Last week was challenging. Personally and professionally I felt worn down and tested. It was one of those moments where I question why I’m doing this. Those times don’t happen often, but when they strike they are debilitating.

Breaking into the insurance industry is tough. Doing it as a self-funded, solo founder is crazy.

A few things aggravated me, but a big source of stress came from my delegated authority application. If approved it means selling policies from With Jack’s platform instead of manually processing quotes.

(Fun fact: I’ve manually processed £200,000 of quotes. This equates to 45 consecutive hours at a computer. One of those quotes was from on top of a volcano in Spain!)

I can’t emphasise this enough, but insurance is not start-up friendly. It’s heavily regulated, capital intensive, low margin and highly competitive. It’s times like this—with the red tape and paperwork—that test me.

I can admit my strengths and weaknesses. Filling out applications, writing business plans and financial projections is not my strength.

There were a lot of spinning plates last week and I don’t have a co-founder to split the workload with. It all got on top of me. This lead to me questioning why I didn’t choose an easier industry, or why I’m building a business altogether.

The Start-Up Rollercoaster

It doesn’t actually matter what industry you build a business in. There are always going to be moments of self-doubt and questioning your sanity. Irrespective of sector, building any kind of business is hard work.

This paragraph from the Baremetrics blog nails it.

"I always remember one of the first days we started working on our business full time in a coworking space in London and someone who had done it for a while came up to me and said “be prepared to find out what it’s like being bipolar” — it’s always stuck with me as a reminder that it always gets bad, but you’re on the journey because the highs make up for the lows"

Last week was one of the ‘lows’. I was juggling multiple balls at work, working to various deadlines and trying to complete my application. I’ve put a lot of pressure on myself regarding the latter. In my personal life, my flat had flooded and I was living in a building site. I felt a bit fed up.

Fortunately, I was reminded of why I’m doing this in the form of a post-it note I wrote in December 2013. This was when I first started thinking about what would become With Jack. It summarises my motivation for starting my own business in the insurance space.

It needs to be human, it rewards loyal customers and the technology doesn't suck.

It addressed some of the problems I was noticing in insurance at the time. Such as:

  • 74% of insurance companies see technological innovation as a challenge, but few are developing their own offerings in-house or partnering up with start-ups.
  • 73% of consumers don’t trust their insurance provider.
  • 2 out of 3 customers are unhappy with their journey through buying insurance.

Basically, the technology sucked and insurers weren’t customer-focused.

Solutions Are Born From Frustrations

When I wrote this post-it note, I had been working in insurance for 8 years and was frustrated with the industry. I wanted change and started exploring how my own insurance business would look.

My insurance company would be human, I thought. Nobody needs another faceless corporation. Let’s drop the legal jargon that litters the buying experience. People should understand what they’re paying for. I’d build it with modern technology and good design instead of the legacy systems insurers are locked into. Loyal customers will be rewarded. We’re accustomed to rising premiums every year even when we haven’t claimed. Why do insurers punish us for being loyal customers? They do a great job of making us feel unappreciated.

During last week’s slog I returned to this post-it note. It was a reminder of my motivation for starting With Jack—the ‘why’ behind it—and served as a sanity check during a tough week.

I remember writing this. I was working from Toad’s Caravan and excited about beginning something new. That place of not knowing where the idea would take me, but being optimistic about the outcome and what lay ahead.

The reality of what lay ahead was a long and bumpy journey fraught with obstacles and rejection. If a crystall ball had shown what would stand between me and those objectives on the post-it note, I’d never have started.

Here are just a few of the obstacles I’ve faced on my start-up journey:

  1. Getting dropped by the insurer I was an affiliate for
  2. Spending 2 years trying to find an insurer to work with
  3. A lot of rejection, knock-backs and dead-end meetings
  4. Getting admitted to hospital with burnout
  5. Navigating an industry that isn’t start-up friendly without a conventional background in insurance, co-founder or funding

There are various stages of building a business. I’m sure they look different for everyone, but for me they look like this:

  • “This is a great idea. I am so going to do this” (initial excitement. This was when I wrote the post-it note)
  • “Huh. This is kind of hard. I’m not so sure about this” (trying to find an insurer to work with)
  • “This totally sucks. I suck. What was I thinking!” (various moments—most recently last week!)

When I wrote this post-it note, I had no idea it’d take another 2.5 years to launch With Jack. Beyond launch, it’d be another 1.5 years (and counting) of manually processing quotes. That’s a lot of opportunity to get distracted, want to start over or give up entirely.

As founders, we all experience moments that test our commitment. I think it’s important to talk about them because most people only highlight the wins. As much as I enjoy celebrating my wins, I’ll admit I’m not “crushing it” 24/7.

There are some moments it all feels impossible. With those periods it’s easy to forget the ‘why’ behind what you’re building and consider abandoning ship.

Pre and post-launch there will be those moments. Prepare to have times you’ll feel lost, distracted and burnt out. I was there last week. I’ll be there again in the future.

To get through it, it helps to know your ‘why’. This keeps you focused when sign-ups aren’t growing quickly, or when a competitor is shipping more features, or when you have to write another business plan because the last 2 were rejected, or when churn is higher than normal.

You get the gist.

The Reasons I Started My Business

I’m 1.5 years into building With Jack. Does my original mission still drive me and get me out of bed in the morning?

Yes, it does. Although it’s still a work in progress (but that’s part of the fun and frustration).

It Needs To Be Human

This is one thing With Jack does well. My customers even say so.

What does With Jack do well?

With Jack achieves this through a combination of its conversational interface, and genuinely caring that customers have a good experience.

I’ll refrain from cookie-cutter customer service terminology (“We apologise for any inconvenience”) and try to be real. It’s obvious when a customer service rep is reading from a script. There’s nothing human about that.

With the customer journey, we strive to keep it personable and engaging. When I deal with customers, I try to be anything but a corporate insurer. My target audience appreciate this.

This is a crucial part of With Jack’s DNA. It’s still just as important to me 1.5 years into building my business.

It Rewards Loyal Customers

As a consumer, I regularly see my premium skyrocket only to be offered a better deal when I threaten to leave. A lot of big companies treat existing customers unfairly. Bells and whistles are reserved for attracting new customers.

I tackle this by allocating more resources to pleasing existing customers instead of chasing new ones.

As a bootstrapped start-up it’s going to cost more to acquire new customers than retain existing ones. It’s more effective to treat my existing customers well and let them market With Jack for me. It’s not rocket science.

Rewarding loyal customers isn’t just about not nonsensically raising premiums. I’ll share their achievements on Twitter, show gratitude for their support and take an interest in their work. This is another important part of With Jack’s DNA.

The Technology Doesn't Suck

Technology in the insurance industry has changed a lot since 2013. There was no ‘insurtech’ scene (gosh, I despise that term).

Now the entire industry is focused on technology. When I built my first quote system it was fully responsive—an approach that hadn’t yet been adopted by the industry. Now there are a lot of interesting ‘insurtech’ start-ups, and With Jack is lagging behind on the tech front.

That won’t always be the case. Part of last week’s stress stemmed from submitting my delegated authority application, which will open doors to improving the technology. It means building a self-service platform and gives us more scope for creativity.

From the three objectives on the post-it note, this is the one I’ve made the least progress with. That surprises and disappoints me.

Chasing The Dream 4 Years On…

Building a business is hard work and emotionally draining. Remembering my ‘why’ has helped keep me focused during those low moments.

As my stressful week has come to a close, I feel better having revisited the reasons I started With Jack. I remember why I’m doing this. I acknowledge there will be other tough periods and every founder has these moments. I prepare for another week of putting one foot in front of the other, even if it doesn’t always feel like I’m moving forward.

My goal is to build a customer-focused insurance business with design and technology at its core. Achieving this means helping more freelancers protect their business and livelihood. That’s something that drives me forward and gets me out of bed, however challenging things seem.