Maybe 4 months in business is too soon for a ‘Year In Review’, but I’m a sucker for those posts (and I’ve learned a lot in 4 months).

I quietly launched With Jack at the tail-end of August. I was sitting in a hotel room in Berlin with my sister. After a bumpy few years getting With Jack off the ground, I deployed the code to GitHub and went out to explore the city. Great city, by the way.

To finally implement my own design and technology (a work in progress) after years of trying… I can’t describe how it felt! It’s the beginning of building the company that’s been swirling around in my head for years.

This journey is just as fun as I thought it would be, but also a lot tougher. Guys, business is really hard. I have respect for anybody working on their own thing, because it isn’t easy.

I had a taster of it with Insurance by Jack, which was made all the more challenging by building on top of someone else’s platform. No access to data, no control over the customer journey, not knowing who my customers were or what marketing channels worked.

Building a business is challenging enough, but doing so without creative control or access to data? Impossible.

Anyway… let’s get into this.

Almost 4 months in With Jack has 41 customers. They’re evenly split down the middle with designers and developers, then there’s the odd marketer and consultant.

Top Sources Of Traffic

I’ve tried various methods of getting traffic (cheaply). Facebook and Twitter, banner ads… What’s worked best has been our Designer News and Product Hunt features.

As a result, I’ve decided to cut back on ads and focus on tools and creating value. For example, I launched a business health checkup tool that assesses the vulnerability of your freelance business. I’m sharing it with communities like Designer News.

Spikes in traffic
Spikes in traffic since launch

Marketing insurance is about planting a seed. It may not be a freelancer’s time to renew, so they’re not yet ready to get a quote with Jack. This is why I find push marketing less effective.

Provided I can get With Jack in front of the right people, I’ll plant that seed for renewal time. That’s what micro-sites like the business health checkup tool are helping me do. I’m playing the long game.

Tools For Building With Jack

Update 06/12/17: Here’s an updated list of the tools I use

These are the tools I can’t live without. I wrote about Pipedrive and my CRM tool in more detail on another blog post.

Pipedrive is where I track my sales funnel. 4 months in I’ve given out 152 quotes. Pipedrive is where I keep track of the genuine leads and at what stage in the funnel they’re at. I add customer details, whether I’ve followed up for a second or third time, and reasons I’ve lost a lead.

As more leads come in, Pipedrive is invaluable for keeping track of everything.

Google Analytics is ugly but does the trick. I’d love to use something aesthetic like GoSquared, but it’s expensive.

Analytics does everything I need it to. I make the most of it by setting ‘Goals’ and tracking them. I can see which blog posts convert readers into customers. (These two, if you’re curious.)

Top Expenses

  • Design
  • Development
  • Insurance

All of the money I’ve made has been reinvested into design and development. For example, building the business health checkup tool and the quote system.

Next I’ll be investing money into the quote system. The aim is to pad it out with additional cover and features based on user feedback. Most of our customers require worldwide cover due to working with clients, for example, in the US. It makes sense to build this—and other regularly requested features—into the quote system.

My other expense has been insurance. If you thought arranging insurance for your business sucks, try arranging insurance for your insurance business.

Proudest Moment

In October I was shortlisted for an award at the Digital Insurance Awards 2016. The Rookie Award, to be precise. The ceremony took place on November 18th and I won!

The image at the top of this blog post is of my award. It’s an alarm clock. #wakeupinsurance is the event’s hashtag. Wakey, wakey. Alarm clock. Get it?

What Didn't Go Well?

I took a gamble by taking out an ad for Black Friday. I spent £235 on the ad plus £180 on the product I’d be giving away. It got me one sale. That’s £26.25 in commission. That’s a loss of £388.75. Ouch.

Making mistakes is inevitable, as long as they’re occasional. Next time I try throwing money at ads, talk me out of it. At this early stage that money is better spent elsewhere.

Cold, Hard Stats

  • 16,449 Visitors
  • 41 Customers
  • 26% Conversion Rate
  • £10293.93 Gross Premium Written


Despite being an introvert, I can’t say I enjoy being a ‘solopreneur’. I’d love to have a co-founder or partner to share this rollercoaster ride with. It’d help having someone onboard with a skillset I don’t have, like a designer.

Fortunately, I’m a member of a community of product people. It’s run by Justin Jackson. You may see me tweeting his stuff often (and I’ve even linked to his blog in this article), but it’s because his content is gold.

I was also a member of Fizzle for a while. I cancelled my membership to cut back on expenses.

It’s worth joining a community of people in the same boat if you’re a solo founder. They hold you accountable with shipping, and after launch you’ll get feedback and advice on marketing.

It’s not the same as having a co-founder, but it helps me to feel a little less ‘solo’.

What's Next?

I want to grow With Jack into a community for freelancers. To have a body of designers, developers and more, it seems wasteful to not build in community features. A forum for discussion, a job board, accountability or collaboration features… I don’t know yet. If there’s anything you’d like to see from With Jack, let me know.

My big goal is to punch an insurer’s rates into my system so quotes and cover are instant. I hope I can make that happen in 2017, but it all depends on the volume of business I continue placing.

I want to thank those first 41 customers! Jack doesn’t have many features right now–it’s pretty barebones. It will get somewhere, but not without support from designers, developers and other freelancers.

Looking Back

This jumped out at me when looking over my 2015 review:

I’m confident that with the effort I put into phasing out distractions in 2015, I’ll have a more focused and productive 2016.

2015 was all about phasing out distractions and focusing on insurance. It felt like a quiet and uneventful year, but it ultimately lead to launching With Jack in 2016. With that said, 2016 was just a warm-up for Jack.

I’ve dipped my toe in the water. I like it. I’m going all in.