Early-stage Makers (Interview #1) — Building an insurance company for freelancers

WithJack provides bespoke insurance for freelance creatives. Launched in September 2016 (with a soft-launch in August), it has surpassed £100,000 in premium written. Here’s an interview with the founder, Ashley Baxter


Adith Victor: Tell us a little bit about your background. What did you do before starting WithJack?

Ashley Baxter: A long time ago I identified as a musician. I was studying drumming at college and my plan was to work in the music industry. At 18 I unexpectedly inherited the family insurance business, and that’s what got me started on this path.

Why did you build WithJack?

I noticed several problems in the insurance industry.

1. The vast majority of people don’t trust their insurance provider

2. Few insurers are investing in their technology

3. People don't enjoy the customer journey when shopping for insurance

Those problems excited me and I wondered if I could create a business people could trust, with great design and technology at its core. That lead to building With Jack.

How did you go about building the platform?

I have some technical knowledge. I know enough HTML, CSS and Ruby on Rails to build quick prototypes and test ideas. However, I was serious about With Jack from day one, so I worked with a team of developers and designers like Simple as Milk and Scott Riley.

Do you work on the idea full-time?

As of this year, yes. Prior to this year I was splitting my time between other work.

How did you validate the idea?

Insurance is a regulated industry, so it can be difficult validating ideas. There's a lot of red tape and capital required to get started. The quickest route to market was to sign up as an affiliate for an insurer. This meant I could launch quickly and gauge feedback, but it came with lots of downsides. I had little control over the design and technology, and I couldn't build a relationship with customers because they technically weren't mine. I was able to get 55 paying customers and a lot of positive feedback. That was enough for me to want to keep iterating on it.

How did you market the idea and find initial users?

Networking, referrals, Twitter, leads from my affiliate days (see answer above) and organic search. When I launched there were few insurers targeting freelance designers and developers, so I was able to get good results on Google quickly. I had also been active on Twitter for a decade, so had built a small network of freelancers on there.

How did you convince people to use WithJack after you got your first set of users?

It's grown quite organically. Initially it was friends using With Jack, then friends started referring their friends. While this was happening I was getting more leads from other marketing channels, like organic search. I was able to grow to 100 customers this way. I've relied heavily on referrals, so thank you to everyone who has spread the word! You can read about my journey to 250 customers on my blog.

You've grown at a steady pace. What keeps you motivated?

To stay motivated I think you have to serve an audience you like (for me that's freelancers) and work on a problem that interests you (improving the insurance industry). If I was in this just to make money I'd have given up long ago. I've seen first-hand the scary situations freelancers face and how insurance can help them. I recognise and believe in the value of insurance and now I'm on a mission to get every freelancer insured. That's enough to keep me motivated!

Would you like to share that moment when you felt WithJack is the need of the hour and that you should put in more effort to make it better?

It would be the first time a claim was settled. It doesn't matter how nice With Jack's customer journey is—what matters is the service that's provided when a customer makes a claim. That’s why they’ve bought insurance. The first claim we had was for a developer who was having trouble with a client. The developer’s client was threatening legal action and refusing to pay him. The insurer stepped in, provided legal experts to negotiate with the client and paid the developer £9000 for the work they’d completed under the mitigations costs clause. There's still room for improvement with the whole process, but the outcome of that situation validated why I’m building With Jack.

You still manually process the quotes (though you planned to automate the process within few months after starting out). Is this something you enjoy doing or is it the greater value that you deliver through WithJack that keeps you going?

It's actually worked out well because it's meant having hundreds of customer conversations. I've been able to listen to the language freelancers use when talking about insurance and build stronger relationships with them. I spend about 3 minutes processing a quote, so all in I've spent 33 hours sitting at a computer and sending freelancers quotes! We are working towards automation, because the ultimate goal is to get as many freelancers insured—and understanding their insurance—as possible.

Would you like to share any memorable experience(s) you've had in your entrepreneurial journey?

For me it's important to acknowledge the experiences most people don't talk about—the difficult parts. Sure, it's fun to share the milestones of hitting 300 customers or selling £100,000+ of insurance, but to get to this point I had to spend 2 years looking for an insurer to partner with. 2 years of rejection and dead end meetings. None of that was fun and I came very close to giving up. I’m glad I didn’t.

What are your favorite blogs, books, podcasts, quote(s)?

I love podcasts! Masters of Scale, How I Built This and Startups For The Rest Of Us are ones I never miss. I've also recently enjoyed reading Hatching Twitter, Creativity Inc and Shoe Dog.

What apps do you use regularly?

When I'm not building With Jack I'm a keen photographer (wedding photography funded the development costs of With Jack), so Instagram is my favourite app. I also couldn't live without Pipedrive for tracking my sales funnel. I’ve also been enjoying Sip for daily tech news and stories.

Who are you favorite entrepreneurs and why?

I like Justin Jackson for his energy, content and transparency. I'm enjoying following his journey of building Transistor on his podcast, Build Your SaaS. He doesn’t just share the golden moments and I think that’s important. Building a business is really hard!

What's next for WithJack?

Automating as much of the customer journey as possible (we’re soon rolling out instant quotes), without losing the personal touch. I’ll also be building in some value added services so freelancers are getting the complete spectrum of protection they deserve.

Any advice you'd like to share with entrepreneurs who're just starting out?

Don’t buy into the get rich quick stories that flood the internet. Everyone else makes this stuff look so easy. "Idea To 10K MRR In 2 Months”, "How We Got 300,000 Users In 24 Hours"… For the vast majority of us launches don’t look like that. There will be a lot of days you question why you’re doing this. That’s normal, so make sure you have a compelling reason for being on this journey. Also, a good support network helps!


Follow Ashley on Twitter or read her blog posts for more updates. Check out WithJack

This interview is published by Early-stage News — A platform to discover articles and interviews highlighting early-stage startups and side-projects.