Rowan Simpson on the right way to be wrong

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Speaker E: Jobs Kia Ora Kouto Kato welcome to Business Is Boring. Rowan Simpson has helped shape some of New Zealand's most iconic startups, from Trade Me to Xero to Vend to Timely. He's usually stayed behind the scenes, but with his new book, how to Be Wrong, he's come to the front to share some important and hard learned lessons. In this episode we talk about the value of being wrong. The people you never get to hear about who build great companies and what startup culture still gets wrong about success, leadership and capital. He's done a bunch of interviews to spread the word and the stories of the book. So for this chat we thought we would dig into some of the things he hasn't been asked as he's got the word out. Thank you for being here.

Speaker A: Oh thanks for having me again Simon. It's so good to talk to you.

Speaker E: I think you might have been on this like very, very early in, I mean like nine years ago or something.

Speaker A: That long ago? Yeah, let's not talk about that. Just makes us sound old.

Speaker E: But one of your first, first podcasts I think. And so it's so great, so great to have you back to Chat about the book. And, like, first up, like, what an awesome amount of media, podcasts, coverage that you've had for what could be seen as pretty niche book, right?

Speaker A: Completely niche, yeah. And I think, you know, when I was first starting this project talking to publishers, that was one of the questions was, like, you know, how big is the audience that would be interested in this? And, yeah, it's been delightful. I think the response to that has been great, and it's been wonderful to be able to share some of the stories, the good stories, and some of the. Some of the more challenging stories, you know, to hopefully a much wider group of people who are interested in this sort of thing.

Speaker E: Yeah. And, like, you dedicate the book. We'll jump into, like, you know, some of the themes, um, and then come back to this idea of, you know, the importance of these stories getting out and who normally gets to hear the. Right. But you dedicate the book to the quiet ones, uh, the people who build these companies. How do you define that? And do people always get that definition right when they get to that idea of the quiet ones?

Speaker A: Oh, not always. Right. I think. I mean, I've basically spent 20 years hiding in plain sight. You know, like, I think you talk about stepping into the spotlight, but I've actually been writing about these companies that I've had the privilege of working on from the beginning, more or less. I started blogging in 2006, um, when that was cool. Um, and, you know, like, it's been always good to share those stories, and I think there's been a small group of people who have kind of followed those things that I've written closely.

Speaker E: Um, and, yeah, I was right there from when you were doing the running journey.

Speaker A: I mean, there's been a few ebbs and flows in that, too, over the years. The Olympics sort of pops up every four years. But, yeah, I think, you know, I sort of formed this idea around quiet ones because of. Because of the experience that I had. So, you know, like, we often hear from or hear about the charismatic leaders, you know, the people who are good at promoting their own stories and. And the people maybe who, you know, have that kind of strategic foresight. M. And I never really felt like that was me. Like, I'm not. I'm none of those things. And yet there was still a role for me in all of these companies that I've had, you know, had the opportunity to work on and be part of. And so, yeah, I always like to look for what I call the quiet ones. Whenever you see somebody who's loud and successful and flamboyant. Who are the people who are working with them? So, I mean, a couple of examples from the book. I reference Bernie Taupin, for example, as maybe the canonical quiet one. He's written the words for every single Elton John hit. And Elton John's this hugely charismatic person. And Bernie Toppin's almost the exact opposite of that. You could probably walk past him in the street and you wouldn't know. Um, but there are like, it feels like that's just such a repeated pattern. So another example from the book is Susan Wojcowski, who was the marketing manager at Google in the very early days. It was actually her garage that the company was started in. Um, she was the person within the team who led the YouTube acquisition, for example, hugely influential person in the Google story. And I'd be surprised if anybody listening to this was familiar with her name. Do you know what I mean? And yet, so, you know, there's always those people and I always found that a really encouraging thing because it means that there's roles for lots of different types of people in these companies. But yeah, quiet doesn't mean silent.

Speaker E: Yes. And like, you know, by saying the charismatic ones at the front, I mean, I think a lot of the quiet ones are often like, you know, could also be charismatic people within companies, but just not the ones that are necessarily outward associated with it. Uh, because it's too hard a story for the media. Right.

Speaker A: Like it doesn't fit nice nicely into a sound bite. No, that's for sure. Like when you tell a story, journalists will ask, how did you have this idea? And you need to kind of give them the 22nd or 32nd answer. And there's not enough room there for the nuance of all the different people and all the different contributors. So yeah, necessarily we end up attaching one name typically to each successful company. But when you dig just very slightly under the surface, you find there's always a team of people. And any successful company has 20 or 30 or more people who have been load bearing to that success 100%.

Speaker E: And like this podcast is part of that kind of mythologizing of the founder because it's the entrepreneur's journey which necessarily, uh, you know, um, flattens out all the detail and makes it about that founder story. But from working in these companies, you know, like, I think, you know, the 10 people who are the absolute kind of, you know, low beer is a great expression. Or you know, the people who are incredibly impactful, but they may be more well known in Their product meetup group.

Speaker A: Yeah. And I think this is back to the quiet ones. Like it served me very well to not be the one who was constantly on podcasts and in the media and what have you, because it let me just get on with the work and actually, you know, the, the doing the mahi is ultimately what creates these successful companies. Like getting famous is kind of a side effect that some people involved in those companies have to cope with.

Speaker C: Yeah.

Speaker E: And you know, as someone who has been following along your writings, um, for boy, what is quite a long time now.

Speaker A: Thank you, Simon. I'm very old. Yes. I think I hear what you say.

Speaker E: Well, definitely more than 15 years. Um, you know, like the themes are, ah, absolutely there and like you say, you know, hiding in plain sight. You know, you've been developing and honing and you know, very consistent, especially on things like that focus, you know, not being out there as, um, you know, doing the kind of publicity side of things has meant you've been able to really focus in on what the most valuable things that you can do are. Right.

Speaker A: Yeah. And I think people misunderstand focus as well. Uh, often people, when you talk about focus, think that that's about choosing the things that you're going to do. And actually it's the opposite. It's choosing the things that you're not going to do because that's what creates the time and space to do the things that you do prioritize well and do them exceptionally well. And then, you know, and then you get invited to talk on podcasts about

Speaker E: those M. One of the things that, you know, people have picked up a bit are the stories around, you know, what should be funded by the government and what should be done by, uh, the private sector. And I wondered like, how, you know, from m. The feedback and from the questions you've had, have people understood what you've meant from that or has it been something that is, um, still, uh, you still see all the same messages out there around, well, why don't we just put some more money into X?

Speaker A: Yeah, yeah. Capital is a strange one we've had in New Zealand especially, uh, for that whole time I've been writing, we've had the assumption that capital is one of the things that's holding us back. It's constraint. And yet at the same time, the four companies that I've written about in this book are great examples. The best companies have not struggled to raise the capital that they need. And so, yeah, I like to sort of dig a layer deeper on that and uh, One of the questions I ask people who complain about a shortage of capital, for example, is to ask them, what's the best company that you know of that has tried to, but failed to raise capital? And the answers are always underwhelming. They're actually not great companies that come back, if any. And. And in response to that question. And so that kind of points me to what the actual problem is. There's only a subset of companies that will ever be funded. Um, I guess the other thing around capital, which has sort of been misunderstood and I think a myth that maybe persists is that capital raising should be hard. We've maybe developed this mindset that we need to make it easier for people. But for a start, the venture capital market is global. There are venture capital funds all around the world and their job is literally to find the most successful, highest growth companies and to invest in them. M. So it's not hard to. If you're a great company, it's not hard to have good conversations with those folks. The hard part is being a great company that's worthy of being funded. And yeah, I think if maybe we focused on that a bit more and less used a perceived shortage of capital as the reason for what's holding us back, that might be a better mindset.

Speaker E: There's like a productivity chicken and egg thing here as well, isn't there? Right. Um, and it'd be really interesting to dig in a little bit about the way that you look at productivity in this.

Speaker A: Yeah, I think we let politicians get away with a lot on this, but every new generation of politicians will come in and say, well, obviously innovation and startups are, uh, the key to unlocking, uh, the productivity malaise that we've been in more or less my whole adult life. Yet we never really hold them to account on what they're actually doing about that insight. Um, the results have continued to be really underwhelming. One of the things I write about in the book is going and listening to Sir Paul Callahan in 2011. He gave his famous lecture, and in the startup ecosystem especially, we still repeat a lot of the mantras that he kind of rolled out in that lecture series. Be the place where talent wants to live, for example. We only need 100. Yeah, yeah, well, I was going to talk about that. So he famously said, we only need 100 companies as big as the top 10 that we had at that stage and we would close the gap with Australia, sort of run the numbers. And that was the maths more or less at the time. And yeah, I Mean, as part of writing this I sort of went back and worked out what we've actually done and we created net 7 out of 100. And so, you know, that's a very underwhelming result. You know, we kind of like to champion the startup ecosystem and talk about how great it is, but the actual numbers have been, you know, haven't been what we need them to be if they're actually going to have that impact in terms of really moving the dial on productivity and prosperity. And yeah, I heard a really interesting comparison in Australia recently. I was there and. And they have similar debates over there by the way.

Speaker E: Very much so.

Speaker A: And this presenter was comparing the number of people who are employed in the startup ecosystem in Australia with the number of people who are employed by Bunnings in Australia. It's kind of equivalent.

Speaker E: Yeah.

Speaker A: And so that sort of puts it in perspective really. It's like how many new highly paid jobs have we really created in this ecosystem? Because if we are not doing that then that, you know, the politicians aspirations around this are not going to be realized.

Speaker E: Well, it all comes down to, you know, if I can say the central theme of everything you say, which is help make a great company. You know, and like if you help make a company great and put your effort into making a company great.

Speaker A: Yeah.

Speaker E: Then it will be worthy of investment.

Speaker A: Yeah.

Speaker E: And it will create, be more productive and we'll do all of these things. But all of the stuff that isn't actually helping make a company great is not going to actually change anything.

Speaker B: Right?

Speaker E: Yeah.

Speaker A: And I mean I describe it as a paradox in the book. I think there were some of us who realized that the most impactful thing we could do is make the company that we were working on as good as we could make it. And a few of us who have had the privilege of doing that multiple times and that's actually what does make a difference. I think at the same time there's been a lot of people who have sort of seen the potential in terms of productivity m and hoped to create those outcomes from the top down and are still kind of hoping and waiting.

Speaker E: Yeah. And there are some settings, things. Right. Like if I think about um, Vend, you know, where I worked and got to know you, that had about 50 million of investment also go into it. Right.

Speaker A: I think it was about 70 million by the end.

Speaker E: Right, Right. Um, okay, so that's like 50 houses in Auckland. Right. And yet it created ah, hundreds of jobs. You know, um, extraordinary skills in the market, brought capital into the country and Then sold for half a billion or so from what is 50 houses, you know, street.

Speaker A: That's also only the first degree of impact. Right. Like the, you know, there are a number of people, yourself included, who had, you know, their first startup experience at Vend, who are now working on their second, in some cases third ventures. Right. So it's this, it's that sort of compounding effect too which often gets overlooked, I think.

Speaker E: Oh, like super impactful. Right. And then you think about that and you're like, well for 50 houses, that's an enormous amount of value compared to 50 houses in the world. And so there is a lot of investment that goes into things that are not productive. You know, it's not unusual for a property investor to have 50 houses. They are creating that kind of positive impact for the country. But they do need to of course be super high quality companies to invest in. Or else it's not just a simple case of just throw more money.

Speaker A: Yeah, Somebody, somebody has to start them. Like just creating the umbrella, creating the environment is not sufficient. Like somebody has to start them. M. Someone has to do the hard work to, to, to grow them and, and bring them up and, and yeah, I think, you know, that's, that's been my consistent advice through that whole 20 year period of writing is like, just do that. Like if and if you do that and you're successful, that will be the biggest contribution you personally can make to the, you know, to the outcomes that we all kind of aspire to.

Speaker E: And I think some people, um, know who work in the uh, startup theater space, um, you know, the people who are in accelerators and you know, these kind of things, um, the derivatives of the industry, I mean they could, you know, take it maybe a bit personally this idea that what they're doing isn't as um, beneficial as actually working in a company. Yeah, I take a slightly different view. I think some of these startup theater things are kind of just top of the funnel.

Speaker A: Yeah.

Speaker E: You know, but they're treated as if

Speaker A: they are the industry.

Speaker E: They are.

Speaker A: Yeah, that's right.

Speaker E: But they're just top of the funnel stuff. And like, so for example, um, Connor Archibald, you know, amazing. Um, founder, CEO at uh, co founder, CEO at Tracksuit. Um, he ran Lightning Lab and then went and worked in a startup, Mishguru, and then came back and um, started Tracksuit and has made an amazing company. But that first Lightning Lab thing, that was the top of the funnel for him to get out of law. And I think there's a real value to a lot of those things as the top of the funnel, but not as the solution to the whole thing.

Speaker A: I completely agree with that. And I mean you're right, over the years some people have taken that criticism personally and that's unfortunate. I was only ever playing the ball, not the person and those critiques. But yeah, I would also just question uh, the cost and the collateral damage of that too. So accelerators for example, uh, have proliferated and there are now some quite niche accelerators in lots of different places and lots of non tech actually sectors are copying that model because they perceive that to be the way to be innovative. And that's great for the Connors of this world who come through that successfully. Another example which is often rolled out when I am critical is sharesies which went through the Fintech accelerator for example, sort of overlooking the fact that a lot of those founders also came out of Xero and Kiwibank and other things prior to that accelerator. However, it's not so much the, it's not so much those that I kind of lean on as all of the others who have kind of been given a slightly fake version of how you are successful, which is you've got 12 weeks and then you're going to throw you up, push you on stage and you'll fly or die. And that's poor advice in my opinion. I think there's much smarter ways to approach the very early stages of, of company building. Um, without the theatrics that kind of get wrapped around that and without the publicity that gets wrapped around that. I personally think it's much better if you're going to be stumbling your way through the early stages, which of course you are because of all the uncertainty and you know, all the things that you haven't learned yet. Much better to do that slightly in the shadows and slightly obscure than sort of on the front pages.

Speaker F: Yeah.

Speaker E: And I think people do conflate it with. This is how you create value and I think this is how you give people a first taste in some basic principles. Very, very helpful.

Speaker A: Sure.

Speaker E: But uh, not.

Speaker A: This is, this is the thing.

Speaker E: If we just do more of this, it's because it's the actual building.

Speaker G: Yeah.

Speaker A: Ah. And let's, let's not allow that to take all the oxygen out of the room would be my other kind of criticism of that, which is really what we've done for most of those, most of those 20 years. It's kind of that, that, that derivative layer, the startup theater layer as I've described it, has become the thing and we've overlooked the fact that that's actually not where most of our really, uh, successful companies got started and have come from.

Speaker E: And you meet some people who've been through three of them or four of them and you're like, whoa. Yeah.

Speaker A: Which is, you know, that's partly why it's so delightful to be able to share some of these stories in the book, because I've just written the stories of what actually happened in those companies that we, that we celebrate where they got to. But it's kind of interesting to talk about how they got started and how they got there.

Speaker E: One other settings thing that doesn't come up as much as I think as it could because a lot of the startup ecosystem is hoping it can just ignore it, is capital gains. And I wanted to jump in and get your thoughts on that as you've been a proponent for capital gains and I couldn't be more of a proponent for capital gains. I think it's mad that we don't have it.

Speaker A: Right.

Speaker E: Tell us about how you think about that.

Speaker A: I think it's a huge blind spot for our whole country. Um, and like the, the, the, the analogy that I would draw is kind of to the imperial m, uh, imperial measurement system. You know, um, There are only three countries in the world that still use that. The U.S. liberia and Myanmar. And when you. And I think the Liberia, Myanmar, I have now a blend, I'm, uh, moving away from it. Uh, but when you go and talk to an American, they just cannot compute that the rest of the world doesn't use, you know, gallons and miles. And I think that the capital gains tax debate is New Zealand's version of this. Like we are a massive outlier in that we don't tax capital income at all. You know, zero percent more or less. There are a few around the edges,

Speaker E: unless you do something very, very dumb. Right.

Speaker A: And, and we just don't realize, I think, how much of an outlier we are there. So people are often surprised, as you just sort of expressed, that I'm not wildly opposed to capital gains tax because I think that's what they would perceive someone in my position, default sort of view to be. And I maybe just have a slightly wider perspective, which is I know plenty of venture capital investors and founders in Australia and in the US and in the UK and they don't think capital gains tax is unusual at all. It's just, you know, it's part of the water that they float and they expect to pay it when they have those outcomes. Um, and so, yeah, it's it's, I think it's a shame that it becomes this very political polarized debate because it also ties into how startups actually give, you know, create those outcomes that we were talking about before in terms of productivity.

Speaker E: Oh yeah.

Speaker A: And prosperity. Like we um, you know, the debate around startups, um, and the ecosystem and how that develops normally very quickly becomes a debate around what can the government do for startups. And we never really flip that round and describe how successful startups are going to contribute back to the government. And you know, this is sort of the answer to that. Like the best time to ask somebody to contribute by way of tax is when they've just received a massive cash outcome from selling their business. So.

Speaker E: And it distorts the uh, world of investment so badly that we don't have a broad based capital gains tax. Right. Yeah.

Speaker A: And this is, I mean this is part of our blind spot. Right. We think that houses and real estate are uh, how we get rich. You know, politicians, even at the highest level talk about getting ahead and this is how we think we get ahead

Speaker E: by selling, get an investment property.

Speaker A: We sell little bits of the country to each other at ever inflated prices. That's apparently getting ahead and send all

Speaker E: of the interest over to Australia and ruin our current account deficit.

Speaker A: There's that too. But I think, you know, like, get ahead of who is potentially a question that could be asked in response to that. I think, um, you know, creating, creating value for the country through product, productive investments, um, feels much smarter than hoping that prices of non productive assets continue to inflate.

Speaker E: Oh, and, and the idea as well that if we don't have some kind of capital gains tax and become, you know, I, I don't understand why we don't say, uh, make it a non political issue and just go, hey, we're just going to have parity with Australia. This is the same thing they have in Australia. We're not gonna bring in stamp duty, we're not gonna bring in these other things. But we need to have this because it's distorting the environment or something. I don't know.

Speaker A: Yeah, I mean let's just for a start acknowledge that we're Liberia and Myanmar. In that sense it wouldn't be unusual for us.

Speaker E: Ah. Uh, and it would be so healthy if we then brought it in because I think there's a real movement in the world around tax fairness and if we're not careful we're gonna end up with some kind of wealth tax which for people in startups and the High growth venture ecosystem is the absolute worst possible outcome. Because paying tax on unrealized gains and things that have weird valuations and they still blow up and you can never claw back any tax paid if it does blow up is going to be such a disincentive to um, the sector where if we just had like a very simple fair tax system that said, hey, you sold something for heaps, give us a small amount of,

Speaker A: would just be priced into those deals. Like, I mean the example that I have used when I've been questioned on this in the past is the Trade Me sale. So we sold trade me for $750 million. It was a cash sale, more or less. And if there was a capital gains tax, we would have all gotten large tax bills at that point and it would have been priced into the deal like it would have been factored into the price that we were willing to sell that company for. And the reason I know that is that that's exactly what happens in every other country in the world when these sorts of transactions happen. It's not unusual.

Speaker E: It's part of the conversation. After capital gains tax, you will end up with X as part of that conversation than any other country. And it's kind of bananas that rather than having a very simple tax system where there's a liquid, there's a cash events, there's liquid money to actually pass over and there's been uh, a actual price decided by the market. Yeah, yeah. So yeah.

Speaker A: Uh, but this is like, I think it's also you sort of close the loop there. Like often hear successful startup founders talk about startups and the ecosystem and building these kind of tech companies in New Zealand is the way that we fund schools and hospitals. Well, if we want that to be true, then there actually needs to be an exchange of cash at some point in the, in the process to f. To pay for those schools and hospitals, you know.

Speaker E: Yeah, past just the PAYE and GST and all the rest of that kind of carry on. And like, as a kind of final thought to wrap up this part of the, the section, you know, from the book, is there anything now that you know, that's been shared widely that you would choose not to have in there?

Speaker A: Uh, yes. I would delete every time I wrote the word similarly and I would delete every time I wrote the word prioritized. And I would delete the times I wrote the word decision because it turns out I can't say any of those words very well. So I've just finished recording the audiobook of this, um, of how to be wrong and it nearly killed me. So, uh, I would choose my vocabulary quite differently. Uh, less facetiously, there's one part of the book where I talk about how to pitch effectively and how you should think about approaching investors. And I share there, uh, a, uh, pattern that I guess I learned over multiple years of both pitching and being pitched, which is that there's kind of a pattern that most founders fall into where you start with the problem and then you describe your solution and then you move on to the addressable market size. And it's kind of a well worn path around that. But there are other kinds of pictures which actually start quite differently. They start with the expression I use in the book is they start with the words we realized. So they start with the experiments you've done or the insight that you uniquely have, or something that you've noticed that other people haven't noticed yet. And those are always much stronger pitches because they're actually building from your personal experience. And so I wrote about this and said the best pitches now always start with the words we realized. And so of course, every punishing founder who actually doesn't have insights and hasn't completed any experience now has started reworking their pictures before they send them to me to have the first two words be we realized, which is unfortunate. So maybe I should keep that one to myself.

Speaker E: Keep, uh, the pattern to match. Some of the most, um, surprising things in the book, I think for people were how you started by looking at when things were almost failures rather than successes. And so let's come back in and talk about one of the moments we worked on together at ven.

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Speaker E: So tell us how you did start the book there with the four near death stories, uh, of these four great companies.

Speaker A: Yeah, so, I mean, all four. So, you know, Trade Me zero vend and Timely, uh, are, uh, known companies because of the outcomes that we achieved, you know, the successes in terms of how, you know, how they grew and how they were sold ultimately. But when I came to write the book, I was really determined to start with the actual experience of working on and growing those companies, which is often much more rocky, much more, uh, like, you know, while each of those four companies had great outcomes, in the end, that's not my experience of working on them at the time. And so, yeah, it was, it was a conscious choice to start with. As you described it, the near death moments which all four of those companies had.

Speaker E: Trade Me, for example, it was a real bump to my kind of internal narrative of that company because I wasn't close to it at all, obviously. That you actually left it and went to the uk.

Speaker A: Yeah, not only me, but Sam and Jess, who were the founder and his sister was the second employee before me. We were all in London at one point working over there because it was

Speaker E: so uncertain it would be a big enough outcome to even employ you all.

Speaker A: Well, more than that, like we had more or less burned through the cash, the small amount of cash that Sam had raised and there wasn't really a functioning business model. So, you know, as I describe in the book, I left honestly unsure if Trade Me would be there when I came back. I sort of expected it probably wouldn't if I was honest. So I wondered whether that was maybe the end of my, the startup phase of my career. And yeah, as you say, that whole part of the Trade Me story has mostly been airbrushed out of the narrative over the years.

Speaker E: And then like the, the Venn story, which is one where that was where I kind of got to know you, uh, as you'd been, you know, the chair and around. But I was a junior, um, person in marketing and so didn't have an enormous amount to do. But I Did run, um, well, I ran communications, uh, for the business. And um, so when the restructure happened, I got to have a front seat to how the very small team of the exec and board ran the process and communicated it and made people redundant and then communicated to the market what had happened and worked with existing investors to cobble together ah, um, funding to allow it to keep going.

Speaker A: Yeah.

Speaker E: And then did a retrospective with everyone kind of very honestly talked about what went wrong and how things could be better.

Speaker A: Ah.

Speaker E: And part of the result of that is that as you say in the book, you were no longer the chair. And so that was like an, you know, extraordinary process for someone, you know, a couple of years into their startup career to see and view. And so I thought it'd be really interesting just to kind of like dig into that a little bit as someone who, um, had a view of that. Uh, and that's one of the kind of key stories of the book. So how was it that it came to be that the term sheets were there, the business, the deal was gonna happen to keep it being funded and then it evaporated?

Speaker A: Yeah, I probably need a few more years still of therapy before I can properly honestly answer that question. But I mean the nature of a fast growing business is that it's, it's somewhat chaotic, you know, like that. And this has been a repeated experience for me as you, you, you know, in the very early stages you're pushing hard to try and get the thing moving and then once it's moving and really growing fast, the challenge flips to running hard to try and keep up with it. And there were a lot of jobs to be done. And the honest answer to your question is, um, we've got ahead of ourselves. Like we, um, we'd successfully raised a number of rounds of capital, including the most recent round prior to that I think was at the time New Zealand's largest ever capital raise. I think that was the headline you came up with. And that success kind of creates a momentum that you have to keep running to keep up with. Um, and so, yeah, we thought we were progressing well with the next investor, um, and we started to spend that money before we had it. And that, with the benefit of hindsight, was a mistake.

Speaker E: In the world of startups, sorry, of SaaS startups, um, there are some very well known metrics that everyone follows that, um, give you a view of what the future value of the business will be. And my understanding, just as the crunch time came to get the investment in, they all just fell off the cliff.

Speaker A: Well, I mean that was one of the insights I guess from that retrospective you described, which would be great to dig into by the way. But the uh, yeah, I mean, and maybe a blind spot that I hadn't appreciated in the moment was, and I describe it in the book as we were right at the end of the era where Google AdWords was a viable marketing strategy. Um, you know, the cost of acquiring customers that way had deteriorated really rapidly and caught us off guard basically. And so yeah, as the new investor kind of got access to our, to our numbers and you know, and started to take a close look at that, that was enough to scare them away and at a much too late stage. Like they also behaved poorly in that process. But um, but it left us really

Speaker E: exposed and you know, timing and luck, which is such a part of every, you know, it can't be said enough how much of a part of it is a story three months earlier, maybe it wouldn't have been an issue. Right. And like that's the kind of time period we're talking about. So a little bit of a, kind of, you know, all the worst things. But as you say, like the model that we're in, uh, you know, an expression that you've been really good at helping popularize is default dead. You know, tell us about that. Like when you're default dead, what does that mean?

Speaker A: It's actually Paul Graham's line and I love it, I use it a lot.

Speaker F: Right.

Speaker A: I mean default dead just means that you're relying on being able to raise more capital in the future. Like you don't have a self supporting business model at this point. Um, even projecting forward. And yeah, it's a very confronting name I think to use but I think it does really focus your attention because as you described SAS companies, especially because of their economics, like you spend a lot of money acquiring each customer but in the first month they just pay you a small subscription. So it takes some time before you've recouped that investment. And so when you're growing fast, you actually need more and more cash to continue to grow faster and faster. Um, and yeah, that was definitely the mode that we had successfully navigated at Vend right up until the point where we unsuccessfully navigated it and that environment.

Speaker E: So you know, it was um, ah, you know, it had been New Zealand's fastest growing company. It had grown 1100% a year. It had um, you know, been, been a massive award winner. The trajectory had been up, it had been the first point of sale on iPad. And so it had had this extraordinary pull from the market, and then it was going through kind of growing pains of finding a business model as more people, uh, copied the simple things, more

Speaker A: specifically finding the next channels. So, you know, as I say, we'd sort of relied a lot on that relatively cheap inbound customer acquisition. And finding the new channels on top of that was still a work in progress. And there was a transition between those which. Which ultimately nearly caught us out and

Speaker E: that, that process of having a business where everything had been very up into the ride, uh, in every kind of sense culture, um, hiring amazing team, you know, all the rest of it. When you do have a situation like suddenly, oh, shit, the lead investors fall. Now there's no other lead investor there, we don't have money to sustain this model. We have to cut a third, essentially, of everything. Yeah. How do you go about. How do you go about. Yeah, you know, uh, coming to grips with that and then going into kind of do it mode.

Speaker A: Yeah. I mean, the kind of slightly facetious way I've described that is if you think growing a company is hard, wait until you have to shrink one, because that was much, much harder. And especially having to do that under time pressure and reluctantly, um, you know, that wasn't. That wasn't great fun. But I guess one of the things that sustained me, at least through that process, was I knew at the core it was a great company, there were great people and we had customers who loved us, all of those things. So it was worth fighting for. It was not a. It was not a, you know, this didn't work, thanks, thanks for coming kind of scenario. It was worth fighting for. Um, and yeah, I mean, when you say the lead investor fellow, like the new investor we were talking to backed away, but we had existing shareholders who ultimately supported the company through those were some quite confronting conversations. And I guess that was part of my role, as you say, as chair, was to kind of have those conversations. And they weren't super fun. I remember a lot of them in probably a lot more detail than you might expect. Um, and navigating that was complicated because there were lots of different opinions, even amongst our existing investors, is about what was the. What was the right approach to dealing with that situation. So, yeah, that was the work to do. And yeah, at the same time, as you say, like, we were. We had to cut a lot of people from the team, which is traumatic for them and for all, you know, yourself and others who, who were part of that process. Um, and then we had to make sure that the team that was sticking around, quickly refocused on the job to be done. And yeah, that's sort of what led to that, that retrospective that you described, which would. Would be good to talk about, if you're up for it.

Speaker E: Yeah, absolutely. And one thing just about the process, before getting there, one thing that really struck me was, you know, all the investors were being asked to reach back into their pockets and keep the company going, and myself included, by the way, yourself included. And then because of New Zealand, like employment law, no one had redundancy clauses in their contracts pretty much. But the company decided, even though didn't have enough money, to kind of keep going, and it was directly just coming out of everyone's pockets and they didn't have to do it at all to give everyone redundancy and to get Troy Hammond, who's Talent army, um, to set up to help to place people and put a whole lot of internal resources into trying to help place people into new roles and the like, at the cost of, you know, at that time, the opportunity cost of doing more stuff to, you know, write the company up and the like. And that really struck me as, um, you know, obviously a very decent thing to do, but it was never a question as well. It was just kind of like there really was a culture around looking after people and so that work was done. And I think that, yeah, that really impressed me, the way that, like, the communication was so honest and how the principles were so strong as well, which were like, you know, step one, look after everyone. Step two, right, the boat. Step three, work it out.

Speaker A: Yeah, yeah. And I mean, that's.

Speaker B: Right.

Speaker A: I think one of the questions I still like to ask founders at the beginning, as, you know, as part of that sort of investment discovery piece, is why do you want this to exist in the world? And part of the reason for asking that question is really bottoming out how those people might respond when things get hard. Because there's lots of people who want to be founders. There's lots of people who, uh, would love the idea of being the person who's named in the press release when you've just raised lots of millions of dollars from venture capital funds, whatever. All of those things are relatively, uh, easy. It's kind of when those hard decisions or hard moments come along, um, that you ultimately find out what people are really like. And so, yeah, that, that felt important at the time to, to do that. Um, we had a strong team culture. You were part of that. Um, and even for the people who were leaving, they were always still going to be then alumni, you know, and um. Yeah, treating them right. And that equation was sort of non

Speaker E: negotiable in that retrospective. That was where, I mean, I came out of, um, um, media and um, advertising. And in those industries it's quite normal for, you know, if you work for an advertising agency and you're part of a global network and your parent company gets a different client, sometimes you lose a client you've got. And 30 people are let go. And that's just like life.

Speaker A: It happens. Yeah.

Speaker E: M. And I've worked for media. I've worked for magazines that have been disestablished, shows that don't get renewed, a station.

Speaker A: They're a common element.

Speaker E: But like, it's normal, right? In those industries it could. It could as the only common factor. It could be me. But like, you know, it's normal that like things go. But in this world, um, a lot of young people earlier in their careers, everything had been kind of very rainbows and unicorns, you know, like, um. Quite a, you know, quite a challenging kind of emotional process for a lot of people. It was a very. It was a very emotional process, helping to, you know, give people a very, um. Uh, respectful termination process. You know, it was a really. It was. It was. It was. Was, you know, quite. Quite a big process. Lots to hear for everyone really. Um, and then to do a retrospective where everyone just went like a good software project and went well, at the end of that, what did we learn? What went wrong? What will we do different?

Speaker F: And.

Speaker E: And the other difference, you know, coming from the worlds of advertising and media, no one does that. If something goes wrong, you just never mention it again.

Speaker A: Yeah.

Speaker E: And so you never get better. So that was a remarkable thing to see. How was it for you?

Speaker A: Yeah, I mean, I have to give credit to Lillian Grace actually, for that. She was the one who led that process for us. Uh, someone who both Vaughan and I knew. And we sort of invited her in to help us run that because it was, I think, important that someone from outside of the team helped facilitate that. And she did an amazing job. Um, in the book I say it might even be nominative determinism because, um, you know, a very graceful job, if you like. Um, so there were two sides to that coin though, for me. And I was part of that retrospective, you know, as a participant, but, you know, overseeing it. Like there was a selfish element to it for a start, and that we really needed to refocus the team quickly on the job to be done and to kind of accelerate the grief process. If you like. Um, I remember coming out of the little office where Alex Fowler and myself had locked ourselves to sort of call up various investors and ask for more money. Um, you know, came out a couple of hard phone calls and needed some air, walked out, and there were a few people just sitting out in the lobby, as you say, crying, and sort of put a lot of those what I thought were difficult conversations in quick perspective. But we couldn't really sort of allow ourselves to wallow too long in that because we still had thousands of stores all around the world that were using our software and paying us every month to do that, and we needed to keep moving. So that was. That was kind of the selfish side of the coin, I guess. And then the other side, I think that was really more important and ultimately much more impactful was what I might describe as almost the truth and reconciliation. You know, like, there were elements of the way that we had worked and the way that the culture had developed which contributed to the failure. And we really needed to surface those, say them out loud, and then all resolve to change those things, really. And, yeah, if I talk to one of those specifically, like, and hopefully you'll concur with this. As I say it, there was a culture which had developed a little because of the success we'd had, I suspect, of Everything is Awesome. I think that was actually even one of the stated values at the time. Yeah. And. And, you know, that sort of relentless positivity was part of our success. Um, but also one of the things that ultimately led to that pain, because I think there were people within the team who had seen some of those things that we were talking about earlier, like, they'd seen the acquisition costs accelerate, or they had a sense that, you know, that the conversations with the potential investor weren't tracking quite as positively as. As they could have or should have been. Um, but didn't speak up in those moments, because everything is awesome. And who. You know, and in a culture of Everything is awesome, the last thing you want to be is the person who's calling the emperor naked, you know.

Speaker E: Yeah.

Speaker A: And so, yeah, we needed to cut through that and acknowledge that that was one of the things that we had gotten wrong and fix that in the future. And I think, you know, we can sit here now with the benefit of hindsight and know. And know where Vend ultimately got to. You know, um, that was 2015, so it was only six years after that that the company was sold, as you say, for half a billion dollars. And, you know, obviously there was. There were There were more dips and challenges to come, but Covid to come.

Speaker E: Like, there was no guarantee that that company would make it through Covid when all of its customers were closed.

Speaker A: But I think if we, if we hadn't. If we hadn't done that retrospective and we had allowed ourselves to just wallow in the grief of the difficult situation we'd ended up in and to not address the things that we had all done that had contributed to that, then we definitely wouldn't have got to where it got to.

Speaker E: Yeah. And like, yeah, something I took out of that is the importance of being an optimistic realist. And like, that's very different than being an optimist. And it's very different than being a realist. And it's very different than being a pessimist. Yeah, but like, no optimism. There's no way to build something that seems kind of impossible to do. Yeah, but no realism. You can get to places where, you know, you, you, you aren't, um, laser focus on the things that actually matter. And if there's one reflection I have from that, that journey where we, we hired like 200 people in a year and we opened like four. Four offices, and we actually went from being an amazing product company serving retailers to an amazing company because we had no other choice, because we had to put so much effort into scaling that quickly. And that, that's where I think, like, you know, we didn't have the ability to be laser focused on the customer and the product and the market because we were scaling so fast. And now I'm like, I just don't know if scaling that quickly is healthy or good for anyone in the world unless you are able to do it with, like, an extreme focus on the customer.

Speaker A: Yeah, yeah. And I mean, I think that was at multiple layers across the company. Right. Uh, like, I've been asked a number of times, like, you know, uh, people have occasionally said to me, aren't you the metrics guy? Like, shouldn't you have had your eye on that? And yes, maybe that's true. Maybe I should have. And maybe that's part of the reason why I ultimately didn't say stay in the role that I was in. But, you know, there were, There were so many challenges for all of us in scaling, you know, and as chair, like, uh, that growing cap table, the, you know, the growing complexity of the investors that we'd raised large amounts of monies from was. Was all encompassing too. So there were, There were, there were multiple versions of that in multiple parts of the company.

Speaker E: I think I think it's just so cool to like talk about it because it is through those and the culture that was left, you know, because everyone who was removed from the company was great people and we could, you know, hand on heart say they're only going because of changing, changing um, you know, the funding model. But the people that were left, you know, like dug so. Dug so deep and were so aligned on what we were trying to do. And you know, we're able to deliver a lot with a lot less people and a lot less resource like multiple times too.

Speaker A: Like you talk about the four death, near death moments. I think all four of those companies at the points where they faced that trauma learned really important lessons that, that, that became sort of fundamental to who, who they were as companies. And yeah, I think that that's, that's maybe part and parcel is like, you know, to, to really get those deep understandings sometimes you need to that fortune and fire, you know.

Speaker E: Yeah. And you know, um, it's wonderful to share those stories as you know everything's a success in hindsight. But you know, there was no guarantee that timely or the end would make it through.

Speaker A: Covid. No, as I say like my experience of working in all of those companies was um, was deep uncertainty that they would exist for much longer all the way through, you know. And so yeah, it is, it is kind of curious to me that, that those companies would now be put on a pedestal as, as great examples of up and to the right. You know, that that was, that wasn't the lived experience for sure.

Speaker E: I think like a couple of things to kind of close off and thanks for going deep on. It's super interesting um, to talk about the things that don't work and you know, coming back to that title of like how to be wrong talk us through like you know, you know, like you say you didn't know that it was going to work. How do you get into a state of like when you know you're in the right wrong, you know, you know, not in the wrong one. Cause that's something you really focus on.

Speaker A: Yeah, yeah. I mean the title of the book was a really conscious choice too. And it's not supposed to just be, you know, self deprecating. It's actually a mindset I think. And so the mindset is accepting that you're probably wrong about lots of things. Um, because you almost certainly are. And the key is not to uh, not be wrong. The key is to identify those things as quickly as you can. And yeah, not so you can celebrate Failing fast or whatever the other startup mantras might be, but so that you can correct those things like, you know, the way you, the way you are ultimately. Right. Is by finding those small ways that you're wrong while they're still small. Um, and so yeah, I mean, it's just, there's kind of no great revelation as I run through this list of things that are part of that mindset. But uh, they're all uncommon behaviors even though they sound so simple. So just things like measuring everything, um, looking out for bias for example. So make sure you don't, you know, have those blind spots, um, being honest about results. And then yeah, like even as a, as a hardcore metrics guy, like balancing those objective realities with some external perspectives, who can help you give that sort of broader context. And you know, as I say, if you can do those simple sounding things, you'll be a real outlier.

Speaker E: But yeah, like, you know, another thing that you've said over the years, which is, you know, things go wrong when you stop hearing from people.

Speaker A: Yeah, people.

Speaker E: When the numbers do get hard or the results aren't going, or the performance isn't going where they want instead of running straight into it. Yeah, people tend to shy away or, or deprioritize working on them. Right.

Speaker A: Yeah, it's a real counterintuitive behavior. But like, I mean, when you realize that you're wrong, first of all, take a breath like you're not unusual. Just like. Hopefully one of the lessons people take from this book is even the most well known founders that you know of and all the people who worked with them messed up in lots of funny ways all the way through. And then put your hand up like it's surprising how common it is for people when they realize they've made a mistake to go into their shell. When the people who can most help. Ah m. Um, the people who are most likely to be able to help them resolve that situation are often right there, uh, unaware of the situation because they haven't been told. So yeah, um, the biggest tell I have that a company that I've invested in is in trouble is you stop hearing from them. And there are now people who I work with closely who send the most inane of updates. They actually don't have much to update on, but they just have gotten into this habit of sharing regularly. And so yeah, that simple behavior is surprisingly, surprisingly likely to help you get out of those holes.

Speaker E: And how do you make being wrong safe? Like what do you say to a founder? Or how do you make a Founder or operator feel safe to be wrong.

Speaker A: Uh, I mean I think it's a, it's a very uncomfortable position and it's something that I think develops over time. I think someone that you've just started working relationship with probably is going to have that reluctance that we were just talking about and yeah, I mean to tie some of these things that we've been talking about today together. Uh, all the more reason why a 12 week accelerator program is unlikely to lead to those kind of deep connections. You know, all the more reason why, kind of perpetuating this myth that failure is somehow to be glorified. Um, you know, I think that just makes it more uncomfortable for people to have that mindset of lots of small failures every day. You know, um, and more importantly that correcting those small failures and only making those mistakes once is, you know, as we talked about retrospectives to, to try and surface those, um, that's all part of it.

Speaker E: I often think that like, you know, as I said before, I came from creative and advertising and I kind of, you know, facetiously said no one talked about it, but it's absolutely true. No one talked about anything like, you know, people made million dollar mistakes and just never mentioned it again and we didn't have.

Speaker A: Which probably means those mistakes were repeated over and over, right?

Speaker E: No, no culture, uh, no institutional knowledge and then coming into the software world where people were like, okay, tell us what your assumption is and then we'll run a test and if it's right, we'll keep doing more of it. And if not, we've learned something and there's no blame if you get something wrong as long as you're getting it wrong in the um, pursuit of a goal as long as you don't keep doing it.

Speaker A: But let's not absolve ourselves. Like let me give you an example of the sort of behavior you're describing from creative sector in our own like NZ VIF was started in 2000 single digit, um, and has been kind of persisting with different models for all of those years since. Keeps getting more and more funding from government, has just again gotten another top up but without ever really being honest about the results that they've achieved. Um, and that's exactly the behavior that you're describing.

Speaker E: Right.

Speaker A: If you don't, if you don't surface those things, then there are no lessons.

Speaker E: M. Yeah, that's a big old naughty one. Their performance in the last five years is a completely different beast than the first ten years though.

Speaker A: Yeah, but why, like, you know, if you haven't, if you haven't, if you haven't understood why things didn't work, then when things suddenly do work, you still don't know why.

Speaker E: Yeah, yeah. And that like, yeah, as a kind of final couple of thoughts, like, how will you know if how to be wrong has been a, uh, success? Because I think there's a really interesting thing that a lot of these themes, you know, you've been working on these themes for a long time and in the companies, you know, to your point, the most important thing you can do is help a company, you've been helping the companies you work with think about these things, which is, uh, you know, very clearly a reason that you've got an unusually successful track record. How will you know if it's, you know, and what I was about to say before, like, you know, the software thinking, if more of this was in more of the economy and in more of the other kinds of businesses than technology or software influence business, I think we'd have less office politics, happier people, you know, like better work, um, engagement, you know, all these things. Because so many other industries don't have models where you can abstract the work from the person and it's okay to kind of like run an experiment and be wrong. And if the whole world could be like that, it'd be a better world. Right. And is that part of what you're working towards?

Speaker A: Maybe, yeah. I mean, unfortunately, one of the things that we export from the tech sector is all our mythologies. We sort of give them all the negative patterns rather than the positive ones mostly. But yeah, I mean, for me, I've got an unusual answer to that question, maybe as a author, which is for me real influence is when you hear other people quote you without crediting you. M. And that's, I guess my ultimate ambition with this too is like, I've shared in this book lots of stories. Like, you know, unusually for me, I've actually included myself in all of these stories rather than just sharing the business patterns and the dry lessons. But it's ultimately those lessons that will be the long term legacy of this writing. And the really delightful moments for me, and it's already happened and happening, is when I hear other people using those patterns or using that language, using those things that I've kind of in many cases learned the hard way. Um, if they can avoid those mistakes and still take the lesson and say them out loud and apply them and even teach others about them, then that's real influence and that would be success for me.

Speaker E: Uh, and then As a final thought, personally, what is success for you these days? It's like this is a big old project. You know, like, you've spent years honing this with the, um, you know, the writing online and then having comments and having people adding to it. Like, it's been a long process and then a big run to share the stories out in the world. Where does that fit into what you're spending your time on and what success is for you at this stage of career in life?

Speaker A: Yeah, it is. It feels really delightful to have the canonical version of all this writing now. I said to someone the other day, they were asking about Callahan Innovation and the fact that I published this book before Callahan Innovation was shut down, and I feel fine with that now. Like, in the past, when the writing was on substack and various blog posts and an old Twitter account, I would have felt inclined to update it. But now the great thing about a book is that it has a date on the first page. And so this is the canonical version. Hopefully it has a long tail. Hopefully even in years to come, people can still buy the book or listen to the audio recordings and take value from it. Um, for me, it's a difficult question. Actually, I don't have a great answer. One of the chapters in the book is called Nothing, which is about my first attempt to retire, and I completely failed at that. I ended up investing in Vend about six months after that. Um, so it's a complicated question, but, yeah, there's a model I read many years ago. I think it was Reid Hoffman's chief of staff. So Reid Hoffman was one of the early Facebook, early PayPal employees, early investor in Facebook, and founder of LinkedIn, amongst other things. Um, and his chief of staff talked about the dilemma every day of waking up and trying to decide whether you want to save the world or savor the world. And I guess that's, you know, the privileged position I'm in now as I get to sort of have those thoughts. And, yeah, hopefully for me, it's a mixture of both, I think, um, you know, it would. I still take a lot of energy from working with the founders that I'm working with, and many of those, for me now, because I get to choose those quite specifically, uh, are people who have been part of these companies that we're talking about who are now working on their next ventures. And it's a delight to be able to invest in them and advise them, um, and hopefully other interesting work around that. I still feel too young to retire. Um, you know, I felt that for 20 years. So maybe that will change eventually. But um, yeah, I don't, I don't know. Watch the space. Simon awesome.

Speaker E: Thank you so much for coming and uh, sharing some of the stories and the behind the scenes in that book there. And uh, yeah, can't wait to see what you make happen next. Thanks so much. Rohan Tsum Tsum. Thank you so much everyone for having us along in your ears and listening. And thank you to everyone who helps make this happen like our producer Teaihe Ah Butler. If you do like what we do, please do rate and leave a review. It really does help Enojora.

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Speaker E: I'm not giving up.

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