Two years ago I wrote about the problems I was facing post-launch. I thought it’d be interesting to revisit this article and see how I’ve solved those problems or if they still exist.

Understanding My Audience’s Preferences

In 2016 I asked the question, “Should I compromise on With Jack’s ethos to give my customers access to cheaper premiums, or do they value convenience and simplicity more?”.

I was asking this because I had the option to work with a cheaper insurer than the one I launched with. I had a few concerns about it.

  • It was a cheaper product (shoppers think this is a good thing, but it’s usually cheaper for a reason. Less cover, fewer features)
  • They required a lot of information upfront to determine your eligibility, making the sign-up process lengthier
  • Their reputation for paying out claims wasn’t great

To me it was a no-brainer. I should work with the insurer whose onboarding was slicker and had a good reputation for paying out claims, even if it was a more expensive product.

It was important to establish With Jack as the best fit for freelancers, and that meant being mindful of the insurer I partnered with and carefully selecting the product I sold.

Customers shouldn’t just have a nice experience when buying insurance. Their insurance should come through for them if they ever need to make a claim.

Post-launch, the harsh reality became evident quickly. Most people don’t perceive the value of insurance, which means price is the top of their list when shopping around. Even though I didn’t want to be known as the cheapest or judged purely on price, I knew I was battling a price-driven mindset that’s been established for years.

In the end, I decided to stay with the insurer with the more expensive product. Why? It’s important to me that:

  1. I build a profitable business that will still be here next year. That means not being the cheapest
  2. My customers have faith their claims will be paid out. That means not offering the cheapest product
  3. The customer journey is as painless as possible. That means asking fewer questions

Fortunately, the insurer established a better price point because of the feedback I was getting about price. They dropped their premiums by half in some cases.

The more business I bring them, the more scope I have to negotiate and make adjustments that better suit my customers.

I’ve never regretted that choice. We’ve since had several customers make a claim and I have confidence in the way they’re handled. My customers are in good hands and that’s the most important thing to me.

Yes, there are competitors undercutting me and I lose some sales to them. There always will be. But it’s doubtful that—unless they have the volume to sustain that—they’ll be in business long-term.

I still battle issues with pricing, but I think that will always be part of this industry. The goal is to bake more value into With Jack so people aren’t exclusively focused on price.

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 ended up manually processing quotes for another 2 years after writing this. I’ve worked out that I’ve:

  • Sent 800+ quotes
  • Spent 2500+ minutes processing them

In fact, I didn’t ship instant quotes until last month. This means the leads that now come through the system are likelier to convert, instead of those just shopping around.

I knew things would feel quieter when we shipped instant quotes. There’d be less work for me to do on that front. But that’s a good thing—it frees me up to focus on the work that will bring people to the site. We’re one step closer to automating the whole customer journey and removing me entirely.

Despite there being less work involved, it’s still tricky balancing everything as a solo founder. Admin, sales, marketing, customer support… I do it all and some days it can be rough.

That’s not even factoring in the emotional burden of being a solo founder. I wrote about this recently. There’s nobody to pick up the slack so you can get the rest you need to recharge your batteries.

Again, I think this is another problem that never goes away. Shipping instant quotes may mean I’m freeing up my time processing all of the dead leads that come in, but there are still a lot of plates to keep spinning.

Automating part of the customer journey is a step in the right direction because it removes me from a time-consuming part of the business, but being a solo founder will always have its challenges.

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

“With Jack is one month old, yet I’m competing against insurers who have decades of experience. How do I convince people to get onboard with a new business?”

I thought this would be my biggest problem post-launch. In hindsight, it’s not been as big a problem as I’d imagined.

My concern was that my competitors:

  • Are household names therefore appear more trustworthy (are people concerned about insurance start-ups not being around in a year?)
  • Stocked lots of products
  • Built all of the tech to automate everything from buying policies to submitting claims
  • Offered value added services to deliver more worth to customers

And there I was. Launching with just one product (professional indemnity insurance) and manually processing quotes. How would I ever compete?

Two years later it’s clear I could compete. I’ve built a business. I’ve signed up hundreds of customers, added more products to my line (and will continue to do so), shipped instant quotes with lots more features to come.

I think a lot of what helped me get through the first year as a new business was the work I’d put in beforehand. In the years leading up to With Jack, I attended and spoke at web conferences and meet-ups. This helped me build a small network of people in that world.

Speaking at Pixel Pioneers in Belfast.

When it came time to launch With Jack, many of these people were my first customers or helped to spread the word. I wish I’d put more effort into that, because I would have had an even stronger start.

New Problems

I’m moving into a new stage of With Jack’s life. Whilst some of these problems may not be as profound as they were two yeas ago, there are other obstacles as a result of being in my second year.

Remain Bootstrapped or Take Investment?

This is on my mind every day now I’m in my second year. I’ve proven I can build a business. With Jack is shipping £10,000+ of insurance products a month. What next? My heart says to remain bootstrapped, but the reality is I’m not moving quickly enough with features and products.

An opportunity recently arose that I could only take had I sought investment. I’m aware that I’d be building a very different business if I chose investment, and that’s what I’m apprehensive about.

Bootstrapping With Jack means I can always put my customers at the centre of the decisions I make. I’m worried that taking investment means the goal posts shift and you have people involved with a conflict of interest (i.e. customers aren’t at the centre of decisions—ROI is).

Making That First Hire

I’m hoping that 2019 will see me make my first hire. This is new territory for me and is terrifying. It makes the business even more real. I’ve worked for myself and on my own for 10+ years. Whilst making my first hire would be an exciting step forward, it would bring new challenges.