Ashley Baxter


Ashley Baxter

Who are you, and what do you do?

I'm Ashley, founder of With Jack. I'm building a platform that makes insurance more affordable and accessible for freelancers. With Jack is laser-focused on freelancers, so the idea is that you're never asked questions that aren't relevant to the work you do and you get the exact insurance you need. Instead of filling out a traditional proposal form, you'll have a chat with Jack. I'm building this from an office in Glasgow, Scotland which is a converted shipyard.

When I'm not building With Jack, I'm playing video games (currently Horizon Zero Dawn), taking photos and sharing them on Instagram. A lot of my hobbies are screen-based, so I make sure I take plenty of walks with my dog, Indie, in the Scottish landscape.

What hardware do you use?

I'm using a 2015, 13" Retina MacBook Pro as my main machine. I'm doing a lot of traveling at the moment as I'm going through an accelerator programme, so this comes everywhere with me. In the office I have a 21" iMac, which could probably do with being upgraded. It's a little slow — especially when editing RAW files.

I'm using a Canon 5D MK IV for photos. My house was broken into this year, so I bought this camera with the insurance payout. It's a dream. It's mostly accompanied by a 50mm ƒ1.4 lens. This is a really nice set-up and what I use to take most of my photos. I've also started making videos for YouTube, so a wider lens like the 24mm ƒ1.4 is great for that.

My favourite gadget right now is my FitBit Surge. Spending a lot of time at a screen, I like to hit 10,000 steps a day and workout 4 times a week. I like tracking all of this stuff with my FitBit and getting a weekly email of my activity.

And what software?

For my insurance business, I use Pipedrive to track my sales funnel, ConvertKit to communicate with customers, and Zapier to automate a few tasks.

Customer development is really important to me. I want to know my customer. Iterate is a new app I've been using to get feedback on what I'm building.

I delegate most of the development because I'm only slightly technical, but when I do code I use Sublime Text.

Photography-wise, my software needs are pretty lightweight. I use Lightroom to manage and edit my photos.

I'm bootstrapping my business, so I try to keep my software set-up pretty lean!

What would be your dream setup?

I'd definitely upgrade my iPhone 6 to the iPhone X. I'd also like to get a quality photo printer. Lots of my photos are uploaded to Instagram and then forgotten about. It would be nice to have a quality printer at phone.

Even though I have an office which I love (and can take my dog to work!), I do also like to work from home. I'd love for my home office to have more light and space, and even an extra desk to have friends come over and collaborate. My home office looks into a car park, which isn't very inspiring. My dream set-up would have a view of a park or nature of some sort. I'd have an espresso machine in the corner, so there's always the aroma of fresh coffee.


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