Dave Berner - Co-founder & CTO at Parachute

Welcome to another Founder Wisdom podcast. We have Dave Berner with us. Dave is a co-founder at Parachute. He helps overworked lawyers save time with AI in Byron Bay, Australia, coming back from the gym. Dave, welcome to the pod. Tell us a bit more about yourself and how's it going?

Hey, Charles. Yeah, good, thanks. Yeah, literally just got in from the gym, fed the kids breakfast, and straight on to this. Yeah, a little bit disheveled, but it's all just part of the founder juggle, right? Just kind of keep all the balls in the air at the same time.

Well, you got the blood flowing, so that's good. I forgot my— I didn't forget, I didn't do my morning dog walk this morning. My brain was all over the place. So at least you have that going for you.

Oh, 100%. I feel like where everything else in startup life is so chaotic, just having that like set kind of morning routine, at least that kind of, that constant just sort of sets me up for the day. And as you say, kind of getting the blood flowing around the body, oxygen pumping around brain, ready to go, and just giving my brain a bit of space to think.

What are you building? Tell us a bit more about the company.

Yeah, so I'm working on a legal AI platform, so targeting sort of mid-tier law firms who are like helping them with document drafting or contract review, who kind of plugs into their emails, to their teams, to, you know, all their different systems, their PMS systems, CMS systems, document management. So effectively kind of manage that whole workflow and save them time so that they can spend more time at the beach with their kids or earning more money, I guess, depending on, um, yeah, what they love to do in their free time.

You're a software engineer, right? Uh, but that's not your first company. You started one called, uh, Web Superheroes in 2010. Tell us a bit more about your background.

Uh, yeah, I mean, that was more of, I guess, a web design agency that myself, um, and a friend, Bord, created. It was kind of like a side hustle from our— we were both working in in finance on the phones and we were just sort of building websites for small businesses. I've always kind of had that, I guess, that entrepreneurial spark to want to be able to do something on the side and always kind of had a love for the web and building things out. So that's probably where all the kind of foundations of where I'm at now began.

Interesting. And your first big one, Kindy. Is that how it's pronounced? I think it was the largest seed round right back then.

That's right, yeah. So it's pronounced Kind, uh, but I kind of like Kindy because it's, you know, playful and, you know, didn't like to take ourselves too seriously, which is interesting considering we were in authentication and access control. But yeah, that's right, we raised, um, Australia's largest seed round I think it was like $10.5 mil, something like that. Grew that to 50,000 businesses kind of around— I started in Australia but then grew to Canada, US, UK, Europe. And now, yeah, I've kind of progressed from there on into the AI space. Seems to be where everything's heading. And yeah, lawyers are super fun to work with, like very blunt and direct with their feedback, which is great, um, as opposed to engineers who when you pitch something they're like, oh well, I'll just build it. So it's a very different audience for sure.

And this one you built, I think some of your co-founders were from Atlassian, right? You were from Campaign Monitor. I know about Atlassian, I don't know about Campaign Monitor. Was it another Australian legendary company?

Yeah, Campaign Monitor, I suppose, probably akin to companies like Mailchimp in the email marketing space. But they were one of the kind of big blow-up startups out of Australia, probably around 2010, I want to say. And they've now grown to be the Marigold Group and they own I don't know how many other companies kind of underneath that umbrella. But yeah, they were kind of one of the first big ones around the same time. You'd see a lot of stuff sort of swapping between Atlassian and Campaign Monitor at that time. I mean, this was all sort of pre-Canva, who I guess are the kind of big Aussie startup that you hear a lot about these days.

Yeah, yeah. And that one kind— did you have an exit? You stayed there 4 years, the VP engineering product role. How was it for you? I mean, that must have been like a rocket ship, right?

Yeah, for sure. Um, so started that kind of 5— been like 5 years ago, I guess. So that kind of zero to one phase is definitely my happy place, I guess. Um, I haven't exited yet, so that's still, um, I still have equity in the business and that's still, um, still kind of going along and growing month on month.

Uh, happy place. Does that mean that like anything after 0 to 1 is like hell, like managing people and just like the, the noise, noisy part? I mean, not the noisy part, but like the structuring and the systematizing part, which is more like corporate and less challenging, one could say.

Yeah, I think it's that like those early stages where you're all kind of definitely feels like more like a team mentality and you're all kind of striving towards that common goal. Probably up to like, you know, say like beyond 30 people, I find like it starts to change once you can't— you don't know everyone's name at that point. I mean, you know, it's obviously an awesome stage to get to, but I find like the part that's the most fun, or whenever I reflect on companies that I've worked at, it's always those— the kind of smaller stages that I look back on as being like the best times of that company.

And tell me, like, I mean, you said, uh, 0 to 1, right? That's exciting. Authentication, isn't it like a boring business in itself? Like, how does, uh, one survive that in itself? It's like, uh, it's always the same thing and it's security. Isn't that— didn't you not choose like the right company concept?

Yeah, I think the interesting thing about it is one, boring problems are usually the ones that people don't want to solve. I believe there is kind of a moat in and of that. It's also one of those which I believe you don't necessarily want to palm off to AI. You probably do actually want that kind of trust layer there. And I guess it's kind of like an insurance policy in some way. But as an engineer and always have been, working with and for engineers was always a huge part of that. It meant that I could be involved in sales conversations and, you know, I could really understand the problems that these companies were facing and kind of help them to, to solve those. So my, my love is in that, like, the startup space, and the whole vision for the company was really to enable other startups to get to market as quick as possible so they didn't have to worry too much about authentication, billing, feature flags, all the kind of building blocks to enable them to get to market as soon as possible. Round chickens. That's the fun thing, just seeing kind of what people built and had some phenomenal companies come out of that, like Heidi Health, for example. We've sort of seen them absolutely blow up. They were kind of one of the early companies. Yeah, it's just great to see.

Are you around chickens?

Yes. Can you hear them in the back? Yes.

What's your life nowadays? You live on a farm? Like, what's, uh, how did you engineer that around you?

Um, so I live up just outside Byron Bay in a little town called Bangalow. I think it's like 2,000 people here, so it's pretty, pretty small. Um, you know, I have 13 chickens and 3 children, which keep me pretty, pretty busy, and then a decent supply of eggs. Um, how do I engineer that? I think I love coming to the office and I love when I travel down to Sydney to catch up with the team as and when I can. But I do believe that you can work from anywhere and be as effective, probably depending on your stage of career. But I feel like I've got the greys in the beard to show that I've been around long enough that I kind of know what I'm doing and I can do it independently. So we spent a little while traveling around in a caravan for about 4 months, kind of round outback New South Wales, trying out different places, and ultimately ended up settling on Bangalow. Just had like a really nice kind of community spirit and family vibe. There's actually tons of entrepreneurs and founders up in and around kind of the Byron Hinterland and quite surprisingly, a vibrant tech community up here. We all retreat to our holes and then once a week we'll all come out, get together, have a few beers, coffees and catch up, which is great. So I guess I actually came backpacking here a long, long time ago and ended up settling in Sydney because there just wasn't the work available and remote working wasn't really a thing at that time. I was probably one of the earlier ones to kind of move into that more remote type working, kind of like pre-COVID. And now it just seems like there isn't really an excuse for not doing it.

And what does a day in your life look like nowadays? You wake up, you start with the gym. Uh, that's what I referred, uh, by what— when I was saying engineering, right? Like, what does a day in your life look like? How did you optimize every step for performance, I guess, but also spending time with the family?

Yeah, for sure. Um, I guess like I'll map out like what the constants are through the day. 1st. So yeah, that will be setting an early alarm. I'm out of the door by 6, in the gym by about quarter past. Then I'll come home, set the kids up with some breakfast, hop on a podcast, which I didn't actually realize I was doing. I thought it was a pre-call, but I still just jump in because you just never know what's necessarily going to happen. So the kids are all in the house eating breakfast now. I'll come in from that, I'll take them to school. After school, drop off, I'll probably do like a beach walk for about half an hour, leave my phone in the car, just kind of have that time to clear my head and reset. That's when I'll then come home and start the day. From school pickup is then quite early for us, it's like around 2:45. So there are like those few constants throughout the day. So I have like a focus block of work. Where I'm kind of like trying to take as few meetings as possible. If I do have meetings, I try to front-load them to the start of the day, which is counterintuitive in some ways because my brain is probably most engaged in the morning. But I find if I stack my meetings towards the end of the day, then I just don't really have the energy for them. So I front-load them, and then I know that I've kind of got the rest of the day. It's just like clear for engineering, development, strategy. The other thing I like to do is kind of block my days out. So I might have an engineering day or a strategy day or content day, just because like in this kind of AI world where you can do 50 tasks at once, it doesn't necessarily mean that you're doing all those things well. And that constant context switching definitely doesn't help. So I try and kind of theme each day with something that I kind of want to achieve in a specific lane. Then post-kid pickup, if it's a nice day, we might go to the beach for a little bit after school and then come home and I'll work again through the evening. So it's kind of that balance between— I don't think you have to be tied to your desk from 9 to 5. It's kind of when is going to when are you going to get your most productive work done at the hours that work for you? And so long as the output's there, that's what matters. And that's the same as what I encourage for the rest of the team as well. There's no expectation that if I call, they're necessarily going to be there, so long as they're getting the work done.

And what do you think about walking on the beach?

What do I think about it? Oh, what do I think about whilst walking? Yeah, could be anything. I try to leave my phone in the car and just think about business. Yeah, sadly, your head does go there. Like, you start off and you're kind of looking out over the sea and then sadly it does end up kind of creeping into your thoughts. Usually, I suppose, I'll do a lap up and then a lap back down along the beach. And then as I'm getting back towards the car, yeah, starts to creep in at that point.

Okay, but what precisely? That's a question. And where that— where I'm getting with that is like, what's stressing you nowadays, or what's the number one problem to be fixed in the business?

So we're going through a capital raise at the minute, so that's always just quite a time-consuming activity. Um, so yeah, just thinking, overthinking investor calls and You know, that whole kind of like, should I think about that VC that ghosts you? And yeah, and then the one that got on really well and then isn't interested, and the one where it went horribly and they suddenly want to throw money at you, and you're just like, I don't understand, these two calls went in completely different directions and neither ended up—

doesn't make any sense, it's like too complex. Yeah, sometimes when you try to reverse engineer humans and their thinking, it's just too complex, right? Because Not only humans are complex creatures, but they hide their cards, right? So they won't tell you the why exactly. You could get down to that why maybe if you sit down, do an ayahuasca trip with them. But other than that, they wouldn't tell you why.

Yeah, 100%. Yeah, always going to keep their cards close to their chest. And it's that constant battle between what the founder wants and what the investor wants, I suppose.

Other than fundraising, what, what else? Like, I'm guessing Due to your background, like, uh, hyper obsession on product, right, and building something great. What about go-to-market, right, like any sales activities going on?

Yeah, so we've grown— we've been in market 6 months, um, we've been growing like pretty significantly month on month, which has been awesome. Um, the sales I can't get involved in as much with this business. I, I have done a few calls. It's definitely quite a humbling experience, uh, as an engineer trying to sell to lawyers, but Our go-to-market team are all lawyers.

But wait, warm leads or cold calls?

Usually warm. So we will—

Okay, that's not so bad. Like, if you really want to be humble, just pick up the phone and cold call them. Yeah, always a great exercise.

I mean, I did a stint of door-to-door sales when I was younger, just knocking on doors trying to sell people alarm systems. So maybe security has always been like—

Oh boy. Yeah, that's the worst one.

Um, are you still traumatized? Yeah, a little bit. I think I'm still a little bit scarred.

One dude, one Australian dude pursuing you with a shotgun. Get off my lawn!

Well, I'm actually British, so I grew up in London, so I mean, really?

Yeah, interesting.

Yeah, I've been in Australia about 14 years.

I don't think they have guns, uh, much guns in the UK.

No, no, they just like to fist fight and throw stones.

Oh man, that's good. Um, so lawyers, right? Like, why did you pick lawyers? Aren't lawyers, like, talking about boring, right? Like, why pick that segment? I know there's a lot of money to be made there, but why I picked that ICP precisely?

So for me, actually, a lot of it was to do with the, like, my co-founders. So my co- I've got two co-founders, Viv and Ryan. Uh, Ryan is an ex-lawyer. He was at Eucalyptus as their in-house legal. He's been at big law. He started his own law firm. Um, so kind of had a bit of a mix of an experience with like big law and startup energy. And we just hit it off kind of after the first couple of calls really. And I think sometimes kind of having that chemistry, somebody that really understands the market and you know, we're talking about moats, and he's like, well, I don't think product's the moat anymore because with AI everything can be built so quickly. So I think it's distribution. I can distribute. I'm like, cool, I can build. So it just seemed like one of those partnerships that made a ton of sense.

There you go. You had a podcast before. How did that go for you?

That was great. I really enjoyed that. I'm actually kicking off a new one. I'm doing my first recording today, actually, for Risky Business. So it's going to be speaking to sort of founders and operators in, I guess, sensitive areas, whether that's like legal or health or fintech or anywhere where there is— yeah, you kind of have to get everything right because there's real consequences if you don't.

Compliance.

I loved it from like— and hence why I'm kind of kicking it off again, probably for the same reasons that, that you do. But for me, it was just meeting so many smart people, learning things from them. Like, every conversation you'd come away with some learning or some, like, different way of thinking. How about yourself? How— you, you've obviously taken that same path.

Hyperscaled did, yeah. I interviewed, uh, 3,000 CEOs and founders and It's a great, it's a relationship accelerating machine, right? So a lot of people start their podcast for content or I don't know, to be the next Joe Rogan. Me, it's really to accelerate and scale relationships. And ultimately I get clients off that. Actually, you'd be a great client of mine 'cause you're starting your podcast and you're raising, right? Which is two things that I do, go-to-market and fundraising. And I'm inherently curious, right? So back then I would just listen to a bunch of podcasts and just classic founder, like, hey, let's start my own. I think I can do better, right? Like classic founder arrogance. I was listening to Tim Ferriss back then, John Lee Dumas, and the classics, right? Like Joe Rogan. The podcast you were interviewed on, I listened to as well. Was it Startup Story? Or something like that.

Oh yeah, um, yeah, I think you were interviewed on that one.

Or Nate Latka, Nate and Latka had the SaaS one also back then. So yeah, dude, like all of these podcasts, they definitely inspired mine and changed my life, right? Because I can meet people that I wouldn't, uh, else elsewhere meet, right? Just giving high performers an excuse to hop on a call and chit-chat and Checks all of my boxes, uh, basically, uh, your podcast, why relaunch? Why stop the last one and why launch that one?

I guess it's a different audience. So the previous one was, well, probably similar to yourself. So part of the audience for Kind was founders. So I was just speaking to founders because it kind of puts you directly in front of your ICP. Um, in, and in this case it'll be similar, like And part of the reason that I am speaking to people in the legal and more sensitive areas is kind of for that same reason. It will definitely help with the networking. But I also think there's a lot of interesting stuff going on. Like you've got some lawyers that they're calling themselves now full-stack lawyers and they're going out and they're pulling in all these AI systems together and building out this huge infrastructure, which I just find fascinating. So I think that there's as well a lot for me to learn about the audience that I'm selling to, who I'm building for, how far you can push it. So sometimes we'll go to build a thing and you'll present it to a lawyer and they're like, well, I don't know, so you do some workflow building prompt library, whatever it is. No, I don't want that. I just want to click a button and for it to do the thing. I guess it really depends on who, like, what, what, how far along that spectrum you are in terms of how AI-pilled you are, I suppose. So I think it's interesting to speak to people along that whole, um, spectrum.

Yeah, to identify their pain points, right? It's like the greatest medium ever, just to ask them questions and take notes. Talking about that, what are their main pain points, your lawyer clients, right, that you work with? Um, you said some of them are full stack. I don't think that's most lawyers, right? I think, uh, most are still living in the Stone Age with like pen and paper. Like what pain do they face and how do you convince an actual pen and paper lawyer to switch to what you're building?

And, and that's the thing, right? And there's definitely a misconception from LinkedIn cuz the ones you see on LinkedIn are the full stack lawyers that are kind of like, nobody should be using any AI tools. You should be building all your own stuff, host your own model or open source it, and then build out your own RAG system. And like, 99% of lawyers are never ever gonna do that. I mean, fair play to the ones that do, like, that's awesome. And I would fully, like, I want to learn what they're doing and how they're thinking about it and how they're solving those problems, 100%. But most people aren't going to do that, despite what my LinkedIn feed tells me. Uh, there's a whole chunk that aren't even on LinkedIn. So some of our go-to-market is literally knocking on doors and just being like, hey, can we we have some of your time or doing in-person events. But sorry, it's a little bit of a tangent. Most of the problems seem to be in terms of context switching and not having enough hours in the day. So they'll start the day and open up their email and their calendar and look through everything that they've got to do and then get on some work in Word for a little bit and then switch back to their PMS system to log the time for that. And it's just all these kind of like micro switching. So we're trying to take away a lot of that context switching and just be like, well, you can just open Parachute, it's already sucked in your emails, it's prioritized it for you in terms of what you need to do today, your calendar is kind of right there. If you need to draft a response, you can one-click a button, it's drafted this thing out for you, and that's all then set in, you know, legal grounding and case law and legislation that they haven't then had to go off and and research, but with all the citations there so that they can verify it or click through to the original source so that they can see, like, verify that these things are correct. So I think it's more like death by a thousand cuts for lawyers at the moment.

Yeah. What are your main priorities for the rest of this year? What's your top 3 as a co-founder? As a co-founder, um, I don't think you're CEO, but whatever, I let you to head on to, right? Yeah. What are your top 3?

Um, so we're going to start dipping our toes into the US. I think there's, um, definitely a fairly large market there. Like, the cons— I think probably like an 80/20, the concentration will still be in Australia. There's a big, big pool of lawyers that we can serve there. Um, so I guess scaling out the infrastructure so that it can support multi-region, which is stuff I've done multiple times before. Um, then once we've raised, probably like bringing on a few more lawyers to sell for us. So we're definitely finding that it's more effective teaching lawyers to sell than it is salespeople law, and just inspires more confidence when they're actually in the room or on, on those demo calls because they thoroughly understand those pain points. Um, so that's 2, and then 3. Oh, where's my third? That's a good question. Might have to come back to you on the third.

How do you manage your, uh, engineers nowadays, right? Uh, and how do you recruit these 1000x engineers, right? Which I guess is the goal nowadays.

Yep, it's, uh Very interesting time. So we're a team of 3 engineers, including myself. I'm still very hands-on. We're definitely AI first. So when looking— like, I'm fairly fortunate and I have been in this game for a really, really long time. I think I started coding when I was 15, which is a really long time ago. So In that time, I have built up a pretty solid network of engineers that I can speak to and fall back on and bring in. So I've brought in two awesome engineers who both are all in on AI and like learning and sort of trying to, you know, if something can be done, figuring out how it can be made repeatable instead of, yeah, just like doing something from scratch every time. Just kind of really have that correct mentality in terms of how we scale it. Then for people that we don't know, so we've got an intern coming in, and that was an interesting— okay, how do you evaluate an intern that's kind of not got the experience? You can't necessarily reference check them. So we did a, like, a side-by-side pairing coding challenge but allowing them to use AI to build out something moderately complex. But rather than watching what the output was at the end, it's more saying, okay, what are they asking? What are they pushing back on? It's mostly like, what are they saying no to? Or are they just accepting everything that's got AI spitting out at them? Just to really evaluate more their critical thinking and how are we going to be able to guide this person to get to the correct result rather than just assuming what you're being told is correct.

What does the law firm look like in 15 years from now? Is it one owner managing an army of AI assistants and agents? What would that look like?

I feel like that's quite likely. Uh, maybe not your average— look, Big Law, I think, will still maybe not take that shape, but I can definitely see a lot of sole, solo operators going that way. And like a lot of our customers are people that were in big law that have now gone, you know what, I could probably peel off and do this myself. I could get a few agents together and like spin up a new law firm and run with it. I think probably a lot of less risky work will probably go to AI tools as well. So like lawyers may not be engaged for some of the less risky type of work. Because in some way, I guess a lot of legal work can be seen as insurance, and you want that seal of approval from a lawyer. So yeah, it probably depends on what the kind of risk appetite is of the person that's generating the document in the first place. But we're seeing it already, you know, like someone will go to ChatGPT or Gemini, they'll spin up a contract and then send it to their lawyer and be like, hey, I've already done the work for you, can you just say that this is okay and give it a tick of approval. And then the lawyer's like, where did you even get this from? This is wrong, that's wrong. And they would argue that it takes them more time to correct what's come out of this tool. So we do, we actually allow our lawyers to on-sell Parachute to their clients. So it's like, if they're going to be using an AI tool anyway, they might as well use one that is actually, that doesn't actually have all the legal case law and legislation. It's going to be grounded in some kind of legal framework so that when you're reviewing it, at least you've got a little bit of a head start rather than that it's come sort of out of an off-the-shelf AI.

Yeah, love it, dude. Pretty promising, right? And I saw a part of what you've raised, right? So very bullish on what you're building. Where can people find out more about you, Dave?

So for Parachute, uh, they can go to goparachute.ai, and then for me, I'm at daveburner.me.

There you go. That was Dave and Charles Cormier for another founder