A Look Back On With Jack's First Year

A Look Back On With Jack's First Year

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.

Paid Ads Suck

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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Introducing My Startup Diary

Introducing My Startup Diary

Vlogging has been on my mind for a while. I had a YouTube channel in a past life when I was a gamer. I stopped because I fell away from gaming—and because the YouTube community hated me (but that’s what happens when you’re a female gamer).

I already had the kit I needed to get started with Vlogging because I do photography. A camera that shoots video, lenses, a tripod… Let’s go!

I wanted to record a diary of sorts. A behind the scenes of building With Jack. Real, honest insights—even on days when things aren’t going well. Building a business isn’t always dollar bills falling from the sky, you know.

I’ve been enjoying Justin Jackson and Noah Kagan’s YouTube channel. They focus on business and building products, and Justin films the occasional vlog.

I thought I could offer a different persepctive as a solo, female founder bootstrapping a business in Scotland. Not only that, but the UK insurance industry isn’t very transparent. Nobody is really sharing the process of building an insurance business, warts and all.

My Startup Diary is now on YouTube and updated weekly. If you like it, please become a subscriber!

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My Experience Applying To An Accelerator

My Experience Applying To An Accelerator

Last Tuesday I drove to Newcastle for Ignite’s distributed accelerator programme. It was the final stage of the application process for the Ignite Accelerator, and I had no idea what I was getting myself into.

Everything about accelerators scare me. It’s a world that I’m not familiar with. Prior to last week, I did’t know the difference between a Venture Capitalist and an Angel Investor.

I’ve never had someone tear apart my business before, albeit constructively. My mum always tells me I’m doing a great job.

The week before Ignite I had reached a milestone at With Jack. I hit the 100 customer mark and was feeling confident. This metric validated my business.

With a conversion rate of 30%+, it was an indication to keep on trucking to 1000.

  • 100 Customers = Validation
  • 1000 Customers = Profitable business
  • 10,000 Customers = Lifestyle business
  • 100,000 Customers = Multi-million pound business

My confidence didn’t last. A couple of days before setting off for Newcastle, doubt set in.

I’m not good enough as a founder. My business isn’t solving a big enough problem. Everyone is going to be further along than me. What if I don’t know my figures? I’m afraid I’ll look stupid.

It turns out this was normal. Having spoken to the other startups at the offsite, most felt the same.

Some of the other startups at Ignite off-site

The Application Process

What followed was an intense, 2-day programme.

The first half of each day comprised of workshops on growth, hiring and more. I took a ton of notes in these sessions and came away with actionable tips—some of which I’ve implemented with positive effect.

This part of the day provided more value than many of the £200+ conferences I’ve attended.

In the afternoon we had Office Hours with investors, mentors and the Ignite team. This part of the day was challenging and tested each of us as founders.

A Brief Backstory…

My background is unconventional. 12 years ago I inherited my Dad’s insurance business. From the age of 18 I worked from home until moving into a co-working space in 2013. That’s 8 years of working from home!

For several of those years I also battled a crippling anxiety disorder. At my anxiety’s peak, I didn’t leave the house for fear of having panic attacks. It took over my life.

I don’t recognise that person anymore, but I often joke that the 8 years I spent working from home—and with the little social interaction I had—my social skills have been affected. In other words, this was way out of my comfort zone!

I was asked difficult questions. I didn’t have answers to all of them. At times it looked like I don’t know what I’m doing. I met disinterested and stony-faced Venture Capitalists. I went into these sessions feeling proud of what I’m building, but left wondering why I was even there.

While some of what I’m saying sounds negative, it isn’t.

Being a solo founder, I need to have a network of people who question my beliefs. Test my assumptions. Challenge my theories. I believe that’s what will take With Jack from 100 customers to 1000 and beyond.

After feeling exhausted and bruised, we ended the first day with a 3 minute pitch.

Despite doing a bit of public speaking, it’s still an uncomfortable process for me. But this was different. Everyone in that room was in the same boat. Sharing the experience and knowing what we were all going through, everyone was rooting for one another. There was a lot of support.

Day two followed the same format. This time I felt prepared for stony-faced Venture Capitalists. I felt prepared for difficult questions. I felt prepared to doubt myself.

After embracing the uneasiness of it all, I ended the experience on a high.

Some of the other startups at Ignite off-site

Why Did I Apply To Ignite?

What problems is With Jack facing that compelled me to apply to Ignite?

  • I’m a solo founder and need a network of mentors around me.
  • My conversion rate is great, but I’m lacking volume. How do I scale and get more customers?
  • I burned through my cash on developing Jack’s customer journey.

An unexpected upside of Ignite was meeting other early-stage startup founders. I don’t have many friends in this circle.

Although I love my friends, I sometimes feel I’m wired up differently. I want to talk about business, marketing and the problems I’m facing growing With Jack. None of my friends find this interesting. I can see their eyes glaze over when I try to talk about Jack—or they just don’t reply to my texts!

There was an instant bond with the group. I liked everybody I met. So much so that if I don’t get accepted onto the Ignite programme, I won’t feel resentment or bitterness. I’ll be happy for the startups that get through.

I extracted enough value from the offsite that my 48 hours in Newcastle, irrespective of the outcome, was worthwhile. What a whirlwind experience!

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My First 100 Customers

My First 100 Customers

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 Jack’s 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

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:

  • Somebody searches for an answer on Google
  • They find one or two of Jack’s articles
  • They like the brand
  • They get a quote
  • They become a customer

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 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.

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A Few Updates…

A Few Updates…

Since launching With Jack I’ve stuck to semi-regular updates. Usually I write a blog post every fortnight or so, but life got in the way.

Here are some of the events that took priority over blogging:

  • My dog got sick. A cancerous tumour followed by pancreatitis. I’m really attached to my dog, so that sucked
  • Wedding season kicked off. I’m still shooting weddings so I have funds to put into Jack
  • Traveling. I flew to South Uist for an island wedding and visited England to film a segment for Right on the Money

Now that my dog’s better and I have no more weddings until July, I have a couple of (relatively) uninterrupted weeks to get back into my routine! Let me fill you in on what’s been happening.

Improvements To The Onboarding Process

It’s funny looking back on the first few months of With Jack. The only part of the process with any polish was the quote system. Beyond that it was scrappy, not to mention I was only offering one product.

I’ve enjoyed iterating on With Jack since its soft-launch in August. First by rolling out new products based on what customers were requesting. And now by polishing the rest of the onboarding process—the risk questions.

For those that haven’t yet used With Jack, the current process looks like this:

  1. You submit your details via our quote engine
  2. Jack emails you a breakdown of your quote
  3. You answer your risk questions
  4. Jack sends you your policy documents

For launch I invested my resources into step 1, the quote system. This is With Jack’s bread and butter. For step 3 we threw together a form without too much thought. It didn’t take long to notice it was causing confusion.

These were some of the questions people would ask at the risk questions stage:

“Is this the final step? Am I committed to buying insurance? How do I pay?”

I worked with Naomi Atkinson on redesigning the risk questions. We specifically addressed the above confusions and rolled out the updated form last month.

Here’s the before and after:

A before and after of the risk questions form

Aesthetically it’s a lot better, fitting Jack’s whole ‘design at the core’ ethos. More importantly—since implementing the new design—I haven’t heard any of the above questions.

Mission: Accomplished.

Inching Closer To 100 Customers

The next blog post I publish will be celebrating hitting the 100 customer mark. (I hope.)

Right now I have 95 customers. This means I’m a 1.5 weeks away from the big 100! That is unless I have a surprisingly good or horribly slow fortnight.

With Jack is about much more than the numbers, though. I could have 10 customers and it would still have the same mission—getting creative businesses the protection they need, doing so with as little hassle as possible and in a format that’s simple.

With that said, I can’t deny that getting to 100 customers as a bootstrapped, solo founder feels great.

This nicely ties into my next update…

I've Applied To An Accelerator

I did something I never thought I would. I applied to Ignite, an accelerator.

Let me back up a bit.

A few months ago I attended a startup dinner in Edinburgh where Tristan (Ignite’s CEO) was a guest. Tristan and I have met before, but this was the first time I asked if Ignite would be a good fit for me.

As much as I want to champion bootstrapping and love the idea of being a solo founder, I’m struggling with building Jack on my own. It’s growing very slowly. I feel I’d benefit from a network, mentorship and being around other startups.

I’m not comfortable with accelerators (mostly because I like hiding behind my computer). But if something scares me, it’s usually a good indicator I should try it.

I had my video interview last week. I’ve since been invited to the last stage of the application process in Newcastle. This is what determines who is accepted into the final programme.

Fingers, toes and eyeballs crossed.

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