Growing WithJack, Ashley Baxter’s Side Hustle
Organic growth
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Today, welcome Ashley Baxter.
Hello and welcome to Zero to Grow. Please introduce yourself to our audience.
Hey! I’m Ashley and I’m building With Jack. I also like video games (currently playing Horizon Zero Dawn), photography, my dog and weightlifting. I can deadlift 95KG. That’s me in a nutshell.
What is With Jack and how did you come up with the idea?
44% of freelancers will be stung by a bad client. I’m building a platform that helps them financially and legally when that happens. In uglier terms, it’s ‘business insurance for freelancers’.
I’d been working in insurance for 11 years prior to starting With Jack. I noticed few insurers were serving freelancers, and I wanted to transfer the skills I’d learned to an audience I liked.
Design and technology weren’t being executed well in insurance. It’s getting better now, but I wanted to build an insurance company with design and technology at its core.
That’s the origin story. Worked in insurance, thought the design and technology sucked, noticed freelancers could be better protected. Here I am, 185 customers later!
What is your favourite aspect of running With Jack? What is the upside that keeps you going?
The obvious answer is when I see the service spring into action. Not every freelancer will have to use their insurance, but I’ve had a few customers in scary situations with clients. With insurance, they’ve had the financial and legal support to help them through it.
Many of my customers didn’t have insurance before using With Jack. I’ve focused on making the customer journey simple and removing barriers so it’s easier to get insured. It’s scary to think what the outcome would be if they hadn’t found With Jack.
Aside from that, I’m really enjoying validating my ideas and finding new problems to solve. In the past, I’d dive into building something without any kind of validation. This has lead to a number of failed projects.
Now I spend a good chunk of time doing customer development. This takes the form of video calls with existing customers, surveys with lost users or having coffee with freelancers. I try to learn from every conversation and use those findings to shape With Jack.
Can you share the story of how you got your very first non-friends/family user?
In the run-up to launch I did what every internet marketer tells you to do and designed a landing page with a call to action to be notified of launch.
120+ freelancers opted in. This surprised me because it’s insurance. Having 10 people pay attention would have been a success!
I sent 3 emails to the list, one of which was inviting users to beta test the quote system. This was the ideal way to open dialogue with my target audience. Not only did I get constructive feedback on the process, but several people actually wanted to buy insurance.
This is how I won Steve, my first customer that was outside of my immediate network. He still uses With Jack today! Shout out to Steve.
I found that involving people in the build process was the ideal way to get my first paid user. Being transparent about what you’re working on helps people discover what you’re building.
What channel or growth technique has, so far, worked best for you?
I’m bootstrapping on a shoestring budget, so I try to stick to free or low-cost methods.
The number one channel for how people discover With Jack is organic search. As I mentioned earlier, few insurers are focusing on freelancers. This means I can get decent positions on Google by creating content tailored to freelancers.
Even though I’m new compared to other insurers, I’m on the first page of Google for several keywords. This converts highly. If you’re targeting an audience that others are overlooking, that can be a good opportunity to rank highly.
Another channel that drives sign-ups is a tool I created. Many freelancers don’t know what insurance they need. This tool helps them build a picture of what insurance they should consider and why.
I know enough code to build it myself, so it cost nothing but my time.
As an aside, I do share a lot of what I’m learning — including what channels are working — on my blog.
Can you share one growth experiment that completely failed, and why?
I lost hundreds of pounds taking out an advert on Designer News. It’s a good idea to go where your audience is. A lot of freelance designers hang around Designer News, but I don’t think paid ads work with insurance. People don’t stumble upon it and think, “Ooh, that looks good. I’m sold”. They need to be actively looking for it.
Not only did I spend a lot on that ad, but I bought a license for a book bundle to give away to people who signed up through Designer News. Only one person signed up. I got £26.25 for that sale. They did renew a year later, so it’s now £52.50. But it’s still a significant loss after my expenses!
Another expensive failure was paying for a sponsored post on a popular design blog. I figured it’d drive a lot of traffic to With Jack. Looking at my analytics it sent 52 visitors in 8 months. That’s £450 for 52 clicks — none of which converted. Ouch.
How do you plan on growing your user base?
Bootstrapping is tough. I’m shooting weddings at the weekend and investing that money into building With Jack, but most of the money goes into design and development. I have to focus on organic growth, which may be cheap but is frustratingly slow.
My focus is simply to do more of what’s been working. This means going all in on content creation. Continuing to speak to my customers. Building lead generation tools like https://checkup.withjack.co.uk.
Whilst it’s not scalable, I’ve seen great results from public speaking. I’ll be giving my talk — Idea to Execution and Beyond — at more meet-ups and conferences this year.
None of this produces explosive results, but I’m happy chipping away and growing slowly and organically. With Jack has made as much this week as it used to earn in one month, so it is moving in the right direction.
Where do you see yourself and With Jack in 3 months (short term goal) and 5 years (long term, pie in the sky hope)?
This is an exciting start to the year. In 3 months I’d like to have launched the self-service quote system (instant quotes instead of me having to manually process everything) and dashboard for customers to manage their insurance.
The long-term, pie in the sky dream is for With Jack to have evolved into a platform that helps you freelance confidently. In 5 years I’d like to be serving 10,000 customers.
Hustling to grow a business is rarely done alone. Do you want to give a shoutout to anyone you know (personally or from a distance) who’s doing a great job?
40% of the people who get a quote with Jack become customers. That couldn’t have been achieved without Scott Riley (Scott Riley ⚓). Scott’s responsible for designing the customer journey. He continues to work with me, despite me not having the biggest budget.
I also admire the work of Justin Jackson (Justin Jackson). As a solo founder, this journey can get lonely. I love the content Justin creates. A lot of what he talks about resonates with me. I also enjoy being a part of the Mega Maker community he’s built.
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