A Look At Jack's Figures 7 Months In

A Look At Jack's Figures 7 Months In

3 months ago I wrote Jack’s year in review post. This was after only 4 months in business—1 of which was a soft launch. After putting my 81st customer on cover this week, I looked at some of the same figures that lead to that post.

Three months ago, my figures looked like this:

  • 16,449 visitors
  • 41 customers
  • £10293.93 gross premium written

Today, they look like this:

  • 19,482 visitors
  • 81 customers
  • £20377.29 gross premium written

Traffic has dropped considerably, which is inevitable after the buzz of launch day fades. So have the number of quotes I’ve processed. Despite this, my conversion rate has improved and I’ve generated another £10,000 of Gross Premium Written.

I wanted to gain a better insight into these figures. I’m putting the same number of people on cover despite a drop in traffic and quotes.

I took to the solo founder group I’m a member of and asked why they thought this was.

The consensus is:

Insurance is a yearly purchase. Much of my audience wouldn’t have been ready to buy insurance initially as they had existing policies.

Secondly, Jack’s launch garnered interest from a user base that isn’t my market (geographic eligibility/fit the criteria). It also exposed Jack to people who are my market and used us to arrange their insurance. They now follow Jack on social media or recommend us to their friends, exposing us to more of our target market without the same footprint as launch.

Our overall footprint is smaller, but our target market footprint is bigger.

This sounds right. More than 50% of my visitors have come from the States. (I still receive quotes from people outside of the UK—even thought it’s a .co.uk. domain and the currency is in GBP—but fewer than before.)

I’m also seeing more sign-ups through recommendations. I’d love to encourage this behaviour with a referral program

Top Sources of Traffic

Three months ago, my top sources of traffic were:

Today, they look like this:

  • Designer News
  • Organic search
  • Twitter

I’ve been focusing on creating content, so I’m happy to see organic search performing well.

What I’m more interested in is traffic that converts. Whilst I stupidly didn’t track this from day one, I have Goals set up in Analytics. They monitor my CTA click-throughs and those who complete a quote and submit their details.

The traffic that converts best is:

Jack's Strategy

When I launched Jack I had no idea what would work. I still don’t. But 6-7 months in I’m building a better picture of where to focus my time, energy and money.

Content is performing well. I think this is because most insurers don’t cater their content to creative professionals. They can tell you why a tradesman needs insurance or a solicitor, but not a web designer or developer.

Some of the stories I’m sharing about insurance for creatives invoke action or plant a seed. I’ve just paid for sponsored content on a popular blog, so it will be interesting to see how that converts.

I also built a tool that generated more quotes in 2 days than the entire week before. Few of these have converted yet, but I’m hoping there’s a delayed effect and it’s a slow burner. The response to the tool has been positive.

Check out those RT's!

As the months progress, I’m hoping less of my marketing will be guesswork and more decisions will be informed by data.

Something tells me, however, that it doesn’t matter if you’re 7 months or 7 years in—marketing is a constant experiment and full of surprises.

read more

What Does Validation Look Like?

What Does Validation Look Like?

As With Jack has been live for 6+ months, this is a question I’ve been exploring.

Whenever people ask, “How’s Jack going?”, I’m never sure what to respond with. Do I tell them how many customers I have? Focus on the conversion rate? Or do I be upfront and say “It’s going well, but it’s still not supporting me yet”?

Depending on who’s asking I’ll say a mixture of those things. “It’s going well. We have 73 customers and are growing every week, but it’s hit a plateau. We have a conversion rate of 25%, but it’s volume we’re lacking.”

To some this sounds like a promising start. To others, they seem sympathetic to my startup woes. This is because validation looks different to everyone.

To me, With Jack has been validated.

Here’s how I personally measure validation:

  • Creatively satisfied. I crawl into bed at the end of the day feeling challenged and creatively satisfied. Insurance isn't known for being a creative industry, but I bring those elements into my job. Making visuals, writing content, coding etc.
  • No Sunday dread. I'm not on Facebook anymore, but I'd log in on Sunday evenings to be met with a wall full of 'Sunday dread'. These are the people who aren't looking forward to work on Monday. There are 52 (or 53) Sundays in the year—that's a lot of dread!
  • Comparing it to my previous attempt. With Insurance by Jack, I won 55 customers in 2 years. Compare this to 73 customers in 6 months and With Jack is looking encouraging. It supports what I was saying all along. A better customer journey will delight visitors and improve the conversion rate.
  • Customer feedback. Emails, tweets. Every time someone vouches for With Jack, I feel a sense of validation. With Jack's goal is to make business insurance accessible to freelancers and those working in the digital sector. Statements like this affirm I'm closer to fulfilling that goal.
  • Making money. With Jack has been making money from day one, although it still isn't enough to support me. Every week we're putting new customers on cover.

But maybe I wouldn’t think Jack has been validated if I had 3 kids to feed.

Maybe I wouldn’t think Jack has been validated if I’d left a job with a £60K salary to pursue it.

I’m fortunate that I’m building Jack with a financial cushion from other projects. This is why it’s impossible to have a blanket response to “What does validation look like?”. Everybody’s circumstances / goals are different, therefore validation looks different to everyone.

Playing The Long Game

Another factor I consider is time. It took my dad 2 years to start earning a decent income with his insurance business. (In case you haven’t noticed, my dad is a big inspiration to me. That’s who I named my business after.)

Year 2 is magical for brokers. On top of the new business they’re bringing in, they’re enjoying renewals from year 1. That book of customers begins to build.

Despite an insight into how my dad built his business, my mind wrestles with the articles I read on marketing and business in the startup world. You know the type. The ones with the clickbait titles?

“How My Website Made £17,000 With This One Simple Tweak”

“Idea To £25,000 In One Weekend”

“How We Got 100,000 Users In 24 Hours”

While they’re fun to read and (maybe) spark ideas to apply to your own business, they’re unrealistic. They make business sound easy. The overnight success story. My worry is people read these articles thinking that’s how business should look.

Nobody writes about “How It Took Me 500 Days Of Showing Up And Making Lots Of Mistakes To Earn Enough Money To Pay My Bills”. That’s partly why I blog about where I’m going wrong, because that part is just as educational as when you get it right.

Side note: A business blog I enjoy reading that’s refreshingly honest is Adii Pienaar’s.

In 2015 I changed a lot about the way I do business. I used to follow my creative itch, starting a new project whenever inspiration hit. I’d then move onto the next thing when I got bored or lost steam.

That’s not me anymore. I’ve learned to focus. I give one project my attention, I experiment with it and I’m patient. I don’t expect overnight results.

To answer the question, “What does validation look like?”. You can decide based on your circumstances and goals. Ignore the clickbait headlines, how others measure their success and focus on what validation looks like to you.

Header icon is from Hand Drawn Goods, which is licensed under CC BY 2.5.

read more

Turning My Robbery Into A Positive Experience

Turning My Robbery Into A Positive Experience

Last month I celebrated my birthday in Geneva. While turning 30 in Switzerland, my home in Scotland was robbed.

The intruder broke in via my terrace door. He stole my PlayStation 4, 13 video games, iPad, sound dock, iPod Touch, my camera bag, which had a Canon 5D MK II in it, two flash guns, 7 CF cards and a 28mm lens. Yes, a lot.

If anybody was going to have insurance, it was me!

Working in insurance yet being on the consumer end has been an interesting experience. Going through the claims process, I made observations I can apply to my own insurance business.

An Easy Way To Know What You Own

Problem: Not having proof of purchase, knowing when you bought items, their value and the specific model. This can slow down the claims process.

When I made my claim, I was aware I didn’t have proof of purchase for a number of items and figured this could give my insurer an easy out. “We’re not paying for that item. You can’t prove you even owned it.”

I tried to provide evidence where possible. I have a freakishly good memory of dates. This came in handy for remembering when I bought items. I was able to search my bank statements and locate specific purchases.

If you’re with a good insurer, they’ll understand you haven’t kept a receipt for Wolfenstein: The New Order that you bought 3 years ago. A good insurer will honour the claim.

This is (one reason) why you shouldn’t choose the cheapest provider. Most people don’t trust their insurer, but I’d guess a majority of those bought the cheapest cover and got burnt. Not all insurance policies are created equal.

I digress. Relying on your memory for dates of purchase, what model you own and its worth won’t always cut it. It will also slow down the claims process.

Solution: An app for customers to itemise their contents. If ever they were to make a claim, they could easily select which items had been stolen or damaged without digging up receipts or product information.

This does pose another problem. Who can be bothered taking the time to file their contents? An incentive could be offered by the insurer for doing so, whether it’s cashback or a reward.

Digital Update On The Progress Of Your Claim

Problem: The process of making a claim is archaic. Phone a call centre, wait in a queue. Lame. I can quote and buy my insurance online, but that’s where the digital experience ends.

My insurer paid out for all of my stolen contents. One advisor even investigated the payout for my video games, thinking their colleague had wrongly price matched them against second-hand games. This is from an industry that’s associated with doing anything to get out of helping their customers.

Where it fell short, however, was the lack of communication. If I wasn’t chasing them up I had no indication as to what stage my claim was at. When your house has been burgled and your valuables have been taken, you want to know when you’re going to get your stuff back.

I come from a generation who hate speaking on the phone, so liasing with a call centre every few days was a nuisance.

What I really wanted was the ability to login to a dashboard and see what stage my claim was at.

  1. “We’ve received your claim”
  2. “We’ve appointed an electrical specialist”
  3. “Your electrical specialist is price checking your contents”
  4. “Your claim has been processed. We’re sending you a cash settlement of £3000”.

That kind of thing.

Solution: A dashboard for customers to login and have an overview of the status of their claim. I understand the phone can’t be avoided completely, but it’s uneccesary and time consuming for small updates as to what point you’re at with the claims process.

I had a pleasing experience with my insurer, yet I couldn’t help but make these observations. I’d love to apply my experience to Jack in the future. At least this robbery would have had something positive come from it.

Misc Notes

If you’re buying contents insurance these are some things to be aware of:

  • Make sure you have new for old cover. This means if your 10 year-old dSLR gets stolen, the insurer will replace it with the current model.
  • Inform your insurer of any high value items. If your £3000 TV is damaged, your insurer may not pay out because it’s a high value item you didn’t disclose. The more honest you are, the better. Don’t leave stuff out so your premium is cheaper.
  • Your work equipment won’t be insured under your home insurance, so ensure you have business insurance for your contents. According to Gartner, a laptop is stolen every 53 seconds! Coincendentally, Jack just rolled out the ability to insure your business contents.
  • I wrote a about my burglary from a business perspective on Jack’s blog. If your work equipment is stolen, can you still function as a business? What about back-ups? These were the questions I had to address when it happened to me.

read more

What Channels Drive The Best Quote Conversions?

What Channels Drive The Best Quote Conversions?

When writing a recent business plan for an underwriter, I had to dive into Google Analytics to gauge what channels convert best for Jack. This is something I should do regularly, I know, but juggling everything as a solo founder is hard.

Conversions are based on the number of quote completions. People who haven’t just clicked ‘Get a Quote’, but have supplied all of the requested information to receive a formal quote.

Top 10 Converting Channels
  1. Google / Organic
  2. The Future of Web Forms
  3. Twitter
  4. Business Health Check-up Tool
  5. Designer News
  6. This blog
  7. Email
  8. Facebook
  9. Web design galleries
  10. Instagram

Let’s take a closer look at how I’m utilising some of these channels.

Google / Organic

I used to struggle with knowing what content to write, but I now have a better idea of what’s helpful to my audience of freelancers. I learned this through;

  1. A neat trick from Tiny Marketing Wins on researching what customers want
  2. Asking them! Whether we’re having coffee or chatting via email, I explore what confusions freelancers have about business insurance and pay attention to the questions they ask

I explore common questions freelancers have regarding insurance, then I create a blog post or landing page around it. Insurers focus their content on more traditional industries, so freelancers in the digital sector still have a lot of confusion about insurance.

Recently I decided to focus a lot more on writing. It’s clearly effective in converting to quotes, and the bonus is that it costs only my time.

By following the above practices, I add my research to a Google Doc and highlight what would make a good landing page or blog post. Then I start writing.

The document I use for my content research
The document I use for my content research

By doing this I’ve built a decent backlog of content ideas. All of it is relevant to my audience and is questions they’re explicitly asking or terms they’re searching for online. Win-win.

Business Health Check-up Tool

A while back I conducted a survey of freelancers. The results highlighted that some don’t treat freelancing like a business. No contracts, no insurance. Yikes.

Many freelancers could be doing a better job of protecting their business, so I made this business health check-up tool.

I covered the importance of monitoring cashflow, having insurance, working with contracts and backing up your work.

If something goes wrong, the reality of freelancing is that there’s nobody to hold accountable. You are your business. If a client’s unhappy, it’s you they’ll be pointing the finger at. It’s a lot of responsibility on one person’s shoulder, which is why I think freelancers should protect themselves.

While this tool hasn’t driven as much traffic as I’d have liked (partly down to my poor marketing effort), the leads it has sent have been high quality and converted to quotes. It’s Jack’s 4th best channel for conversions.

Investing in building tools like this—which are useful to my audience—makes more sense than throwing money away on ads. Even Hiten Shah says so.

Designer News

If I was to make a list of places my target market hang out, it would look something like this (in no order):

  • Designer News
  • Product Hunt
  • Reddit
  • Hacker News
  • Twitter

Designer News drives a lot of traffic. The downside is that it’s time sensitive. Your submission will get buried quickly, so it isn’t evergreen traffic.

Jack’s been featured on Designer News a few times. When we launched, for a landing page I created, with the business health check-up tool and also for a paid slot.

I was surprised the traffic it’s sent my way converted so well. When I send customers their policy documents, I ask how they heard of Jack. Designer News has been cited on a few occasions.

It isn’t an immediate conversion. They see the name, they bookmark us for later.

This also ties into the channels I covered above (the business health check-up tool and organic content). To take advantage of Designer News’ audience, I have to keep creating useful tools or content to help my audience.

It’s worth mentioning that the second best converter, The Future of Web Forms, is curious users. I don’t think any of them have become paying customers and that’s OK. I welcome people to check out Jack.

The channels that drive the best quote conversions will change as the business develops. I’m learning as I go along and there are still many avenues I haven’t explored.

read more

Why I Launched With One Product

Why I Launched With One Product

If you are not embarrassed by the first version of your product, you've launched too late. — Reid Hoffman

Anybody in the start-up world will have heard the above quote. It makes a lot of sense, but it’s challenging to launch with an incomplete vision. After refining your idea for so long, launching with anything less than perfect doesn’t feel right.

You want to share the end result with the world and get it right from day one. It’s this danger that prevents people from shipping at all.

In August I launched Jack. I wouldn’t say I was embarrassed by it—I was proud to get to the point of shipping because it had been a long slog. But I purposely launched with a bare bones business model.

Jack started with just one type of insurance.

Despite it not being the industry norm to offer only one type of cover, I’m glad I did. If I was to build another business I’d adopt the same one product approach. Below are the reasons why.

Avoid Making Assumptions By Gathering Data

Professional indemnity is the most popular cover amongst freelancers. Making this Jack’s flagship product—and the one we’d launch with—was a no-brainer. I wouldn’t run any business without it.

The other key covers are:

  1. Public liability
  2. Employers’ liability
  3. Contents

I could guess what insurance my audience required, or I could let the data tell me.

After putting 60-odd freelancers on cover, buying patterns began to emerge. I can see that many require more cover than just professional indemnity.

22% also bought public liability. Some clients contractually require this if a contractor is working on-site.

17% insured their contents. This is a good move considering I was recently a victim of theft.

5% added employers’ liability to their policy. The lack of demand for this cover is because freelancers usually work solo. A digital agency will sometimes arrange their insurance via Jack, hence the request for this cover.

This data is influencing the business and what products I offer. Looking at these figures, it’s obvious my audience want more cover options.

Professional indemnity alone isn’t enough. Customers also want to protect their work tools (contents), themselves in case of causing third-party property damage (public liability), and their clients in case of injury (public liability).

This month we’re improving the quote system to include options to add public liability and contents insurance.

With only 5% buying employers’ liability, it doesn’t make sense to include this just yet. If Jack starts attracting more digital agencies and teams, then it would be worth building it into the quote system.

I could have guessed what cover was relevant to my audience, but assumptions can be costly if you get them wrong. Instead I’m letting the data I’m gathering influence the direction of Jack.


Professional indemnity is the most popular cover for freelancers. It made sense to launch with this product, then use data from sales to influence what other products we offered. We didn’t make assumptions. Jack’s customers told us what cover they need.

Keep Costs Down

Launching with one product keeps development costs down. The more products I offer, the more options we’ll have to build into the quote system.

It’s not just that. We’d have to implement the extra functionality into the risk question form and my CRM tool. It all adds up.

I’m bootstrapping Jack from money I earned doing wedding photography. I’m not a venture-backed start-up with deep pockets, so I have to be wary about expenditure.

One of my struggles with Jack has been knowing where to spend money. It made sense to launch with one product, earn money from that and invest it back into the business based on what the data / feedback was showing me.

Also, launching with one product has the benefit of getting to market quicker.


Launching with one product reduces the cost of development, design and other factors. This is crucial if you’re bootstrapping.

Do One Thing And Do It Well

Jack’s focus is on building a better customer journey for freelancers. I didn’t want to get bogged down in making the system more complex.

I also wanted to avoid decision fatigue. Instead of overwhelming freelancers with different products, I wanted to give them the most popular cover for their type of work.

My goal is to use design and technology to remove barriers, making it simpler for freelancers to source the insurance they need. I wanted to say, “Hey, this product is ideal for your business and it’s easy to buy”.

Excuse the pun, but I don’t want to be a Jack of all trades. I want to offer a great product (professional indemnity) to a specific audience (freelance web designers and developers). Once I got that right, then I could expand.


Take one thing and own it. Specialise.

Launching without the bells and whistles of your competitors can make your business feel incomplete. I get that. I’m breaking into an industry where the big players have been established for decades (or in some cases over a hundred years).

Some of the other factors I’d like to have launched with:

  • Instant quotes and cover
  • Customer dashboard
  • Better benefits
  • Referral program

Not having these features hasn’t prevented people from using Jack to arrange their insurance. Instead I was able to launch quickly, start generating income and use feedback to influence the direction of the business.

That’s why you should launch with one product.

read more