2019 was all about blocking out big chunks of my calendar to prepare my coverholder application for my binder. We’re heading in the right direction and have started 2020 by kicking off the development of the quote and bind system (I realise this isn’t exciting to anybody but me!). Beyond that, 2019 was a good year for business growth, a bit of travel and a change of scenery…


I kickstarted the year by speaking at New Adventures in Nottingham. This was a fairly last minute arrangement so I didn’t have time to write a talk specifically for it.

Speaking at New Adventures Conf

I’d bought a ticket as an attendee, but I couldn’t pass up the opportunity to speak when Colly and Geri asked me a fortnight before. New Adventures has shaped my career and played a big part in what I’m doing now, which is why it was one of my most nerve-wracking speaking experiences.

With my first speaking gig of the year out of the way, I travelled to London to meet with the insurer I work with. My confidence was growing at this point so I felt more comfortable asking for changes I had been thinking about the year previously.

  • lowering the excess
  • adding two new products
  • building the quote and bind system

It was a successful meeting, but I am still waiting for some of the changes coming to fruition. This is because my application to build the quote and bind system is still being processed (more on that later).


In February I launched a new product called legal expenses.

We launched a new insurance product

I’ve written about the disappointing product launch already. I don’t feel as downbeat as I did when writing that post as more customers are adding legal expenses to their policy and people are starting to use it (particularly the late payment service).

However, the launch didn’t live up to the expectations I’d set myself. I thought this would inch me towards product / market fit (yes, I still feel like I haven’t reached product / market fit!) and the uptake would be higher than it was. Whilst the adoption rate has improved, I feel there’s something missing from the business. This product wasn’t the missing piece of the jigsaw that I thought it would be.

In my 2018 year in review, one of my goals for the year ahead was to launch 3 products. Legal expenses ended up being my only product launch of the year.


My friends, Ayden and Pete, eloped to the Scottish Highlands. This was a chance to pick up my camera again and photograph the elopement. Shooting in gale force winds and rain on the beach reminded me why I’d given up my career as a wedding photographer, but we had a blast. One of the most memorable weekends of my year.

Ayden and Pete getting married

Mid-way through the month I travelled to Manchester to speak at Before UpFront. This was an informal evening meet-up prior to the conference, so my talk was a lot more personal and focused on my journey.

Whilst in Manchester I reached a significant milestone; I had sold £200,000 of insurance through With Jack’s website. I’d go on to sell another £150,000 by the end of the year.

I only started experimenting with paid marketing at the end of 2019. However, in March I had my first stall at an event. It was a photography workshop / conference and I consider it a success.

I think the reason my stall performed well was because it was an approachable environment where people could ask me questions. It was an intimate event with a good community vibe. I didn’t have any competition (there were no other ‘insurance people’), so photographers opened up to me about their problems. Having a background as a wedding photographer also helped.

With Jack's stand at Photography Farm


At the beginning of April I travelled to Rome with a group of friends from Uist. This was my favourite trip of the year. Shawshank’s brother is a priest in Rome, so he took us sightseeing and to his favourite restaurants.


Whilst in Rome I had the busiest week ever at With Jack. It did make it difficult to relax and enjoy the trip, but I’m still at a stage where I can’t separate my personal life from the business (no employees and still manually processing policies). I’m not complaining—it’s a joy to travel and earn a living, but maybe in 2020 I’ll have my first proper holiday?

The busy week paid off because I ended up having my first £20,000 month in April!


I travelled to Frankfurt to speak at FemtoConf in Darmstadt. FemtoConf is pitched as a “super tiny conference for small, self-funded, software companies”.

I loved the intimate format and would recommend it to any bootstrapper, but my highlight was the 5AM photo walk I did with Christoph, one of the organisers.

Sunrise walk at Femto


I attended a family wedding in Cyprus. The highlight was visiting the ghost town, Famagusta. Again, I was still working for much of this trip. This is the way things have to be whilst I’m manually processing policies and running a company of one.

A few days after returning from Cyprus (which was all-inclusive!) I did Tough Mudder. I trained hard for this, hiring a personal trainer to help me work on my upper body strength—which is a weakness—and focusing on losing kilos to make the monkey bars easier. But the all-inclusive holiday kicked my ass!

Tough Mudder

I struggled for the first two miles until we hit the Arctic Enema obstacle, which is where you plunge into minus degree water. I’ve never experienced my body going into shock before. It’s something I’d only do once, but the shock of the freezing water gave me a shot of adrenaline and helped me get over the finish line.

Tough Mudder was another highlight of the year. Not because of the achievement itself, but the friends I accomplished it with—Simon, Gregg and Suzie.


At this point I decided to block out the remaining calendar year to focus on my binder. This meant saying no to travel, speaking gigs and anything else that eats into my time.

The year got a little quieter at this point, but the highlight of 2019 was getting the keys to our new office! After working from home for 6 months, I moved into a space with the same friends I completed Tough Mudder with.

Our new office

It’s a 10 minute walk from my house. It’s a converted warehouse. Indie, my dog, is allowed in the building. We’re on the top floor, so we have access to the rooftop terrace. It’s pretty great.

The space is called Two Ten Co and we have desk space available, if you’re interested.


This month saw me visit Nottingham for a product sprint workshop with Scott. I’ve been working with Scott on With Jack’s design and development for a while. We fleshed out what we’ll be building next and gave my roadmap much needed direction.

Working on With Jack's roadmap

Towards the end of the month I had a fleeting visit to London to speak at Design x Business about insurance. This is a meet-up organised by one of my customers, so I like to support it in any way possible whether that’s sponsoring or speaking at it.


September was quiet as I had my head down focusing on completing the bulk of my coverholder application. All of this work will enable me to build a quote and bind system.


I dusted off my camera again and shot my sister’s new range of dresses on Fingal, a 5 star floating hotel in Edinburgh. I’m pleased with how the images turned out and remembered how much I enjoy photography. I say it every year, but I hope to take more photos in 2020.

I spoke at my last event of the year, a local meet-up called GAB. I’ve attended the GAB events for years, so it was humbling to be invited to speak at one. Unfortunately it wasn’t under the best circumstances. I’d attended the funeral of an 18-year-old family member earlier that day and wasn’t in the headspace to do a talk. It probably wasn’t one of my best and I was glad when it was over.


After weightlifting for several years I sustained my first injury—a twisted pelvis. It left me bed bound for days as the pain was too severe to move. I couldn’t move my neck or legs.

Fortunately the physio was able to help me, but it’s definitely set my training back. I was deadlifting 90KG comfortably and I’m now struggling to lift 30KG. It’s also affected my confidence as I’m afraid of the injury reoccuring, but I’m working on building my strength back up. A lifetime of sitting at computers has taken its toll on my back.

November wasn’t a great month in general. I took Indie to the vet hospital one evening and was told she might not make it through the night. The vet gave me some alone time with her to say goodbye whilst I left her overnight on a drip. I’m so happy she pulled through and is doing well.

I reached another milestone in the business as I celebrated my first full year directly authorised! I wish I’d done this sooner because the business has grown, I’m offering my customers better support and I’m making more money that I can reinvest back into the business.

There is more responsibility and weight on your shoulders when directly authorised, but it’s a worthy trade-off.


December is always a quiet month. A lot of freelancers take time off, so I get a bit of breathing room to focus on projects I usually don’t have the time to do.

I Launched ‘Unsure? Insure!’, which is a podcast (and soon-to-be video series) about insurance. These are short episodes demystifying insurance and explaining how it works for freelancers.

Unsure? Insure! 

And that’s a wrap for 2019!

Video Games I Played

  • Hitman 2
  • Ni No Kuni 2
  • Horizon Zero Dawn
  • Days Gone
  • The Outer Worlds (currently playing)

Business Books I Read

I got into fiction in 2019, so I didn’t read as many business books.

  • Zero to one
  • The Messy Middle
  • Chasing Excellence (this is a sport book, but I think a lot of the principles apply to business)

Last year I sold £100,000 of insurance through With Jack’s website. This year I doubled that.

I’m really happy with this year overall. Before writing this post I felt like I hadn’t achieved much, but a new office, a handful of speaking gigs, a few trips under my belt and doubling With Jack’s sales is pretty good!

Going forward I’d like to:

  • eat less meat
  • pick up a musical instrument
  • launch the quote and bind system