FOUNDER #7. £90M Sale to Adobe & What It Really Takes To Scale A Business - Alex Packham

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1:42Raised$14 million, grew it to 5 ,000 plus global customers, and then 2021 sold that to Adobe. And you end up selling it for$110 million. dollars. Having been a social media manager and I used all the platforms at the time, but none of them had a calendar. And I found, particularly in technology businesses, the best products are created from scratching your own itch. The phrase is, you're looking for a market of want. Most people are going to say no. And so you get one, all the other ones want to come in. You're going to just have to deal with the rejection. Where were you when you signed the deal and you knew the money hit your bank?

2:15I actually had a huge, huge identity crisis and actually went into a period of depression when that happens to you nothing changes but everything changes your mentality or mind certainly did anyway changes massively to well now what the f*** am I working for Alex are you happy what are you doing today today I'm running Jack 30 % of people in their life go through a mental health challenge but that might be depression might be ADHD it might be might just be sleep Jack can reach that many people and positively impact that many people to be happy you have to know who you are so i really believe in it and it's got you know all the legs to go all the way what a journey it's crazy do you know another crazy thing about that hey people i'm dodge host of the founder show i've been an entrepreneur all my life and over the last three decades i founded five businesses in the world of media festivals sport tech live events and i've been lucky enough to have sold two of them i promise this isn't your normal boring fluffy business podcast this is real and raw with a lot of emotion i'll delve deep into the guests minds on the risks and roller coaster journey of being an entrepreneur.

3:18I hope you enjoy Alex welcome to the show. Thanks so much for having me on. Yeah I'm really looking forward to this one. Let's start with who is Alex Packham and what's been your biggest business achievement so far? Who is Alex Packham? I have so many different versions of answering that question I'm sure most people do. So in the business world I'm Alex serial entrepreneur. My biggest achievement I think in the business world was founding a business called Content Cal short for Content Calendar I basically got on to social media marketing really really early before people were really using it for business so my entire background came from learning how to use social media for whether you're a big company small company how to use it for the business context and that was back in like 2000 2008 which feels like a long time ago but I was in the first cohort of people basically that in the UK realized Facebook in particular at the time was an incredibly powerful tool, not just for us to connect as people, but for businesses to promote themselves.

4:19So I spent, I'll give you the full story as we chat, I'm sure, but 10 years embedded in the social media world in and around business, ran Odeon Cinema social media for two years, ran Now TV social media for two years, set up a social media agency, running those two as clients and then many, many others. and then I morphed that agency business running different client social media accounts into a software platform called ContentCal. And then I went on a six-year journey kind of in that business raised 14 million dollars grew it to 5 ,000 plus global customers team of just over 100 and then 2021 sold that to Adobe and so yeah it was a wild ride just like that.

4:56Fantastic yeah well that's the end of that podcast. Mate that's amazing journey yeah. So 2008 how old were you in 2008 roughly? I was, uh, how old was it in 2008? 18, 19. 18, 19. And when was it when you first set up? You obviously worked for a couple of years before learning the trade, working for social media, being the social media manager for those companies, I'd imagine. Well, what I did was, uh, I was going to actually, literally, I've got a semi-photographic memory. I can actually remember the moment I figured this out. I was actually at uni, so I was 19 thinking about this. Was you uni, 2019?

5:23I went to Cardiff Uni. Okay. um and i literally realized everything i was buying as a student or the bars and clubs i'd go to or whatever it might be were influenced by what my mates were doing on facebook or what a brand would start to share on facebook and i was like i'm not watching tv i don't watch tv and that i don't watch tv now do i not linear no one does these days right yeah well exactly yeah but it was all that generation where all that stuff was super new and i literally was on my laptop and i was like this is going to be huge and i went down a rabbit hole like and this is what quite often i do if I get into something rabbit hole on the laptop as a 19 year old in Cardiff.

5:58And then this concept of social media marketing again, which is obviously now massive, but was brand new. And there was the Gary Vaynerchuk's of the world and all that kind of stuff talking about it over in the States, but no one was really talking about it in the UK. And so actually when I first started, I was 19 as a student doing social media management from my bedroom, uh, rather than studying, making money, figuring it out, making it up as you go, as we all do. And then, you know, And I finished university, kept doing that on the side. And then that's when I went into Odeon, which is my first proper gig doing it.

6:24Okay. Do you remember how much you were on at Odeon? Oh, my God. Like 25K? Okay. But it was weird because, one, these jobs were new. Like, this didn't exist. The word social media management or this kind of job, social content creator, did not exist. That's right. And there's a guy who I'm really good friends with now at Odeon. He was in sales in the business side. and he would come around and kick the back of my desk and um be like um i um yeah i'm getting paid to be on facebook basically like completely taking the piss out of me like i'm actually doing a real sales job over here and you're just sitting on facebook like you know messing around but yeah i spent i spent two years there doing that and then um i hopped ship to now tv when that was brand new but it was kind of a subset of sky's business um did that for two years as well and that's when i realized corporate just wasn't for me and again we go down the journey but it was amazing because these businesses were learning how to do social media through people who are 23 22 whatever it was who are living and breathing it living and breathing yeah yeah yeah what was the point where you said right i've had enough of working for a corporate i need to go and do this myself for me it was basically when so now tv which is quite a big brand in the uk now right like and netflix in the uk when i went to sky it was 40 people in a room figuring out how to build an internet uh kind of sky business basically for them because netflix had just landed in the uk sky had reached a time where actually there wasn't a huge amount of growth in the kind of typical set-top box type stuff and i spent two years there and i i had a wild ride it was a it was a corporate business right but actually a startup within it 40 people to 2000 in i don't know 18 months my god what now tv huge growth this was a london you know in um australia which is sky's office is just sky's huge office but we got chucked in like the shit is yeah okay in the whole building like go and make it work literally go and make it work and we did but what i realized was when it got to like that 2000 or whatever the number was people we got a little bit more embedded into the actual sky company culture all i could see was okay the only way for me to either make more money grow my career is to basically network in sky for the next 20 years of my life and maybe someone else will decide if i'm good enough for a promotion for a promo yeah and i was like fuck this yeah um i'd always wanted to be an entrepreneur i always thought i could do this um and the moment i decided to do it again i can remember it picture perfect i was in portugal on a family holiday i read two books the lean startup and tim ferris for our work week and i closed the book i turned around to my mum and uh just said mom i'm gonna go i'm gonna quit my job and i'm gonna uh start this business that i've been thinking about um and she was like no you just started your career basically and i was so young but hey it worked out in the end i'm like fuck this i'm gonna go and do it yeah good for you yeah what did you call it the agency agency i kept it very simple it was actually i think somewhere on this hat astp it's my initials yeah back in the day the i was very embedded in marketing culture agencies were like very cool upfront brands but they were quite often started by like one or two people in a room very similar to how i started right and just said right we can do this ourselves um and i really didn't want to go around the houses on names and i just wanted to get something off the ground to be honest at the start it was just me so i was like let's just call it my initials no one's ever going to ask what that really means and i didn't really overthink it but interestingly as i built whether it was the agency and then in time content cal and now many other brands branding is obviously so so important so that morphed you know over two years like i said into content cal but it kind of gave um it gave me a personal brand which we were talking about before we started press and play here like using your initials or using your name it gave me the ability to become credible in the space just you know my name intrinsically linked with the the agency but there's a pro and a con to that because then there's 100 % reliant on you and agency businesses services businesses are often reliant on a couple of really good people and then you've got the team underneath and it's harder to sell very hard to sell when you've got your name attached to it oh yeah very hard i've always been a person who's always stepped away from the business come up the idea created created and step away and put people in place just for that accessibility of when the sale comes you're you're not attached to it 100 yeah and um i learned that that way you know that's actually when we made the shift to a content calendar and kind of morphed the business into a software business i was like it's not the alex packham show yeah like this is a business this is a brand where did you where did you find the idea then because when we're all creating as entrepreneurs i'm always looking for a problem somewhere yeah can i solve a problem can i get paid for that what's pissing me off about this problem can i get paid well you know you're always thinking about that where was it when you come up the idea again you know what i've actually found a real problem here i'm going to create content cow and this is what i'm going to work on so having been a social media manager having been the person who also writes the posts create the posts responds to people thinks about a content calendar you know outside of our name like what am i going to post over the next month i did all of the jobs in social media like physically lived them and i used all the platforms at the time so back in the day it would have been like a hootsuite or a buffer hootsuite is the one wasn't it yeah it's still big it's still big um but none of them had and it sounds so simple yeah a calendar they none of them had a calendar at the heart of it so you're like thinking about what day am i going to post this and it was all about scheduling in the future but there was no interface of a calendar and so i spent a lot of my time and then i as i met more social media managers going on to excel or google sheets making calendars to write the posts to send it to the agency or send it to my boss or whatever it might be to get approvals tweaks and changes so the whole process was actually in a spreadsheet and then you take it to a product and like then you plug it in for scheduling and planning or whatever and my view was you know there's there's me there's however many social media managers in the uk and i also knew just embedding in the industry right like this personal brand or this creative vibe has unfolded massively over the last 10-15 years i knew it would be coming yeah everybody's going to want to be a publisher in some way shape or form at some point um and so i just literally sketched out my perfect product for myself mine was calendar interface start there so that you can go from ideation creating the post putting the schedule together in the calendar visualizing it if i've got to send it to someone building an approval process in the product uh building analytics so actually i'm going to go to another platform to look at analytics i was like how do we bring this end-to-end process into one physical place and i made it for myself and i found particularly in technology businesses you the best products are created from scratching your own itch and i literally sketched it met a friend of mine eventually through meeting different designers gave him this literal set of scribbles and i was like i need you to make this beautiful for me and he came back two days later and he just became my like kindred spirit between me as ideas and him as design designed it and i was like you've nailed it like this is going to change what a feeling it's fucking amazing what a feeling knowing that you saw a gap in the market that Hootsuite and the other brand weren't nailing for you to go you know I can nail this by doing a calendar but if I remember rightly didn't Hootsuite allow you to do it for Instagram yeah Facebook but not not on TikTok or not on Twitter it was something that didn't incorporate everything is that right yeah correct yeah everyone had different access to different levels of platforms at different times depending on how fast you integrated them uh again none of them had the ability to actually see it all in one place and visualize it and that was our thing like we want the end-to-end process all in one place we don't want to just just manage scheduling Hootsuite was super popular for basically the scheduling part and the interesting part was and this is why I love entrepreneurship Hootsuite at the time all these other businesses super well funded they were much much bigger than ContentCal was but we as some dude in the UK and you know a band of people together were able to disrupt from a user interface perspective the entire way these systems are now set up that they all then whether they copied us or someone who then copied us everyone copies everything yeah it's best form of flattery yeah it pisses you off for first time you see it does you're like i know you but i've done it to someone else yeah exactly yeah but yeah no but you know that's the bit i love about it we we were able to change an industry and uh that's how i i think about things going forward quite a lot like finding the the thing you know and then ideas are super important in business execution is obviously way more important but you're finding the thing that gets the hook and for us honestly it sounds so simple it was a calendar yeah yeah so when you when you come up with that idea how did you scale your business how long was it for from the start of content cow until you sold how many years was that um it was six years as a pure software business and two years before that as the agency so eight call it eight and call it eight years okay and did you actually sell the agency or did you sell content cow i sold content cow yeah the agency kind of morphed into it basically kind of over time we said right we're going to stop managing clients accounts and honing on this so it's sort of like that was growing uh the software business the revenue groups more slowly in the software business in theory then that overtook it and then we're like right we're down towards that part of the business yeah so when you were doing content care how much were you charging the customer so we went out initially thinking we're going to be like an enterprise sales tool like 40 50 grand a year 100k a year whatever it was this is how i get a lot about pricing we then ended up actually charging on average i think like $49 a month.

15:14Yeah. Okay. And it wasn't like we're going to have, um, a hundred customers at a hundred K or whatever. It was like, we're going to have thousands, thousands. Yeah. Yeah. Yeah. And it took us, it took us two years to figure that out. You know what it's like in the early days, you don't have a clue what you're doing and it is all testing and learning unless you've built a business, gone through the whole journey and all that stuff. I was 23 to 31. That's kind of the, you know, 23, 24 to 31. And so you, you are learning everything, pricing, sales, strategy, finance raising money corporate finance hiring firing talent so that period of my life and that was one of my personal goals was like how do i take 20 years of work and cram it into my 20s so that by the time i'm 31 32 whatever even if content cal doesn't work out i have learned so much yeah that my value can then go into something else yeah um so it took that long but like i'd say the way my journey compounded was in the first two or three years like i said you're in the you're in the sticks right and you're kind of in the trenches absolutely battling everything out whether it's like pricing sales strategy you learn so much but with software businesses as you you get traction and because it's recurring revenue right so you're not like having to do one sale and then that's it it's like right 49 months then you're over for a year and then you've got another one then another it compounds over time so every year you start with whatever your last year's recurring revenue So we started to see that and feel that in the first two or three years.

16:39So by year three, you're like, okay, there is some formula. Yeah, exactly. When you come up with the idea of ContentCal, how many staff were working on that from day one? It was yourself plus? Me and one other. Okay. And then a handful of developers that I'd managed to just persuade to do some stuff for free. Okay. And then when we got it into what I call a mini business at the start, there was probably me, a designer, call it three or four engineers. and then we had one guy join us really early in a growth sales capacity yeah and i had to learn that actually in that business i was really good at selling in the agency business because i was selling me yeah in the software world i didn't have a clue how to sell so i had to bring in a chap i got introduced to one of our early investors called andy lambert and he was a software salesperson and he was like an alien to me he was like i will go and talk to everyone yeah and you know just talk about this and i was like oh i'm so not used to that like i would be a bit more you introduce me we'll have a conversation maybe the business yeah he's like no i'm gonna go into every room about do you like this or not do you want to buy at this price point what do you think and he just did that over and over again so he really for me was someone who we bought in who had all the energy in the world but also was just like i get sales this is my world leave me to it kind of thing yeah how much money did you have to put into that content cow for the first two three years we raised in the first two or three years about about 2.6 million oh so you raised straight away did you yeah how could you not afford to at the time could you afford to get it to a certain point how long did you get it to that point before you raised so before we raised any money properly i used the profits from the agency so let's call it i would you know what are the numbers probably about 100k of agency profits went into the design the mvp etc and that was just money you know we had yeah and then from that point i started to realize that to actually do this and this was a while ago this is before technology well certainly i had a clue about how to build tech but also you didn't have the power of ai to do half your coding for you and all that stuff so we then raised 150k from friends and family but you know some some family of mine luckily were able to invest but then i had to go and you know meet a bunch of strangers and raise cash so we put 150k on top of the hundreds call it 250 to get it like working yeah and that wasn't well that was a really good prototype i'd call it but then we had sky using it and odin cinema is using it and all the agency clients he had like 30 customers from day one um as soon as i got through that bit i then realized okay if i'm going to do this properly i need to understand how to build like great technology and raise money because as we all know and everybody reads it and you know if you're in the tech space you kind of get it but actually from a lot of people's perspectives externally they're like why can you raise all this money burn all this money and then still sell a business for lots of money wild isn't it it is wild i mean i've lived it so i understand how it works but um i spent in the next you know three five years whatever it was really learning how that that bit of it works the finance bit because it's totally different to other businesses how did you approach your friends and family to raise a ton 50 um i am very lucky in that my mum is one of six and my granddad so her dad and my aunts and uncles particularly my uncles were incredibly entrepreneurial yeah and or very business orientated so from probably 14 i've been around people that ran their own businesses uh or very ambitious um very business focused not necessarily wildly successful but were fucking hungry yeah and so um my one of my uncles steven lane who's actually a really good friend of mine runs another business called prop store which is a brilliant business totally separate to content cal uh which we love but um he that he said to me when i was he mentored me when i was really young sort of 16, you know, just in different ways in life.

20:19And he cut me my first 5K check. You know, he believed in me. He could see it. He's an entrepreneur himself. He was like, Alex has, you know. He's got something. Yeah. But also, actually, he was like, I'm just going to back Alex. Yeah. You know, and that spoke to me. I'm actually thinking about it now. I can feel it. Like, that spoke to me so much. It wasn't actually like I'm investing in Content Cal or the agency. It was like, I'm investing in Alex. Yeah, yeah, I love him. Yeah. What's his name? Stephen Lane. And he's a legend. Yeah. Big shout out to Stephen. You're a legend. Yeah, yeah. But they're the things that really matter most in business, the people who back you and give you self-belief.

20:49You know, that's going to stick with you for life. It literally does. And I'm sure that 5G's, he's had a nice little, been looked after as well, you know? He did very well. Yeah, I'm sure he did. I'm sure he did. But he backed me all the way. Yeah. And there's many people, there's a chap called Derek Jones who backed me again. He was a complete stranger to me. He ran a business called MediaTel. I've been countless, Colin Smith, James Murray. There's a bunch of people in my life who literally, like you say, and a lot of those people I'm talking about and there's 30 old angel investors in ContentCal, they don't know who I am.

21:17I'm a dude, a kid at the time really, who came in, pitched them an idea, met them for a coffee most of the time, chit-chat, and literally within a week, they were like, yeah, here you go, here's 50K, here's 40K. But I came with a lot of energy and I knew my space. And I can only say that with hindsight because to me, I was sort of winging it really. Well, we're all winging it. We are. We're all winging it. It's just the self-belief and the confidence. Which you have with youth as well. As you get older, that not necessarily goes away, but you get more bumps along the way, right? I didn't really have any bumps at that point, to be honest.

21:44I was lucky, and I definitely did later. So that ton 50 there that you got invested, how many shares did you have to give away for that initial 150 grand? Probably a give or take, I think it was like 8 % or 9 % of the business. Okay. And we definitely didn't raise money in the perfect way. I didn't even know how to do it, right? No. So nowadays you'd go, whatever you're raising, say, you'd go, basically you're going to give away roughly like 10 % to 20%, let's just say, based on the VC round or whatever, typically through the flow. Or an angel. We're not doing angel first? I did angel first, but I was just saying now if you do it, that's kind of what happens now.

22:15It's pretty well modeled. You don't negotiate that much and stuff as much as people make it. It's like, right, we're raising a million quid and it's 20%. At that point, it was angel investors. And I was doing the, or people thought they were doing the dragons and I'll give you this for five billion. I'm like, fucking bullshit. Honestly, it's ridiculous. But, you know, it does teach you some negotiation skills. But, yeah, so I gave away, let's just call it about 8 % to 10 % in that round. And then there was a few versions like that over time where that continued. of which from angels we raised about 2.6 million.

22:46And then we got into venture capital just before COVID. So we kind of built the business over, say, must have been 2016 to 2019. So that three years I'm talking about, we're doing it. Okay, more angel investors. More angels. So 8 % or 9 % for the first time, 50%. How much did you raise in angel investors before you went to VC? 2.6 % in angel. And then we raised 2.5 % from a fund called Fuel Ventures in 2020. After angels investors. After, yeah. Okay. 2.6 % in angel. What did you have to give away of that 2.6? What percent? Probably in the round, probably about 25, 26, 27%, something like that.

23:23Just under 30. Okay. And actually, so if you do it in a total calc, if I'd have raised that in one go, that's probably what you would have given away anyway. Yeah. But I did it over three years piecemeal because, again, I wasn't credible to a VC. Still learning? Yeah, I was still learning. So you'd given away 30 % before a VC come on board? Yeah. Okay. And did you feel totally comfortable at that point? i did because i my my thing with content cal and to be honest with pretty much any business i look at that can scale massively was like this is not my this is my baby in one version of my world i love it i'm doing it etc i've always been very much like and especially at that point like this is a bet this is a transactional bet for me that i fucking believe in but it's not my it's not my be on end or to build a really big business there are very few people who own you know actually over like six seven eight nine percent in time but the bet is to get it so big that that is worth you know enough to financially right yeah so that was my concept i wasn't really like crazily precious about necessarily what i had obviously you have to be super smart about how you dilute later stages and stuff like that but i wanted to build it you know my goal was as much of the money side of it was actually i want to learn i want to do this i'm doing it at a young enough age and see what happens yeah yeah love it yeah love it so when you when you went from angels how many people were you juggling then so you'd raise a ton 50 then you raised say two and a half you're all in for two 2.6 say for argument's sake how many people you're actually juggling investors or yeah investors uh we had at that point when we got to the peak of angels probably about 30 different angel investors and how's that for you juggling 30 investors they're all saying i put 100 grand what's happening is it all going well or is everyone fully supportive or were there some people going alex come on mate i need a return on this money do you know what everyone was in the supportive camp brilliant and obviously i've now invested in 60 different companies so you have okay yeah so you know i know the announce yeah i was not whether it was luck whether it was just the right people whether i was i was actually pretty good which is i do look back and you know i kept them up to date and stuff like that i didn't have touch wood really once they touch wood has already happened but like any dissenters any people going where's my where's my return yeah it was all like we've given the cash we're backing you let's have it yeah exactly yeah and the best calls i got to give to people was thank you very much for investing 50k we're about to sell this business for this i've just made you a fucking fortune and i i've got videos of me doing so many people and the reaction you know every reaction because i was like hi whoever uh how you doing i haven't spoken to you for a while because at that point we had vc yeah a lot of the angels weren't as involved are you sitting down are you all right how you doing oh yeah so i've just done a deal with to sell and you just hear everyone just go oh fucking yeah oh this is amazing when does it happen you know i obviously couldn't see the mic it was just so funny yeah it was a lovely story yeah yeah yeah so so when we got through the angel investors now you're juggling 30 people you're obviously a very good communicator i can see that thank you and you're good juggling people and you've got a nice bubbly vibe about you which people will love when you go into the vc world how's that different to the angel world well it is one way of it is incredibly different and actually some of it's very similar so vcs one they're investing other people's money so they have a mandate to do something which is very different to angels an angel can go i've got the cash it's my money i can make a decision do i like you yes or no done a vc is i've got this much money that i've raised from other people they want a return of x whatever x is and we promised them that basically we only invest in companies that look like this at this stage whatever it might be so there's a whole set of very strict criteria and if you fit those criteria in boxes and then you go through all the pitch process and the investment committee and you pass due diligence and all that stuff that they have to do because they are investing other people's money um it's highly transactional in that that way of thinking right so you know i went to a couple of vcs and some vcs are great and some are terrible that they'll string you along some will just say it's not for us you know all that i prefer those ones the ones that just go straight it is not for me thank you very much good luck fast yes fast no is what i said to everyone um but basically the the transactional element is transactional do you fit our criteria yes does it fit what we want to invest in do we like you are you at the right stage are you raising the right amount of money tick tick tick tick if this crosses whatever but tick tick tick do a deal um however they are human beings and so what i found with venture capital investors which a lot of people go oh god when you have a vc and aren't they just a pain in the ass and then they try and tell you what to do and they've got all these restrictions well actually on paper some of that is potentially true they've got some rules and regs around what they not necessarily allow you to do but stuff that they need to be informed of in the business because you know they're managing other people's investments if you go for lunch with them or you have a coffee or you speak to them normally rather than being in sales mode all the time and you build a relationship like anything else the person who's on your account so to speak or on your board on behalf of the investor fund is a human being and also bear in mind they haven't invested in you because they want you to fuck it up and fail they've invested in you because they believe in you survival and then you look there's there's difficult conversations that happen you know when things are going well and things aren't especially as well but actually it's a it's a it's a very business-based transactional thing that you're doing you know you are one bet of their portfolio of 10 20 30 40 100 plus businesses and so as soon as you my main thing with everything is you learn the rules of the game you understand the game that they're playing you understand the game that you're playing and all is fair in love and war so there was no like you hear of these vcs horror stories there was there no part of you like i'm not actually enjoying this part of the journey oh no i had loads of that yeah okay okay okay i mean i'll give you an example so we when we were morphing from the agency to the software business we still had a i don't have many staff but a payroll of the agency business call it like i think it wasn't that massive but it was to me at the time 30k on payroll a month yeah call it a month yeah what are you talking seven eight staff something like that maybe maybe 10 yeah okay uh we had a uh basically no money in the bank let's just say realistically but we had on the same day payroll was coming in 40 grand like an invoice from 40 grand i remember waking up on the day that that invoice was going to land i.e the day that our payroll was supposed to go out and it was like 6 a.m and the 40k hadn't arrived and i was like oh fuck yeah that money is not in the bank as and i didn't actually have money to pay people and i was watching my phone like on my banking like oh shit is this is this going to come in because if it doesn't i am fucked um and i would never do that now obviously and then literally like four minutes later it was their payroll was great you know all that stuff stuff but um fucking hell like the stress of that that is actually like and it was like half an hour but it felt like five days watching my banking so i've had that those types of moments i've had times where actually before we raised vc we'd burn through quite a lot of our runway we knew the well the investment the vc investment from fuel ventures was coming what happens right in the middle of that covid pandemic yeah okay fucking every vc even if they'd written term sheets to do investments pulled out yeah okay and shiv who's a legend and mark pearson who runs fuel ventures i remember being in the we actually shared an office with them for a bit like for number one what the hell is going on in the world but number two is are we still good and they were like we're in they still this is this is happening like and also you don't ever you know no matter what you signed any deal you do until the money's in the bank exactly but they were like the whole way we're in very communicative money came in i remember actually that again i've got photographic memory waterloo i was in waterloo station kind of going home you know it was like desolate there was like no one there and i was just like thank god again but now we go and so i've had tons of moments like that where you're just like oh man this is hard this is hard this is really hard and many later in my career which we can talk about as well but there are the biggest highs and the biggest lows in building businesses from scratch and i think that zero to one phase probably has the biggest highs and the biggest lows actually zero to one building something from scratch yeah what's the one great that's kind of getting it to whatever the stage you consider to be i'm in the game okay the kind of zero bit is like we're starting out chaos it's a scribble to whatever yeah yeah i love the chaos do you oh i love the guy yeah i love building businesses which bit do you like so if i said it was zero to one phase that is the starting this from nothing yeah something the chaos do you i love i love all of that really yeah i'm addicted to that i'm i i i'm addicted to risk really yeah i love risks i know in fact i only found out that my wife knows my big risk taker my friends know i'm a big risk taker but i was in the world of business elsewhere as well or not everywhere everywhere really yeah yeah i'm also business yeah but i was on stage talking last month and someone's talking about talking about addiction and i was like no i'm not doing i've got friends with addicts yeah yeah podcast yeah this woman put her hand up i said i've been following you for a few months i think you are you are an addict I went okay well thank you what you're a risk addict I went shit you're right yeah I enjoy the risk I enjoy the gamble I enjoy the chaos I enjoy working it all out I enjoy looking where we can get staff pull staff in from I enjoy I just enjoy the game yeah here's a tip for you there's a podcast out there with fans waiting to be your next customer they tune in every week they trust the host, and that host wants to talk about brands like yours in their own words to their audience.

32:48The problem is, you just haven't been introduced yet. We're Acast, where that introduction happens. As the world's largest podcast marketplace, we let you browse shows, see who's listening, and book host-read sponsorships or run your own ads all from one platform. Transparent pricing, real-time data, complete control. Start advertising on podcasts by visiting acast.com slash advertise see the game yeah and you answer this do you think it's the money part of it or is it the problem solving or is it the problem solving linked to the financial outcome it's the problem solving linked to the financial outcome yeah like in in the different eras i've been in the younger years it was about earning money i wanted to have money yeah i wanted money yeah i've got no no shame about that in my 20s i wanted in my teens although i wanted money to live a nicer lifestyle yeah but when you get to a certain point in life when money's not the main goal yeah yeah it change it changes your outlook on creating businesses because you've got money behind you to create businesses and you could take more risk you can take more risk you know no i totally get it yeah but you know this i've gambled the family house on things and really Yeah, putting on businesses, festival and whatever.

34:06But I love the game. So that 0-1, so you've then come into the VC world. How long was it? How do you sell it to the VC world? Guys, I've burnt through another two and a half mil, and now we need more money. Is that pretty much the chat? Not quite. So, again, I learned this in the journey. You put together a pitch deck. You can find these online. it's got who we are the problem solution the total addressable market you do the pitch whatever it is however that comes up i actually um did a pitch event and then i just happened to be sitting next to a guy from who invested in us and he's like love the idea of the business let's come and chat to these people you then have one or three meetings you then kind of go through a process of what i'd call mini due diligence do we like this do we not have we vetted alex etc um your question was like how does it work basically yeah basis it's it's effectively it's a sales process so i've i've been in one or two or several discussions basically conveyed enough to them that content cal is a great idea we've got validation we had just under a million of revenue at that point bear in mind recurring revenue yeah so we had we were not we're not so how many customers roughly would you have had then if you worked it back in the nine quid and no well it was all different pricing at that point so we had a few at 50k if you were you know 200 grand of that but i don't know call it call it 200 customers okay 300 customers so we had traction so you had 200 customers leading up to the vc money yeah okay yeah so they could see the business model working yeah exactly yeah most big vcs so now they call it like pre-seed seed series a yada yada yada again these stages exist but they were less well formed when i was raising but we were what i'd call a um seed plus we were just before a series a but a seed plus investment there was enough proof points that we had de-risked the bet slightly okay to your point still lots of risk involved but um we had enough proof points they believed in me they believed in the business good investors on board good customer names you know look at logos have you got big brands which we did etc good team even though it's still early they're just they have a tick list basically and you go like that and if you miss a big one they're not going to do it even if you've got a little amber light on one of them can we fix that i think so yeah yeah all that kind of stuff so that that's the process it's like what i would call it if anyone works in like enterprise sales it's very similar to that you've got a target list of people you all go to have the initial conversations give them the right information at the right times bring them through that sales funnel and you're looking i often phrase the phrase is you're looking for a market of one yeah you need one person to say yes most people are going to say no and so you get one all the other ones want to come in yeah that's how it goes basically how many vcs did you approach before you got someone to say yes we're in probably over 100 in in ingested in London.

36:46Is that right? I got every no on earth and Fuel Ventures was my one yes. And that's why I love them. Wow, I bet you do. Yeah. So any founder out there, anyone looking for VC money, the proof in the pudding here is you're out there throwing everything against the wall to see if one thing that sticks, someone who actually believes in you. Out of the hundred, for example, are you presenting to them or is that an email with the presentation there going, guys, take a look at this for you? And some people say yes, no. Some people string you along. How long did it take to get fuel ventures to back you took a year so this was a year-long campaign and what were they out of the nought to a hundred that you approached would you say can you remember that in terms of where were they on the list yes right at the end where they they were the last one i met there was it was that you were banging on doors oh i was banging on okay i've done i've done that bit yeah yeah yeah i i did fundory i mean i never i'd never in the businesses that i work in now as well i never not fundraise it's part of the game it's part of technology but uh for a whole year we was collecting some angel money along the way kind of thing but i was then started a vc process every single one like i said mostly in face-to-face meetings actually some emails obviously say call it the first of the of the hundred odd i met yeah you never meet them or it's very quick or whatever and then you do loads of other meetings and it was before zoom calls were popular so this was face-to-face coffees whatever which is the best yeah yeah yeah yeah and then uh boom yeah everyone said no and i was like fucking hell this is absolutely horrendous so you asked me if it was no like they were the only one and they were the last one i met that said yes but market of one yeah that's all you need so yeah and the game is you're gonna just have to deal with the reject the rejection which we all do whether it's in all parts of our life there's rejection everywhere different parts of life but you've got to have the resilience no such thing as no it's just not yet precisely not yet wait keep going keep going where a lot of founders would go, sod this, I'm not doing that anymore.

38:36I've had enough, this whole VC world. I'm losing traction on what I'm trying to build here because I'm looking for VCs. Because that can take your eye off the ball as well. Maybe not you, because you built so amazing, but you were still looking for the VC money while trying to build the content cal at the same time. I was. I mean, I would work all the time, 24-7 kind of thing. But fundraising is the CEO and the founder's full-time job is the way I see it for a good period of time in your business. And it never goes away. you know you always want to be dipping in and out of the business obviously but most people don't realize even in nasdaq floated corporate businesses the ceos do not work in the business they work 20 30 in the business what no matter what they say they are in front of wall street investors or whatever it might be or if you're in the startup ecosystem you're in front of vcs you're doing this i remember someone saying that well not someone somebody mentored me said to me again i was 24 you need to understand how corporate finance works inside out so what did i do on the weekend studied it i studied the hell out of god i was like what the hell is corporate finance yeah yeah and uh to me i was like i was a product founder i made a product i was a social media guy that's what my whole story was about and then i was like oh no this dude is actually correct like if i want to build this into what it can be i want i need to raise a lot of money and i had not been doing that the right way for a long time but i've just been going out meeting people where i said yeah yeah i actually need a strategy and a plan and all that stuff so yeah yeah when the vcs come on board fuel how much did they invest and what percentage did they take uh they invested two and a half million in the first round and they took i think it's just over 25 at that point as well then it became quite formulaic okay so they and then we you're 55 you're given 55 roughly away yeah total at that point and then we had a slight management pool so you know i think we had about 10 12 management incentive yeah yeah yeah yeah yeah yeah i i when we sold i had give or take so i think it was like 28 of the business left which is given in the grand scheme of things was pretty good and you end up selling for 110 million dollars wait put it there mate put it there i i'm actually banned about talking about any financial numbers attached to the republic but yeah yeah yeah yeah yeah yeah it's nuts yeah yeah what's a journey it's fucking crazy and you know what another crazy thing about that bit we raised our series a so we raised six million pounds seven eight million dollars whatever it was in march april 2021 so this is through this is through fuel this is through fuel guinness ventures and a couple of angel investors okay and then i sold it to adobe six months later in december boom did you know adobe was hovering around did you know anything what what will you see what's going through your mind i'm building this i'm building this i need to identify because we all do we need to identify someone who's going to have a piece of this or want to buy in a buy to take it to another scale or bite off me was there nothing in your mind i have a deck from my probably my first or second ever content cal deck with target acquirers on it and it had like salesforce various other brands and adobe was on there did i think in my wildest dreams adobe was going to buy content cal no adobe is the best buyer of content it's the biggest marketing technology business in the world it's the biggest creative business in the world it's a phenomenal company and uh did i think did i think it could happen well yeah maybe i mean well it's logical give it a go yeah it's logical right but did i think it would actually happen and the way it did no no it was it was honestly it was amazing it's it's changed my life to be honest yeah yeah no and yeah well yeah yeah there's that bit which is great but also comes with its own challenges right but um yeah you just yeah you know so when you so when the so the vcs come on board for the first two and a half mil then they reinvested again another two and a half they did i think they did um yeah they did like fuel did another two two and a bit maybe yeah guinness ventures did two no they did three yeah and then there was angel investors what at the end again no i just tagged on to that round as well yeah and then and what year was that that was in 2021 2021 2.5 million we did the first vc 2020 yeah uh 2021 march did the fuel ventures guess what we just talked about so that was about six seven million pounds yeah but then we sold in the end of 21 so when they must be they must have that's that's fantastic for everyone yeah everyone involved this is fantastic yeah it was a good it's a good outcome yeah brilliant great outcome so when you when you when you got the last round of money in how did the door open for adobe at the time again crazy um we were we closed that money we were like two months into what we call deploying the money so hiring people marketing spend but we'd already got a machine going at this point this was we had 4 000 customers it wasn't like we were baby business at that stage so we were like right what's going to get us to the next stage in the business so we can do what's called then a series b later down the line and i'd already started talking to investors about the next one but by that point content cal was a a business yeah it was small still in the grand scheme of things but it was a business but growing but growing fast as well yeah and then um we changed domain like five or six times we had content cal dot something content cal dot io then we managed to buy the dot com so we moved over how much you pay for the dot com 25 000 for the guy started um what's it called i don't know like $210 ,000 or something like that.

43:45And I got them down to$25 ,000 in like three days. Chris Voss's Never Split the Difference book gave me the hack for that. Yeah, which I was just like, I can't remember how I did it, but I was just like, it would cost me$2 ,500, whatever,$210 ,000 to rebrand the business. I'll pay you$25 ,000. And he was like, yeah, go on then. So when you were playing around with the.io, because it's annoying, you need a.com. You need a.com. So when you found that.com, how did you find it? And was it someone actually in that game of selling domain names? No, bizarrely, it was it was someone it was it was on the internet you know like who is or you can see who owns domains there was a guy out in silicon valley which basically was the worst place ever because they're going to think big money basically and he was a guy in marketing i can't remember his name he must have just sat on it i have no idea why he bought it he bought it before we existed so it wasn't like a he bought his just no no no no no but we were the we denounced all our fundraisers at that point so he probably thought cha-ching these guys can afford two hundred thousand dollars and i was just like i'm not going to pay that so but it didn't take long to negotiate that down.

44:41It was quite a distraction. How did you contact him? I found his email address. No, I found him on LinkedIn. Found him on LinkedIn? Found him on LinkedIn, pinged him. Pinged him, said, I found him. You must have said, can you remember your words? You don't want to go in with the... No, it was like, oh, you know, I'm the founder of Content Cow with this... I'm really young. UK-based, growing business. Yeah, yeah, exactly, yeah. Then he was like, yeah, 210 ,000 bucks, barely. I was like, I'm not paying that. Did you manage to get him on the phone at all? No, no, it was all done on email. We've still got the email stuff.

45:06So there's no conversation whatsoever? no no no no bam he transferred over 25 yeah yeah i mean bear in mind uh so that was pre-covid i mean give you an example of how much you can do online i never met anyone from adobe when i sold my business to them because it was during covid i got asked to go into one meeting in the shoreditch office to have a uk rep meet me to make sure i was a physical person because other than that i was dealing with the san francisco team in in over over teams or whatever never met anyone it's it's nuts this is unreal story it's crazy this is a proper unicorn how do you go how do you go from adobe approaching you yeah or did they approach well they're sorry that was the question so i i had like four or five old inboxes yeah and the email from an adobe corp dev guy called justin wang who's a legend emailed me to a to an old email i never checked but i just happened to check it on the day that he emailed and i went in and i was like this just look it looked like spam like a fake one okay yeah look really fake yeah and then i went on to linkedin and found justin and he didn't have a picture on his thing i was like this is just not real but obviously i went back to him said yeah yeah cool and then um he took like i don't know like a week to get back and i just assumed it was you know whatever either spam or just not gonna happen and then he got me on this call we had a chat about content cal it was in the context of we invest we partner we did you know we do different things with businesses so we had a chat about content cal and then he asked me to come and do a demo to a lady in the team called um michaela who was a product person at adobe bearman i don't know who these people these are people on the other end of the world basically so i did the demo of content cal they were like we'll come back to you in the next couple of months you know like it but you know there's no there's no action here basically month later or probably three weeks later can we have another conversation and basically what they did and it was super smart they then started getting me to do product demos to different people in in the business but not really giving me the context as to why but of course you know you're founding your business you're going to do that so i probably did like five or six product demos and then just like that took like another let's say four weeks they were just like can we meet you every week and i was like so fix timing the diary and i was like okay but like why and they were like we just like you we just want to talk to you every single week and make sure we've got a slot in the diary it's just so smart because obviously we knew something was therefore piquing their interest but they were so coy about the whole proposition and um sometimes i'd go on those calls and have a chat literally and then i saw a really good rapport with this guy called justin who was on their side and then uh sometimes i'd go on and it would be can you send us this bit of information whatever it might be and that went on for like probably a month and then um i said to them this was approaching summer at that point like guys i'm blocking out time uh you know every week for this now uh we're raising a series b uh we've now sent you at this point quite a lot of stuff and i'd go on calls and again they were so whether it was on purpose or by accident smart but like i'd go on calls to do a new demo to the next stakeholder or whatever and it would just be me and justin on this invite so you'd think you're going on and normally it'd be like one or two people on the other end one time i went on then there was 50 people on the other end of the course something ridiculous and i had covid and i was just like oh my god it's just like honestly i was like sweating yeah uh but um hey it worked but yeah and then it was like guys can you just like you know just tell us what's going on here yeah and then they were like look we're looking at this space strategically you're one of three we want to do a deal we can't do it for like another five or you know it's like eight weeks or something and i was like guys i've got i've got i can't i love to do it i need to crack on yeah so i said look i need uh i need to know if you want to do this in the next i think it was literally getting like a two week ish i say deadline but target i was like otherwise i'm gonna i gotta raise money like i'm gonna do this and to be fair to him two weeks later came back said we're gonna do a deal probably four or five days later came back with a term sheet with with the offer and then probably three days after that we'd sign that then it was three months of due diligence then it was done it was slick it was slick and this is genius it's crazy this is genius it's crazy i want to know the bit when because it's great they all know all the details and you're like god they're on they're on we're on to something i don't know what it looks like did it then you're just like give give give give it and give everything i didn't sign ndas i was just so like some people go i'm just like i'm in it's not worth you want to have a chat exactly yeah yeah yeah but where was the bit when they you said kind of gave not the two-week deadline but you're kind of like guys i need to know because i need to raise yeah when was the bit when they come in and said yes we are really interested in acquiring you did they come in with an offer without you even saying a word no we actually gave them they obviously asked for all our cap table how much we'd raise what valuations and stuff like that we then gave them a series of ranges starting from you know crazy numbers then coming down kind of thing and i was actually very i wanted to do a deal i was like i'd got to the point where i was like if content cow lands at adobe yeah pending terms this is this is the best this is an amazing outcome um and so you know our investors were like go in here and we'll get them down to this and whatever else so we had like a real talk about you know not necessarily the bad side of vc but the toughest conversations i actually had were great news was selling the business how much for yeah real push on squeeze as much value as physically possible and to be fair to them that is their job to make money for their investors adobe don't want to necessarily get the they're not what i'd call a value driver in that they don't want to pay the lowest price they want to get a great deal done and that's what i love about america and be fair and actually i find actually in america that's the general thesis of doing deals whereas here we in europe we squeeze quite a lot they're like look we don't need to pay the lowest we ain't going to pay what you've been told by your investors over there somewhere here we can we can probably get comfortable and then um yeah honestly mate i bet inside you think it i was comfortable i was comfortable yeah yeah i was very comfortable there yeah yeah uh did you have your calculator again right the us dollars to the pound yeah minus 67 given away that's left me with that yeah yeah 28 then you start going into the terrible things what would i do with that what did you go for what i think i can't think about it's not going to happen yeah it's awful but great at the same time yeah it's one of the worst things genuinely uh do you remember the number they initially your vcs wanted to go in oh yeah it was it was it was much bigger than what we when we went for it was i can't remember exactly it isn't like you know multiples on what you quoted basically multiples we're talking like 500 mil or something like that but not far off okay and then you come and did they come in a lot lower than the the deal you actually got no they actually i can't go into the exact no they came in not far off where we landed actually and they actually put together what i'd call a really good and fair price at the time and we actually went back and said our investors wanted up here we're being told they want up there and then i just said and And one of my mentors, again, who's on our board, Colin Smith, who's done a lot of M &A, was like, oh, at the end of the day, everybody's here to do a deal now.

51:45Go in what you think they're going to do. Just say something that you think they're going to do, and let's see where we get it done. And that's what we did. We went back and said, look, we actually need to be here. And they were like, yep, based on these things as well, done. So money wasn't necessarily their biggest problem, pain point, whatever. They wanted, okay. Product team. They were like, we're going to do this. We want to do it with you. Let's make it happen. Yeah. It's unreal. It's crazy. Isn't it? Yeah, yeah. And then I spent three years at Adobe. So I did it in my earn-out was three years.

52:11And for a lot of founders, that's like the worst nightmare. I had a phenomenal experience. I mean, in some parts, I didn't enjoy. So I'm not - Did you go to America, did you? I was backwards and forwards between London and America. San Fran. Half and half, yeah. Where are you? San Francisco? San Francisco. Yeah, yeah. I mean, they have offices everywhere, but it was between Silicon Valley. So they have like four or five offices in San Francisco. I mean, Adobe's a mega business. It's a big business. Do you know how big, roughly? It's 30 ,000 people, 20 plus billion in revenue. when we did the deal the market cap was three or four hundred billion it's the biggest marketing business in the world yeah something last day is one of the biggest one of the biggest businesses in the world um and yes i spent three years in their product team on adobe express which was their version of canva their brick new kind of push and then in various other parts of the organization and did i love all of it no i didn't love the corporate element of it i didn't love the style of meetings that we had often and they would actually laugh that i'd say this but like the amount of bullshit conversations and i became known as one of the guys and our team were like guys what you're debating is actual bullshit yeah and they actually took it quite well and i could use my well that and my founder like guys some of the stuff was literally bullshit quick question when was the last time a display ad changed your mind now think about the last time a friend told you about something they loved different feeling right that's how podcast advertising works.

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54:01yeah but i loved the um the concept of the way they look at businesses versus how we do is they go right this is the size of a market it's however many billion to build a category defining and leading company in this market it's going to cost 200 million okay how long is it going to take it's probably going to take three years to get off the ground two years to get into maturity and another two then to go and dominate okay all right what's the best people we need well we need a leader of this this this and this and we don't want average people i want the best people to build this best people to do that okay it's going to cost us to get a billion dollar outcome it's going to cost us 250 million okay here's 250 million it's just like that's how they think about things they're not like well we'll drip free 20 million in and we'll sort of see what happens and then maybe we'll do the next one it's like no here's the money here's the best people in the world to go and do it there's not fanny around let's not fuck about and go and get it done and and that that is something i've taken into jack into all my other businesses that i do now like i don't want to do what i did with content cal which was a brilliant journey to learn but very piecemeal yeah i'm like size market everything i've just said best people in the best place here's how much money we're going to need to go through this is a multi-billion dollar opportunity give us the cash let's get on with it we know what we're doing on that three-year deal earn out what percentage did they pay you up front to say there you go congratulations and on the earn out did you have to hit certain targets i had 80 up front 20 held back and i had no targets other than being employed it was beautiful amazing deal yeah yeah yeah it was an amazing did you negotiate that or did they just say this is what we're thinking i was at that i think they were like at 70 30 and you know so there's a bit of negotiation but yeah their main thing was honestly they wanted the product they wanted you yeah basically and the people in the team and everything else they wanted an embedded product so that actually that could continue forever more you know they wanted me to be there to make sure everything got embedded properly and all the rest of it and to be fair i almost stayed i mean i would never have stayed forever but i was quite close to taking a role in their venture capital team which would have been fun exciting yeah yeah and then i was quite close to sticking in a similar role that i was in uh but different but it was just for me i'm 35 i've just i've gone through this journey i've got to go again like i can't i can't i've got the energy yeah it's in my blood yeah yeah yeah i'm not i'm not a corporate dude yeah yeah yeah when you when they said what you want to come we want you to do a three-year earn out did you have to fly back and forward like 10 times a year how did it work probably like five times a year yeah and like a week or two at a time maybe a month sometimes i don't know i don't know maybe not a month maybe like two or three weeks they were quite flexible but again it was post-covid so very remote working and you know there's great we've all been through that there's great elements that you can wake up and have your coffee and then you do a few calls and have lunch actually quite a lot of my calls were in the evening because we were dealing with san francisco but the biggest challenge with it was and it was post-covid where many people started like coming out, going back to offices, social engagement with teams, joining new businesses, we were pretty much still 100 % remote.

56:53And I've actually looked back and realised that was quite challenging. And also because we were working. You lose culture. You lose the vibe. The two things you've just said are actually the two biggest things you lose and then the social connection. You lose culture, vibe, and you don't meet people. How do younger people learn? I don't know. You've got to be in with people to go, oh, he's got 10 years of me, I want to learn off you. Just even the little bits and pieces here and there, Like it's... It's too mechanical. Yeah. Do you know, I talk about this like for hours. I'm a big fan of actually remote working when you're in certain stages of your life and the rest of your life.

57:25We say when you're young, but actually at any age, like you said, if you're not around human beings, learning by osmosis and connection, you're not really leading what I would call a fulfilled life. We all have to work. So why not have that part being like intrinsically linked to your human life? That's a big thing I think about when we're running Jack and stuff like that, but it's important. human being and human connection and discovery and meeting and broadening your horizons is so important um and so yeah we didn't have that and that's the part of the reason again i was like now i need to be in an environment where i'm i'm back out meeting people and doing stuff like this or whatever where were you when you signed the deal when you knew the money hit your bank i was on a zoom call um in december 2021 to the team in my two-bedroom flat in wandsworth and uh i literally was obviously refreshing the old flick thing every few seconds.

58:17And they literally was on a call. I can't remember what we were talking about. Looked down and I was like, there she is. Finished my call. Put my lap top down. Re-opened that. And it was just like this for about 20 minutes. I was like, hmm. My God. I was just like, freaking wowzer. But do you know what's so weird about it? It's it. I love this. It's a number on a screen. I know, it's weird, isn't it? It's so weird. It doesn't really, I always think that someone should bring it in cash. Yeah, or something should happen. Something should happen. yeah doves fly out yeah the thing is when you sell a company we were the same we were like yeah we we've done it we've done all right yeah well life carries on oh yeah go to the pub or something yeah bottle of champagne i don't really like champagne but did bottle of champagne yeah oh is that it yeah i know i think i had a nando's or something yeah but you know what is a reality and this is where i'll tell you how my my life transformed outside of the financial side so you and you probably have been through some of the things when that happens to you nothing like you say nothing changes but everything changes because actually what happens is over the course of a year this is what i found because our deal was announced on bloomberg and blah blah and then i decided to put myself out on social media as an investor and all this other stuff everyone around you treats you slightly differently for a period whether you like it or not and that's weird you know suddenly because you've become wealthy yeah um everyone assumes you've now got a great life everything's perfect cut you could never be you could never be down ever again as you've got money um if you've made some cash um every person on earth who manages wealth and wants to sell you something basically anyone who could sell you anything comes at you in one big fell swoop and um i think that your mentality or mine certainly did anyway changes massively to okay well now what the fuck am i working for yeah because it isn't for money yeah and i actually had a huge huge identity crisis and actually went into a period of depression after i sold my business and and it sounds so weird to say that because like money whatever yeah but i really realized that my entire being was building a business content cow the team that you know my entire life was embedded into that thing rightly or wrongly and that's probably partly why it was successful but i then spent two three years outside of my adobe stuff and outside of angel investing and all the rest of it actually in a state of actually just large confusion to be honest thinking now now what the hell do I do and what do I do when this is all over in three years and three years is a long time to be in what you call kind of golden handcuffs in a way so I had a lot of time to think and I realised that actually when I met Jack and did various other business things I want to spend my time now on things that basically can improve humanity and you think a lot of I think a lot of exited entrepreneurs or Jeff Bezos and all that they're all investing in longevity and health and stuff but actually if you can help people through products and services and scale technology and what the rest of it and use your skills that you've still got through the means of business i think that's the most meaningful thing you can go and do so that's what i'm doing now with jack but actually like the highs were the highs again but the lows were yeah actually afterwards really low thank you honestly not a lot of people would say that yeah not a lot of people say that because a lot of people listening but mate you've got all that money in your bank you're not happy happiness comes within and you're happy building a business now you go your baby's been taken away it's like well what can i do with my life now yeah there's only so much gym you can go to or golf you go to the holidays you can go on to or houses you can buy all the cars you buy what you buy after that what else is there well that's it i'll tell you i'll give me a bit more honesty and i'll tell you the story i bought a lamborghini yeah i bought what color it was black hurricane evo and it was it was awesome yeah but it was it was nothingness how long did it that how long did that vibe take till it wore off and go well i've got that outside my drive for so i'll tell you in the first so i sold my business in december 21 i bought i bought nothing but a house for a whole year i purposely said to myself i'm not going to go and splurge and i was quite busy still with the integration and then in the second year as a lot of the upfront work integrating content came into the w's done i had a lot more free time and and that's when some other stuff went around in my life and i was like right and then we had a another sort of release of money and stuff like that through some legal stuff that was happening in the background which was you know it was good it was all it was all clean kind of thing and then um and then i was like then i hit that's when i hit what i call kind of crisis point i was like i really didn't know what i was going to do i was really feeling weird and then i was then i realized i went into a phase of depression i was like i didn't even know what this was and then um and then i bought the lambo and then i bought i took my mates on a massive holiday tomorrow which was amazing but like it was wild and then uh how many leds it was actually only three of us i don't mind telling this girl i spent sort of like 60 grand in a weekend on a yacht i mean it was fucking amazing i'll be honest yes man obviously it was why not that's but that's experiences but it took me a year to get to a lot of my mates connected me like why aren't we doing this wild one of them in particular is like why are you still here like why haven't you just fucked off and traveled around the world so yeah so we had some fun and then that's when i got into six months of really like okay something's not right here the lambo didn't you know it's a thing i had it for six months yeah but yeah it was such a weird dynamic and then like you just said happiness comes from within to be happy you have to know who you are what your mission your purpose your values your vision and that doesn't mean writing that all down and like being totally clear on it but you really have to be comfortable with yourself so i got really into mindfulness meditation journaling which really helped me but now i'm very embedded in that concept of like if you know who you are and you feel comfortable and you know what you enjoy and how your time is life comes with its ups and downs and that was the biggest like proper bump i'd have a real like who am I and what am I here for?

1:03:47Then you can build a great life. Then you can have a really fulfilled life, no matter what your financial situation is. If you've got that stuff set, like you said, and you feel good from within, that's how you can actually give your best out, in my opinion. Or find a really, really good missus. Or that, yeah. I've been my wife 22 years now. I wouldn't be who I am today without that support. Totally. Fully supportive. Oh, no, 100%. You're not like, where are you? What are you doing? Fully supportive. you know that's not a better feeling no no i i found jasmine who i'm with now my sort of kindred spirit uh you know after all this stuff and i don't i've been in relationships but in different ways and she's amazing like yeah like you say like finding someone who you really really enjoy being lovely laugh and love it's amazing yeah it's incredible what's the one that's the most expensive what's the most expensive thing you've ever bought um outside of houses yeah uh i'll tell you some cool shit i fucking actually so stephen lane mentor from earlier in the story owns a business called prop store which is a film collectibles business which is movie memorabilia entertainment memorabilia but it's the stuff used in the films so i own robert downey jr's iron man head i own christian bale's how much is that iron man head 120k or something i own uh i own christian bale's batman dark knight helmet do you and it's freaking and that's one of my favorite films that's the best yeah uh what'd you pound that that was like that was 120 000 i own loads of props basically which in my office and there's just cool stuff right yeah i own a watch you know i bought a cool watch whatever i think the film prop is probably the most expensive thing i think i'm much more of an experienced person i have a really nice house in in surrey which was definitely my most expensive thing but and then outside of the lambo so i bought some stuff the way i'm talking about it yeah yeah what was that feeling like knowing that you've got all that money in the bank going from a two-bed flat in wandsworth probably going to the ship every sunday night and getting on the spot yeah i lived just i was in chelsea i moved down and moved down to bournemouth 20 years ago but yeah what's that feeling like going from a two-bed flat grafting your nuts off for those years getting the money in the bank and then going i'm gonna go house shopping in sorry well i actually went house shopping in wandsworth first so i actually ended up i actually ended up buying a house i loved wandsworth so much i actually shouldn't have bought this house but i um i went house shopping in wandsworth first and it was like it was surreal yeah and so i bought i bought a five bedroom townhouse in wandsworth and like i was living in a normal two bedroom flat as you might have in london whatever and when i moved in there we called it wandsworth house like soho house and then people were like is there a soho house coming to one wandsworth like that because i had so many parties yeah honestly i did i just moved in like all my mates around they were like fuck that's like and we had it and we did we had at large every weekend yeah many weekdays as well um and it was so cool but yeah it was surreal but again you know i was actually in a lot of the time i was living there i was on my own you know so actually having the parties and you're not sharing it with yeah other my mates kind of thing but yeah it was good though i mean don't get me wrong and then the house i bought in surrey actually so the ones with house thing was kind of like a part of the blip in that journey but it was a lot of fun but the farnham house i have which is like in the countryside big green nice views all that kind of stuff that has become like real tranquil to me and home is actually something i've it sounds weird to say this but i've never felt like home home yeah my family home is um we moved around quite a lot when i was younger and so i never felt like at home home anywhere actually up until really quite recently so i always felt quite uh transient yeah where i live kind of thing and also most people know when you live in london's temporary like you're there for like 10 years but you're not going to be there forever right yeah yeah what was the how much turnover were were doing in the business the moment you sold it for 110 million dollars we were doing in dollars probably seven ish million okay by the time we sold it so not not huge yeah not not small but not huge it was growing yeah we grew really quickly during the pandemic so what multiple did you get in the end i wouldn't be able to do the numbers on that because it wasn't valued on the multiple it wasn't they wanted the asset yeah all the customers were turned off yeah were they Yeah.

1:07:55Because the amount of$7 million to Adobe is nothing. Oh, wow. Nothing, nothing, nothing. Why would they turn the customers off? Because we were not profitable, right? We were burning money. We were still in growth mode as a business. So you're turning over$7 million, but there was no profit whatsoever? Well, if you stripped out all the costs, so the sales costs and the marketing costs, but you have to put it into context of the Silicon Valley thing I said to you. Adobe look at markets and go, it's going to cost us a billion dollars over 10 years to do this. $7 million. What, to make it themselves?

1:08:23themselves to build what you've done whatever they're doing no not what we've done but like to dominate a market call it like small business creativity that's how they look at it for us to dominate small business creativity of which we need to build this feature this feature this feature we're going to buy content count stick that one in there we'll buy that one stick it in there you know over say a 10 year period that's what they think about they're like we need to put this much money into it 7 million 4 000 customers of which most are adobe customers anyway yeah there's nothing nothing okay in fact it's almost like it's not an annoyance but it's like we just turn that off because we don't need that they're all paying us anyway yeah in some other product we've got because everyone has a domain account in business they have to really so that's what it's called it's called an accu accu hire acquisition hire that's how they think about it it's like a yeah it's crazy it's it's hard to get your head right it's bonkers isn't it but to the point i was saying about software businesses what we don't realize is that in the uk in particular we are quite venture capital is quite often funding the research and development costs of Silicon Valley.

1:09:20So we will build products that will get to a certain size and scale. And they'll snap them up. Ching will value. Yeah, yeah, exactly. Yeah. So the actual model is you're building a business, but you're building it to proof points for large companies to acquire you. What are you doing today? Today, I'm running Jack. Yes. On the hoodie. And that's just, yep, justaskaquestion.org. Anyone listening, it's an amazing website. Thank you. Amazing brand, amazing everything. Thank you, mate. Yeah. I was an early investor in that. Oh, you're joking? yeah no i was an invalid thank you for supporting the business i didn't know that bloody hell did you get my email or not no i sent out a shareholder update but i've still got some missing emails so maybe i've missed you i'm not i need to well we'll sort that we'll sort that anyway when this was a couple of years ago someone told me about it danny gray come in who's the founder yeah and told me about jack and i was like this is how do i invest in this is this is going to be a unicorn oh cool i was instant yeah really you got it i saw it straight away i was like wow danny's amazing um um so i mean i came to jack actually so i invested in 60 companies so if you so so you've invested in 60 companies what's your company called to invest in those companies or have you got me so it's just you you're going i'm gonna personal i'll have a piece of that a piece of that piece of that and this build these yeah so does that excite you it did now it doesn't yeah it really did i used to love it i used to meet founders etc and i never thought i want to become a professional investor it was a it was a it was partly a hobby but also you know it's part of my investment portfolio for my life rather than keeping it in the banks hold on let's invest let's get it in businesses yeah yeah exactly so um i did 60 over two and a half years i'd actually come to august 24 so i had six months left of my earn out and i was like well what do i want to do firstly and secondly i don't really want to invest anymore and then i met jack through a guy called john reynolds and he brought me in i've good led john you know john yeah yeah he's a legend down here uh did he no of course he does yeah yeah no he's a ledge so he brought me into jack to come and well he showed me the platform talked about it and then i hadn't since realized that they were on the hunt for a tech person but i didn't know this at the time and because of the mental health stuff i'd gone through i was like do you know what if i had this when i was going through what i went through and then extrapolate that out to every person on the planet yeah um like you said this is a unicorn 100 and that is the way i think about it and then i met danny um i met dan kirk a bunch of other people in the jack team both two great guys yeah legends yeah yeah and for me i was like okay so if i'm looking for i'm gonna go back to the silicon valley thing biggest possible global market which is basically in jack's world everyone potentially everyone's going to go through stuff in their life um have they built enough traction they've got this many videos on platform like you say jack.org they had traction with a big client um in bupa um he's a great partner of us um you know they had all these proof points basically great team all the rest of it but what they were doing was they were doing this they were like maybe we could do that bit next maybe we should do that bit next you know again because they're really yeah and i came in and so I actually invested uh 200k and then I was like guys I just for what it's worth and you've said to me you know you want someone in tech I have done all of the things that you need to do you are trying to do and I'm good see what you're doing and I can just give you the blueprint here so I spent six months advising the business from August last year to December and then um I was basically asked throughout that period saying would you consider coming and joining us full time as the CEO originally potentially not but actually it just came really clear that actually that was the that was the role that was probably needed and so um had a chat with danny obviously and various others and said look i would i would i'd be up for it you know let's think it through and then i was like do you know what like i said if i could use my skills and my time to help people go of which something is personal to me i've been through a mental health thing yeah if i can create something which is a huge platform globally and a unicorn business and i actually believe business is the best vehicle as forces for good because it's commercially incentivized you can do things quickly at scale charities are brilliant but they have their own challenges and uh so yeah i joined in uh joined full-time uh officially in april so i was advising for a bit longer and i'm in the in the full-time seat yeah driving the business fantastic and we you know we've just gone through funding rounds we're building up you know we've doubled the size of the team we've we'll do like triple the amount of revenue we did last year it's grown really big and my view is we've got to get it to a billion lives positively impacted impacts yeah and then i want to get it to over a billion valuation and i would like to then have it live in a either a much bigger businesses ecosystem and and kind of grow in that world or i'll take it all the way through to whether it's like just just scale or ipo or whatever because i really believe that when you're going through something but that might be depression it might be adhd it might be might just be sleep and stuff like that much lighter things i think this has got all your answers this has got a video format from celebrities yeah people that look like you feel like you and your demographic doctors and we deliver it in a way which despite the subject matter sometimes is actually quite tough like to take like a subject awful thing like suicide or something lighter like a sleep and you know meditation whatever there's nothing better than watching video content and as you do with this in a slightly well very informative but actually slightly entertaining way and a cooler format and a cooler format yeah yeah yeah so i really believe in it and it's got you know all the legs to go all the way i believe so and we invested six figures into it as well thank you for investment Yeah.

1:14:29And I saw it, I think we invested maybe 18 months ago, early. Yeah. And I was like, oh, man, this is something. I said to my wife, trust me. Yeah. Trust me. And then we had the initial conversation and we're like, wow, we're in. Yeah. Let me roll back a bit. Uh-huh. When will it become a billion dollar business? What, Jack? Yeah. That's a good question. So I know when to sell my shares. You'll hear from me. You'll hear from me. Yeah. Yeah. Do you think it genuinely can get to that? I wouldn't be there otherwise. Yeah. Okay. I'll tell you how. Are we talking like, go on. Well, I'll tell you how and why.

1:15:03Yeah. So run the numbers. Again, use the Silicon Valley, you know, modeling. There's 7 billion people on the planet now. I don't know what the number is, right? Give or take. 7.8 or something. 7.8. 8 billion. Yeah. 30 % of people in their life actually go through a mental health actual challenge. Not something like a sleep or diet and how to optimize and live a great life. They actually go through a fundamental challenge. And if it's 30%, it actually means really it's probably more like 50, 60, because who talks about it? It's hardly anyone, right? So numerically, Jack can reach that many people and positively impact that many people.

1:15:37Now, that might mean you watch one video and never come back. That might mean you watch 20 videos and go and get a diagnostic for something. That might mean you actually just really enjoy the platform and learning and hearing because you're into understanding your nervous system or whatever it might be. So we're not just mental health, we're mental wellness as well. I want people to be able to learn and fix issues that they have, go on that path. And I want people to also optimize their life and their mind and their body together. Because that's how you, again, going back to what we said, whether it's fulfillment, whatever.

1:16:05If you can have the mathematical backing conceptually that you can actually have an impact on that many people, it becomes a game. Not a game, but it becomes a game. So I need to spend, again, back to the investment thing. Let's call it, let's say it's, I don't know, 100 million marketing. that has to go in to get enough people to this platform so it's all traffic traffic driving from there we have different routes of monetizing working with brands working with partners working in b2b if we drive a you know a hundred million people or 200 million people or half a billion people into the platform i know how many people are going to watch videos sign up might yeah participate in uh monetized activity whatever that is we know brands will come to us and pay for that audience because they want to be able to promote things like whoop and stuff that really can add values your life like it becomes formulaic to be able to unfold this business and then you go okay so to do that we're gonna have to do the financial modeling all the numbers stuff put that together the vision speaks for itself i want to positively impact a billion lives and a billion people's mental health and wellness that's a good mission and i think that as the world's going on from here with ai and everything else you know over a hundred year forecast people people are not going to need to work as much as they do and different dynamics of life are going to change and the finance side of things is going to get harder you know there's all these complexities that are unfolding in front of our very eyes and therefore meant and the news and war and mental health and and that kind of stuff is just going to continue to compound whether it's a problem whether it's just a thing put all that together then i just need the best people in the right places to execute on their thing yes if you're a salesperson and you're the best in the world come and join us if you're the world's best marketer come and join us if you're whatever bring the best people in create the culture where you can get shit done yeah you can make mistakes but and that's okay we're all to this yeah it's kind of formulaic yeah easier said than done so you've got to be in the trenches as well but there are very few businesses that have that set of ingredients and jack has it and i wouldn't be there otherwise and you wouldn't invest it otherwise absolutely and nor would everyone else absolutely so that's the goal well they've certainly got the best man for that job yeah i hope so no they have they have no no no i'm here now i'm here with you today and yeah you've been through it you know it you get it you got the t-shirt you speak our language this is what we're going to do we've got a formula it works yeah the business model is phenomenal the people are phenomenal the website's amazing danny gray is the founder's amazing like it's got everything going on it's got the best chance it's got the best chance and now it just needs to go yeah Yeah, yeah.

1:18:35It'd be turbocharged, bang. We call it the rocket ship. We need a SpaceX rocket launcher. Danny's great. Danny's analogy is like build a lifeboat, like test something out, which we still do. Yeah. But I'm now literally saying this yesterday. I was like, right, lifeboat now needs to be SpaceX rocket launcher. I need firepower to get this thing to as many people as possible. So that's where we're at at the moment. Wonderful. Yeah, it's fun. Alex, are you happy? I am very happy, actually. It's a really good and interesting and very deep question. Have I not, have I always been happy or have I gone through periods of not being happy big time?

1:19:10I have had, uh, I've had two years of therapy every week. I have gone on, what do you call it? A spiritual awakening or a journey. Uh, I have gone from what I thought was making me happy to not things like whether it was work or other things. Um, and I actually, I've done the, done the work to know what makes me happy and also know what doesn't. and also know that actually if i'm not happy it's not that i can fix it but i'm i can i can actually just be you know down for a day and it's not going to be the worst thing ever so that's how i think about that happiness is to me like a part of life right like but it doesn't have to be a it's not a constant thing i used to actually really think like the whole goal of life is to like be happy all the time and it's not you have to go through the ups and downs of life but we only live once i have done my phone quotes memento mori which means you you must die if you side of that one, right?

1:20:03Yeah. You've got one life. You've got one life, right? We have one life to do as much as we can, crammed in as much as we can. Yeah. Yeah. Are you happy? I'm really happy. Yeah? Yeah. What's your take on that, then? I just got a nice, lovely little family. Everything's calm. I go home and it's calm. My wife is calm. My boy is calm. I've got good friends around me. I'm not into watches. I'm not into fast cars. I'm not into any of that stuff. I like long lunches with my mates. I like a glass of red wine. I like going on holidays. I enjoy the finer things in life, like travel and hotels and villages, those things.

1:20:45I'm not into buying cars. That's just not my thing. I've got a good bunch of mates. And my feet are firmly on the ground. And even like my mates from this age, we're still tight. Yeah. There's a great bunch of us. How important are your mates are to you? Really? Yeah. Super important. But you know what? As you get older, you realise the difference. my analogy of it is you know who your true friends are but you also must understand who your acquaintances are definitely there's a lot of people who like to wrap up the acquaintances and friends just as friends yeah so no like trust yeah yeah no okay like trust you're a true friend no like don't really trust you're an acquaintance yeah that's how i work it out and it's important yeah it's important that you think about this stuff because people just think oh we must just have friends or you complain about friends and you know and the main thing the happiness for me is like without a shadow of a doubt i train every day do you yeah i train and if i want to do some sort of exercise i train and i have a sauna and i feel good then i'm ready for the day you know you can go is that because you like it and it's just a natural you have you looked into the science of it i've done it's part of my life being a sportsman and yeah it's just part of your life yeah yeah but the sauna thing yeah game changer really 100 i've just bought an infrared sauna 100 % sauna thing you just do 10 minutes really yeah you can walk in when you come out walk into a into a nice gym at nine o 'clock in the morning you've got these things in your mind and these small things could be made big things you go and have a sesh you push yourself hard you lift weights then you go and have a sauna yeah and a nice shower and you walk out they go oh yeah for the day yeah it's so important do you know what's so interesting about that is so i've exercised on and off throughout my life but i've never understood the link between the physical exertion exercise or sauna or whatever it is and then whether it's the endorphin release or the everything uh parastrophimatic yeah everything i didn't i didn't know anything i don't know do you get taught that what was you an athlete what was your background rugby right did you get taught that stuff no right in the 90s uh it was going to drink 10 points have shots and but you were doing it so you got the benefit of all this stuff without necessarily knowing the mechanics behind it yeah i think that's fascinating because now i still don't thing that enough people know those things but actually there's a there's chemical reactions constantly going on in your mind that are creating positivity because you sound like a very positive person yeah good energy yeah nice energy i love being around good people good energy yeah and the thing what people miss out here is no one was ever taught business no one's ever taught entrepreneurship no one was ever taught how to be a dad no one's ever taught how to be a husband no one's ever taught taught what to eat and what not to eat true my god i can look at people and And I know if they're in a clean diet or not a clean diet.

1:23:19I'm not saying you have to eat 100 % clean or weak. But if you're 80, 20 or 90, 10, just choosing the right choices rather than going for the quick crisps or the quick sandwich or the quick diet coke and the quick... This over time adds up. And when you're getting in better shape in your life, it makes your mind feel amazing. You're better to be around. You're nicer. You're kind. There's a knock-on effect of what you consume in your brain. Watching all this flicking... Become a creator rather than a consumer. but you've got to be careful what you consume and be aware your subconscious on your little shoulder don't stop flicking stop flicking what's the point of flicking get rid of that start creating or what are you eating as you're eating it the rest you know the next day you're going to go oh dude I fell in that shit today what's the point and if you can just get that dial on and don't you don't have to go on a diet but just understand nutrition understand what you're doing and understand the addictions of flicking and looking and bumping from each different social media platform etc you know so I wish that everything you've just said was taught to us properly from as young as physically possible.

1:24:21I agree. Because the stuff you learn about in school, I always take the piss out of the concept of photosynthesis. Oh, mate. Pythagoras theory. Latin. Burner. Latin. What's good? That should be, it should be the other way around. Like you learn the stuff you've just talked about at school. And if you want to go down to the more these, what I would call highly niche subjects, go and do those. That's cool. But why don't they teach you like, what you've just said, how to be a dad, how to eat well, what exercise does for you etc like how is that not how to be well mannered how to look someone in the eye and shake their hands and a deal's a deal you know all these wonderful gifts pay your mortgage pay your bill that could be an online course there's so much people have these conversations no one's really done it I've been thinking about it three or four years if we nailed what we've done with our online events replicated that for life skills for 16 year olds up to 30 year olds these days who haven't got a clue like i reckon in the next probably 20 to 50 years the education system will collapse based on i think i think earlier do i think earlier really i'm i'm now i'm going in my kids going to school you don't need to learn latin yeah you don't need to learn publicist yeah you know you don't need to learn algebra yeah and like a teacher come up to me the day was like don't you mind come do it giving a talk i was like yeah it's cool no problem yeah and also um the kids are going to be there they're writing out their cvs and they're gonna but i said cvs are gone nobody uses nobody uses your cvs oh you you cvs was very year 2000 80s 90s 2000 so you know it goes to a lovely school but i'm thinking man the schools that are picking up and going these kids need to learn ai they have to learn ai because if you don't learn ai you're going to be left behind i was having i was having this conversation with someone at the weekend literally i was my two cousins who are quite young in like 10 7 or whatever i was like are they teaching you this stuff in school no no ai but the teachers don't know how to use it they don't know what it's for my boy my boy the other day he went to I said test your algebra teacher yeah he's doing algebra and my boy was clued up little kids he left it sharp yeah gets it and he's like sir what's the point of algebra me doing this algebra I'm not going to use it in later life and the teacher went you will use algebra every day of your life boy and I was like I'm back and told me I was like mate this is bonkers oh my god this is bonkers but the thing is it actually is bonkers it is bonkers no one's doing anything about it absolutely which is crazy absolutely maybe we can have a chat about doing something yeah we should no I'd love to yeah yeah I mean, it is crazy.

1:26:38It's crazy. Alex, I've loved this, mate. You too, mate. I've really enjoyed this conversation with you. Thank you for having me on. I really appreciate it. Like I said, I was listening and it's so surreal because a friend of mine, I was saying, sent me the one with the trading chap you had, which I loved listening to. And I was like, gosh. And then literally, I think you commented on a post or something and I was like, I'm here. I'm here. Amazing. So cool. Yeah. Thank you. You're a huge success. And what I love about you, you're real. Yeah. There's no bullshit. You're real. This is where I've been.

1:27:02This is what I've done. I've hit jackpot great I've had depression I've felt like this now I'm in a wonderful place in my life with a beautiful missus and a nice house in Surrey and I've got purpose again of being the CEO of driving this business to become a billion dollar business please tell me when it's going to become a billion dollar business I'll tell you when we're off cab I'll tell you when we're off cab you're a gentleman legend good marriage nice one mate cheers pal take care take care hi guys I really hope you enjoyed that as much as I did can you do us a favour and leave us a review as it massively helps us grow the show cheers guys

1:28:02We'll see you next time. podcasts, book host reads, or run your own ads and track every conversion in real time. Same skills you already have, brand new results. Acast, acast.com slash advertise.