Episode 274 – Breaking rules with Jackie Fast

‘You don’t have to have everything figured out when you sit down at your computer…. just start writing.’

Jackie FastJackie Fast sees writing a book just like entrepreneurship – don’t let fear stop you, break some rules, figure it out as you go along. And in Rule Breaker: Rebellious leadership for the future of work, she proves that that’s the secret of success in the 21st century – the old playbook that so many of us have internalised just doesn’t apply any more.

This is a fascinating reflection on her own remarkable journey from broke founder to MD of one of the world’s most successful sponsorship companies, and how the process of writing a book mirrored that exercise in courage, exploration and action-taking.

Jackie’s site: https://jackiefast.com/

Jackie on Twitter: https://twitter.com/JackieFast

Alison on Twitter: https://twitter.com/bookstothesky

The Extraordinary Business Book Club on Facebook: https://www.facebook.com/groups/1447064765612358/

The Extraordinary Business Book Club bookshop: https://uk.bookshop.org/shop/extraordinarybusinessbooks


Alison Jones: I’m here today with Jackie Fast, who is an award-winning entrepreneur and business leader, the founder and former Managing Director of one of the most successful global sponsorship companies. She’s worked with some of the world’s biggest brands, including the Rolling Stones. Formula 1, Virgin, Allianz and Shell.

She’s an in-demand business and entrepreneurship public speaker. She’s featured in Forbes, Metro, Business Leader Magazine, Money Observer and the Telegraph, and her new book is called Rule Breaker: Rebellious leadership for the future of work. So welcome to the show, Jackie.

Jackie Fast: Thank you so much for having me.

Alison Jones: You’re very welcome, that’s a cracking title that isn’t it, it’s very rousing. You can’t say it and not feel a little bit ‘hairs on the back of the neck going up’.

Jackie Fast: Oh, wait until you read the book, you’re in for a real treat. Yeah.

Alison Jones: Well that’s quite important because when you have a title like that, you’re kind of making a promise to the reader and you’ve got to deliver on Yeah. it, haven’t you?.

Jackie Fast: Absolutely. And I mean, I think, I mean, I know it does, so at least I’m glad that the title makes you interested.

Alison Jones: Well, and it all comes from you doesn’t it, from your own business journey. So I thought it would be really interesting just to start with that because a lot of people won’t know your story. Just tell us a little bit about, how it started and that whole kind of journey that you’ve been through to today.

Jackie Fast: Of course – so much like everybody else, I grew up in Canada, kind of suburbs. So, you know, go to school, get a job, get a nine to five, all of that great stuff that your parents tell you, your teachers tell you and everything.

And I had a slight departure, I graduated university and I just didn’t feel like I was on the right path. And I ended up very, I suppose to say stupidly, but truthfully it was very drunkenly, buying the cheapest airplane ticket I could get to an English-speaking country, which happened to be London. And I had never been to Europe before. I’d never been to London before. I didn’t know anybody before.

And so I arrived and discovered I loved it. And kind of along the way and deciding to launch my business mostly because I was forced to, because I got overlooked for a job because somebody said I didn’t have enough experience. I mean I can go into more detail about that, it’s not the point really.

And I set up my first business really petrified. And I kinda did it out of necessity because I needed a visa to stay in the country and it went against the grain of everything I had been told since I was a child about what one needed to do to be successful.

So there I was, 25 years old with a laptop, like very little money in my bank account. And I set up this business called Slingshot Sponsorship. Fast forward to four years on and I had four global offices, Brazil, Oslo, Singapore and London, working with all of those people that you just said. And I mean, it was insane really.

I was on a long-haul flight, like once a week managing some of the world’s biggest clients. And it really, I mean, in a way I thought, maybe my path was a bit of an outlier path, but along the way, I worked with some of the most successful people in the world.

And I just really found a common thread in that the people that were really, really successful, really didn’t play by the rules. And so this book means a lot to me because it is my ethos. And I have gone around, especially with my story, talking to a lot of people, trying to have a better career, trying to start a new business, et cetera.

And a lot of it is, I find that the reason they’re stuck is because they replay the same stuff in their head that they’ve been told and it just doesn’t work anymore. And you know, nobody has really written a book for leaders of the future with this in mind. All of the books are written by, I hate to say it, but the pale stale male that had careers in the seventies, like, well before the internet, well before social media and the world is just different and nobody is writing books about how people become successful now. Until now, basically.

Alison Jones: I’m really fascinated by that point you make about how the successful people break the rules, because I think that ties to something really deep. It was interesting that you, having had that upbringing, having absorbed all those rules about how you’re supposed to do it, something very strong in your head about compliance, about being rewarded for being good, about you know, staying in the lines: what’s the shift that you have to go through to enable you to break rules creatively and be successful?

Jackie Fast: I just think more people need to talk about it as a positive thing. I think, you know, when you talk about rule-breaking, it’s so negative, like, oh, I couldn’t be a rule breaker because I don’t want to go against, against, not against the norm, but you know, I don’t want to be negative or I don’t want to do anything negative. And it seems very like us and them.

Like, it couldn’t be me that would be a rebellious person. I’m not a rebellious person, I don’t speak up. But actually, you know, the book is called Rule Breaker: Rebellious leadership for the future of work. But when you really dive into the book, there’s simple things like do work that you love to do, like follow your passion. Like that’s not a rebel thing, that’s not being rebellious, but in today’s society it is, because we’re taught to become a doctor, a lawyer, an accountant, a teacher, or a nurse, you know, nobody’s telling people to go out and be like a sponsorship expert or any of that stuff.

And so following what it is, if you like gardening, go out be a gardening expert. Like nobody is following their passion. So in a sense, yes, that is breaking the rules of what we’re kind of told, but is it really rule breaking in that sense? I don’t think it is.

Alison Jones: Well, it’s certainly not law breaking and it’s quite an important distinction, isn’t it?

Jackie Fast: Absolutely. Yes. I’m not saying go storm the White House. This is not the book for you.

Alison Jones: Yes, there are other presidents you can listen to about that. And I wanted to talk to you about the writing of the book as well, because obviously on this show we’re very interested in how people write their books from every stage from just having the idea and the motivation, to organizing your thoughts and then the whole publishing process.

So just talk me through that a little bit. What surprised you about writing the book and what did you discover about yourself in the process?

Jackie Fast: Well, this is the second book that I’ve written. And the first book I wrote, it came out in 2018, that was purely about sponsorship sales. So it’s called Pinpoint. And it was, the reason I did that was, I sold my business in 2016 and I wanted to kind of, not leave a legacy, but I just felt that all of the things that we were helping clients do were so easy. And nobody had really written this stuff down.

So I wanted to write a book that kind of explained kind of a how to, of how to go out and secure a sponsorship. And it was so easy for me to write that book because I’d been talking about it for six years. The format was basically every workshop that I had ever run.

All the case studies I’d built up in those six years, talking about all the stories on stage through keynote presentations. And I found that that book just kind of fell out of me. With very, very minimal thinking, I’ll be honest with you, mostly because I spent six years thinking about it.

Alison Jones: Yes, it’s not that it was minimal thinking. It’s just that you’d already done it.

Jackie Fast: I’d already done it. This book was totally different. This book, I was approached to write a book about whatever I felt was important. And I had to do a bit of soul searching to figure out what I thought was important. And then I kind of landed on this topic, this ethos about rulebreakers and being successful and communicating why it’s important to be a rule breaker now.

But then I had to do a lot of work. So a lot of things that I thought about, I knew instinctively, but I didn’t always know exactly where it came from. And so I did lots and lots of interviews with a lot of the people that started Silicon Valley, did lots of research from like videos, I interviewed a ton of people. And I talked about everything from why social media is so addictive and why that’s a negative thing with meaningful relationships and connections and why meaningful connections are important for the future of work.

And I mean, the book really takes the gambit of how the internet started in the sixties with Stewart Brand, all the way to the present day, where we’ve got Bitcoin and the gig economy.

So that was crazy. That was just a lot of research. Now I thoroughly enjoyed that part of it. I’ll be honest with you. That was really great. And then the writing of the book I struggled with more than I thought I would, but I was also six months pregnant at the time with my first baby and I hadn’t appreciated how hard being pregnant would be.

So that was challenging as well. But I mean, I was and am inspired by this topic. And so that really propelled me to make it good.

Alison Jones: It’s so interesting that you were approached to write the book about whatever you found interesting, which is of course not most people’s experience. And it sounds, it sounds like a dream, doesn’t it, but actually that’s really tough because most of us perform best or certainly easiest when there’s a constraint, you know, when somebody is telling you we need this and then you can do it. Actually, that kind of open brief, that’s really hard.

Jackie Fast: Yeah, I mean, it definitely was difficult. Yeah. I mean, absolutely it was difficult. It took me a really long time to really nail what it is that I wanted to talk about. And also not just that, I mean, I could talk to anybody for like a really long time about anything, but you know, what I could talk about that would be valuable for somebody else.

 And I think like you, you know, obviously you run a podcast, but there are so many business books out there. And I am not somebody who likes to take up people’s space or time with fodder really. You know, if I’m going to write something, I want it to be good. So it took a really long time to figure out what that would be

Alison Jones: And did that emerge as you had those conversations? Was it something that kind of crystallized? Can you remember the moment when you went that’s it, it’s about rule-breaking and leadership.

Jackie Fast: I don’t even think it was called Rule Breaker until I started writing. I don’t think I had a title until I was at least three chapters in. I had a concept for what I wanted to talk about. And I obviously had to pitch to the publisher about my idea and why I thought it was important. But I don’t think we had a title for a couple months.

Alison Jones: It’s funny how the process of writing helps you get clear on this stuff, isn’t it? Sometimes people think you have to be completely clear before you start, but actually you do the work and that is what clarifies your thinking.

Jackie Fast: Completely. And I mean, I was very clear at the start who I wanted to talk to, so that was helpful. So there are people along my journey who I have been inspired by, who I think have really unique perspectives on the world, who are doing things differently, who are disruptive. And so I was really clear, these are the people I want to talk about.

And then it kind of evolved, the whole rule breaker thing was the theme that ties the book together. But quite frankly, that’s what ties me to them. That’s what’s interesting for me because I see what I’ve done and how I work in the way that they do. And so that’s kind of the point really.

Alison Jones: And that writing of the book enables you to reach out to people, doesn’t it? Gives you a, I was going to say a pretext, I don’t quite mean that, but it gives you a reason to have those conversations, which is such a privilege, such a joy.

Jackie Fast: Well, most of them I know so that was helpful. So the people that I interviewed are like ex-clients or people that I’ve worked with or known for a while. But I hadn’t ever talked to them about this kind of stuff before because they’re clients, right? And most of the time people ask my advice, I don’t usually ask people why they do what they do.

So one of them Bill Tai who is, you know, literally has been quoted as the best venture capitalist to ever set foot on the planet. He was the first person to invest in Twitter. He’s the first person to invest in Zoom. He’s amazing. He’s been a client of mine for over 10 years. We have such a great relationship.

But I have never ever asked him about venture capital stuff, because I mean up until recently, I never did venture capital stuff. So for me to sit down with somebody I’ve known for over a decade and have like a totally different conversation about the future of business, what he looks for in leaders, how the world is changing and his perspective of it I found was so insightful.

Alison Jones: Yeah, I can imagine. And then when you’ve got all that great content and you’ve had those conversations, which were, I’m imagining quite open because you didn’t have a really clear agenda at that point, it was much more exploratory: how do you manage that material? Because I think this is something that everybody listening comes up against.

You know, you do the research, get the stuff and then you’ve got to write the book. And just how did you process all that material that you had into a digestible book?

Jackie Fast: Well, I’m very pen to paper. So I literally wrote out my chapters on a big piece of paper, chapter one, these are my key points. And then I went through all the transcripts of my interviews and my notes and then I would go put sticky notes of like key things like, oh, this guy should go here and this is why.

And then I’d move the sticky notes around. But on my journey I would read articles and blogs and then I would cut quotes and other stuff and then I’d attach that to the chapter that I thought it was relevant. So when it came time to writing the book every chapter had a bunch of material that I would then go through and then start literally, this is the point for this part.

And I would kind of like structure it that way. And then I would start writing.

Alison Jones: Yeah. And it worked? Or did you adapt it as you went?

Jackie Fast: Nope, that’s how I did it. I mean granted, the first three chapters were like really detailed and I think when I initially talked to the publisher about chapter six and chapter seven, they were very much like, I think I’ll talk about this here. And when I went down to it, I was like I have nothing to say.

And, a thousand words that I have no idea what I was talking about. So yeah, that happened on two chapters for sure. But I mean, the method I thought worked, I mean it got there in the end.

Alison Jones: Absolutely, and it’s so fascinating isn’t it, because it’s quite emergent how you do this. What would you do differently next time? Because you know there’s going to be a next time, right?

Jackie Fast: Yeah, no, a hundred percent. This is hopefully one book of many. The whole idea for me is I like to do things. This is the first time I’ve ever written and this book is, for me, it was huge. It was 65,000 words. My first book was 21,000 words.

It was completely all new material whereas my first book was just regurgitating stuff I’ve been talking about for years. This was a huge achievement for me, but now that I’ve kind of gone through the process, really, I want to do it again because I feel like I learned so much and I am very proud of this book as well.

 Things I would probably change moving forward? Nothing. I don’t think… I really think it worked. I think I wouldn’t do it while I was pregnant again. I think tip number one.

Alison Jones: Well, it’s funny you should say that. I was just thinking, when you said about, you know, I’ve learned so much, I have to do it again. I remember saying that to my husband after we’d had one child and kind of come through, you know, the first year, I said we kind of have to do this again, because otherwise everything we’ve just learned is such a waste, you know?

Jackie Fast: Totally. No, I know we’ve always talked about that with our children. Like the first one is just like a guinea pig and we’ll see what works. And the second one, the second one’s going to go to college for sure.

Alison Jones: Time will tell

Jackie Fast: Okay.

Alison Jones: If there’s someone listening who is still grappling with their idea and hasn’t got to that point of clarity or hasn’t nailed their systems yet. I always ask my guests, is there a one top tip that you would give them? What would be your best piece of advice for somebody listening?

Jackie Fast: I think just start writing. I think like I wouldn’t get so bogged down with Oh, I don’t have the chapter three figured out yet, or, I don’t really know the point of it. Quite frankly, I mean, the conclusion of my book, I literally wrote probably a week before it was due to be submitted. And I had no idea how I was going to conclude it at all, but it evolves like most things and also the, the process of writing takes so long, you should hopefully evolve with it.

 I wrote mine in the middle of the pandemic and when I started writing it there was no pandemic, by the end of it everybody is in lockdown and mine is all about the future. So I had to go back, so many times, on many edits, even after I’d submitted the book to the publisher, to update it and change it and change perspective as well.

And that’s a good thing. Like that’s the point of a book, right? It should be a timestamp, a timestamp in the moment. So you don’t have to have everything figured out when you sit down at your computer. So just start writing would be my tip.

Alison Jones: Yeah. And it goes back to that point that the writing itself is what gives you the clarity, isn’t it? You can’t just sort of think yourself into writing it.

I’m just wondering actually, how does the rule breaking thing apply to writing a book? Is there a parallel there?

Jackie Fast: I mean, I definitely rule broke, I mean, I didn’t know the rules to writing a book in all fairness. I didn’t ask a lot of people. I just kind of went and did it, but I definitely think not having a plan for a good chunk of the book before you sit down to write it is definitely, I wouldn’t have thought that was a good thing to do

Alison Jones: It’s not textbook. I’m going to be honest with you. It’s not textbook. No.

Jackie Fast: But chapter five and six. I think it’s five, six and seven, I did not really have a plan. And I had a couple of sentences and I thought I would just wing it. And I don’t know. I mean, it was actually, it’s a good part of the book.

Somebody said that that was one of their favorite parts of the books. And I didn’t expect that. And again, I didn’t have a conclusion. I had no idea how I was going to conclude it and I kind of made that happen, but you figure it out as you go along.

Alison Jones: Well, I mean, exactly like entrepreneurship, right?

Jackie Fast: Yeah, completely. Completely. Yeah. And I just think, too many people are too afraid to do stuff, and this is the whole point about Rule Breaker, they’re too afraid to quit their job and try something new. They’re too afraid to ask their boss for a raise, they’re too afraid to write a book because what if they don’t know everything that they need to put into it?

I think we need to stop being too afraid, really and you know, break some of the rules so you can move forward.

Alison Jones: And actually writing a book is quite a low stakes way to do that, isn’t it? So it’s not so much at stake. Yeah.

 Do you have a favourite book as well, Jackie, that you’d recommend to people? Well, I mean, obviously yours obviously, but you know, apart from that?

Jackie Fast: No, I definitely would recommend Be More Pirate by Sam Conniff. So Sam actually endorsed my book, but that book I find is really great and definitely should be a precursor to my book. But I mean, even if you don’t read my book, you should read Be More Pirate. It’s exactly the kind of ethos that I’m talking about and we all need more of that.

Alison Jones: Yeah, I couldn’t agree more. He’s so great. We had him on the podcast and he also followed through with the whole rule-breaking thing with the promotion as well. Did some really cheeky PR stunts.

Jackie Fast: Yeah, yeah. Yeah. He did, he did.

Alison Jones: Really walking the pirate talk.

Jackie Fast: Yeah, no, no, that was great. Are you talking about the Oprah thing?

Alison Jones: Oh, is there another one? I’m talking about the one where he did the Penguin Random House… He used it basically as a billboard after having being expressly told that he couldn’t do that.

Jackie Fast: Yes. Yes, yes. Yeah. There’s a couple other things. I maybe I won’t mention them cause he got into trouble

Alison Jones: Now, come on. What happened?

Jackie Fast: Oh, okay. So Sam very kindly endorsed my book and I was on his website and he had Oprah kind of waving his book around. And I was just like, how the hell did that happen? And I did research into like Oprah books and I was like, they don’t do business books.

 I was like looking through, looking through it and I couldn’t figure out how he did it. And so I just emailed him and I was like, did your publisher get that for you? Did you do that? Like, what did you do? Cause I can’t figure out how it happened?

He said, oh, I Photoshopped it. Oh my God. I love you so much for saying that.

Alison Jones: Deep fake.

Jackie Fast: Yes. I love it. He’s like, he tagged her and everything. He’s like, he thought it was an obvious fake. I was like, well, you sure as hell convinced me, but I mean, it’s just stuff like that. It’s great. Right? And why not? Why not do that?

Alison Jones: Yeah. Yeah. I have say actually one of our authors did that, Lucy Werner with Hype Yourself, we have Bill Gates looking intently and, you know, with a sort of real absorption at Hype Yourself. It’s fantastic.

Jackie Fast: So good. It’s so good.

Alison Jones: Love it. So Jackie if people want to find out more about you, more about the work that you do, more about your book, where should they go?

Jackie Fast: Well, if people are interested in me, you can check out my website, which is just jackiefast.com or I’m on Instagram as well at Jackie Fast. The book can be bought anywhere books are sold. I mean, you can Google it Rule Breaker, rebellious leadership for the future of work. And I mean, I’m on Twitter as well at Jackie Fast.

Alison Jones: Fantastic. I’ll put those links up on the show notes at extraordinarybusinessbooks.com.

Just brilliant to talk to you, Jackie, really, really energizing. And I love the way that you make the writing of the book like, well, I just did it like this. It’s so angsty, which is brilliant. You just do it, you know,

Jackie Fast: Yeah, just, I just did it. Yeah.

Alison Jones: You just do it, so people, if you’re listening, if you’re angsting out, just stop it, just do it. Okay?

Jackie Fast: Agreed. Agreed. Couldn’t agree more.

Alison Jones: Be more Jackie. Brilliant. Thanks for your time today, Jackie.

Jackie Fast: Thanks so much for having me. I really appreciate it.

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