4 Years at Castos – and Why It Was Time to Leave.

This year marks my 4th working at Castos on our podcast hosting, analytics, productions platform and Seriously Simple Podcasting, our podcasting plugin for WordPress.

Today also happens to be the last.

Looking back

Craig Hewitt, founder, and CEO of Castos, first contacted me on December 27, 2016. He let me know he’d recently purchased the Seriously Simple Podcasting plugin from my friend Hugh. He also mentioned that he was wanting to build a podcast hosting SaaS application to support the plugin. At the time, I was on vacation, and we agreed to chat when I got back.

I treated Craig like any other freelance client; I invited him to post a project through the Codeable platform. We started our first project discussions on Jan 9, 2017.

The first plugin update we pushed out to Seriously Simple Podcasting was version 1.15.2 on April 19, 2017, which only included adding support for certain iTunes fields in the RSS feed and a filter for the post meta key that stores the audio file URL. However, in the background, we were feverishly working towards version 1 of Craig’s podcast hosting SaaS idea.

On Apr 6, 2017, Seriously Simple Hosting went live at Only one capture for that URL exists on the Internet Archive because it was renamed to Castos soon afterwards. A little known fact of that first version was that Craig, an admitted non-technical person, built all the front end you see on that home page!

On June 01, 2017, Craig and I switched to an ongoing, part-time contractor agreement. Along the way, the team grew to include a second Laravel developer, Danilo, a Customer Support Specialist, Eileen, and our Analytics Engineer, Stefan.

At the end of 2018, I switched from spending a smaller percentage of my time on Castos to spending quite a large portion of my time working on the project. The business was accepted into the first cohort of the TinySeed accelerator, and we added a Growth Marketing Specialist, Denise, to grow our customer numbers. By the time Craig, Danilo, and I met in person in June 2019 at WordCamp EU in Berlin, we were a team of 6 and growing rapidly.

I consider myself extremely fortunate that when the global pandemic hit in 2020, Castos continued to thrive and grow. During that time, we welcomed our new Director of Podcast Success, Matt, bid farewell to Denise, welcomed Becky from Craig’s other business, Podcastmotor, which merged into Castos as Castos Productions, and were joined by Kim on Customer Support, Dennis in Marketing, and Alec and Sergey as our newest Laravel and WordPress developers respectfully.

I recently reached out to my social media community, to see how many folks I know use our products. The response was humbling.

Coming to a fork in the road

During the latter half of 2020, Craig and I started having some discussions about my role in the company and where he saw it going in the future, with the development team’s growth.

Those discussions made me stop and take a critical look at my professional career and whether I really wanted to keep going down this path.

It reminded me of a poem I’d once had to memorise when I was younger called “The Road Not Taken” by Robert Frost. I was about 12 or so, and I took part in our local poetry Eisteddfod, reciting this poem. For whatever reason, the words have stuck with me since then.

As I thought about my future, I recalled the final stanza, and the words seemed apt to my situation.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less travelled by,
And that has made all the difference.

Robert Frost

Asking Why

About six months before I started working with Craig on Castos, I wrote a blog post, mostly for myself, as a reminder of why I’d chosen the current path I was on. At the time, I wrote these words:

The honest truth is that I shouldn’t be working as a freelancer. I should be working for a company, where I am simply a small cog in a bigger machine.

Remembering ‘Why?’ – July 15, 2016

As I took a look back at the last 4 years with Castos and the 12 odd years of software development before that, I found myself re-reading that post and asking myself why again. Surprisingly, the answer I got was very different from what it was before.

In that same post I had said the following:

I became a software developer for the simple reason that I like writing, be it code, a technical document or a tutorial or a blog post. I’m not what I would call a ‘creative’, I can’t draw or design something to save my life. What I can do is develop software that solves a specific problem or write an article or tutorial that helps someone achieve a specific task.

Remembering ‘Why?’ – July 15, 2016

And as I read it, I realized that that statement had changed. I no longer wanted to write code for a living. I no longer wanted to develop software to solve someone’s specific problem. I’d reached a point where I wasn’t enjoying the process of software development anymore. After 16 years of building software, I desperately needed to do something else.

The realisation that I was not enjoying the well-known path anymore, coupled with the fact that my future was looking very much tied into that path, made me stop and consider whether this was the road I wanted to stay on.

As it turns out, the answer was, no.

Now what?

During this process of self-realisation, I took the 16 Personalities Test. As I read it, I discovered that how I felt about my future as a developer had a lot to do with my personality. The frustrations I experienced were less because of the people/product I was working with and more about the actual work. I understood what I probably should be doing, and the path in front of me was very different. It was time to take a chance and see if it would be possible to make a change now or continue down a path that might not work out for the best in the future.

And so today, I leave my position as Lead Developer at Castos to take on an exciting, but also scary, new journey. I will be taking off my developer cap and putting on another one. It’s a path that will challenge me in interesting, new ways. It will promote new learning and growth. Finally, it is a path that I feel is more in-line with my personality and able to do my best work.

I’m taking the road less travelled by, and I believe it will make all the difference.






10 responses to “4 Years at Castos – and Why It Was Time to Leave.”

  1. Dwain Maralack Avatar

    This is fine example of bravery. Hats off to you and Godspeed on your new Journey.

    1. Jonathan Avatar

      Thank you my friend.

  2. Maciek Palmowski Avatar

    I always thought that I will be developing for yet another few years. But I have just become an ambassador for one company. Surprisingly I love my new job. I spend more time talking with other people, speaking publicly.

    So I wish you, that you’ll find as much happiness in your new job as I did.

    1. Jonathan Avatar

      Thank you Maciek, it’s great to hear that you are also now doing something you love.

  3. Trisha Cornelius Avatar

    Congratulations Jon.

    I look forward to hearing all about the new adventures and I am glad that you are being true to the self that you have become.

    1. Jonathan Avatar

      Thanks Trish. It’s a weird thing to realise this with age/experience/maybe even some wisdom.

  4. Justin Avatar

    Good luck on your new path. Sometimes, it’s best to take a step back and ask yourself whether you need to go in a different direction.

    1. Jonathan Avatar

      Thanks Justin. The step back took me almost a year, but I have a good feeling about the new direction.

  5. Paul Edward Avatar

    Good luck on your new path, I look forward to read more about your new adventure. Hope to speak to you soon.

    1. Jonathan Avatar

      Thanks Paul

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