According to the year progress account on Twitter, we’re 55% of the way through 2019. Coupled with the start of summer being quieter for my business, now seems a good time to revisit some of the goals I set myself and do a mid-year review.

I didn’t spend much time refining my goals for 2019, but I was clear on what I hoped to achieve within the business:

  • Launch 3 new products
  • Reduce the excess on our existing products
  • Build community features
  • Develop our dashboard

Let’s take a look at each of these goals. Am I on my way to achieving them, have they evolved into something new, or have I shelved them completely?

Launch 3 new products

In February we launched the legal expenses product. This provides legal advice, a solicitor to chase overdue invoices, loss of earnings from jury duty and more.

2 months later I wrote about the ‘disappointing’ result of the launch. 5 months post-launch I’m hesitant to refer to it as disappointing, but it hasn’t set the business alight in the way I thought it would.

I believed this product would inch us towards product/market fit because it provides upfront value to customers instead of being a product that’s triggered only when there’s the threat of being sued. I was wrong.

There have also been some issues around the policy wording. We’re in the process of addressing this to make it clearer, but there was nothing smooth about this product launch.

With one down, how do the other two look?

Well, the other products hinge a lot on this binder I’ve been talking about for a long time.

Once and for all, let’s clear up what this means is and why it’s so complicated.

The binder allows me to build a self-service checkout for insurance. At the moment I arrange policies via the insurer’s e-trading platform, but this is limiting in terms of what we can do with the customer journey and what products we have access to.

A binder gives me the scope to sell policies direct from With Jack’s website and build more products into it from different providers.

This is what I wanted to launch with 3 years ago, but because I started with nothing (no existing customers, funding or experience) I began at the bottom and worked my way up. I didn’t think I’d still be manually binding policies almost 3 years in (I’m selling £14,000 of products per month this way).

Nothing in insurance is easy, so the application process is lengthy and depends on third-parties to push it along. The more third-parties you have involved in something, the slower and clunkier it becomes.

The reality is it may not be 2019 the application is approved, but in the meantime we’re doing what we can on our end to get things ready. This means planning and building the infrastructure.

So, 1 out of 3 products so far. Is it likely I’ll have the other two launched by the end of the year? Considering how slow this binder application is moving, it would take a miracle. But miracles do happen.

Reduce the excess

When visiting London at the start of the year I asked the insurer if we could reduce the excess on the contents policy. Most of our claims are for contents and the excess feels steep for freelancers. Especially when many of them are claiming on a single laptop or phone.

We agreed on piloting a lower excess with a small pool of customers. If the results aren’t adverse we can roll the lower excess out across all policies.

However, this depends on—you guessed it—the binder.

Build community features

All of my customers are in similar industries to one another. They face the same problems, have to learn the same lessons and share the same worries. It would be beneficial to bring them together in some way.

I have a few ideas around community features and I want to test them in true MVP style. As in, build a scrappy prototype and see if it has legs before investing money into a slick design and a professional developer.

It’s been a long time since I coded, but earlier this month I signed up to SuperHi for an intermediate Ruby on Rails course so I can brush up on my skills. This is with the goal of building and testing my ideas for community features.

(Slightly off topic, but I love everything about SuperHi. The brand, the format, the content. Check them out if you’re interested in learning how to make digital products.)

These features are something I can explore as I patiently await progress with the binder.

Develop our dashboard

Not much build progress has been made… yet. We’ve done some brainstorming and I’m visiting Scott, my designer, in Nottingham next month to spend the week working on this. Both of us have interesting ideas around the dashboard, but some of them involve… yep, the binder.

Without giving much away, the next update will center around after-sales care. A big problem I’ve noticed is how few freelancers understand their insurance. A lot of them have problems insurance could help with, but they don’t realise that. Some of my customers have been in situations where they could have used their insurance, but they didn’t know this. This isn’t their problem to fix—it’s our fault (insurers and brokers) and the next update will focus on addressing this.

A lot of insurers focus on pricing to win customers. It’s important to me to push the value of insurance and get away from the price-driven buying behaviour that plagues the industry. The only way to do that is to help people understand the products they’re buying.

If you want to keep track of the progress we make whilst I’m in Nottingham next month, follow me on Twitter.

Binder, binder, binder

Most of my work goals depend on the binder, which isn’t progressing at the pace I want it to. I’ve said it before and I’ll say it again—if you want to move fast and build quickly, don’t start a business in the insurance industry.

A lot of startups are drawn to financial services because of the potential to improve on the industry incumbents. However, even as a startup your business will have to be part of a traditional players’ ecosystem.

This, alongside the red tape of it being a regulated industry, will slow you down.

You may be able to offer faster customer support or better tech, but a lot of the important processes are rooted in incumbents. The solution is to become a carrier a la Lemonade, but you need multi-millions of pounds to do that (Lemonade has raised a total of $480 million).

The reality of bootstrapping is that you move a bit slower than, say, a VC-backed startup with millions in the bank that can be thrown at more staff and a higher output of features, products etc. Couple that with building in an industry that doesn’t (or can’t) move quickly and the outcome can be frustrating.

I don’t exactly help myself. There are some things that would enable me to move quicker:

  • Having a full-time developer. I work with freelancers, but having someone in-house on a permanent basis would help push new features and updates out the door on a more consistent basis
  • Better project management skills. I’m inexperienced with how to manage projects, oversee a team of people, set milestones and ensure we meet them in a timely manner and are aligned in our vision. SuperHi have just announced a digital project management course, so I’ll likely take that
  • Building in a different industry altogether. Having the freedom to move quicker, not depend on incumbents or have to navigate regulatory constraints would be wonderful. But it’s insurance that I’m passionate about and I believe I have unfinished business here so I have to live with these pitfalls

But I continue doing what’s been working for me so far. Putting my head down, and day-by-day making progress towards my goals until I eventually get there.

Despite not having checked off any of these goals at 55% of the way through the year, I’m not unhappy with my progress. Whilst momentum has been slower than I’d like, a lot of important foundations are being laid and I think everything will start to come together.

P.S. This mid-year review has been beneficial in letting me see my progress (or lack of in some areas) and what I can change in the latter part of the year. I recommend revisiting your goals mid-year to see where you stand and what you can change to give yourself a better chance of reaching them.