, and it resulted in another 500 email addresses. I plan to guest post more this year.
Add a sweetener. Give something away for free in exchange for an email address. I give away an interactive video course all about flexbox. People love the course, and the email forms convert well. I use Nathan Barry's ConvertKit to deliver the course and then move those emails over to MailChimp from time to time.
Lesson #4: Start small ... then go even smaller.
I underestimated the amount of work it would take to write a book and create hours of screencasts, all while writing blog posts to grow my email list. I am not a fast writer. If you can crank out a blog post in an hour or two instead of the day it takes me, you will finish much more quickly than I did.
I wrote and promoted for 6 months, which is a far cry from, say, Nathan Barry's usual turnaround time of 3 months. Structuring and prioritizing your time are skills, and apparently years of corporate dronehood had atrophied these particular skills for me. Plus, did I mention that I'm slow at writing?
But my excuses don't matter. Instead, the takeaway for you should be to start with an even smaller project than Sketching with CSS. Maybe you are good at structuring and prioritizing your time, but chances are you will run into another skill bottleneck.
Product scope is like a multiplier for all of your faults, so pick something small.
Lesson #5: Launching is an art form
There is an art to launching a product, and I do not have it. Fortunately, it is a skill that can be learned, and I am learning. If you haven't launched a product before, you are probably also bad at launches. This is all the more reason to make a small product.
I launched Sketching with CSS twice. For the first launch, I announced pre-orders to a list of about 1,000. The second launch happened when the book was finished, and I launched to 3,111 people.
On the first launch, I made about $5,000 in two days. Since the second launch was to a list three times as big, I expected to make about twice as much (factoring in that some people on the list had already pre-ordered). Instead, I only made another $5,000. I had clearly messed up my launch.
After chatting with Amy Hoy on Skype about it, I learned that I had failed to build anticipation for the product. For the second launch, I sent five emails over the course of five days. The emails were essentially no different than my blog posts. They were useful and on topics relevant to my audience. My email list loved them. But the problem was that I failed to tie the emails back to my product. I barely mentioned Sketching with CSS until the last email, so I failed to build anticipation. Oops.
Fortunately, I can launch again. I'll fix it the next time around.
Lesson #6: You probably don't know what you are doing
My launch failure highlights one important lesson I've learned: Entrepreneurship is a skill. If you've never left the "build cool product" phase of building a business, then you don't have entrepreneurial skills. This is why I think it's crazy to start off with a huge software product that takes months to create, especially if you don't know your customers yet.
Launching is a skill. Promotion is a skill. Writing for your audience is a skill. Learning about your customers is a skill. Empathy is a skill. Structuring and prioritizing your time are skills.
You're probably not great at all these skills. Start small, so you can learn as you grow your business.
One more thing: charge more
You should charge for the value of your product. For example, my price points are $39, $99, and $249. A $7 ebook is a legit way to make money and build an audience, but if you're in it to learn, you'll learn more if you charge based on value.
Let me explain. It takes guts to charge $249 for an info product. And because it's so scary, unless you are a fool, you will absolutely do your research and make something worth the price. For me, the price forced me to know my customers' pains inside and out.
There's yet another lesson to learn from charging more. Even when you know it's worth it, even when you know your customers inside and out, it's still scary to charge real money for your product. You have to learn how to get over it. Don't avoid it, don't be a wimp, and charge real money. Charge for the actual value of your product, and don't undersell yourself.
You may be thinking asking for money for something is no big deal, piece of cake, not scary at all — talk to me when you've actually done it.
Oh, and the more you charge, the better your customers will be. I love my customers.
Onward and upward
Since I've started charging for a product I'm selling on the internet, I've been making about $4,000 a month. Not bad! But not good enough, either.
If I can pull this off even after screwing up two launches, picking too big of a first product, and choosing an audience I have a hard time relating to, you can do it, too.
If you're looking for more entrepreneurial posts like this, you might be interested in how patio11 redesigned my landing page.
You can also drop your email in the form below for my business updates.