Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Intercom Founder, Eoghan McCabe on How To Deal with the Weight of Expectation, Having Your Identity Tied To Your Company, How To Be Your Authentic Self Even with Stakeholders & Why There Are No Rules About this episode Eoghan McCabe is a technology entrepreneur. He's started a number of companies, the most notable of which is Intercom, the conversational relationship platform. He was CEO of Intercom for nearly 10 years, during which he grew the company to hundreds of millions in annual revenue, nearly 700 employees, and raised nearly $250M from the likes of Kleiner Perkins, Index, Bessemer, and ICONIQ. He's also invested in dozens of companies including Stripe, Figma, SuperHuman, and Coda. In the summer of 2020 he moved to the role of Chairman of Intercom. In Today’s Episode You Will Learn: 1.) How Eoghan made his way into the world of startups from Ireland and came to build one of the Valley's greats with Intercom? 2.) How does Eoghan thinking about living and thriving with a chip on one's shoulder? What does Eoghan advise in terms of one's search for their true selves? What were his biggest learnings in his search? What does Eoghan advise people who maybe feel they have lost themselves? 3.) Having been CEO of a $Bn company for close to 10 years, how does Eoghan think about dealing with the weight of expectation placed on shoulders? How did he manage it? How does he think about his identity being so tied to his company? 4.) In terms of being one's authentic self, how can one achieve this while also respecting their stakeholders who may hold different views? How does Eoghan think about being an authentic leader vs bowing down to the demands of your team? What is the right balance? 5.) Why does Eoghan think that vision can actually be limiting? How does Eoghan think about stress testing one's vision and ambition? What adversity from early VCs did Eoghan have to fight against? How does Eoghan encourage dissent and debate within his teams? Items Mentioned In Today’s Show: Eoghan’s Fave Book: Breathe: simple breathing techniques for a calmer, happier life As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? So today I have a guest returning to the hot seat here on the 20 minute VC. Our first episode was recorded over four years ago and so much has changed since then. And so with that, I'm thrilled to welcome back to the hot seat Owen McCabe, a technology entrepreneur who has started a number of companies, the most notable of which, Intercom, the conversational relationship platform. He was CEO of Intercom for nearly 10 years, during which he grew the company to hundreds of millions of dollars in revenue, nearly 700 employees and raised nearly $250 million from the likes of Kleiner Perkins, Index, Bessemer and Iconic. He's also invested in dozens of companies, including Stripe, Figma, Superhuman and Coda. In the summer of 2020, he moved to the role of chairman of Intercom and I do also want to say a huge thank you to Anna Khan at CRV,
0:41 Harry Stebbings? Abhijit at Zero Down, Kieran Lee at Intercom and Mamuna Kleiner for providing some fantastic question suggestions today. I really do so appreciate that. But before we move into the show today, I want to take a moment to mention HelloSign, a great example of a company that found success in building a product focused on user experience. HelloSign is an effortless e-signature solution used by millions to securely send and request legally valid digital signatures and agreements. They raised a total of $16 million in funding and recently got acquired by Dropbox for an impressive $230 million. Check out hellosign.com/20vc to join the thousands of companies and founders who value fast, secure and simple e-signatures. And if HelloSign helps you sign that term sheet, you need to get the term sheet in the first place.
1:25 Harry Stebbings? And I want to give a mention to Draper Esprit, a publicly listed VC fund that invests in high-growth European tech companies with global ambitions. Their portfolio includes companies like Revolut, UiPath, Kazoo, Graphcore and many other top European companies. Draper Esprit writes checks of USD 5 to 50 million dollars, focusing on sectors like consumer, fintech, health tech, deep tech, enterprise and SaaS. And their investment team has an incredible depth of experience, both as operators and investors, that helps businesses scale globally. If that sounds like the sort of investor you want to work with, get in touch with them at draperesprit.com. That's D R A P E R E S P R I T dot com. And last but by no means least, if you don't have a SOC 2 report, you aren't going to be able to sell to major customers.
2:10 Harry Stebbings? Secureframe helps startups get and maintain SOC 2 and ISO 27001 compliance in as little as two weeks. Join companies like Stream, Hasura, Benner Pass and unlock more sales with Secureframe. 20 VC listeners get 10% off at secureframe.com/20vc. That's secureframe.com/20vc. But that is enough of my dulcet tones. So now I'm very excited to hand over to Owen McCabe, Chairman at Intercom.
2:42 Speaker 01 You have now arrived at your destination.
2:45 Harry Stebbings? Owen, it is such a joy to have you on the show again. It's been a very, very busy few years since we last on the show, but thank you so much for joining me again today.
2:52 Speaker 02 Yeah, my pleasure. A lot going on for you and me both, as we discussed, you're a VC now. Congratulations.
2:56 Harry Stebbings? Thank you so much. Life is suddenly a little bit busier, but I do want to kick off with some context. And so for those that missed our first episode, how did you make your way from Ireland into the world of startups? And come to found one of the valley's greatest in the last decade with Intercom?
3:08 Speaker 02 Story like so many others, young boy has big dreams, chip on his shoulder, sets out to prove himself. I don't know if there's a lot more to it than that. I was always passionate about building and creating and so excited about the promise of the internet for creativity and connection and commerce. And with Intercom, I saw an opportunity to help online businesses just more easily and effectively connect with their customers and have a lot more fun doing it too. So it was what Intercom was all about originally and still is today. Our mission was to make internet business personal and we made this little messenger and then bots that let these online companies and their customers really get to know each other and get their work done.
3:38 Harry Stebbings? Can I ask you, Owen, I have a big chip on my shoulder and with every stage, I think it will go away. Do you know what I mean? It's like, I always wanted to be a VC and I thought I'll lose the chip on the shoulder when I become a VC. And then I'll lose the chip on my shoulder when I have my own fund. And with every stage, the chip just moves further and further. And so now it's like, I'm not a good enough board member and I really feel that kind of chip. Would you say you still have a chip on your shoulder today? And how do you think about the relationship with that chip on the shoulder?
4:00 Speaker 02 It's a really good question. What do we mean by chip on your shoulder? It means you think there's something lacking in you. It's a lack of self-love. It's a sense that you're not good enough and that you need to possess or achieve something to be lovable or popular or safe or whatever it is. Often a product of our nurture and conditioning and the environment we grew up in. The experiences we had, one thing we do to medicate that is we try and attain these external things. I don't know, is it money or status or achieve something to prove yourself? And the lesson, the trite and cliche lesson is that we find out that that's not what we needed at all. That everything we needed was within us, but you kind of have to go that journey. You kind of have to prove yourself wrong before you can do the harder work.
4:41 Speaker 02 And so, yes, for me, having built a super successful business, bill a dollar company, hundreds of millions in revenue, helped me feel good. But whatever little lacking thing is there on the inside is still present. And really what it's taken for me to chip away at that, as it were, is actually to do the harder work, the internal work, the go on that inward journey. Sometimes it's a spiritual journey to really get to know what you need and develop that love and respect and appreciation for who you are.
5:05 Harry Stebbings? Sorry, this is going totally off schedule. I actually thought, I think the challenge to me is like, I want to embrace that inward journey and I want to embrace that spiritual journey. I think the truth is I I've kind of so lost myself in the pursuit of what I'm doing. And in the just continuous, you said before the show about two thousand seven hundred episodes, that's a pure grind five years. That kind of you look into the abyss and you kind of don't know what's looking back at you. How do you think about that kind of spiritual journey and that inward search? When maybe you've kind of lost yourself a little bit.
5:34 Speaker 02 Well, Harry, you're baby still, you're still in act one of your own journey. And so you've got many fun years to go to lose yourself and realize that that's not going to make you whatever it is you want to be, happy, whole. You talk about losing yourself, it's such an interesting way to put it. But what happens is is that we create these ego identities, these little images and ideals for who we want to be. They're usually built off, I mean, they're always built off things we see in the world. We're inspired by heroes and icons. We see other people doing some certain things and we imagine with ourselves that they have what we want and need. That's an example of losing yourself. That's why I love the way you phrase that. You lose yourself because really you're modeling your life and identity after someone else, something else. The next stage is to realize that that's not the answer. Then you must go on the journey to ask yourself, who am I?
6:18 Speaker 02 You need to find yourself all over again, or maybe you need to discover yourself for the first time. Who was it that said that man has two lives? One that starts the day he's born and the other that starts the day he gets to learn his purpose. And so that moment. Getting to know you and your purpose, your mission, your place in the world, that won't come from the process of losing yourself. It'll be the opposite thing. It'll be the looking inward. We can talk about that if you wish, but it's a very different journey than trying to build status and career and find external validation and obtain material things, et cetera.
6:45 Harry Stebbings? Can I ask, in terms of like belonging and a sense of belonging, I think so many challenges come from being so attached in terms of identity to your business. The twenty minute VC is entirely me. It's been my whole adult life, as you kindly suggested about my youth. But like for you especially, you know, you were CEO of Inscom for many years and then making the transition to chairman today. Obviously, you're not as operationally involved as you are a CEO, daily, daily grinding twenty four hours a day. Was that a challenge for you in kind of detaching your identity from individual and company?
7:12 Speaker 02 Of course. These identities that we build for ourselves, this armour, these images, they're a place of comfort and safety and we latch on to them. They're everything to us. We've worked so hard because we believe that they are the thing we need, that they are us. We believe it so strongly that we will answer questions by saying things like, oh, I'm a founder, I'm a tech guy, I am a VC, and you're not. You're so much more than that. You're Harry. And that's a big risk and a big danger, just getting stuck on to and associated with these images that then become limiting. Imagine what else you could do with your life. I'm not hating on VC. I think you're gonna make a wonderful venture capitalist and I think you're gonna have a lot of fun doing it too, but you can also do so many more things. You are so much more than that. There have been so many VCs in the world. What else could you become?
7:57 Speaker 02 Maybe you can become truly your own thing. Maybe you can become something truly unique. But if for the rest of your life or for as long as you say, I am a VC, then that's all you're gonna be. So for me, absolutely, yes. When I thought I was a CEO, I was trapped by that, even though I knew I had so many more things I wanted to do with my life and ways I want to invest my energy and different missions and adventures. And I had known that for years. It was a long process to be able to shed that outer protective layer and kind of look that fragile ego in the face and say, you've been a great CEO, but you're more than just a CEO. So it's scary, but it's so rewarding.
8:32 Harry Stebbings? Can I ask, I think in terms of that title of CEO and, you know, it comes with this real weight of expectation and then especially with every subsequent funding round and the more and more millions that are poured into the company and the bigger it grows, frankly. The big thing that I always find is like the weight of expectation that I place on myself is incredibly high. And then also bluntly, that I think a lot of people very kindly have placed on me, which I'm very grateful for, but there's just this real weight of expectation I feel on my back. How did you deal with the weight of expectation on your back?
8:57 Speaker 02 Probably the short, pithy answer is not very well. I took a little bit of an arrogant approach to this, in fact. And I felt those who invested in us were fortunate to have the opportunity of our hard work and labour and creativity. And I kind of think that, that doesn't mean that I'm not really grateful for the big bets that people have made on us. And some have made bigger bets than others, especially the early stage folks. But there's a lot of money out there in the world, but there's only a very limited supply of creative, unique humans who are going to sacrifice their one short life and their youth and so much other opportunity on behalf of that money. So I didn't really feel expectation in that respect. I felt expectation from myself. We talked about that chip on your shoulder. Anyone who has a chip on their shoulder, which is essentially, for me, is every entrepreneur I've met. Like I said, the chip comes from an inherent belief that they are not enough.
9:42 Speaker 02 They are not whole or valid without this thing. They are not lovable, people will not like them, or whatever it is. And that is so wazzy. Think about that belief, I am not enough. Think about that belief. That carries so much strength and power and pervades your every breath. That can't compare to whatever expectations that some financier might have for some slaver of their multiple funds. That was the hardest part for me personally.
10:07 Harry Stebbings? Can I ask, a lot of what we're discussing, it's, the thing I love about it is to say it's truth and it's kind of vulnerability. And I think there's so much kind of chest pounding and chest beating in this industry that really I just get quite tired of. I think the question for me is, when we think about this vulnerability with its relationship to leadership, how do you think about the balance of kind of real leadership? And then pandering to employees and being that kind of champion at all times? What's the right balance?
10:29 Speaker 02 Well, there's many different things in that. I don't think about this in terms of balance. I'm pretty absolute on this point. I think that real leadership equates to a deep connection with your purpose and your values. And any deviation from that makes for a bad leader and poor leadership. I understand leaders today, they're in a precarious position when really your very talented employees can work anywhere. The temptation to say what they want you to say and give them what they want is very real, but it's not sustainable. It's not enduring and it's a slippery slope. And I see a lot of leaders today, especially in this age of extreme social activism. There's a lot of pain out there in the world and a lot of beautiful ideas from people who want to help and stop that pain.
11:10 Speaker 02 But it results in leaders standing up for causes that everyone knows they care nothing about. They've never spoken on the topic about before. They've never acted in any way that might demonstrate that they have even thought about these issues. And now, all of a sudden, it's so, so important to them. It's just so toxic to their position as a leader. It loses them so much trust and respect and does no favors to the causes either, whatever the cause may be. If there's an issue you care about, roll your sleeves up and do something about it. Not just tweeting or saying things to your employees that you think they want to hear. If you care about a topic, do something about it. If you don't, be real also. And for sure, you'll upset some individuals and they may leave and go to companies that better represent their views and values.
11:55 Speaker 02 But there will be so many more who will deeply respect you for being real and authentic and vulnerable. And the trust that you can build from doing so is priceless. So it's a sticky topic for sure, but I think anything but doing so is pandering and is not real leadership.
12:10 Harry Stebbings? I totally agree with you in terms of really kind of standing up for what you believe in and being direct with it. I think the challenge that I have is like, everyone has stakeholders that they bow down to and kiss the ring to in certain respects. It could be your VCs, it could be your board members, for me, it's LPs and founders. And so like, that very much holds me back. I mean, I guess the question is like, to what extent do you then think about the balance between being true to yourself and coming out with what you actually believe? Where I have certainly very strong beliefs on things. Actually, I don't say any of them because I'm concerned about how LPs perceive it and how other VCs perceive it. How do you think about that balance of kind of being cuckolded into not saying something because of stakeholders?
12:45 Speaker 02 It's easier said than done. My co-founder Des used to say discretion is the greater part of valor. That was a long time ago in a different context. And I think more broadly that refers to choosing your battles. And I think that there is skill in choosing your battles, just because you disagree with a certain topic or you have an opinion. Does not mean that you need to wade in on it and let the world know. It doesn't mean that you have to and the world doesn't deserve that of you. And quite frankly, without that discretion, you can just cause a lot of trouble for yourself. Doing that does not mean you're being inauthentic. To you, it just means you're setting your priorities straight. But therein lies the real challenge for those who are values driven and who have strong ideals. And I think that deciding when to speak and when to not speak is very different from kissing the ring.
13:26 Speaker 02 And I would say that you will be most respected when you speak the truth to your stakeholders, whoever they are, even when the truth is somewhat difficult. It's the only way to build real trust and respect, and they'll appreciate you so much more for it. In any professional climates and society, there tends to be a lot of transactional behavior and people aren't as authentic as you might wish. And so there's ass kissing and ring kissing and whatnot. But everyone knows the difference between that and authenticity. And the small number of people who are able to skillfully and in a kind loving way and in a respectful fashion, really be true to them. They are the standout individuals that those stakeholders want to be around and bet on and invest in. So it's the next frontier. It's the next step up.
14:10 Speaker 02 A lot of people pride themselves in their ability to kiss the ring. And they think that their great skill and being able to make everyone like them is a tremendous benefit to them. But the degree to which they're truly liked is actually relatively shallow. And the people who are really beloved are not those who kiss the ring, but those who are themselves. Again, that's the next challenge. That's the next frontier and it feels good and delivers great benefits.
14:31 Harry Stebbings? It makes me think of something that we've actually said before, which is about kind of questioning the rules of the game there in terms of kind of sticking true to your beliefs versus maybe conventional merit. A question that I have is like, how do you think about questioning the rules of the game? When to do it, if there are rules and how are you thinking about that?
14:45 Speaker 02 Yeah, I mean, I don't believe that there are any rules in work and life. I have always taken a healthy approach to any endeavor where I try and question all the assumptions. Part of that is my own nature in that there's a part of me that wants to be a troublemaker and a contrarian. That may be the part that has a chip on his shoulder. But regardless, any endeavor I face into, I ask, how can we do things differently here? And it's the different and it's the new and unique that gets all the attention. It's where the value floods to. It's what the talent wants to be around. It's what the money wants to invest in. The mainstream and the masses, the top of the bell curve, that's old news. The leading cutting edge, things that are different, that's where the real magic happens. Nations are changed and culture and trends are set. So for me and my story, a lot of the things that were weird and novel at the time are now pretty mainstream.
15:30 Speaker 02 Silly little things like when I was raising our seed round in twenty eleven, I was told, and all the way into twenty thirteen, actually, when I was raising our series A. I was told you cannot build a hundred million dollar software business selling to SMB. Can't do it. You can't reach these people. They won't pay enough. They won't retain. Matter of fact, I was told by really smart people who were way more experienced than I and seemed a lot more intelligent than I thought I was. And I found their arguments convincing, but ultimately not convincing enough for them to change my mind. And it just turned out to not be true. We built a hundred million dollar business with SMB. Anyone who was in SMB was really just slightly larger. There was really no enterprise customers there and there are very few today. And so did so many others. Mailchimp is another great example. Shopify, wonderful example. I mean, there's dozens now.
16:11 Speaker 02 So that was just an example of a kind of a well-regarded rule that you cannot build a hundred million dollar business selling to small companies. It was just a fact. I was just told time and time again, buy VCs. Sorry, bud. Here's the facts. And I didn't like that fact and it didn't feel right to me and I didn't want to go that way. And I think that there was a little F you piece in me that's like, ah, I'm actually going to show you around. I'm going to really enjoy it. So that's just one tiny example and it's not very interesting now because we all know that it's true that you can build multi-billion dollar businesses selling to small companies. We know that now. So I'm just a big advocate for just questioning everything. And that obviously is a big strategic one, but there's like little facets, little things around the edges, how you employ people and work together and all of it. Question everything. For me, I find it just so much more fun.
16:51 Speaker 02 Rip up the rules, surprise people that agree to what you can inspire and ignite imagination and make people so proud to be part of a company that is different is quite shocking, quite shocking. We hired some of the best people in the industry and I think a big part of that was that after interviewing all the other great companies out there, we were the weirdos and they wanted that. They wanted to be part of something different. It just was more interesting. It would keep them awake and come into the office on time in the morning. So, I don't know, I'm the biggest advocate for just ripping up and ignoring and breaking all the rules as much as you can.
17:20 Harry Stebbings? When you have a culture that is as questioning of everything is encouraging of dissent, does that not actually slow down processes, make for inefficiency, too much time debating and a lack of execution? How do you think about like the balance between extreme execution and being very ruthless? Terms of meeting goals and targets, but also having that plastic mindset that does question everything. Are they not kind of paradoxical?
17:40 Speaker 02 Maybe on the face of it, I think any Intercom employees listening to this will know that there's a difference between my hyperbole and the facts on the ground, which is that we question everything, but we have structure and rigor and process. And this doesn't mean, as much as I advocate ripping up as much things as possible, doesn't mean reinventing the wheel. You need to know what components actually matter, what are strategic, what will make a difference, what will define you. There's just so much work that you need to do that actually will not define you. So knowing the difference is actually the fine art of creativity and business building. But all that to say that the strategic components of our business, we try to do many different things and we try to break the rules. But at the same time, we had phenomenal structure in the business and have today at levels that we didn't even see a couple of years ago.
18:23 Speaker 02 There are very structured goals and hierarchies and aggressive targets and KPIs and Intercom is an execution machine. And so I wouldn't want to suggest that I'm advocating for kind of anarchy and madness or believe in anything. But but for your strategic leaders and the people who actually are going to decide how to make a difference in the world, they're the ones that really need to think outside the box.
18:40 Harry Stebbings? Can I ask, do you love that? I think we're kind of relatively similar minds in certain respects. And I honestly just, I freaking hate process. I mean, it kills me because, you know, I never log any note. I don't take notes. I mean, math, but me, I mean, fuck all that. So I mean, I suck with process, but I'm great at zero to one. So we're getting it all done, great. And then we get to a size and I'm like, ah, I prefer the creative first few stages. Is that the same as you? And do you enjoy that scaling into process?
19:08 Speaker 02 I don't know if I have a simple answer. I think there's a lot that's similar between you and I. I do get pretty tired of the minutia of process that's not my forte. That said, it can be super fun to be creative on a big scale when you have hundreds of engineers and teams of brilliant designers and marketers at your disposal. Ripping up the rules with that weight behind you, it can be thrilling. The art again is to weave the creativity and innovation in with the process. And for me, what that looked like was partnering with our COO Karen, who we made CEO this year. And Karen was able to help deliver. For a substantial amount of process around our creativity. So I don't have any smart answers there for how you do that well.
19:51 Speaker 02 But to answer your actual question, I think we're quite similar. And yet, the one thing I'll say is that it can be really fun to be crazy at scale too.
19:58 Harry Stebbings? Yeah, I I totally see that. And I think you would probably just much better, good looking and younger looking. That's the only difference here. I do have one final thing that I have to start you on before the quick fire. It's vision. So I think vision, we will say about vision in ventures, like, oh, I want to hear the founder's vision and oh, isn't that wonderful how big they're thinking. I think vision is actually one of the most dangerous things you can have in certain respects, because I had a vision. My vision was to be an associate at Balderton Capital in London, and I'm probably gonna have to edit this out because they could hear it. It sounds really derogatory, but that was like the end goal for me five years ago when I started. Like now, I would never have expected to be where I am in my vision. And if I had been so constrained to my vision, it would have just actually restrained me, actually. How do you think about the benefits of vision? And do you not think that it can actually constrain you?
20:40 Harry Stebbings? Would you in Ireland ever have thought when you started, we're gonna be one of the valley's biggest companies and we're gonna be worth multi billions of dollars? Do you see what I mean?
20:47 Speaker 02 Yes, I mean, vision happens whether you like it or not. Vision is just how you think about the future. We give it a grander name like a vision, because in our industry, we're all about achieving big, great, audacious, bold and no less than world changing things. But vision comes in all shapes and sizes. I think what you're really getting at is that our potential for accomplishment is massively determined by the scale of our thinking. And that was a big lesson for me. I'm pretty sure that all other things being equal, if I was able to go back in time and starting to come again. By this stage, it probably would be ten exercise only because I now know that I can think bigger and that simply doing so gives you just so many more benefits. You take bigger bites out of the apples as you go along. You don't limit yourself. You don't hold back in the face of fear. You tell a larger story to bring in more talented people and point them in a bigger direction.
21:31 Speaker 02 Like one of the things I've been saying recently, and I think it's true, but I kind of need to put my money where my mouth is if I really want to be able to say this. But I think that building a, I'll just make this up if we're gonna use this criteria, building a fifty billion dollar company. I don't think is substantially harder than building a one billion dollar company, quite frankly, within say some sort of similar timelines. I really think that for talented, smart people, ambition and the size of your Vision is the key determining factor and anyone who's built a much larger business than I might like to say that that's a bunch of bullshit. But I'm just not convinced by that. I think it's shocking the degree to which our ambition and our vision determines outcome. You need to take that vision journey to find out. You need to start taking small bites and sometimes you realize that you could have taken one bigger and you stumble your way through it.
22:15 Speaker 02 I think sometimes arrogance goes a long way as long as it doesn't get you in trouble. A lot of people who've done things like me, they have some internal confidence that actually they didn't have a right to have. And hopefully the self-awareness they build over the years will take the rough edges off that and the arrogance will go, but their essential internal belief can stay. So it's a very, very long answer to your question and all I'm really trying to say is that the scale of your thinking is everything. Just think bigger, bigger, bigger, bigger. Most people I come across, even the greatest companies I've had the pleasure of investing in, I think they're still thinking too small.
22:46 Harry Stebbings? Sorry, I've got to ask because it's something that me and one of my closest friends who's also another VC think about a lot. It's like, when is just too big? Like when is like actually the LPs are going to look at the fund size and go fuck off. Not happening, boys. When is that balance between audacious, ambitious, great and like, well, guys, too much, too soon?
23:05 Speaker 02 The answer is in the outcome. Those who had the big ambitions and pulled it off, well, it turns out that they weren't thinking too big. Those that did and didn't, they were. I don't think there's any answer, but I don't think the scale of their ambition was the problem. I think it was their ability to meet that and to execute. And here's the deal. I've never come across someone who I thought they were thinking too big, who I also thought could execute really, really well at a tenth of that scale. Usually people I think are thinking too big, I just don't think they're a good fit for business or for entrepreneurship or for whatever endeavor they were embarking upon. It was the wrong thing for them. They'd be brilliant at something else, but the very fact that they were unconvincing in their narrative, I think is just more indicative of the fact that they're just disconnected from reality. Does that make any sense?
23:47 Speaker 02 It's not that anyone thinks too big, it's that some people think wrong. But what I'm saying is within the spectrum and scope of people who are smart and capable and creative and will make great entrepreneurs or creatives within the scope of those very fortunate lucky people, they tend. And to still think too small.
24:05 Harry Stebbings? No, I think I totally understand what you're saying and I agree with you in terms of kind of the binariness of the outcome, which is like it's all.
24:10 Speaker 02 Exactly.
24:11 Harry Stebbings? I do want to move into my favourite though, which is a quick fire round. So I say a short statement and as you remember, you give me your immediate thoughts in about sixty seconds. Are you ready to rock and roll?
24:19 Speaker 02 Let's do it.
24:20 Harry Stebbings? I really need to read more in Covid quarantine. What's the favourite book and why?
24:24 Speaker 02 I don't have a favourite book at all, but I'll tell you what I'm reading right now. It's called Breathe and it will convince you that you have been breathing wrong your whole life.
24:34 Harry Stebbings? And that's enjoyable to read.
24:35 Speaker 02 Yeah, I've already changed the way I breathe and it actually has a big impact. So I can't say more if we're gonna make this a quick fire round, but please read the book, breathe.
24:43 Harry Stebbings? Done. I will absolutely. Tell me, what would you most like to change about the value tech scene?
24:47 Speaker 02 I think just a little more love and a little less judgment. A little more open mindedness would go a long way.
24:52 Harry Stebbings? If you were a cocktail, what cocktail would you be, Owen?
24:54 Speaker 02 It's a bit basic. I like mezcal margaritas and I think that works for me because it's kind of approachable to everyone. It's got something for everyone, but it's also got a little twist with the mezcal. It's a little off centre. It's a little weird. So I'll give you mezcal margarita.
25:07 Harry Stebbings? I like that. That's a good one and I love a mezcal. So a good choice. Tell me, why do you love the Snapchat vending machine marketing campaign so much?
25:14 Speaker 02 I just love that they decided to be weird. There's just very few companies in the digital space that think outside digital. And they said, screw it, we're gonna play in a game that is not our game. Anyone who does that, I have so much admiration for. Just deciding to play in a field that's not yours, that you don't belong in. More power to you.
25:32 Harry Stebbings? Tell me, I love this one actually. Which angel has done the most to help build Intercom and how so?
25:36 Speaker 02 I think it's Bistone, who's one of the Twitter founders invested in us early on. And the reason he was so helpful was that for a young lad, I was twenty six when I started Intercom and moved to San Francisco. For a young lad in this big industry who really thought very little of himself, to have someone so accomplished, simply give you the time of day and treat you like you're important, like he always did, boosted my confidence no end. So that's my answer, Bistone.
25:59 Harry Stebbings? I love it and I think this is awesome. But tell me, what is it your biggest business accomplishment?
26:03 Speaker 02 We've talked about it. It's building a multi-billion dollar, many hundreds of millions of dollars in revenue business my way. Doing it in a silly, playful, creative, loving fashion that no one did before by ripping up the. Rules and figuring out that that works too.
26:16 Harry Stebbings? Tell me, how do you feel about Elon Musk? And I was seated that question by a mutual friend.
26:21 Speaker 02 I really admire the guy. He's no less than my hero these days. Steve Jobs used to be my hero. I would call Elon Musk my hero now. He's so authentically him and so deeply connected to his purpose. And not afraid to show up in the world that makes sense to him and is aligned with his values. And he's having fun doing it too. Trust me that most CEOs out there look at his Twitter and just wish they could have as much fun as he does.
26:44 Harry Stebbings? I totally agree with you. Tell me, best board member you've worked with and why?
26:48 Speaker 02 Such a dangerous question. Hopefully, none of them ever listen to this, even though I know you've got a broad listenership. I loved working with Ilya Fushman. He's with Kleiner Perkins these days. Ilya was always just real. I'm a stickler for integrity and authenticity. And Ilya was what he was and is what he is. And there was no games. He wasn't hard to figure out and I admire that so much.
27:07 Harry Stebbings? I love it. I love Iliati. I think Iliam and Muno, awesome team. Tell me, final one. Next five years for you and for Intercom, what do we have in store, Owen?
27:14 Speaker 02 I mean, Intercom's the easy one because we're on a trajectory, a path. You just extrapolate into the future. We continue to dominate the space of customer communications and no less than revolutionize how online business is done. We're starting to invest in customer support now. And so we're bringing all our innovation, like messengers and bots, to the masses and increasingly bigger businesses. So you'll see that happen at ever greater scale, especially in the next few years. For me personally, let's wait and see. Maybe you'll have me back in five years and I'll tell you the story, but I want to have some fun. I want to play and be creative. I have a lot of businesses and different ideas still in me. And there's different things I've been thinking about for some time. So I'm actively working on a couple of ideas. But whatever I do, I hope it's silly, fun, playful, full of love. And yeah, let's see.
27:55 Harry Stebbings? And has Harry as an investor. I think that's a totally good. Listen, man, thank you so much for doing this. I've so enjoyed it and I really appreciate you coming back.
28:03 Speaker 02 Yeah, it was really fun. Thank you very, very much.
28:07 Harry Stebbings? I mean, that was just one of my favourite episodes ever to record. I think the authenticity and the depth of the conversation there made it one of the most unique that we've actually done. I want to say huge thank you to Owen for coming on the show. If you'd like to see more from Owen, you can find him on Twitter at Owen. Likewise, it'd be great to welcome you behind the scenes here on Instagram at H Stabbings 1996 with two Bs. I always love to see you there. But before we leave you today, I want to take a moment to mention HelloSign, a great example of a company that found success in building a product focused on user experience. HelloSign is an effortless e-signature solution used by millions to securely send and request legally valid digital signatures and agreements. They raised a total of $16 million in funding and recently got acquired by Dropbox for an impressive $230 million.
28:49 Harry Stebbings? Check out hellosign.com/20vc to join the thousands of companies and founders who value fast, secure and simple e-signatures. And if HelloSign helps you sign that term sheet, you need to get the term sheet in the first place. And I want to give a mention to Draper Esprit, a publicly listed VC fund that invests in high-growth European tech companies with global ambitions. Their portfolio includes companies like Revolut, UiPath, Kazoo, Graphcore and many other top European companies. Draper Esprit writes checks of USD $5 to $50 million, focusing on sectors like consumer, fintech, health tech, deep tech, enterprise and SaaS. And their investment team has an incredible depth of experience, both as operators and investors, that helps businesses scale globally. If that sounds like the sort of investor you
29:34 Harry Stebbings? want to work with, get in touch with them at draperesprit.com. That's D R A P E R E S P R I T dot com. And last but by no means least, if you don't have a SOC 2 report, you aren't going to be able to sell to major customers. SecureFrame helps startups get and maintain SOC 2 and ISO 27001 compliance in as little as two weeks. Join companies like Stream, Hasura, Benner Pass and unlock more sales with SecureFrame. 20 VC listeners get 10% off at secureframe.com/20vc. That's secureframe.com/20vc. As always, I so appreciate all your support and I can't wait to bring you an incredible episode next week with Roloff at Sequoia.
Previous 20VC: Cyan Banister on Her Relationship To Money, Risk, Her Investment Decision-Making Process, Why We Will See A Reckoning in the Early Stage Market, Her Biggest Takeaways from HQ Trivia & The Future of Silicon Valley Next 20VC: Sequoia's Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia's US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success Page updated October 25, 2026 · transcript and summary are machine-generated
