‘Failure can be quite a deceptive word… misadventures feels like a much more forgiving word that allows you to go off and try stuff.’
Gayle Mann and Lucy-Rose Walker have supported thousands of entrepreneurs in their work with Entrepreneurial Spark and beyond, and if there’s one thing they’ve learned it’s that the reality of being an entrepreneur is very different from the version portrayed on social media.
By encouraging entrepreneurs to share their misadventures and how they coped, they hope to end the conspiracy of silence: you’re not alone, and you will get through this.
They also learned a huge amount about writing a book and hosting a podcast along the way, which they share with hilarious frankness here!
Misadventures in Entrepreneuring site: https://www.misadventuresinentrepreneuring.com/
Gayle on Twitter: https://twitter.com/Gayle_Mann
Lucy-Rose on Twitter: https://twitter.com/LucyRoseW
Alison on Twitter: https://twitter.com/bookstothesky
The EBBC Summer Reading List 2020: https://www.goodreads.com/review/list/34626998-alison-jones?shelf=ebbc-summer-reading-list-2020
The Extraordinary Business Book Club on Facebook: https://www.facebook.com/groups/1447064765612358/
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Alison Jones: I’m here today with Gayle Mann and Lucy-Rose Walker who have been hooked on entrepreneuring their whole lives. They were both involved in the startup growth and eventual sale of Entrepreneurial Spark, a support system for entrepreneurs, and at its peak, they had 13 hubs across the UK helping over 600 entrepreneurs at any one time.
Gayle and Lucy-Rose have experienced plenty of their own misadventures along the way, as well as those of the 4,000 or so entrepreneurs that they worked with and they share their experiences in their new book, Misadventures in Entrepreneuring and also in their podcast of the same name. So welcome to the show at Gayle and Lucy-Rose.
Lucy-Rose Walker: Thank you. Great to be here.
Alison Jones: Yes, it’s really, really good to have you here. And I mean, misadventures, what a great word. Let’s talk about some entrepreneurial misadventures shall we, would you like to reveal all?
Lucy-Rose Walker: I know, that’s why you’re here. Like entrepreneurs anonymous, isn’t it? Yes.
Alison Jones: Where did that name come from first of all? I mean, what made you think: misadventures, that’s what it’s all about?
Lucy-Rose Walker: Well, I think, as an entrepreneur, we’ve been in the world of entrepreneuring probably for most of our careers now, There’s a sort of fear around failure. Like everyone talks about failure, fail fast, fail smart, fail cheap, you know, failure’s a badge of honor or being scared to fail, and ‘failure’ can be quite a deceptive word.
It comes with these connotations that, you know, if you fail you are by nature a failure. And we wanted to turn that around because entrepreneuring and the world of entrepreneuring is all about trying stuff and experimenting with stuff. And sometimes it works and sometimes it doesn’t and misadventures feels like a much more forgiving word. That allows you to go off and try stuff.
And if it doesn’t work well, you know, you can chalk it up to a misadventure rather than feeling like you did something really wrong.
Gayle Mann: Yes. It’s just a constant journey of misadventure of being an entrepreneur. There’s no kind of like you start and then you fail and you stop, it’s just this constant iteration. And we just felt like it was something that people weren’t talking about. and it wasn’t being discussed openly or widely in terms of these actual misadventures and making light of them and just helping people to understand that it’s okay not to be okay all the time.
Alison Jones: And why do you think we are, as entrepreneurs, so averse to, I don’t know, admitting to others and ourselves when it’s gone wrong? I mean, is it a sort of personal, you know, a shame-based thing or is it that you don’t want to be seen… that you think it’s going to impact on your bottom line? Because people don’t like being associated with failures, you know, just let’s unpack that a minute.
Lucy-Rose Walker: Yes. So it’s a mixture of all of those things. I think you go into often being an entrepreneur and you say, you know, maybe I’m going to leave a job or I’m going to start something new and people potentially are financially investing in you or you’re being supported by family and friends. and, you’re kind of like, right, I’m all in, here I go.
And if it maybe doesn’t go to plan, there is that kind of, it’s a bit embarrassing to say maybe it hasn’t gone to plan. or you don’t want to kind of explain to people that actually I don’t really have a clue what I’m doing. And sometimes people don’t have the support of family and friends, which makes it even more difficult.
And there’s kind of a, I need to make this work. so I think it’s just something that people often don’t want to talk about.
Gayle Mann: I think just on that point, where Lucy was just talking about family and friends or supportors, you’re often as an entrepreneur quite dependent upon the support, either emotionally or financially, of other people for certain periods of time and it’s really hard to, let’s say, go home at night to your husband or wife or other half and say , I don’t really know what I’m doing. I don’t know how I’m going to make the mortgage this month, or to say to your investor, well, you know, I’m kinda winging it.
There’s not very many people that you can talk to and actually explain how you’re feeling.
And one thing thing we found, we’ve got the book, we’ve also got the podcast and we interviewed over 50 entrepreneurs. And for some of them, it was almost like the first time they could actually have a safe space to tell their story.
And nine times out of 10, at the end of the interviews, they would say, Cor that was really cathartic.
Alison Jones: Yes. And I can imagine that as you say, when you articulate something, you put a story around it, you understand it yourself sometimes. So even just that process is powerful. So there’s the kind of catharsis and the sort of, you know, narrative, making sense of it and stuff. But I’m really interested as well – I know you worked with so many entrepreneurs over the years. What are the benefits of allowing that kind of safe space, of actually sharing those misadventures for other people, as well as that entrepreneur?
Lucy-Rose Walker: Oh, yes. I mean that in itself is the most powerful and I think it’s greatly identified, it’s definitely the two parts of that. So it’s about opening up and saying those things, as Gayle said, out loud for you, sometimes for the first time and not being embarrassed or ashamed, or worried about what people will think, but just saying, do you know what, I’m a bit scared about this, or I’m not really sure what I’m doing here.
And as an entrepreneur, it can be so lonely because you don’t necessarily want to share that with your team or your investors, or give anybody the impression that, you know, maybe you’re not quite sure what next move to make or what to do. So that, creating that safe space for people, has just we found been so powerful, to allow them to just voice that and find others who are saying the same, which is the second part, is being able to help other people. So just listening and thinking, Oh, that totally resonates with me or I remember when that happened to me. And I’m not the only one.
Gayle Mann: Well, that’s it, the ‘I’m not the only one’ is the real sort of eye-opener, yes.
Alison Jones: And that could mean all the difference, couldn’t it? Because you could be just sitting, thinking I’m a failure. I’m not cut out for this, this is, you know, if it’s hard, I must be doing something wrong because everybody else is having such a great time.
Lucy-Rose Walker: Yes. And I think, you know, one of my favorite phrases from the podcast is, an entrepreneur we spoke to and it was about the perception versus reality of being an entrepreneur. And she said my friends said to me, they say, ‘You’re doing so well on LinkedIn.’ It’s like, well, yes, of course I’m doing well on LinkedIn because that’s the image that I project. But actually what’s going on underneath is a whole different ballgame. And I ain’t ever going to share that publicly on LinkedIn or any social media platform.
Alison Jones: It’s true. And we forget that and we know it about ourselves, but we forget that that’s also the case for everybody else.
Lucy-Rose Walker: Yes. Yes. So you think everybody’s doing really well, because that’s the image they put out there.
Gayle Mann: There’s also another part to this, which is most people, particularly if you’re a first time entrepreneur, you come to running your own business having either worked in another business or you’ve worked with other people and then you find yourself on day one or day two or day 101 having to make decisions all on your own and the mental energy that that uses up is immense. And it’s really easy to underestimate that. Particularly, Lucy-Rose and I, we worked together and we work very well together. We make decisions very quickly together, but whenever one of us is left to our own devices to make a decision, it’s hugely draining.
So just having someone else and another voice, to talk things through with can be so clarifying and, yes, you know, make you feel that aloneness goes away very quickly.
Alison Jones: Yes. And now I’m jealous, you see. So I want somebody to be able to have that kind of conversation with when I have to make decisions. Tell me a bit more about the way you work together, because you are together, you know, phenomenal, and you do the podcast together and you run your business together and you’ve written the book together.
What was that like? Did you ever at any point hold each other on the floor by the throat?
Gayle Mann: Yes. Sometimes
Alison Jones: Okay.
Lucy-Rose Walker: We’re not going to shy away from those Misadventures.
Gayle Mann: So Lucy-Rose can tell you about her famous check-in.
Lucy-Rose Walker: Yeah. So I suppose I’m a big believer in checking in and, you know, doing that in any relationship. So always kind of, you know, having a moment when it’s like, how are you doing, how am I doing? And just kind of, how is this working?
But it’s one of those things that I like to talk about a lot and share with people. Cause I do it personally as well, but sometimes you get out of the habit of doing it. And I think for Gayle and I, probably over the last couple of years, particularly in our new business, had got out of the habit of doing that. And we know as soon as that happens, you can see the challenges coming to the fore and we kind of tip-toe around it. And you know, there’s an elephant in the room, but nobody’s talking about it. And somebody just has to be like, what’s going on?
Gayle Mann: And I suppose we’re very clear on each other’s strengths and weaknesses and, Lucy-Rose is very much a progress, progress, progress, hurry up, hurry up, hurry up, let’s get things done, and I’m very much a slow and steady wins the race type person. So I’m very cautious and I like to just meticulously work. I’m also a bit of a, well, we’re also perfectionists, but in different ways. And so when we’re working well together, we work really well together. But when we’re frustrated with each other, we get very frustrated with one another. So the Check In, when we remember to do it, and we remember to be really honest with one another, is it a really good process for us to make sure, to get us back on track. But if we don’t do regularly then we can drift and that’s what a lot of people do now.
Alison Jones: That’s so interesting, and that goes across every dimension of your relationship, which as I say is so multifaceted, but in terms of the writing particularly, how did you kind of divide that work between you and agree the structure and just, you know, check in on each other’s stuff.
Gayle Mann: Well, that one was a much easier one I think, because the book was my idea and Lucy-Rose had no interest whatsoever in writing a book so.
Alison Jones: That simplify things, doesn’t it?
Gayle Mann: Yeah. So I said, you know, God, there’s so much stuff here that I wish people had told us and I feel like I’ve got something in me that I need to get out. It was like I had to exorcise it in some way. And writing felt like the right way to do it. So. Lucy-Rose pretty much said, well, you fill your boots. So I did. I just splattered some stuff on a page, which is the only thing I knew how to do, because I’ve never written a book before. I’d never written anything more than a blog post or a management report before.
And I was in quite an emotional place, so it all came out as like one big cathartic sort of stream of consciousness and then I would give the stream of consciousness to Lucy-Rose and she would very kindly structure it for me in a way that it made a lot more sense. And we just went back and forth like that for about 18 months until we had something that was actually helpful.
Lucy-Rose Walker: It’s worth pointing at that point, particularly for people who do go into writing books together, is being really conscious, if you’re not the person actually doing the writing, of how the other person has… the emotional, words that they have put on paper and energy that they have put into that and how you have to be so careful in how you deliver any critique on that.
I think that’s really worth bearing in mind because when you’re, although it’s about us and the entrepreneurs that we worked with, I was not as emotionally involved in the creation and particularly at that stage. And recognizing that it’s very much a process that somebody is going through and for Gayle, like she said, she was quite emotional herself. So you’ve got to be really aware of that and tread very carefully and make, I had to be really clear of when was the right time to deliver anything to her.
Gayle Mann: And I had to be really clear about when was the right time to deliver anything to me. Because at the same time it was the very, the first iteration was hugely personal.
And having never written anything before I had vulnerabilities around both my writing and the story itself. So you’re sort of reliving all your misadventures and reliving all of the times that you didn’t quite get it right. And you could have made different decisions. And you’re also thinking about, well, whether or not your writing is any good? And is this something people will want to read? And so it’s a huge help to have someone, to be able to give that kind of constructive feedback, beside you, but also to understand who you are as a person and the time and the place for that. Yeah.
Alison Jones: Do you know, I hadn’t kind of fully taken that on board, actually that writing a book anyway is hugely vulnerable making. But when you’re writing a book for the first time about misadventures and something that is so personal, it’s about making yourself vulnerable as an entrepreneur, that’s just mind blowing, isn’t it, the level of vulnerability that’s going on there.
Gayle Mann: It really is, like, because you know, you find yourself, although what you want to do is share the misadventures to help other people in the future. You do find yourself thinking, Oh wait a minute. should I really say that I did this or should I really be honest about this? And that’s the whole point.
So we were, but you do question that cause it’s like, okay, I’m opening myself up here and that’s scary. Yes.
Alison Jones: And it’s such a permanent record, isn’t it? Because the other thing of course, and what I want to talk about is the podcast as well, but, when you were writing, did you have a sense of legacy? If that’s not too grand a word.
Lucy-Rose Walker: I think we had a sense of, for me, it’s always felt like a duty of care. so we’ve worked, you know, our legacy is our Entrepreneurial Spark business that we’ve worked with over 4,000 entrepreneurs and helped them to develop the right mindset and behaviour, and overcome these misadventures by breaking bad habits and learning new ones.
And that is our legacy, but along the way we were growing as entrepreneurs at the same time. And when you get to the end of that, and you think, do you know what, I’ve only just started my journey here, and there are so many things that despite working with 4,000 entrepreneurs, despite growing and scaling our own business, we are supposed to be the experts, but there were all of these elements that came out of the blue for us, that nobody tells you. And it felt like a duty of care. So not so much a legacy, but…
Gayle Mann: Oh, yeah,totally. I would build on that by saying, I think, and this is particularly important right now is it’s almost like we wanted to tell people what it was really like being an entrepreneur.
We’ve seen so many people who’ve run headlong into it, who have sacrificed and who have maybe risked quite a lot to run their own business only to realize actually it really wasn’t for them. Or it just wasn’t something that they wanted to do. And I think before you go into it, it’s really better to know exactly what it’s going to be like and what it feels like.
Not just like, yes, can you do a cashflow and can you write a business plan, but how am I going to feel every day running this business on my own? And we wanted really to make sure that people took that step before they jumped into being entrepreneurs. and we felt like that was really important.
Alison Jones: Yes.
Gayle Mann: You go on social media these days, then the perception of the life that you’re going to live as an entrepreneur is very different to the life that you actually live and that’s one of the, particularly the big myths that we wanted to bust.
Alison Jones: Yeah, it’s so true. Isn’t it. And then you obviously launched the podcast as well, Misadventures in Entrepreneuring, alongside the book. I know it came sort of slightly afterwards, but no, hang on a minute. No, have I got my timing wrong? When did… well, you tell me how did the two relate.
Lucy-Rose Walker: That was a whole misadventure in itself. Because we did all these interviews when we came out, when we sold the business and came out and decided to write the book. So we wanted to do interviews so we had stories to put into the book. So we ended up just recording them all. So we found ourselves sitting with 40 to 50 interviews with entrepreneurs that we had recorded and we thought, well, wouldn’t it be great to make a podcast, but that phrase in itself is almost like saying, wouldn’t it be great to start a business exactly…
Alison Jones: How hard can it be?
Lucy-Rose Walker: We were writing a book in the background and we could just take these recordings and make them into a podcast. But actually we wanted to make curated podcasts. So we were taking bits of each of the interviews and weaving it all together. So we think they’re good. And they’ve been called the Survival Bible from a number of entrepreneurs.
So hopefully they’re helpful, but that was tough. Really tough learning that new skill.
Alison Jones: Yeah. And what did you enjoy about podcasting or are you just never going to touch it again with a barge pole?
Gayle Mann: Yeah, we’re going to do that one. We’re going to chuck it in the misadventures bucket. I think.
Lucy-Rose Walker: We love it. And we love the interviews. It was amazing. I mean, we are curious people. We love to ask questions. We, our nature is to enable entrepreneurs, so we’ll dig deep and poke about in the bits that people don’t want to talk about and make them slightly uncomfortable, but in a positive way. So that is just something we love doing and helping people to kind of have those conversations that we talked about in a safe space, so that bit we will always love .The production, not so much.
Alison Jones: Not so much. Yeah, no, I hear you.
Gayle Mann: Yeah. Yeah. It’s not something that really comes particularly easily to us. And if we’ve learned one thing, it’s you know, you can stick at stuff for so long, but if you’re not enjoying it, then move on to the next thing. And that’s definitely one thing that we have, we haven’t enjoyed the production side of it.
We’ve really enjoyed what we’ve created. And so we’re just gonna, we’ve created 12 episodes and they’re evergreen content. And if you talk about a legacy that 12 will be it. I like the podcast. Yes.
Alison Jones: Now I always ask people about their best tip for a first time business book author. I’m going to also be greedy and ask you for your first tip for a new or potential podcaster. So this is going to scale everything up massively. So for each of you, what’s your best tip for a new author and a new podcaster.
Gayle Mann: So I’ll take the author one, at the moment for me, so Alison, I listen to your podcast, so of course I listened to get all my tips. I listened to everyone talking about how they have plans and structures and discipline and all of these things. And I had none of that. And what I would like any potential first time authors to know that yes, for those that work that way, that is definitely a good way to do it.
For those that don’t work that way, it’s also okay to do it your own way. It’s not a linear thing, I didn’t sit down and write 501 or 499 words every single day. Some days I did and in the end in the last week, I probably wrote more words than I had written in the previous 18 months.
Alison Jones: The power of the deadline.
Gayle Mann: Correct, but it’s not a linear process. And I think that is important to recognize. And I also wrote three versions of the book before I got to one that was helpful.
Alison Jones: And it’s again, you see you listen to people and they say, Oh no, I loved doing the book. And it just flowed. And that’s really dispiriting if you are in the trenches and it isn’t going well, and you don’t find that the structure thing is helpful. So, you know, it’s just like being an entrepreneur, isn’t it hearing somebody say, Oh, it was really hard doing that, you know, I just had to get my own way. It’s helpful.
Gayle Mann: Yeah, you know. I still loved it, I still loved learning to write and learning how to construct a book and it took me longer, but I enjoyed that process and I don’t mind that it took me three versions because now I know how to do it. And now after ‘Oh My God I’m never going to do that again’, now I’m sitting back here and I’m thinking, well, I wonder when I might write the next one.
Alison Jones: It’s like running a marathon, isn’t it. You finish and you’re like, never again. And by the time you’ve drunk your first energy drink, you’re thinking, you know, I reckon if I did the split in the middle differently, I could make an improvement in my time there…
Gayle Mann: But you know what? I still don’t think I would follow the same sort of military, structured process. I think it would still be, I would write from the heart. And so your heart has to be in the right place in order to get the words out.
Alison Jones: But you trust yourself more now in the process because you’ve done it before, haven’t you?
Gayle Mann: Yes, definitely. I still think it’s a really vulnerable exercise, so whilst I would trust myself more, I wouldn’t have all of the anxiety around, do people want to read this,
Alison Jones: Yeah, honestly, sorry, I think you probably would. So Lucy-Rose, I’m not going to ask you for the writing tip. No, I won’t go there, but you’ve given us a tip on giving feedback. That was really useful. Thank you. Either of you got any thoughts on the podcasting tips?
Lucy-Rose Walker: I think, so for me, and this probably comes from the production of one and listening to podcasts, it’s the consistency. So having a format that you stick to, that people are expecting week in, week out, I think, is probably one for me that is a good rhythm to get into. So, you know, kind of what you’re doing and the way in which you’re doing it.
And then the sort of questions that you’re asking. Cause I think there’s so many out there right now and it’s about trying not to overcomplicate it. So know your niche and just do it really well. And stick to it
Alison Jones: Yes, I think that’s great advice. Yes.
Gayle Mann: Just a quick one for me. if you’re doing a podcast for your business, make sure that it delivers value back into your business. it takes time to do, it’ll take time away from the commercial side of your business. So make sure there’s some sort of value in there. Yes. Or understand the difference between something that you want to do for a hobby as a nice to have, and something’s going to deliver the value back to your business. That would be my advice.
Alison Jones: Absolutely, and do you know what? That goes for podcast and books, doesn’t it?
Gayle Mann: Yes. Very true. I learned it from you, Alison.
Alison Jones: Well, very wise, very wise.
Would you both, I mean, obviously every entrepreneur honestly should read Misadventures in Entrepreneuring because it will not only make you feel better about stuff but it will also give you really, really practical, ideas for getting yourself unstuck which is great. But, any thoughts on business books that you would you know, inheritance business books that you would recommend to other people as well?
Lucy-Rose Walker: So mine probably doesn’t actually go strictly down the business book route. but it comes back to what I talked about before in terms of checking in and communication. And the book that I quote quite a lot is Option B by Adam Grant and Sheryl Sandberg.
Alison Jones: Oh, brilliant. I’m just reading Adam Grant at the moment actually, Give and Take, I love his style.
Lucy-Rose Walker: Yeah, I really liked the way they wrote this book together. And I just loved the, we actually had it in our wedding vows, but I know it was, for me, the big thing was the fact that there’s three parties in a relationship. So there’s the two people and then there’s the relationship itself. And the fact that that actually needs to be protected and nurtured.
And for me, that carries across every relationship you have in your life through professional and personal. So I just think that’s a really important one to think about.
Alison Jones: That’s really profound. Thank you.
Gayle Mann: Yes. I certainly, when Lucy-Rose talks to me about that, you know, it’s a real eyeopener, which probably carries through to my, business book recommendation, which is Gary Keller’s. The ONE Thing.
Alison Jones: Yes. You’re not the first person to have recommended this actually Gayle but, it’s a great one, isn’t it?
Gayle Mann: Yes, well, it’s the only other one that I tell people about. And it’s the one that helps me pretty much every single day. If I am feeling stuck or confused or I need to overcome an obstacle or I need to patch up a relationship, then I only have to think what’s the one thing that I can do today that will make everything else either easier or unnecessary.
And perhaps that is, I have to nurture that relationship or I have to work with the team more, you know? And so that’s been really quite profound for me.
Alison Jones: It’s funny, personally, I read that and was really unimpressed by it and was how I don’t really get on with the one thing. And then enough people said, Oh, you know, it’s changed my life that I thought, Oh, okay, I’ll reread it. And I reread it and thought, this is brilliant. What was I thinking? So if you, I don’t quite know what happens; sometimes it’s just not the right time for you for a book, or you go in with an assumption or a chip on your shoulder about how it’s all right for men to focus on one thing, I’ve got to run a house and a business, you know, and sometimes you go back and it’s, you know, they say you can never stand in the same river twice, you never quite read the same book twice because you’re a different person reading it. It’s really interesting.
Gayle Mann: Really true. Yeah. What I like about it is it forces you to stop for a minute and actually think, and…
Alison Jones: Maybe that’s what I hated about it.
Gayle Mann: I hate it too, because I don’t like to stop and actually reflect. And the question that Lucy-Rose asks me so often and I absolutely hate is what if you just stopped. And you know, The One Thing forces, I think, forces you to do that as well. And so it can be quite an uncomfortable place. That’s what makes it good, right?
Alison Jones: It is. And it also completely explains my initial reaction to it. Yes. I feel like I just had a slight therapy session here. Thank you. Brilliant. Thank you so much for your time today. It has been absolutely great talking to you and just, you know, brilliant is going to unpack a bit more of why you do what you do and why it matters, which, you know, it’s just so powerful.
I think what you’re, the service that you’re doing for entrepreneurs is brilliant. If people want to find out more about you and more about the book and the podcast, indeed, where should they go?
Gayle Mann: It’s a bit of a tongue twister, but, misadventuresinentrepreneuring.com is our website. We’re also individually on LinkedIn. EntrepreneuringMisadventures on Instagram, Twitter, and Facebook as well.
Alison Jones: There’s a lot of different ways that people can get in touch, I will capture the main ones and put those on the show notes at extraordinarybusinessbooks.com Brilliant, but actually misadventures and entrepreneuring are such distinctive words that, you know, if you’ve got access to Google, you know, it’s not going to be hard to find you, which is a lesson of its own when it comes to writing a book, isn’t it.
Gayle Mann: Very true actually. Yeah. And I don’t know if you remember, but it was all of the post-it notes on the table that day, when we had our session in London together that we came up with that word.
Alison Jones: I will never forget it. Yes, it was brilliant. And it was a real kind of shift in energy. Ooh, that’s nice. We like that word. Brilliant. Yes. Wonderful to have been part of that in a little way. Thank you so much for your time today.
Gayle Mann: Thank you so much Alison, Can I just say it’s been an absolute pleasure working with Practical Inspiration to bring this book to life. It’s been really wonderful expedience
Alison Jones: Aah wonderful, thank you. Well, the feeling’s mutual.
Gayle Mann: Thank you so much.