If it was easy everybody would start a business. Last month I launched With Jack, so what issues have I faced with the first month in business?

That Post-Launch Traffic Slump

Launch day (or week) brings a surge of traffic.

You’ve shipped something new, people are eager to check it out. They’ll tweet about your product, share it on Facebook or mention you on their blog.

You might even get ‘Hunted’ or featured on Designer News. The really smart people will have built a list of loyal followers to launch to.

If you’ve done things right in the build-up, launch day will do the work for you when it comes to driving traffic.

Jack experienced a surge of traffic during launch week, which in turn brought leads. Lots of ‘em. Some of those leads became my first customers.

But what happens when launch traffic dries up? You need to find a way to keep a steady stream of traffic (and leads) coming in. How do you do that once the initial buzz has died down? That’s what I’m trying to figure out.

Understanding My Audience’s Preferences

My goal is to make insurance simpler. I may be biased, but I think With Jack’s quote system ticks that box. It asks the questions it needs to get you a quote—nothing more.

All insurers have different question sets for cover. Some demand endless forms to be filled in, while others require a few key details. We work with an insurer who falls into the latter category, but it comes at a cost (quite literally). Higher premiums.

Recently I added another insurer to my roster. While their premiums are cheaper, they request a lot more information upfront—some of which doesn’t feel relevant for freelancing. It doesn’t jive with the simple, freelance friendly process we’re creating at Jack.

But maybe I’ve got this all wrong. Perhaps freelancers are willing to spend an extra 15 minutes when buying insurance to save money.

Should I compromise on With Jack’s ethos to give my customers access to cheaper premiums, or do they value convenience and simplicity more?

This is a difficult question.

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 manually issue quotes and cover. I personally follow up on last week’s quotes, or remind customers to fill in their risk questions. Y’know, the general admin of running an insurance company.

Some days are quiet in terms of leads coming in, but with busy periods these processes can eat into my day. It’s not uncommon to get to the afternoon and I haven’t managed to do the work that’ll attract more business.

I haven’t sent that newsletter, written that blog post, published those adverts, updated social media etc.

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

A lot of insurers have been around for a long time. They’re decades old. They’ve had years to hone their processes and improve their product.

With Jack is one month old, yet I’m competing against insurers who have decades of experience.

This can work in my favour—the industry needs fresh thinking and ideas. But at the moment, with starting a company from scratch, With Jack is a little lean compared to its competitors in terms of features, tools and benefits.

How do I convince people to get onboard with a new business?

These Are Good Problems To Have

• Keeping traffic flowing post-launch
• Finding out what’s important to my customers
• Balancing bringing in new business with binding new business
• Getting people onboard with a new company

It’s taken me a long time to launch With Jack, so I’m happy to be having these ‘problems’. It’s fun figuring this stuff out.

I’ve been in business long enough to know that it never does get easy. Challenge accepted.