Our exit collapsed at the last moment | Tom Adeyoola, investor, advisor, ex-Founder of Metail

Strategy & Tragedy: CEO Stories with Steph Melodia is the best business podcast for curious entrepreneurs. Hosted by Top 20 Female Founder, Stephanie Melodia, Strategy & Tragedy features candid interviews with entrepreneurs who have scaled - and failed - their businesses - sharing their lessons in entrepreneurship along the way. From Nick Telson-Sillett who achieved financial freedom after selling DesignMyNight (on The Wildest Exit Day in History™) to Emmie Faust, the founder of Female Founders Rise, who opened up about her breakdown on the road to discovering her mission in supporting female founders.

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In this episode, Stephanie Melodia interviews Tom Adeyoola, the exited founder of Metail, the leading virtual try-on platform, now advisor, investor and Co-Founder of Extend Ventures and Capital Angel Network.

SM: Tom Adeyoola, welcome!

TA: Thank you for having me.

SM: First question what is it that makes half Norwegian half Nigerian men so successful?

TA: I don't know the weird thing is as far as I know there's two of us and we both went to the same university at the same time – one pretended to be an IT on TV and the other one is sitting right here so that was Richard Ayoade from The IT Crowd and we were in the same year at Cambridge he was another college in a comedy duo with a guy who I went to University with in my college who is now also super famous as in John Oliver and who has his own program on US TV.

SM: Amazing that is hilarious I love that fun fact it just really stood out to when I read that you are half Nigerian half Norwegian.

TA: The flags are next to each other as well when you go through the list.

SM: Ah that's helpful! With you and Richard Ayoade is it the same mum/dad?

TA: Yes but we've actually never met each other directly except my wife has met him and had a conversation about a project in the past, but I've never met Richard directly so that time will come. He also made a film called the double which I thought was quite funny it's about somebody meeting their doppelganger.

SM: Hilarious - I feel like I could very easily do a whole podcast about this! But we will move on… Obviously you’ve had such a great impact you've had such an amazing career I'm almost like I don't even know where to start but we will start off with Metail - I feel like has had more of the headlines in your track record so far. So, you founded Metail which was a virtual try-on product which was acquired back in 2019 for 12 million by your lead investor which we’ll get into.

TA: Yes so I founded the company in 2008 you know probably the worst time imaginable. I had been working for a company (five different startups) before starting it out and in my last company I was running gaming product development for a company called inspired - they were in the process of being bought by Icelandic banks in 2007 my boss's were going to become wealthy I was going to make some options it felt like a good time to go off and start something a few of had committed to investing in the business but this was Icelandic bank so as We Know in 2007 the world Collapsed from a credit and Crisis perspective so over the course of the next year that companies share price collapsed by 99% so that opportunity for investment is my company didn't come but I think I've got to the point where with Metail being able to virtually try on clothes and see how they fit and trying to solve that online clothing fit problem - it felt as big enough idea with a big enough way of trying to solve it in terms of using computer vision that I felt that I was going to commit and jump in feet first to start it anyway in 2008.

SM: Before we go further, so just hang fire there for a second.  I'm curious just on a really practical level. You had that funding opportunity fall through on both the options that you had in the company because the share price nosedived. So what did you do instead then?

TA: Well, so I took this sort of rather risky, option just to go jump anyway. So I quit my job at the end of 2007… started on the sort of business plan day one of 2008. The only commitment was that I would continue consulting for my old business for a couple of days a week.

So it was ostensibly a rash decision. Really. I didn't really have any visible sources of funding but I felt that the idea was interesting and the time was potentially now, weirdly, my boss from inspired where I was at, he had worked for a company called boo.com back in 1998, 1999, which had tried every idea in fashion technology back then, and had spent 150 million in like 12 months and gone from boom to bust.

I felt that there was something really interesting about computer vision and some interesting research technology I'd seen up in Cambridge that meant that it was now an interesting time to do something. And I think I just, you know, just thought some sort of funding might come from somewhere!

The naive optimism! I ended up meeting different people going, reaching out to lots of different types. And I had one meeting with an exec at MTV where after that meeting, he and a colleague sort of made an approach to, to invest in the company. Um, yeah, the company, which was in a PowerPoint presentation at the time.

The terms were horrible, but they were sort of proposing to put a hundred grand in and off the back of that, I felt, okay, I think I have something which is worth carrying on for, and this was probably about three or four months into my journey of figuring out how to not spend all my money and, and end up on the streets.

I think off the back of that, I then made the decision to like, get a bank loan for 10 K and at that time, if you were getting a bank loan, you could only really do it to buy something. You can't do it to invest in something. So you had to pretend that you're trying to buy a car and that's why you need the 10k, which is really bizarre in my head.

So I did that. I then ended up getting 10k from an aunt, 10k from an old school friend, 10k from a university friend, 10k from an old boss, and 10k from a random guy I met at the top of the Gherkin. So that was like my first bit of capital.

SM: We'll just leave that last one there, that sounds like the most interesting investor.

TA: And that guy, then three or four years later came to work for me and then ended up moving to Singapore for me.

SM: Um, sounds like a great guy to cross paths with at the top of the gherkin. I love that you remember as well, like the breakdown and where each kind of 1- K come from. So it's really interesting so it's kind of like, you know, one thing unlocked the next and that conversation you had with the MTV exec you mentioned before was a validation point.

TA: Yeah. And a big confidence booster of like, there's something here worth Trying to like continue it.

SM: Amazing. And just also sticking with this kind of the early days for a second as well, you mentioned that it just kind of felt like the right time. Was that for you personally in terms of your life situation or was it in terms of the wider market and what was going on or indeed both things?

TA: Yeah, definitely I think more for me. So I would say that. Actually coming out of university, I'd always thought I was like a number two.

SM: Number two to Richard?

TA: Exactly. Definitely at that point. And, that sense of like being the guy who is the executor, not the sort of like front man, vision person. And I'd worked on a internet idea coming out of university with a friend who was a real like ideas person but also the attention span of a goldfish, uh, and I the person sort of like pulling it all together.

So I thought that was going to be my role potentially through my career. And then I think in my last job before starting Mito, what I'd done there is I'd gone from being the clever guy working for senior management on strategy to being given the task to roll out a product and ended up running that and growing that from nothing to 70 percent of the UK market and then taking it into international and building out big teams.

So doing that had given me the confidence of like, no, I'm more than that. I have the ability not just to think things through strategically, but also to actually execute and that was the thing that then gave me the confidence to think, well, actually I can go out and build something myself because like going back all the way, like both my parents were immigrants to this country, Norway and from Nigeria.

And I didn't really have any role models back through each of those families in terms of like building businesses. So it didn't feel like a natural pathway for me until I saw my ability to basically generate a whole division of a company by myself from scratch. And then it was like, well, actually at that point I was working in the gaming industry as in casinos and bookies, etc.

And I hated the industry. So, it was a case of like, I don't want to do it in a space that I hate. I want to do it for myself and try and figure out an idea that's big enough and interesting enough to go after

SM: Fantastic. It's kind of reassuring to hear a little bit of a theme that's emerging at least from this story where that confidence boost that you needed has come from external sources when someone who seems so accomplished, obviously so smart.

Even back during your days at school, you were I don't even know if I can list off all the accolades, but like captain of this, that and the other. And yet, you know, it was that position you had in the gaming company where you were left alone with rolling out this whole thing. The investment from the MTV exec getting those kind of external points of validation.

"Even Tom Adeyoola needs to give him a confidence boost."

TA: Well, I think, I think in many respects, that's why I sort of loved school, was that school was based on, like, here's a task, do the tasks, and if you do it well, you get validation immediately. So it's like, what's your mark against, against it? So it was really quite clear to see whether you were doing well or not in any given activity.

And, you know, I guess luckily for me I did. I was able to achieve, and I was able to succeed at many of those. So each time I was given something, I was like, I wanted more. Yeah, I was good on the sports side and I was good on the academic side. Um, and then once you come out into life, that's, that's quite different and difficult.

And certainly I didn't have, you know, I got a scholarship. And I was bursary funded to one of the leading independent schools and then went on to Cambridge and a lot of the people I knew and met had extensive networks so the ability to jump into anything quite easily of like, oh, you know, my dad has blah blah blah so I’m gonna do work experience there or my uncle is the head of Morgan Stanley Europe so I can go and do some banking there… That's not something I had.

So, and this is all pre internet days. So the idea of like, what could you be or what is out there wasn't something that was easily investigable, so to speak. So  you know, it began that sort of like democratisation through information and understanding started to come from the internet, but still it's that case of like being able to be something you need to sort of feel your way to it or have that sort of mirror built in shown back to you as though it's possible. My normal career path would have probably been in banking. I did economics at university, but I just found it exceptionally boring. And I did an internship at a bank. And then I think having been a consultant for a year, the internet world was like shiny and exciting and going to work for one, it felt meritocratic like school again, it was like, you know, a startup has 101 problems. If you can come along and take some of those problems away and solve them, you get given more, right? So you get given more and more to do. And, and that part is interesting and exciting. And it really sort of resonated with how I worked and how I responded to work.

SM: Yeah, that makes a ton of sense. I totally resonate I feel like there's quite a lot of parallels in our story in very different ways, but it makes total sense. So back to Metail. So bear in mind, you'd worked in startups. I think you said you worked in five other startups before setting up your own company. Did you start Metail with the end in mind? Did you know that you were going to build something to sell? Because you'd also had some exposure to selling companies before and your previous workplaces.

TA: Yeah. So I think in my sort of journey of working for Startups, I think at one point. I'd sort of felt where am I going to be happiest? And I thought to myself, maybe actually I love film and TV. So, I'm going to work in the film industry. I worked for Warner Brothers briefly having worked in startups and it was the most boring part of my career journey.

SM: The total opposite of what you'd expect.

TA: Yeah, because it was it was a corporate, right? It was like, we grow 6 percent year on year. We're not going to do anything else. I remember being in a meeting with a whole bunch of executives and sort of saying, look, we're going to have, you know every song in our pocket within like five years and everybody going no it will never happen.

And the key focus being on like piracy and how to clamp down. So it was all on like constrain rather than to focus on the consumer and trying to produce things that would work to their experiences and sort of generate growth. But you know, through that journey in, in film land, I ended up meeting somebody who introduced me to my wife.

So there was a happy ending from that. Now I live vicariously in film and TV through a safe distance, but I think like where I'd got to it inspired and it took a year to come up with an idea for Metail. I felt that I wanted to build my own thing and work on something, but I'd always been somebody who's quite a strong and constructive critic of ideas and they had to have like, you know, trying to work out all the reasons why something wouldn't work rather than why something would work. And so, it was a high bar for me for an idea that I would want to commit to. And in part, it had to be big enough.

It had to be an exciting enough area and there had to be means of having differential IP or technology to try and attack it. So in particular, it was like, you know, like the old Google adage of trying to work on something which passes a toothbrush test. For me, like the clothing industry was that.

SM: For anyone who doesn't know the toothbrush test, it's …

TA: … like something you do or think about twice a day. So I'll think about it twice a day. So in terms of getting dressed, it's something you do and don’t think about.

SM: Something that is just so ingrained in like your daily lifestyle.

TA: So if you're involved in something of that nature. It's a big enough global opportunity, and it's the big challenges I like. And that's the thing I realised I was driven by.

I was driven by understanding systems and disruptive change. So, the industry, per se, was not the interesting bit. It was how does the system work? And was there scope for a big change in that system through disruptive innovation in one key element and this felt like, Ooh, this could be interesting.

.

Plus I'd been trying to create the world's first live blackjack baccarat game for Inspired. And I want to use cameras to recognize cards as they're being dealt live in a casino. And, I was in Macau having you know, seen the gaming there and felt, Oh, this is going to be such a good idea.

I need to be able to try and do that. Build this and I was in my hotel room in Hong Kong. I just Googled leading expert computer vision and a professor at Cambridge was the first on the list and he had his telephone number. So there, and then I just cold called him from my hotel room. I got through first time and hadn’t even checked what time of day it was.

TA: And I've never done it before. And I got through and I said, look, I want to build this gaming system from scratch, how easy would it be? And he said, yeah, no problem! Come visit me. So, on return from the far East, I went up to Cambridge to visit him and he was your typical, open, hugely warm hearted professor who showed me all of his research work including going from Anthony Gormley pictures to fully realised 3d models of them and that stuck in my head and in the background, I ended up commissioning one of his ex PhD students to build a prototype and it worked and then I felt that computer vision was going to be the pathway to solving the online clothing fit problem.

So I thought the clothing fit problem and at the time my wife had complained a lot about buying stuff online and it just being really hard to find stuff that would suit and fit and we went on holiday to Vietnam and she had some stuff tailor made there and it was like, Oh, surely we have to be able to make the shopping process better online.

Maybe this new technology with computer vision might be the way to do that. So it was the coming together of those bits of like serendipity, if you like, which sort of made me feel like here is an idea, which is big enough to go after with a bit of new cutting edge innovation that could be applied to an idea which people have been thinking about for a long time, but which people still hadn't yet solved.

SM: This is like the essence of an entrepreneur, isn't it? It's spotting all of those different opportunities, those micro moments, that serendipity connecting the dots in a way that delivers value to an existing market need, you know, if it passes the toothbrush test as well, then even better.

So a lot easier said than done. It still feels like extremely innovative. Like it still feels ahead of its time, even now.

TA: Yeah. I would, I would say that by the time I exited we were still five years ahead of the industry. The trouble was that the industry was not catching up. So, and I think that's my big realisation 11 years after running Metail was that the fashion industry is extremely slow.

SM: Which is so ironic given that it's so trend led and there's the different season like in some ways it's one of the fastest.

TA: And I think almost that's why the underlying supply chain is so slow because things are so fast moving. You just need it by any means. necessary in any means possible as quickly as you can. That's why a lot of supply chains are still run essentially by Excel spreadsheets being shipped over long lead time, people drawing stuff on paper, like it's very old methods of delivery.

SM: This is also why Shein is doing so incredibly well. As much as it turns my stomach, as much as they disgust me, were there rumours that they're going to IPO? But, there's all this stuff about if they were like how much it would go because it's the most popular e-commerce website in the world.

Now it's overtaken all of the others because they've cracked that nut on that logistic side of things. But yeah, anyway, back to Metail, how innovative it still is even today.

TA: Where we got to in the end was that problem of the industry wasn't catching up.

And when, once you run a company for that long, if you're not getting commercial lift off, so to speak, then you end up getting caught in an equity constriction whereby you're not growing out of and into your valuation and your value. So we were in a position where I felt that only there were probably only one of 10 companies could basically exploit our technology to the fullest, the likes of your Amazons, etc.

And that was where I would have ideally liked to have seen our technology end up but in the end we got acquired by one of the big clothing manufacturers so we’ve ended up being a technology in the background rather than in the foreground for the consumer but in the background with reference to R&D on fit of clothing and presentation of clothing rather than the visualization of clothing and precipitating a better consumer experience.

SM: Getting on to the next chapter then, so the later days of Metail. So what was that whole sale process like for you? You'd kind of seen it at least vicariously through your bosses, other companies that got sold. Now this is the first time it's your baby, you're selling your business. What was that experience like?

"The guy I met at the top of the Gherkin, he became my CFO!"

TA: Yeah, so if I think, if I go back to the guy I met at the top of the Gherkin, he became my CFO. Like one of his big pieces of wisdom is that you need to make sure as a founder that you don't basically just run your company until it's dead, but you make sure you find a home for your company so that you can potentially move on to the next thing and that there is essentially a successful outcome for the business.

So you have to actually know and understand when the time is up. And I think for me, it was about getting to that point of like realization of like, well, We aren't getting the commercial liftoff that I felt we needed and then making the choice to put the company into position where we gave ourselves 12 months to then precipitate an exit and then spend the year on making that happen and doing so taking the company with me.

So I was, I was really quite transparent and honest with the team to say, look, this is where we are. And this is what's going to happen over the course of the next 12 months. And I think in particular, I'd remembered reading a segment of Ben Horowitz's book, the hard thing about hard things, which talks about that notion of like, it's always worse and harder for you than it is for the team.

And actually, you'd be surprised at how much they will basically support you through those difficult times and those hard times, if you include them through the process. And that was very much true. And it almost felt like in that final year, we were the best that we'd ever been in terms of like harmoniously working together so that two plus two equalled five rather than four or three.

Right at the end, I don't know if you know the film Brewster's Millions, it was like that scene in Brewster's Millions at the end. So he's given, I think, 11 million dollars and he has to spend it all within a month to then actually gain his full inheritance, which is like many multiples thereof.

And at the end of the month, he has to fully spend all his money. So he has nothing left, but the shirt on his back that he started the process with, and he goes through the process of getting an interior designer to design the perfect room. And he keeps saying, no, it's not good enough. Not good enough.

And then on the final day, he goes, ah, this is the room that I would die in. And then I'll go, ah, thank God. And then they clear the room. Right. So, and that's how it felt like at the end of Metail. It's like, we'd got to the perfect place of like, we were a humming team. We were working fantastically well.

And there was a pathway ahead of us and then that was the end. Yeah, we, we went through a process. We had an advisor on board but actually like the prime candidates to buy the business, I secured myself. We went on journeys to the U.S. we met all of the core players.

And it was one of those things where it's like, ah, If only we'd been talking to a lot of these core players several years earlier.

We could have basically put ourselves into a much stronger position because actually we did have something for these players and we should have started to build those relationships. It's almost we were so far ahead of a lot of them that it was going to take them a while to really understand how to how to get the value out of us because we had the biggest patent portfolio in the space by a mile so like Amazon had like five patents in their Fashion technology space.

We had over 20. I think we had more than all of the fashion industry combined with reference to consumer based technology. So it was that thing of like, they hadn't got there yet, but if we'd have built a long term relationship, they would have done, and we had a deal on the table ready to, to sort of be signed and go into a proper DD and exclusivity period that collapsed right towards the end.

And that would have been a huge deal. We could, we could very much see the value that we'd provide to that organization. That was probably like my hardest moment, I think in that, in that sales process.

SM: The fact that it all collapsed at the last minute?

TA: It collapsed at last minute and then off the back of that collapsing, my largest investor who was funding the business at the time sort of said that he wouldn't then continue to fund the business, but would buy the business.

So he took advantage of the situation really to then say, well, I'm gonna buy the business instead for…. many multiples less. So like 10 times less.

SM: Do you know what went on there? Are you able to share?

TA: I think in the case of the, the business that was looking to acquire us, I think they'd just been on an acquisition spree and they'd bought a bunch of stuff and then it transpired that some of those acquisitions weren't working and whilst they presented themselves to the world as quite a tech based business, you know, they were a floated company.

The reality behind the scenes wasn't that, so they didn't really have their ducks in a row to onboard fully technically and because they'd done a few bad things. I think their board had put a kibosh on any, any further acquisitions until their existing acquisitions had started to produce green shoots, so to speak.

So that's why that, that sort of fell apart.

SM: Is there anything you could have done with the hindsight now?  

TA: I think again, it's just that thing of like starting the whole process earlier because I think our our advisors said. Well, they might have dropped out now, but usually they come back in six to eight months because the rationale for doing the deal is still real.

It's just circumstances means that they couldn't. And I think if, if you'd have rolled forward, because I sold my company in July of 2019, if you rolled forward seven months you're into the beginning of COVID and that was then when you started to see massive liftoff in e-commerce off the back of that.

And a lot of these companies’ valuations then skyrocketed and they took the opportunity to then be massively acquisitive. So essentially like that deal collapsed, but had we, hung on into COVID, we'd have seen absolutely that come back again.

SM: No one could have predicted that. You, you just wouldn't know you could be so much worse off. You'd be so much better off. You just don't know. Like hindsight is a wonderful thing.

TA: Hindsight is a wonderful thing. And and everything is always timing. So that's that key thing then about you have to make sure you get an outcome. And with reference to then our biggest investor wanting to buy us It was like that was the best deal on the table.

I had to make sure that happened and happened in a way that was good for staff and good for share holders and the best outcome for everyone.

SM: There's a philosophy that you can only make the best decision with the information you're presented with the options available to you at that one point in time. You always have imperfect information. So it's really difficult. Doing the best that you can here and now in that moment, you never know.

TA: And ultimately you just, you just want to make sure you try, you're trying to make sure you have as many options as possible and you have some form of leverage, like the most difficult times in all my parts of my journey with Metail is like when you sort of run out of options or the options start to shrink, or if you're trying to do a negotiation on money and you're running out of money, your ability to leverage and force the best terms completely shrink away.

Yeah. So it's always about how can you try and do things earlier to give yourselves the best chance of a positive outcome.

SM: That's very great practical advice. There's not a lot you can do when you feel backed into a corner, is there? And around this time, I know that something quite personal happened. Another personal tragedy happened amidst all of this other hard stuff as well. Can you talk about that?

TA: I mean, I think, yeah, it'd been 11 years and then to see a deal fall apart. That was a real low moment for me. But then in the midst of that, like the same weekend, it, it was a case of my grandmother who I was exceptionally close to I'd spent all of my summer holidays in Norway with my grandparents and she was an exceptionally kind woman and then she ended up passing away and I think in a strange way that was something I sort of needed because it gave perspective to the situation that I was in that she was way more dear and valuable to me than my company was and going to her funeral and I sort of ended up doing a sort of vision session with an exec coach at the same time going to her funeral and going through this process of like what is everybody saying about her and her life at that funeral and what is important and what do I want people to be thinking about me at the end of my life and how important that is and getting to a point of being able to through saying goodbye to my grandmother giving myself permission to say goodbye to my company and understanding that my company doesn't define me and that was a really hard thing to try and understand because for 11 years it was Metail and Metail was me.

It was everything about me. I did everything for it and to get to a point where I was starting to consider life without it, you know, despite having a family and everything else that was a really hard moment and hard process to go through.

SM: I'm so sorry you went through all that, Tom, but obviously better outcomes at the end of you made it through. It's kind of made you into the person that you are today and it goes to show how all consuming it can be when you found and run a start up like it's just like your world, your life, your self identity. I speak to so many entrepreneurs where it's just like the one in the same thing. So in anything bad happens.

It's so much easier said than done to not take that stuff personally and not let it hurt you so much. So as tragic as it is that you went through that and during this really tough time, I love that it helped you get that perspective in that really kind of dark moment. So moving on to post Metail. So I know that you also had an experience that really taught you how to appreciate your health.

I know you're very passionate about founder health, self care. Was this all kind of another outcome of these dark days for you?

TA: Yeah, I think actually it took me a while to sort of understand about my own care, really. So, I think, I think coming out of Metail July 2019. The weird thing is I'd worked really hard to make it happen as fast as possible in the best way possible.

Made sure that the, the staff that stayed on with the company were really well looked after by the acquirer and that they got good retention bonuses. Everybody had information all the way through it. And I was like, right, I'm going to leave anger and grief until after the process. I've just got to keep my head down and get through this.

I had a very difficult lawyer on the other side, so I just had to keep the rage in.

SM: Is there a special place in hell for this lawyer?!

TA: Clifford Chance, like awful, awful.

SM: Name and shame!

TA: But come the other side, actually, all I had was like relief. And actually I wasn't interested in those emotions and I was like, right, I'm out the other side and I was then sort of focused on trying to do stuff for me, like, okay, I'm going to do a bit of fitness and this, that, and the other, and spend some time like catching up with people I haven't caught up with and then actually like within two months, then my father in law died and that, you know, my wife was in a very difficult place and I felt actually really quite lucky to have been clean out of the business because it was like well, I owe you - don't worry about family. I'll take care of that as that whole process was going on and then a few months after then it was like the beginning of COVID and it was like, well, I owe you 11 years.

So, we've got two girls. It's like, well, homeschooling, I will manage that because my wife was working at that point. She was running the script team for the TV show, The Crown. So she was like busy.

So, I felt lucky to be in the position to sort of give back and then at the end of 2020, I was thinking, okay, now I can start to think – do I start something again? And then I got a bout of terrible headaches and I couldn't get out of bed for 10 days.

And the only thing that worked from medication perspective was beta blockers. And I started to re-evaluate, like, actually what had been my situation then it was like well actually in the last year of running my company I was probably taking 30 ibuprofen a month to get through the month.

"I was probably taking 30 ibuprofen a month to get through the month."

SM: It's like an ibuprofen a day.

TA: Pretty much and I was in denial over that for probably several years I'd say, yeah, and I'd also suffered from central serious retinopathy, which is loss of focal vision in my left eye from retinal fluid leakage because of too much cortisol from too much adrenaline.

SM: Oh my God.

TA: So that I had that as well. Clearly, like I was just in denial and just carrying on that I just work on through and just do whatever to get through. And I think then me like saying, ph, I'll go back and I'll start something. I think my body was just like. I'm not happy with this!

Then the only thing that worked with beta blockers, which massively reduced my energy. So effectively beta blockers reduce your heart rate and sort of turn off your adrenaline. So I became 70 percent myself. The end of my day would be like eight o'clock pretty much. And I found it difficult get up in the morning, but that kept the headaches at bay, and I would get a breakthrough headache every three weeks. But like the difference between pre and post this headache attack was that pre the attack, it'd be like, I might get a headache every so often, but post the attack, it was like the headache was constant.

It just did not go away. It was like having a dragon permanently on your head. It was like in, in waves of strength. And so that was like a case of like, oh, okay, maybe my body's telling me not to go back into something full bore. But during this period, I still co-founded a couple of nonprofits and joined various boards.

And I was still busy. It was just like, advisories okay. Cause you just give advice and you leave. It's not the same as pushing the boulder up the hill. You push the boulder up the hill. You need 100%.

SM: So what are the big changes that you've made in your life now then since that?

TA: So, I mean, I tried, I tried lots of different things.

I had a coach for a while, like trying to like force myself back on the horse and my coach was like, oh, I think you just need to get well, I don't think there's anything with regards to how you think about work. I think it's just your health needs to be sorted out. So I've got a different regime in terms of like a medical regime.

So there's like I’ve taken a monthly injection and I take a lower dose beta blockers I'm, probably like 90-95 percent myself, I would say. Also, I think through that forced time off I’ve got a much more harmonious relationship with how I put family first and other activities And how I think about work with reference to I don't have to do everything. Like in the sense of like my value can be in the top bit and other people can do the bits below that.

Whereas I'd say I would, and almost one of like my superpowers, I'd always thought my problem was I was a jack of all trades master of none, but I realised actually in that was a superpower because it was like I could do everything. I could do everybody's job and then it was a case of like trying to hire people as you got further on in the company who were better than you in each of those areas and then delegating accordingly, but I would do as much and I could dive in if something was like falling behind and roll my sleeves up and get involved.

And I would always be like that. And I would always stupidly put myself last. So, you know, I could go days without having lunch and like late dinner and, and all of those sorts of things of like, well, I'll fit the meeting into where you know I would have and should have had lunchtime.

So it's like those things where you're just putting yourself last, whereas I'm trying to be better at fitting them around. I still fall into bad habits. Like recently I was like, ah, I haven't had lunch today. That's not good behaviour. That's not what I'm supposed to do, but I'm a lot better at sort of managing family and my time and trying to give myself permission to have off moments. And sort of like, you know, working. in bursts and out and bursts and out.

SM: Okay, that's really good to know. It's such a mental, I mean, it sounds so obvious, but taking care of yourself physically is much more a mental task. Just, just in terms of like allowing yourself to not be put last and booking in a lunch slot for you to actually eat instead of the meeting or not rolling up your sleeves and getting stuck into everything, even though that's what you're used tom and you know you're great at it.

It's that, it's that mindset shift. That comes first before all those practical bits and bobs of like good nutrition and sleep and everything else. Right. Well, I'm really glad you've come out the other side and you kind of establishing some good, healthy kind of habits. As we kind of near the end of the interview, I know that you're doing some really impactful projects at the moment.

Obviously mentioned as part of your intro, you're the co-founder of Capital Angel Network and Extend Ventures. So would you like to tell us a little bit more about what you’re doing at the moment?

TA: So I think if you like, I'm sort of involved in all the areas where I'm trying to solve problems for myself and all the interest areas in terms of like progressive societal and climate related change.

So Extend Ventures is around trying to diversify access to finance. So it's like off the back of, in fact, actually after I'd sold my company that year, I was at a conference. I ran a session on difficult founder stories. So a space for people to be vulnerable around the difficulties, how they're struggling, you know, called the struggle struggling through the process of running startups.

It's not about the cool stories. It's about the terrible stories, the tragedies. One black female founder talked about how she felt she couldn't raise any money And that she had got to the point where she felt she needed to hire a white male CEO to run her business because there was no money out there and people would say that they hire and invest in the best people and the truth is they don't. So, we met after that and discussed what were potential ways of solving that?

I think her focus was on trying to set up a fund to invest in diverse founders. And looking around these, this ecosystem, it was clear that a lot of these diverse funds were just failing to raise. So they were caught in the catch 22 of like come back when you've shown success, but I can't come back when I've shown success cause nobody's giving money. So, it was like, well, there's no point being another fund to fail to raise money. So what was the thing we can do? And it felt like the thing that we could do to help everybody and move the whole system. So again, I love systems was try and get the data on who received funding from ethnicity, gender, and socioeconomic.

The proxy we used there was university background perspective and it felt again, linking into computer vision, which is what I'd focused on at Metail. It was like, well, ethnicity is a solvable problem. Whilst ethnicity is a self-determined categorisation, in a funding conversation, it's the perception of the person with the money that matters if there's going to be a bias.

So, we can then use that. Use that to develop perceived ethnicity for founders and we can use computer vision based algorithms to do an 80-20 to the problem So 80% we can do on the algorithm then the remaining 20% is a small number problem from a manual perspective so we can we can solve that… so we looked at 10 years worth of data from 2009-2019 and we were able to show indeed that there'd only been one black woman who had raised over a million pounds in that period.

In this case, Erica, my co-founder of Extend Ventures experience was not an anomaly – it was actually the norm. And I think since we produced that report at least 10 raised over a million in one year. So the ability to start generating change, I think is, is there, and we're doing, we're launching the next version of our report soon. And subsequently it's sort of like looking at a lot of these spaces now to break them up. So Capital Angel Network is is an attempt then to look at where are their existing networks. So independent schools have strong alumni and systems and the one that I went to where I got scholarship and bursary, they've got like 9,000 on their database, right?

So one school, it's more than 500 years old, but most state schools these days are academies. So therefore they're only 10 years old. So they don't have the depth of these.

SM: Just like access to the network?

TA: Yeah. So the pathways aren't there. So how can you take those two type of entities and squish them together and create the warm pathways from the state schools into, the independent schools. So this is again, another sort of 10, 20, 30 year journey of, of trying to break down these barriers and create a virtuous circle where these are open based networks that people can basically pitch into and raise money. And then the company should be companies which are positive for society and angel investors should be donating a percentage of proceeds back into the system to hopefully generate more money.

So it should create a virtual circle. Yeah. And then in terms of the investments and companies I support, they're all sort of in the climate space, health and wellbeing, future of work and underrepresented spaces. So trying to basically generate a better overarching system for founders where there's equity and equality across this.

SM: Congratulations, Tom. It sounds like you're really having such a positive impact here. And these were all much needed initiatives and they're actually having a measurable impact, which is just fantastic.

TA: And I think they all came out of that - finishing Metail and then doing the process, which I've done for Metail but never done for myself, which is like, what are my values and what's my mission and that being separate to the company, but it's actually like, it's all my values are around all the things that I've now started to get involved in.

SM: Amazing. So this is now a result of some of that deeper soul searching for you, which is fantastic. So penultimate question. I'm just really curious to ask now that you are advising, invested in a number of different companies and with your different projects at the moment. Are there any trends, patterns, whether it's just like the top one to three things that you are noticing, regardless of founder or sector, but some of, are there any kind of problems that keep coming up or where entrepreneurs maybe keep stumbling over the same thing?

TA: Yeah. So I think we, we've definitely seen, so since I became a founder there's been this massive trend towards venture and as founders come through there is almost like overarching noise of venture funding is the only type of funding for your business. So people are shaping the companies that they're presenting to be venture style businesses when a lot of the time when I’m like then digging in deeper with people.

It's like this would could and should be a great business, but it's not a venture business and there's nothing wrong with that. Yeah, it's gonna be a fantastic business, but don't try and create something which needs to grow you know ten times year on year because you'll destroy both you and the business and there's a great thing here but it's not that shape and like this needs to be reformed and we need to have a more equalized view of the types of businesses and the flow of businesses. Because that's something actually I really thought about hard when I started Metail, which is like that spectrum of lifestyle business to like mega funded business, where was I going to be on that spectrum. And was I comfortable with that? And I think a lot of those hard decision choices need to be made early and people need to actually think harder and properly about that flow.

I saw one very recently where the founder was talking about, Oh yeah, we're going to raise now 2 million and then series A, we're going to do 10 million in a year's time. And I was like, whoa, wait one on second. What you're telling me that you figured out from the market and that you found some form of product market fit is showcasing to me that business that you're talking about, actually, you probably don't need to raise any money because that will be like a deal based profitable day one style journey.

SM: Without other people…

TA: Without other people. Yeah, and it's like if like the focus should be on how do I maintain control? And how do I minimize the number of other voices? Like interfering with what I’m trying to create.

SM: Tom I feel like that is so necessary to say in this day and age because it has been so overly glamorized, like the whole venture backed scale up style of business.

So it's interesting to you say that. Okay, final question. The best lessons can often come from the biggest tragedies. We have covered some of your darker days, some of these really horrific things that have happened in your career. What has, has there been anything in particular that's really stood out to you that's taught you an unforgettable lesson?

TA: I think all of the tragedies always related to and all of the time spent. It's always around people and getting people wrong for various different reasons. I think like in the early part of the journey, I always think about my journey of Metail, I was like, I was really good at the beginning, I was really good at the end, and there was a horrible period in the middle where I was actually just like treading water and I wasn't moving the company at the speed it needed to in the right way and hiring the right people.

And I think I accumulated too many people who were too similar in the early days and that was like really therefore they didn't gel or work together and Like that understanding of what a team should look like and the complementary set of skills it took a while to learn that and get that right and in the corollary of that really was that then my CTO coming in, he was like, he'd read every management book going and he would come in and initially he was like, right, we're going to use this management structure. And then people didn't quite work with that management structure. So sometimes you have the processes that don't work with the people and then you have the people that don't work with the process. So, it's like, how do you, how do you blend and get the right thing?

Mix is super important. So hiring and thinking about complimentary skill sets is like a really big, important lesson. I think I got certainly towards the end of how do you hire for teams and how do you also make processes work for the people that you've got? So, you know, it can be really easy to think, Oh, okay. Oh, that's right. Yeah. Everybody's using that. That's the best thing we need to, to use that. And it's like, well, is that appropriate for us? The sort of people we've got, the stage that we are and the problems we're trying to solve. Maybe actually we need a bit more control. We need to do. Things like this instead.

So that is, is hugely important. And I certainly find, especially that thing about, you know, almost hiring the wrong people. First time founders often like they're really trying hard to make themselves sound like they know what they're doing. And it's like, actually, what I want to hear is that you don't know what you're doing so that I can understand where your weaknesses are and therefore how can we build the right set of people around you to make, to give this a biggest chance of success.

SM: It's like the classic, Oh no, we have no competitors is like, never, never say that in a pitch deck. Tom, that's really refreshing. That's really great to hear. And I just want to very quickly underscore what you're saying about kind of OKRs and KPIs. Like I'm a big fan of like process and organisation, everything else.

But also as a co-founder of a creative business, the truth is you're not going to get these amazing creative individuals to suddenly kind of work to these like rigid SOPs so it's great to hear that, you know, you're not doing anything wrong. It's just you know, what works for your business.

Tom, thank you so much for coming on the show I feel like we could talk for many more hours, but I think we need to leave it there and thank you so much for listening I really hope you enjoyed this episode – that you learned something new and you took away something practical to apply to your own business journey.

TA: Thank you.

Strategy & Tragedy: CEO Stories with Steph Melodia is the best podcast for curious entrepreneurs and ambitious founders. Learn from those a few steps ahead of you in these candid interviews of the highs and lows of scaling and failing business.

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