WeTransfer Boss Reveals All Since Selling for $500M+ - Damian Bradfield Exclusive

0:00Damien from WeTransfer, very excited to have you on the show. Thanks for joining us. Thanks for having me. I guess where I want to start is you've recently sold the company, right? WeTransfer just went through arguably the fastest exit process in history, six weeks from start to finish. Let's get on to that. Obviously, steps towards that. You had a failed IPO. You had a very impressively high valuation at some point. I've read reports of up to$2 billion. That's obviously been a real journey for you. I want to take it back to the start. Okay. Tell us how WeTransfer started. Why did you start it?

0:35What was the original inspiration? So you've got to go right back to 2009. Very, very different place, environment, internet than it is today. So Barack Obama had just come into power. Lady Gaga is top of the charts. The internet is still relatively rough, ugly, probably is the right term. And if you were in an agency or you were in any way involved in creativity, then probably half your agency was still sending stuff around on DVDs and with bike couriers. And the only way really to sort of share stuff, if you weren't sending stuff on a bike courier from one side of London or Paris to the other, was through some sort of awkward FTP site or maybe rapid share or mega upload or something like that.

1:24But the majority of those businesses were basically in the business of porn, piracy. mega uploads business model run by the infamous kim.com was all about promoting the most pirated content um and he proudly did this you know for for years and then ran away and hid in hong kong and now is in new new zealand facing extradition still you've always struck me as a classier version of kim.com actually now you mention it you do have to check out kim.com's website because he throws his occasional parties where he rents in people like the FBI to come and track him down and then he manages to escape from them and then appears and DJs from the roof of his like New Zealand villa it's tragic it's probably the right word so that was the basic the marketplace and um we transfer was really just you know the antithesis of you send it mega upload rapid check you send it we transfer and the idea was really to create something that was simple and well designed And I can't overemphasize enough how ugly the internet was in 2009.

2:29No one was doing design. Design was a thing that took place in books, still outdoors, on TV. But the internet was really all about banner advertising, awful, ugly, annoying, irritating. And engineering was a thing that everyone focused on online. So sites were driven by engineers, programmed by programmers. and WeTransfer was built in Flash, like the worst piece of software you could ever use to create something terrible for SEO, impossible to do anything with it. It was sort of static and unmovable, but that's what we knew how to create in. And you could actually produce something quite beautiful in Flash, very simply.

3:10And we had a couple of servers, a site that was basically really easy that anybody could use it, no sign up and one simple ad format in the background again trying to be the antithesis of what was being offered on the internet at the time and you know it hasn't really changed that much i mean to be to be frank it was good um it made sense it was easy to use it still is and it was a time when you didn't have to spend a single penny on facebook or instagram or anything else for growth for growth nothing so all we needed to do is basically to make sure that somebody used the service uploaded something and shared it with somebody else and that virality meant that we went from like zero to 200 000 users in no time um nalden who is like you know main founder design sort of i guess visionary for the for the platform had already a blog and he was like the equivalent of mashable at the time and he was basically promoting it on his platform and with the combination of that and stumble upon which again in 2009 was a big deal it's definitely not a big deal anymore i do think it still exists but obviously doesn't mean anything but it was tell us what stumble upon was for those who might not be pushing into their 50s guesswork here mate so i'm not nearly 50 but sorry presumptuous pushing into their 40s stumble upon was a sort of like Russian roulette of websites and it would just throw up suggestions that you might find interesting.

4:46And it could be anything from, you know, I don't know, a car search site to a music site to WeTransfer. And if StumbleUpon featured you at that time and basically threw out a suggestion to all the people that had signed up to their service, you were guaranteed a certain amount of traffic. They featured us. It blew up. and that's what happened time and time again basically you know people would discover us they talk about it organic growth would continue one person uploaded something three people would download it and before you know you get to like 10 million users i suppose the fascinating thing is that people were sharing it because of the utility of the time you know people were like this is amazing as functionality right just for the context it was it was unusual because it was so simple it was unusual because it wasn't trying to trap you you send it was upload something oh it's really big let me throttle it and annoy you until you decide to upgrade to the premium service and then we spam you and irritate you and everything else and every other service was basically if you want this we're going to hit you with a thousand skyscraper banner ads until you basically have earned enough money to allow you to do this for free and our service just came across as if it was like over generously beautiful and free and so many people i mean still so many people would say i don't get it what's the catch how do you make money doesn't make any sense do you have ads and be like what are you looking at i'm like oh yeah is that an ad and it was like the greatest compliment so in the early days how did you make money ads right that was it but i suppose your unique proposition was obviously you know back to your point so there's that famous john hegarty quote when everyone zigs you zag and you were talking about banner ads and all of the things all over the site and you guys just had a full page ad and that's all you could do and it was stunning and you know what i just sent to you on whatsapp like two days ago someone doing probably the 50 billionth breakdown of a we transfer ad campaign but it was uh roger federer and nadal right doing some exploring on a mountain in louis vuitton luggage and stuff as just two legends going on a journey and we transfer is like you know their main thing that they're doing with it it's a perfect example of what a compliment to you you get louis vuitton and two of the greatest legends of sports ever and that's where they're choosing to place that ad our biggest advertisers are luxury the the luxury world is like 11 out of the 12 biggest luxury brands advertised with WeTransfer.

7:15It's also the most brand safe advertising on the entire internet. And I'm not overselling this or exaggerating it. If you buy an ad on WeTransfer, it doesn't sit alongside an article about Israel or Palestine or Donald Trump or whoever else. It's just an ad. There's no content around it. You don't sit alongside another ad. So you're not competing like you might do on the New York Times for ensuring that this is safe and the brand's not going to get offended. And luxury, that's very, very important for them. They don't want to sit next to another ad for another luxury goods firm. And they definitely don't want to sit next to a political ad that may alienate their customer base.

7:56So it's like - They just want traffic and simplicity. And beauty. And that's what it offers. And in the beginning, it was really, really tough. I mean, we were basically pitching all the time. We'd go and speak to media companies, advertising agencies and we'd say listen for 16 banner ads you can have one ad on we transfer it's the same price as a banner ad but it would give you five times the click and people go yeah yeah yeah great can we put it into the programmatic formula no okay thanks good night time and time again and then it you know after like two years of beating down doors we actually did this ad where chrome this is how freaking old i am chrome had just launched pushing 40s calm down i know but chrome had just launched people would be like chrome did launch i thought it'd been around forever no it didn't exist until like 2012 i think yeah and and we transferred we just ran better on chrome it's faster so if you if you were using safari or whatever else you might have been using back then.

8:59Firefox and... Firefox. Chrome was just like up to 19 times faster. So we just ran ads saying, use Chrome. WeTransfer runs better on Chrome. Installs of Chrome were crazy. Suddenly we were driving it to Google. Essence Media could see what we were driving in terms of conversions. And they called us up and started spending 200k a month. Wow. And it was a truth. It wasn't that we were trying to sell ads. But this truth was that actually our servers are better and a lot of people still to this day will get annoyed with us because they'll say we try to be so slow and be like is it can can we just do a speed test oh you've got like a nine megabit connection and you're trying to upload 17 gigs it's not us it's you but people don't want to hear that so they would always blame us we were like if you use chrome it's just going to make our lives so much simpler and it turned out to be one of the biggest advertisers we ever had and i read that you effectively bootstrapped the company to begin with for much longer than is normal six years six years of bootstrapping and then you took investment yep so what was the thinking behind that of bootstrapping of bootstrapping for so long and obviously being successful and then moving into taking investment okay so the honest answer is that um we were a dutch startup and we were a design driven startup and people don't want to hear that people wanted to hear that you're a startup not even coming from london right ideally you're coming from silicon valley and you're for and stanford harvard um engineers building something that's going to change the world and we were like designers or you know people from the media world in amsterdam producing something beautiful that didn't conform to anything that was really difficult to sell no one was interested in investing in us so i could take the moral high ground and say we always wanted to bootstrap the business we had no we had real beef with vcs and we were trying to do something different no we desperately wanted to take money because that was the game success was that you did angel seed series a b c you did all this tech crunch was writing about you because you were climbing this pyramid of success um the honest answer is that no one was interested in us because we didn't conform so we bootstrapped because we had to bootstrap um we were all doing part-time jobs and running consultancies and stuff on the side while we transfer is running i mean we had a gallery we had another app called cover we had an artist and algorithm platform which is like um nfts back in 2012 we had loads of shit going on and around the side to pay the bills to to keep all the other sort of stuff going.

11:47In 2015, basically, one of our partners had left the company, had quite a big stake, and a couple of others really wanted to get some money out. So that's why we took VC. So you took VC to also do secondary so that you guys actually could live more comfortably as well? Yeah, I mean, we were paying ourselves like 2.5k for years. and there came a point where it's like okay it would be nice to actually be able to you know eat yeah i know i went poor but you know to be able to go on a nice holiday or do something and um what was also the case is that in that time and thank god it happened i mean it was a beautiful thing actually that we bootstrapped it in that time period because we demonstrated that we had a business model that worked we demonstrate that doing something different was really appealing.

12:41And by the time actually Highland, who was the investors that came in 2015, turned up, we'd been profitable for two years. And we could demonstrate it. They didn't need to change anything. This was just working. If they put money in, they would get money out. And I can complain about where we transfer this today or what's going to happen going forwards. But because of that period of actually not conforming and being rejected time and time and time again, we actually proved that a business model that somebody bought into and went okay this works don't all right don't change it what you're doing with we present or whatever else you're doing seems to make sense don't get it but let's not change it you know if it ain't broke don't fix it you raised about 25 million in series a is that right yeah what valuation was that ever disclosed 50 i think oh 50 yes hard harsh feels harsh that no quite low valuation i think it was 15 million i think it was 15 million and at 50.

13:40okay fine got it um reflecting back on that now did you take any more rounds after that yeah okay so reflecting back on that moment which obviously changed the trajectory for you right change the course of how you run the business would you do it again no why not it was profitable i mean there are so many things i would do differently i'm not saying I have regrets, right? Because all these things lead to another conclusion that take you to another door that, you know, leads you down another avenue that turns out, you know, to be beautiful. And there are many beautiful things that have come from it.

14:15But it's so easy to look back and go, you know, oh, I would do it so differently now. 2024 is a very different space online in investment in business in society than it was in 2015 um the the context has completely changed so knowing what i know now no i wouldn't do it um the you know the beauty about we transfer was actually it's a very very simple product it's just like could be run by a few engineers a few designers a few customer support people maybe a team at 50 you know could run we try to be the world's greatest lifestyle business frankly yeah yeah yeah it would have been an amazingly beautiful dividend business that just ticks along and people never even talk about that but i mean as a model that sounds like like a dream the dream i think you don't really set out with the intention of that being the dream and then if you do the entrepreneurial roller coaster for for enough time you probably realize that really is the dream yeah i mean i would say all of my friends now who've been through the like the sort of tumble drive with vc and p buyouts and stuff when you talk to them about what they're creating now i'd say that 75 percent of them are creating businesses that they know will pay consistent dividends they don't care as much about the valuation and the the tech crunch crap yeah totally our tech crunch is irrelevant it is now but i mean the point is still the same the new tech crunch whatever the thing is right i guess the point is people are less interested in their ego side and what everyone else thinks about them and more like well actually i'm mature enough now to know what a great business looks like and it looks like what you're describing in 2015 you know if you were if you were like founder of a successful company you were nearly like can you west this was serious a rock star yeah you were serious business and people wanted to put you on the front of magazines and all sorts of stuff there's no white tech bro that's on the front of time magazine anymore it's just unless they're in jail yeah unless they're in jail there's hope for you yeah don't worry about it yeah exactly um okay so you regret it you regret that moment in time so we don't have regrets but as in you would know differently yeah yeah it would be that okay yeah and so you raised a few other rounds in between um and then you had this like whole process with an ipo can i can i ask can i ask yeah please the you raise a series a money and then presumably that set you on a treadmill of we will spend more to hit certain targets and did that lead to multiple different funding rounds because presumably you could have kept going at the rate that you were and been happy so we didn't again we didn't follow a particularly conformist path thereafter and the other rounds that followed were also mainly secondary so removing other founders from the business um there was never massive pressure from our investors to overspend um to you know go out for all growth go for growth at all cost that just Actually, I would never say that they were particularly brutal or harsh or pushy or anything else.

17:43In actual fact, we were left alone to do what was working for the majority of the time. The moment things got trickier was when it was heading towards an IPO. That changed everything. Suddenly, we were employing very different types of people. we were ramping up in terms of the number of employees that we had the level of like middle management that needed to be in place um i mean for an ipo you need to have an awful lot of different roles that never ever existed in in our time um and in the full life that an awful lot of that is policy and process and procedure that um it's difficult to understand i think um but But we went from probably, I mean, there's numbers, I'm terrible with numbers.

18:35So it's probably went from, we went from like 150 employees to 250 in the space of six months or something. Wow. Gearing up for the IPO. I read somewhere. So, you know, obviously the internet is the internet. But I understand you were going for an IPO at 700, 800 million dollars, like that kind of range. There was also an equity financing round where you sold like a tiny bit of the company and that would have put you at around a$2 billion range. and obviously in the meantime you've also brought on like a mutual friend Martha Lane Fox as chair right and you've also got this sort of amazing claim at the right time in the market about being the world's biggest most successful B Corp which is in tech in tech that's also super interesting narratively at the time of doing all of this stuff and then of course everything around success in business annoyingly is about timing so it felt like everything was just on the cusp of perfection, the valuation, the tailwinds, the business you built, the people you are hiring.

19:33You know, we hung out in LA, you'd opened up the LA office, you know, you'd hired Martha Lane Fox, you know, one of the OGs of tech in Europe, just all of the things. So what happened? Timing. So I don't know if everything was going right, or, you know, if it was, it was amazing as we now make it sound. But when you start the IPO process, um i enjoy learning so it's an incredible learning curve right suddenly you're opening up yourself to the world naked and you literally do just expose yourself um and you know banks start knocking on your door and yeah we had ranges going up to three and a half million from a billion from certain banks um but you know deep down sorry it ranges from three and a half million to a billion no no sorry to three and a half billion to like 750 million that was sort of the range and in that courting process, it's fascinating to see how different people respond and to be like, okay, I know what this business is worth.

20:33What did you think the business was worth? Did you have a particular more practical view of it, being English as well? Yeah, I mean, so that probably is part of it too, but 750 million at that time was a fair valuation for the business. Everybody wanted the billion because that puts you at unicorn status. and then suddenly you know it's like you know platinum tier of british airways something it's like i need to be in need to be in those seats so that's what everyone was like pushing for and as if like 750 million is not good enough it's not to be a unicorn you don't get unicorn status and you won't get that upgrade would that get you there in dollars or are we talking in dollars no this is euros okay yeah it would have been close yeah um anyway that's like the you know the sort of benchmarks everyone was pushing pushing up north um but i think a fair a fair number was 750 that was sort of at the time but also you know having done this business for a long time and we had rejection after rejection between 2009 and 15 i knew how people received the company particularly analysts particularly you know the the analysts that work for banks and for the bigger institutions they look at us and go file sharing business file sharing is dead everyone knows that um no one's going to be sending files in the future okay i've been hearing this since 2009 it's still okay right email hasn't gone anywhere either sort of pretty futile technology really but still very popular um the next thing would always be you know okay your advertising's weird it's not programmatic it's difficult um advertising is dead okay it's growing like you know 40 year on year but yeah sure i guess facebook are doing all right i guess if we're just doom mongering scenario here then uh yeah that's also dead and they'd look at subscriptions and go okay yeah subscription's quite interesting but your churn's quite high and um it's really hard to compute how to value a business that's got two business two revenue models yeah and what everybody wants is a comparable and they would look at us and go okay so who are you you're dropbox no you're not quite dropbox are you because you've got this advertising thing that's annoying advertising okay so you like um conde nast we're not quite conde nast because you've got the subscription thing cannot compute so the the base of the computer would come back and say no time and time again it doesn't doesn't fit into a model and particularly in europe so trying to ipo in europe you come up against a lot of no says naysayers that i think are just not trained to go okay this is interesting let's find a different comparable.

23:08Well, let's take a percentage of one and a percentage of another and treat it differently. In this market, I'm talking about Britain, but I'm assuming we're also sort of European. In this part of the world, that is a really difficult thing for people to get their head around and they just don't like it. So I knew that the process going to the IPO was going to be difficult as I'd experienced it so many times. And time and time again in the process, analysts would come back going, I'm not sure about this. And there's a massive difference, right? So if you've got if you're compared to dropbox the multiple is like four if you compare it as a software business to adobe it's like 20 so of course you want to be pushing towards adobe and um so given that we were also trying to really leverage you know the fact that we were in this creator economy and we were building tooling for creators and stuff like that and recruiting in that space and and i just think there was a lot of there was a lot of pressure on the company to to perform and it was looking really good and then you know february last year the market just stopped and just suddenly you know oh it was overheated everyone was trying to get out they all got out people panicked no one was doing rpos anymore and then literally on the day for the day we were going out ended up pulling the plug 18 months work down the drain millions of euros spent on you know on the process on bankers on due diligence on accountants i mean certain businesses you should still be in they're always going to be good accountancy is definitely one of them um and we'd obviously had a lot of people employed that were specifically for that role and we no longer needed them so then you've got to go through the process of undoing it all okay you can't go back out and ipo again in three months or six months it's um it's sort of a one trick pony you've got to wait and the wait time they say is on average something between three and five years um if you look at the market today there's still very few ipos happening i mean reddit is like one of the few that people have talked about and that happened months ago yeah um so you know in the last 18 months whatever has literally been very very few um so you have no choice if i've got investors that have got a fund that need to return money to their lps and they've got to get out.

25:31An IPO isn't a path and then you have to find a new path. And that new path is either going to be a strategic buy, selling to someone like Adobe or Squarespace. For us, that would have been sort of logical. Or selling to private equity or perhaps some other crazy construction like putting it up to Kickstarter and seeing if the community would buy into it, which would have been quite cool. But that didn't happen. when it comes so when it comes to the ipo you said on the day that we were going to go out with our ipo we canned it how does a conversation like that happen at leadership level and with the team can you reflect on that day like what was going through yeah was it one of the worst days of your life so for me actually um my father-in-law died at the same time and i always say to my wife that it's a blessing and a curse because it was I've never been in the business to make money it was never about making money the IPO for me was a was a way of trying to secure the future of WeTransfer and we'd set some things in place that I really was secure in the mind that you know if I died if this company went something it would still be there in a few years or 20 years 50 years and one of them was we create the foundation and we set up that one percent of our revenue went to this foundation and this was all in place and i felt like okay if the market buys this company and they buy that we're a b corp and they buy the foundation everything else and it's like it's sort of locked and still you've got to deal with joe public but it's going to be relatively safe uh and when that didn't happen i was like okay i know what's coming next this is a bummer my father-in-law died and it just put it into perspective it was like okay my wife was crumbling she had an amazing relationship with her dad um you know i could see i mean she he was in hospital for a couple of months so it was quite a bad period but just perspective it's like okay so this didn't happen so what it's there are bigger fish to fry um and i feel fortunate actually to have experienced that so that i didn't drown in the misery of a failed ipo for three months because it's not that important really but presumably that morning and that day you probably woke up thinking this business is ipoing it billions and then by the end of that day and that realization you probably because you're so experienced probably knew that you had six to twelve months of hell coming that's what i'm trying to understand as well right 7am the company's potentially worth billions this day and at the end of the day it's like actually i've got a couple of years of hardcore pain like how did because if you've got 12 hours the company's gone up by you know 100 odd staff you know you're not going to make it the ipo then you know what you know then the next six months will be horrible i mean i'm i'm i mean i don't know what i am actually sometimes an optimist sometimes a pessimist and in this is in this instance maybe maybe in this instance i'm always pessimistic um and always trying to at least keep 70 of the sort of energy and excitement of something happening back because i've learned over the years till the money's on the bank you just don't know and with the ipo yeah of course you're looking at it going okay all right i might be able to you know buy a holiday house something that'd be nice um but it is the most it's the scariest i think in terms of like all deals that you can do because you are as i said you're so exposed that um you have so little control over so much of it that it's um it's quite daunting i think going going through that process the thing that i guess was in the back of my mind too is that we'd we'd seen the market you know move a lot and it was it was obvious that it was hot and it was obvious that you know there was a chance that if we had gone out it would have ended really badly and had we gone out it wouldn't have been pretty i mean it's the timing was appalling or great depending on how optimism and pessimism flows through your body um but had we gone out it would have it would have meant that quite a lot of people lost money as opposed to making anything do you think you made the right decision yeah yeah 100 okay yeah i mean again long term was it the right decision maybe not for that moment absolutely and you don't know what the consequences would have been had we gone out had the company been underwater i mean in that time period remember made got made.com yeah they went out um we weren't in that position right we're profitable yeah i mean they're fundamentally quite bad business weren't they they had made yeah sounds like you were the kind of the dream business well again um beauty of hindsight we're a dream business today so in 2015-16 um a company that was making profit and not going out totally going to the wall at all costs and putting everything into the growth engine they looked at us like we were just some lazy european hobbyists you know what are you doing making money are you mental why aren't you you know tripling every year these guys don't know how to run a business they make profit oh and everybody that was coming into the company you know wait i don't know how many titles i've had over the years but quite a few and everybody that was coming into the company we go oh my god you really do anything in performance you're leaving so much cash on the table it's ridiculous and fast forward to today it's like oh yeah okay so the majority of the performance stuff that we've tried has failed because we're not we're not a consumer business and selling sneakers yeah you know we're something that's like at some point in the near future guys you will have a file to send not today but in the near future so all i need to do is keep you somewhere up here i'm building a brand so that you're at some point and going to remember me.

31:45That's like the least threatening tech version of a Liam Neeson threat I've ever heard. At some point, you will need a file to send. It's funny because culturally, I think that's a huge change in business, right? Your philosophy there is like, or I suppose retrospectively, your philosophy is you can build amazing, mid-sized businesses that are just beautiful businesses. Whereas the VC philosophy for the last 10 years has been pump at all costs and see if we can get one that goes to the top and then if if we don't you know who cares and it's kind of the same thing as we were talking before about like private equity you you create something beautiful and small and everyone loves it and then you think how do we make this beautiful small thing absolutely mass market and then you destroy the thing that once gave it its beauty and i think that's just the world over right now yeah and i I mean, it has been probably for the last 30 years, something like that.

32:45I feel like Richard Gere in Pretty Woman was the beginning of this sort of momentum. But it's changing for sure. I really think that the conversation around dividends has not been had in decades. And yet today I hear it, maybe it's because I'm looking for it, But I hear it more and more from people saying, you know, what's wrong with the dividend business? What's wrong actually with something that, you know, turns out profit and actually shares it and distributes it and looks after its employees? And in, you know, in the history of commerce, even in America, you go back 70 years and, you know, the annual report from a company like Chrysler, if you look into them, it proudly stated how they'd managed to increase salaries for employees.

33:33how much money they were making and being able to provide education and healthcare for their employees because their role wasn't just about you know maximum shareholder value return at all costs it was really about okay we're creating jobs here and we're creating something like costco right same kind of model waitrose john lewis the brands that people talk about you know with respect yeah and and that have been around for a long time and will be around for a long time one of the things that we transfer has obviously given you is a really interesting high quality creative platform and one of the questions probably the most frequent question i've ever had building heights is how the hell do you get stephen fray and the answer to that question is you uh you were one of my first investors uh you were probably in the first 10 maybe 20 customers full stop wow um still use it i know yeah i'm not no no far too much on dutch import taxes because he like whatsapps and tells me how i should do it better um well you've sorted it now it's sorted now thank you for your feedback um but you know it's really interesting because steven fray was one of the people that you casually know as you do and were generous enough to make the intro and happened just with amazing timing it was what he needed at that time and he became our first official paying customer um and an amazing story right it's actually all through damien and the reason i'm bringing that up is actually so damien is one of the more understated people we'd be terrible at this we'd be telling everyone all of our contacts and like you know showing off all the time damien just sort of casually does this to be fair you're right it's mostly me um but damien just casually knows the knows these amazing people and does these amazing things because we transfer as a loved brand which is really cool um i remember messaging you a few years ago and like what you up to like when you're back in london let's catch up you're like i'm just at the oscars i was like what you're like send me a photo through of you with an oscar in your hand and i think a cocktail glass the other one i was like what is going on so casual it's an epic story before we get into like any exit chat or anything can you share how damien bradfield won an oscar I didn't win an Oscar alright there we go with the modesty come on how did we transfer to win an Oscar I didn't even know brands could win an Oscar it's amazing so we didn't we facilitated an Oscar in the same way that we facilitated your relationship with Stephen Fry and I think that's what we've been good at that's what we understand really well we enable stuff and it sounds really basic but a file sharing business basically is about sending something from A to B.

36:18And we've been really good at just facilitating that transfer of ideas or that transfer of physical or digital good. The reason we know Stephen is because we had these beautiful images or blank space at the back of WeTransfer. And, you know, I'm British, grew up reading Penguin books. I was like, OK, we've got space to fill. Why don't we give some of it to Penguin and we'll promote some of the new titles coming up. And I thought it was going to be dead simple. Just reach out to Penguin. They'll say, yes, it's free advertising. And we did. I went down to Random House, Penguin Random House, met up with the team.

37:02They were like, yes, I'd love to do that. And I just said, so give me some images then and we'll run them on WeTransfer and we'll just help sell books. They did, but all books are portrait. so all the images they give me were portrait images so we spent fucking months reshooting all these covers of these books so whatever the title was we would create a landscape image but then being somewhat perfectionist we would put it in the setting and context of the book so penguins were like obviously blown out of their mind because we were doing all this for free we're getting paid we're actually spending money on doing this stuff for no reason other than to drive traffic to penguin yeah and um somehow it got to steven's team who went could you do the same for steven fry of course what do you want to do and steven had a new book coming out so we basically just got behind it exactly the same thing went over the top on helping push his new book ended up a book launch with him and um it turned out he was a massive we transfer fan already and loved the product and and that's like the story of we transfer so many people we would want to work with turned out to already use the service unbeknownst to us and particularly from the music industry so i'm getting to the oscar it's a very long-winded story um the oscar comes about because years ago and i want to give credit to the people that have helped us because i always think it's there's a few people that you meet in your life that are very generous with their network i feel like i'm generous with my network but those people that are equally generous i i'll bank them forever and this guy Harris Elliott who's a sort of stylist curator based here in London I knew for a long time he was styling Mark Ronson and Gorillaz and Jamie Hewlett and he introduced us to Eleven Management and Eleven Management was Gorillaz and Jamie Hewlett's Spoke Matambo's management team and we did some stuff with gorillas over the years and 11 management also managed this guy called riz armad who's a spoken word poet and a musician but also an actor and fast forward like 10 years something um riz's team reaches out to us and says riz got an idea for a film um it's about racism and post-brexit britain and again this is like pre-covid yeah pre-covid um you know england's not doing very well there's an awful lot of tension here not that it's that much better today but it's still pretty tense and he said you know would you be interested in helping pull this film together um and we're like of course what should we do i've got a shoot this weekend can we get it going we're like yes and i love this shit so anybody that basically asked me something impossible is okay let's see if we can go out i know that if you go above and beyond and if you really go out of your way you get it back um so that's what we did we put the money up for the film we basically helped Riz pull it all together um we then helped on the the campaign because it's a real campaign to get an Oscar I mean you you win an award somewhere else but then you've got to go and submit it to all these different awards you've got to turn up at certain lunches in LA so we we facilitated all of that and lo and behold ended up winning an Oscar but to be clear it's Riz and Anil that won the Oscar we just did it under the guise of We Transfer and We Present and it runs on We Present and to this day if you haven't watched it it's a very intense 10 minutes very, very intense but it's beautiful and it's the best in my opinion it's like the best of Riz because it's him doing spoken word him acting beautifully it's his casting it's his production and you can just feel this energy coming out of him um yeah it's one of the best things we've ever produced moving on to modern day so a couple of months ago i messaged you i'm like do you want to hang out in london when you're back as i do you're like yep i'm coming sounds good like great started a new podcast with chris actually like redoing secret leaders i'd love to get you on like great that sounds good actually just about to go through an exit process and i was like oh that's that's interesting and then almost immediately you're like it's done the exit is done and when i'd spoken to you well you texted me and said can you can you talk and i was like yeah what now and then you didn't expect me to call you and i love calling people when they just say yeah that's how you know he's almost 50.

41:52he's one of those people that calls you when you whatsapp people that's so weird oh god It's so weird. We're definitely millennials. It's so annoying. It's actually funny how that is so weird. It's such a generational thing, isn't it? Because as soon as he called me, I was like, why do you do this? What's happening back? Please don't. I love it though. He does, yeah. And the more you tell someone it winds you up, the more they're likely to do it as well. So he just always loves the call. But you'd already exited and it was the fastest thing ever. So you said six weeks from start to finish. I was in my local Chinese restaurant getting a spring roll.

42:28And I'm going to afford two now. Maybe. I'll think about the next time. Depends on what it was. But yeah, no, it was the fastest deal of all time. I mean, I'm saying that like I've got statistics to back it up. Could be. I have less context, right? So we tried to IPO that we didn't get there in the end. And so from that period to the exit, how long were we talking? And we basically had a conversation and said, okay, there's a horizon. There's going to have to be a deal of some sort. I mean, there's obviously different flavors that could happen. And that's where your VC is, right? It's the investment company.

43:11The board team, management team. I was like, yeah, okay, there has to be an acquisition or an exit of some sort.

43:21And sort of casually at a dinner, actually, one of the VCs said, what would you think of this company bending spoons? And I don't know them, never heard of them. So they might be interested, so I'll have a chat with them. And that was like casually sort of thrown at the table like, you know, as in, you know, what do you think of that girl? It's all right. And then the process seemingly had already started. Wow. So they seemingly had already started doing due diligence and had commissioned McKinsey, who were doing some research on us.

43:53and basically within within the space of six weeks it went from hey they might you know maybe there's someone that's interested in dating you to you've been sold um how much of a say did you get in that process very little yeah are you able to say no and they're like okay understand your objection but we're doing it anyway or is it like i mean that's a very common conversation huh that's a very common conversation in our company yeah fair um i mean that's a very common conversation in any company that's heavily invested in yeah you say we we don't want to do this they go thanks for your opinion we'll be cracking ahead but can you communicate to the team yeah and i mean the i mean fortuitously for um the acquirers you know an awful lot of homework had already been done i mean if you're preparing for an ipo you're in tip-top condition like you You know, you can't, there's nothing being scraped under the carpet and, you know, buried away that somebody may not find out.

44:50If you're going to IPO, then you're in really good shape. Yeah. Or at least everything. And as you're a crypto company. Because a lot of those made it. Or buried in some sort of SPAC. Yeah, exactly. You know, if you're going onto the, you know, the Amsterdam Stock Exchange and you're going to bear everything, it doesn't all have to be pretty, but it's going to be pretty transparent. Right. So we were in really good shape. So they didn't, you know, we could basically just go, all right, here's a folder of everything you need to know and get on with it. So it was locked and loaded in six weeks. I mean, if anyone can deliver a comprehensive folder with all the data in it, it'd be you.

45:29You'd hope. True. Yeah. So you'd hope. Yeah, it'd be really off-brand, really off-brand if you fuck that up. Yeah. So the conversation at dinner happened six weeks later. I think it will happen on Dropbox too, by the way. No, that's just insulting. that's just rude it always does actually when it comes to financials it's always like doc send or really yeah i think so yeah fuck you off just to trigger you maybe just rub it in it's like there's still plenty of room for you guys to improve you guys should get corporate um just out of i mean yeah just to one of the things the comparisons i just like to say as you've said this isn't like doc send or doc you sign one there's a multi-billion dollar company and every time you their product you're like is this it it's insane and yet on the other side you've obviously got the we transfer so we like beautiful brands so many users all that kind of stuff and like struggling to tell the same story maybe because more of a consumer product potentially than b2b yeah i mean our our users are mainly you know small creatives freelancers agencies we don't really have a corporate offering i don't know what docu sign costs but right it's probably like minimum 100 bucks a month or something like that i don't know I mean it works right I mean you guys probably use it we use it all the time I've got a question for you who the fuck are bending spoons if you're not googling them I've done any research we've got a team of like 100 people I genuinely I genuinely know so little about them yeah I wasn't briefed by Jay Jay should have briefed me god damn it Jay Jay who's bending spoons

47:03good wow are you really selling it Jesus. Excellent. Is that what you really Googled, Jay? Oh, yeah. Are you doing it right now, real time? Nice. Is that ChatGPT or Google? That's just my own research on Google. I chatGPT, secret leaders. How many listeners you got a month? We don't talk about that right now. We're talking to you. We're in a transition right now. We're talking to you about Bending Spoons. How would you describe Bending Spoons? As in, what are they known? like to me like we transfers super famous brand and i'll say like is bending spoons a holding company with other brands in it or what's the vibe so i hadn't heard of bending spoons either until it was it was casually thrown the table this dinner um it's an italian company i mean seemingly well respected in italy they they've been around quite a long time building some products but mostly acquiring products um they i guess i mean i'm an agency guy right so in the like in the scheme of things it's a bit like wpp it's a company that acquires um brands companies in and around the sort of creative um producer space they quiet i mean quite impressively actually um luca who's the ceo in between getting married and going on his and we transfer um and so gosh i think to be fair i was a sick operator that's amazing yeah of course yeah i do remember issue um yeah so i mean in the space of two weeks closed two deals i mean um pretty impressive and prior to that they'd acquired evernote and quite prior to that they'd acquired an AI tool, which...

48:51So actually building up quite a cool portfolio, to be fair. These aren't, you know, these are actually interesting internet businesses together, like when put together. I mean, I haven't used Issue for a long time, but there was a period where it was sort of like the publishing platform of the internet. For sure. If you are going to be condenased and you're going to have a digital magazine, you'd probably push it out on Issue too. Yeah. So I don't know anything about them. I don't know any of the financials, but you know it was quite iconic I guess at the time Evernote the same yeah I'm sure you know definitely iconic yeah you guys would have used it and we transfer as iconic that's kind of I mean I guess Italian right they've got good taste so bright buying proper brands yeah yeah yeah but I didn't know much about them you know I still to be frank I don't know much about them either you know we our relationship is very fresh and new and I'm learning you know on a daily basis is what it is that they want and what they plan to do.

49:50My hope is that, as you say, WeTransfer is an iconic brand. My hope is that they respect it and build it

50:00and continue to sort of keep its place in internet history. I think it's got a place. I love looking back on the Wayback Machine and seeing WeTransfer in 2010 and 2012 So it's quite cool. Obviously, like the exit process being so fast, you say you don't have that much say in the matter, etc. Like no say, it's like votes. So kind of, it just happens. Well, I suppose context is important, right? For that to be the case, you must, your ownership must have been a certain level. Yeah. The investor's ownership must have been a certain level. Exactly. So, you know, Highlander is the majority owner. Right.

50:39And, you know, as these things go, you have drag and tag clauses. so I guess we could have gone through the sort of formal process of who's in favour who's not but it wasn't necessary it was very clear what was wanted and these guys were willing to pay what everyone was looking for yeah and I presume for Highland it is as simple as did we make X on our money if we do we're out I mean Highland has done very well from it as a as a VC shop I think they've done really well I think they've had some really big exits in the last few years and they've gone on to launch you know really big fund over the last year or the year before so they you know they have a really good track record and I think for them WeTransfer is a really good exit.

51:30How do you feel about it then? What Highland the exit? No yeah how do you feel about the exit both financially and emotionally um well it's still very raw right so i'm i'm doing this in in real time um yeah so i just happened yeah yeah yeah so i'm i'm processing and talking and processing at the same time so what you asked me this week was very different last week and it'll probably be different next week um i'm i've i'm resided to the the conclusion that we've arrived at then i know i knew this was going to happen i knew this is what it was going to be um i would have loved for it to be different um and i'm sad to some degree that um You know, it's the end of a road.

52:25I've also done it 15 years, and I've, you know, I've had struggles with it in the past. It hasn't always been easy. You know, certainly the last couple of years has been quite stressful.

52:39And maybe it was time for me to move on anyway. There's a certain point, and this is contradictory to where we started, but there's a certain point in the company that you do hear yourself saying, we've done all that. We've done that before. we tried that already that didn't work out and I could hear myself sort of sounding like that old curmudgeon in the corners like that's not going to work is it look at these young kids trying to do what we did before you don't want to be in that position where you're just um slightly you know jaded yeah old and a bit irritated and um and sometimes I could hear myself being that person through irritating yourself sometimes yeah and many people around me um but then you know we still I hadn't finished so I don't know if you ever finish but I certainly felt like I wasn't finished so there were still plenty of things on the list to make this thing bigger and better we have many moving parts we present Is This Arts platform that's loved by many but still not known by many I would have loved to have seen that heavily integrated and really built into WeTransfer as you said we're one of the world's biggest b corps in tech most people don't know that and i really think in terms of the service we could have done a lot to you know add value to the experience and do good for the planet at the same time without having to ask people to pay to do it but just doing it by encouraging people to delete files reducing server emissions you know that sort of thing so there are loads of things i would like to have done but if i'd been doing it 70 years maybe i'd still be saying that so So yeah, I'm in a bit of a discovery phase and the company is going to go through a lot of change.

54:23And that's also quite hard to witness. So it's very mixed feelings. Most founders, when they exit their company, well, we were discussing this. Not necessarily most, but we definitely talked about the fact that a lot of founders would like to leave their company once they exit it. like realistically it's just going to be super painful super challenging you're now working for someone you're not necessarily aligned the whole earn out thing feels like breadcrumbs and begging for your cash kind of thing what was your situation i mean super mixed so if i think back actually i resigned halfway through the process i got so annoyed that i resigned and then sale process Yeah.