Jonathan Berkowitz

Jonathan Berkowitz

Marc Eglon

As well as enearthing the most amazing newsletters, we want to showcase the publishers and get inside the mind of the individuals who do the painstaking work week-in week-out. And celebrate those who bring the hell-yeah back to your inbox.

I’m on a mission to connect newsletter publishers with their 1,000 True Fans. I love to uncover the little-known fledgling newsletters from indie publishers, as well as the internet-famous ones you probably already know about. For issue 3, I spoke with Jonathan Berkowitz, publisher of the Random Roundup newsletter, about commonplace books, Cards Against Humanity, and being an entrepreneur in South Africa.

Tell me about you. Where are you? Where did you grow up?

I’m a 24 year old digital-native from Johannesburg trying to make a dent in the universe.

I’m most interested in tech, futurism, cool sh*t, startups+VC and service to humanity.

I try to play in the intersection between them.

I’m a marketing and growth specialist by trade – although the line between work and play is pretty blurred.

The thing that brings home the bacon (don’t tell my rabbi) is my startup Captain Calm.

The things that keep me away from my girlfriend are my podcast Emerge, trying to build a passive income, my blog, co-ordinating Cards Against Humanity: South Africa, and my weekly newsletter The Random Roundup.

I hope to one day take all the above and translate the experience, connections and capital they yield into a career as a Venture Capitalist.

I’m somewhat obsessed with self-optimization and living a life of adventure. These two things inspire and encourage me to achieve all the above.

What’s your big idea? your world view?

Using technology to more effectively and efficiently educate the world.

What are you working on?

My main focus is my startup Captain Calm. Our app teaches the tools & techniques of Cognitive Behavioural Coaching as superpowers (in an animated superhero world) to help children solve their problems and unleash their full potential. I find Captain Calm helps make the positive impact through technology and education that I so believe in.

My side projects are:
Emerge Podcast – 20-30 minute interviews with the Top Tech Founders and Venture Capitalists from Emerging Markets. I find it’s a great way to learn about VC and help expose the budding (and often thriving) startup ecosystems that so many of us are guilty of overlooking. I’ll be releasing an episode every month and look forward to broadening my knowledge, network and giving as much value to my listeners.

My blog ( – The idea here is to build a community of like-minded people around my interests and ideas. I’m a big believer in putting oneself in the way of serendipity and welcome anything that may come of it.

My newsletter – The Random Roundup – Where I curate the best 5-7 things I found on the internet that week – usually along the lines of tech, futurism, startups, self-optimization and cool things.

Cards Against Humanity: South Africa – I am crowd-creating the South African version of the popular party game. This is a passion project and just something nice to unite South Africans through humour.

I am also working hard on my mental and physical health by prioritizing exercise, meditation and making sure I get at least 8 hours sleep every night.

How does that work with Cards Against Humanity? Have you worked out some kind of licensing deal?

CAH uses a Creative Commons license which means we are free to adapt and share the game as long as we don’t sell or make money from it. We must also provide appropriate attribution and share it under the same Creative Commons License.

What’s your thought process behind working on so many ideas at once? Any tools or workflows you use to manage all your projects?

If I had an idea in the past, I would likely go headfirst into building an MVP with little concern for the workload it would bring down the line. One or two of my current projects are a result of this.

But since growing up a bit, I now only start projects that fit within the master plan. Cost-benefit and all that…

For all the ideas I have but don’t pursue? I simply type them out for release under the #StealThisIdea category of my blog and move on with my life!

I use Trello to keep track of all my long term goals for each project. I then use my notebook to help me break those down into monthly, weekly and eventually daily goals.

Calculating the amount of time each project needs per week and then strictly managing my time in order to devote the required hours to each has been the most transformative tactic and is the reason I’m able to work on so many things at once.

Why did you start the Random Roundup newsletter? Where does it fit into your masterplan?

It all started during an existential crisis. (I tended to have quite a few of those before finding my way.)

On that particular day, I tried to visualize how my ideal life looked and how best I could contribute to the world.

Without exception, in each and every scenario imaginable, I stood to benefit from having a personal audience I could share myself, my ideas and my projects with.

Step 1 – discovering that I needed to build an audience. Easy enough.
Step 2 – actually building an audience. Not quite as easy.

As a self proclaimed internet hitch-hiker, I was coming across all sorts of interesting and cool stuff every week. Until I had some valuable things of my own, I thought I’d start out sharing those instead.

I would call the newsletter “The Random Roundup” and fortunately, people really loved it.

Right now, the Random Roundup is a collection of the best 5-7 things I found on the internet that week – usually along the lines of tech, startups & vc, generally cool & interesting things, self-optimization and things that make you go “woah” (and sometimes “lol” too).

As for the future of The Random Roundup? Who knows… but I’m damn excited to find out.

What’s your newsletter production process? Where do you unearth your content?

As and when I see something online, on my social feeds or something interesting is sent to me via other newsletters or my own lovely subscribers, I add it to either my chrome bookmarks bar or Instapaper. There they sit until Saturday afternoon, when I begin sifting through all the links to decide which I’ll include in the Roundup.

It is at this point that my need for covering all bases takes over and I head over to aggregation sites such as Hacker News and Reddit.

Once I have the final 5-7 links for that edition, I list them all out in Evernote and begin the process of writing the blurb that accompanies each link.

This is by far the most time consuming part of the process as I spend longer than I’d like to admit trying find the balance between insightful, enticing and witty. Most times I miss with all three!

I use Grammarly to fix any typos and catch any stray commas before copying it all across to TinyLetter where I add the hyperlinks, fix the formatting and send it off.

Any indispensable tools, apps, software, notebooks, hardware etc that you use?

For Delivery:
Contrary to most of the newsletters on Letterlist who use MailChimp, I use TinyLetter to deliver my newsletter. I find it’s simplicity a pleasure, besides some inexplicable formatting rules.

For Publicity:
My own Social Channels, Slack groups and Medium (where I cross-post each edition).

For bringing it all together:

For not making a fool of myself:

And, of course, my Mac.

What keeps you up at night?

Absolutely nothing. I sleep like a baby and it’s not just because of my Tempur mattress!

I try not to worry too much about things that are outside of my control. To let those same things affect my sleep? Madness.

Since being immersed in the world of Cognitive Behavioral Therapy and Stoicism (by extension) through our work at Captain Calm, I’ve learned from many of the lessons we teach in our educational comics.

It’s all about reframing your thoughts and perceptions. I try to control the things that I can control and try not to worry about the things that I can’t.

Imagine you have no audience, no network, no assets apart from your knowledge – How would you start from scratch?

The funny thing is that I feel I currently am at that stage.

My audience is still very small, my network largely confined to South Africa and physical assets inconsequential. Hell, I don’t even have that much knowledge!

I am building all that I want from scratch.

So the question really is, what am I building and how am I doing so?

I want to be location independent and financially free. I want to never worry about making money but instead on making a positive impact on the world and the people in it.

As for how? Well, that’s the fun part.

What big question did I miss that I should have asked you? What’s your answer?

2 things:

“What is the next itch you want to scratch?”

The idea of a commonplace book fascinates me.

A commonplace book is basically a central resource or depository for ideas, quotes, anecdotes, observations and information you come across during your life and didactic pursuits. The purpose of the book is to record and organize these gems for later use in your life, in your business, in your writing, speaking or whatever it is that you do.

The best part? Some of the world greats such as Marcus Aurelius, Montaigne, Thomas Jefferson, Napoleon and Bill Gates swear by the practice. The benefits include wisdom, mastery and weaving together a latticework of ideas for deeper understanding, insight and connection between ideas. That’s one hell of a testimonial.

I believe our world is one of overconsumption. Take the internet for example – the average person’s ratio of consumption-production is totally out of whack.

It is my wish that people produce more than they consume – in all aspects of their lives.

Although there’s not much I can do about that, one thing I am able to do is teach people the commonplace book method to produce while they consume.

I’ll be going headfirst into mastering my own commonplace book practice so I can take my learnings into either teaching people to keep their own or create a tech solution for doing so – or both!

“What are you most proud of so far”

Not one person has unsubscribed from the newsletter.

The handful of glowing reviews of the newsletter. Those are always great to get.

The average open rate is above 65% – well over the industry standard.

People are finding The Random Roundup organically and it is growing at steady rate week on week.

The high click through rates mean people are finding value in the things I share.

Where can our readers reach out to you? Social profiles?

I’m always up for grabbing a coffee but being on the tip of Africa makes doing so difficult for most people.

So feel free to reach out either on Twitter, Instagram or Facebook… if you’re my mom.

Email ( is a pretty good bet too, as is subscribing to The Random Roundup – where you’ll not only make my day but you’ll also stand the best chance of getting a reply.

To be honest, I’m pretty useless everywhere else.

What’s the tech/startup scene like in SA? It’s not a place I hear a lot about.

I love this question and feel well equipped to answer not only from my personal experience as a South African entrepreneur but also from the lessons I’ve learned interviewing two South African investors on the Emerge Podcast.

There is no shortage of capital available for promising startups from VC funds, government grants and angel investors, corporates and individuals. The shortage is of startups scaling at any significant pace to make such an investment attractive.

The reason for this is not due to a lack of innovation or driven people. The problem comes in where these same people don’t have the execution skills to take their idea and turn it into a thriving startup and later a big business hiring hundreds of people – which is what South Africa desperately needs at the end of the day.

The solution many people see to this problem is to get more mentors and advisors to promising entrepreneurs or into early stage startups.

Having said that, we do already have a great ecosystem with some pretty big startups hailing from South Africa. We are the biggest startup player in Africa and are seen as a gateway into Africa. Things are pretty exciting down here!