This is the talk I gave at Hybrid Conf in Berlin, August 2016. If it reads a bit awkwardly that’s because it wasn’t optimised as a written essay—it was optimised as a talk.
I’m talking about going from idea to launch in 11 years. 11 years. That isn’t a typo. I want to share 3 reasons it took 11 years and the lessons learned from that.
My alternative talk title was: How A Solo Founder Attempted To Take On The Financial Services Sector And Failed Over And Over And Over Again. But that was a bit wordy.
First, a brief backstory. The most common question I get asked is, “Why insurance?”.
Nobody grows up wanting to work in insurance and I was no different. As is the case with life, though, it can throw unpredictable events at you and change the trajectory of your life overnight.
That photo you see? That’s my Dad. This photo is of him sitting in the hallway of our house, which doubled as my Dad’s home office, selling insurance to landlords. Not long after this photo was taken my Dad passed away and I inherited his insurance business. I was 18.
Prior to this, the biggest decision I had to make was whether to wear my checkered Vans or my leopard print Converse.
I didn’t really like my job in the beginning and for many years I plodded along. I’m sure you’re all thinking the same thing I did all those years ago…
Insurance is boring, stuffy and corporate. Insurance is where creativity goes to die!
All insurers look similar. All insurers sound similar, yet 72% of people don’t trust their insurance provider.
Something needs to change and I want to do my bit to fix that.
At some point along the way my mission became clear: I want to build an insurance company with design and technology at its core.
Oh, and really good customer service.
That’s why Jack was born, business insurance for creative freelancers.
But why did it take 11 years?
Reason #1: I Cut Corners
As many people will know from first hand experience, starting a business is far from easy. Especially in the financial services sector what with all of the regulation that’s involved. It’s a heavily regulated industry and can be difficult to break into.
Insurance is vastly different to creative industries. It’s different to the web industry where there’s a sense of collaboration. Designers share processes, developers share what tools they’re using.
Insurance isn’t like that. It’s not very transparent. It’s difficult to find real, tangible advice on how to take your idea and turn it into a business in the insurance sector.
I entered the industry from an unconventional background, with no formal work experience, qualifications or contacts.
It makes what’s already an industry with a high barrier to entry even more challenging to break into.
What I’m trying to say is, I wanted to create this insurance company but I had no idea how to.
So, I cut corners and took the easiest option available to me.
I first started Jack by building it on top of someone else’s insurance company.
I would sell their product (the insurance policy) using their platform (the quote system) and all of their infrastructure. Every aspect of Jack was built on top of a third-party—there wasn’t any part of the process I managed.
But this was the quickest and simplest way to getting started!
Here’s the problem with cutting corners. You’ll launch quicker because someone else has already done the hard work for you, but it’s at the cost of you giving away control.
And when your livelihood is banking on a third party, you’re putting yourself in a risky position.
Now don’t get me wrong, I’m an advocate of cutting corners in some instances. Perhaps to test an idea, to get something out there quickly and gauge whether people will pay for it before investing your resources into it.
But to do what I wanted to do—this grand goal of building an insurance company with design and technology at the core (oh, and really good customer service)—this approach wasn’t going to cut it.
I had zero control over the design and the technology. I had no influence over the customer journey.
What I did have was a fancy website that did a great job communicating the vision I had for insurance…
…but fell short where it actually mattered—delivering on that vision.
I definitely did some brand damage to Jack by going down that route. People came to the website with certain expectations, but those expectations weren’t being met.
People’s expectations not being met resulted in poor sales. With that first version of Jack, it took me 3 weeks to make my first sale. But with the current version—where I’ve put in the time, effort and expense to build my own platform—I made my first sale 3 weeks before I launched.
But that wasn’t even the biggest problem I had. The company I’d built my business on top of ended their partnership program, which they were within their rights to do so. But as I was building my business on top of that platform… suddenly I had no business and there was nothing I could do about it.
Remember, the easy option is easy for a reason—it won’t get you the results you really want.
The harder route may involve more work, time, effort and expense, but at least you have control over the outcome.
I’d have gotten to where I want to be a lot quicker had I put in the work in the first place to build my own platform, instead of cutting corners.
Cutting corners may be the quickest way to getting started, but it’s also the quickest way to go out of business.
Reason #2: I Lacked Focus
One of the biggest challenges I’ve faced—and perhaps the biggest reason it’s taken me this long to launch—is with staying focused.
As creatives we have a lot of ideas and interests. They pull us in all kinds of different directions (if we let them, which I did).
I used to think that having multiple side projects was a measure of productivity. A badge of how hard I was working.
I was juggling wedding photography.
Two insurance companies.
I had a gaming blog.
A weekly podcast…
…and fortnightly slot on TV.
I’d organise photography meet-ups.
I launched a photo course.
And I built a Ruby on Rails app.
What was I thinking?
Not only did I burn out big time, but I hit a plateau. I couldn’t attract higher-end wedding photography clients and charge more because I wasn’t doing it full-time. And I wasn’t anywhere closer to reaching this goal with insurance because I was also focusing on photography.
Being honest with myself, I always knew I had a problem with focus. It took a long time to admit it. I was always distracted by something new. Shiny object syndrome. I know I’m not alone with this, I see it with other people too.
There came a point in my life, though, I had to get real and admit I can’t achieve my goal with 50% focus. Nothing really great ever happens with 50% focus! This needs 100%.
Going forward I started asking myself a simple yet incredibly effective question:
“Will this take you closer to your goal?”.
If the answer is “No”, I drop it. I don’t do it.
It’s hard and I still mess up occasionally, but I’m getting better at it.
It’s no coincidence that since giving my goal 100% focus, that’s when things started to progress.
Let me show you a timeline of events.
Thinking this was the turning point in my career, I gave a talk about it at Industry Conf.
In June of 2015 I got admitted to hospital. This was a big turning point for me. I’m in my 20’s. I don’t smoke, I go to the gym, but I was burnt out! I wasn’t sure I wanted to be in insurance anymore.
In February of 2016 I went to bed, couldn’t sleep and got up at 3AM. I sent a desperate email to James from Worry+Peace. I’d read his thoughts on insurance and technology and agreed with a lot of his writing. I asked for help.
It’s pretty obvious at what point in my life I decided to focus.
When I got out of hospital I took a month off work to figure out what I wanted to do. Evidently, I chose insurance and spent the next few months phasing out all of the other distractions in my life. Turning away clients, culling side projects. I even deleted Candy Crush off my phone!
But it wasn’t until the start of 2016 I went full throttle. Sitting my exams, making connections, going down the proper route and through the Financial Conduct Authority (FCA).
I’m sure it won’t take you 11 years to reach your goal, but I think we could all do with a reminder that the sooner you drop the unnecessary distractions in life, the quicker you’ll gain steam.
The best thing you can do for your career is learn to say no.
Reason #3: The Final 20% Is The Hardest
When I took a month off work I read a book that completely changed my life. I’d experienced a few knock backs. A lot of insurers seemed unwilling to work with me and I’d had many leads that didn’t pan out. I didn’t seem to be any closer to my goal. I was near to giving up.
Then I read ‘The Dip’ by Seth Godin.
Has anyone ever noticed that the final 20% of a project is the hardest to complete? It’s some weird psychological effect that makes that final 20%—whether it’s starting a business, building a web site or working on a side project—the biggest hurdle.
The Dip talks about that part where excitement fades and “…it gets harder and less fun, until it hits a low point - really hard, really not fun”. That’s The Dip.
At that point most people quit.
If you keep going through that really hard, really not fun part you inevitably have a much higher chance of success. The reward is potentially bigger.
The Dip is when successful people don’t quit.
I completely identified as being in The Dip when I read it. It was such a serendipitous thing; to be in that place in my life and come across this book. That place where I knew I wanted to build an insurance company, but I’d had a challenging time getting anywhere with it and there still wasn’t any light at the end of a tunnel.
The question that changed everything was:
Did I want to quit, only to pursue something new and shiny until that, too, became difficult, only to quit that and repeat this pattern for the rest of my life?
No. That doesn’t sound like progress!
I had the option to quit or commit. I chose to commit to pushing through the final 20% and I quit the right things. The side projects, the photo walks, the software I’d built that nobody was using.
It’s useful to use The Dip to measure how serious you are about something.
Acknowledge that whatever you start there is going to be that final 20% that seems insurmountable. If you can’t make it through The Dip, don’t start in the first place.
But as Seth Godin says, if it’s worth doing there’s probably a dip.
There are many other reasons that contributed to it taking me 11 years to launch my business, but we’d be here all day if I detailed every one of them.
When these three factors clicked into place I was able to accomplish my goal.
- I stopped cutting corners. I didn’t build on top of another company’s platform. I put in the, time, work and expense to create my own
- I focused. I phased out distractions. I gave the middle finger to shiny object syndrome!
- I embraced The Dip. I recognised that this is the hard part, but it doesn’t matter what I do in life, there’s always going to be The Dip. I want this badly enough to get through it
The reason that I spoke about this is because I think we see a lot of what works.
We hear about what goes into making a company a success, but what about the bit before all of that?
The part where you’re trying to get something off the ground? The years of mistakes, learning, rejection, frustration, and the almost giving up, questioning whether you’re even doing the right thing and on the right path.
That part sucks. There is nothing fun about that part! Yet that part is completely necessary to get to the next point. Hang in there and continue showing up every day—you could be one desperate, 3AM email away from making your goal a reality.