A couple of months ago I soft-launched a piece of software I've been chipping away at for some time. Okay, that's an understatement. A couple of months ago I launched my automated quote and bind system that has been 6.4 years in the making.

Let's rewind a bit. By "a bit" I mean a couple of decades.

The whole reason I work in insurance is because I inherited my dad’s business. He died when I was 18 after his health deteriorated due to heart problems.

When it became clear he wasn't going to get better, he asked me to look after the family. I tried to do that by keeping the family insurance business going.

There were a few problems.

1. I didn't have much business experience and I didn’t have the right skillset. Weeks prior to my dad’s death I had been studying music with the dream of building a career around that. I did have a background in creating websites for bands that I played in, but I was learning everything else on the job while grieving for a parent. It was a dark time
2. The insurance industry was completely foreign to me. I'd never bought insurance as a teenager, and the market that my dad sold insurance to was one that I was never able to get excited about (property insurance, mostly buy-to-let)
3. At the same time, the industry was going through a seismic shift that rendered my dad’s business model obsolete. If you want more context around that story I spoke about it on Startups for the rest of us with Rob Walling

I was never able to grow and make a success of my dad’s business.

It took a lot of work to reach a place where I no longer beat myself up about that. Now I try to focus on the positives I can take from that chapter of my life.

• I modernised my dad’s business and had improved its online presence
• I built a SaaS app
• I even developed and demoed a quote system to an insurer in London that—had they taken a gamble on it—would have been the first responsive quote system in the UK

Mostly my feelings are that of privilege because my dad's business gave me a platform to learn new skills and figure out what I was interested in. It turns out that was design and technology (these days tech overwhelms me). I was able to channel a lot of the failures from my dad’s business into building a successful one in With Jack.

I have leaned into the insurance industry. I’ve taken steps my dad never did. I became a broker. I got my license. Then I set my sights on becoming a Lloyd's coverholder and getting a delegated authority, a process that would take over 6 years but would allow me to build my own software and take ownership of the customer journey.

I have done these things which are very hard and very not fun and very expensive and very time consuming because I've learned the importance of owning the customer and the technology.

And when I say I've learned the importance of owning the customer and the technology, I have learned that lesson the hard way.

Many years after my dad died, I was walking my dog on a Friday afternoon when my phone rang. It was the insurer that had bought the company my dad had worked with for almost 20 years. They were terminating our contract with 30 days' notice.

Because my dad had never taken those very hard and very not fun and very expensive and very time consuming steps, every customer we had now belonged to them. Because we depended on their technology to power our business it was a phone call to brutally say "your business disappears in 30 days".

That business was my dad’s legacy. It had outlived him by almost two decades. Somebody else who didn’t live through that and who didn’t know what it meant to my family got to decide how it ended. That sucked.

That wasn't the first time something like this had happened to me.

Back when I started playing around with the idea that would become With Jack, I signed up as an affiliate for an online broker. This was a low cost way to get started with dipping my toe into insurance without the regulatory overhead.

I built a landing page, put some money into branding and marketing and funnelled customers to a third-party broker. It ended with the same outcome. I received the news that it wasn’t working for them and they gave me 30 days' notice.

It didn’t sting as much as losing my dad's business. That was an experiment and I was testing things. It was low risk and low reward, but both of these experiences lead me to the same realisation.

I understood that if I was going to do this… if I was going to go all in on building With Jack I’d need to do it properly. No shortcuts because cutting corners leads to the same outcome. I would commit to doing everything the very hard and very not fun and very expensive and very time consuming way because I’ve experienced first-hand the vulnerability of choosing the easy option.

The journey that I’ve been sharing in drips and drabs over the years about building the automated quote system and getting my delegated authority is part of that. I've had many sleepless nights because of this, despite simplifying the leap in my head as just building a giant calculator.

But the truth is I’m now many years into this project. I’ve invested tens of thousands of pounds into this project. And every few days I’ve questioned whether I’m doing the right thing.

The business I'd already built was comfortable. Cashflow was growing, I was adding new customers. Was it worth risking all of that just to build my own technology?

The stories above validated my decision to do things the hard way. Whatever happens, I’ve now got the infrastructure in place that means my customers are my customers.

After 6.4 years, three different teams and more money invested than I'm quite ready to calculate, I received an email one Tuesday afternoon in December.

The industry has sucked a lot of creativity out of me. Then I remind myself that I had to do the very hard and very not fun and very expensive and very time consuming part to put myself in the driving seat for however long I want to continue in the insurance game and take back creative control. That's when I remember it will be worth it. It has to be worth it.

Becoming a Lloyds coverholder happened exactly 1 month before my mum passed away. It would take another year to actually build the technology and get the green light to launch, but I am so happy I have these words from my mum.

You made it.

I am proud of you.

The day my developers pushed the new quote and bind system live (or the giant calculator as I like to downplay it) I didn't feel much of anything other than fear.

Fear that existing customers would resist the change. Fear that the new system wouldn't be intuitive. Fear that it doesn't convert well. But realistically I can only find out if any of those things are true by launching it. And even if they are true, I can troubleshoot and fix them. That's what I've been doing for 9 years, so why am I afraid?

And then there is the other possibility.

What if it doesn't suck? What if this takes my business to the next level, enabling me to help more freelancers while having a better work / life balance? What if this ends up being a life changing achievement? What if this is the best professional thing that ever happens to me? Why can't I let myself dream a bit?

In an ideal world this launch enables me to:

• have a better work / life balance since the system handles a lot of the admin I've been doing
• give customers quicker access to products and services that meet their needs
• make the business more attractive to acquire (when the time comes)

Whatever happens I need to stop overcomplicating things and embrace the challenge. After all, it's just a giant calculator.