Okay, so I did a written interview for a reasonably well known publication...but, they didn't end up featuring me (ahh well..). So, I thought - hey, why let this go to waste?

Here's the interview telling my story so far. Enjoy!

Hello! Who are you and what business did you start?

Hi, my name’s Rob! I’m a chartered accountant, and I make stuff on the internet. I started Pickle Rooms in my spare time, back in January 2024.

Pickle Rooms is a newsletter for startups and entrepreneurs, where I share cool stories about people making money, and try to explain how they did it.

Whilst I’m currently pre-revenue (this isn't true, I actually had a very tiny bit of revenue, but I'm pretty lazy and couldn't be bothered explaining - keep it simple eh!), I’ve managed to get over 474,000 views on reddit within 2 months of starting to post, and now have 1,300+ people reading the newsletter each week…wahey!

For future revenue, I’m currently building out a number of digital products to sell. I expect this to be the main revenue source (only for the near future), alongside sponsored ads in the newsletter.

What's your backstory and how did you come up with the idea?

So Pickle Rooms isn’t my first startup, it’s actually my 3rd.

My first one was a print on demand company, which pivoted into doing music events. These went better than I expected (despite knowing next to nothing about marketing back then), I got 150 people to both of my first 2 events, but I realized events are quite stressful & unreliable, so I thought it best to try something else.

I then started an E-commerce company in the home & garden retail niche, which got to around £50,000 in annual revenue.

I tried to scale it, by putting it in a 3PL (third party logistics warehouse) who would fulfill all my orders, but I managed to get De Quervain tenosynovitis in my hands…

I couldn't type for like 4-5 months, and my ROAS (return on ad spend) halved after I’d committed to scaling. I couldn’t do anything to try and recover it, it was a nightmare!

Eventually this meant I had to close the company, and let my hands recover.

After this, I had a fair bit of time to think. I knew I was going to start something else, but I didn’t know what.

So I spent ages researching various models (things like VR podcasts, and a birthday reminder SaaS ideas), but having stumbled on email newsletters, I dug deeper, and felt the model was awesome.

A big part of the challenge of my previous e-commerce company was it was limited by capital, and orders which needed to be fulfilled. By starting a newsletter, I could spend all my time on marketing, didn’t need much money, and could sell products digitally, which didn’t need to be fulfilled. A great fit.

I also made sure I knew every benchmark I needed to hit, open rates, click through rates, lifetime value of customers, cost of acquisition etc. I felt good about this one.

Take us through the process of building the first version of your product.

I first started laying the groundwork for the branding, and began the SEO (search engine optimisation). I made the website on Shopify, and began writing articles, that I could then link to as content in the newsletter.

For the newsletter, I figured out the design I wanted and then started creating an automation, to send it out automatically. This meant I made about 15 newsletters which would go to people when they signed up.

The idea was so that I didn’t have to write a newsletter every week, and could get a bit of data about which emails worked best. Like a chess algorithm, I’d then be able put the best ones first in the sequence, and use that as my welcome sequence.

I knew I’d need to send way over 50 newsletters to get even close to my lifetime value, but the idea was simply to understand what the readers liked at this stage.

Describe the process of launching the business.

For funding, I was using my monthly salary to cover the costs for launching the website and other software that I needed.

In terms of launching, I didn’t do a hard launch, since I knew there wasn’t much for people to consume, and I needed to test and iterate as quickly as possible. I also knew that it would take time for my articles to rank on google, so I launched as soon as my first article was ready. 

Here’s a picture of what the 1st version of the website looked like. It’s improved a lot since then….

Since launch, what has worked to attract and retain customers?

Before launching, I’d planned multiple ways that I could get subscribers. They have actually worked out more or less as I’d planned, although the reddit channel was both better and worse than I expected! Here’s the list that I’ve been implementing:

• SEO (search engine optimization)
• Reddit & Hacker News
• Twitter paid ads
• Advertising in other newsletters

Seo

So this was the foundation I’d planned to build upon. I knew it would take me 6-12 months to rank the website, so it’s a slow burner for me.

I knew that by writing articles and attracting backlinks, I’d eventually get some form of stable traffic. Here’s what that currently looks like:

Reddit & Hacker News

My first post got 71,000 views, I was staggered. It was a post about how I did £30,00 in the first year of my E-Commerce business.

I was pretty stoked….could I replicate the success? The answer, yes.

After a couple of duds, I managed to do one that got 253,000 views a few days later.

The strategies I did which worked were:

• Stories from my past - they had to be juicy, and well written.
• Inciting engagement - asking people a question, and getting them to share their juicy stories in the comments.

One thing that was somewhat key was replying very quickly to any comments. This got more engagement to the posts, which helped them get more views.

The sad thing was, that 474,000 views only resulted in less than 100 signups to the newsletter. This was mainly due to the fact I hadn’t set up my landing pages at that time, and hadn’t done any conversion rate optimisation.

Twitter paid ads

These worked okay. 

I made a lead magnet (a report on e-commerce benchmarks) and set up maybe 20 ads with different variations pointing to landing pages, to test which ones win. I spent initially around £200, got a few signups, but during this time I’d also started advertising in other newsletters, which seemed to be a better bet….

Advertising in other newsletters

So this has driven most of the growth so far, and at a cost of acquisition that I’m happy with for the long term.

I’m currently acquiring subscribers for $1.50 advertising in Refind, and $2.50 advertising on the Beehiiv referral network. Whether this seems a lot to you or not, I’m quite happy with it, as (from what I hear) a lot of the larger newsletters seem to acquire subscribers at a similar price. 

So the main thing I now need to do is work on getting the lifetime value of the customer up, as I think I’ve solved the acquisition side of the story (to some extent).

How are you doing today and what does the future look like?

So my goal for the future is simple, get my lifetime value per subscriber above the cost of acquisition, and hopefully get it to 3-6x times that. I’d also like to see my payback period get to less than half a year (or 90 days if possible!).

Once I’ve got that, I intend to dump the “money truck” onto the ads…let’s see if I can get there!

Anyway, here’s how I’m planning on doing it:

• In the signup flow use co-registration to refer subscribers to other newsletters, and get a kickback when they signup.
• Sell a digital product (a front-end offer) in my welcome series, for between £30-£80.
• Then run ads in each newsletter.
• Have multiple publications which I can refer my subscribers to.

Hopefully all these will increase my lifetime value, to the point I can reverse that money truck up…

Through starting the business, have you learned anything particularly helpful or advantageous?

I’ve learnt more and more about the newsletter industry. Whilst my strategy is still the same since I started, it’s taking longer than I thought to get advertisers on board. From what I hear, it tends to be once I hit the 5,000 subscribers mark that I should get more opportunities.

I’ve also learnt more that the products I’ll need to add are very important. From listening to podcasts, I hear that some products can work 10x better than others, so I’ll need to test test test!

What platform/tools do you use for your business?

I use Shopify to host my website, to make it easy to sell the digital products. I used this in my previous E-commerce Business, and so this felt natural - I was very familiar with it’s functionality.

I use Beehiiv for my ESP (email sending provider). Beehiiv is a startup that’s growing very quickly due to a few core features, which I intend to rely on. The features are the Beehiiv referral network, primarily for both getting subscribers, and making co-registration revenue, alongside the referral program, which I’m hoping will make it easy for my readers to share the newsletter organically.

I then use Zapier to fill in the gaps - things like aligning the email list between Shopify and Beehiiv.

Advice for other entrepreneurs who want to get started or are just starting out?

I can mainly speak from past failures for this topic ha! The main thing I didn’t know when I was doing the E-commerce business was to focus on the Lifetime Value and cohort analysis, as opposed to just simply whether I made profit on my first sale or not. This is because a fair number of E-commerce companies might only break-even or make a small loss on the first sale, and then make most of the profit returning customers.

This is the reason I’m so focused on retention and lifetime value in the newsletter.

Are you looking to hire for certain positions right now?

At the minute, I’m not looking to make any hires, this is simply due to budget…I am bootstrapping after all! This may change if someone gets in touch to provide funding, but I’m quite happy taking the bootstrap route for the time being!