Ashley Cain | Extraordinary Life Stories

4 Dec 2025 · 35 min · 12 chapters

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In short

Episode topic: Ashley Cain discusses grief after losing his daughter, using adversity to build discipline and purpose, and how vulnerability plus accountability can help men and communities recover and grow.

Guest backgrounds

Ashley Cain is an ex-professional footballer, producer/presenter, author, and runs multiple businesses; he also hosts podcasts. He became the first and only man to complete a major “first-in-history” challenge (mentioned as completing a world’s toughest survival/endurance race) and is preparing for further record attempts.

Key claims

when life is too comfortable he becomes “not good company,” so he voluntarily seeks “trenches” and adversity; success is “optionality” and freedom for family, not a fixed bank balance; happiness isn’t guaranteed, it’s earned daily through training and giving back without expecting return.

Notable examples

he says he lost businesses/house/car and his daughter, then built a legacy that raises money for children with cancer; he describes men at a London building site crying and hugging him after seeing his openness; he credits daily training/running as mental fitness and outlines upcoming challenges including a 1.5-ton truck pull for 24 hours and aiming for the 2030 Winter Olympics (bobsled).

Guests

Ashley Cain (primary guest).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Embracing Challenges

1:02 to 2:08

Ash discusses how challenges help him become a better person.

“I run and own multiple businesses and I occasionally do some of the craziest challenges in the world.”

Finding Purpose After Loss

2:08 to 4:38

Ash shares how losing his daughter simplified his life and gave it meaning.

“What then goes through your mind about how you decide to do something?”

Building a Legacy

4:38 to 11:06

Ash talks about creating a legacy that benefits others and the importance of accountability.

“I look back in my house, you know, my two boys, and I think what's going to forge an incredible life for them?”

Role Models and Vulnerability

11:44 to 14:02

Ash discusses the importance of vulnerability and being a role model for men.

“You might say you came from a sports background right that whole like not showing any weakness.”

The Power of Vulnerability and Strength

14:02 to 18:08

Learn how vulnerability can lead to strength and personal growth.

“But they also know that the other side of that conversation, I'm going to tell them, yo, it's time now.”

Facing Struggles and Building Community

18:08 to 20:58

Explore the importance of community support and openness about struggles.

“You've got this beautiful messaging that actually there's massive strength and vulnerability.”

Balancing Business, Fatherhood, and Personal Goals

20:58 to 25:36

Discover how to juggle business ambitions and family responsibilities.

“So, because this sounds relentless, it's exhausting listening to you, but I can relate to a point where my schedule is full on, but I'm choosing to do it.”

Defining Success and Personal Fulfillment

25:36 to 28:00

Understand how personal definitions of success can shape life choices.

“And I know that if I have one drink in this 10 months and I don't break that world record, I'm always going to blame it on a drink.”

The Importance of Training and Mental Fitness

28:00 to 29:44

Discover how physical training contributes to mental fitness and personal growth.

Challenging Adventures and Aspirations

29:44 to 31:04

Learn about extraordinary challenges and aspirations like kayaking and bobsledding.

Show all 12 chapters

Harnessing Pain for Strength

31:04 to 33:18

Explore how experiences of trauma can be transformed into motivation and strength.

“Because you got your own production company.”

The Power of Love and Inspiration

33:18 to 36:11

Understand how love drives personal goals and inspires others in challenging times.

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Transcript

Automatic transcript. May contain errors.

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0:44Need assistance? No problem. Get 24-7 professional answers and live help and access support by phone, email and in-platform chat. That's how Schwab is here for you, to help you trade brilliantly. Learn more at schwab.com slash trading. Ash Kane I've been looking forward to this do you know what it's an absolute pleasure thank you for having me tell me in your words who is Ash Kane hate that question I guess first and foremost and most importantly I'd say I'm a proud and devoted father you know to a beautiful little girl in heaven and to two amazing boys on earth you know I'm an ex-professional footballer I'm a producer and presenter.

1:26I'm an author, have my own podcasts. I run and own multiple businesses and I occasionally do some of the craziest challenges in the world. And last year I became the first and only man in history to complete a challenge. So there's a little lowdown. That's amazing. I might have missed something, but... We had a really quick challenge. Competitiveness springs to mind. You like to challenge yourself and you've also, to be fair, you've been challenged. Life's challenged you. But you've carried that on and you've embraced that. I think, you know, up until this day, going through all the stuff I've gone through, I understand that when you challenge yourself and when you have to step outside your comfort zone and when life isn't so easy, usually that's when you become the best version that you can be.

2:09I found that when too many things are going well When I take my foot off the gas And I start enjoying or thinking that I'm enjoying my life too much That's when I become a person that I don't really like that much Somebody that I can't look in the mirror and be proud of Somebody that I didn't envision myself being So I usually voluntarily put myself in the trenches For a bit of struggle, for a bit of adversity and to become the person that is willing to fight for what he wants for the people that he loves and cares about so whether adversity struck me in life or whether it hasn't I'll put myself in that position to rise you know from those ashes and be a person that everybody around me can rely on look up to and trust in you know and that's how I see myself as a man that plays you that's an thing when it because at any one time life's been made so easy we can we can order a pizza while we sit here and it'll be delivered to the door we can do countless things on our phone and yet your mindset is that's when i'm you know that's actually not comfortable in context of being comfortable and i can relate to that as well so you say you're not good company in those times how do you then decide what the next challenge is how do you get the stimulation from something you think okay i I recognise that I'm, you know, perhaps fidgety, I'm scratchy, I need to do something.

3:34What then goes through your mind about how you decide to do something? Well, do you know what it was? After losing my daughter, not only was my life increasingly more painful, hard, sad, but it made my life incredibly simple. You know, when I had to write a eulogy and speak on a day, I said that I wanted to take her to the top of every mountain, to the bottom of every valley, along every road across every ocean I said I'd take it out with daddy power I said we'd go on this this pilgrimage right and since doing that and since finding out that it brings me incredible amounts of freedom it allows me to connect with my daughter more than I ever thought I'd be able to after losing her it also raises a lot of money for children with cancer You know It benefits lives It saves lives And even if you're not a child with cancer Or a family with a child with cancer A lot of people seek inspiration and motivation from that They believe that no matter what they've been through in life They can overcome it and get through it And not necessarily run away from their pain But carry it with them And let it forge great strength So for me, it becomes relatively easy I just think of what would be an incredible journey to run for my daughter.

4:57And then I work towards it. I look back in my house, you know, my two boys, and I think what's going to forge an incredible life for them? How can they be not necessarily happy every day, but how can they be fulfilled? How can every day, if they want to push to do something and be somebody, how can I facilitate that? How can I help that? How can I look at everyone around me and my family and make their lives better instead of worse? you know so selfless and so that's just kind of how i see it you know a lot of people may look at me and you know sometimes i buy nice things that hasn't been easy you know a lot of my life most of my life i've been broke financially mentally emotionally but it's not about how broke you are it's about how rich you can make people feel around you and keep a smile on your face through the way and that's what i've always had the ability to do so it's not hard for me to think what I'm going to do next.

5:50The path is very simple. There's a legacy there, right? Which is far bigger than you. Builds on what happened to your daughter. Benefiting so many people, as you say, from whether that's awareness, raising funds for charity. And it's an instrument because I use that word competitiveness that would normally come with ego. And there's such a kind of yin and yang conversation there, which probably brings this kind of male masculinity conversation in. I've cried watching a podcast with you talking about your daughter. I'm a dad to two daughters. So I can only imagine what you've been through. To then be this strong, resilient version of yourself now helping so many other people.

6:28I want to know almost that sort of someone that might be watching or listening now that knows what you've been through, listens to what you just said then, and is struggling to pick themselves up, struggling to kind of take that next step. What advice do you give to them? Rather than advice, I just prefer to be open and honest. Most of my life, you know, even recently I felt embarrassed I felt ashamed I felt guilty I felt disappointed I felt that I'm not the person that I want to be Or that I should be Like, I felt all these emotions I'm not exempt from feeling those emotions now It's a normal thing If anybody's feeling like that It's normal, you're not alone I feel like it too I just see every single day as an opportunity for me to be responsible enough to try and do something about it.

7:20Every day resets, another 24 hours, another 24 hours, another 24 hours. What a great opportunity to get yourself out of feeling low and try and forge the way to you feeling high. Like you should be here, like you've got two feet on the ground. One thing I hate about, you know, life at the minute, there's no entitlement to feel great. There's no entitlement to feel proud. There's entitlement to feel like oh I'm going to be happy every day you have to work for it you have to do what is required to feel those things and it's hard and you never get out of it if I have a Rolex on my hand if I have a Lamborghini on the drive doesn't mean I feel like I should be here doesn't make me feel happy half of the time I get rid of these things just so I can feel a bit hardship just to go back again it's about doing what's required every single day to try and be the person that you want to be.

8:12Try and be a little bit better than you were yesterday. And one of the main things that I learned is if you do things to give back without wanting anything in return, you'll get it 10 times over, 100 times over, 1 ,000 times over. After losing my daughter, I lost everything. Businesses, my house, my car, and my child. The one thing that is the most precious thing in the entire universe. The only thing I had after that was the man that stared back at me in the mirror. And I had to make sure that every single day, the man that stared back can be proud of the person that was stood there. If that was the case, if I'd done everything I could do that day to feel better, I'd sleep at night, I'd wake up ready to go again the next morning.

8:57Such a positive message there. And ultimately, actually, one that's inspirational because it comes from within, self-awareness. So actually, you know, any number of books, podcasts, anything you're doing externally, actually looking in the mirror, having that integrity and the authenticity to just say, that's actually, that's really powerful. You articulated that beautifully because it's, you know, actually that's, that is a next step. Someone can take. It starts with you. And sometimes it's personal accountability. I had to have a conversation with somebody that works with me yesterday and I know that he's been going through the struggle and asked him how he was.

9:29And he didn't want to tell me. So I had to tell him what I've been going through the last couple of months to make him feel comfortable to share how he felt. And he was trying to say it's not good. I was like, nah, man, you feel embarrassed. You feel ashamed. I said, it's fine. I said, you know, that's how I've been feeling the last couple of weeks, the last couple of months. It's OK. I said, but one thing you have to do, you have to be open and honest with yourself first. Then be open and honest with the people around you that you love and care about. That makes you accountable. When you're accountable, you know exactly where you are.

10:00you know exactly what you have to do to get out of that you know when I went through the most traumatic time of my life yeah I had nothing to hide anymore you know I had to tell everyone that I loved and cared about around me exactly what I was going through all the things that I'd done what I was doing now because I had to bring myself to the ground the real ground the real ground zero because when I was at ground zero only then could I lay the true foundations to build this empire, this legacy, this house that can hold everybody. You can't stop building halfway up. You have to build from the ground the foundations.

10:35And that starts with openness. It starts with honesty. It starts with accountability. When you've got those things, you have a solid foundation to go that way. Study and play. Come together on a Windows 11 PC. And for a limited time, college students get the best of both worlds. Get the Unreal College deal. Everything you need to study and play with select Windows 11 PCs. Eligible students get a year of Microsoft 365 Premium and a year of Xbox Game Pass Ultimate with a custom color Xbox wireless controller. Learn more at windows.com slash student offer. While supplies last, ends June 30th. Terms at aka.ms slash college PC.

11:13Get business done with the new American Express Graphite Business Cash Unlimited card. With unlimited 2 % cash back on all eligible purchases. unlimited 5 % cash back on flights and prepaid hotels booked through American Express Travel Online, and a flexible spending capacity that can grow with your business, you'll have the confidence to keep building. Apply today and earn a welcome offer of$1 ,500 cash back after you spend$50 ,000 in qualifying purchases on your new card within the first six months of card membership. Terms apply. Learn more at go.amex.com. So talking to you now, thinking about this before we were going to talk, talking to people about you, knowing I was going to talk to you today, I brought up role model and I brought up leadership and the fact that I know I can have a man-to-man conversation with you that dare I say I have with many people in private close to me but not something that was done publicly 10, 15, 20 years to hold man up.

12:08You might say you came from a sports background right that whole like not showing any weakness. You might have pulled your calf in training or hamstring playing football last night. You tell the lads the next day and everyone goes you know i'll have physio but you don't say i'm struggling with my marriage you don't say i've got financial issues you don't say i just i think i might be depressed yeah because you're worried that's the word embarrassed you know i'm going to feel weak you flip that narrative and we were talking about the uh the sort of learnings i've got from the csj the center for social justice and the lost boys report which gareth southgate referenced in the dumber we talk and this crisis in lads with role models listening to you you are such an amazing role model you know it's it's real and it feels like role models that are the wrong type that have got Lamborghinis but shouting about it have got an ego and want to sort of in a way shout about that as well and that's risen to the top whereas talking to you it's far more powerful are you in any way getting feedback that what you're saying how you're saying it is so important do you know what's great um even even from the time of you know being in hospital to now yeah you know what i was getting in my dms was a highlight to how many people were struggling and also like how important my openness my honesty my vulnerability but then the strength of the other side of it was yeah and such an incredible thing is you know you expect if you're going through a tough time or you show that vulnerability a lot of women to be you know the ones that are coming around you and and and and showing their vulnerability and sharing things with you one of the most revolutionary things has been i walk you know through london and there's a building site and there's like four lads running off a building site one to give me a hug two of them are crying some of them are talking about you know how my journey has changed them as a father some of them are talking about you know they're not a father yet but watching me and how devoted I'm to my kids has made them want to be a father want to do the best as a father change their lives that you wouldn't believe what some people tell me and I'm glad they do I feel honored and privileged and I know the reason why you know I'm not afraid to cry in front of anybody I'm not afraid to share the good parts of my life but most importantly I'm not afraid to share the bad parts and what I try and show is yeah it's not just about being vulnerable what I try and show is the strength at the other side of it the pathway to being successful at the other side of your pain the power at the other side of your pain the strength at the other side of your struggle so then when people come up to me they know they can be authentically themselves they know if they're upset they can talk to me because they've seen me do the same thing.

15:01But they also know that the other side of that conversation, I'm going to tell them, yo, it's time now. We've got to stand up. A lot of the struggle that I had in the first place, having these conversations, especially on TV, was always trying to say that talking is not enough. What we need to be doing is showing these young men a pathway on the other side, feeling competent, feeling capable, not only being able to share your emotions or share your problems or share your traumas, but teach them how to build the foundations at the other side of that to recover, to grow, to climb over all the boundaries, all the barriers, all the hurdles that sat out in front of them.

15:41And that's what I try and do. You do it well. I mean, it's the classic leading by example, which goes back to being a Rommel. I don't know. You try, you're not put like, I don't want to sit here and seem like I'm perfect. I'm not. I still have these battles every single day. I still like, you know, disappoint myself and I'm still trying to be that little bit better. And I'm trying to be a person that can help other people. I'm trying to be a person that can provide. I'm trying to be a person that can protect, you know, all while trying to, you know, fight my own demons. You know, I said a funny statement the other day to somebody, someone was saying, how do you do all these things that have never been done?

16:15I said, because I'm willing to do things that no one else does. And rather than decide to fight my demons every single day, I decided to be the biggest one and go and jump in the trenches. I heard that whisper, it's time for the trenches. I said, I didn't reply, I just jumped in. I was ready for it and that's where I get my enjoyment it's really strange I don't see I don't believe in happiness that's going to sound quite cynical it's not I believe in happy times happy moments happy memories things that we live for yeah but there's no such thing as like concrete happiness because there's so many things in the world that went to just sucker punches bang every single day how do you overcome that I get my contentment from looking around me and thinking everyone else is okay.

16:58That's when I genuinely feel happy. I'm like, yo, I took the family on holiday. Oh, we're having a nice family park where we cook food for everyone, the kids running around there. That's where I'll get my happiness. And I'll run through effing brick walls every single day to get that because that's what makes me feel like I should be here and as one. And that is my genuine light in my heart. That's a real tribal, beautifully articulated a real sort of tribal mentality where you're happy if everyone else around you is, which is of course why you know when you lost your daughter and that was out of your control that that was out of your control and that whole thing must have been horrific but right now and how you encourage and again show people in a role model way how to be to have a good time and so on and then you thrive off seeing that happen I think one of the things I wanted to say to you just championing that whole strength and vulnerability you're a strong guy you know you You could look intimidating to someone.

17:56And you've got guys that come up the building site and give you a hug. And those guys themselves are probably big old scaffolding lads and so on. And there's damning stats in the mental health side of things, in construction, if you like. You are relatable. You've got this beautiful messaging that actually there's massive strength and vulnerability. But there's communities that can come together around it. I know you had another question there, but one thing that people say to me, do I feel like it's a burden? I absolutely don't. you know I love people I love communicating I love feeling like a person can feel better after they spent time with me than before they did yeah that that's a blessing but it also made me realize how many people are struggling in this world it is frightening and it's only frightening because those people aren't willing to look at the person next to them share it and realize that that person of going through the same thing.

18:52If that was the case, we'd all be able to lean on each other and become pillars for each other and support the people around us through all the rubbish that we have to go through, all the things that life throws at us, all these testing times. If you knew that the person next to you was willing, you know, to stand by you or willing to be a shoulder to crying or, you know, somebody to release, you know, half of your problems with, like the world would be a lot easier and it's having that confidence but I think first it starts with that accountability within oneself to feel comfortable to do that and also I think the scary thing about being open is it's not so much you know pride what it is is if you're open about something then you have to be prepared to do something about it if I hide something from you you can't put no pressure on me to be different as a result of what my problem is if I share it with you, then you can be like, what are you going to do about it then?

19:47And then that's when the real work starts. Yeah, definitely. I feel really privileged to be talking to you today because I know how busy you are, you know, and you are a man in demand, you know, very important to a lot of people. And then you're putting yourself out there as a businessman, an entrepreneur. And I wanted to open that up. You know, there's so many things you're doing. And I want to almost know firstly how you're almost juggling it and two, the kind of why behind your business interests. I've really struggled the past year it's been really difficult and I guess the reason is because you know pre my daughter you know my life was just about me me me so I could run around and just do whatever I wanted yeah and there was no pressure on how successful I was here or you know how great I was there it was just me being a frantic young boy in his 20s living life to the max you know then you can take different risks and think differently don't you yeah post my daughter So, you know, I lived every day just trying to be a savage to get through it, to complete some of the hardest things in the world, to raise as much money as I could for the illness that took her away and to take her around the world.

20:52And for her to know that any given time that she looks down, her daddy cares about her and her daddy will fight for her and her daddy will die for her. yeah and then you know as a result of me like turning down so much work because i just had to do what was in my heart and not sat out i end up getting 10 times as much because i would stay true to myself yeah and then it became like okay you know you want to be one of the you know most insane guys in the world doing this then you've got a really big kind of empire in terms of career like producing presenting businesses you know contracts brands partnerships all of this kind of stuff and then trying to juggle the two like was quite difficult and then I had two more boys two boys under two and the thing is about me which everyone knows is I am a present father you know as much as I possibly can be you know within that realm of still being able to provide and that was when it became slightly unmanageable it was like running from A to B is easy you know when you've got A, B and C and it's a triangle which way do you go do you run around this way do you go back and forth this way because i'm trying to be a super successful businessman i'm trying to be a super successful athlete i'm trying to be more than anything a super successful father and then you've got all these other side projects i'm doing which a lot of time means that i go to bed sometimes at like 1am and then i'm up at 4am and that's just this is the insta versus reality right that's just the reality of it mate you know yesterday you know i trained twice three times and i'm out putting a three-ton tractor in the field because i'm trying to break a world record next year that's just what you got to do then i'm getting back and i'm and i'm working to hit deadlines you know in a couple of months i'll be flying away to film the next series of my documentary i'll probably be away for three months again flying to uncomfortable places around the world meeting uncomfortable people missing my family do you take comfort for the fact that you chose to do all this.

22:54So, because this sounds relentless, it's exhausting listening to you, but I can relate to a point where my schedule is full on, but I'm choosing to do it. Does that, does that, do you remind yourself of that? If not, I'm trying to do that to you now. I ain't got no problem with it. You know, my manager's sitting here. I tell my manager, if there's an hour in my day free, do not ask me whether I can work, book it in. Fair play. So you are, you are set up for efficiency. You're set up to be effective. I'm set up to be a horse of war. Just get on and it doesn't matter where we've got to go. Just put the straps on and let's go.

23:30Because I know the uncertainty of life. Like I said to you earlier, there's probably been more times in my life when I've been broke and had nothing. There's been more times in my life where I've had to battle and work 10 times harder than anyone else because of who I am, what I look like, the area that I lived in, the friends that I had, the situations I've gone through. So there's no guarantee in my life. so it's like I don't like to have the time off I don't like to sit on my lulls and think oh that's enough because you never know what tomorrow's going to bring or the next year's going to bring and now when you've got like a household to keep and you've got like other family that you try and look after you've got your kids yeah I can't be taking no risks you know because they're important whatever they need they have to have so then my life's changed yeah like I don't I mean I went on holiday i took my family on holiday you know now i've got the boys and stuff but prior to that i didn't go on no holidays i don't go out for food apart from if i'm working i have to eat i'll just find like enjoyment getting in my house and seeing everyone i love and care about and apart from that i'll just grind it out and i had to get back into that mentality couple of weeks ago you know and this is what it is it's it's a tough time in the economy at the minute it's a tough time in every single area i got back from the holiday which i took my family on and i was like stop drinking now for 10 months drinking wasting money drinking making me unproductive drinking making me feel bad drinking making me wake up and not be able to enjoy the next day drinking probably causing me to act in a certain way that could lead to something stupid stop locking and then when you've done what you want to do in those 10 months when your businesses are succeeding when your projects are working when you've been a proud and present father every single day because you're not hung over and when you broke that world record then on your birthday you know have two months and enjoy yourself until then it's go time because then you know what it is i always say something if i set myself up to achieve something i don't mind telling every single person around me they say keep it secret nah i'll put myself accountable i'll tell everyone what i want to do and then i I hold myself accountable every single day.

25:36And I know that if I have one drink in this 10 months and I don't break that world record, I'm always going to blame it on a drink. So it's not worth the hassle. We're sitting here now. It's just like out of the question, you're not going to smash that world record, right? And you are just formidable to be around. You mentioned the word success a few times, big successful businessmen. I'm interested because I really relate to what you said about happiness as well. Like striving to be happy is kind of a fool's gold, right? What's your definition of success? my definition well number one I already know that in this lifetime I'm never going to reach the place where I want to be that's fine because it's always about the journey anyway it's never about the start it's never about the end it's about who you become and what you experience in this place in between so I'm not trying to you know hit a certain goal in my lifetime I'm just excited to have that goal and every single day that I live and breathe be able to work towards because then I'm being the better person creating a better life but my terminology of success it isn't like a set number um to having a bank account it's not a set amount of properties or whatever do you know what it is it's like if I want to do something whatever I want to do I can afford to do it if my kids you know and that might be time off working to spend my family it might be you know the amount of holidays I want to go on it might be you know if they want to become a professional tennis player it might be if just my family being able to spend as much time with each other in the right environments and push towards what they want to do it's just it's just about the freedom to do what i want optionality yeah and i'm not like a real i'm a pretty basic person mate you know like if i didn't have my family i literally could live in a tent like i'm not really that bothered what's really important to you in context of through this busy schedule and life you've got right now making time for yourself whether you know probably goes back to even what you just said you stripped everything away do you have that sort of morning routine away from the fact that you know sometimes it's a one in the morning finish get up early but making that time for yourself what's sacred what do you do that's almost sort of non-negotiable There's definitely one thing that I know for sure.

27:49It is that training is an absolute must in my life. I haven't trained to look good in five years. It's about feeling. Your mental mental stuff 100 % I understand that if I don't train that day I'm never going to feel good Or as good as I could be I understand if I don't train that day I'm never going to be as good as I can be to everyone else around me If I don't train that day I know that I'm not going to work to the level that I can work at It's a fact 100 % And also I know that if there's a period of time when I haven't trained And I feel lost And I feel like I don't know how to even put one foot in front of me of the other that as long as i just go out my door and run when i come back in it's like i never left bang that's that's one thing i have to do in my life and you know i lift weights and i run i mean i do loads of i do loads of stuff i jump out of planes i can't climb mountain i was going to come to this yeah and the reason why i was going to come to it is like the it's very clear and you're really smart but actually you know the men the mental fitness comes from the physical exercise if you're if you're training from a football point of view you're training for the next game the next competitions you've got like that competitive it's stimulated you haven't got that i haven't got that when i go to the gym this morning i'm just trying to fire this up my brain up and probably trying to look my best as well that's it so you with that competitive element to you can put it into a challenge and of course it's a world record coming up but is there something that you would love to try is there something that you've got as a sort of a north star because you're there's an unhinged side to you i can imagine you've had some thoughts about some pretty serious challenges is there one that you're eyeing up okay so so there's two things i'll bring to you completely different but you know both equally as important so when i became the first man in history to run sark and kayak the length of great britain you know land's end john o 'grose so when i was at land's end yeah there was a sign to john o 'grose and somewhere else okay ran a thousand miles got to john o 'groats then there was a sign in john o 'groats to land's end and somewhere else i was like got my bike circled a thousand miles down to land's end and then like i seen this sign again john o 'groats somewhere else and you know i got my kayak started kayaking around great britain and i was actually kayaking with the world record holder for circumnavigating he's a crazy guy I said to him Dougal can you kite from New York to London and he was like guess so I said has anyone ever done it he went nah I mean would you be up for it he was like yeah across the Atlantic Ocean possibly the most dangerous thing you could do but to be the first man ever to kite from New York to London would be absolutely incredible and you know what i want to do is i want to give i want to give it a few years i might become an old man before i do it so i can experience my great beard well in case i don't make it you know i mean i'm fully aware of that but that is that is one that i want to do before you know my life ends because i won't be able to forgive myself if i don't but one that's um a lot sooner is i want to go to the 2030 winter olympics bobsled i want a bobsled i want to captain i want the 2030 Olympics.

31:13It's a film coming. There you go. Because you got your own production company. 100%. Well, you know, as a kid, yeah, I remember like, you know, I wanted to be a footballer and I became a professional footballer. But one thing that my family has always done is they've always been athletes, yeah. And then some of my cousins have represented Great Britain for sprinting. And the Olympics is something that we watched every year. And we talked about Olympians like their gods, yeah. I did actually qualify for a Team GB bobsled, you know. and then when I lost my daughter I realised I had to go on this pilgrimage and take her on a journey rather than pursue that but then I thought you know what yeah over the years the amount of things that I've done the amount of money that I've raised and then completing the world's toughest survival endurance race becoming the first and only man in the history of the world then next year hopefully breaking the world record I've done the treble and I thought what a four-year journey it would be and what a great ending to then take her to the Olympics and be an Olympian that's some cv that isn't it it's amazing and i don't even i can see you doing it like this you know i just thought i just thought if i can take her to the olympics yeah and then that's the real testament yeah because the reason i want to do this challenge next year it's um a 20 it's a um 1.5 ton truck pull for 24 hours yeah and the reason why i wanted to do it yeah is because everyone always talks about being able to move on from your problems or your traumas yeah i'm like nah like because you know a lot of my traumas are the best things that have ever happened to me you know losing my daughter yeah would i have like would i have not gone through that you know i'd i'd do it again and again and again and again i don't want to forget about her i don't want to forget about that she is she is my love she is my power she's my strength i i move on life with that i carry that with me i pull that pain i pull that trauma i use it to catapult me to greatness yeah and so the reason i wanted to pull that pull pull the 1.5 ton truck is because there's so many things in life you know that have happened to us that have hurt us that have caused us pain causes anger you know and a lot of it we didn't deserve but you know we can't sometimes unshackle these chains sometimes we've got to be strong enough to move forward with it so i'm showing people yeah physically and metaphorically that no matter what has happened to you you have the power to greatness with it without it whatever yeah and then after that you know going to the olympics i just thought you know now we're going to push them now you know now now we're going to push all of our stuff that's in front of us i'll just i've just met i've got metaphors for everything and i usually do things based on how i'm feeling and all i'll do bro is i don't have this methodical plan i'll just go yo i want to run cycling and kite and then for the uk yo i want to go to the olympics yo I want to put a 1.5 ton truck for 24 hours and it's as simple as that and they just work back you don't just sow the seed you you start watering it and you literally start making it happen like if we if we had a conversation now about something that in any way became uh solidified you'd be on me and I'm unbearable no I can imagine I know I know I'm unbearable yeah and what I end up doing you know like you said you mentioned something to me at the start of this conversation and you said I could come across as quite intimidating yeah and I know that yeah so I try and make a beeline to be the opposite way to make people feel uncomfortable so before we do something like and if people agree I try and solid up like try and make sure are you sure you want to do this because this is going to be what's required this is what we're going to have to do but if you're in unfortunately you are effing in yeah and I'll be beasting you yeah and we and we are yeah you'll go to sleep see my face you'll wake up see my face it's on you yeah i mean you're like your inspiration to be around like you yeah and and you know just wouldn't bet against you making anything happen once you put your mind to it but you've got to say this right how you feel right people always say ah you know is it courage like courageous strong resilient all this i'm like no you know what it is i just i've got a big heart and i love a lot and love is by far my strongest power it's not courage because i'm scared a lot of the time it's not resilience because a lot of the time i don't want to do what i have to do it's not strength because most of my life i've been broken it's just this unimaginable and undescribable amount of love that i have and what i'm prepared to do for it and and i think all of us in life have that love it's just not being afraid to access it and to use it to push us to where we need to go and from my point of view and anyone watching listening to spend time around people and listen to people that have got that that you can actually take some of that cut pour it into yours you're doing that for me right now but i'm a pretty motivated driven person but you know i and we're out of time i could talk to you for another hour right but that's my biggest takeaway from this conversation with you is you are an inspiration ash thank you and um you i can really feel you brought your daughter along with everything you brought her today.

36:18You're taking her onto every challenge you do. And, you know, I said I've cried watching you before. I'm smiling ear to ear right now. It's such a positive force of nature sat in front of me. And thank you for making time in such a busy schedule. I absolutely love talking to you. Thank you. It's been an absolute pleasure, man. Really appreciate it. No pleasure. Legend. Ryan Reynolds here from Mint Mobile. I don't know if you knew this, but anyone can get the same premium wireless for$15 a month plan that I've been enjoying. It's not just for celebrities. So do like I did and have one of your assistant's assistants switch you to Mint Mobile today.

36:53I'm told it's super easy to do at mintmobile.com slash switch. Upfront payment of$45 for three-month plan equivalent to$15 per month required. Intro rate first three months only, then full price plan options available. Taxes and fees extra. Default terms at mintmobile.com.

From the publisher

In this episode of Extraordinary Life Stories, John Reynolds talks with Ashley Cain.


Ashley is an English reality TV personality and former footballer who played for Championship side Coventry City.


Ashley’s lost his daughter at 8 months old after she was diagnosed with an aggressive form of leukemia at just 8 weeks.


In this programme we discuss overcoming life's challenges, personal transformation, and finding strength through difficult experiences, including navigating profound personal loss and maintaining a positive perspective.

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