Startup Spotlight - With Jack

March 06, 2018
Charlotte Dougall
Charlotte Dougall

Founder of Blether, helping small businesses do big things online.

The RookieOven Startup Spotlight highlights a member of the Scottish tech startup community. The aim is to, as the name suggests, put the spotlight on Scotland’s best startups from across the country. It’s an opportunity to share information about an exciting tech startup from Scotland you may not have heard of. Giving a brief overview of the company, what they do, where they are and who they are. This post the spotlight falls on RookieOven tenant With Jack.

Meet Ashley, one of our RookieOven residents, and learn more about how she’s making the world of insurance easier for freelancers to navigate.

I’m Ashley! I’m a solo founder bootstrapping With Jack from RookieOven. When I’m not working on With Jack, I’m playing video games (currently into Ghost Recon: Wildlands), walking Indie or taking photos.

Tell us a bit about what With Jack does…

44% of freelancers will be stung by a bad client. With Jack is a tool that helps them financially and legally when that happens. In other words, it’s business insurance for freelancers!

I’m looking to build With Jack into more of a platform that helps freelancers with their business. I’m currently exploring how that looks, which means lots of video calls with existing customers and idea validation.

How did With Jack get started?

I was already working in the insurance industry before I launched With Jack. Freelancers weren’t really getting the answer to insurance that they deserve. While there are providers who target freelancers, they also target 200+ other professions. What you get is a customer experience and product that’s trying to be something to everyone. That just doesn’t work.

There was nobody saying, “Hey, we’re really good at this one thing for this one group of people”. Considering freelancers can face a lot of problems with clients—and don’t really know what their options are when those problems arise—it felt like there was space for someone like With Jack.

I started small. I tested the water by signing up as an affiliate for an insurance broker. Whilst I couldn’t build my own tech and customer journey, it meant I could launch something quickly and gauge interest. That interest was 55 sign-ups, £14,000 premium written and positive feedback towards the brand. That was my first step in validating With Jack. Then I went onto get authorised (I’m an appointed representative) and partner with an insurer so I could build my own tech. I launched in September 2016.

Did you always see yourself starting your own company?

No, I thought I’d be a full-time drummer at this point in my life. I studied music at college. I had the intention of becoming a session musician, so that was the career path I tried following. Clearly that didn’t work out.

What are the biggest challenges you face being self-employed?

Every day is an emotional rollercoaster. There’s really no consistency. It’s euphoric highs and abysmal lows. There’s no safety net. If I don’t have a good week with sign-ups, there isn’t anybody else to pull the slack. It all falls on me. That’s exhilarating when things are going well, but it’s stressful when there’s a quiet period.

If you could tell your past self one thing, what would it be?

I unexpectedly ended up in insurance after chasing my music dream. I wasted a lot of time being unhappy in the beginning because music didn’t work out. I wish I could tell my past self that—despite my dreams of becoming a drummer not working out—I’d be very happy and fulfilled, so relax and enjoy the journey. And maybe eat less doughnuts. I said maybe.

What’s your favourite thing about working in RookieOven?

I reckon I’m the only RookieOven resident that wouldn’t say the pool table. After the blazing fast WIFI, my favourite thing about working here is the community. I’ve worked from home for 8+ years. That gets lonely. Working from here breaks up the monotony of having my head buried in a computer all day—even if it’s only a 10 minute conversation with another resident over lunch. I like talking about video games with Chris from Add Jam, or asking Michael for business advice. RookieOven has kept me sane for the past 3 years.

Do you have one piece of advice you’d give to people looking to start their own business?

Start with people. If I could start over again, I wouldn’t think about what I’d be selling down the line or the business I’d build. I’d pick a group of people I want to serve and spend a solid year focusing on that audience. No getting distracted with selling or developing a business—I’d channel all of my energy into helping researching and speaking to that audience. My advice to others wanting to build a business is to start with people and not the idea.

Find out more about With Jack -

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