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 With 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,, 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 With 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 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, or using an old school broker to find them the best deal.

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 With Jack. Those lessons—as difficult as they were to learn at the time—are helping me build a better, stronger business today.