The Twenty Minute VCDes Traynor: How I Founded Intercom; Product Marketing Tips; Feature Creep | 20VC #907
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150 min read · 30,008 words- 0:00 – 2:00
Founding moment with Intercom
- DTDes Traynor
Three, two, one, zero. You have now arrived at your destination.
- HSHarry Stebbings
Des, this is such a joy to do. As you know, I've been a long-term admirer, fan, so thank you so much for joining me today.
- DTDes Traynor
Thank you for having me yet again.
- HSHarry Stebbings
Not at all. I do want to start though with a little bit of context. We see Intercom in all of its glory today. What was that founding aha moment for you and the team with Intercom?
- DTDes Traynor
I think we had a few different ideas. So we, we were originally a consultancy building software for other people. There was a few ideas on the go. Ones that, like, you know, at times looked hilariously bad. Like, we had an idea for, like, a white boarding product, and, uh, and that, like, you know, ultimately looked like not a good idea contrasted with Intercom. But then something like Miro comes out, like, years later, and you're like, "Maybe it wasn't such a bad idea." Um, however, with Intercom, uh, we ha- we're building an actual way to communicate with our customers from a previous product, uh, and we wanted to communicate inside the product. And the real sort of spark was, like, when we realized how much more effective that was and how more, how r- people were just quite excited about that. I remember Owen, at the time our, our, uh, former CEO, current chairperson, saying to Ciaran, like, that this could actually be a huge idea by itself, this little talk to customers in your product type thing. And, um, and when I heard that, my response whenever I think, "Ooh, could this be an idea?" I just immediately go into, like, "L- l- let's, like, what's the actual strongest, like, iron man case we can push to support this? Or a steel man case." So I was like, right, what are the trends, uh, whether it's messaging or whether it's, like, uh, the rise of web software, whether it's the rise of SaaS and the, the need for relationships. I started to look at, right, okay, this fits, it supports so many current sort of tectonic shifts, and then obviously the, the real click was once we actually offered it to other people and we saw them use it, and we saw them, like, rip it out of our hands, and be like, "Oh my god, I love this thing. How did, you know, how, how did my life exist without it?" type thing. That was when it was like, right, clearly we're onto something. And that was the decision then to, like, close the consultancy, let's get going, and let's go all in on this.
- HSHarry Stebbings
Uh, so
- 2:00 – 3:55
Idea or Founder
- HSHarry Stebbings
I, I want to touch on something you said there first, which is kind of the idea selection process for you. I'm so... And VCs always say, "Oh, it's all about the people, it's all about the people." I don't care if I hate your idea if I believe in you so much. I've invested many times, and actually, it was Elizabeth Yin on Twitter who said the other day, "No, no, no, like, actually the quality of the idea really matters, and you have to be excited about it." Which camp are you in? Are you in, like, the, "Fuck it, great founders find the market and find the product over time," or do you have to like what they're doing when you invest?
- DTDes Traynor
I think, uh, this is, this is, like, gonna n- not be a satisfying answer. I look at the multiple, like, the quality of founder times the quality of the idea. But if I ha- if you're telling me I can only have one, I'll definitely pick the quality founder over the quality idea, 'cause I actually, I, I think ideas are only good until that you say them out loud, and then all of a sudden everyone hears about it. So, like, uh, there's an Intercom spin-out right now, uh, called Equals, right? And Equals basically it connects spreadsheets, like Excel, uh, like, like s- sorry, it is a spreadsheet, and it connects to actua- data warehousing. and apparently that's a huge idea. And everyone who's ever used a spreadsheet, the first qu- question you ask them is, "Do you connect it to other sources of information?" They're like, "Oh, well, I take an export from a snowflake and import..." The very second they hear that idea, they're like, "I w- I'm in. I want it. Let me invest. Let me buy. I want the product right now." But now that idea is out there. So if alls you had was that idea, there's gotta be at least a hundred other people trying to copy that idea and do it quicker than you and better than you. And if they care about it more than you or they're just better than you, they're gonna ghost you. So being first doesn't matter, and I think, like, there's some of it attachment to the idea of, like, the uniqueness of the idea is only useful in a world where being first matters. And I just, I think it's very rare you can sustain the head start if somebody else is either better funded, just better, better resourced, more passionate, and all's you are is the guy who came up with the idea.
- HSHarry Stebbings
Sorry, can you unpack the b- being
- 3:55 – 5:45
Does being first matter?
- HSHarry Stebbings
first doesn't matter? 'cause is there not someone else who's always better suited? Uh, like, Google could put their mind to any idea, resource it better than you, and you're fucked.
- DTDes Traynor
I d- uh, so I, I don't actually think that that's true. I think, like, you know, Google have, like, tried to put their mind to, like, god knows how many things, and you still see the emergence of god knows, uh, how many products. Like, like, why, w- why isn't Slack part of the G Suite, you know? It's b- because they can't put their mind to that. Why does Figma exist? 'Cause they can't put their mind to that. Like, w- why is Superhuman doing well? 'Cause they can't put their mind to that. So I, I, I don't think... Like, I think it's like, you know, in a case with Google, it's more like what do they actually prioritize, and the answer is their core businesses, of which they have, like, five or six or seven, like, YouTube, G Suite, um, I don't know, whatever else, Search, Ads, blah, blah, blah, right? Um, I think being, being first doesn't matter is an interesting... Let's say me and you have a really dope idea for a really smart take on project management, and it involves, let's say, you know, if you wanna wind the clock back, let's say it involves, like, the idea of a metaphor of Post-it notes that you can drag and drop around the place. Give it a year, and everyone will have it. If it makes sense, give it a year, and everyone will have it. And then what are you left with? And if what you're left with is, "Well, we had it first," and you start running adverti- advertising campaigns saying, "The original," you're kind of like, you're screwed, you know? Because, like, no one actually cares. Like, when you pick up your phone, you don't really care, is this the first touchscreen or not? Turns out it wasn't, but it doesn't matter. Like, the question is do you, uh, can you sustain your advantage? And I think if alls you are is the person who had the idea but you don't have that much passion or you don't have that much ability or whatever, uh, anyth- anything there, I, I just, I don't think, like, a mediocre person with a unique idea will work.
- HSHarry Stebbings
I don't believe in defensibility on day one. As you said there, I think anyone can have an idea, uh, uh, and there's lots of people who have relevant backgrounds. But I think, like, actually with my own media business, defensibility
- 5:45 – 8:35
Is defensibility built over time?
- HSHarry Stebbings
is built over time and-
- DTDes Traynor
Yeah.
- HSHarry Stebbings
... the processes that we do, and the products that we build subsequent. Do you agree-
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
... with, like, defensibility on day one doesn't really exist?
- DTDes Traynor
I th- like, i- i- like, m- real defensibility, no, it does not exist. I think, um, like, there are a few apps. I mean, like, uh, uh, I'm just trying to think of a good example. Like, Figma might be one, or you know, like, Zenly, the, the, the Snapchat app?
- HSHarry Stebbings
Yeah, yeah.
- DTDes Traynor
Like, th- things where it's, like, really beautifully crafted, really high-end engineering, and really hard to copy. Tha- like, those sort of products, when you see them first, you're like, "Hmm.... it's going to take a long time to get to where these people are today. And like, the way I describe that in, like, startup... uh, you know, when I'm t- talking to startup companies who are looking for me to invest, is I describe the length of the road to the starting line. And I would call it, if you say you Want to compete with Figma, I'd say, "Jesus, Des, that is a long road to the starting line." Which basically means-
- HSHarry Stebbings
But they were, they were, like, three years in the dark.
- DTDes Traynor
Yeah.
- HSHarry Stebbings
No offense, VCs had almost written them off 'cause they were like-
- DTDes Traynor
(laughs)
- HSHarry Stebbings
... "What are these guys doing?" Like-
- DTDes Traynor
Yeah, absolutely. And it's the same when you say, like, uh, "We're going to work on a new email client." I'm like, "Yep, long road to the starting line." 'Cause I'm like, eh, I can tell you what your first two years of roadmap is, and then at the, at the end of that, can you add something unique on top? Who knows, right? So I think, like, day one defensibility is rare, but, uh, every now and then, some company does emerge with something that you're like, "Wow, if you want to copy that, you'll be a long time working on that." And in the, like, it might be, like, a year, year and a half, or in Figma's case, as you said, like, um, two-plus years. I think anyone who's like, right, like, let's say Adobe probably saw Figma, and they're probably smart enough to go, "Wow, this is a threat to one of our big cash cows." And if they dispatched a team of their brightest, which I'm not saying they did or didn't, uh, and they went at it full time, in two years time, they'd have to hope that Figma somehow froze, w- to give them that much time to catch up. And Figma ain't freezing, and Dylan's too smart a guy to, like, not make ma- m- m- monster progress.
- HSHarry Stebbings
So do you like it when a startup comes to you and pitches a long road to the starting line? Because i- it is defensible.
- DTDes Traynor
I- if they know what they're doing, yeah, definitely. The, like, the only, uh, the only sort of test I'd say there is sometimes, like, my advice in those cases is work on your differentiators first. So, in the case of, say, an email client, "Oh, we've a new take on email," I would say, "Right, here, here's what I believe. I believe you're a competent engineer. I believe you can work out SMTP and IMAP and spam filtering and all that. Like, let's just push all that aside. I don't want to see a single engineer working that. Show me the thing you're going to build that's actually new to market, even if the email stuff doesn't work, right? I don't care. Like, I'm sure you'll solve the rich text editor problem, but I need to see the difference early." Don't tell me after two years time, "We finally caught up with Gmail, and now, with three months of runway left, we're going to add in the thing that makes us different." It's a waste of time. You have to actually, like, acid test the differentiators first. But in general, I'm not against it, that, uh, you know, uh, we h- we have to go dark for, like, two years to produce a new monster. I don't have a concern with that.
- HSHarry Stebbings
When you're looking at, like, new angel investments,
- 8:35 – 10:40
Do you engage in market size analysis?
- HSHarry Stebbings
d- I think the biggest mistakes I've always made are market sizing.
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
I underestimate the size of the market, or I actually think it's bigger than it is, and it's actually smaller. Do you engage in market sizing analysis, thinking? Do you think it's even worth it if we all acknowledge that we always underestimate how big markets are?
- DTDes Traynor
I, I, I don't engage in it, and the reason is, um, like, the checks I write... So this is where, I mean, you're slightly different in that, like, the vol- the volume and the size of the check is probably slightly off. You're larger than me in both ways. Um, but, so for me, it, like, you know, if it was, like, you know, left-handed dentists in Dublin, yeah, I'm not going to invest, right? Like, but, you know, uh-
- HSHarry Stebbings
(laughs) .
- DTDes Traynor
... if it's, um, I, I only need the market probably to be, like, around a billion of, like, total revenue spent for, for, like, for this seed check to turn into a valuable series A or whatever. It doesn't need to be a monster. However, the way I actually do it is not, like, by, you know, 'cause, uh, uh, startups, the founders will often come at you with, like, crazy, like, projections and, like, Gartner estimates and all that. Like, what I actually try to look for is just basically what is the problem, or what is the problem you solve, how many people have that problem, and how big a problem is it to the people who have it? Like, um, a big problem, to me, is something that happens often and matters a lot. So, like, I don't know, email, like, communicating with your work colleagues. Like, these are, like, big problems. Talking to your customers, that's a pretty frequently occurring problem that you'll probably spend money on. Whereas when someone says, "Oh, this is, like, the, the app that checks in to see how your employees are doing on the third weekend of every we- uh, whatever," I'm like, "Yeah, that doesn't, it doesn't sound like as big of a problem, so I'm gonna put that into the very low category." And in that world, I'd want to see near perfect execution 'cause the only way that market makes sense is if you own all of it. Uh, if that ends up being, like, a, a sort of, um, a cottage industry of, like, 15 different bootstraps companies and you're, like, going to take one slice of it, then we're into, like, you might tap out at $15 million in ARR on. You're asking for a seed at a value of 40. You know, that, that, that's, like, where I'm like, "All right, I'm out." But, but honestly, I'm out there earlier than the market size. I'm out 'cause I'm just not that interested, 'cause it's not, it doesn't sound really big, you know?
- HSHarry Stebbings
Okay, f- final one, and then, uh, we'll... 'cause this is totally off schedule. (laughs)
- DTDes Traynor
(laughs) Yeah, that's okay.
- HSHarry Stebbings
I'm like, like, CAC and LTV,
- 10:40 – 12:57
CAC and LTV in early stage
- HSHarry Stebbings
I just think it's hilarious when, like, seed and series A companies kind of pitch it, and it's like they will change completely over time. Like, this-
- DTDes Traynor
Yeah.
- HSHarry Stebbings
... profile is cheaper than that profile. This cohort was totally different.
- DTDes Traynor
Totally.
- HSHarry Stebbings
Do you, how do you think about, like, the importance of, like, CAC to LTV and, and metrics like that at the early stage? Irrelevant, don't bother?
- DTDes Traynor
I, it's not that, like... They are relevant. I just don't think most startups are ca- Like, I think if, if someone's coming to you at that early a stage and they have a really, like, dialed read on their CAC/LTV, I'm like, "How is that important? Like, why are you working on that versus working on, like, building a great product?" Like, I think, um, all these numbers matter, but they matter at scale. They just don't matter early on. What I'm way more interested in is, how are you going to get customers in a way that your competitors can't? And if their answer is like, "Oh, we're going to outbid them for CAC/LTV," then sure, let's dig into that. But, like, if, if the answer is like, you know, thought leadership, I'm like, "Right, show me the sort of thought leadership you're gonna do." If it's like, "Oh, we, ha- we're gonna do YouTube," or show me a, show me an example of a video or whatever. I, I... The con- conversation that, where most startups fail out is not the efficiency of CAC/LTV. It's most, it's like, it's a blank face after I say, "Um, do you have a differentiated route to customers, or are you just going to be bidding it out with the rest of them?" And-
- HSHarry Stebbings
So, so, sorry, I, I'm jumping in. I agree with you. I ask the exact same thing as a distribution mind like you, totally. I just never hear, "The answer that I want." I, I, I'm literally 99.9% unsatisfied.
- DTDes Traynor
Yeah, I, the only times I've been satisfied is when, um... The best way I could describe it is like, um, when it's a closed industry. So, like, when I was talking to the folks at Hopin today, like, they're like, "Well, we need to just reach every event organizer on Earth and every company that organizes eve- events on Earth." And we actually have, but we, we, like...... not quite there where it's, w- we've kind of got those lists already. And I'm like, so, so, so, w- we're, we're not... Like, the first three quarters of most marketing teams' efforts, we've already passed, which is find the people. We have found the people, now we need to have compelling reasons to get them to use it, and it's going to be an outba- outbound campaign, and it's gonna be expensive, and we're going to be sending them gift baskets, and we're going to be doing all that stuff to try and get them to pay attention to us, but that's ultimately the plan. Then I'm like, "Right, that makes sense. I believe you're working in a closed market, and I believe you can actually identify all of your targets." Uh, it's just different when someone says, "We're, we're selling to startups," you know?
- HSHarry Stebbings
Mm-hmm.
- DTDes Traynor
'Cause their plan is go number one on Hacker News and, and repost on, on Product Hunt every few days.
- HSHarry Stebbings
Yeah. No, listen, I'm totally with you. I, we,
- 12:57 – 16:00
Why is angel investing good for active officers?
- HSHarry Stebbings
we were speaking about your angel investing. You said something before being that angel investing is good for active operators.
- DTDes Traynor
Yeah.
- HSHarry Stebbings
Why, why do you think so, Des?
- DTDes Traynor
Yeah, so, um, I think since I wrote my very first check in the very first company, which was a company called Workable, uh, it was a recruitment software company, and I've probably written, like, 50 or 60 since, I think, um, a few things I've learned. One is, like, how, how little tolerance you have for excuses when they're outside of your business versus when they're inside of your business. So, when someone tries to pitch me on a, on a thing and they say, "Oh, well, the reason it hasn't taken off yet is 'cause, oh, well, we had to, like, you know, let go of our VP of engineering, and we've got a new one now, and she's awesome," blah, blah, blah. Like, I just net all that out to, "We couldn't get it done." So... And, and I make my decision based on that. And yet, i- if internally someone's asking me, "Why did such and such a thing happen?" I'm immediately going into the same mode of, "Oh, well, we couldn't blah, blah, blah." And like... So I think it, it's definitely, uh, sharpened my sort of, uh, appreciation of how other people will see Intercom. I think that's one whole piece. I think secondly, seeing the, uh, uh, the internals of other companies, uh, and learning how they make decisions is really useful from understanding an Intercom buyer's perspective. Uh, like, is in... Under what grounds would you adopt Intercom? And like, kind of relatively speaking, in all of the priorities in your world, how important are we? 'Cause we're... You know, in our heads, we're, oh, you know, i- in your head, like, you're the number one podcast on everyone's list or whatever. But in practice, you're in amongst five others, right?
- HSHarry Stebbings
Yeah.
- DTDes Traynor
Similarly, like, with Intercom, we think, "Well, well, surely they've got at least 10 people talking about Intercom on a daily basis." But no, it's actually just Joey in the corner working on new apps or whatever. You know, so like, uh, so I think getting a sense of, um, your own importance as you rank in other companies is, is useful as well.
- HSHarry Stebbings
How does, uh... I'm sorry, how does angel investing give you that perspective?
- DTDes Traynor
So, do... Uh, I guess, uh, uh, literally writing the check doesn't, but the time you spend with the founder does. So, I usually, like, you know, my take on how I angel invest is I, I try to spend as little time scheduled as possible but a lot of time unscheduled, and by unscheduled, I mean asynchronous email or whatever, right? So 'cause I'm, I'm just... I've always been interested in startups. I'm just, I just love them. It's like, I love seeing businesses grow, I love diagnosing why pr- why businesses are sort of flat-lining or struggling. And, um, so what the, what the check does is kind of gets you a stream of information about it, like a new sudoku that you can kind of try to unravel, and you can throw in suggestions. Or you can see this, the inside of, like, as is the case in some of the investments, like, you just get to see inside a rocket ship that's just humming, and you learn. You see, like, like, it, it... You know, people don't think this is true, but I'm humble enough to say, yes, Intercom is like a series, what's that, like, D or whatever company. We don't need to raise, so h- hen- hence it's not E or F or whatever, but like, um... But I can learn a lot from a series A or B person 'cause I, 'cause, like, when they're wonderful executors, they're wonderful executors. I've invested in companies that have, like, gone on to surpass the valuation of Intercom many times over, and the founders have turned into absolute monster CEOs and monster COOs along the way. And, uh, and so I... You, you learn a lot from seeing success and how that performs.
- HSHarry Stebbings
If you, if you look at
- 16:00 – 18:18
One company that blew you away
- HSHarry Stebbings
those ones that absolutely blown it away, is there one company where, and one CEO, which has shown you the most, and what have they shown you?
- DTDes Traynor
So, um, I, I'll answer this, uh, in a slightly different way. So like, like I've invested in companies like, let's say like, you know, Stripe is on one end, right? Like, of just, like, a total absolute outlier. But I'm not gonna say blah, blah, blah, 'cause like everyone knows Stripe, and it's, it's kind of too easy. Um, but a company where I've seen is that had, had, say, more close access and watched it take off was, say, Miro with a, with a... A- Andrei, uh, Coussiat is the CEO there. They've just been an execution machine, uh, for a really specific problem, and they kind of ha- stood up against, um, an external what could have been a threat in FigJam, and they've done really well through that as well. Uh, so that, that's a company where I've just watched it pretty much from early doors, really do well. Um, another one, which is like earlier-
- HSHarry Stebbings
What... Sorry, what... Sorry, I'm, I'm clicking now. What do you think they did well? Is it just speed of execution?
- DTDes Traynor
Focus on speed of execution. So I think for... Like, the, the easiest thing for a company like Miro to do, I think, is to get notions about becoming Microsoft Office and start to, starting to branch out and becoming a document editor, and all that sort of stuff, because everyone tells you you need to go become a mul- multiplatform suite, blah, blah, blah. Like, you get all the, kind of, like, the narrative of expand your TAM now, et cetera, et cetera. Maybe that's the right thing for them to do, but what they have actually spent all their time doing is perfecting, you know, uh, like, online multiplayer whiteboarding. And, uh, and I think that's a really important thing for them to do. Uh, so like, that, that... I think, like, this... I'd say it is probably focused, intense execution, uh, without willing- without, like, letting their kind of, like, newfound status distract them from it. Because when you start telling... If you have to do... If you just sit down with a journalist and say why you're now worth whatever billion dollars they're worth, you feel obliged to say all this new shit, right? Like, you feel obliged to say, "Well, we're actually gonna become this, there's a, there's a metaverse play, and we're thinking about augmented reality, and we're releasing some hardware." Like, that's like the, the easiest thing to do, say all this dope shit so you sound famous. But actually, just, uh, the intensity of the execution there has just been awesome.
- HSHarry Stebbings
(laughs) I knew that I was smoking my own shit when I said I was elevating the consciousness of investments. (laughs)
- DTDes Traynor
(laughs)
- HSHarry Stebbings
I was like, "Fuck me, Harry, you've been watching too much Adam Neumann."
- DTDes Traynor
(laughs)
- HSHarry Stebbings
Um, spea- speaking of that though, I mean, we're kind of brilliantly intermingling schedules here,
- 18:18 – 24:22
When is the right time to release a 2nd product?
- HSHarry Stebbings
but I'm pleased with this. You said there about kind of expanding sooner or beyond into text editors and more than you should do. Product question-wise, it's fucking hard. When is the right time to release a second product? How do you advise founders on that?
- DTDes Traynor
I, like, I'm always hesitant to give any, like, super structured advice because there's just so much tacit knowledge you get in the building. But the things that I would say to think about are basically, like, um, uh, one is, one is, like, a lot of this is gonna be kind of boring and tactical, but I think that's honestly what a lot of listeners come to you for.
- HSHarry Stebbings
Yeah.
- DTDes Traynor
Um, one thing you'd have to look at is, like, uh, so starting with the boring shit, can we actually recruit enough engineers and designers and PMs to actually own a second product in a way that doesn't harm the first product? Because that first part still needs new people as well. You need backfills, you need to continue the investment there. So one whole piece is just very tactical. It's like, can we get the team in? And oftentimes, that comes from opening a second office or from acquiring, uh, you know, an Aqua Hire or something like that. But, like, are we gonna be able to get the people in a way that doesn't cannibalize the success on what is currently the only thing we have that works? And so that, that's one whole piece of calculus. Are we ready to do it from a staff side? Then separately, do we credibly believe... And this is a two-parter here. One is, like, can we definitely, uh, like, is the ROI of adding a new product definitely greater than increasing the maturity and p- possibly the TAM by, like, going up market or whatever, of the current thing we have? So if we have a project management tool and someone wants us to do a time tracking tool, are we sure that doing the time tracking tool is going to be adding more value to the overall business than just really nailing this project management tool or whatever it is, right?
- HSHarry Stebbings
Mm-hmm.
- DTDes Traynor
Uh, and then thirdly, uh, is there value in doing both of these two things under the same company? Like, and this, this is a question of, like, brand architecture in a sense, right? 'Cause if you really, if you think, "Hey, I can find a second team and they're gonna go and do this sort of thing," why not just start a second startup, right? There has to be some, like, multiplicative value where actually both products end up, uh, like with unfair advantages because of their cohabitation. And, and I think, uh, like, you have to b- so they have to share either a source of truth, uh, you know, customer record or something like that, they have to sh- have some sort of shared, uh, uh, entities and shared workflows and shared UI. That means that you can do the second product better than some random person off the street could do it, and that your customers ideally will buy it off you because they prefer that advantage too. So, like, the, that, that, like, the, like, the first trigger point for me is always, like, are we sure we're tapped out with what we're currently doing? Or, or, like, maybe tapped out's probably too negative a word. Are we very confident in the trajectory towards a really successful outcome for product A? And then I, th- then if product B, are we ready to hire for product B? And then if we're picking B, are we sure we can do it in a way that doesn't hurt A? Are we sure that it's valuable and it's more valuable than just simply continuing on A? And then lastly, does A plus B m- m- like, uh, d- like, is that multiplicative or is that additive?
- HSHarry Stebbings
(laughs)
- DTDes Traynor
Are you gonna get, like, uh, you know, i- i- you know, are you basically adding two things together or are you multiplying two things?
- HSHarry Stebbings
I, I, I wanna start on number one there in terms of the resourcing with the engineers and the team needed. I'm always in two minds when it comes to second products. Do you do the skinny budget MVP test and iterate in a very lean manner, or do you really allocate resources to it and concentrate capital? Because you should do it if it's a meaningful effort for you. How do you think about that two-minded process?
- DTDes Traynor
I actually think you have to do both. Um, I think you have to, you have to prove out that you have some, like, some actual, like, um, alpha in the mo- uh, that you, that you can do something that no one else can do. So, like, going back to the idea of, like, uh, ship your differentiators first. Like, show me this thing working. Like, so, uh, so let's say y- you know, I don't know, I'm trying to... Uh, let's say you have a project management tool and you wanna do, like, whatever, HR tool or... Show me why are you better than, like, Workday or Bamboo or Humans or whatever, right? Like, give me something that says that you're, like, that this is actually worth building and it's actually new to market as opposed to new to your company. And then, uh, and then if you can show that, then I think you actually have to show the full set of resources at it. Now, this is where the advice would differ depending on the stage of the company, but, like, if Intercom launches a service tool, which we did in March, we can't be, like, limping in with an MVP that doesn't work. Uh, it would, it would actually be brand damaging. We need to, like, it needs to have all of the traits of Intercom, which means in-context, AI, ML, reporting, mobile, m- mobile plus web, blah, blah, blah. Like, there's, like, some kind of, like, uh, default assumptions we want our customers to make when they see the Intercom logo. And, uh, and we need to meet all of that, which means you have to fully resource it. 'Cause otherwise y- like, whereas a, whereas, like, a, a Y Combinator startup would just eke away one feature at a time, we'd do brand damage if we asked our, like, if, you know, if we asked one of our largest customers, uh, let's say Atlassian or whatever, "Hey, we have a new service product. Why don't you give it a try?" And they try it out and it doesn't work or it only has one feature, they're like, "Mother of God, what are we paying you for?" You know? So you, you have to kind of make sure that that, like, your release matches the, the sort of brand posture that you wanna have with your customers.
- HSHarry Stebbings
I like that a lot, and I actually hadn't thought about that in terms of different staging of the companies and how people perceive the brand. I, I wanna touch on that. You mentioned obviously the new product that you released there. Um, eh, I think we learn from our mistakes often. When you think about the new products that you've released, what are some of the biggest mistakes you've made when releasing or contemplating releasing new products, and how did that impact your mindset?
- DTDes Traynor
Um, I think one area that's most difficult to think about is what is a product versus what is, is, uh, just a paid upgrade to your existing platform. And, like, under what grounds should you say, like, this is a new product or this is just an extra tab that you pay an extra few dollars to unlock? And I think in general, um, there are loads of arguments as to when you should do one versus the other. Usually it's around, like, does it have a distinct buyer that for whom the other product wouldn't r- wouldn't appeal to? And if so, do you have a cross-sell/upsell plan? Like, how do you, how do you make sure that these people hear about each other and buy it such that it doesn't end up just being an entirely separate line of business? I think, so, like... So, and we've made mistakes there. We've definitely made mistakes there. We've confused products with features and features with products. And we've, we've had to unroll that and, and, uh, and, and fix
- 24:22 – 26:08
New product vs new feature
- DTDes Traynor
that back again. And then I, I think, um-
- HSHarry Stebbings
How s- how do you, how do you know whether it's a feature or a product? I often have with this with founders where I sound like the douche VC when I say, "I think it's a feature, not a product," and they go, "Fuck you." (laughs)
- DTDes Traynor
Yeah. I think, uh, I, I, I, so I totally agree, and I think, um...... with a ... If you're looking at it from the venture capitalist's point of view, or even maybe, like, from the CEO's point of view, you might be tempted to think everything's a product, because you're actually, you're, you're actually thinking about its impact on potential TAM expansion, and you're thinking about revenue and all that. I think you have to look at it from the customer's point of view and say, "For the vast majority of our customers who use our current product, would they expect this to be part of a connected workflow within the platform? Or do they think that this is somewhat, uh, exogenous to what, uh, what they're currently doing here?" Uh, and then, there's other nuanced pieces like, how are they currently solving the problem that this feature/product, uh, solves? And if the answer is, they're doing it in Excel or whatever, then yeah, you could probably, uh, argue you put it in as a feature. If they actually have an, another platform where they, like, track holidays or whatever the hell it is, right? Whatever the feature might do. Uh, if they have a whole other solution out already, that's usually a sign that they were willing to buy two different products in this space, so you actually could justifiably, uh, claim that this is an entirely separate product, possibly with separate buyers and all that. But I think you have to look at it not from a balance sheet, or, or not even from a tactical perspective, or even a product purist perspective, but just (clears throat) what do you, what do your customers expect, and how are they currently solving the problem? Uh, and specifically, your, like, your target customers. 'Cause your free customers will expect everything to be for free a- attached to everything, and you'll just end up with this amorphous blob of a product.
- HSHarry Stebbings
(laughs) We're gonna get onto messaging, but in terms of like ... So we mentioned that as a release. Not all products work, as we mentioned some mistakes there. The hardest thing is how to know when to kill a product. And sometimes-
- 26:08 – 27:38
When do you kill a new product?
- HSHarry Stebbings
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
... you have to. How do you know when to kill a product or feature? You need enough data, but you don't want to leave it out too long. How do you make that decision?
- DTDes Traynor
I think trajectory, uh, h- like, it, (coughs) it is like the defining trait. So like, uh, over time, does this product propel itself? Is it, is it growing or dying by default? And you might do a lot of, like, customer marketing, where you give it, like, uh, like effectively, like, you know, uh, incubation in a sense. Right? You're like, you're putting it on life support by, like, reminding your customers every month, "Don't forget about this thing over here." And they all try it once, and then it fades away again. If it doesn't have its own momentum, uh, as a feature or a product, and if you find yourself just constantly trying to push and nudge, and you can't get customers to stick to it, that's generally a sign that as a feature or product, it's like, it's not working. Now, you could rebuild it. You could do a lot of customer research, and you could find out what's going right or wrong. Uh, but like, the main point is, you have to actually get to the bottom of what's broken. And oftentimes, it's like you had an assumption about how the market worked or how your customers thought, and you were wrong. And that's okay. That's like, your, your job is to be right and wrong. So, uh, and then when you're wrong, the question is what do you do about it? And the answer is you end of life it, which means you stop taking on new customers. You tell all the current customers, "Hey, I know you depend on this thing. It's gonna fade away over 12 months. Here's our suggested, uh, like, uh, migration path off to some other way to get it done," if, if they, if indeed, deed they care. And you just chalk it up, and just make sure you go back and delete that code and fully rip it out of everything, 'cause, uh, you don't want, like, these sort of zombie features hanging around.
- HSHarry Stebbings
I, I, I totally
- 27:38 – 35:50
What is great product marketing?
- HSHarry Stebbings
agree with you. I, I, I do wanna ask you now, I think a lot of times actually, sometimes the products are good, but they're messaged and communicated in the wrong way.
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
And, um, I actually think the state of product marketing today is so shit.
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
Um, I always say to founders in, in calls, "You have a billboard on Times Square, less than 10 words, 'Sell me this pen.'" (laughs)
- DTDes Traynor
Mm-hmm. Yeah.
- HSHarry Stebbings
Uh, so few can do it, at all. "Uh, haven't thought about it. I'm not su- ... Ooh." It's, it's abysmal. Um, my question to you is, I spoke to Matt at Iconic. One, how do you think about the state of product marketing today? And Matt told me how amazing you are at it. So, what does great product marketing mean to you?
- DTDes Traynor
Hmm, that's very kind of him. I don't know, I wouldn't really describe myself that way. I think that, like, the, one of the reasons we think it's bad is, um, we don't take enough of a, uh, both a user-centric and a buyer-centric point of view of product marketing. So oftentimes, like, we confuse something like a, like AirPods marketing, right, which is, like, glorious, right? But, but what we mean by glorious is, one, the buyer equals the user. There's no buying committee. There's no proof points that they need. And no one's shopping based on data or a competitive feature set. It's an entirely brand play. So it's very different to say like, um, oh, like, to say Asana launching a new way to do Gantt charts or something like that, right? Uh, so you have to think about it from a point of view of like, not all products can go to market the same way. Tesla can market a car differently than like, you know, Salesforce can market a chat client or whatever, right? So, uh, the other problem ... So that, that's one problem, which is we always forget that, and then on, and then specifically, like startup marketing, startup product marketing, generally, uh, it leads, it has always defaulted to, here's a big screenshot, and here's a one-liner. And I think that's totally fine in a world where the screenshot is really self-evident of what is going on. So if I posted a screenshot of like, say, Riverside.fm that we're chatting on right now, I think it'd be pretty obvious what's happening, as in the product is self-evident, right? Uh, that's not the case for like, a load of like B2B SaaS, where it's just a load of like text input boxes and a graph, and you're like, "What, what is this?" It could be anything from payroll software to Amplitude or whatever, like anything in between. So I think you have to bear in mind, a lot of people think their product ha- sells itself, therefore, let's just put a big dopey screenshot up here and say like, you know, "Data reinvented," or something like that. And like, no one has a clue what the hell's, what the hell is happening. And I think that is the kind of like state of art at the bottom of the market. So I think, like, the challenge for product marketing is one, you have to work out what do your users and buyers want to know, and they're not always the same thing. And then two, what is the best way that you can, uh, show why you're best at it? So if you-
- HSHarry Stebbings
So you-
- DTDes Traynor
... think ... Yeah?
- HSHarry Stebbings
So if we take one ... Uh, sorry, I just wanna make sure we cover it. So if the buyers and the users aren't the same, do we try and hit them both with the same one? Go back to that billboard, go back to that landing page. Do we hit them both with it? Do we say, "Fuck it. We're not gonna go for the buyer. We're just gonna go for the user. Fuck it. We're just gonna go for the user and not the buyer"?
- DTDes Traynor
Yeah.
- HSHarry Stebbings
Wh- how do you think about that?
- DTDes Traynor
The challenge there is really like, what is the typical adoption path for a product? So like, if we take, uh, if we take Intercom, uh, we've been trying to avoid it so far, but like, um-We have a beautiful inbox. We re-, we, we re-released it, like, a couple weeks ago. It's next generation, like, fanciest piece of, uh, like, I would say, customer help support, customer support inbox product on the market. But the person who's buying Intercom or adopting Intercom, they're not actually the frontline user of the product. They're not actually... Y- you know, they're, like, the VP of support in a 2,000-person company. They actually don't even see the inbox half the time. They might see the reports that come out of it, but honestly, even in those cases, they're probably looking at that in Snowflake or something. So they're really not that in the loop. Alls they care about is, "What can you do for me?" And, and, like, what, what, like, what's slightly upmarket, like, were when the buyer doesn't equal the user, the buyer's questions are basically, "Well..." I- if, this is gonna sound quite reductive, and it kind of is, but... "I have two numbers to worry about, Harry. Uh, are you going to make me money or save me money, and, and if so, how? And why should I believe you?" And that's what the buyer wants to know, 'cause they're just trying to, like, run their own PnL and get promoted forever. The user has a different set of concerns, which is, "I'm trying to do my job and get promoted, and I need to believe that your product's gonna make me more effective, more performative. I'm gonna enjoy using it more. It's gonna... Like, do you work on mobile? Do you do this? Do you do, like... You know, how can you support me in my life?" is basically the, the questions. Now, as to which goes first, you absolutely have to do both. If you're billboarding in Times Square, the actual answer would be, who's more likely to be standing in Times Square looking at that billboard, your buyers or your users? If it's your users, go with that, and go for, like, the bottoms of adoption. Like, you know, the p- product-led growth adoption sort of model, where, like, everyone's like, "Oh, I wish we could use Intercom," which works well for us. Like, "Oh, I wish I could use Dynamo Inbox. It looks so n- it looks so nice," blah, blah. And then you hope that enough of that groundswell pressure pops into a VP of customer support saying, "I've been hearing a lot from my team about your product. Uh, I'd love to hear what..." You know, and they'll, they'll hit you with the real questions, which are, "What are your proof points? Where are your enterprise case studies?" All that sort of stuff. So, like, that's the, um, th- that's how that plays out, basically.
- HSHarry Stebbings
Yeah. Do you know what I find really challenging today is quite often I meet companies where actually their customer base is very horizontal, and what I mean by that is Asana, Notion-
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
... a- applicable for dentists and applicable for SaaS startups.
- DTDes Traynor
Yeah.
- HSHarry Stebbings
And, uh, from a product messaging standpoint, oh, fuck, it's such different messaging. How do you think about effective product marketing and messaging when approaching a horizontal customer base like that? 'Cause you have the same, I guess.
- DTDes Traynor
We have a version of it, for sure. Like, uh, it... I think Notion and Asana probably go broader again-
- HSHarry Stebbings
Yeah.
- DTDes Traynor
... in that people use them to plan weddings and shit like that. Like, but, like, uh, I think, um, the, the-
- HSHarry Stebbings
And shit, and shit and shit like that. I love it. (laughs)
- DTDes Traynor
(laughs) Uh, the, um, the standard answer you're gonna hear to this is gonna be some... "Well, have you considered a verticalized marketing play," right? Like, what that would look like is you pick your top 10 industries, and you nail the marketing for that specifically. So you say, like, "Notion is for dentists," or, "Notion is for software companies." And you pick the... Like, like, generally speaking, what you're looking for is industry times workflow. So, like, who do you do it for, and what do you do? So, like, in the case of Notion, y- y-... Notion can be, like, an intranet, it can be an externally hosted website, it can be... it can model workflows, it can be a project management or project planning tool, and it can be, like, a to-do list, and it can be a personal knowledge, uh, n- knowledge storage type tool as well, right? And maybe, like, four or five other things. Um, so you have those, like, say, 10 different ways you can use Notion, and then you have, like, who are the people who use Notion? And you ha-... And, like, in that world, you've got, you know, startups. You've got, like, uh, whatever, like, you know, personal productivity gurus. You've got, like, you know, uh, dentists. Whatever else you have. And then you, you're basically looking for, like, what are the most compelling sizable use cases that we, uh, can actually play out here, and how do we market them really, really well? And, uh, and I... The, the, the mother of this entire space for me was, um... Oh, what was that tool Atlassian bought? Um... Uh, the one with the, like, cards you can drag and drop around the place?
- HSHarry Stebbings
Oh, Trello.
- DTDes Traynor
Trello, yeah. So Tr- Trello was the extreme end of this, right? You know, like, Trello's goal was really to create a horizontalized productivity tool, and they really were trying to avoid getting stuck into any particular hole, uh, 'cause they were like, "We want people to use this for shopping lists, weddings, house renovations, s- pro- planning software products," and all that. But inevitably, like, the problem with most of those use cases is once you start to follow the money, you end up back in B2B SaaS land. Right? (laughs) Or at least B2B land anyway, right? There's not a lot of money selling software to wedding planners. There's a lot of money selling software to IBM. You know, so, um, so generally the, the money still tends to bring you home, and as a result, you end up saying, "We do our best work for other businesses, and we solve business problems. And here's the top three businesses we work in, and here's the top three use cases we solve." And then as you move further up market again, you'll end up playing with the Forresters and Gartners of the world, who are gonna say, "Hey, we're doing a productivity wave for, like, 2023, and where, what, what category would you like to be in?" So before you know it, you're, all of your desperate attempts to horizontalize yourself... When it, when it comes to marketing, you still need to pick a lane and say, "Here's what we are." Even if you're just saying it for one person, you still need to say it. Like, you can't be everything to everyone, 'cause no one will buy you. So whenever you're put in a moment, you're still gonna instantiate yourself in a specific, you know, uh, vertical times use case.
- HSHarry Stebbings
I'm so pleased you said there about, you know, bluntly, the move up market, 'cause I, I wanted to talk about this 'cause I see us so often making
- 35:50 – 39:11
When is the time to move upmarket?
- HSHarry Stebbings
mistakes with founders that I work with today. And it's like fundamentally, first, how do you advise founders on when is the right time to start thinking about moving up market? What are the signs that they should do it?
- DTDes Traynor
I think if, um... Like, it, it... D- this one kind of varies a bit, but generally speaking, uh, you have to look at, like, the, your successful customer growth and what's happening with your best customers. And that's the two variables you need to, you need to see. So if you think you just have loads of run room horizontally in the market, so you can just keep getting more and more customers like the ones you already have, and I mean exactly like them, uh, then I d-... A- a- and you don't have to change your product to do that, then I think you shouldn't move up market. You should just carry that growth out. Uh, because I think, like, you know, generally speaking, in all software, we all want the smallest possible product we could possibly have.
- HSHarry Stebbings
Mm-hmm.
- DTDes Traynor
Doesn't work out that way. Like, uh, (laughs) you're talking to somebody with, like, three different products across, like, three different use cases. But, um...... but, like, you know, generally speaking, y- w- i- if we could have our way, we'd all have just a piece of software that's just one line of code and it has, like, no bugs, and never at- never needs anything, only needs one engineer to maintain it, right? That's, like, the dream state. Uh, the only reason you add the second and third line of code is to get more customers.
- HSHarry Stebbings
Yeah.
- DTDes Traynor
And, uh, so if you can avoid having to have a massive product footprint, then you should. But generally speaking, you want growth. So if, for example, um, you find that, like, hey, we're not doing anything. We're kind of taking our hands off the wheel. We're still seeing, like, you know, three-digit percentage growth acro- uh, across for, like, loads of different people, all for the same sort of, uh, use case, and they're not coming up with really bizarre, different, uh, feature requests, then stay where you are. Absolutely stay where you are. Now, the actual decision point is if one of these two things is true, we can't keep growing horizontally 'cause they're asking us for specific features, like-
- HSHarry Stebbings
Yeah.
- DTDes Traynor
... the hotel customers all want a hotel booking feature, you know, or whatever, right? Uh, then we have to weigh up that work versus that market expansion against wha- what would happen if we solved the needs of our largest customers and the ones that are out of reach from them, and we weigh up the value of doing that work, which is possibly not as much work 'cause it might just be, like, adding roles, and permissions, and stuff like that onto your, uh, current platform. Uh, then you're looking at the ROI of two efforts and saying, "Which is easier? And also, which keeps our business as simple as possible?" And simplicity is really underrated in business in, like, in loads of ways. Honestly, I could rant about it for hours. But like, uh, but y- let's say your brand architecture just gets messier. If you had to launch 20 VC but also for soccer teams, it'd just be weird 'cause everybody would be like, "What's Harry about," right? Uh, it's easier to say you're going to do 20 VC, and you're going to do a different one for investors and a different one for founders. That's, uh, that's clean. That makes sense. That's on brand for you, you know? Um, so similarly, like, you have to think about, what does our br- what can our brand architecture support? And oftentimes, that might just be a move up market. The other variables you have to look at is, what's happening to our best customers? And one thing that happens to a lot of software companies that sell to software companies is that their best companies outgrow them really quickly because software companies all grow really fast, and that means you're going to see somebody just whistle through your target segment and come out the other side, and you'll be like, you'll be there going, "Wow, they used to be a customer of ours. I bet you they would have paid us millions if we still kinda kept them," and you were, like, four, you know, four roles, and permissions, and a Salesforce integration away from keeping them happy.
- HSHarry Stebbings
(sighs)
- DTDes Traynor
So
- 39:11 – 41:26
How to avoid feature creep
- DTDes Traynor
you have to kind of do all of this calculus against each other.
- HSHarry Stebbings
I, I, I'm so pleased you said about the importance of simplicity there 'cause feature creep on the product side is just the most dangerous thing, but also very common to see. How do you retain simplicity with scale and with growth of customer adoption as you think today as a product leader?
- DTDes Traynor
I mean, like, the short answer is you don't, in my opinion.
- HSHarry Stebbings
(laughs)
- DTDes Traynor
Uh, what you do is y- y- you fight as hard as possible, but you're gonna lose the fight, you know? Like, you're gonna, y- you're going to end up doing something 'cause it, you know, we have, like, you know, hundreds of people working at Intercom. They're not all removing features, (laughs) you know? Uh, so, like, the product is going to get more complicated. And, and I think one mistake that folks make is, um, because, like, oftentimes product decisions are made entirely within the product org or the R&D org, if you're so inclined, uh, they kind of forget about the ramifications everywhere else. Like, so, uh, as an example, every complex new feature we build has to get marketed by a marketer, and has to get sold by a salesperson, and supported by a support person. So you have to think about the total cost of ownership of that feature, not just how hard was it to build. Um, generally speaking, you're trying to find the highest leverage work, uh, which usually involves looking for, "How little can we do, and how much can we get from it?" And, uh, and, like, that's, so like, that's the forcing function of simplicity. And then for any given thing, y- someone will say, "Oh, if you just add, like, you know, a classic one for Intercom
- HSHarry Stebbings
(laughs)
- DTDes Traynor
... lore would be if you only added these four more reports, you'd also be a great analytics company," to which we've always said, "Yes, that is possibly true. I don't fully believe it's true, but if we did do that, then we'd also have a different problem. We'd also be a fucking analytics company, right?" Like, you know?
- HSHarry Stebbings
(laughs)
- DTDes Traynor
And that, and that is a whole other problem, which is, like, now we have a different brand. Now, we have a different whole, like, um, go-to-market message. Now we have, like, we have different needs for different types of, like, engineers, different big data storage challenges, and all that sort of stuff. So just thinking a- and, like, our sales reps need to know how to speak analytics and speak customer communications on the fly, and adapt, and all that. Like, e- it's so, the, the downstream ramifications of such an easy, incremental piece of work, uh, are really, really easy to underestimate. And like, so I just, you know, generally speaking, I, I think, like, if there's ever an opportunity for simplicity that isn't, like, uh, massively harmful to the growth to the business, I would always try to take it.
- HSHarry Stebbings
Do you agree with the notion, "Just
- 41:26 – 43:11
Should companies raise prices?
- HSHarry Stebbings
raise prices"? Mar- you know, Marc Andreessen's often said, on a billboard, "Raise prices." Do you agree with that? Dharmesh Shah from HubSpot on me, he showed the other day, he said, "No, it's goodwill to actually underprice your product in a lot of cases."
- DTDes Traynor
I think, uh, I saw a, like, I think, um, Marc Andreessen's point is just, is just un- like, unnecessarily blunt, and, uh, and I think Dharmesh's point is more, um, pointy. Uh, like it's, uh, it has substance in it. Like, you're always trying to capitalize on, uh, the value you deliver for customers, and you don't want to, like, uh, squeeze every last drop out of it, uh, for sure, and that's Dharmesh's point. At the same time, uh, I think there's a danger of, like, if you end up doing a lot of, like, like, so a hard adopter of Intercom, let's say somebody uses this for everything, we are their onboarding guide, their customer support. We're, like, how they, how they route sales leads to, like, uh, to their reps to close deals. We're how they do in-app feature adoption. We're how they launch things. We're, you know, and, like, we're their, also their knowledge base, and we're, like, sending SMSes and WhatsApps for them as well, right? You have to kind of like, you know, y- if you want to sustain a product that's that large a footprint, it needs to be paying you back in a way so sh- so you can reinvest in, and maintain the health of the product. Otherwise, you, you do end up in a world where, like, um, you basically can't afford to work on your product in a sense, right? So you have to kind, and, and, like, you know, and HubSpot are no stranger to a price increase either. Um, but I do think, like, the idea of, like, "Just raise prices," is silly. I think align price to value is the thing you have to do.... uh, and, and just make sure that you're, like, building the thing that you sell people on, and that when you sell them on it, that they're actually getting the value you're charging them for.
- HSHarry Stebbings
Uh, w- when we think about kind of the raising prices, moving into enterprise, a lot changes in the team structure, in
- 43:11 – 46:07
What changes with product when you move upmarket?
- HSHarry Stebbings
the kind of, uh, kind of resource allocation that's needed. In terms of the product, what, what changes with the product when you need to move up market?
- DTDes Traynor
There's a few big buckets that, um, are just immovable. Um, I'll kind of walk through them a little bit. One is just adaptability, like so making sure to
- NANarrator
(sighs)
- DTDes Traynor
... upate. Like our large enterprises don't just pick up products, like, randomly. They have like, oh, like they have an MSA they need you to sign. They have a procurement team that assesses you. You need to be like SOC 2, Type II, possibly HIPAA, possibly ISO 9000 compliant. Uh, you need to be able to do an, uh, a security review, and all that sort of stuff. So there's a whole piece around just adaptability, and there's other stuff like SKIM processing. So like, uh, so people, they, they might mandate that you have to be able to sign into the product through the Google, uh, through G Suite, as opposed to creating your own logins, and just loads of stuff like that, right? So that's all one big bucket called adaptability. Startups don't give a shit about any of that, but big companies absolutely mandate it. Another one is scalability, and I won't say much on it. Just sort of like you need to be able to meet their usage requirements, so if they want to send a million mails a minute, you need to be able to do that. And third one is justifiability. So like, you need to surface the data that proves that your product is delivering the value that they're paying for. So this is often... And there's, there's tiers to this. There's like generate your own reports, let them generate custom reports, all the way up to, let them dump all of your data into their data warehouse, or data lake house, or whatever they want to call it, like a snowflake or whatever, and get all the stuff over there, so that when they're reporting out on, on what value they got, they can do it for you. But that's all justifiability. And then the last one I talk about is interoperability. So you actually have to be a good citizen of their tech stack, so you can't just be like, "Intercom's here, delete everything else." They probably have 15 other tools that they use in conjunction with you to talk to, to their customers, or to manage customer conversations, or just the health of their customer base. And you need to, like, have a really good interoperability posture, meaning that you should be hydrating all the other data sources that would benefit from knowing what Intercom knows, and similarly, you should be sucking in data from them as well, to make sure that Intercom is the best Intercom it can be. And in doing so, you become like what they call, like, an improvement to their tech stack. So in general, we would say, like, uh, a support stack is better when Intercom is plugged into it. Everything gets better, not just Intercom. But y- interoperability, like, there's a whole world of, like, APIs and middleware that you have to consider as to how people do it. So they're, they're kind of like the big four, I think, that change. And like, none of them, just, just to note for your listeners, I didn't describe a single user-facing feature that you're gonna do any product marketing for, right? Like, you're never gonna have a sexy screenshot after Salesforce integration, or the new API calls. It's always like this behind the scenes stuff, that when people say, "Are you enterprise ready?" what they actually mean is all of that stuff, and people forget to market it. People forget to like, showcase that in the right places, because it's not visible. It, it's not something you can, like, do a great webinar on, or whatever.
- HSHarry Stebbings
So I think adaptability is one of the most exciting places to be investing today. Like, I invested in WorkOS, which obviously w-
- DTDes Traynor
Me too. Yeah.
- HSHarry Stebbings
Yeah. Great. P- perfect example. Uh, SecureFrame, which is obviously SOC 2.
- DTDes Traynor
Yeah.
- HSHarry Stebbings
Like,
- 46:07 – 49:38
Where are you excited about investing?
- HSHarry Stebbings
I think it's such a good space to be investing. It was Ophelia who said, "SAS, PLG," and it, it's all kind of saturated right now, honestly.
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
Um, her question was, "Where are you excited?"
- DTDes Traynor
Hm. (smacks lips) That is a good question. I, I, one area I've been having, like, some, I guess, uh ... Well, w- areas that get me excited is like, I think taking SAS to industries that don't see much of it s- is still exciting. Uh, so like, um-
- HSHarry Stebbings
Do you not worry about the long sale- Sorry, I didn't mean to interrupt, but I, I'm with you, and then I see the sales cycles for mining companies-
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
... and the customer education process-
- DTDes Traynor
Yeah, yeah.
- HSHarry Stebbings
... for car dealerships, and I'm like-
- DTDes Traynor
Yeah.
- HSHarry Stebbings
... "Fuck."
- DTDes Traynor
I, I think that is a problem, and I think that just needs to ... Like, that, that's a problem, and it, and it causes possibly a bit of boredom for me and you, because it's not as responsive as, like, launching on Product Hunt or whatever. I just think you need to bake that into, uh, you know, price that into your sort of considerations, which like, so, um, (smacks lips) like, uh, I've invested in a B2B SAS company for managing building construction product pro- uh, projects, right? And, um, it's going great, but definitely the long sale cycles, and the, like, random adoption pat- patterns and all that are, like, very weird to me. But the business is a monster, you know? So I think, like, uh, I think it's cool to see how SAS will ultimately transform these things. It's definitely way slower than like, "Hey, everyone's using, using this, like, new note-taking app," or whatever, where we all adopt it in three days, and we're all done talking about it in like four podcasts worth or whatever.
- HSHarry Stebbings
(laughs)
- DTDes Traynor
You know, it, it, it's different to that. Like, it'll take five years for like, uh, f- uh, for, in your example, like the car hire company or whatever. Like, it will take five full years for that company to realize the value of the software it built in year one, which is just very foreign to us, 'cause we just think, "Launch the thing already," you know?
- HSHarry Stebbings
Are there any s- are there any, like, decks to come across where you're like, "Ugh, no." Like, I get this, and i- it's so easy to do, but-
- DTDes Traynor
Yeah.
- HSHarry Stebbings
... say, recruitment. I'm like, "If I get another recruitment marketplace." (smacks lips)
- DTDes Traynor
Yeah. There's a few. I think, uh, the ones that I get most bored by, uh, anything that smacks of all your data in one place, I just, I just really don't care about, and especially if it's consumer. Like, uh, just in general, it's, it's such a, it's such a ... Like, no one actually has that problem.
- HSHarry Stebbings
(laughs)
- DTDes Traynor
Just engineers realized, "Oh, you could connect all these things into one place," and, and like, d- this is like the age-old joke about like, standards. Like, we love standards so much, that's why we keep inventing new ones. Like, and, uh, I just think, like, I, I think fundamentally, the product space, like, uh, whenever anyone's saying, "We're gonna centralize everything," I'm like, "It just sounds to me like you're gonna create yet another place for things to live." It doesn't sound like you're gonna solve the problem in any meaningful way. So that's one kind of meta pattern I see. I think another one where I just really get bored is like products that are actually just Google Docs. Uh, and by that I mean-... like, performance reviews as a product, and when you actually look at it, it's basically like, "Well, actually, at my last company, I had this really sweet template for doing a performance review. I asked what were your top three ambitions, your top three hopes. I asked for feedback," blah, blah, blah. "And now, I've turned all that into a B2B SaaS app where you have different text inputs for all of this." And I'm there going like, "What is the actual benefit of the structure that you're imposing onto content? Who benefits? Why does anyone care?" And then, also, if you're right, this is, like, copyable in, like, four weeks.
- HSHarry Stebbings
Yeah.
- DTDes Traynor
Uh, so, like, just generally, whenever people are, are turning ... Like, turning spreadsheets into SaaS apps has been a good idea forever. Turning glorified Google Docs into
- 49:38 – 51:03
Allergy to BS
- DTDes Traynor
SaaS apps I think has never been a good idea.
- HSHarry Stebbings
I, I, I love that phrasing. It's also a bit direct, to be honest, Des.
- DTDes Traynor
Yeah.
- HSHarry Stebbings
And when I spoke to Ophelia, when I spoke to Kira, and when I spoke to, uh, Matt-
- DTDes Traynor
Yeah.
- HSHarry Stebbings
... um, they all kind of told me about your allergy to BS. How do you communicate that and that blunt directness i- in a kind of graceful way? I haven't quite mastered this.
- DTDes Traynor
I don't ... Like, w- An area I struggle with is, uh, in, in general, i- is, like, uh, like, radical candor. I, I think I, I, I don't say firmly enough, like, what I actually think. What I ... But when I'm e- whenever I'm trying to correct someone's thinking or at least get them onto my side, I try to, like, uh, like, in the case of one of those startup, uh, products, I wouldn't just be like, "This is bullshit. Get it out of my face."
- HSHarry Stebbings
(laughs)
- DTDes Traynor
I'd be like, uh, I'd basically say, like, "Hey, the most successful startups I see, generally speaking, have many of the following characteristics, and here they are, and, and I'm ... When I look at your idea here, what I'm not seeing is, uh, any sort of moat, or I'm not seeing anything that's unique, or I'm not ..." You know, I'll, I'll, I'll try to get them on board with the, the sort of principles of my thinking, and then explain why this investment would, like, violate my thinking. And my goal is always that either they walk away saying, "You're full of shit, Des," which is totally fine, that's a great outcome, 'cause, like, they stood up to me, and they said, "I'm gonna walk away and do my own thing," or they agree to me because I convinced them, and that's a good outcome too, and then they kind of correct their idea. I don't mind either of those two. I, I ... A- anything in between is, is, like, not good, and
- 51:03 – 53:08
Biggest investment miss
- DTDes Traynor
I ... So I'll, I'll try to force it to one of those two outcomes, I guess.
- HSHarry Stebbings
Des, what's your-
- DTDes Traynor
That may be it, yeah.
- HSHarry Stebbings
What, what's your biggest investing miss, and did it alter how you think today?
- DTDes Traynor
(clicks tongue) I probably am more known for writing too many checks, so I'm probably more known from, uh, like, uh, sort of, like, t- t- too many bad checks as opposed to any ... I'm trying to think of what's ... Like, there's a few I couldn't get it together to do on time or did too late or, uh, or whatever, so Polleywork is one where I still think there's an interesting future ahead of them, um, and I, uh, I basically just couldn't get the paper worked together. Like, just I ... One t- o- one of the downsides of being an operator genuinely, like, as in somebody who has a job when you're trying to invest is you're just getting hit with, like, DocuSigns left, right, and center, or, like, due diligence things, or, like, oftentimes, it'll be like, "Hey, we have to form this other company, which is a special purpose vehicle to make this investment. I need you to sign these seven things." And, and all ... So that sort of stuff is wha- where more likely I'm, I'm, I'm likely to scupper because, in general, I'm, I'm probably more likely to have a go than not. Um, I'm trying to think if I've ever actually been like, "That was a total miss." There's a few I think will, uh, turn out to be a miss. There's a, there's a startup developer tool called Roadie that I should've invested in when I was given the first chance, and I think that will work out. Uh, Incident.io would be another one. Um, there's al- there's been ones where, because I invested in one area, in one product, I couldn't invest in another-
- HSHarry Stebbings
Mm-hmm.
- DTDes Traynor
... and the other one has been the right investment, if you know what I mean. Uh, so there's ones I've called wrong that way. Um, I'm trying to think if I ever said no to any- ... I mean, no, like ... Anything else, I forgive myself 'cause I didn't have the money at the time. Like, there was a chance to invest in SpaceX, but, like, I didn't have 100 grand, and that was the smallest check. And I, I'm just like, "Hey." Like, I probably should've borrowed that money, but, like, I didn't have it, so, like, c'est la vie, you know?
- HSHarry Stebbings
(laughs)
- DTDes Traynor
Uh, that would be like ... Tho- those are the ones I forgive myself on. Honestly, I expect to be back here in, like, five years' time saying, "Des, you've lost famously over a million dollars in startup investing."
- HSHarry Stebbings
(laughs)
- DTDes Traynor
"Tell me, what one did you get right?" (laughs)
- HSHarry Stebbings
Des, do you mind if we slightly run over?
- DTDes Traynor
Yeah, yeah. No problem.
- HSHarry Stebbings
I, okay, I'm just too inter- ... On the, on the startup checks there,
- 53:08 – 54:02
Consistency of check size
- HSHarry Stebbings
the thing I always advise new angels is consistency of check size. You do, do not pretend like you know more about one company than you do another. Know your check size and stick to it. Did you do that? Do you have consistency?
- DTDes Traynor
Uh, kind of. I ... The only thing I do is if I really believe I go like a little. Like, my check sizes might be, like, somewhere in, like, the 25K region unless I absolutely love the product, love the space, and I've just been blown away, in which case, I'll push for more, and I'll take what I can get. But, like, honestly, the nature of an, of an investor like me is, like, people see me as a jigsaw piece, like, uh, when it comes to check size and be like, "Hey, we have a gap of blah. That can go to Des or whatever." Um, I'm never like ... I, I know what it's like on the other side, so I'm never gonna be the guy constantly bullying my way in, going, "No, give me 300 grand," or whatever. Um, but so I'd say I have two sizes basically, normal, and I really think this is a monster. Uh, and I'd say I've only done, like, five of the latter category.
- 54:02 – 54:47
Do you do reserves?
- DTDes Traynor
- HSHarry Stebbings
I, I, I'm totally with you. Can I ask, do you do follow-ons? How do you think about reserves?
- DTDes Traynor
(sighs)
- HSHarry Stebbings
It was interesting. I, I, I interviewed Dharmesh Shah, and he said-
- DTDes Traynor
Never.
- HSHarry Stebbings
... "I don't ever do a founder meeting."
- DTDes Traynor
Yeah, yeah.
- HSHarry Stebbings
"It takes too long. I never do DD."
- DTDes Traynor
Yeah.
- HSHarry Stebbings
"I never do follow-ons. My three rules."
- DTDes Traynor
Yeah, yeah. I f- I follow closely. Uh, I, I try to avoid meetings unless, unless someone tells me like, "No, no, the dude will really sell you on the idea," or whatever. Um, so I, uh, I, I try not to do those. Uh, I definitely don't do a due diligence at all, but, like, but at the f- at the same time, I always caveat my check and say like, "I'm only doing this if there's a lead investor who is actually going to do due diligence," if you know what I mean. So, like, as in, "Don't consider this a commitment until you tell me that
- 54:47 – 59:47
Intersection of parenting and leadership
- DTDes Traynor
somebody is actually going to do the homework here. Like, prove to me the company exists," type thing.
- HSHarry Stebbings
I do wanna discuss one final element. You mentioned before having a newborn, and it's your second.
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
Children are such an impactful part of one's life. And you said before about the intersection of parenting and leadership. What did you mean by this intersection, and how do they come together?
- DTDes Traynor
I think there's a lot of things that you have to be good at for both. Um, that's the first thing I'd say. Uh, like, what you realize with a kid is, um, you have to, like, be their, uh, how would you say, their, their willpower. You have to be their discipline. And unlike yourself, like, let's say you're trying to obey a diet yourself, you have a very closed loop feedback mechanism there. Overeat, gain weight, e- eat less, lose weight, whatever, exercise, feel good, don't exercise, feel bad. Um, whereas when you're trying to, like, discipline a kid, uh, and not, not discipline, that's the wrong word, but when you're trying to, like, uh, raise a child, um, you're trying to say, "Eat healthy," but it doesn't actually affect you whether or not you do it. And in fact, the feedback mechanism, you'll find out over five years, uh, not in the next, like, five days, right? 'Cause it's not your body. Uh, so it requires you to have a lot of, like, care, and empathy, and compassion for something that isn't directly felt, like, physically by you, and you're trying to make that happen over, like, many years as opposed to, like, many days, or, like, any sort of better feedback thing. And if you're trying to lead a group of people in a business, there's a lot of similarity there in that, uh, you're trying to get everyone on the same page, and get them support, and have them understand the principles by which you're trying to push towards certain things. Uh, you're hoping that they're aligned, and you're hoping that, like, you know, that that, like, that, that alignment won't disappear once you leave the room or whatever. Um, and you're hoping that the payoff over many years will make them realize that actually, "Hey, that was actually, you know, he or she was looking out for me at the time." So that's, th- that's one whole category, which is just, uh, understanding, like, how to, um, communicate your best intent for them, for people, uh, withou- without, like, micromanaging, because you can't be there every second of your kid's life, 'cause you're not gonna... I mean, once they walk out the door, they're, they can do whatever they want, you know. Um, so, like, there's, th- there's a lot of that. The other area where I, I reflect on a lot is, um... It's a great blog post. I can't remember who wrote it, but, uh, somebody will augment, I'm sure. Uh, it's called being demanding and supportive. So, like, that is, you have to be both... O- of a child or h- of, of, like, uh, people who you work with. And I, and I really do mean work with. Like, you have to have this stance towards your peers as well. You have to be both... You have to, like, ask so much of them to make them realize their true potential, um, and that's the demanding side, but then you also have to be willing to support them should they ever struggle or ever bump into any barriers or whatever. And, uh, like, so you have to basically say, like, "I think you can actually change the world. I, I think you're one of the best principal engineers I've ever seen, and I actually think you, you represent... the products you build represent the future of this company. I need you to go and do this really hard technical thing for me." And, uh, and then off they go and do it. But if, but i- if they fail, which they may, you need to step in and say, "To be honest, that was beyond any of us. Like, it was a ridiculous effort, but you made a phenomenal effort at it, and, uh, and, look, uh, and I'm here to cover for you. Don't, don't think that this has been a bad outcome."
- HSHarry Stebbings
What, what if it wasn't b- beyond any of us? What if you should have been able to do it? I, I've been let down by people, by hires. I've thought more of them. Um, I think... I, I, I'm, I'm... I don't mean this arrogantly, I'm not smart, but I will fucking kill myself to get stuff done, and I, I don't always find that with people, and then-
- DTDes Traynor
Yeah.
- HSHarry Stebbings
... I feel let down.
- DTDes Traynor
Mm-hmm.
- HSHarry Stebbings
And it's not okay, actually, and I'm upset.
- DTDes Traynor
Yeah, I think that's... So, like, that's the other side of performance management, and I think in those cases, like, um, like, you know, when I engage the demanding but supportive mode, it's much more, like, pushing people to be their very best. It's rarer to try that with somebody who you have doubts about 'cause you're actually, you're trying to push them to perform to begin with.
- HSHarry Stebbings
Yeah.
- DTDes Traynor
Um, and, uh, and I think in those cases, you have to move to a slightly more structured type of conversation, which is, like... I, I mean structured in, not in the sense of, like, a PIP or anything, but I mean, when you're asking somebody to do something that you think they should be able to do, but you have suspicion that they might not, I think you need to outline, "Here's what I think needs to be done. Here's the sort of timeframe I think it needs to be done at. Here's the level of quality I think it needs to be done at. And here's the expectation. Like, I think this is really likely that we'll get this done. Do you agree?" And, uh, and they say yes or no. And if they say no, then you're just on a different page about their capability in a sense, or, like, or what's reasonable, so then they, you shouldn't be working with them. Um, but if they say yes, then the only other question is, like, "If any of that changes, let me know, because this is a really important piece of work. So if, if you have suspicion that the timeline is wrong, that the complexity is greater than we thought, that the quality bar is lower, you need to, like, let me know, because we need to correct this course quickly, 'cause you're working on something really
- 59:47 – 1:05:01
Lessons on hiring
- DTDes Traynor
important here." You know?
- HSHarry Stebbings
F- final one for a quick fire, promise. Um, I, I, I've made many hiring mistakes in my time. Um, (laughs) and not such a long time. Uh, but tell me, uh, what have been the biggest hiring mistakes you've made?
- DTDes Traynor
Probably, um, earlier in my career, just being blinded by the logo, I think was probably the biggest thing. Like, such and such a person worked at such and such a company, and you're... I- in your head, as a naive younger founder, it's hard to not to, like, autocomplete to, "Therefore, what happened to that company is going to happen to us because we just got their head of recruiting, or their head of people, or their head of marketing, or their head of sales." And I have to say it out there 'cause, uh, I didn't want to imply it was any particular role. Um, but that's probably the single biggest thing, is, like, assuming that because somebody worked there, they were responsible for anything. And I think even the greatest companies on Earth, and I really do mean this, uh, have a few people who aren't high on the causation index, if you know what I mean. Like, they're... Like, they happened to be in a great company during a period of greatness, but they didn't have their hand on the wheel. They weren't, like, uh, they weren't responsible for causing a lot of it. However, their LinkedIn looks like fire. You, you know what I mean? (laughs) Like, uh, like, they l- they look like, uh, an absolute superstar, and it's only really when you ask them to repeat the magic that you realize they were actually the magician's assistant. And-
- HSHarry Stebbings
So I think one of the biggest bullshit things is only hire A-team players. I don't know if you disagree with me here. I don't think there's enough A-team play-... If we're doing true A-team players, A-team players at scale, how many people are in Intercom right now?
- DTDes Traynor
1000.
- HSHarry Stebbings
Thou- yeah. 1000 A-team players-
- DTDes Traynor
... yeah.
- HSHarry Stebbings
I think the definition of A-team is a little bit skewed.
- DTDes Traynor
(laughs)
- HSHarry Stebbings
Like, I don't mean that rudely to you. I'm not saying to you, specifically.
- DTDes Traynor
Yeah.
- HSHarry Stebbings
But like, that doesn't work. An okay is sometimes good enough in certain roles.
- DTDes Traynor
I think there's sort of a few different things there. Um, one is, like, uh, it's not like... Hire for potential, not, like, for, uh, not for, uh, like, state, you know? Uh, like, when we hire somebody, if we hire like f- a fresh college graduate today at Intercom, they're not our best engineer, and I think everyone should get that. And by definition, their, like, current state is not A-team. They are... Like, the, the question is are they on a positive trajectory? Can they get there? Or, can they get to what some b- uh, companies call, like, the acceptable, acceptable, like, sort of final level? Like, so as in, if you want, if you join Intercom and it turns out, like, you end up being, like, our senior manager of podcasting or something (laughs) like that, right? Uh, like-
- HSHarry Stebbings
(claps once)
- DTDes Traynor
... the question is, like, are we okay with you staying there, or do we need you to become the director? Do we need you to become a VP? Because the person who holds that position, in succession planning, needs to be on a very positive, uh, rapid career trajectory. So you have to ask those questions. And then there are some areas where, yeah, like you don't, you actually literally can't have like nine people on a team all thinking they're going to be the manager-
- HSHarry Stebbings
Yeah.
- DTDes Traynor
... because then eight of them are gonna quit. So like y- y- you need to kind of like, so you're always trying to fuse youths, like I said, not youths, like early in their career with like mid-stage career or late-stage career. You're trying to fuse like a, like a relative ambition to where they are in their career at the moment, actual capability. Like, we actually have experts who are like, who are superstars, like, who are whatever, I don't know what you want to call them, but like A+ in your analogy or whatever. Um, and you need all, like, uh, the ingredients of a team is not, like, just a load of people all walking around telling each other they're the best. Like, you actually need a mix. And people come to companies to learn, and by definition, that means they're not the best. They believe they can get better. So, like, I think it, there's a lot of, like, uh, nonsense behind it, like A's hire A's, B's hire C's, don't only hire A's, blah, blah, blah. I, but I, I, I, uh, I wouldn't go as far, maybe, as you and say, like, like, we are always gonna go out to market looking for, like, the best person you can get in a position. Um, but there, there, there's times when you operate relative best and when you operate global best. And the chances of you operating the globe, uh, finding the globally best person is pretty slim. There are times when it's worth the effort. Uh, but relative best meaning we're gonna bring somebody in who's gonna be at the top of the org, who's gonna set a new standard for us. There's time, you, you, you probably pull that lever off a lot more.
Episode duration: 1:13:11
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