Back to Blog

How Speaking And Stories Can Change Lives - The Caspar Craven Story

succeed through speaking tom bailey Apr 04, 2022

Tom Bailey, founder of Succeed Through Speaking, interviews Caspar Craven.

In this episode we hear about our guests journey with confidence, public speaking and presentation skills and how it has helped them succeed in life and in business - in other words, how to succeed through speaking.

Caspar Craven is a Serial Entrepreneur, Former CFO and Adventurer. He is a leading authority in Achieving Big Bold Goals through High-Performance Teamwork. A serial entrepreneur, he has built and sold a tech business for a 7 figure sum, worked as a CFO and at KPMG. He has twice sailed round the world – the first time as a team leader on a trophy winning racing yacht in the BT Global Challenge in 2000/1 and the second time as captain and team leader of his family team in 2014/16 with his wife and three young children under 10 years of age.

Resources / Links

More from Succeed Through Speaking

Succeed Through Speaking helps Coaches, Consultants, Entrepreneurs and Experts how to amplify their Expert Authority & get their message to market with both confidence and clarity so that they can raise their profile and attract new clients.

Take the Expert Authority Scorecard -

Join our upcoming training -

Listen to the Podcast -


Tom Bailey  00:07

Hello and welcome to succeed through speaking the place for experts and entrepreneurs who want high value ideas to boost business results Hello, I'm Tom Bailey. And in today's speaker stories episode, I'll be getting to know Caspar Craven, who is a serial entrepreneur and a leading authority in achieving big bold goals through high performance teamwork. He has built and sold a tech business for seven figures, and has also worked as a CFO and KPMG in previous roles. So Caspar, hello, and a very warm welcome to today's episode.

Caspar Craven  00:51

I Tom Great to be here with you. Thanks.

Tom Bailey  00:53

Yeah, thank you so much, and just out of interest whereabouts are you in the world right now?

Caspar Craven  00:57

So today, I'm in uh, sorry, just outside London. So nowhere particularly exotic?

Tom Bailey  01:02

No, no, but I'm sure you've got some speaking, gigs lined up this year, hopefully abroad as well. And but we'll get on to that. So thank you so much. For that, I just want to just share a little bit more about you before we do get started. So Caspar has sailed around the world, not once, but twice. And the first time he led the team on a trophy winning racing yacht in the BT global challenge. And the second time as a captain of his family team, with his wife, and three young children who I believe were all under the age of 10. At the time,

Caspar Craven  01:34

they were like my children as well, which always helps,

Tom Bailey  01:36

great that you can tolerate them.

Caspar Craven  01:39

In the internet, some children, other minds.

Tom Bailey  01:42

Great. Well, thanks for that. And we'll talk more about that I'm sure as we go. And we've heard a little bit about your background in business and those incredible adventures that you've been on. I'd love to know more about your journey with public speaking. So how did this come about? How did you become a speaker? And have you always been a competent speaker?

Caspar Craven  02:01

So let's get let's let's, let's dive straight into it. So like I said, when I was at school, I was bullied a lot. And I learned the safest way to sort of live life was to keep my head down. And to never sort of speak out. So I was the last person in all schools that I was at, you would ever pick to becoming a public speaker, I used to hate it with a vengeance. So I could never imagine myself doing that, through my, my conventional career, to KPMG, and so on. I had to speak at events and things like that. And I was terrified of that hated that. And, again, the thought of going and standing on stages was the last thing that I would want to do. However, that didn't change. When I came back from my second sailing adventure. And I'm paraphrasing a lot of stories in between. And we had this amazing experience, and I sort of in the journey to make all those things happen. I realized that I learned a huge amount. And I remember thinking, You know what, there's something it'd be really criminal if I just keep these ideas to myself. And I remember going and getting invited to do an after dinner, speaking gig. And the feedback and the reaction I got from the from the room was just unbelievable. And I remember thinking to myself, you know, what, if I can share stories, and they can have such a profound effect on other people, I said, literally then and there, this is what I'm going to spend my next 25 years doing this, because it's the most meaningful thing that I've ever done in work in the working world to use the power of stories to change someone else's trajectory, currently think. So. I was hooked at that point. And that started me off on a journey, a long journey to learning metal speaking business.

Tom Bailey  04:00

Amazing Love that great, great journey. And there's two things I want to pick up on there. First of all, the avoidance of speaking at school and beyond. And then secondly, I think we'll talk about you mentioned it would have been criminal had you not shared these these ideas through storytelling, so we'll go into that as well. So, first one, just to reflect on avoiding public speaking, I was very, very much the same not through bullying, actually just through, I think a form of social anxiety, a fear of being judged by others. And again, that wasn't because I was being bullied but because I thought maybe I would get bullied if I embarrass myself. So just on that point there. I personally became very good at avoiding public speaking. So what were some of your strategies to avoid public speaking that you implemented

Caspar Craven  04:46

it? I think he was putting your hands up who wants to get involved in this you'd be the last person to do that. Yeah, like the worst thing was any when you room with people at Salomon being at different work things, and you got to room with eight people, you've got to go around the table. You're going to introduce yourself. You just got a horrible feeling in your stomach. And it's just like, you can't you don't hear what anyone else is saying, because you're so terrified about, you know, what are you going to say? Am I going to look like an idiot? You know, all those sort of horrible thoughts going through your head. So like you, I would just try and avoid it at all costs and not be in this situations? Yeah. Inevitable. Sort of, you know, work your way up the corporate ladder that you're going to have to do some more of that. So I gritted my teeth and did it. Yeah.

Tom Bailey  05:35

Yeah, that really takes me back to being in a team of 10. And I was the eighth person to speak. And it just gets progressively worse that feeling of dread that fear, you're going bright red and shaking before it's even got to you. I can definitely resonate with that.

Caspar Craven  05:52

Getting sweating even just Yeah, I know. It's taken me back. Yes. Yes. Being there. And, yeah, you just want to get through your words as quickly as possible. And you're not enjoying the situation. And yeah, yeah, just get me get me through this.

Tom Bailey  06:05

Yeah. And I think you know, a lot of this has a lot of psychology behind this. But it's ultimately that fear of others opinions, fear of judgment, fear of making a mistake, embarrassing yourself, having people laughing at you. And all of that is there. But like you said, just gritting your teeth, you did it anyway. And then did you find that once you had started to do it, did it become a little bit more comfortable? And did it help with your career trajectory as well, once you did start doing it.

Caspar Craven  06:29

So when I was in the conventional corporate world, never particularly enjoyed it. When I list on launching my own businesses in in the early 2000s, actually became quite an important way for us to share ideas, and I developed a number of different ideas. And actually, I started to enjoy us a little bit more than sharing those ideas, because I had important things that I wanted to share. And you remember making the mental switch, actually, it's I made, let's say, half made the mental switch. And it's not about you, it's about the impact on the other people. And they want to hear the ideas. And that's that's a theme that I've definitely developed through my speaking. But in my entrepreneurial world definitely got more comfortable with it not entirely, but more comfortable. So

Tom Bailey  07:20

yeah, that's a huge point about pivoting the spotlight off you towards the audience. And you can really think about how much value can I add or give to this audience through my stories through my expertise through sharing, that's where my focus should be on not? Am I going to trip over my words? Am I going to make a mistake? Am I going to embarrass myself? It's how much value can I give to this audience? I think it's a great way of reframing your perspective.

Caspar Craven  07:45

Absolutely. I mean, to extend that now speaking that I do mean, it candidly speaking, that no one no one gives a shit about your story about what's the impact that this can have on me. Yeah, that's a classic mistake, I think that so many speakers make and I made it for a long, long time thinking, it's about me and my story. It's got nothing to do with you. You're just vehicle for delivering a set of messages. And it happens to be through the metaphor of story. But it's not about you. The sooner that that switch can be flipped, the better.

Tom Bailey  08:16

Yep. Perfect. Great. And so I'm gonna just jump back then to that second point around you mentioned it would have been criminal had you not shared this message? So the question I'm gonna frame is that this podcast is called succeed through speaking, or does that make you think of how important is speaking to yourself in business or in life in general?

Caspar Craven  08:39

How important is it? Seller? I mean, it's the it's the the IRA now is the gearing and standing on the stage and sharing stories. It's the most impactful thing that I absolutely love doing now. And yeah, give them a preference. Absolutely love it. So yeah, that's pretty much what I can say about that. And then the ideas that comes through that, again, just having had all these different experiences, I know when I've when I've shared these ideas and got down to detail and workshops, people, and you hear the stories that happened to people, not just in the moment because people go way off for talk and they get busy and they get excited. But then you hear the stories one year down the line, two years, three years down the line of how their world has changed. And it's just like, you know, what, that's truly truly meaningful work. Therefore, it's like, okay, the reason that I go into get better at what I do is that I can impact more people. And that is, that is the sole thing that drives me. And you know, a number of gigs I get how much I get paid as a as a result of doing the other thing first, which is focusing on the impact. Yeah,

Tom Bailey  09:51

I think that's a really good point about impact, because you know, had had you wanted to impact lives, one at a time. time, it'll take you a lot longer than filling a room of people and impacting all of that sometimes it's just a great way to leverage your time have more impact through using the, I guess, medium of speaking. So yeah, that makes complete sense.

Caspar Craven  10:16

What's the thing you know, we're sort of speaking for a company on the continent next month. And this, I think it's like 30,000 employees from speaking 260 senior leaders. And you just think about the ripple effect that goes out on that, that potentially, you can touch 30,000 people inside the company, plus their families, let's say, for people in the family, but you can suddenly see the ripple effect the potential for these ideas to germinate and spread. I occasionally speak at schools. And again, I think about the same thing that the amount of ripples that that can have. So it's not just the immediate audience, the audience that that sits beyond that. So it's an incredibly privileged position to be in to be able to share share success stories that can travel,

Tom Bailey  11:00

the love that and that ripple effect almost puts your slight fear of embarrassing yourself to insignificance really compared to what impact you can have. So I guess a lot of people that listen to this podcast, my audience, are scared of public speaking, they may not be doing it yet, because they have that fear. So I guess, instead of thinking about what could go wrong, if I do it, you know, what could go right? If I do it, what impact could I have? What's that ripple effect that I could have? over my lifetime to other people's lives? It's worth just getting over that fear is what I'm trying to get out of?

Caspar Craven  11:34

Politics. And so I've got two, two things that I've used around that. The first one, which I don't really need to use anymore, because I'll explain why in a second one, but the first one as I remember, I remember having a scary moments, he was actually on one of our sailing adventures, and you've got a life threatening moments. And you're there with a child of yours. And you think he is slightly that's proper, scary, getting stand in front of Ruin in bunch people. It's like, which one would you rather be in? Yeah, there is love contest. When you put in different contexts. That was the scariest thing that's ever happened to you. And then there's this, and we can all find something where we've been terrified, right? Yeah, that's the first that's the first lens, that switch. And then the other one is just on 100, literally 100% Focus on the audience. Because if you are focused 100% on the audience, you haven't got the room to think about yourself, I think you've met is the impact they're going to have, then that there is no room to think about you. So it's, it goes out the window. So

Tom Bailey  12:32

perfect. So we talked about that first keynote dinner presentation that you did, which went really well. And, you know, you might not want to talk about these, but have there been any speaking experiences that you remember, that didn't go? So well? Was there any mistakes or anything that happened where you maybe wished it hadn't gone that way?

Caspar Craven  12:54

Now, they've all been amazing, Tom, you have the say, like the I'm sitting in my studio right now. And on the wall over there is I have these sheets. And after every single speaking gig, I go through and I score myself Great. Well, even better, if the fan literally every single thing that I'm doing and taking taking it apart, asked after every single piece of feedback that I can get. So for me, you know, this is this is my mission. And it's that game of continuous improvements. And yet there's been some hours for sure. And you don't get the reaction that you want. And yeah, it's just sort of, yeah, the uncomfortable silences afterwards, and that sort of stuff. So that you need those because the feedback is there's no way on earth, you can start off in any business and just go straight there to be an amazing, it's just impossible. So therefore, it's that continuous iteration. And you know, I have this mantra in my head, you're not good enough yet. And, you know, I'll never be good enough. And it's just about saying, Okay, how can I improve? And I'll take apart, you know, one, two minute segment of the talk, say, okay, how can I make this better? What can I improve? And then I'll work on another segment, and I'll be speaking to other speaker friends, and we're comparing this with swapping notes, and watching other speakers and just like, continuous students of how to make it even better. So it's a never ending journey. So

Tom Bailey  14:27

yeah, I love that so much. What I wanted to claim is that there will be mistakes, things will go wrong, but almost, you know, accept them, look for them, bring them on, because that's where you're gonna learn the most and you're gonna keep improving. So yeah, I love that way of framing it and actually having that big sheet on the screen to give yourself feedback and score yourself as well.

Caspar Craven  14:47

Yeah, you're probably always not fumble brutal. No one else will be but but that's how you get better, isn't it? So?

Tom Bailey  14:53

Yeah, and if you do struggle with that, you may well be able to find a coach who can you know, give you some feedback as well or ask you those difficult questions. So we've talked about people who are maybe at the very beginning of their journey, they are thinking about wanting to speak, and we've given them lots of great advice and value. What about people at the other end of that scale, they have done a little bit of speaking, they may well have stood up in front of a couple 100 people before, but they've never been paid to speak. So what advice would you give to somebody wanting to pursue a career similar to yours and actually end up getting paid to speak as a career?

Caspar Craven  15:30

Okay, so the first thing is to be incredibly careful about who take advice from, yes. There's, you only want to be taking advice from someone who is a good way ahead of you, I've been tripped up by so many, well, meaning people have given me advice. And you end up going down countless rabbit holes. So you know, find someone who is in the place where you want to be, you want to do find a way of adding value to them. And, you know, get glean whatever advice that you can have very fortunate, earlier my speaking career career to get to know, very successful speaker, and he's given me some fantastic advice. And you've seen me talk a few times and regular times, like, Okay, give me some pointers, give me some guidance. So the first thing is just sort of, yeah, getting as much good feedback as you can from people who have earned the right to give that feedback. So that's the first thing. The second thing I would say is that there's so much advice, you know, you got to get a good website, you got to put your marketing out there, you got to get your show reel together, all this sort of stuff. And so much that I feel is premature, because you you're so desperate want to get out there and start earning fees, and so on. I think the most fundamental thing, by far is to create a product that people want to listen to, and gives them a reaction gives them an emotion that takes them on a journey. So it's finding audiences where you can go and craft, learn your craft and get better and better and better. And once you become good enough, then people will start referring you and you will start, you know, working your way up to the scale. So for me, it all starts with having a really good

Tom Bailey  17:22

product. Great. One, just follow up question for that you think it's really important that you find a line or a niche and stick to it when it comes to speaking?

Caspar Craven  17:32

The the it's really hard to, to know what that is off the bat. I mean that finding Product Market Fit isn't it has not done enough startups that you know, where you start off is not where he end up. So it's understanding where the market exists, and where that aligns with what is authentically, you're all about. And that will take some iteration to find that because the danger is you just go ahead and plunk yourself on a territory that somebody else is on, that may not be exactly the right fit. So it's a process of experimentation and iteration is the is the honest answer. It's taken. It's taken me quite a while to iterate forwards. And actually, I'm not a million miles off where I started. But I certainly got some really distinct themes that have come through the one there before.

Tom Bailey  18:23

Yeah, so don't try and nail it first time. Just get out there. Start speaking about what you're passionate about, or what you're an expert in, and you'll end up maybe somewhere slightly different at the end.

Caspar Craven  18:34

And also well, it's also trying to be in a market where there's demand as well, to get paid for it. Then it's identifying which audiences do you want to speak for? What are they care about? What are the issues for them? And there'll be some transitory issues, and then there'll be some evergreen issues into an evergreen issue. And then it's like a, what's my angle? What's my take on this? And finding that out? And you'll know, because you'll start getting the feedback and the reactions from that. So

Tom Bailey  19:03

yeah, perfect. Thank you so much. So, topical question. And you've already mentioned that you'll hone out a little virtual studio. So the 2019 global pandemic pretty much wiped out stage speaking. So how did you personally transition during this period?

Caspar Craven  19:20

I know what I was like, I I'm not sure I should say this, but I see it as an absolute gift. Yeah, that it felt like the world's just slid down, great, do some thinking, launched a new business and actually the kernel to other businesses as well. So I went into sort of hyper productive mode, on hassled by normal everyday life. I finished writing a book got that out there. And yeah, I just did an insane work. And that has been a real launchpad for massive acceleration. So yeah, it was a gift for me.

Tom Bailey  20:00

I love that. And, and clearly during that time you did build this home virtual studio that the light in the green screen the cameras. Do you think that virtual speaking is here to stay? Or is the world just quickly bounced back to big conferences and seminars?

Caspar Craven  20:17

That interestingly, I actually built the studio about a completed about two months before we


heard of COVID. So wow, he must have known is coming. But it's like, as long as there's some weird foresight,

Caspar Craven  20:27

but yeah, opposite thing to do is virtual history. Yeah, for sure. And it's like the why? Because it works. It's a different medium. And it's a different format. Yes, I mean, the all the live events I've been doing over the past month or two is amazing, getting people back in the room and the bus and all that sort of stuff. But now that people understand virtual is not going to go anywhere, because it's a really good cost effective way to get a group of people together. Now, it's not perfect and everything else, but it's part of the mix. So yeah, get used to it, it's gonna stick around as my view. So yep,

Tom Bailey  21:00

completely agree. Great. Well, thank you so much. We're coming towards the end. So I guess the last question from me a little bit of a curveball. What is the one question that you think I should have asked you today to also bring some great value to our audience?

Caspar Craven  21:16

What's the one question that you should have asked me? That is a curveball question, isn't it?

Tom Bailey  21:24

Stick within the topic of public speaking and, you know, advice that you may give. So

Caspar Craven  21:33

I'm veering towards something around. Who do I take advice from? Yeah. And who do I learn from? Because I think yeah, and maybe sort of Yeah, what am I sort of reading, studying learning at the moment? Perfect. Great. So yeah, so so so what am I reading, studying learning at the moment that I mean, my my business is called that big bold goals you can see. And so for me, I'm just fascinated by the massive shifts that are happening in the world right now. So I'm learning in an insane amount about genetics, about longevity, a little bit about defy and the things that are happening there. Clearly a good amount about climate change, because we all need that. So all the big trends and the things that are happening, because that will affect all of us, and it's hyper relevant to all of our clients. So if you don't understand what the issues your clients are facing, then you're not going to serve them very well. So yeah, stay all over the big big trends and things that are moving.

Tom Bailey  22:42

I love that yeah, great advice for anybody really looking to get into this world to stay stay on trend and stay topical with your content. So thank you so much. Again, last question for me is if people want to either book you as a speaker or find out more where can people connect with you online?

Caspar Craven  22:59

Yeah, thank you for the so Casper Cravens, CH SP AR Craven CRA V and I'm quite easy to find as any one of me. So my website Casper, or LinkedIn, I'm very active there. So there's two best places.

Tom Bailey  23:14

Excellent. What I'll do then is I'll pop those links in the show notes people can just click on them and they can come and find you online. So Casper, thank you so much again for your time today. I really appreciate you coming along and clearly sharing such great value with our audience.

Caspar Craven  23:27

Yeah, pleasure written I still T Vexilar questions