My Many Previous Site Failures And Lessons Learned

*This is a two part series following my post on how to start your own site. You can check out that part here!* 

Before I got to Digital Richard, there were lots of failures. Not saying DigitalRichard is 100% a success (let’s see in a year) but it’s my best iteration for sure. To save you the time of going through all the mistakes I did, let me just detail it out for you.

TLDR Version:

  1. You will fail a few times. This is stage everyone goes through but this is what makes you grow!
  2. WHEN YOU ARE READY put down the money and buy a domain/hosting like Bluehost which you can do here. Putting your own money down is game changing.
    #1 Having a site that says isn’t impressive at all
    #2 Free options without the right technical skills will get frustrating to make real edits
    #3 Putting money down instinctively makes you value this project more. Think about those crazy people that spend $100+/MONTH on gym memberships. Most do that to encourage themselves to workout otherwise they’re wasting a ton of cash.
  3. Plan your site before hand. Think about what the purpose of the site is. Try to stay in a niche but at the same time don’t be so niched that it’ll be impossible for you to expand into other things. Also think about the design. If you are trying to write a blog or an online store, draw the whole site on paper. Think about how it would look. Use other sites as examples. If you are starting a blog, have some posts written up before hand. The work you do before hand will make your life a lot easier in the long run!
  4. Commit to a plan. This is one of the hardest things that even I struggle with. For the first few months or maybe even for the first year you might not see any results in terms of visitors but still you have to persevere with the end goal in mind. My plan is on most weekdays I will put in 1-2 hours a night and on weekends I will try to put more time in, if I can. This way you continually learn and grow without it feeling to draining on yourself.

First Attempt:

Fun fact before Digital Richard I had a few different attempts at blogging. I told maybe 5 people about these early blogs and I stopped working on them mainly because I lost interest in it for a variety of reasons.

Without further ado look at the old Digital Richard here This was the very first time I tried doing anything website related, so naturally it is not great. I had no strategy or goal for the site, the picture on top isn’t the size I want, the whole blog isn’t mobile friendly, and it just looks bland. There’s even the test 123 post I never bothered removing.

So as you probably guessed this was done with the free tool from, and honestly I really didn’t like the free tool. It’s a great way for someone to get started with no investment needed, but it limits you heavily. For example, the free themes just weren’t what I was looking for and it was hard to edit things myself (also I had no knowledge of website building at the time). A few of these factors and being busy at the time caused me to not really find a passion for this site.

So in the end I scrapped it.

Second Attempt: Buying A Domain

After that last failure, I started reading more about starting blogs and monetization strategies and I wanted to try something completely different. My NEW grand plan was to make a site that discusses different hobbies and how to get started on them. I set up an Amazon affiliates account in the hopes that I would make money recommending things on for the hobbies I was discussing.

For a little context, throughout my life I’ve tried many things thanks to my caring parents who wanted me to try everything. Some random activities my parents made me do include ballet, bowling, roller skating, kendo (Japanese sword fighting), scuba diving, musical instruments, and many more. At the time of making this site, I was abroad in Singapore and just got into making cocktails and muay thai. I figured, hey I’ve done so many different “hobbies” why don’t I just write about them for the blog posts. So learning from my last attempt with, I decided to double down and actually buy a domain name The idea being I would recommend “starter kits” for people who are interested in new hobbies.

I hit a few challenges really fast.

  1. The site was WAY TOO GENERIC. I don’t recommend anyone starting with such a wide topic like “hobbies”. It makes writing content and planning the site a daunting task because of the sheer number of hobbies in the world.
  2. I didn’t know enough about most of the hobbies I’ve tried. This was another issue of being way too generic. While I tried a bunch of hobbies as a youngster, I didn’t actually know much in details except what my teachers taught me. This made it difficult to actually write about any topics as I would have to research any topic I wanted to write about.
  3. Technical/Aesthetic issues. So I thought paying for a domain name would magically solve all my issues with the free wordpress as last time. It didn’t. I ran into the same issues that all the free themes I was interested in just weren’t right for me. With your own domain you have more technical control to change what you want, but I had no background in HTML/CSS so unless I hired a web developed there was no way for me make in depth changes to these themes. DON’T UNDERESTIMATE THIS. At one point I had no idea how to format images properly and I was using html code to hard code at what pixels some images should be.

So in the end I scrapped it. I don’t even have any pictures of this as someone ended up buying my domain name once it expired, but low key I’m thankful for that. It was ugly.

Third Attempt: Unbounce

So after that last failure, I started getting into the agile startup crowd that believes in the idea that you can start a business with next to nothing. I’ll save the agile business model for another post but the easiest way I can explain it is as follows. Think about the traditional business where a big company comes up with this new product and then markets the shit out of it to get sales. Now think about a small entrepreneur who doesn’t have the resources like a big conglomerate. They can’t afford to create a product that will flop, so this is where the agile business model comes into play. What if instead of making something first, you sell something first? A great example of this is something like kickstarter. People sell you an idea, sometimes a proof of concept and they only go through with the business if they see significant demand (funding in the case of kick starter).

I wanted to try something like this and at the time I was starting to get more and more into cocktails. My biggest complaint with the hobby was that it’s pretty expensive to try new things. For example, I don’t need a bottle of a fancy expensive liquor that I probably will use in one or two drinks. Given at the time subscription box services were getting big I tried to make my own specifically for cocktail ingredients.

So with my grand plan in mind, I tried to follow the agile business model and build a site. For this I used Unbounce, these landing page builders do an amazing job in doing exactly that. Building landing pages. I created a basic site. I even hired a guy on fiver to make me a logo, which ended up being pretty dope. I was proud of what I ended up making in a few weekends of brainstorming after work.

This is an idea I might go back to one day, but I put it on hold for a few reasons.

  1. Once again, I didn’t have enough technical/design skills. Look at that ugly orange box. I didn’t know how to edit it enough to make it look exactly how I imagined it. The other big technical issue I ran into was setting up a payment system. I tried to use Stripe, but using an external tool like Unbounce, you don’t have that much control of the HTML/CSS files. I didn’t know how to set Stripe up properly so naturally I had no idea of how to actually sell anything. Of Course I probably could have bootstrapped another way like send people to a paypal link, but at the time I was pretty frustrated with the site’s looks and I lost motivation.
  2. Once again, I am not a real bartending expert. I think it showed when I just threw in buzz words everywhere like tantalizing bitters when the only bitter I’ve ever used was Angostura bitters (the most basic of cocktail bitters).
  3. I lost motivation. I can blame it on a ton of factors at the time like my long commute for my internship, and having no free time, but at the end of the day I didn’t care enough. I didn’t even want to take ownership of the product which is why I have stock photos of fake owners up there (Although I snuck in a fake Richard hehe). I think this is another important part of building a great site and also why I now have Richard in the name of this site.

Fourth Attempt: Actually Coding Myself

So after the last failure, it became pretty clear I needed to learn some coding myself. I signed up for an intro website design course at CMU that taught the bare minimums of HTML/CSS which was a great help to me. During that semester I learned of bootstrapping where you can use these awesome premade bootstrap designs to have a website running super quickly. The only caveat is that you have to do all the coding yourself. I decided to work with this bootstrap template as I thought it was the perfect for my online site.

Bootstrap Agency


The discerning reader might realize IT LOOKS EXACTLY LIKE MY CURRENT ONE. With a few differences in terms of the glaring yellow box and the pictures are more oval. This site was the O.G. precursor to DigitalRichard and was the main reason I chose to build my site like it is today.

So… what went wrong?

  1. TECHNICAL SKILLS UGH. So the coding aspect wasn’t too bad the real issue was actually hosting the site. If you use an easy system like wordpress, it’s basically like using Microsoft Word. Let’s get super meta and actually show you my screen writing this post. It’s really easy to write a post and I can save a draft and publish with the click of a button.With bootstrapping after your site is finished you have to transfer it to a hosting platform which I got my CS buddy Ahadu to help me with. The real problem was whenever I wanted to make one slight change. Let’s say I wanted to fix a typo. I would have to change it in the code then reupload it to the file transfer system. It got annoying really fast. So I got it to the point where it looked good enough and left it there.

Honestly speaking if you come from a technical background, I think bootstrapping is probably the best for you. You have complete control of the site and it’s easy to get running through the great templates already out there. For less technically savvy people like me, I think wordpress is the go to option.

Final Attempt (hopefully): DigitalRichard

Finally after lots of failed attempts, I decided to get serious with DigitalRichard. Looking back at all these past experiences, it’s clear I kept learning from all of them. Whether it be increasing my html/css knowledge, understanding how to set up websites, or taking ownership with my name on the site. Those past failures were vital to what the site is today.

My final tip is to have a plan for your site. I mentioned in my previous post, I don’t expect to make any money in this site for a year. My plan is for the next 2-3 months write posts/ research ways to grow the site. After I hit 20-30 quality posts, I’ll start marketing whether it be paid ads, social media, guest posting on other blogs. All of these things are long term but every hour I put in gets me an hour closer so it’s super exciting!