9 months ago I launched With Jack.

This wasn’t my first launch. I’ve shipped a few projects over the years;

  • A podcast
  • An email course
  • A SaaS app
  • Insurance by Jack
  • A vlog (coming soon)

Each launch had varying degrees of success, but one thing has always struck me. Launches are unpredictable and often underwhelming.

I used to expect big things from launches. “This is it. This is the idea that’s going to take off. It’s a guaranteed win.” After a while I learned to scale back my assumptions and have more realistic expectations.

When it came time to launch With Jack from a hotel room in Berlin, I didn’t set expectations. Yes, I’d spent years trying to get it off the ground and invested thousands of pounds into it. The stakes felt high. But I wanted to quietly push it live, iterate on it every day and see where it could go.

Where Can It Go?

Today I reached the 100 customer mark.

To say I’m excited is an understatement! 100 isn’t a sustainable business, yet it’s a milestone that validates I’m headed in the right direction. If you can get 100 customers, you can scale beyond that to 200, 400, 1000 etc.

Simply getting to launch day was a hurdle. Reaching 100 customers fills me with optimism. Like this idea for With Jack has potential. It’s got legs.

How Did I Get 100 Customers?

All the feels and past disappointments aside, how did I get 100 customers?

  1. Networking
  2. Referrals
  3. Twitter
  4. Leads from Jack’s MVP
  5. Organic search


It’s no surprise that relationships have had the biggest impact on my business.

With Jack targets an audience of creative professionals. 70% of my customers are web designers and developers, and the rest are a mix of graphic designers, photographers, copywriters and more.

Years ago—before With Jack was conceived—I took an interest in the web industry. I was fascinated with web design and learned to code.

To learn more about web design and development, I started attending conferences. I read web industry publications and followed designers and developers on Twitter.

Sean McCabe suggests building relationships now for the business you’ll be building in 3 years.

This is what I was doing, albeit unintentionally. I didn’t have anything to sell, I just really liked the web industry and found these people fun to hang out with.

Socialising at industry conferences
Being sociable and making new friends at conferences. Photo by Filly Campbell.

Every year I’d travel to New Adventures in Web Design in Nottingham or Build in Belfast. It was through networking at these conferences I met people I’m still friends with today. Many of these friends became With Jack’s first customers.

Lesson: Take Sean’s advice about building relationships now. Pick an audience you like, focus on helping them and grow your network. Start with people.


Referrals are the strongest indication you’re doing something right. Every time I hear, “My friend got their insurance through you and recommended your service” it’s proof With Jack is on the right path.

What’s worked with Jack is being laser focused on a specific audience.

Most insurers tend to target every type of business. So their web site copy and marketing material is trying to appeal to, say, traditional tradesmen and digital businesses. It’s hard to make that work.

When a designer or developer asks for business insurance recommendations, With Jack is often suggested. This is because our marketing, copy and customer rewards are all aligned with that particular audience.

With Jack immediately pops into their head instead of ‘that insurer that offers every type of insurance for every type of occasion’.

Lesson: These referrals came my way without prompt or actively encouraging them. I think referrals happen when you do something well and are generally just helpful.


When I say Twitter I’m not talking about sponsored tweets (that’s no.7 on the list), but from being active on Twitter for the past decade.

Wow. For 10 years I’ve been tweeting about the video games I’m playing and what I’m eating for lunch.

On a serious note, I joined Twitter in 2007 when there was no With Jack. I was unhappy in my job and had never owned a camera. I was a hardcore gamer with an anxiety disorder.

Over the years, people have followed my journey in insurance through Twitter. The idea of improving technology in the insurance industry. Building my first quote system prototype. Starting to get invited to speak at conferences. Launching Insurance by Jack (and that not doing so well). Trying to find an insurer to come onboard with Jack. Being totally burnt out and admitted to hospital. Passing my first insurance exam. And finally launching With Jack.

Inviting people on this journey with me has been invaluable. Not all of them are in the market to become customers, but for those who are they feel like they’ve gotten to know me. They want to support the business I’ve worked hard to launch.

Lesson: Document your journey. Twitter isn’t a platform that will work for everyone, but I got on it early and became an active user. It can be uncomfortable sharing the vulnerable moments. It’s easier to show up when you’re financially stable and have 10,000 customers, but I think being transparent about your journey and involving people in it will help you get there quicker.

Leads from Jack's MVP

In May of 2014 I launched Insurance by Jack. I’ve described this as my MVP, but I’m in two minds as to whether I should have ever taken that route. (I’ll write a post dissecting where and why this business went wrong. Subscribe to my newsletter if you don’t want to miss it.)

I did a lot of brand damage with this business. I had a website that did a great job at communicating my vision, but fell short where it actually mattered—delivering on that vision.

People came to the web site with certain expectations, but those expectations weren’t being met. People’s first experience with Insurance by Jack was poor—and first impressions matter.

On the other hand, some of the people that stumbled upon Insurance by Jack took an interest in where it could go. They signed up to the newsletter or became followers on social media. Some of those leads are now With Jack customers.

It validated the idea I had, but I do wish I could have made a better first impression.

Speaking about Insurance by Jack
Speaking about Insurance by Jack and how it may not be a success but a stepping stone to something else. Spoiler: It wasn't a success, but it was a stepping stone to what became With Jack.

Lesson: Although I’m disappointed that Insurance by Jack delivered a poor first impression, it served a purpose despite its imperfections. I got a lot of mistakes out of the way and drummed up interest from people that would later become customers.

Organic search has been great for bringing people outside of my network to With Jack. As Jack becomes more of an established brand, I think I’ll see more customers come via this channel.

Currently, the customer journey via organic search looks like this:

With Jack’s rankings will only improve as I write more content. I use Answer The Public to discover what questions people are asking, then I create blog posts or landing pages around it.

Because I’m focusing on a specific audience it’s easy to find out what to write about. I can learn what confuses them about insurance and use examples that hit home.

Lesson: I don’t think I need to tell you the value of ranking in Google with valuable content. Your audience is searching for answers. By providing value, you build trust and potentially win customers.

The List Goes On…

I’ve covered the top 5 channels, but there are many more that have brought me customers.

  1. Public speaking
  2. Promoted ads on Twitter
  3. With Jack's beta testers
  4. Designer News
  5. Podcast appearances
  6. Product Hunt
  7. A blog post about chat bots

I think getting to 100 customers boils down to a few things.

Finding An Audience You Want To Serve

One of the reasons I couldn’t make a success of my Dad’s insurance business was that it served an audience I was disinterested in. You’re going to be hanging out with these people, talking to them and getting into their heads. If you don’t see yourself having coffee with them every day, it’s not the right fit.

Keeping It Simple

If I was to follow industry trends, I’d have launched with a similar format to other insurers. Multiple providers, different types of cover and aiming to appeal to every type of consumer. Instead I worked with one provider, offered one product and catered to a specific group of people. This approach meant I could launch quicker and with less capital. It also helped with tailoring With Jack’s customer journey to a particular group of people. This makes the experience as good as possible for them, which leads to happy customers and referrals.


Lastly, I will leave you with some stats.

  • 21,992 visitors
  • 100 customers
  • £24879.53 gross premium written

Here's To The Next 100?

I believe I can scale this business, but I want to take a moment to appreciate getting to 100 customers.

In business you always look forward. “Okay, we launched. What’s next? Okay, we have 100 customers. How do we get to 200?”. But this milestone is one I want to savour. It took so bloody long to get here.

Thank you to each of you who have used With Jack to arrange your insurance.