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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Start With People

Start With People

Let’s begin with the good news. I’ve put 20 freelancers on cover already, which is over £5700 Gross Premium Written. This is 20 freelancers Jack is helping build a bulletproof business. Yay!

Secondly, I’ve been shortlisted for two awards at the Digital Insurance Awards 2016. ‘Young Insurance’ and ‘The Rookie Award’. High fives all around.

The whole point of this blog, however, is to cover the challenges I face as well as triumphs. I’ve received a few emails from people complimenting me on my transparency, specifically when writing about building Jack.

Now I’m into Jack’s full second month of trading… and it’s hard. I’m realising just how challenging it is to market and sell insurance, especially as a newcomer to an established industry.

  • People are used to instant quotes and cover. I have to manually process everything (for now)
  • People expect cashback perks and financial incentives. I have a modest list of benefits
  • Most people choose their provider based on price (a by-product of comparison sites). I don’t sell a cheap policy, so I’m missing out on sales. But I’m OK with that, I don’t want to sell cheap stuff—I want to sell a good policy from an underwriter with a reputation for paying claims /rant
  • People are primed to buy insurance just once a year. I don’t have a database of renewals to tap into

Things have slowed down in my second full month of trading.

This is because I’ve burned through my ‘immediate network’. It’s a lame term to describe my friends in the industry, Twitter followers, email subscribers etc. Those who have watched as I’ve built Jack and were ready to get on-board from the start (thanks, guys!).

Now leads are generated from paid resources, ads and organic search. That’s fine, but these leads require more of the ‘hard sell’.

In hindsight, I’d have approached things differently to make post-launch easier. I wasn’t nearly as active in the build-up to launching Jack as I could have been.

A Different Approach

If I could start all over again I’d do the following:

I wouldn’t think about what I’ll be selling down the line or the business I’m going to build. I’d pick a group I want to serve and spend a solid year focusing on that audience. No getting distracted with selling or developing a business—I’d channel all of my energy into helping, researching and speaking to that audience.

I’d start with people (freelancers)—not the idea (business insurance).

I’d go to conferences, attend meet-ups, blog regularly and participate in communities. I’d do only this for a whole year. No product to sell, no business to pitch. Just listen, research and grow.

I did some of these things to a degree, but lacked the consistency needed to produce the best results.

By the time Jack had launched, I had 4000-odd Twitter followers (not all freelancers) and 200 email subscribers. There are many things I could have done to double, triple or quadruple these numbers, yet I focused on building my business instead of relationships.

That’s stupid—you can’t grow a business without relationships. Post-launch would be a little easier had I started with people.

Justin Jackson is a perfect example of starting with people. Justin didn’t launch a paid product for an entire year. Instead he focused on creating content, participating in communities and helping an audience of product people. Now he has a sizeable network ready to buy whatever he’s selling.

Hindsight is a powerful thing. I wish I’d set aside a year to research, help and build an audience of freelancers. What’s a year in the grand scheme of business?

Maybe you’re just starting out. Perhaps you don’t have an audience, idea or product yet. My advice would be to pick a group you know you can serve, and spend a solid 6-12 months researching, helping and growing that audience.

Don’t get distracted with selling, just focus on helping and serving the network you’re building.

Start with people.

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Post-Launch Problems

Post-Launch Problems

If it was easy everybody would be self-employed. Last month I launched Jack, so what issues have I faced with the first month in business?

That Post-Launch Traffic Slump

Launch day (or week) brings a surge of traffic.

Launch week traffic
Launch week traffic

You’ve shipped something new, people are eager to check it out. They’ll tweet about your product, share it on Facebook or mention you on their blog.

You might even get ‘Hunted’ or featured on Designer News. The really smart people will have built a list of loyal followers to launch to.

If you’ve done things right in the build-up, launch day will do the work for you when it comes to driving traffic.

Jack experienced a surge of traffic during launch week, which in turn brought leads. Lots of ‘em. Some of those leads became my first customers.

But what happens when launch traffic dries up? You need to find a way to keep a steady stream of traffic (and leads) coming in. How do you do that once the initial buzz has died down? That’s what I’m trying to figure out.

Understanding My Audience’s Preferences

My goal is to make insurance simpler. I may be biased, but I think Jack’s quote system ticks that box. It asks the questions it needs to get you a quote—nothing more.

All insurers have different question sets for cover. Some demand endless forms to be filled in, while others require a few key details. We work with an insurer who falls into the latter category, but it comes at a cost (quite literally). Higher premiums.

Recently I added another insurer to my roster. While their premiums are cheaper, they request a lot more information upfront—some of which doesn’t feel relevant for freelancing. It doesn’t jive with the simple, freelance friendly process we’re creating at Jack.

But maybe I’ve got this all wrong. Perhaps freelancers are willing to spend an extra 15 minutes when buying insurance to save money.

Should I compromise on Jack’s ethos to give my customers access to cheaper premiums, or do they value convenience and simplicity more?

This is a difficult question.

Balancing Everything As A Solo Founder

All of my processes are manual. In the future I’ll be automating tasks, but for now I’m doing and handling everything myself.

I manually issue quotes and cover. I personally follow up on last week’s quotes, or remind customers to fill in their risk questions. Y’know, the general admin of running an insurance company.

Some days are quiet in terms of leads coming in, but with busy periods these processes can eat into my day. It’s not uncommon to get to the afternoon and I haven’t managed to do the work that’ll attract more business.

I haven’t sent that newsletter, written that blog post, published those adverts, updated social media etc.

Starting A Business In An Industry That’s Hundreds Of Years Old

A lot of insurers have been around for a long time. They’re decades old. They’ve had years to hone their processes and improve their product.

Jack is one month old, yet I’m competing against insurers who have decades of experience.

This can work in my favour—the industry needs fresh thinking and ideas. But at the moment, with starting a company from scratch, Jack is a little lean compared to its competitors in terms of features, tools and benefits.

How do I convince people to get onboard with a new business?

These Are Good Problems To Have

  • Keeping traffic flowing post-launch
  • Finding out what’s important to my customers
  • Balancing bringing in new business with binding new business
  • Getting people onboard with a new company

It’s taken me a long time to launch Jack, so I’m happy to be having these ‘problems’. It’s fun figuring this stuff out.

I’ve been in business long enough to know that it never does get easy. Challenge accepted.

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Tools I Use

Tools I Use


Pipedrive was recommended to me by Justin Jackson. It’s the tool I use to track my sales funnel.

Who’s got a quote? Have they received the risk questions? What deals have I won? All of this is logged in Pipedrive.

Using Pipedrive to track Jack's sales funnel
Using Pipedrive to track Jack's sales funnel

My sales funnel looks like this:

Lead In > Contact Made > Quote > Risk Questions

Since Jack launched I’ve processed 70+ quotes, all of which are at various stages in the funnel. On average it takes 5 days to close a sale. I’d be lost without a means of tracking quotes.

Cost: £120 per year

Custom-built CRM

Scott has been a dream to work with. Not only did he design and build Jack’s quote form, but he created a CRM tool to integrate it with. He’s one talented guy. Hire him.

This is where all of the quote data lives. I’m notified when new quotes come in and each one is assigned a unique code.

Jack's custom built CRM tool
Jack's custom built CRM tool

If the customer wishes to progress to the next step, I can send the risk questions from the CRM tool. The unique code tracks who has answered them.

We built this on a shoestring budget. It’s super lightweight and very much a MVP, but it does what I need it to do—no bells and whistles.


Next year I’ll be processing quotes and issuing cover instantly online. In the meantime, there are a couple of extra steps involved with manually processing cover.

Every customer has to sign a ‘Statement of Fact’ document once they purchase insurance. I forward this to the insurer.

Imagine a digital insurance company needing you to print, sign and return a form in the post? Ain’t nobody got time for that.

Fortunately, DocuSign takes the pain out of signing documents.

Cost: £183.60 per year

Invoice Machine

Lastly, if everything goes to plan the insurer (and I) need to get paid.

I’ll earn between £35 - £52.50 commission depending on the premium. Premiums for web designers / developers are quite small, so I’m averaging about £40 per sale.

Cost: $12 per month

Jack’s only been live for a couple of weeks, so I’m still testing the water as to what apps work for me. If you have any alternative suggestions or know of any tools that would make my life easier, let me know on Twitter.

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