With Jack Product Information and Latest Updates (2025)

This is the 2nd launch from With Jack. View more

With Jack

Business insurance on a first name basis

Almost 50% of freelancers will be stung by a bad client. With Jack provides an insurance policy that protects them financially and legally if that happens, freeing them up to focus on the important stuff.

Launch tags:

Web App•Tech

Launch Team

Ashley Baxter

With Jack

Maker

Hi, everyone. I'm the 'maker' behind Jack. Since Jack was last hunted I've become an Appointed Representative through the Financial Conduct Authority, teamed up with a couple of UK insurers and have built a conversational quote system for freelancers. Soon enough we'll be developing this into a system that can give instant quotes and cover online, but it's baby steps. Working on an insurance start-up is challenging :-) Thanks for checking out Jack!

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8yr ago

Justin Jackson

Transistor

@iamashley the design of your website is refreshing! Love how personal it feels. Well done! 💯

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8yr ago

Geoffrey Wiseman

@iamashley Do you only cover the UK? What countries do you offer this insurance in?

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8yr ago

Ashley Baxter

With Jack

Maker

@geoffreywiseman We can insure businesses in the UK and Ireland. Would love to expand… one day.

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8yr ago

Geoffrey Wiseman

@iamashley Ah well. If you ever expand to Canada, look me up. ;)

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8yr ago

Simon Burns

Keza

@iamashley Congrats on the launch! Super exciting, lots to fix in business insurance!

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8yr ago

eelco

Sjabloon

Big ❤️ for the visual design!

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8yr ago

Ashley Baxter

With Jack

Maker

@eelcojellema Thanks! I hired http://simpleasmilk.com/ for that.

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8yr ago

Greg Gilbert

The Prayer Page

Congrats on the launch @iamashley! Super happy to see you featured on PH. You've been working for a while on this project, defeating one by one the obstacles that come with creating this kind of businesses. Congratulation! Can you tell us about the specific problem that you solve with Jack? Also, you have a great story building this. Mind sharing it with us? The genesis and the obstacle you ran into?

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8yr ago

Ashley Baxter

With Jack

Maker

@gregoiregilbert Thanks, Greg! I've been in the industry for over a decade and noticed there are no insurers serving freelancers. Freelancers are overlooked by insurers because it's still considered a small market, even though it's growing. Because of this, freelancers don't have much information about why they need business insurance, therefore they overlook it. This upsets me because they are just as vulnerable as more traditional businesses. How many freelancers do you know that have run into problems with unpaid invoices and crappy clients? A lot. What I want to do with Jack is tailor the experience specifically to freelancers. Provide content that educates them as to why they need business insurance, offer a customer journey that's designed for them and makes it easy to get a quote, provide a policy that will cover them for what they need, then top it off with customer benefits that are relevant to freelancers. My story spans 11 years when I inherited my Dad's property insurance business at the age of 18. I taught myself a bit of code and really got into design. It was through doing that I realised how much the technology and design (amongst other things) in the insurance space sucks. It's taken me this long to launch Jack because I come from an unconventional background. I inherited a business instead of working my way up in a traditional insurance firm. I don't have industry qualifications or even a University degree. Because of that, I may seem a bit of an edge case in the insurance industry and many insurers weren't keen to take a chance on working with me. I'm glad I persevered.

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8yr ago

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