Des Traynor On How His Team Raised $241 Million To Connect You With Your Customers At The Best Possible Time

Des Traynor is the cofounder of Intercom which creates modern Customer Service software that redefines how businesses support their customers. The company has raised over $241 million from top tier investors such as Kleiner Perkins, Bessemer Venture Partners, or Index Ventures to name a few.

In this episode, you will learn:

• The types of startup investments he is making
• The future of business on the internet
• Des Traynor’s top advice when launching your own business

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About Des Traynor:

Des Traynor is a Co-founder and the Chief Strategy Officer of Intercom and sits on Intercom’s board of directors. Des has led many teams within the company, including Product, Marketing, Customer Support, and Content, and has been directly responsible for building out even more functions within Intercom as well. Today, Des oversees Intercom’s R&D team, based in the Dublin and London offices.

Before being part of Intercom’s founding team, he was a UX consultant, a university lecturer in computer science, and also a Ph.D. researcher studying how to improve the quality of computer science education. Des also previously co-founded Exceptional.

Des is an author and speaker on the topics of starting a startup, scaling a business, creating a product strategy and more. He shares his ideas and expertise in books, podcasts, and conference presentations. He also invests in many startups, some of which include Stripe, Miro, Notion, and Hopin.

Connect with Des Traynor:

• Crunchbase
• LinkedIn
• Facebook
• Twitter

Read the Full Transcription of the Interview:

Alejandro: All righty hello everyone and welcome to the deal maker show. So today. We have a very exciting founder. You know a founder that not only you know he’s a founder himself but also he has invested in tons of startups. So you know he’s built a rocket ship. You know I’m actually a very happy customer you know of their of their company. And I think that you’re all going to find his story very inspiring. So I guess without fartherdo. Let’s welcome. Our guest today Des Traynor:k trainer welcome to the show. So originally from Ireland you know you haven’t moved much so give us a little of how walk through memory lane. How was life growing up there in Dublin.

Des Traynor: Thank you very much ajandro.

Des Traynor: I grew up in dolan in the 1980 s was pretty much a bad time economically for the country before us joining the european union and getting all those benefits or whatever so jobs are hard to come by I was the youngest of 7 all my brothers emigrated to the United States um and yeah I just. Probably had a typical normal Dublin 1980 s childhood like you know playing soccer and like you know I think I got my first computer in like 88 it was a commodore vic twenty and then I upgraded like 91 or 92 to an amiga five hundred kind of always interested in tinkering with computers. Um. Really I I it all kicked off when I went to actual university in two Thousand Sorry ninety ninety nine I went I enrolled to study computer science and software engineering and that was where um, that was where you know I think I started to make irreversible you know decisions in life one of which was you know making a career out of computing and yeah, so that was kind of like. That would bring you true. Most of my childhood. It was mostly misspent. Ah bad attempts at being a musician bad attempt at being a soccer player but what it turned around to computers I felt I was at some sort of knock of making things work or getting things to happen.

Alejandro: And what where do you think that interest you know for computers came from.

Des Traynor: I it was entirely fueled to to in my opinion by like I had a friend who was actually from l a I used to hang in his house all the time and he was. He had a commodore 508 amega 500 and we used to just play computer games a real typical misspent youth stuff like. But he got this device called an action replay which is he could plug it in to the side of the computer and it would literally let you edit what’s in memory for the computer and the more I tinkered with that the more I felt I had I was growing a kind of innate understanding of how computers work we started like cheating in computer games so we could like no not online because there was no internet back then. But like we were able to like reprogram memory to say no I don’t have 2 lives left I have 20 lives left and all that sort of stuff that was like where like the sort of interest started where whenever we got a new game much as we were trying to play it at least 51% of my brain was trying to work out. How am I going to cheat this thing like what are the ways in which I need to like plant tracers in memory and see what. If my ammunition goes down or up. How do I rewrite it so it never runs out and all this sort of stuff and um and yeah, that was like that was where it started and then it was really only like in 99 when I enrolled and actually studied you know proper how computers actually work I realized then what we were actually doing versus what I thought we were doing. But yeah, did that was what kind of grew the interest initially.

Alejandro: And what was the um because obviously you know when when you were right after school I mean you really took seriously investigating web 3 but web do actually ah and you know and we have the flickers of the world and and so forth. But but.

Des Traynor: Um, yeah.

Alejandro: What were you? What were you like discovering as you were investigating what kind of interest was say peaking you know from that investigation.

Des Traynor: Yeah I mean she’s web 2 is such a rich environment like like I know I’ll just cant say in comparison a web tree where I still look I’m work at what the hell’s going on to be totally blunt about it. Um, web two like it felt like overnight technologies like Ajax Emerge Javascript got taken seriously then you’d like. Better developer frameworks like rails emerge after and I think in general what? what was what was happening very clearly in front of our eyes like you get to gmail be an extreme example or like Google Maps I don’t like if you remember to launch Google maps but the whole like slippery foot floor effect where you could drag a map and throw it and it would slide and all that sort of stuff. All of that just to me what it looked like was a new like model of computing where previously we had been taught that ui meant buttons text inputs dropdown fields those sort of very ah okay, cancel dialogues like those sort of very primitive pieces of product user interface um with web to. It was all thrown aside and it was like Des Traynor:igned the best possible experience and you mentioned Flickr like ah order tools like delicious were out at the time gmail was it was launched or in around his time as well. What we kind of realized was like wow the best interface is going to win. So. While I was at the time I was actually attempting a ph d in in my university and but I was way more interested in what was happening on a daily basis I was a refreshing like dig.com some of listeners will remember it or Reddit ah back then was mostly tech focuseded.

Des Traynor:  Alls I Really cared about was like what’s new in technology and every utter date.. There seems to be some new cool. Ah you know, technology emerged like doublebbled B or two eighty North or any of these things just kept getting released and like man it was. It was an incredible time for tech and eventually I just got more obsessed with that and I then I. Was even close to being interested in the Ph D So I started writing about it reading about learning how to program in it etc and then ultimately transitioned into a career like working on Usability initially product Des Traynor:ign and then ultimately product management and that was it was all prompted by just sort of. The break True tech of that Era. It was just incredible.

Alejandro: Do you think that the that interest also that you develop for blogging has helped you when it comes to storytelling. You know whether that is that they you know be figuring out how to package and position something for customers or figuring out how to raise capital from investors. How do you think that has helped you.

Des Traynor: I think like I’ve always had a keen interest in I’ve always been like an avid reader of like fiction to be clear like I mean I read read lots of things but I mean I think it’s people underestimate the value of reading fiction and reading good stories. Um, like you know it’s we all like to say that we sit at home and read like you know. Ph d dissertations but like in practice if you want to be if you want to learn like good writing does a lot. You’ll learn from like Don Brown’s the da vinci code. There’s a reason why it’s old so much it to hit. You know you know like there’s like there’s a lot to be said about just great engaging writing that people miss. So I I generally have always read a lot and I’ve always like being a quite of m. Like ah a matter reader like trying to like when I read something I also think about why is this so engaging and I think oh it’s because every paragraph leads to next row because oh it keeps confusing me and it keeps it gives me like a lack of closure and I feel like I need to go back. So I always think about that whenever I observe good writing. Ah. At the time I read a lot of ah Paul Graham’s articles obviously ah Paul Graham Dot Com Joel Spolsky 3 1 of the biggest influences on my writing ah Joe on softwaret.com was his website. It was like um just you know, just ah, both very comical and very um, very have to say just informative writer. It’s probably the style I most try to copy ah Butch as a few as Jeff Outwoods coding horror would be in there as well daring fireball by John Gruber they were these were all the big early influences that was kind of like who I was trying to be when I was but oh sorry I have to say Jason freeed and 37 signals as well. Um, but that was like who I was trying to be when I started blogging and I think.

Des Traynor: You know to your question of like did it help? Yes I’ve I’ve like no doubt it’s been at least at least half of my career I can attribute back even the fact of the reason I met own the Ceo our Ceo at intercom is actually down to the fact that I was writing. And I was writing stuff that he agreed with or whatever you know and and in fact that I even know he knew who he was was because he was writing too. So I really think you can’t ah you really really can’t overstate how important that is ah as a skill as for intercom and how it most directly helped I think. Our blog was is and has always been quite ah quite popular and I wrote the first I guess 93 of the first hundred blog posts these days I’m mostly just doing our podcasts. But I you know I think you can build a brand true like ah like you know. Good expression of interesting ideas that are relevant to your product so in the early days intercom we wanted to attract people who were startups who wanted to talk to their customers and wanted to grow a user base so we wrote about startups growing user bases talking to customers customer communication customer support and we grew. Just a lot of popularity and like us being known as a go to place to read all that sort of stuff I think over the years then we translated into like events we held world tours. We sold out like you know like you know, ah reasonably large venues in San Francisco and Dublin where people come along and basically see like a live performance of the blog in a sense people like.

Des Traynor: All all folks across intercom would present different ideas topics talks. We do like live firesiDes Traynor:, etc and I think yeah I I think the skill of content and obviously a lot of this is going to be open air in with the advent of Gp which we can talk about if you want but um I think that the content has been a massive party inter comess sort of. Founding story and brand and and I put a lot of that down to the time invested in writing by not just me but like I was definitely one of the folks who probably had it more assigned to as a job earlier.

Alejandro: So Then let’s talk about intercom so you know you actually were developing software. Ah and you know when when when you were doing that you know, really the conception of um of intercom came to Play. So. So Tell us you know what was that process of going from ideation to incubation and to launching

Des Traynor: So we actually we built you know our model at the time was something akin to like agency that wants to be software startups so you build stuff for other people and you make profit and instead of banking that profit or like you know, taking the time off you used a. Spare salaried time to build your own ideas. We built quite a few the before intercom the most successful thing we had was a ruby on rails developer tool called exceptional and ah I think. 1 of the things we were keen to do was you know grow exceptional like anyone tries to grow a software startup and to do that we wanted to talk to our customers and and like learn from them and. The the tool stack at the time to do that was just awful. It was an export of your database into like a campaign monitor or a Mailchimp where you’d compose your email send it out and if you’re looking you get all your replies back straight into your personal inbox which is like a really really messy. Messy way to em to do this and. If. There’s 1 thing you learn in usability it’s that 1 thing well something’s hard people just don’t do it. It’s not that they do it last they just they just turn off that right? like awareness of that so I was you know, um, at the time I remember talking to own ah on he was saying like.

Des Traynor: We know if we if we could talk to customers inside our product. It will be a more effective way. We we built out this widget effectively that sat inside the thing that posted little messages and um the messages would be things like hey like sorry we were sorry we had some downtime last week or whatever.

Des Traynor: But very quickly. It felt like a much more direct connection done to convoluted workflow and I was going through to do like our like you our meet the customers blog posts or whatever I was writing when I was talking to customers and um and I just I was obsessed with this idea that like talking to your customers is really important thing that every. Everyone does at the time as an example, we talked with this before but like we um, we worked out of a coffee shop and we were witnessing a guy called Colin Harman built his own coffee empire three f e dot com there and he was doing it but like 1 customer at a time. Great strong relationships. You know, like building people remembering his regular customers encouraging him to return. There’s no. Online way to do that. There was no way to like do like actual like you know proper like customer loyalty and retention online. There’s no way to build relationships with your customers online and then so we we knew it was really important to do but the tooling wasn’t there separately. We had this thing that you talk to your customers when you’re in your product and we thought like if you put the 2 of these things together. Like big problem space obvious solution. We um, we rolled out like I think um, a few different versions of an insider old product before we before I remember own was at a conference in like.

Des Traynor:  10 I think in Atlanta or maybe in in Jacksonville said like I think the best thing to do here is to like actually go all in on this idea and you know that wasn’t as straightforward as it sounds. We had a consultancy we had to finish up with clients etc. But we yeah we did it and that was um. That was how intercom was born effectively

Alejandro: Very cool. So what? what were the um, the early days of intercom like.

Des Traynor: Um, ah, brilliant like I mean like they were very stressful like you know 16 houra days six day weeks or whatever but like ah it was a very responsive time in that everything you did either worked or didn’t work and you knew what in minutes if you know what I mean like so um. Like we’d go from like an idea for a feature to the feature being live within a day or two days or three days and by day four you’d have a shit out of customer feedback. You’d be parsing true on and every customer we talked to like the calls always began I remember me and o and jumped on a call with a guy called Gareth Demon who had a product called sifter. It was a.

Alejandro: That’s amazing.

Des Traynor: Take a tracker an issue tracker unlike we jumped on. We had like 4 questions we wanted to ask him about his usage of intercom I think we were like 40 minutes into the call before he stopped talking about how great this thing was and and was just like he was telling us all to like you know ways he was using it and. We realized we had really tapped into this idea of a direct line between the people who build a product and the people who used a product like we had effectively created that idea of making internet internet business personal which was and is our mission. Um, and so like a lot of the time like for me the early days was like I was you know effectively doing customer support until we yeah we had our think. 6 or 7 tyre was a guy who started doing support first. Um and like it was like just learning about what people are using us for getting features built like expanding on the idea. Um, you know you don’t like you don’t know what it’s going to look like at the end. Especially. Alls we really had was kind of an abstract idea of connecting businesses and customerss like at the time we weren’t sure like will this end up being a help Des Traynor:k will this end up being a marketing tool will this end up. You know we we weren’t even thinking in that rich sort of way alls really new was it was cool to have a direct line to your customer inside your product and ah. And that’s what we were working on most was just this idea of like knowing who the customer was and letting the customer know who they’re talking to and then how can we make that as rich an experience as possible and that was genuinely like what I am what we what we are working on and most days was either building feature shipping features explaining features talking to customers.

Des Traynor: And then like sort of like unscalable shit. We used to do like I used to like run webinars I mean I a laugh neting every week I do a live webinar for an hour um to like sometimes bo we just be talked to 4 people like 4 people would log on and I’d give them a big a to z soup to nuts pitch of intercom.

Des Traynor: And then tri of them would sign up a morning would quit or whatever but like that was how we are growing a user base I often laugh now because like whenever like a common you know Podcasty question get is how did intercom get its first hundred users. Whatever. And I always tell people well yeah and we we we mail the tales of people I used to like 1 of my job is like to literally email customers 1 by 1 with like examples of how intercom would look if they use it in their product. What I could do for them and like you know how that sort of um like cold calling type mail works like yeah 1 in 5 you get a response I was. Because I was handcrafting them and making them really specific I think I was I was doing better on done an automation tool and I was getting actual replies. So I was learning and crafting and the responses along the way but like the amount of like manual effort we put in early on to just getting the groundswell up and running was pretty high and I often laugh when I talk to like. You know, founders today who are like cool is there any way to automate all that on like I don’t know if you want to I think it’s actually valuable to try and like the webinar got really good because I had to do it 52 times in a row you know like like you you adapt you tweak you realize what conffuses people. What excites people. Just like the to outpa emails I was writing that every single time you see something it works like you you you refine and polish and by the time by the time you get to the end. You really have a good insight as to how to get attention. So I think it’s not just you know.

Des Traynor: You’re getting better along with your messaging and your position and getting better and I just don’t think there’s a good way to sort of to automate that like I think you actually want to be going to the gym as it wear that often. Not just for like not just for the outcome. But for all the exercise you do along the way you know.

Alejandro: And what why didn’t that up being the business model of intercom for the people that are listening. How do you guys make money.

Des Traynor: Oh it’s it’s really really I mean it’s it’s going to come back into popularity again but we just charge money for it. So um, you pay every month to use the intercom and we deprive. Pricing along the way has been a difficult one for us because of the abstract nature of the tool. But yeah, yeah, Jerry so we’re what’s called like a b two b business of business saas software is a service subscription tool. So basically people pay everyone for access to use the software and then big companies pay us more because they’ve got. Ah, large amount of people talking to customers and they’ve got a lot of customers and small companies usually pay us less because they might be like just 2 people talking to like 200 customers or something like that. So. That’s usually how we scale.

Alejandro: So at what point do you guys? you know, realize that it makes sense to divide and conquer meaning you staying in Dublin and and your and your and know when you’re your cofounder going to to San Francisco

Des Traynor: Um, yeah I think we wanted to raise capital ah own was a Ceo vent vcs are obviously going to want to talk to the Ceo first and foremost so and um, we want to raise capital specifically in San Francisco I think trying to do it in Europe. At the time like yeah, another common question you get is could you have couldn’t you have stayed in doblin but at the time certainly it was going to be a lot easier to raise Vc Capital in San Francisco so much like actors go to hollywood and bankers go to wall street startups go to San Francisco or at least that was definitely the case in 2011 so that’s what we did and om moved over there and not just for the actual vc but also to ah to build out the business functions that we we didn’t believe we would be able to build in Ireland so you know sales marketing finance, etc. They all things were like underground in Dublin was. Very very little experience of like how to do those things for like a fast growing saas company. So so ultimately the way the company ended up was like the product was effectively Des Traynor:igned and built in Dublin. And it was like brought to market as it were in ah in San Francisco for like you know so all the gtm functions or go to market functions. We’re all that we’re all led from over there.

Alejandro: And how much capital have you guys raised to date and then also what has been the experience going from one cycle to the next.

Des Traynor: 247,000,000 is the first answer on in him. You know I think the biggest experience I’ve had I’ve only been involved in a couple of the rounds along the way. Um, the biggest experience I’d say is um, like.

Des Traynor: Early on. It’s all about like leading indicators momentum but before all of that it’s all just about the story. It’s about like the big picture. It’s about the vision. What are you trying to create like create a sense that there is a gap in the world that if someone solves that they will build a very large business and um. And like the first round was tough because ah, people don’t you know it’s not obvious when you’re building something that’s kind of totally new which intercom was in a lot in a few different ways. Ah but 1 of the ways in which it was just new is that like people wanted like oftentimes venture capitalists will try and like pattern match and pigeonholes that are like oh you’re a blah. So. It’s like oh I don’t get it. Are you guys an assistly or are you a ZenDes Traynor:k or are you a salesforce or are you a marketo and like our answer at the time was like we’re all of those things and none of those things and we’re we’re basically a direct line to your customers and that was a. Ah, trickier pitch. It would have been easier to say we’re just a really good help Des Traynor:k right? They would have got that they might have depressed the value or they might have been more skeptical of her success but did at least understand it on first blu. um but um I think early on I would say you unlike I see this as what I’m investing in tas too early on all people have is like.

Des Traynor: An idea which is hopefully summed up in like a couple of sentences and a slide deck us to head are going to go about getting to the first base on it or forever and um and in an ask which is like give us a million dollars or these days more like give us $10000000 um, and then ah. And I think like what happens over the over the the years or over the rounds assuming you’re successful is the story just shifts and it shifts from being entirely about like ah vision and big picture and like leading indicators and look what people are saying about us, etc it shifts all the way down to like ah to just show me your spreadsheets. You know. Create a data room and what we want to see is evidence of traction or whatever and um I think that’s like the ah that’s the transition. So as a result all of the like you know and you’re going to see this happen sadly to a lot of startups right now. Ah, given that like watch just is happening in the market and given the companies who had hoped to raise money over the next six months all of the jazz hands and fancy pitch decks in the world won’t save you if your spreadseeets not backing it up with like evidence or example. And so I think that’s just basically like the role of data metrics and like and just market comparisons and all that sort of stuff increases while at the same time the role of like your your hype and your pitch and all that decreases it does not go to zero I will set out like it’s still really important decomposition a company to have like clearly a big exciting future how it was. 

Des Traynor: That’s true, all the way true to go in public like you still need people to believe in the future of the business as well as the present. But for sure when they’re like investing. Let’s say hundreds of millions as opposed to like an angel check and there’s a lot more due diligence on is the current state exactly what you promised it is.

Alejandro: Got it now in your guys’ case you haven’t raised since 2018 so obviously you know you’re riding this rocket ship you know, incredible business. You know, typically you know investors you know would push you you know for hey keep keep racing keep growing like crazy. So.

Des Traynor: He so.

Alejandro: You know what’s what’s behind you know that day that thinking of hey you know let’s just not not not keep going on on on putting more more gas or more money into this.

Des Traynor: Um, I would say if there’s a few different a few different parts but first and foremost has been we like have not needed to and then secondly it’s quite a time sinknc and then thirdly like there’s been times in a markets I was being incredibly strong. Um, like you know if if we needed money we we would have got. Ah. Got it quite easy. But now times like Dis Market it’s obviously not as strong so you you know you don’t really be raising now if you if you were like stuck in a sense. Um, so it’s just it’s fundamentally like a lack of like is it a priority to to to change capital and bank and ah.

Alejandro: Um, yeah.

Des Traynor: No was’ being the answer. You know it just hasn’t been ah hasn’t been a priority versus building out a leadership team localizing entering different markets building new products. All that all that earth stuff if at any point Capital became a constraint I think that that that might change it. But I think that hasn’t been the case.

Alejandro: Got it now in terms of um, you know for the for the for the people that are listening to get an idea on how big intercom is today anything that you can share in terms of number of employees or anything that you’re comfortable sharing.

Des Traynor: I mean ah like the like I I think our employee count is somewhere under 850 to 900 range if fluctuates. We’re all hiring. You know? Ah I think more generally we’re like 5 offices we have like over 25,000 customers. They have about. Half a billion conversations with their customers every month there to things I actually care about how many customers we have and how busy are day and how many customers a day talking to that’s like an indication of the the scale of intercom and we we haven’t got em. We like we know we’re not public but revenue or anything that at the moment so sort of yeah I think. The way I would assess the magnitude of the business is mostly down to like how many customers we have on are they using us in mission-critical ways and they are basically.

Alejandro: Got it. So why? So this if you were to go to sleep tonight and you wake up in a world where the vision of intercom is fully realized what does that world look like.

Des Traynor: Um I think it’s a world where anytime anyone has to resolve anything with a business over the internet they will have an experience that is like I want to say like. Easy. Ah in that like there’s not a million barriers to talk to the business. It’s personal in that they’ll know who they’re talking to but also personal for them in that they won’t have to reintroduce themselves a million times over giving it their a account number every single time they get passed around from like 1 department to another everyone know who they’re talking to and like you won’t have to repeat any information. Ah, it’ll be outcome focused and meaning meaning like you actually just get the thing. You don’t get like go here to do that. The thing gets done for you like absolute resolution versus like direction and then on the business side of things. It will be.

Des Traynor: Effective and efficient and ultimately like you know it’ll you know, get amazing experiences for your users while still being quite affordable for your business the way I think about that is like Des Traynor:ign for the users and get results for the business. Um, and so like if you imagine if I woke up tomorrow when somebody had got ahead of us or intercoment. Got ahead of me and like realized that. Let’s say I bought I mean here like let’s say I bought these airpods I take them man. They don’t work I would go to apple.com I would click the messenger and say my airpods are broken and they’d say hey does at least the airpods you bought yesterday order number blah blah blah and I’d say that’s the ones and I’d say okay, cool. Um. Click care to report default or like we’ll report it for you. We’re going to send you out a box put it in And’ll be collected and replaced and like by the way Apple are a great company. So this this comparison isn’t even as extreme as it could be um, but right now if I have to do this. The experience is a lot messier. It’s a lot more like. You know, like you know, multiple sign-ins multiples you know searching my own email to find receipt numbers and product numbers and serial id and all that sort of shit that they already know all this just to report back and say yes totting I bought off you is broken and like you know to bring bring us back to 2011 for a second. If you got their own coffee from Colin the guy whose coffee shop. We used to work out of you’d walk back up at your coffee and say this is their own coffee and he’d make you the right one. There was no send me your receipt validating. There’s no you know 72 hour delayed was no submitted ticket. There was none of that. So I really think like we’re trying to bring that world like ah.

Des Traynor: How would you say we’re we’re trying to make that world a reality which is just every time you have to engage with an internet business. It is fast effective, efficient and personal and that’s what that That’s what the world like post intercom if you like would look like.

Alejandro: Now for you I mean you’ve you’ve invested in quite a bit of startups in ninety startups. So when you look at startups. What are you know some of the traDes Traynor: that they that you look at you know that are going to make you excited about you know making an investment.

Des Traynor: Um, will.

Des Traynor: Yeah, so there’s probably 2 categories I look at one is like you um, joining around that’s for an already like open running startup and they are kind of no- braininers. You’re just looking at like the traction and like you don’t have to tink too hard when I’m looking at ah earlier stage startups generally speaking i. I need to see a good product that solves a real problem that really matters ideally to some to something I understand but if not something I understand something I can verify really matters I think a lot of startups will fail on 1 of those tree criteria like. Either It’s not a good product. It’s not a real problem or it is a real problem but no one really cares about solving it too much like as in businesses they’re happy to just you know whatever tro headco out it or just leave it broken and they don’t really care. So um, so like there to sort of dirty initial tree criteria and like I would say. That account like you know 80% of my rejects as ended with the ones I say no thank you to they fail on one of those either. The problem is just too small or it doesn’t matter the product’s not good enough or the solution isn’t really a proper solution. Um, so like. Like that’s the first way after that like the next question that I’ve had to learn a hard way to ask is just um, like the founder’s motivation. Ah sometimes people like when I’m investing. They also want like they would appreciate like you know.

Des Traynor: Ah, call every quarter or whatever and I just I don’t have the time to do that I really don’t like I intercom as a full-time job. So I try to be as much as much as possible. A kind of 1 onone type investor who I’ll reply to stuff by email and I’ll read the out report and I do out on weekends because I actually just low startups is just kind of what I’m into. Um. But oftentimes I invest in in founders where I think all the everything lines up except for the fact that this person would sell the business for the exact price they’re raising our right now and that’s the piece that you kind of have to do an extra bit to do to due diligence on someone. It’s trying to raise off you at a $6000000 valuation and at the same time they would sell their business today at $6000000 perfectly happy then you have a bit of a concern which is that like the nature even at early stage even a tiny checks like I write. You’re yeah, you’re planting a hundred flowers hoping that a few bloom and the ones that bloom they really have to like pay back. Ah, they can’t just be like a 1.5 x or whatever they need to be like a 10 twenty forty fifty x and I think that’s a danger like um if the founders aren’t really if they like the idea of playing startup but not really doing startup. Ah, then you’ll have a problem you know so like so that’s probably the the one new criteria I’ve had it since I started. Yeah.

Alejandro: Got it now if I was to put you into a time machine and I bring you back in time to that moment where you know you were just building software. You know, thinking about maybe you know, starting a company for you guys? Um, if you had that opportunity of having a chat with your younger self and giving that younger self. 1 piece of advice before launching a business. What would that be and why I mean obviously you know you’ve been at intercom for about you know, almost twelve years I mean there’s a lot of lessons learned there along the way.

Des Traynor: Yeah I think um, this is gonna I’ll give you this answer and if you don’t like it. We can go again. We can cut the first and or maybe both will be good honestly I think some of the areas.

Alejandro: Ah.

Des Traynor: I personally would say like I got wrong or made mistakes has been whenever I’ve really accepted what is like common knowledge or commonly accepted wisdom of you know either Silicon Valley or the tech industry or whatever people will tell you things like when you hit series b you need to do the following treatings or like. Your first hire should always be a blah or if you don’t have this make sure you get that and there’s so much of that am like handed down a weirdly unverified wisdom that ah it’s it’s nearly become like a cottage industry and in and of itself where like. Vcs or even handing it down to other vcs and no one’s ever actually cracked it open and looked at and be like is this thing definitely true like things you get told like in 2011 it was like you know something like you’ll never have a big business. Not selling to small companies and like turns out that’s not true. You know turns out like. Like hopespotter phenomenal business shopify phenomenal business like loads of people have done really really well without selling to big big companies on the flipside if you choose to sell to big companies. People will roll out like a ye old big company playbook and they’ll tell you you need to do all this stuff and you need to stop doing all this other stuff. And um, and I think it’s very easy to just kind of take all that like as gospel as it were if you’re so inclined and just be like okay well I guess we have to go and do to things that like big companies do or whatever and I guess the advice then if I is to like try to net it out would be like.

Des Traynor: Don’t do anything unless you deeply like truly believe in it don’t like be very wary of like you know trust falls with people who you don’t know like ah so I I think um, oftentimes you know I found myself lacking in in ah in confidence to say hang on a second. I know I don’t know how this works but I also know that what you’re telling me doesn’t make any dumb sense and I wish I had more like fortitude earlier on to push back in those in in those areas and like um, you know, reject certain either like strategies or or like. You know org Des Traynor:igns or whatever it might be right? like ah they’re all like different sort of like implications of an opinion and um, like that’s probably the 1 thing that I wish I gave to me yourself. It’s some version of like back yourself or at the very least seek to learn but don’t execute until you fully understand that that’s probably the biggest one. Um. The only other one I’d say is um I think like you know, a lot of us are like this in intercom we have postponed any real celebration for like 11 years at this point and it’s always been like the next round or like you know what? we I’ll be really happy when blah. I’ll be you know or like you know we should really have a proper party to celebrate blah like it has literally never happened. You know? Ah so it’s kind of weird to like be you know 11 years in I like you know in some senses intercom has like ah.

Des Traynor: Certainly from the point of view of a thirty year old as who started it in like 2011 and intercoms eclipse to all of my wilDes Traynor:t dreams den ah at the same time I’ve never had once had a chance to celebrate that and that’s kind of weird. Um, so maybe a second message will be just like.

Des Traynor: You know, please take time to enjoy the journey because it almost feels fickle to do it Now you know.

Alejandro: Yeah know I hear you? Well I I love that very profound day. So for the people that are listening. You know that will want to ah reach out and say hi. What is the best way for them to do so.

Des Traynor: Ah, Twitter I’m just dad trainer just my name ah on Twitter and it’s also like dad train. It’s arm dadzz at intercom or Des Traynor:k trainer gma or whatever if want to drop me a note. But yeah, but copy here for anyone.

Alejandro: Amazing! Well hey this thank you so much for being on the deal maker show. It has been on on Earth to have you with us.

Des Traynor: Um, thank you for having me.

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