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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How I Won My First 3 Customers

How I Won My First 3 Customers

When I launched Insurance by Jack in 2014, I struggled to win sales.

One week passed… nothing. Week two… zilch.

It took me three weeks to make my first sale. It was a slither of momentum, but it wasn’t the start of my business gaining steam.

I knew why I was struggling. Insurance by Jack had a strong brand, but the process of getting a quote involved a third-party form. This resulted in a customer journey that wasn’t cohesive and made for a poor user experience.

Fast forward two years, Insurance by Jack has evolved into Jack and I’ve been granted more permission and responsibility. Now that I’ve taken control of the design and technology, I’ve created a customer journey that compliments Jack’s brand.

The theory that this would improve sales was true. So much so, I made my first sale three weeks before I launched. A stark contrast to 2014’s launch to crickets.

Last week I celebrated putting my 50th freelancer on cover, but I want to start at the beginning and share how I won my first three customers.

My First Customer

In the run up to launch, I replaced Insurance by Jack’s website with a landing page. I wrote a couple of paragraphs on my vision for insurance, which I followed with a call to action to be notified of launch.

Jack's landing page
The landing page that replaced the original website

120+ people opted in. This surprised me because it’s insurance. Having 10 people pay attention would have been a success.

I sent 3 emails to this list.

1. Coming soon: The new Jack. I touched upon my journey in insurance and detailed what people can expect from the new Jack.

2. Want to test the new Jack? A short email asking for beta testers. 29 people responded.

3. Introducing the new Jack. The soft launch email. I announced I was open for business.

Designers and developers love collaborating. They enjoy seeing other people’s work and offering solutions as to how they’d approach it differently.

Email number 2—where I asked people to test the quote form—was the ideal way to open dialogue with my target audience. Not only did I get constructive feedback on the process, but several people actually wanted to buy insurance.

This is how I won my first customer before I launched.

Lesson: Involve your target audience in the build process. At the very least be transparent about what you’re working on—people will take an interest and want to support you.

My Second Customer

I quietly pushed Jack live from a hotel room in Berlin with terrible WIFI.

When I say quietly, I didn’t announce the service was available. I deployed it to GitHub Pages, walked away and played tourist in Berlin.

The following day I checked my CRM tool and was surprised to see a quote had come through. It was from a name I recognised.

This person had been following me on Twitter for years. Our first exchange was 5 years ago—back in 2012! This was two years before I had even started my crusade into business insurance.

Lesson: Marketing is about the long game. Relationships established years ago can blossom into paying customers.

My Third Customer

By this point I still hadn’t announced I’d launched Jack. I was aiming to do a few weeks in soft launch, so I was expecting any quotes that came through to be from beta testers.

During this time I gave a talk at Hybrid, a conference for creatives.

With the first iteration of Jack (Insurance by Jack), I had no control over the customer journey. I had no idea who my customers were or where they were coming from. It made tracking marketing very difficult. Especially public speaking.

As a quote had come through from someone that wasn’t a beta tester, I asked where they’d heard of Jack.

We heard about Jack through friends that'd been chilling at Hybrid. We looked at your site and we're suckers for a good design. Truth be told we'd never thought about insurance, but the site was fun, friendly and didn't feel like chewing glass.

What do you know, public speaking can convert. Thanks to the HybridConf attendee who passed along Jack’s name.

Lesson: Share your story everywhere. All it takes is for one person to hear it and share it with their friend.


I won my first three customers through the following channels:

  • Beta tester
  • Twitter
  • Public speaking

I’m having a lot of fun building Jack and finding ways to win customers, but I do need a better formula.

I’m heading to Switzerland for my birthday in a few weeks for a (working) holiday. One of the books I plan on reading is Traction. I’m hoping to use their three-step framework to discover the best channels for marketing Jack.

Hopefully one day I’ll be writing about winning my 3000th customer, but I’m documenting my journey of building an insurance business from the start.

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My Goals For 2017

My Goals For 2017

Every year I’m guilty of setting too many goals (and vague ones at that). ‘Be more successful’, ‘Earn more money’, ‘Get fitter’. This year I’ve put more thought into defining my goals.

Business, creativity and fitness are the themes of the year.

#1: Add more cover features to the quote system

I launched with one product, professional indemnity insurance. This is the most common type of cover for freelancers and it kept the build process simple for the quote system. Lean startup and all that.

After giving 160+ quotes and putting 47 freelancers on cover, I have a better idea of what cover they commonly require. Worldwide cover, contents insurance and public liability are often requested.

Now I have access to a wide suite of insurance products, I’ll be building these into the quote system.

It’s a win / win situation and my priority going into 2017. I earn more commission per policy, and freelancers can customise cover to their individual needs. I know I’ve lost sales due to the quoting process focusing solely on professional indemnity.

Where the money to invest in this will come from is another blog post for another day. (Fun fact: Jack is bootstrapped on £10,000 I earned photographing weddings.)

#2: Build a dashboard for customers

Customers will be able to login and access their documents, freebies and have an overview of their insurance.

I’m going to hack on this project solo to keep costs down (but hire a designer). I’ve built a Rails app in the past, and I spent the Christmas period brushing up on my Ruby skills… and levelling up in Dragon Age: Inquisiton.

I can already envisage it being a frustrating project to tackle, but I’m open to the challenge.

#3: Create a referral scheme

A lot of my first customers have come from referrals. This is handy because Jack is bootstrapped and I’m marketing on a tight budget.

I haven’t put much thought into the referral scheme just yet. It will, of course, begin with asking customers, “What can I do to encourage you to recommend Jack to your friends?”.

#4: Double the number of policies I'm selling

At the moment I’m putting 2-4 people on cover a week. This works out at 150+ customers after a year. I’d like to get to 300.

Right now this feels unlikely, but it’s a numbers game, right? With a conversion rate of 26%, it means I need to deliver 1200-odd quotes to get to 300 customers.

Now to attract thousands of freelancers primed to buy insurance to Jack’s website. That won’t be hard. /sarcasm

#5: Run a half marathon

In October I started training for a half marathon. No race in particular, but I was inspired by Chad’s 27.2 mile jaunt around Chicago. After running four 10K’s in the space of a year, I knew I needed to step up to the next milestone.

I’ve never enjoyed running, but following a training plan on Runkeeper has (mostly) kept me on track. I did contract the flu on Christmas day, so I’ve fallen a little behind with the plan. This sucks because Santa brought me new trainers.

My goal for 2017 is to sign up and run a half marathon, finishing around the 2 hour mark.

#6: Sit my next insurance exam

In March of 2016 I sat and passed my first insurance exam. Studying for this was as painfully dull as you’re imagining.

Although it doesn’t benefit my career right now, it’ll come in handy down the line when I’m aiming for full authorisation (I’m currently an Appointed Representative with limited responsibility).

The best approach I found to studying was blocking out 30 minutes a day. No intensive 2-3 hour sessions, otherwise I wouldn’t do it. I love the challenge the insurance industry presents—not the ins-and-outs of the industry itself.

#7: Do a photo project

One thing I slacked on in 2016 was photography. I shot a lot of weddings, but I didn’t take many photos for me. My blog was updated only 33 times. Compare this to 2011 when it was updated 149 times, it’s clear I’ve fallen behind on doing photography for fun.

I tell people who are just getting started with photography to carry their camera everywhere for 30 days. I need to follow my own advice, so I’ll be doing a project that requires a degree of commitment.

I haven’t decided what that project will be yet. I’m open to suggestions (but no Project 365, please).

My ultimate aim for 2017 is for Jack to be delivering instant quotes and cover. I can only get there if I’m generating enough business for an insurer to consider giving me their rates to plug into my system.

It costs an insurer a lot of money to onboard a broker, so they need to ensure it’s worth their resources. If I keep building my book of customers and focusing on creating a good customer experience, I’m confident it’ll happen.

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Jack's Year In Review

Jack's Year In Review

Maybe 4 months in business is too soon for a ‘Year In Review’, but I’m a sucker for those posts (and I’ve learned a lot in 4 months).

I quietly launched Jack at the tail-end of August. I was sitting in a hotel room in Berlin with my sister. After a bumpy few years getting Jack off the ground, I deployed the code to GitHub and went out to explore the city. Great city, by the way.

To finally implement my own design and technology (a work in progress) after years of trying… I can’t describe how it felt! It’s the beginning of building the company that’s been swirling around in my head for years.

This journey is just as fun as I thought it would be, but also a lot tougher. Guys, business is really hard. I have respect for anybody working on their own thing, because it isn’t easy.

I had a taster of it with Insurance by Jack, which was made all the more challenging by building on top of someone else’s platform. No access to data, no control over the customer journey, not knowing who my customers were or what marketing channels worked.

Building a business is challenging enough, but doing so without creative control or access to data? Impossible.

Anyway… let’s get into this.

Almost 4 months in Jack has 41 customers. They’re evenly split down the middle with designers and developers, then there’s the odd marketer and consultant.

Top Sources Of Traffic

I’ve tried various methods of getting traffic (cheaply). Facebook and Twitter, banner ads… What’s worked best has been our Designer News and Product Hunt features.

As a result, I’ve decided to cut back on ads and focus on tools and creating value. For example, I launched a business health checkup tool that assesses the vulnerability of your freelance business. I’m sharing it with communities like Designer News.

Spikes in traffic
Spikes in traffic since launch

Marketing insurance is about planting a seed. It may not be a freelancer’s time to renew, so they’re not yet ready to get a quote with Jack. This is why I find push marketing less effective.

Provided I can get Jack in front of the right people, I’ll plant that seed for renewal time. That’s what micro-sites like the business health checkup tool are helping me do. I’m playing the long game.

Tools For Building Jack

These are the tools I can’t live without. I wrote about Pipedrive and my CRM tool in more detail on another blog post.

Pipedrive is where I track my sales funnel. 4 months in I’ve given out 152 (legit) quotes and 508 fake quotes. Pipedrive is where I keep track of the genuine leads and at what stage in the funnel they’re at. I add customer details, whether I’ve followed up for a second or third time, and reasons I’ve lost a lead.

As more leads come in, Pipedrive is invaluable for keeping track of everything.

Google Analytics is ugly but does the trick. I’d love to use something aesthetic like GoSquared, but it’s expensive.

Analytics does everything I need it to. I make the most of it by setting ‘Goals’ and tracking them. I can see which blog posts convert readers into customers. (These two, if you’re curious.)

Top Expenses

  • Design
  • Development
  • Insurance

All of the money I’ve made has been reinvested into design and development. For example, building the business health checkup tool and the quote system.

Next I’ll be investing money into the quote system. The aim is to pad it out with additional cover and features based on user feedback. Most of our customers require worldwide cover due to working with clients, for example, in the US. It makes sense to build this—and other regularly requested features—into the quote system.

My other expense has been insurance. If you thought arranging insurance for your business sucks, try arranging insurance for your insurance business.

Proudest Moment

In October I was shortlisted for an award at the Digital Insurance Awards 2016. The Rookie Award, to be precise. The ceremony took place on November 18th and I won!

The image at the top of this blog post is of my award. It’s an alarm clock. #wakeupinsurance is the event’s hashtag. Wakey, wakey. Alarm clock. Get it?

What Didn't Go Well?

I took a gamble by taking out an ad for Black Friday. I spent £235 on the ad plus £180 on the product I’d be giving away. It got me one sale. That’s £26.25 in commission. That’s a loss of £388.75. Ouch.

Making mistakes is inevitable, as long as they’re occasional. Next time I try throwing money at ads, talk me out of it. At this early stage that money is better spent elsewhere.

Cold, Hard Stats

  • 16,449 Visitors
  • 153 Legit Quotes
  • 41 Customers
  • 26% Conversion Rate
  • £10293.93 Gross Premium Written


Despite being an introvert, I can’t say I enjoy being a ‘solopreneur’. I’d love to have a co-founder or partner to share this rollercoaster ride with. It’d help having someone onboard with a skillset I don’t have, like a designer.

Fortunately, I’m a member of a community of product people. It’s run by Justin Jackson. You may see me tweeting his stuff often (and I’ve even linked to his blog in this article), but it’s because his content is gold.

I was also a member of Fizzle for a while. I cancelled my membership to cut back on expenses.

It’s worth joining a community of people in the same boat if you’re a solo founder. They hold you accountable with shipping, and after launch you’ll get feedback and advice on marketing.

It’s not the same as having a co-founder, but it helps me to feel a little less ‘solo’.

What's Next?

I want to grow Jack into a community for freelancers. To have a body of designers, developers and more, it seems wasteful to not build in community features. A forum for discussion, a job board, accountability or collaboration features… I don’t know yet. If there’s anything you’d like to see from Jack, let me know.

My big goal is to punch an insurer’s rates into my system so quotes and cover are instant. I hope I can make that happen in 2017, but it all depends on the volume of business I continue placing.

I want to thank those first 41 customers! Jack doesn’t have many features right now–it’s pretty barebones. It will get somewhere, but not without support from designers, developers and other freelancers.

Looking Back

This jumped out at me when looking over my 2015 review:

I’m confident that with the effort I put into phasing out distractions in 2015, I’ll have a more focused and productive 2016.

2015 was all about phasing out distractions and focusing on insurance. It felt like a quiet and uneventful year, but it ultimately lead to launching Jack in 2016. With that said, 2016 was just a warm-up for Jack.

I’ve dipped my toe in the water. I like it. I’m going all in.

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The Number One Reason I Lose Sales

The Number One Reason I Lose Sales

An upside of manually processing quotes is striking up conversation with potential customers. If a quote doesn’t convert to a policy, I get to ask why.

The most common response is:

“Your quote was more expensive than others. I got it cheaper elsewhere.”

Now that I know price is the biggest factor I’m losing sales, surely there’s something I can do about it? Of course. I can work with a cheaper insurer or cut my commission. But I’ve chosen not to do either of those things.

Why Would I Want To Sell A Cheap Product?

I take pride in offering a good policy, and working with an underwriter who has a reputation for paying out claims.

Jack’s metric for success isn’t just commission—it’s trust. I won’t offer a cheap policy that doesn’t pay come claim time. Perhaps I’d earn more money in the short-term, but there’s something more important at stake here. Building a business I’m proud of and earning customers’ trust.

When I think of the investments I’ve made to launch my business, did I hire the cheapest developer to build Jack? The cheapest copywriter? No way.

I didn’t have the biggest budget, but I still invested in talent—in my business. Fiverr could have saved me money, but I paid for a premium service because I wanted an experienced team I could trust. I wanted quality. It’s a no-brainer.

Why is it different with insurance? Why is cheaper considered better when buying a policy?

It isn’t.

This thought process is an unfortunate by-product of the popularity of comparison sites. They’ve encouraged a buying behaviour of judging insurance solely on price. You don’t look at policy features, company reviews or customer service. You look at a table of prices and select the cheapest.

Comparison sites have been around for over a decade. Jack has been around for 2 months. Challenging a behaviour that’s been ingrained in buyers for over 10 years is proving difficult.

Taking A Smaller Commission

The alternative to not selling a cheap policy—but still competing on price–is to cut my commission.

In some instances I have done this. When someone’s made it clear they’re keen to buy but the price is slightly out of their budget, I bring my share down.

But that’s not a solution. I’m not earning bags of money from each policy I sell. For £100,000 of cover I earn a modest £26. For higher levels of cover, I can net between £40-70 commission.

I’m in this for the long-term. I want to build Jack into a sustainable business, therefore I must operate as a business and earn money.

Commission is what enables me to keep working on Jack. Not just for Jack to exist, but to blossom into the business I’ve always dreamed of. Right now it’s a tiny version of what I envision it to become.

That’s not going to happen if I don’t earn money to pay myself and reinvest into the business. Nor will it happen if I sell a cheap policy that lets people down when it comes time to making a claim.

That Was A Nice Rant. Now What?

There are two, big challenges I’m facing with building an insurance business.

  1. The audience I serve is still relatively new. Insurers haven’t been targeting freelance designers and developers, so information on how insurance applies to them and what problems it solves is sparse. I’m working on addressing that
  2. For those who understand the role insurance plays, I’m fighting with the price-driven buying behaviour. Jack isn’t overpriced. We might charge an annual premium of £160 for £100,000 of cover while a competitor charges £120. That’s only a £40 difference, yet it matters when people are simply looking at price. What about the more important factors? Better cover with additional features, customer benefits or quality of customer service

I don’t think there’s a quick fix, but I know it falls on me to better communicate the value of insurance. Like I said, it’s tricky challenging a well-ingrained buying behaviour.

I do know I’m not going to sell a cheap policy. 73% of people don’t trust their insurance provider and I don’t want to contribute to that statistic. In fact, I want to work towards turning that statistic around.

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