Last week I cleaned out my home office and found a post-it note from 2013. It was a scribble of the insurance company I wanted to build, forming the basis of what would eventually become With Jack.

My post-it note of the insurance company I wanted to build
  1. It needs to be human.
  2. It rewards loyal customers.
  3. The technology doesn’t suck.

I remember writing that note. I was working from Toad’s Caravan at the time and fed up of being in buy-to-let insurance.

That business impeded my creativity. While there were challenges in insurance I wanted to solve, I was itching to work on something that would allow me to be more, well, me.

This nostalgia ties in nicely with the fact it was a year ago today I launched With Jack!

Although I’d soft-launched a few weeks earlier to iron out kinks, I was now opening up to the public. This was a long time coming.

For years I’d been in a flux of one step forward, two steps back. Usually when I launch something there’s a degree of shipping anxiety, but I felt elated to get With Jack out into the world. I was so ready to devote myself to this.

12 months down the line, how does With Jack look? Well, it’s starting to look more like a business!

  • 135 customers
  • £36000+ gross premium written

Provided my customers stay with Jack come renewal time, I’ll see revenue double. Year two is magical for brokers and I’m excited to feel the effect of that on my cash flow!

Top Sources of Traffic

  • Organic search
  • Twitter
  • Designer News

The traffic that converts the best is:

Organic search has been performing well recently. With Jack is now on the first page of Google, sandwiched between my big competitors (and the insurers who passed on working with me).

Google—as we all know—involves playing the long game. A year of creating content like this is paying off.

Although Analytics can’t display this data, I’ve seen a lot more customers coming from recommendations through Slack. Technology and design communities are big in Slack, and this is the audience With Jack targets.

An avenue I’ve just started experimenting with is YouTube. A few weeks ago I launched a YouTube channel intended as a weekly insight into my work.

It’s too early to gauge if this is a good marketing channel, but the reaction has been positive and I’m enjoying learning something new (filming and editing).

On the topic of learning something new, I thought I’d find taking up video frustrating because I’m just learning and not very good at it. It was important I gave myself permission to ‘be crap’ in the beginning while finding my feet. That’s what’s enabled me to dive in with YouTube—this acceptance that it’s rough and doesn’t need to be perfect.

I keep learning this the hard way.

The last update I did on Jack’s figures, I had just paid for a sponsored post on a design blog. I was apprehensive about this because—from all the marketing I’ve done—the free tools I’ve built, recommendations and presence on Twitter convert the best. Paid ads always left a bad taste in my mouth.

“Maybe this time will be different”, I thought.

It wasn’t.

I don’t think insurance translates well to ads. You’re only shopping for insurance when it’s something you need—not something you see and think, “That would be nice to have”.

My Highlights of the Year

  • Winning The Rookie Award at the Digital Insurance Awards.
  • Meeting my customers. With each city I’ve visited in the UK, I’ve made a point of meeting my customers. Katherine, Rachel and Mikleo in Manchester, Martin in Newcastle, and Sabine and Rohan in Glasgow.
  • Applying to an accelerator. I didn’t get investment from Ignite, but attending the monthly off-sites has provided me with so much value. Being around other founders, learning from other startups… it’s been invaluable.

What's Next?

Instant quotes.

For the last year I’ve been manually processing quotes. It’s nice being in the trenches with my customers, but I know from customer development that people want instant quotes.

Side note: For customer development I’ve started using a neat tool called Iterate.

I won’t bore you with the logistics of why we haven’t implemented instant quotes, but things are moving in that direction. Scott is mocking up the customer journey as I type. However, in the insurance world this could take a while to roll out…

Ultimately, I want to build the best suite of tools for freelancers to buy and manage their insurance. This requires money and I’m self-funded. I didn’t get investment from Ignite (more in that another time), so weekend photography jobs are funding the development of With Jack.

I’ve had to ask myself how serious I am about this and how much I believe in what I’m building. The answer is “100% serious”. Now I’m weighing up my options for putting money into With Jack.

Getting to 135 customers with no money and bootstrapping as a solo founder is good validation, but now it’s time to up the ante.

Thank you to my 135 customers who have supported With Jack and are helping to shape insurance for freelancers.

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