Away from Keyboard – Episode #3

Ashley Baxter is excited about… insurance?


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Thirteen years ago, Ashley Baxter inherited the family insurance business when her Dad passed away. Even though she’s a talented photographer, and built a successful photography business, the insurance industry kept calling her name. Ashley talks about what excites her about insurance, the challenges of running a business, and how burnout forced her to focus.



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[01:46] Thirteen years ago Ashley Baxter’s father passed away, and she herself says on her about page that some parents leave their kids jewelry, maybe a collection of some sort, but Ashley inherited an insurance business… Although Ashley isn’t still running her dad’s insurance company today, even after establishing a successful wedding photography business, there was something about the insurance industry that called her name.

Now, to most people, insurance isn’t something you get excited about… But Ashley is not most people.

I felt like they were a lot of problems to solve, problems that really excited me. For example, two out of three customers are unhappy with their journey through buying insurance… So that excites me, like “Okay, in that case how can we make it more – I don’t think shopping for insurance is ever gonna be enjoyable, but how can we make it a bit more pleasant?”

And there were other problems too, like most people don’t trust their insurance provider, so how can I build a company that people do trust and put their faith in and feel good about using? So those were the problems that I felt excited about, that led to me starting With Jack, and then I’d say that now that I’ve been doing With Jack for a couple of years, there’s another thing that excites me about insurance, and that’s that so many people just don’t understand the value of it, so I’m selling business insurance to freelancers, and there are so many freelancers running their business without insurance, because they don’t understand how it would actually add value to their business… Which isn’t their problem, it’s our problem as the insurance companies - we should be doing a better job of educating them.

That’s something that excites me now - having this mission… There are two million freelancers in the U.K., and it’s my mission to get them all insured.

I would love to hear that explanation, because I definitely feel like one of those people. What is the value insurance brings to me? I mean, I’ve heard you explain that, kind of, in some of your YouTube videos as well, but I’d love to hear your shorter explanation as to why is this so valuable for freelancers?

[03:56] Yeah. Well, I mean, it’s like any insurance, so you have a big group of people - in this case I have 300 customers, and not all of them are gonna use their insurance… But for the few that do, we’ve had 8 or 9 claims now, and as a result of these freelancers being insured, we have kept them in business. There have been situations which we’ve seen time and time again where you can perhaps work with a client who’s a bit of a bully and tries to use scare tactics to get more out of you, or refuses to pay invoices… You know, we’ve seen just projects go wrong, being delivered late… Just various situations that lead to unhappy clients, who try to make a claim against you or threaten legal action.

And if that freelancer doesn’t have insurance – I mean, our biggest claim was for 60,000 Pounds, and that would have put that person out of business; they could have potentially lost their home, they had a family… You know, you’re essentially transferring the risk to somebody who can pay that amount, if that makes sense. That’s what it’s all about.

It’s not the sexiest subject, it’s not the best business expense, but if you do find yourself in that situation, you will be glad that you were paying 14 Pounds a month or 20 Pounds a month, whatever it is, because the insurer gives you access to lawyers, they handle everything for you… They don’t only take the financial burden, but the emotional burden too, and I just think that that’s absolutely priceless. But then again, I am biased, I have seen these situations… Luckily, most freelancers won’t face those problems, but it’s there just in case they do.

And currently, you are only in the U.K. Do you have plans to change that?

Well, I get asked that a lot, which is great; I get a lot of European visitors on the website and they always ask me “Are you gonna come to Germany?”, or here and there, and the problem is that insurance is a regulated industry, and the reason that it took me so long to launch With Jack is because I really struggled to wrap my head around all of the regulations side of things. There’s so much red tape that it’s just difficult to get started. It was so hard to get started in the U.K. that I can’t even imagine then having to go through that whole procedure to sort of branch out into Europe and the U.S. especially.

So right now I just wanna focus on this market, because I’m up and running here, and I have 300 customers, and I’m seeing there’s two million freelancers… So obviously, I’ve barely tapped into the market. So yeah, it would be great one day, because I do think that people seem to respond really favorably to With Jack’s brand, but there are no immediate plans, unfortunately.

I kind of wanna go back to the beginning of our conversation where I asked you what it is about insurance that gets you excited, because you are a very talented photographer; I absolutely love your vlogs. How do you feel that the insurance industry scratches your creative itch?

You know, it’s weird, because I actually feel that it scratches my creative itch more than photography does right now.

Yeah. I know I never thought I’d say that. I feel like there are bigger problems to solve with insurance. With photography, I’d photograph weddings, and it’s really meaningful to be able to give somebody a gallery of their most special day, and give them lots of great memories, but I feel like there’s much bigger impact that can be made by building business in the insurance space… And even though insurance is a really dry subject, I think that I’ve made it work really well for myself as a creative person. I’m doing my YouTube videos and really enjoying shooting them and editing them and writing out the content, or you know, just creating the content for the blog or for Instagram.

I’m getting to go and do public speaking and talk about this stuff in front of hundreds of people… I feel like I’ve taken this business and made it work for my creative personality, if that makes sense…

Yeah, that makes a lot of sense. And that’s true, you have been doing, like we’ve mentioned before, a lot of YouTube videos and vlogs, but also some speaking as well, which I think you have enjoyed a lot, right?

[08:13] Oh no, I hate public speaking. Do you like it?

Do I like public speaking? I do enjoy it, yes. I get nervous just like anybody else, but I enjoy public speaking, I enjoy being in front of a lot of people and sharing something that I’ve learned… So yeah, I enjoy it.

I don’t know, I keep telling myself that the more I do it, the more I might end up enjoying it, but that just hasn’t happened yet. So I think this is where I’ve been going wrong, because I was writing a new talk for every conference or meetup they would ask me to speak, whereas for the past three, maybe even four conferences/meetups I’ve done, I’ve written one talk and then just iterated on it, and I’ve been getting really good feedback about that.

So that’s my plan going forward - to have this one talk that I’ll be doing for a while, and then I hope that the more confident I become with it, the more I enjoy public speaking. But it’s really rewarding when you get the tweets and people feel inspired by your talk, or whatever, but when I’m there on stage, I don’t enjoy the act of public speaking. It’s terrifying, isn’t it?

Yeah… So if you don’t really like it and you get so nervous, why is it that you push through and do it?

Well, I think it’s really important to do things that scare you. You grow as a human being, as a person if you do things that push you out of your comfort zone. I don’t think I have a profound message to share, but I do really enjoy being really honest about this part of building a business, because I’m not successful yet, I’ve not made it yet; it’s still a work in progress, and I think it’s really important for people to share this part of the journey… Because all too often we hear from people who have companies that are turning over 50k monthly recurring revenue, and they’ve figured all of this stuff out, and it’s not very relatable… Whereas I’m kind of standing there on stage, saying “I don’t have any funding, I’m very much in the thick of it, I’m still figuring everything out”, and people can really relate to that, so that’s why I enjoy doing it.

I like that, because I agree with you. A lot of the times - and to a certain degree that’s what I’m trying to do with this podcast, is share the stories that aren’t so glamorous sometimes, because I feel like we all struggle, we all have difficulties, and those are the things that I think more people can relate to, and not so much – because we live in an Instagram world, where you put your best face forward all the time.

Yeah, absolutely. I think that if you listen to the stories about the successes, then if you are somebody who’s thinking of starting a business or have just started a business, you’re doing so under false pretense. For me, I’ve found that there’s so much work and so much time of not making much money, and there’s really long periods of putting in so much effort, and blood, sweat and tears and money into something and not seeing a return on investment. There’s years of that part, but people don’t really talk about that, which is what worries me, because we’ve got great websites, like Indie Hackers, which I love… All of these websites where it’s a bit too easy to read those glamorous stories of success and get a bit too caught up in that… So that’s why I think it’s important to get the story out about “Well, here’s how it looks for me, and it isn’t that glamorous.”

Running a small business has good days and bad days, but sometimes the bad days out-number the good days. According to Ashley, the key to making it through those bad days starts with the right motivation.

I’ll be honest with you - the past year has been really tough. There have been a lot of obstacles in my way, and if I was doing this just for the money, I would have quit by now, I would have walked away by now, because it just wouldn’t be worth it. So I think that actually being invested in something bigger and more meaningful than just doing it for the money really keeps me going. I really believe in With Jack, I really believe in getting freelancers insured, so that keeps me going…

But also just having that – I mean, this is a bit of a cliché, but having that support network… I don’t really have friends who run businesses, so that can be tricky, but I’ve made a lot of online friends who are in the same space, they’re building businesses… And even the people who are helping me build With Jack, the freelancers I’m working with, like Scott Riley and Vic Bell… I’ll pop into her Slack chat and I’ll just have a big morning rant at them and they’ve been really great to just listen and give me that pep talk that I need, because I’m a solo founder, so I have to shoulder so much of the emotional side of things myself.

So I think having that support network has been key, and then also just really believing in the mission at hand and not just doing something for the money - that is what keeps me going.

I think that’s so interesting, because we obviously understand that money is an important part of all of this; money is what allows us to pay our bills, pay our rent, survive… But at the end of the day, when it comes to creating a business, sometimes it has to be a little more than that, because the difficulties of building a business, the moments of blood, sweat and tears and often times, like you yourself mentioned earlier, the amount of work and time that it requires - just doing it for the money sometimes is just not enough.

No. To be completely transparent with you right now, I could 100% earn more money if I just went and got a job working somewhere… [laughter] That is the truth. So yeah, it’s definitely important to have more motivations than just financial, and fortunately, I do. I really feel like – again, this sounds so cheesy, but I really feel like it’s my mission or my identity to build With Jack; I just feel like nothing’s gonna stop me, I’m here to do it and I’m not gonna stop until I’ve done it.

Does that worry you at times, that With Jack can be so tied to your identity?

Do you mean in the sense that once I scale and start bringing in staff - does that worry me? Or do you mean like if something was to happen to me, that means With Jack is dead in the water? What do you mean exactly?

That’s a good question. What I’m trying to say is I always find it scary when I attach too much of myself and too much of my identity to the success or failure of something external, like building a business, like a career. Work has to have its own place in my life, but it can’t be my life.

It does make sense.

Or is that not a luxury that you get when you’re building a business?

[17:43] No, I’m very much like – I’m not somebody who’s like 24/7 hustle, all of my life is about With Jack; that’s not the case at all. I have a lot of other stuff going on and making time to do other things, but I think the reason that I’ve invested so much of myself, Ashley Baxter, into With Jack is because I really felt like insurance is so impersonal, and there are so many big faceless corporations, and I hate that. I hate the fact that if I deal with my insurer I’m gonna be speaking to one of 400 people in a call center at any given time… I don’t know anything about the founder… You know, it’s just faceless, and I don’t like that.

That was definitely like a key factor, and when I was wanting to launch my own business, I knew that I wanted it to be a lot more personable. I think it has worked out quite well, especially with just that initial traction. So many people have seen how long I’ve been in insurance, they know how hard I’ve worked to get this off the ground, so they really trust it, placing their business with me and becoming those first customers… So I think that actually really helped me with that initial traction.

So let’s switch gears here… I wanna talk about you and the fact that you’ve taught yourself to code. If I remember correctly, you built a whole Rails app mostly on your own, if not all by yourself, that powered your previous insurance stuff. I’d love to know how it is that you went about that.

You know, some people learn best from just sitting and reading a manual, and then they’re able to process all of that information and then just do whatever it is they’ve read about… And I don’t know what the best method for me learning to code was, and I tried so many things, I bought so many books, and I devoured those books, and then I would also spend a lot of time doing online tutorials… It was different back then; I think I first started trying to learn to code back in 2009, and back then there weren’t really that many options, but I did any sort of online tutorials that I could get my hands on.

I actually ended up going to an evening class at a college to learn Ruby on Rails, and it was there, through that evening class, that I realized “Oh my goodness, there is so much of this that I’m familiar with.” So when I was reading the books and doing the tutorials I don’t really feel like I was learning anything, but now that I was at this course, I was like “Well, I must have been learning stuff, because all of this is really familiar and it makes sense…”

So that one course was really pivotal in building my confidence to keep going… But what changed everything was when I decided to just actually build a proper app. I worked with a designer, Paddy Donnelly, he did some amazing designs for me, and then I just went off and had like a – I just built them; I just learned what I needed to learn to make those designs come to life, if that makes sense, and that really worked for me, because I feel like if I didn’t actually have a real-life project to apply all of that stuff to, I would have just been stuck in that cycle of doing online tutorials for years and not really getting anywhere.

I think everybody’s different… Some people can read books, some people can watch videos… For me, I needed to have a real project built, and that helped me learn to code.

I’d love to hear what you feel are the benefits of teaching yourself how to code.

Well, I think that there’s been a really obvious benefit - I’m a small business, I’m bootstrapped, I don’t have a lot of cash to burn. So learning to code has really helped me just build prototypes and test ideas, see what the feedback is, and then if I think “Okay, this thing has legs”, then I would go to a professional and hire them to build it.

In my talk “Idea to Execution, and Beyond” that I’ve been doing at conferences, part of the advice I give there is to start with the tiniest product version possible. Does that even make sense…? Start with the tiniest version of your product possible. Just recently, I’ve tried to take my own advice with that, because I’ve had an idea… And usually, in the past, I would just dive right in and start building something, but I’ve been setting on this idea I’ve been thinking about, I’ve been doing a bit of research, I’ve been speaking to people… But I just can’t get this idea out of my head, I keep thinking about it.

It’s a very complicated app, and there’s no way I could build what I have in my mind myself… So just today I started working on that, and the idea is that if I can build something basic, that shows the basic functionality, then I can demo it to people to get their feedback and see if it is something people would find useful… And if it is, then I can go and spend the thousands and thousands of pounds that a developer would cost.

[22:29] So it’s been really beneficial in that sense. It’s like, “Save me money, because I’m not spending 7k, 10k on a developer to launch an app that turns out to be completely bombs…” It’s been useful in just like building quick versions of my ideas, testing them, and then if they’ve got legs, I can go to somebody and pay them to do it.

So the last thing I wanna talk to you about is a question that I’ve been asking a lot of people that I talk to these days, which is as creative people, a lot of the times we struggle with burnout, with lack of motivation; sometimes even our mental or physical health plays a factor in how we feel… How have you dealt with these things and still built a successful business?

Well, a few years ago I ended up in hospital with burnout. It was when I hadn’t yet launched With Jack, which was part of the problem - I was really struggling to get that business off the ground, and I knew that’s what I wanted to build… The family business I had taken over wasn’t doing well, and I was also juggling tons of other things, like wedding photography, commercial work, I was doing my podcast… I was just doing all sorts of stuff, but really – not depressed, but unhappy that the business I wanted to build, I was struggling to get that off the ground.

I just kept ignoring the way that it was making me feel and just kept powering through it, and eventually my body started to give me physical symptoms to say like “Hey, you should stop and listen to me!”

I saw various doctors, and all of them kept saying to me “You’re stressed out, aren’t you?” and I’m thinking “Well, yeah, I am”, but I feel really embarrassed saying that to a doctor who’s on their feet for like 16 hours a day, saving lives, and I’m sitting at a computer, messing about with code, or whatever…

So I took a month off, and really just went back to the drawing board and was like “If I could start over from scratch, what would I be doing? Would I be a photographer? Would I be working in insurance? Let’s just say there’s no distractions, there’s nothing stopping me - what would I be doing?” but I think that that’s what got me over that burnout, and fortunately, I haven’t been back there… Is that first of all I took that time to just think and ask that question, and I felt so confident with my choice in insurance.

[24:47] Then when I decided to choose insurance, I made so many changes to my life. I got rid of the podcast, I got rid of the photo works I was doing, I shut down the commercial side of my photography business, and I even started phasing out weddings, like “This is my last year doing weddings.” Don’t get me wrong, I still do loads of things for fun; I play video games, I go to the gym and lift weights, I walk my dog, I love drinking coffee… I do loads of things for fun, but I really just decided work-wise I’m gonna stop saying yes to everything and I’m just gonna focus on the things that take me closer to this goal of building With Jack.

I love that answer, because I just feel like “Man, I feel this all the time…”, that I have so many creative things that I wanna be able to do, that I wanna be able to have time for… I would love to try my hand at making music, I’ve been really enjoying photography and videography, I love doing this show… But there’s only so much of you to go around. There’s only so much time in the day.

Yeah… It’s hard, because you enjoy all of those things as well, and I enjoyed doing the things that I was doing then as well, but I also knew that I wanted to build this insurance company, and I knew that I was never gonna get there by giving it just 50% of my time, or even 70% of my time. I needed to give 100% of myself to it, and I’m much happier, I’m in a much happier place now because of it.


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