Simon Rohrbach (Plain): The Designer-to-Founder Reality Check, and How AI Changes Everything

28:39Andy Budd:nobody needed in the first place and and i think that's a far off in the far bigger failure mode right for product development is you build the thing that nobody needed so i think that's our job ultimately as designers is to find the thing that people need absolutely the way i liken it is A lot of my friends have got kids and they find themselves saying the things that their parents used to say to them when they were kids that used to annoy them. But now they're on the other side of the equation. They're like, oh, I get it now. I get why that they were saying you should do X or Y or tidy your room or this, that or the other.

29:08Andy Budd:So I think there's a kind of a new perspective that you bring coming from that sort of business leadership role. Were there kind of one of the things I tend to find with operators that become leaders? Like if you're an engineer and you're a founder, every problem is an engineering problem. If you're a marketer and a founder, every problem is a marketing problem. Is there a tendency that when you come from a design and product background, like every solution becomes a product solution and you end up kind of like delving into this area that you love and finding more excuses for doing product stuff?

29:39Andy Budd:When actually, as a founder, you need to be looking at something else. You need to be looking at go to market strategy. You need to be focusing on building the business. You need to be focused on culture. but you're constantly drawn back to this thing that you're good at and makes you feel kind of successful and powerful and have fun yeah 100 um i think that you know probably continues like to be the biggest challenge in my in my day today um because i've done the hard 180 to towards go to market and and like uh sales and success and like building sales team and all these sort of things um so my day-to-day now is probably 90 those things and 10 product if even i don't think always remain that way remain that way but i think right now it's kind of what the company needs um and the thing i try and remind myself of is your job ultimately as ceo right is to work on the company's biggest problem and i find this a very kind of useful like mental stop gap for for kind of going like or mental check for kind of like in doing this thing right now that i'm being drawn to with the product uh am i working on the company's biggest problem and if the answer that is no then they probably shouldn't be working on it um and of course ultimately like in everything lives and dies with the product like if you don't get the product right then like good sales can't fix that um and and so yes everything ultimately kind of comes back to that but um that kind of absent flows i think as the company grows right like you'll have moments where like the product's in a really good spot, then actually, like, you know, all the teams are totally running in the right direction and, like, everything's just execution.

31:14And then it's time to, like, go and build sales, right? And then you might be in a time where, like, actually the product, like, needs to be, like, of reclarifying and re-adapting and shifting in the market. And, like, and so that you have to go and spend time over there again. But I think the, yeah, like, the big sort of, like, muscle, I think, to build as a founder is you have to like increase your tolerance for stuff that lives in spreadsheets and like processes that are nowhere in the product and things that are super scrappy, very manual, but they get the job done. I think that ultimately has to kind of be your MO is to do those things first and then multi-seater the things that are working.

31:54You can build them in the product. You can build tech around them and like all these sort of things, right? But that's not how you start because code is hard to change. you know manual process or not so I think it's a good sentimental model

32:09Andy Budd:absolutely I'm curious like again back in the early days like when did you really truly feel you were onto something like there's a lot of conversation on product market fit how you know when you're you've reached product market fit so when did you suddenly realize ah we're seeing demand things are growing we're on to something um it's sort of um there was a point where um we started we started getting people like signing up for the product um and um and talking to us that were companies that we'd never thought we'd have the privilege of ever being able to talk to. And there were companies that we had looked up to.

32:57Like when we started the company, we were like, you know, we're like, okay, like if we really make it one day, maybe we'll be lucky enough to like, forget even work with the company, but just meet some of the people there and get to learn from them. And suddenly a few of these companies actually express interest in what we're doing. We're like, hey, like we really like your approach. sure we like what you're doing um we're moving from such and such platform we'd love to like do a trial um and i think that was kind of the first one was like hold on a second like this is like this is now exceeding our expectations that we had of ourselves you have this kind of oftentimes weird duality as a founder where uh or a sort of cognitive dissonance between you're starting this thing because you think it can be really big um and your vision is to build a really big company but that's totally divorced from like what do i think we're going to be next month um and and like instead of like what's the level of you know like you almost you're almost like short-term pessimist long-term optimist at all times and you can live in both worlds at the same time and and it was yeah that's at a point where these companies started inbounding us and we're like okay, we'd love to do a trial.

34:11This looks really, really cool. And almost like started taking the product out of our hands, despite its imperfections and despite all the things they didn't get to you. And they were willing to look past that because there's someone in beyond that. That's really when I felt like, okay, this could really go somewhere.

34:25Andy Budd:So you're really starting to feel this sort of market pull. It's not you pushing anymore. It's like you're starting to see brands that you really admire, that you've always wanted to work with, kind of start to have those conversations. before you got to that market pull like how did you get your first customers like that's a real challenge at the moment i think like channels are saturated you know what might have worked on on twitter or or kind of instagram five six seven eight years ago isn't working now so what was your initial go-to-market strategy like and what was the thing that kind of really clicked when you're like hey we're we're talking about things in the right way or we found the right channel that works yeah um the best way to sum it up is is that like the way we got our first customer was never how we thought we'd get our first customer um so you know we had this really elaborate plan for like okay we're gonna start like you know outbounding all these companies and like you know maybe we'll be able to launch in like a month's time and and like you know let's work towards that and here's all the great things we have to have in place like a really nice website so we can make a big splash and like you know really great onboarding experience and like All that sort of stuff.

35:31Classic kind of like, I think, designer mistake of like, everything has to be just right until we can launch. And suddenly this colleague of ours from Deliveroo, like he left Deliveroo and he started a side project with a couple of friends of his. And I remember what it was. They were building like a platform that allowed you to send out voucher codes for participants in user research. oftentimes in easy research right you incentivize people with like a voucher of amazon voucher or something like that oftentimes it's a really big pain to like just organize the expense and also stuff to the build up arenas platform that like essentially like point and click and go like i

36:10Andy Budd:want to send the voucher this person this person they they ultimate the whole process and that started getting some traction and so they're starting to get some some inbouts from the customers and then some emails and they knew that we're building plane um so suddenly i get this random mozza message uh like thursday afternoon or something and um actually graham was the name like graham kind of goes like hey like um can we use you guys we need a custom support tool and i was just like what like no i guess yeah sure um and um immediately everything changed like the launch no longer happened we're like okay like let's get a call going now and we'll get you set up and like we just like yolo'd the whole onboarding and like it was completely manual completely broken.

36:52We got them up and running within like an hour. Turns out we didn't need the nice onboarding process or the nice website. We just needed people around us to know that we're up to this thing and they were building this thing that could help them solve this problem. And so it was this completely unexpected just being pulled into the market by friends of ours that I'm still really grateful for because I think without that, we probably would have still been at this like two more months and like, you know, built a really nice website first. For me, it's a good lesson of just like some other thing you need, just like the forcing mechanism to pull you out of that mode and make it live now, despite all its flaws.

37:31Andy Budd:Absolutely. In my book, I talk about kind of this quote from Paul Graham that says, at the start, you don't need to get the word out, you need to get the word in. And by that, he means that so many of your early customers are going to come from your network, probably. I think this is one of the reasons why a lot of VCs are really interested in founders who understand the problem space really well or are really connected to other people that might want to use the product or, you know, in terms of hiring as well, being connected to really amazing talent. Like those first, you know, 10 customers or 100 customers or if it's B2C or 1 ,000 customers might be coming from your direct network and friends of friends.

38:06Andy Budd:So that's really important. Beyond that, like was go-to-market easy? I'm just thinking like companies like Intercom, they had a really big play when it came to content strategy. Like what were the early motions that were working for you and playing? Yeah, I think a couple of things. I think the first thing I think is it's just to show velocity because I think in a very crowded market, right, like people don't buy the current state of the product, they buy what it's gonna be and they're making fundamentally a bet on your team and so the thing that like really helped us which is like every week posting something the change log and kind of like here's what's new and making some noise about it that was kind of the first thing I think the second thing was and I hesitate to recommend this because I think it's it can be a bit of a trap but we were designers so we were like okay how can we make this look and feel very nice from a marketing perspective and actually we started getting lots of love for the way we've done our website and all these other things.

39:08So despite what I said earlier on, it actually getting a first customer inbound pulled us out of that mode of having a really nice website. Later on, that actually really helped us because it was us playing to our strengths and it was us trying to convey the quality of the product with the quality of our marketing and our positioning. And that resonated with people that were like us, who valued nicely built tools and well design products which is a lot of dev tools um and a lot of like tools that are for builders so we definitely sort of tried and sort of like took a bit of inspiration from like the linear playbook almost of um of trying to build this sort of perception of this is a really high quality product that really worked um and it got us a whole bunch of customers because our website started being shared around and lots of stuff again i think there's a trap there because that's not always applicable in every single market like you know i think as your customer base grows not everyone cares about this but you can get either um to start oh no i was just gonna say i was

40:04Andy Budd:curious like how much you think the brand of the name played in i spoke to sam stevenson recently from granola who talked about how the name granola was almost an accident but in a weird kind of way there's something really nice simple clean about the name that kind of is really really attractive i think the same with plane it's really there's something you know really just it feels natural And so how did the name come about? And like, could you have, you know, become as big as you were successful if you were, if you were kind of like support pro, you know, you know, dot com or something instead?

40:45Yeah, like, I think naming was a bit of an obsession of ours. So we actually started the company as Juniper, like Juniper Berry, right? And like, we just throw out a really nice ring to it and sort of went for that first. Turns out there's a very big company called Juniper Networks. And they have a lot of lawyers with like a dedicated section on their website to the trademark. And so we're like, okay, that's maybe not such a good idea. but went through a bunch of names and ultimately landed on play. And I think because we sort of felt like there was something really nice to like having a bit of a blank canvas and a word you can make yours, a word that many other people probably would not pick.

41:25And actually, if you do it right, you can lean into the meaning of that word. And in our case, we felt very strongly in a field that still to this day and I say this to everyone who joins. a lot of customer support software feels feels like filling in your tax return it's not it does not spark joy when you're a support team or someone who works in support you use a tool like this eight hours a day and so every interaction really matters and over time a lot of these tools have become full of like all this fluff and all these clicks and like all this stuff that just feels like you're waiting through mud and all of that is just to talk to your customers which is like the single most important thing your company can possibly ever do.

42:05And so playing in that kind of landscape, you know, we call it CS without a BS. It's customer support without any of the fluff and any of the BS there. And we sort of really wanted to lean into that. And I think the name playing sort of speaks to that really nicely. And that is plain and simple. It does really well. And you can use it forever. like you know you can use however you want you can it's really flexible it's really adaptable but it's just plain and so yes 100 i think the name is a big thing and i think it's also yeah it's a bit like i don't know like you know buying a property right you can change many things about it but the one thing you can't change is the location and the name is is like that it's like you can't i mean you can change it but it's expensive i was going to ask you actually

42:56Andy Budd:in terms of the location, with such a simple name, how difficult was it to get the domain name? It was actually reasonably straightforward. We got plane.co first because that was available for sale and not that expensive. Plane.com was listed for sale, so I just contacted them and negotiated the price down. I got this really great advice, which is firstly, don't contact them from your main company email because then immediately the price goes up. Second, name your price and then walk away. It's the only way. And so I named the price and I walked away and the person that we bought it from negotiated themselves down and sent me several emails like, you know, it's this and then actually I would go lower.

43:42How about that? How about that? How about that? Until they met the price um and then we bought it so it was um feels like a sort of a stupid investment up front but then if you think about it it's like it's the cheapest it will ever be because you have to assume that like you'll be successful and if you are successful someone's gonna sit on that domain name knowing that you exist um and waiting for you to raise some more funding and then go like great like it's now several million pounds um and and you don't want that so actually in proportionality The amount of funding we had at the time was actually one of the cheapest purchases we've ever made.

44:18Andy Budd:That's amazing because you could have quite easily said, yeah, it was a couple of million pounds and it was a really harsh negotiation. So I think the value you've got from that domain name is huge. And I think having a really strong domain name that is searchable, that's findable, that's memorable, that isn't kind of really complicated. You see so many domain names where the way it's spelled is very different from how you vocalize it and you can't ever find those companies. companies so i think that's that was a a really good purchase yeah we got it for like 40k usd or something like that in the end um that's that's good from what i'm being told not bad for like a thing like this yeah um one thing i haven't talked to you about because you said that you said that fundraising basically you'd done a year at um a vc fund index they were your your first investors did you actually formally have to go out did you do the kind of dog and pony show did you go and speak to 40 50 vc funds did you get lots of rejections and door slams or did you just go to index say hey this is what i'm building next and they wrote you a check on the spot um i think maybe something in between like you know it's one of these things where um when you join a fund um to be an exact residence or some some funds also have an entrepreneurial residence right like the success the success success definition of an engagement like this is that either you join a company uh in the portfolio or you start a company um and if you start a company the idea is to kind of like hey like you'll talk to them about it first there's no obligation there or anything like that you know nobody has to invest or whatever like you have really bad ideas that that's like you know not not the um not the goal it's more just like that's kind of like part of what makes this can make this so beneficial and such a great experience it's definitely kind of conversation we can be like hey i'm starting this thing what do you think and actually what's really nice is like you can actually you have all these amazing people around you um that can help you stress test the idea uh and kind of go like you know here's like what does make sense what does not make sense how would it make sense like um here's my what might be a bad idea etc so um It kind of like makes that initial stage actually way more kind of like way more beneficial to like the thing that you ultimately kind of like building.

46:42So we did go out and like, you know, meet lots of investors, but it was more just like after we kind of knew, okay, like we'll probably, we'll do this with Index. And, you know, they're excited about this and we are excited about this. And then it's more just about getting other investors to join the round. So there was a bit there and it still took us like, you know, probably a month or two to kind of get everything fully wrapped. But on the whole, we definitely am very thankful for this. Like we had probably an easier experience getting started than many other companies just because we had that kind of relationship.

47:15Andy Budd:I mean, this is a much more common thing in the US. I see a lot of times in the US, a founder or senior executive will leave a company that that investor has backed. they will come in as an entrepreneur in residence or executive residence for a year they maybe start working on their next project and then they've almost got like a you know not guaranteed but they've got a really good in for that that round i'm curious the reason i was asking is like if you were talking to a young designer now that was thinking of leaving their job and raising funding like what advice would you give them how would you help them navigate through that process yeah i think the first thing i'd say is like spend time on the business not on the product um like the product will come easy to you right like it's literally your job and literally like we do every single day um that's not why this will fail um if you have that skill set like the reason this will fail is because you know you you're you're picking um a really cool product idea in a really bad market um i think that that's the far more common failure mode so my biggest piece of advice would be really make sure that like the thing you're going after isn't a market that can support a very large public trader company because if you're swimming upstream against the market that just never will be good um like and there's many markets like this right where i don't know like there's you know certain verticals where it's just like you look at it and go like it's just hard to make money in a space like this um like you you see for example um um calendar applications isn't an interesting one where like you can have you can build such a great product there um like you can have so much fun building like the best possible calendar app ever um it's also a category where it's very hard to make money because where you're swimming upstream upstream against this google calendar which is free uh or like a bundled um as part of like your google workspace description um and so like there's there's a bunch of categories like that where yes you might have a breakout success um but there's also a history of like many many companies having tried um and not really having been able to make it work as like a standalone um thing and so like it's not to say you can never turn into a great business but it's just it's much harder so i would say like spend time on that and really make sure that like you're going after a market that can support a very very large company uh and where there's the money to support a very large company, where transactions are big and these sorts of things.

49:43So really go deep there. I think the second thing I'd probably say is really make sure that the thing that you're picking, the thing that you're going after, is the thing you can see yourself spending a decade on. And it sounds kind of extreme, but I think it really has to be that. This can't be a thing in the moment where, you know, sort of it's hot right now, but like in years time, you're going to lose interest. For me and for Matt, for both of us, this was always like customer support to this day continues to be like a thing we very, very deeply, like have a very, very strong conviction in because we think fundamentally it's about fairness like in a company.

50:32It's like, why are you giving the people who are you linked to your customers and work so hard trying to fix things when they go wrong, why are you giving them the worst tooling, the worst equipment, the lowest budget, the lowest share of voice in the company, and ideally outsourced so you never have to talk to them ever again? It's completely upside down. It makes no sense. And so if we can build better tooling for a space like this, we can actually make someone's workday just that little bit better. And that alone is massively worth it. And it has to be something that we deeply believe. It has to resonate with you deeply in what kind of world you believe in so that in year five, six, seven, eight, you can be an all-hands in the company and inspire the company and rally the company around why this really matters.

51:13Case in point, this is year five for us. I've moved to SF together with my wife and my dog to open up the office here. I've spent most of my life in London, right? It has to be the kind of thing that you're prepared to do these really big things for. And if it doesn't meet that test, it's probably not the right idea.

51:30Andy Budd:I was actually going to ask you about the SF move. Like, was it difficult deciding to, I guess this came off an expansion in North America. Obviously, when people expand, there's a real desire for the leadership to be there, to be, you know, seen and be connecting with customers, et cetera, et cetera. So was this a tough decision or was this always going to be inevitable with success? um i think it's like it's one of these things where sort of as your horizon expands um and as you kind of go hey we're starting to get like you know a lot of inbound especially from from the states and actually case in point one of our first bank customers was from the u.s um and since they won the law of our revenue like majority of revenue was always from from the u.s um you kind of go like hey we should probably be where our customers are um and and then actually becomes like very for me being a very logical decision which is my job ultimately is to improve the odds of success for the company um right and um there are many things i can do in my day that frankly don't move the needle on that um like i can go and like polish a feature doesn't really affect the directory of the company um being where your customers are and being or especially right now is kind of the epicenter of software for a large part of the world still at least in tech right like being there um and and like building a team here and having exposure to that and being next to your customers many of our customers literally stand the road i think that alone improves the odds of success for the company by one or two percentage points and that is greater than any other thing i can do um in my day my week in my month And so I think from that perspective, and it just becomes very obvious, obviously that's the thing that you'll do.

53:21And so, yeah, it was kind of like, was it hard? Absolutely. It's like, it's in a different culture. You are learning a new way of communicating, like what you do and operating a new environment where you don't have any of the network, et cetera. And the time zone shift is kind of rough. Like your AI is behind London, right? So my mornings are like insane. and that's hard, but I absolutely believe it's worth it.

53:49Andy Budd:I'm getting a sense from your social media, from LinkedIn, that you're really, really enjoying being there. It feels like you say you're in the epicenter of something, and I can just tell from your demeanor that it's really good fun. In terms of sort of philosophically, I mean, again, a lot of European companies will inevitably, if they're successful, move to the US because it's just a huge market with a single language or a couple of languages. Some people, they just move their sales out to the US and keep product back home. Some people, they want to go to the Valley, to the Bay Area, because there's so much engineering talent.

54:30Andy Budd:But then it's also a bit of an arms race with everybody else there. What's your philosophy at the moment? Is it just a sales team? Are you replicating all of the functions out there? How are you pulling this together? it yeah um big piece of advice we've got no leon from one of our investors what was it's really important to cluster um and they kind of go like hey like where do we want to headquarter each function so right now we're headquartering go to market here in sf um that is not to say and and like we're headquartering uh epd engineering product design in europe in london um and like um we have people all over europe so it's kind of it's quite distributed that is not to say that this is the only place where you have those functions.

55:13We're now hiring a first engineer here. I think that's going to be really important to also support the team here. We're going to have more go-to-market in Europe. My goal really is to have almost three HQs. It's to have London, Europe, Remote, and NSF and to make sure that we have functions that are strongly located in each of those. because I think it's sort of, for me, it's kind of the new operating model of many, many companies where you can have an in-office presence and that's really useful as like a hub for your customers, your community, you know, the people that you're trying to like do things with.

55:52And at the same time, you can also still have access to like the very best talent in the world by like opening yourself up to a remote. So I think both those things are possible at the same time.

56:02Andy Budd:I mean, that's exactly the kind of the approach I would recommend. So it's great to hear that that's sort of what you're doing. So brilliant. Sort of last question or a couple of questions. Like obviously, AI is huge at the moment. There's loads of opportunity in the support space. I'm curious, how is the product evolving in the face of AI? And then my second question to that is how are your internal practices, particularly around design and engineering, evolving? Yeah, I'll take the second one first. I think everyone in our company now codes, whether they write the lines of code themselves. And we've always kind of had this to some degree.

56:43Like we've always hired designers that are technical and all of that. It's something I very deeply believe in. But now, like we've really taken it to like a new level. Like every designer, we don't do mocks and wireframes anymore. To be fair, we never really have done wireframes or anything like that. But like we don't do like prototypes. We open up Cursor or like Claude or like anything else, right? And we kind of go like, let's make a prototype of this UI and how we want it to work. And it's available in the browser. We can all click around with it and reason about it. And certainly within like a couple of minutes, like you have something that like you can share around, you can give to customers and they can actually validate something with.

57:24So we do this all the time now. And I think that's become like a really big boost. Obviously, the entire engineering team use AI every single day. many, many, like in every single line of code almost at this point. So that's become a big accelerator for us as well. So there, I think, we're really, really pushing internally a lot. And that also extends to all internal processes and sort of like automating things that like previously, you know, were hard to automate. So we do this a ton. On the first part of the question, how is the product changing in the face of AI? I think a couple of things have shifted for us over like the last like, you know, sort of six, 12 months.

58:02um they're really doubling down on now firstly what's happening is that like software is becoming like cheaper and easier to build um and that suddenly means that for like you know straightforward use cases it's pretty straightforward now to actually like vibe code your own thing um that does most of the thing that you previously bought a sass tool for um and so that's what's the value that like a platform can offer you in that in that scenario well okay like you probably don't that like own the constant maintenance and like all of the bugs and like all that stuff that becomes a really big distraction but i think even beyond that like i think it just basically means that like a lot of like sas platforms are now turning into infrastructure i think the good ones in my opinion will and so we are in an unusual position here and like we started the company api first we started the company's infrastructure and suddenly the infrastructure we've built over the last five years is now actually really coming to the fore and so what we're really doubling down on is giving people the tools to build their own support system.

59:05We are no longer a support system. We are a system for building your support system. We're really excited about that. We're giving people the flexibility, the extensibility to build whatever it is that they need to support their business and to talk to their customers. Almost give them Lego blocks that they can assemble themselves because now it's way, way easier to do. We want to bring the same level of flexibility that engineers today have with live coding. We want to bring that to the support space. I think that's a really, really fundamental shift. And I think the second thing, to be honest, I think that's going to happen is you have a lot of like AI agent companies right now, especially in the support space, that you can point your support to, right?

59:44You can kind of be like, hey, like, do solve this ticket. Talk to this customer. Give them a response. At the same time, you have to operate from a position of assuming that, you know, all the foundational models that are out there, like CharterBT, Claude, et cetera, get an order of magnitude better every three or six months. And if they do, and you as a company are not training your models, what's the mode that you actually have when these models get so much better? We're not that far from being able to point any of the foundation models to your support and go like, at Chachapete, at Claude, do support.

1:00:26That world is not that far away. and very few companies in the space have the resources to be able to train their own models so what's the value that a company like us can provide in this this world well we can give you the building blocks to like to be able to like orchestrate all these different things all these different agents that might be using all these different like foundation models um in a way we all play together and you can actually build a system for talking to your customers a system that talks to your customers for you um and i think that's very much the world that we are embracing is one where I think that the future is very multi-agent.

1:00:58I think in the future you'll have a platform where you orchestrate lots and lots of different AI agents next to lots of different human agents. And we want to build the orchestration layer for all of that. So it's a really exciting time to be in a space. It feels to me a bit like, well, I'm old enough to remember when everything first came online and it feels a bit like that, you know, sort of like everyone suddenly had a website and was like, now we're online. We have a website. You can buy from us online. And it feels a bit like that. So it's a really fun time to be in the space.

1:01:30Andy Budd:Yeah, absolutely. I think there's so much renewed energy at the moment, so much opportunity. I think you're in a brilliant space. I can see the energy and enthusiasm there. So look, I can't wait to see what the next sort of five years of plane will be. But I'm sure it's going to be amazing. Thank you so much. If people want to follow you if they want to follow your journey if you're if there's a a designer out there that's kind of harboring the idea of being a founder if there are founders out there that really love the kind of attitude that you've you've brought to the conversation where can they follow you yeah sure so send me an email simon at plane.com very happy to uh help chat in whatever way i can um follow us um playing support on linkedin uh or x um and um then me sam roebak on uh on linkedin or Twitter.

1:02:19Brilliant.

1:02:19Andy Budd:Well, look, Simon, thank you so much for joining me. It's been great having you on the show. Brilliant. Thank you so much for having me. Really appreciate it. Great conversation. And thanks to everyone else who's listened. Thanks for tuning into the Design VC. If you enjoyed this episode, please subscribe, leave a review, share it with someone you know who cares about the intersection of design, startups and venture. And I've been Andy Budd and I'll see you next time. Goodbye.