Since launching With Jack I’ve stuck to semi-regular updates. Usually I write a blog post every fortnight or so, but life got in the way.

Here are some of the events that took priority over blogging:

  • My dog got sick. A cancerous tumour followed by pancreatitis. I’m really attached to my dog, so that sucked
  • Wedding season kicked off. I’m still shooting weddings so I have funds to put into With Jack
  • Traveling. I flew to South Uist for an island wedding and visited England to film a segment for Right on the Money

Now that my dog’s better and I have no more weddings until July, I have a couple of (relatively) uninterrupted weeks to get back into my routine! Let me fill you in on what’s been happening.

Improvements To The Onboarding Process

It’s funny looking back on the first few months of With Jack. The only part of the process with any polish was the quote system. Beyond that it was scrappy, not to mention I was only offering one product.

I’ve enjoyed iterating on With Jack since its soft-launch in August. First by rolling out new products based on what customers were requesting. And now by polishing the rest of the onboarding process—the risk questions.

For those that haven’t yet used With Jack, the current process looks like this:

  1. You submit your details via our quote engine
  2. Jack emails you a breakdown of your quote
  3. You answer your risk questions
  4. Jack sends you your policy documents

For launch I invested my resources into step 1, the quote system. This is With Jack’s bread and butter. For step 3 we threw together a form without too much thought. It didn’t take long to notice it was causing confusion.

These were some of the questions people would ask at the risk questions stage:

“Is this the final step? Am I committed to buying insurance? How do I pay?”

I worked with Naomi Atkinson on redesigning the risk questions. We specifically addressed the above confusions and rolled out the updated form last month.

Here’s the before and after:

A before and after of the risk questions form

Aesthetically it’s a lot better, fitting Jack’s whole ‘design at the core’ ethos. More importantly—since implementing the new design—I haven’t heard any of the above questions.

Mission: Accomplished.

Inching Closer To 100 Customers

The next blog post I publish will be celebrating hitting the 100 customer mark. (I hope.)

Right now I have 95 customers. This means I’m a 1.5 weeks away from the big 100! That is unless I have a surprisingly good or horribly slow fortnight.

With Jack is about much more than the numbers, though. I could have 10 customers and it would still have the same mission—getting creative businesses the protection they need, doing so with as little hassle as possible and in a format that’s simple.

With that said, I can’t deny that getting to 100 customers as a bootstrapped, solo founder feels great.

This nicely ties into my next update…

I've Applied To An Accelerator

I did something I never thought I would. I applied to Ignite, an accelerator.

Let me back up a bit.

A few months ago I attended a startup dinner in Edinburgh where Tristan (Ignite’s CEO) was a guest. Tristan and I have met before, but this was the first time I asked if Ignite would be a good fit for me.

As much as I want to champion bootstrapping and love the idea of being a solo founder, I’m struggling with building With Jack on my own. It’s growing very slowly. I feel I’d benefit from a network, mentorship and being around other startups.

I’m not comfortable with accelerators (mostly because I like hiding behind my computer). But if something scares me, it’s usually a good indicator I should try it.

I had my video interview last week. I’ve since been invited to the last stage of the application process in Newcastle. This is what determines who is accepted into the final programme.

Fingers, toes and eyeballs crossed.