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 and inching towards a sustainable business.

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.

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. That it’s an overnight success. 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 important as when I get it right.

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.

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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.

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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 With 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 With 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
  • Dribbble

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 With 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 With 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.

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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.

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Lessons Learned From Inheriting The Family Business

Lessons Learned From Inheriting The Family Business

In 2005 I inherited an insurance business from my late Dad. Weeks earlier I had been studying music at college. It was big leap to running a business in an industry I knew nothing about.

Trying something new inevitably means making mistakes, but the upside is coming away from that experience having learned a lot. When it comes to building Jack, I’m applying those lessons and have (so far!) avoided the same mistakes.

Don't Put Your Eggs In One Basket

I’m explicitly referring to marketing.

While it may seem obvious, when you find a channel that’s converting well it can be tempting to focus all your efforts on that. Especially when it’s low cost.

My Dad’s business model was built around Google. Of the 10 results on Google’s first page for our chosen keyword, his websites accounted for 6 or 7 of them. He dominated the organic search results.

This worked well for him. In those days Google was the key platform people were using to shop for insurance online, and getting on the first page only cost my Dad his time. At the height of his success, he was selling 40 policies a day.

Go, Dad!

Around 2005—when I inherited the business—comparison websites exploded in popularity. The number of people using Google to shop for insurance plummeted.

Instead they flocked to comparison sites. GoCompare, Confused.com, Compare The Market…

Alongside this increase in popularity of comparison sites, Google blacklisted us for the SEO tactics my Dad had employed. Remember keyword stuffing? Apparently my Dad was a fan.

We went from having a healthy flow of leads to being completely de-indexed. All of this was happening while comparison sites were booming and we were facing tougher competition than ever.

Lesson: Diversify your marketing. Focus on 2-3 channels at a time.

Like The Audience You're Serving

My Dad’s business served the buy-to-let market. While I don’t dislike landlords, I can’t say I’m excited by their trade.

Unlike my Dad, I didn’t have experience as a landlord. He had worked in the property industry for years, first as an estate agent before moving into insurance.

He had first-hand experience buying and renting properties. This put him in the mindset of the audience he was serving, which makes business a lot simpler.

When I inherited the business in 2005, I learned web development, digital marketing, SEO (this was still a thing back then!). I studied our policy documents to understand the product, and I devoured business bibles.

Where I went wrong was failing to learn about the audience.

Getting into the heads of landlords didn’t excite me. Where did they hang out? What were their pains? What language did they use when talking about insurance? I didn’t know. I wasn’t passionate enough about buy-to-let to find out.

What did interest me was design, development and technology. I immersed myself in the web industry. Attending (and speaking at) conferences, reading publications, engaging with the community…

All of this lead to the creation of Jack. I focused on freelance designers and developers—an audience I like.

Lesson: You’re going to spend years talking to, dealing with and serving this audience. Make sure you like them.

Don't Assume A Problem Exists

This is a common mistake creators make. Think about the developer who builds a SaaS app without researching their target market’s pains. Nobody uses the software because it doesn’t solve a problem that existed. It solves a problem the developer thought existed.

The developer has now wasted months developing this product, only to make no financial gain. This is a mistake that could have been avoided had they spoken to their target market.

I made this mistake, too.

Sales had taken a hit. With comparison sites booming and our diminishing visibility on Google, I had to ask, “What can I do to improve our figures?”.

While the insurance industry has improved, back then insurers weren’t investing money into their technology.

I believed that if I used design and technology to make the process simpler for landlords to buy insurance, we’d see an increase in sales. I focused on redesigning our quoting process. I built a rough prototype of a quote system from the little Ruby on Rails I had learned.

I hired a designer to redesign our website. I’m confident we were the first UK insurance broker to implement a responsive design.

I snagged the .co.uk extension. This symbolised our business maturing, laying to rest the .net extension and giving us more credibility.

I built Lodger, a SaaS app for landlords to manage their rental properties. It complimented our customer-base perfectly, and gave us a unique selling point.

Surely this would solve our problem of falling sales.

I took my Dad’s business from this:

How Brokers Direct looked when I inherited it
How Brokers Direct looked when I inherited it

To this:

The current version of Brokers Direct
The current version of Brokers Direct
The app I built for Brokers Direct customers
The app I built for Brokers Direct customers

But this didn’t produce the results I’d hoped for and we didn’t see a surge in sales. Why? There was something I had overlooked.

Responsive design, a nicer quoting experience… None of that really mattered to our audience.

Landlords don’t care about good design. They don’t get excited about clever technology. Landlords are content filling out a traditional proposal form on their desktop computer running an old version of Windows.

It took a long time to realise the problem I was addressing just didn’t exist for this audience.

Lesson: Research your audience’s pains. Don’t assume a problem exists. Talk to them.

Silver Linings

Whilst all of these factors contributed to the business not performing as well as it once did, I don’t see this as a failure.

I was able to use my Dad’s business as a platform to learn coding, marketing and about insurance. Through inheriting his business I developed a passion for design. I used my experience as a stepping stone to do something I love.

On the topic of failure, reflect on why it happened and what you can learn from it. Failing at something simply means you’re trying something new. Failing at something means you’ll do better next time.

It’s OK to fail.

My Dad’s business was the catalyst for Jack. Those lessons—as difficult as they were to learn at the time—are helping me build a better, stronger business today.

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