Explore courses

Career Skills with Maddy Guest, Co-Founder at You're in Good Company

career skills & transitions


What's your career story so far? 


Maddy Guest: So I started as a grad at Macquarie group down in Melbourne. So I was in their asset finance team there. And I spent around two, two and a half years in that team. And honestly, for anyone who I think is considering like how or where to start your career, I think in a big sort of corporation like this, I'm sure Lucy, you also have your own thoughts about this.


We have laughed about this before, but I think


the skills that you can learn in that kind of corporate environment have just been so invaluable.


It sounds so simple, but it's literally things like how to write an email in like a formal and like professional manner, how to answer the phone and have a conversation with someone, which I know just sounds ridiculous, but seriously actually takes like a level of confidence and actually knowing how these things work to be able to do it.


So that was great from Macquarie. And then Basically what was happening in the background towards the end of my time there was COVID. And one of the things that arose during COVID is wanting to do the podcast that I now have called You're In Good Company with a good friend of mine. The background of that was like, It, the podcast is all about investing and learning how to invest in the stock market.


And we obviously during COVID there was like a massive bull run and everyone wanted to learn how to invest and make money. And so it really felt like the right time to do it. And I, at the same time actually got referred into a new role at PwC. So, I sort of started the podcast at the same time that I started at PwC and that was the, at PwC, I was in a team called Transaction Services.


So essentially the way that I like to describe it is you looking at the financials of a business. So when one business either wants to buy another business, a business wants to sell or list on like the stock exchange so that it becomes public and you can invest in it, or if two businesses want to merge and come together, where you get involved to look at the financial statements of the business and basically identify.


What are the key opportunities? What are the biggest risks? And like what do you need to know about this business and how it runs so that when you are the new owner and you're gonna take it forward, you know what is going on? So I did those two things around the same time. And that was about two and a half years ago.


And then about one year ago, oh, sorry, that would've been three years ago and about one year ago I moved up to Sydney from Melbourne. And I actually moved him slightly within PwC. So I still work very closely with my old team, but what I do now is it's a team called financial sponsors coverage. So we work with private capital.


So whether it be venture capital private equity is probably where we spend most of our time and it's about sort of helping them to. Number one, like find new opportunities to invest in. Number two, it's about helping them with their existing investments and sort of bringing the whole like PwC machine together to help them.


So we kind of think of ourselves like an interface. And then number three, it's around like internally at PwC, actually coordinating our strategy for private equity. That was a very long winded way of describing how I've gotten to today.


Lucy Wark: Oh, I love it. Amazing. So you've started out in banking, you've moved into kind of a new company, a new role, and on the side, you've also started what's become a very popular podcast.


Speaking about investing in the stock market. I'd love to ask




What does an average week look like?


Maddy Guest: A great question. So what I will say is in my old role in transaction services, the hours were like incredibly demanding.


So that I think was a lot more challenging. We would be doing the podcast. Fortunately, Soph and I have like similar roles. She works at a different company, but we're kind of on the same page with this stuff. So weirdly, it actually does align. But honestly, we would be doing the podcast at like either 7am in the morning recording our poor guests, making them do that.


We would be doing it at like 10, 11 PM at night and then on weekends. So it was pretty intense and like to be transparent by the end of it, I was pretty burnt out and not in a great way. Surprise, surprise. What has happened since my shift to Sydney? My role has changed a bit. It's still like, we still work very hard, but I would say it's a little bit different and maybe we can get into this a little bit more.


It's not so much that I'm like executing tasks and it's much more like strategic and bigger thinking. And so it's a very different style of working. And so I have found in some ways it's become like a lot easier to do the podcast, but in others, because it's like, that more kind of like creative thinking and mindset.


It's almost harder because it used to be that all my creative thinking went to the podcast and then at work I was just like executing and now it's kind of like a bit more competing between those two things. But yeah, I think a lot of the podcast stuff gets done either early hours of the morning.


Fortunately, I am a morning person or late at night or on the weekend.


Lucy Wark: And I, I saw just looking at your bio that you were a rower or, and used to be a rowing coach as well, which I think weirdly, one thing that I've noticed is like some of the most like productive and efficient people I've ever met are rowers and have like the strongest work ethic.


And I suspect it's partly that you were like, Oh, I had to do my homework in like a very limited number of hours. And I had to basically just withstand a lot of pain.


Maddy Guest: It's so funny that you bring that up because then I was just saying, I was a morning person, I was about to say like, I was a rower and I was like, don't be wanky.


Lucy Wark: No, no, no, no. I have seen this up close. I used to live with someone who used to be a very good rower who's also like the hardest working person I've ever seen. And weirdly like still cheery at 2am when she was working. Which I cannot achieve. But yeah, it's weirdly a strong pattern with rowers.


Maddy Guest: I will say like, it teaches you great life skills. I mean, for context, like in year 12, where we're training 12 times a week. So that looks like, like Monday before and after school and lunchtime, Tuesday before after school, lunchtime, Wednesday was a day off, Thursday. Was the same again. And then, right, I think I've done maybe too many in there, but Saturdays was like a full day as well.


And like, it was intense. And also because you're waking up so early, I was like, I need to be in bed by 9 30 or even 9 PM, otherwise I can't operate. So it makes you incredibly efficient in terms of like, Getting your work done in like tight periods of time, but it's great lessons that you can carry through the rest of your life.


Lucy Wark: Absolutely. Yeah, the final question of this is going to be, is there anything you want to plug? And I think it's like rowing, that's the answer.


And if not rowing, find something equally brutal and time consuming if you can.




What ingredients, skills, and attitudes have been important for you early on in your career?


Maddy Guest: Yes, I love this question. The first thing that comes to mind is enthusiasm.


I think just genuine enthusiasm in whatever you're doing I think has put me in such good stead.


I feel very fortunate that I found an industry or kind of like a career that genuinely gets me very like excited. And I love learning about it. And I love having conversations about it. So that definitely helps from the enthusiasm, enthusiasm perspective. But I honestly think just that, like energy of like putting your hand up and being open to opportunities has meant that within my organization, like I have become someone that and I think to an extent the podcast helps with this as well.


Like people now go, oh, she can talk. So it's like when there's an opportunity for someone to be on a panel or to present or to do something, they go, Oh, let's get Maddy. And it really compounds. I think like that attitude, when you are putting your hand up for things, and when you are showing that you can do things to just give yourself really like incredible opportunities and to be put in the position where you're open and available for those.


And then the other one I think is just to be authentic, like be yourself in your workplace because I think having those connections with people and like building really genuine relationships with people just helps so much.


Lucy Wark: Awesome. And yeah, I think that's so true, particularly about showing skill, like putting yourself in positions of maybe a little bit of discomfort, but being willing to like showcase those skills makes such a difference.


And even like when you're on teams, particularly like the harder the work is or the more challenging it is, like it's such a night and day difference between like, a team of people who are enthusiastic and even a team of people who are enthusiastic and sort of one person who can feel like they don't want to be there or who kind of views their job as pointing out problems.


And there's a balance to be found, but I think there's like immense value in just. Being like energy giving in whatever that looks like for you.


Maddy Guest: Well, it's just more fun, right? Like I think of so many circumstances where particularly my first role at PwC, like we would be working really late and it's like,


you can either sit there and like be depressed about it and be an energy drainer or you can have a group of people that you're there with and like have a bit of fun with it.


And that was a lot of like, really great memories of like delirious, It's funny, enjoyable nights where it's like, I actually kind of wanted to be there, like it sounds a bit weird, but it's like, yeah, it was, it was a lot of fun. And I think that comes down to just your mindset around that kind of thing.




What's the biggest career transition you've made?


Maddy Guest: Definitely I would say my move up to Sydney. And I sort of alluded to this a little bit before, but in this new role that I have gone into, it has been a massive shift in like the style of working. So in my roles thus far, it's very much, I think, or prior to this job, it's very much been execution focused.


There are like lots of jobs to be done and it's just about kind of doing them. Whereas when I moved into this role, it was a real shift of behaviour and mindset because in a way, like when I first joined, I kind of was like, God, i feel like I did nothing today. People might not even realize like, whereas in my last role, there was like no way that that would happen.


Obviously I wasn't doing nothing, but it was more


I had to become much more self driven and much more kind of like creative and think about things differently in order to be good at my job.


And so even just things like time blocking my calendar, like I had to like put in a block and be like, okay, for this hour, you're going to think about and work on this.


And then for the next hour, you're going to do this as opposed to just taking off that long list of tasks. So I think it was that kind of shift in style of working that has probably been my biggest transition so far, but I'm so glad that I have done it because I think It puts me in much better stead for like the kind of roles I want to do in the future.


Lucy Wark: Absolutely. I think so many leadership roles, people kind of start becoming a manager or start moving from manager to org leader and realize that there's no one telling them what the agenda is, or you might have a sense of like what success might look like in your role on a very long term basis. And that's quantifiable in some way, but in the short run, that all becomes a problem.


Maddy Guest: 100%. It's a bizarre and like quite a challenging I think transition to go through and you do have to be like very self driven and quite accountable, but yeah, I'm glad I've gone through it at this stage, at this sort of stage. Awesome.




What's helped you to take that step from being an individual contributor with a lot of responsibility into setting the terms of your own work a lot more?


Maddy Guest: Hmm, good question. I think, to be honest, like


a lot of the sort of help that I've got has been from talking to people about this.


So like, I remember having a conversation with a friend and like, that's where that time blocking tip came from.


And it's such a minor thing, but it's like that actually had completely just transformed the way I work. And so I think it's having lots of conversations with people about. And I think this applies to like all parts of your career about where you're at and how you're thinking about things and sort of getting that feedback and advice.


I just have found so incredibly valuable. I'm a big like talker to people. I just love kind of making those connections and soaking up different pieces of advice and perspectives. And like, I've literally have just always. And I think I have learned so much along the way from having that sort of attitude and approach.




What's the best career advice that you've received? 


Maddy Guest: I think the best career advice I have received, one that comes to mind is to


think like your boss.


I think this is probably particularly relevant in a corporate environment. So I'd be keen to like get your thoughts. I'm sure it's relevant everywhere. 


I think like in my experience there are often quite big generational divides, just like between junior and senior staff members in the organizations that I've worked in so far.


Just in terms of like being junior and being young and then by nature of like the more senior people having been around for a while. And I was very conscious and always have been that like the environment that we're sort of in now, which is like where we value flexibility and we value, you know time and work life balance.


And all of those things is like very different to what a lot of that kind of next generation up have experienced in their work life so far. And I think there is a lot of like legacy sort of beliefs around, you know, having to do your time or having to work in a certain way and look a certain way and dress a certain way.


And one of the best pieces of career advice I've got is just thinking from that perspective and being very aware of it. And I think that's put me in really good stead because I see a lot of people who it's like, yeah, but I don't care about this. So like, this is what I value, which is fine.


And it's great. And I still like think like that and have those beliefs. But I think it's like, when you're aware of the way that your leaders are perceiving things, thinking about things, judging different people in their organization, Like, what does that actually achieve if you want to be successful in that environment?


If you just completely disregard their opinions and beliefs and thoughts. So I think they're getting into the mind of your boss and like thinking about things from their perspective has been a really good way that has kind of allowed me to be successful in my roles.


Lucy Wark: Yeah, I agree with that very much.


And maybe the version of that, that I would do like in a startup environment, and this probably holds true in a corporate too, is learning to manage up as soon as early as possible. The thing that will happen to you if you're not already a manager is that at some point you will be given people to manage and you will suddenly, like becoming a parent, have this newfound empathy for your managers good and bad that you've had throughout your career, because you'll realize that it can actually be really challenging to not be the person who owns the work, but to be able to engage with people who also have different styles and preferences, build a team dynamic and make sure that you're getting the best possible performance from each of those people. And also that the team is like getting the work done on time, that the work's at a high quality, like you own a lot of things, but you don't get to directly do the work yourself.


And yeah, so I think managing up can be like, okay, with empathy for that person, what does a manager need to essentially make me someone who is super reliable and then someone who they can give more opportunity to who they can invest more time in developing, et cetera. And so often that's like giving visibility more often over your work.


So updating more frequently so that they know where it sits. It's like learning prioritization conversation in a very proactive way so that you can be like, okay, great. I think I've got. 100 percent of my time and I've got 120 percent of like work which 20 percent do we want me to drop? Because they might have priorities that you aren't on as across and finding that out will ensure that you're doing the right work if you're like coming with solutions when you have problems.


So being like, Hey, I've gotten as far as I can on this. Here are the three ideas I have for how to fix it, but I'm a bit stuck. Can you help me instead of just being like, I don't know what to do. So there's all of these smaller things that like ladder up to being the type of person who a manager is like, they're a really safe pair of hands.


And there's someone who I want to see succeed.


Maddy Guest: I think that like comment right at the end, safe pair of hands is just exactly everything that you have just said comes back to trust. And I think


if you want to be good at your job and be successful at work, you need to build trust for the people around you and


All of those tips you've just given are like the perfect way to do that.


Like in my current role, we have like a big boss who we ultimately report into, but he, his day job is something completely different. And so, so much of what we do is around like making sure that we're communicating what we're doing really clearly. And, raising things where we need his help or his kind of like weight to go in on something or his feedback, but then also knowing like what we don't need to bother him with as well. And so, yeah, I completely can get with everything you've just said.


Lucy Wark: Definitely. I, there's even, if for people who are like super nerds on this, like task relevant maturity is like a classic way to express this idea, which I think I got from Andy Grove, the Intel founder's book on managing people that has that concept in it.


But certainly like as a broad idea, just being able to like understand that, like the more trust and credibility you build with your manager, the less they need to manage you. And like, the more that pendulum can swing from like oversight into like support and flourishing and opportunity. So I think I, I've heard a lot of people, particularly Gen Z actually being like, I really hate being micromanaged.


And the thing I'll always say is like, I think


you need to earn like enough trust for someone to take their hands off the wheel and trust that you can steer


And so the, the way to not be micromanaged is be really good.


What is one resource, book, podcast, article that has helped you?




Maddy Guest: Some that come to mind like I love the How I Built This Podcast, although I feel like it has gone a bit rogue recently, or maybe I just haven't been listening as much, but Diary of a CEO is like such a great one, especially a lot of those early episodes around different themes of like building a business and marketing and things like that.


And then I would say in terms of career advice, I mean, at the opening of our own podcast, You're In Good Company, we have the quote, which says


the best career advice that you're not getting is to invest.


I think when I guess we take a step back from work at the end of the day, you're there to earn money and to support yourself. And so I think learning more about investing and learning more about different ways to kind of grow your wealth that is not just your nine to five job or your whatever hours you do job.


There are lots of great like investing books. One that specifically comes to mind is what's that dad one, Rich Dad Poor Dad.


Really easy read. And basically the premise is this kid that grows up and his dad is not very wealthy, but his best friend, his best friend's dad has like made, generated a lot of wealth for himself through investing and being creative.


And the sort of overall premise is like the way in which building wealth allows you to like step off that kind of like treadmill or hamster wheel of, you know, working when you need to rely on your job to pay your mortgage, to make your bills and actually be able to kind of, I guess, create more flexibility for yourself by generating wealth externally and supporting yourself more holistically.


And I just loved that like framing. So read that and then go and listen to the podcast. So you know how to actually do it.


Lucy Wark: Amazing. And yeah, it's You're in Good Company is the podcast. So you can Google that and find it and it's awesome. I highly recommend it. And definitely, I think that idea of learning early as well is really important, like a lot of us may.


Particularly women miss out on a lot of the messaging around building wealth through investing as opposed to building wealth through budgeting, which we spoke a little bit about when we, we talked, but I think the thinking about like starting early and the power of compounding is also really, really helpful.

So like, there's no day like today.


Maddy Guest: Like, I mean, there are so many stats around the amount of money that you can retire with. If you start today versus next year, this is next year. And the differences are huge. And so that's why the benefits are so massive of just getting started. Just do it.


Lucy Wark: Yeah. I also say this about negotiating for the same reason.

It's like equally when your employer's index on your salary year to year as well. Like the. Benefits of negotiating actually have like similar compounding effects as well. But that's for another time. Thank you so much, Maddy, for joining us. Really appreciate it. And if you want to find any of Maddy's stuff, we'll link to it.

But yeah, delighted to have you here and thanks for all the good career advice.


Maddy Guest: Thank you, Lucy.



This interview transcript has been edited for length and clarity.



LookingĀ to level-up?

Explore Fuzzy's programsĀ for live and self-pacedĀ courses to develop career-accelerating skills.

Learn more