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Ashley Baxter

by Josh Pigford. Last updated on February 06, 2024

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This week I talk with Ashley Baxter, Founder of With Jack. We talk about growing up in Scotland, inheriting her dad’s insurance company, the role of design in building great products, using your audience to influence the types of businesses you start and lots more! Enjoy!

Josh Pigford: All right, I am here with Ashley Baxter from With Jack. Ashley, how’s it going?

Ashley Baxter: It’s going good. How are you, Josh?

Josh Pigford: I’m doing well. To kind of kick things off here, I’d love to hear your sort of origin story or where you started. You as a kid, you grew up in Scotland, is that correct?

Ashley Baxter: Yeah, I grew in a tiny peninsula in Scotland that you would have to get a boat to, so I think very much cut off from civilization for most of my life, and then tried to escape that peninsula as soon as I was old enough. It was called Denoon. I think the population’s around about 10,000, so it’s small enough that you’re connected to everybody somehow. Everybody knows your business. It’s just one of those places where there’s not an awful lot happening, so now I’ve moved to the neatest city, which is Glasgow.

Josh Pigford: Oh, nice. How long were you in living in small town Scotland?

Ashley Baxter: Gosh, from the age of six until 17, so went to high school there, grew up there. I was really into music when I was growing up. I certainly didn’t intend to have a career in tech, so it was music. That was what I wanted to do, and as soon as I was old enough to kind of leave there, ’cause there obviously wasn’t much of a music scene there, and I was a drummer. That’s what I ended up studying at college, so as soon as I was old enough, I got out of that place so that I could go the city, start meeting people, play in bands, go to gigs, that kind of thing.

Josh Pigford: How did you get into music to begin with? Was it sort of like just there wasn’t anything else to do, or was somebody in your family into that?

Ashley Baxter: Yeah, it was my dad, who will probably be a recurring theme throughout this chat. He’s been a big influence in my life, and he randomly just came home one day with a drum kit, a full five piece acoustic drum kit, and he taught me how to play a bit. It was from there I became obsessed. I was about maybe 13 at that age, and unfortunately, I wasn’t allowed to take music as a subject in high school. I kind of just missed the boat of choosing it as a subject, so I taught myself drums. It was what I lived for. I was obsessed with it. It consumed me, and I can say to this day that I’ve never felt the same way about anything else as I did about drumming back then.

Ashley Baxter: When it came time to kind of consider what I was doing with school, I thought, “Well, I’m not interested in learning any of the subjects here,” so I left at the age of, I would have been 16, to go to college and study music. So yeah, it was just my dad randomly coming home with a drum kit one day that got me really into music, and I thought I was going to be a famous musician, but clearly that didn’t work out.

Josh Pigford: I think that’s so great. I have three daughters, two of which are teenagers. They’re at an age where it’s hard to find anything that’s super interesting to them. I also have an eight year old daughter, and she’s at the stage where she’s super into anything at all. It’s just everything’s super exciting. But my two teenage daughters are very … it’s everything’s sort of hit or miss with that stuff. I think finding something at that age where you can just jump all in is great, and would stick with you for a while, I mean, maybe for the rest of your life, really.

Ashley Baxter: Yeah.

Josh Pigford: Do you feel like your dad had any idea that you would be really into it, or is it just sort of on a whim he bought the drums?

Ashley Baxter: By that point, I owned a guitar and was just kind of happy to sit in my bedroom and strum away and learn stuff, so I had shown some interest in it, and my dad was quite musical, too. To be honest, I think it was more for him than for me, but it ended up becoming such a big part of my life.

Ashley Baxter: A really great byproduct of it, as well, was that that’s actually how I ended up learning to code to an extent and start building websites, because when you’re playing in bands, your bands need websites. I was always the person who was building the websites and maintaining them, and I really enjoyed that. It was him that also sat me down and showed me how to build my first website for my band, so it was quite a nice byproduct of that music, was that it actually got me into or familiar with building websites.

Josh Pigford: I mean, that’s my exact same story, as far as getting into building websites. I know a ton of people who are the same way. I wonder how many sort of, I don’t know, necessarily former musicians. I mean, I still play some. How many former musicians are now building websites or businesses because they were building them for their bands early on.

Ashley Baxter: I think quite a few.

Josh Pigford: I mean, that’s sort of maybe a byproduct of the timing of the web in general. I don’t what an equivalent would be, but it would be the case with any hobby, I guess. It’s like building a website if you’re into collecting baseball cards or doing any sort [inaudible 00:06:21] hobby, ’cause you’re just building a website for the thing that you enjoy doing.

Ashley Baxter: Yeah, I mean, I’m sure I’ve read a few origin stories of developers or designers where they actually started because they were really into music and they were either in a band themselves and built their band a website, or their friend was in a band, so they built their friend’s band a website, so it does seem quite a common way to get started, actually.

Josh Pigford: Yeah, for sure. So you went to college at 16. That sounds early. Is that?

Ashley Baxter: Yeah, that is early. Well, I was always a year younger than everybody in my class anyway just because of where my birthday falls, so everybody else would have been about 17, but I left at … We have 6 years in high school, although the last two are optional, so I left at the end of fifth year, went off to college to do a practical music course that was designed to teach me to become a session musician. I did that for a couple of years, but a lot changed in college.

Ashley Baxter: The last year of college, my dad became really ill, and he was having heart problems, and my dad ran an online business. It was kind of scary about the outcome of that. We knew that he was never gonna get better, so I said to him my last year of college, I was like, “Look, just train me up on what it is you do just in case anything happens to you.” So I spent some of my second year in college getting trained by my dad how to sort of do what he was doing on day to day basis, because online insurance business, he was kind of a digital broker, I guess.

Ashley Baxter: Then when my two years at college finished, a lot of my friends were going off to study music at university. I was playing in a really great band by this point, and I decided to give myself permission just to have fun that summer, because back then I was 18 by this point. Summers lasted a lifetime, whereas now you just blink and you miss them. So I was like, “This summer I’m gonna go all in with my band and see how far we can take things.” Didn’t really get that opportunity, though, because just a couple of weeks after college finished, my dad passed away, and he left his insurance business to me, so my whole life completely changed overnight from being like, “We’re gonna go all in on this band stuff and try and make it as a musician,” to actually picking up the pieces with this insurance business and trying to keep that going.

Josh Pigford: How do you think the … I mean, the idea that you even were sort of approaching like, “Hey, teach me about the insurance business just in case,” was that something that you ever … Did you feel like would actually sort of end up becoming really useful, or was it a way to, I don’t know, maybe spend time with your dad? What made you take the steps to say, “Hey, let’s just get me familiar with this”?

Ashley Baxter: Well, I definitely didn’t want to … If you’d said to me back then, “12 years from now you’re still going to be in insurance, and you’ll have your own insurance business,” I’d be like, “No way.” ’Cause I had no intention of doing that. I just feel like I didn’t really … My identity wasn’t as an insurance person. It still isn’t. I don’t own a suit. The average age of an insurance agent is 58. I’m nothing like your normal person who works in insurance.

Ashley Baxter: When I approached my dad and said, “Teach me,” it wasn’t because I was intending on actually making a career out of this, but it was more so that he was running a small business. It was really successful. He was doing really well for himself. He’d built up a nice lifestyle business, and if there wasn’t anybody to kind of keep things ticking along, then it would have put my family in a difficult position financially, because it would have been left up to my mom, who just wasn’t business-minded, whereas I feel like I had a bit of experience building websites from playing in bands, and also just helping my dad a bit with his websites, and also I was quite business-minded anyway, so it was really just to kind of step up to the plate and be responsible for my family.

Josh Pigford: Yeah, I think even for an 18 year old, that’s a sort of a big weight to carry.

Ashley Baxter: Yeah, you’re telling me.

Josh Pigford: Was it just you, sort of? Did you feel like you were all by yourself having to handle all that or shoulder all that, or did your whole family sort of step up to that, too?

Ashley Baxter: Well, no. So there was my mom and then my sister, who was away at university studying her passion, which is fashion, and she’s been able to turn that into her own business, which is great. The onus was on me, which was really stressful, but at the same time, I seem to be one of these … I seem to respond quite well when I’m pushed into a corner. Some people might crumble under pressure, but I actually work really well when I’m pushed into a corner. There was no alternative other than to do this and to learn as much as possible and to make this work. There was no alternative, so I responded quite well to that in that I just put my head down and learned a bunch of stuff.

Ashley Baxter: The very first thing that happened was the insurer that we worked with flew me down to London and I sat with their in-house developer, and he was the one that introduced me to CSS. ’Cause at this point when my dad was teaching me how to build websites, this was back in table-based layout times. Remember that?

Josh Pigford: Yeah.

Ashley Baxter: So the next step was to actually learn how to do this stuff properly, and then obviously, back then search engine optimization was a big thing, so I just had to learn. Like I said, I responded really well to the pressure. I just had to do it.

Josh Pigford: Obviously, you’re having to shoulder and deal with the weight and all the emotions that come with your dad passing away, but I mean, at the same time do you feel like it became something that you enjoyed relatively quickly?

Ashley Baxter: Yeah.

Josh Pigford: Was it just like, “I’m just having to dig in and just because it’s what sort of required of me”?

Ashley Baxter: Well, in the beginning, for the first several years, I hated it and I was very much the kind of person that I said I’d never become, which is somebody that lives for the weekend. I don’t know about you, but when I log onto Facebook nowadays on Sunday I see a bunch of my friends talking about the Sunday dread, because they hate what they’re doing, and that’s how I felt at the time, too.

Ashley Baxter: But something did happen a few years into it. I knew that I wasn’t passionate about insurance. My dad’s business was landlord’s insurance, so I knew I wasn’t passionate about landlords. The buy to let industry doesn’t really excite me, but the one side of things that really was a saving grace was actually the design and development side of things, like actually wire framing websites and then setting down at a computer and making them come to fruition, and then watching people interact with them, and then getting the reports every week to see x amount of people bought insurance this week. Really enjoyed that.

Ashley Baxter: So I ended up throwing myself into the web industry, and I started going to maybe two or three big conferences a year, and then some smaller meet-ups, and I started following a lot of well-known designers and developers on Twitter, getting really involved in Twitter, started buying the magazines. That changed everything for me. Through doing that and through meeting some really talented people in the web industry, it made me realize how much design and technology sucked in the insurance industry. It’s getting much better now, but it was really bad back then. It was nobody doing anything interesting with design and tech and insurance.

Ashley Baxter: Suddenly I was like, “Well, okay, I’m not passionate about insurance. I don’t care about landlords, but I really want to make it my mission to improve design and technology in the insurance industry. Not on a massive let’s destruct the whole industry scale, but just what can I build in my small corner of the web that looks good and functions good? I was still doing the same job. I was still doing the same work. I was still serving the same audience, but just that shift in attitude and having a mission that I felt like I could really get behind, that suddenly meant that I started really enjoying it.

Josh Pigford: You’ve kind of had this sort of change in mindset. That makes things more enjoyable for you, but all this is still under the umbrella of Brokers Direct, the company your dad started, right?

Ashley Baxter: Yep.

Josh Pigford: At what point did you decide to sort of go out, start your own thing from scratch?

Ashley Baxter: Well, I found it really hard to walk away from my dad’s business, because I felt like it was quite sentimental to me. I was very emotionally attached to it, but the business wasn’t doing very well. A couple of things happened around about the time my dad passed away that actually completely changed the insurance industry.

Ashley Baxter: The first was that there was a big boom in comparison sites. Our whole business model was actually, or my dad’s business model, was building as many websites as he could and getting them ranked on the top of Google, and that worked really well for us. At one point when you were searching for landlord’s insurance, my dad’s websites would have accounted for maybe six or seven of the first page results, and that was how we got all of our business. That worked back then, but all of a sudden everybody was flocking to comparison sites, so we weren’t seeing as much business anymore, and we couldn’t afford to get on these comparison sites, because they were really expensive.

Ashley Baxter: The second thing that happened was that Google obviously made their algorithm a lot more sophisticated, because back then it was all about on-page factors, keyword stuffing, things like that. They made it more about social and content and our rankings suffered as a result, so the business wasn’t doing that well.

Ashley Baxter: Like I said, I in the meantime just became obsessed with the web industry, and I really, like I said, gave myself this mission to improve design and technology in the insurance industry. The bread and butter of any insurer’s website is, of course, their quote system. Like if somebody’s coming to my website, it’s probably ’cause they want to get a price for their insurance, right?

Josh Pigford: Right. Yeah.

Ashley Baxter: So I really wanted to focus on improving the quoting and buying experience. Now, the insurer that we worked with Brokers Direct, I spent some time learning Ruby on Rails, and then I built this prototype of a quote system, and I flew down to London and demoed it to this insurer and basically said, “What you have right now isn’t very good, and here’s why,” and I showed them a bunch of bugs when I was using their system. I said, “So I’ve built something that I think is better.” This was way back when responsive design was just gaining traction, which means that the insurance industry would have taken another two or three years to catch up with all of that, ’cause it moves so slowly.

Ashley Baxter: So I’d built this responsive quote system. It was mobile first. Took it down there, demoed it to them. I wasn’t sure what to expect. It’s a bit arrogant now that I think about it. I mean, I would have been 25 at the time. This 25 year old girl telling them that what they’d built was rubbish and I’d built something better, but they actually loved it, so much so that they ended up essentially offering me a job on the spot to come and build this for them, to oversee a team, and build this quote system for them, for them to roll out across their platform, which had hundreds of brokers.

Ashley Baxter: I was like, “Wow, I’ve made it. This is it. It’s not that I want to sell landlord’s insurance. I want to do this. This is enabling me to achieve that mission that I had of improving design in tech,” so I was all in. The long story short, that never ended up happening, although they never turned around and told me why. My feelings and things that have been hinted at the conversation that I had with them was that they would have had to have given me a lot of sensitive information to start building this, and I just don’t think they felt comfortable giving me that information.

Ashley Baxter: After basically a year of having this carrot dangled in front of me, I realized, “Okay, this isn’t happening, and I’m not wasting any more time on this,” so that was when I decided to basically just walk away from everything that was to do with my dad’s business, and also trying to build this quote system with them. That was when I started thinking about my new business, which eventually became With Jack. That was a really long answer. Sorry.

Josh Pigford: That was fantastic. It’s really interesting to me what become sort of the catalysts for businesses to start, because I mean all of us have an infinite number of ideas and things we could do, but I think it’s really interesting what sort of becomes the thing that makes us do the thing.

Ashley Baxter: Yeah.

Josh Pigford: So for you it was just you felt like there was this thing that got you really excited, and it just drug on for a long time. I mean, that’s got to be exhausting. After this company basically just doesn’t do what you had hoped that they were gonna do, I guess, what made you want to not just go back to what you had been doing with your dad’s business and what you had been doing for the years since that? What made you decide I’m gonna start something new and not let this sort of keep me down?

Ashley Baxter: Well, something interesting had happened in that time. Because I had taught myself to code and because I was in this stuffy industry where there wasn’t a lot of innovation happening, and because I didn’t look like a normal insurance person, I started getting invited to speak at the conferences that I’d been attending. I started getting invited to speak at conferences and meet-ups and stuff, so I found myself … These were small conferences, maybe 200 people, but I found myself speaking to maybe 200 designers and developers about what I was trying to do with technology and the insurance industry, but I was selling insurance to landlords. It didn’t actually make sense to me. I was like, “Why am I …?” Do you know what I mean?

Josh Pigford: Yeah.

Ashley Baxter: “Why am I standing on stage talking to this group of people when I’m selling landlord’s insurance?” Also, I don’t know if you agree with me, but I think it’s really important to work on a business that is serving an audience that you want to sit down with them every day and grab coffee with them every day for the next, I don’t know, five, six, seven, ten years.

Josh Pigford: Yep.

Ashley Baxter: I didn’t want to do that with landlords. I couldn’t get inside their heads. I didn’t know what pains and frustrations they had, and I just didn’t have the drive, enough of an interest in them to figure that stuff out. That was really the point where I decided to start my own thing, which would become With Jack, and it made sense to me to start selling insurance to web designers and developers, because that’s the audience that I was already in front of.

Ashley Baxter: If that sounds like a really naïve way of deciding, “I’m gonna start a new business, and this is who my audience is going to be,” then it probably is a really naïve way of doing things, ’cause if I had actually done some research about this, I would have learned that, first of all, most freelance designers and developers don’t actually have insurance, because they don’t know what is. They’re not thinking about that kind of thing.

Ashley Baxter: Secondly, that their premiums for those that do think about insurance and want to buy it, their premiums are really small, so you would actually have to have a ton of volume to make some good money for this as a business.

Josh Pigford: Right. To your point about being naïve or not, I mean, there’s a couple of aspects there that I think are important that a lot of people end up going a little too clinical when they’re looking at that stuff is … It’s super important that you enjoy the customers that you interact with, right? I mean, to me that almost is more important than even maybe the business itself or the industry it’s in. You could have no interest in landlords, but you might really enjoy landlords as humans.

Ashley Baxter: Yeah.

Josh Pigford: So it becomes an interesting thing, but obviously at the same time, it makes practical sense also to sell something to the audience that’s available to you. I think of Laura Roeder from Edgar. She was able to launch this social media product to an audience of hundreds of thousands of people who are really big into social media stuff, because she had built that audience. It would have been silly for her to launch something totally separate when she has this massive audience built in that is sort of like an instant set of customers, right?

Ashley Baxter: Mm-hmm (affirmative).

Josh Pigford: For you, with selling insurance to … I mean, right now you’re primarily focused on freelancers. What’s the hardest part of that? I mean, is it just convincing or educating them that they even need it?

Ashley Baxter: That’s exactly what it is. When I first started With Jack, ’cause we’re currently completely rebuilding the website and even the quote system right now based on just what I’ve learned from launching this business a year and half ago. At first, I thought it was straightforward. You build a landing page. You get people on it, and then you sell them something. But actually, freelancers, they need a lot of education as to why they need insurance, and that’s what I realize my job is now. It’s not to sell them insurance. It’s to educate them about the kind of situations that they can find themselves in that lead to them needing insurance, and I can do that now, because now that my business has been going for a year and a half, we’ve obviously had customers who have had to use their insurance, and it’s obviously a really horrible situation for my customers, because it usually stems from somebody threatening to sue them.

Josh Pigford: Right.

Ashley Baxter: But it’s been really good for me to see what actually results in a freelancer needing to have insurance in the first place. Now we’re completely rebuilding the website from the perspective of having to educate them, basically. That’s what my job is now. I think of it as it’s I’m not selling insurance. I’m educating freelancers about why they need insurance. Right now if you go onto With Jack’s website, our slogan is business insurance on a first name basis, because I want With Jack to be really personable and not like other insurance companies, which are massive corporations, typically faceless and have no personality.

Ashley Baxter: Now I’ve realized, I’ve completely redone our pitch, because I’ve been thinking about what problem is it that With Jack’s actually solving, and I’ve realized that it’s 44 percent of freelancers will be stung by a bad client, so what we’re building is a platform that helps them financially and legally when that happens. I’m actually trying to get away from the word insurance as much as possible.

Josh Pigford: What does that shift mean practically? Obviously, educating, but I mean, does it change what kind of products you guys offer?

Ashley Baxter: It will do. The insurance industry is a really tough thing to get into. At least it was for me, especially ’cause I had such an unconventional background. People who work in insurance typically start at a company and then work their way up, and you’ll see a lot of people now leave those companies to start their own insurtech start-ups, as they’re called. I hate that term, but that’s what people are dubbing it. Whereas I obviously had a really unconventional background and I had no connections, really, in the industry. It’s been difficult for me to get started, but my plan of attack is to just keep doing what I’m doing, which is focusing on first of all educating that I’ve just spoken about, but also making the process of getting insured so simple, and also have freelancers understand what it is that they’re buying. Then build up my customer base, so that I finally get to a number where I can start going to the insurer, working really closely with them, and iterating on the actual product itself, which is something that I’m already seeing happening.

Ashley Baxter: Just last week, the insurer that I work with got in touch with me to ask me if I could survey my customers on something, because they were thinking of making a change to the product, and I was like, “Yes, this is exactly what I want to go for.” I’ve kind of had to start at the bottom, which means first of all, manual processes. Our quote system isn’t yet automated. That’s in the works, so I’ve had to start by manually processing every quote that comes through. It also means just selling my customers a product that the insurer has given me, which is fine, because it actually works and does a good job, but obviously I want to switch to a fully automated platform so everything’s done without me having to be involved. Secondly, actually start working with the insurer and my customers to create a product that’s better tailored to them. But it’s an iterative process, as you can imagine.

Josh Pigford: Sure, sure. When I think anybody thinks insurance they think dominated by massive corporations. It’s all kind of very … it feels a little mysterious, how any of it even kind of works. It feels like there’s so many hoops you have to jump through, and you always kind of wonder. You’re buying a thing for something that may never happen. You may never even need it, but it’s such an unusual product to have to go and buy. I think to run a business that’s selling that, how do you stand out to not become, or how do you not sort of step in line with the way that everybody else has been doing things, and make it better?

Ashley Baxter: Yeah, that’s a good question, and I will admit I haven’t yet figured it out, but what I really want to do With Jack is move away from just … I don’t want With Jack to be just an insurance company. I actually want us to build a platform that generally just helps freelancers with their businesses. Now, I’m not sure what that looks like yet. I’m doing so much customer development stuff, ’cause back in the day I used to just have ideas and then sit behind a computer and code them and make them happen and then they would flop, because I actually hadn’t validated that there was any need for it.

Ashley Baxter: Just recently, I know that my vision is to make With Jack more of a platform that helps freelancers with their business, so I’ve been doing a lot of speaking to my customers, jumping on half and hour, one hour video calls with them, and just having a general conversation to see if they say anything that sort of makes me think, “Well, actually, I could build something to help them solve that.” I’ve also been doing surveys with my customers, which I’m using a tool called [etoday 00:31:09] to do that, and also been even trying to speak to lapsed users, people who never signed up. Then even something as simple as yesterday or two days ago, I did a Twitter poll where I was asking freelancers what their biggest problem is.

Ashley Baxter: I’m just trying to collect all of this data right now and this information around what problems freelancers are having, so that I can figure out what it is that we’re gonna build into With Jack to make it even more valuable, because at the moment, we have hundreds of customers but only a handful of them have actually had to use their insurance, which is a good thing, ’cause it means that bad things aren’t happening to the other people, but it also means that they are, like you kind of touched upon, they’re paying for something and not really getting the full value from it. Although, when I speak to my customers they say, “Well, that’s not true. We’re paying you for peace of mind and we get that just by paying you money every month.” But I am, at the moment, exploring what the next feature we’re gonna build into With Jack is to create better value for everybody, and I’m not quite sure what that is yet, but I’m working towards it.

Josh Pigford: Going back to sort of the beginning of your business journey with inheriting your dad’s business, how would you describe the way that your dad would run his business versus how you’re doing things now? Do you feel like it would be sort of this … I don’t know. I guess, for you, are you like your dad in that sense, the way that you run your business, or do you feel like you’re very different in that regard?

Ashley Baxter: Well, we actually have kind of done things differently because my dad’s business … Insurance is a regulated industry, and there are various tiers, so to speak, of regulation, and he was kind of at the very basic level where he wasn’t actually allowed to interact with his customers. Essentially he was an affiliate. He build a landing page, people registered their interest, and then were sent to the insurer. What I’m trying to do is definitely a bit more involved than that. This is probably my favorite part of building With Jack is just speaking to my customers and getting involved with them and learning about their businesses. I’ve had to become authorized to be able to do that, so there’s already a big difference there, in that he was very hands off with his customers and just built a landing page and then people would have to deal with the insurer, whereas I’m a lot more involved in it, not just in the buying process, but even when customers are making claims as well, so there’s definitely a difference in our businesses there.

Josh Pigford: Gotcha. What’s a topic that when somebody asks you about it you get super excited? For me that’s anything to do with automating anything, cars, robots, anything like that. What’s a topic for you that you get super geeked out about?

Ashley Baxter: Can I say two things?

Josh Pigford: Sure, yes. You can say three if you wanted.

Ashley Baxter: Well, there are two things that really excite me at the moment, and they actually both contradict each other. The first is, like I said, I hate this term, but the insurtech scene. Once a week, I’ll go to my local craft beer shop and I’ll get some cans of beer, and I’ll sit at my computer one evening a week and just see what’s coming out there. There’ll be a list of websites I go to and just keep on top of what interesting insurtech start-ups are coming out of the scene.

Josh Pigford: Okay.

Ashley Baxter: Yeah, that really excites me, seeing what’s coming out, what people are coming up with. It’s a big kind of VC scene. A lot of the insurtech start-ups have VC funding.

Josh Pigford: Sure.

Ashley Baxter: So then that’s one side that excites me. Then the other is I get really excited about the opposite to that, the indie maker scene, so people who are solo founders and they’re bootstrapping their start-ups to profitability. They’re not thinking about exits. They’re just people like Paul Jarvis who are building companies that just suit their lives instead of going for the billion pound exit type of thing. So those are the two topics that are interesting me right now, and I’m trying to learn as much as possible about.

Josh Pigford: I mean, how do you balance those two contradicting things, right? Especially when both sides can, on some level, be kind of dogmatic about, “This is the way to do it.” I mean, both sides think that’s the way to do it, and obviously, it usually ends up being some sort of gray area in the middle. But how do you not get sucked into one way or the other, and sort of keep a balanced perspective?

Ashley Baxter: Well, I actually read one of your blog posts that I thought was quite interesting where you talked about your perspective of having bootstrapped a bunch of start-ups, and then taking funding, and it sounds like you did it all for the right reasons, right?

Josh Pigford: Yep.

Ashley Baxter: But for me, I don’t know, it’s just-

Josh Pigford: Really, it’s sort of like the VC funded, how do you keep from getting sucked into the I have to go the VC route and grow this thing as big as possible and it’s hockey stick growth or bust, or kind of going the indie route where you do sort of what you want when you want?

Ashley Baxter: So to be honest with you, this has been a big struggle of mine. It’s because I’m watching all of these start-ups coming out and then sharing space, and they are all VC funded. Last year, I actually dipped my toe into the water of the investment scene myself when I applied to join an accelerator.

Josh Pigford: Yep, yep.

Ashley Baxter: I wasn’t actually successful with my application, but I learned a ton from the whole process, actually going through the interview process and sitting down with angel investors and setting down with VCs as well. But for me, I’ve just realized that I would never say never, but I don’t know if that is the right route for me. I think about the kind of person I am and the type of life that I want to lead, and I look at my friends who are in the start-up industry and have raised five million in investment, and they’re constantly getting pulled away from the actual work to raise more money, and then they’re constantly on planes flying around the country meeting investors and things like that. I think about the kind of business I want to build and the life I want to live, and I just don’t think that that whole route is for me, but I’d never say never.

Josh Pigford: Sure. I mean, and I’m the same way. I have strong views now on taking VC money again, and I think there’s so many just sort of situational things where what I think today may not be the case at all in even a month.

Ashley Baxter: Yeah. It is really hard when … It’s so hard when I’m keeping tabs on this space, and it seems like that’s the route everybody is taking, but again I think that that’s because they have the intention of trying to take, for example, the market I’m targeting. Freelancers, there’s two million in the UK, so if you have somebody who takes VC funding to target the freelance market, they’re obviously doing that ’cause they want to take a massive slice of the market. Whereas what I think I’m happy doing is having … You know the whole 1,000 true fans philosophy?

Josh Pigford: Yep, mm-hmm (affirmative).

Ashley Baxter: I think that I’m happier going down that route and having a really small but engaged community of freelancers who love using With Jack. That’s what I think I’m more into, but it can be so difficult when I’m watching everybody else doing it and getting investment. But that’s what I think I’m more invested in is the 1,000 true fans.

Josh Pigford: I think, so it’s easy for me to get caught up in that too. You see somebody, you get some like, “Hey, we just raised 50 million dollars,” which is obscene, but you think like, “Whoa, imagine all the things I could do with 50 million dollars.” But at the same time, I can also talk to so many founders after the fact who maybe got some sort of exit or were forced to do some sort of exit because they ran out of money or whatever.

Josh Pigford: Really, if you look at all the numbers, the amount of people who actually come out sort of better off than when they started their start-up who took on funding, it’s not that many. There’s so few cases where take on tons of money and VC investment where the person comes out a happier person on the other end.

Ashley Baxter: Yeah.

Josh Pigford: It’s actually pretty rare.

Ashley Baxter: Yeah, and also, actually when I think about it, ’cause like I said I’ve sort of been thinking about this stuff a lot recently, insurance is one of those industries that people don’t really trust. There’s a lot of negative connotations. 73 percent of people don’t trust their insurance provider.

Josh Pigford: Yep.

Ashley Baxter: So I think the fact that if you take VC funding, and again this definitely won’t be the case all the time, but when you take the funding, you’ve obviously got even more people to please that aren’t your customers. You’ve got the investors to please, whereas what I really like about With Jack is that the only people that we have to please are the customers. That’s all that matters. But the frustrating thing on the flip side about bootstrapping is that I have all of these really fun, interesting ideas I want to explore, but I’m so restrained with the cash that I have. Obviously there are pros and cons.

Josh Pigford: Yep, totally. I think a really positive thing about an industry like insurance is it’s not this sort of new flashy thing. It’s been around for a long time, and it will be around for a long time. I mean, it will obviously look different over time. You’ve got time, and you can take your sweet time figuring all this stuff out. There’s no rush in that sense.

Ashley Baxter: Yeah, it does feel that way, and I know that there are people starting to spring up and change how the insurance model works, like on demand insurance is quite a big thing right now, but I actually think that the traditional insurance model works really well. The only things that I don’t think that work are the fact that the insurance just has these negative connotations, and that also, especially in regards to my audience, people don’t generally understand what they’re buying.

Ashley Baxter: When you shop online, you’re filling out forms, and it’s usually littered with legal jargon that you just don’t understand, so if I can create this company that, again going back to that 1,000 true fans thing, has this small but engaged user base, people who trust that we’re gonna be there for them. ’Cause at the end of the day, With Jack works for them, not the insurer. If I can build that, and also just make the onboarding experience a lot more straightforward, and if I can have people understand what it is they’re buying, then I think that long-term, I think that that should work.

Josh Pigford: Yeah. Totally agree. I think that’s all I’ve got on my end. How can people get in touch?

Ashley Baxter: I’m pretty active on Twitter, so that’s IamAshley on Twitter, and also, I’ve started putting a bit more effort into my newsletter, so I want to plug that.

Josh Pigford: Sure

Ashley Baxter: That’s at, and I write all about bootstrapping and insurance business as a solo founder.

Josh Pigford: Awesome. All right, well, that’s all I’ve got. Thanks for hopping on the call, Ashley.

Ashley Baxter: Thanks for speaking with me, Josh.

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.