This transcript has been edited for clarity and checked against the available source transcript and recording. Filler, false starts, and obvious transcription errors have been corrected without changing the speaker’s meaning.
Intro#
James: Hello, and welcome to Graduate Theory. Today’s episode is a great one. We go really deep with someone who is passionate about graduates, and about you taking control and growing your career.
On this episode, we speak about overseas travel, starting a side project while you’re working full-time, different cultures and how they work, mentorship, and ways to plan and build out your career. There’s so much value here. We covered so many different angles of so many different things.
This episode is one of my favourites. If you want to get it straight to your inbox and read my insights and what I picked up from it, please go to GraduateTheory.com and subscribe to the newsletter. You’ll get my thoughts and the different things that I picked up from the podcast.
You’ll also find more information about different things that we spoke about on the episode today. Without further ado, let’s dive in.
James: Hello, and welcome to Graduate Theory. My guest today graduated with a Bachelor of Commerce from the University of Melbourne in 2015. He has worked at Goldman Sachs and PwC, where he worked in Silicon Valley on billion-dollar deals like the Uber IPO. Since returning to Australia at the start of this year, my guest has started working as the Australia and New Zealand finance manager for Airwallex. He works as a mentor at VC firm Blackbird and as a startup mentor at Textbook Ventures.
On top of all this, my guest runs his company, 87 Advisory, where he helps small businesses perform financial due diligence over their M&A and venture capital processes. Please welcome to the show the highly accomplished Haynes D’Souza.
Haynes: Thanks, James. Thanks for having me on. That was a very warm and generous introduction, so feel free to keep going. That was great.
James: You’ve done so much, and it’s going to be a great conversation today. I’m really excited to get into all the things you’ve done in your career.
From Melbourne to Silicon Valley#
James: When I was researching you, one thing that really stuck out to me was this move you made from Australia to America and Silicon Valley.
Was there a key moment that led to you deciding to go to Silicon Valley?
Haynes: Before I moved over to SF, I did two years in Canberra. I worked at the Australian National Audit Office. I initially started very optimistic about government. I wanted to learn how government works.
I wanted to learn how the military worked. I spent a lot of time looking at consulting and audit projects for the military and the Department of Finance. But then I got to the end of two years and just wasn’t being challenged. I was in my mid-twenties, and I looked at people five, 10 or 15 years older than me.
I didn’t find that trajectory too challenging. I’ve always been a big believer that all Aussies should go and work overseas, so I reached out to a few networks at PwC, where I had worked in Melbourne for a bit, and said, “Look, I really want to go to San Francisco.”
People said, “Look, it’s a lot like Melbourne. The coffee scene is just as good. It’s just as expensive.” Interestingly, it was either that or Germany, and I hated German food anyway. So I made the move across to San Francisco and was there for about two years.
That’s where I caught the tech bug. I worked on the Uber IPO, met some amazing people and saw the work ethic of entrepreneurialism. It changed my outlook on many things, not just work but life more generally. You work overseas, and you see folks who have gone to Harvard, Stanford and some of the elite universities working in these amazing jobs.
You try to internalise some of those learnings and bring them back home. That’s what I’ve tried to do, being with Airwallex right now and doing a whole bunch of mentoring and advisory work as well.
James: That’s really exciting. You mentioned connecting with people who went to these Ivy League universities, which is incredible, but what are the main lessons you’ve taken from connecting with those people and working on those projects? Is there anything that really sticks out to you as something you’ve taken back?
Haynes: Growing up in Australia, we came here when I was eight. I grew up in the northern suburbs of Melbourne, and for a long time that was the world I knew. Then you meet other Aussies when you travel, and you see that their perspectives are global.
Your ability to make a difference is global. When I met folks in San Francisco, the biggest takeaway for me was: don’t be afraid of starting an idea or having a business that can have a global impact. Sometimes in Melbourne, or in Australia, we can get isolated on this part of the world and lose sight of what’s going on in the States and Europe.
But that was the emphasis I saw among folks in San Francisco. They’re like, “Look, there’s a big problem. I’m going to try to fix it globally, and I’m not going to take no for an answer.” That relentless optimism and drive is what I saw in many Aussies in San Francisco.
I saw it in many US folks there as well. I highly recommend that all graduates, and young adults too, go over to the States and experience that secret sauce of optimism, positivity, relentless ambition and the drive to say, “There’s a problem. I’m going to try to fix it.”
That grind and hustle is something we sometimes lack in Australia. I’ll give you a really good example: you go there and meet folks who have second or third jobs. As grads, they’ll be working at PwC and doing tutoring on the side, or they’ll be a nurse and work in retail on weekends. The concept of having second and third jobs is very foreign, at least in the circles I hang around in here.
That’s not to say it’s a positive, because a whole bunch of social issues force people into that position. But their grit, determination, positivity and relentless drive really stood out to me.
Tall Poppy Syndrome in Australia#
Haynes: You wonder why we don’t really see that in Australia. I was listening to an interesting episode of a podcast called the Aussie Startup Playbook. In one episode they talk about tall poppy syndrome in Australia and the fact that you always get pegged back a couple of notches here.
If you’re seen to be working a little harder and taking that extra risk, you get your mates saying, “It’s Friday night. Why aren’t you going out? Why are you still working? Why are you working your tutoring gig? Why do you have your business? Why do you have X, Y, Z? Just come out with the rest of us.” Whereas in the States, especially in San Francisco, spending your weekends working on a side project or side hustle is seen as the norm.
Maybe it is that cultural difference. In Australia, being on this side of the world and being the lucky country, we can afford to be a bit more chill about things. I never really saw that in San Francisco; it was go, go, go at all times.
James: I think that cultural shift is really interesting. I’ve heard that about tall poppy syndrome as well. Like you were saying, when someone starts to do a bit more, people are kind of like, “You shouldn’t be trying so hard. Just chill, man.”
Haynes: I’m interested to hear, in your social group, how many folks have a side hustle, an e-commerce store or a second source of income on top of their nine-to-five?
James: None that I can think of off the top of my head. The hardest-working people I know maybe work a few extra hours at their core job, or work 10 hours a day. Not many people have something they go straight onto after work. It’s usually, “Clock out, then Netflix time.”
Haynes: One of my mentors back in SF would tell me, “Everyone’s got their nine-to-five, but then everyone’s got their five-to-nine as well.” That’s stuck with me. I encourage everyone who can to at least learn another skill or side-hustle their way into something.
Lessons from Covid in New York#
James: On that, you have your own side hustles and things that you do. You’re obviously involved in a lot of things in the startup world in Australia. Did this belief you have now about running a startup and how great that can be stem from your time in Silicon Valley, or was there a key moment when you thought this kind of thing would be really beneficial for people?
Haynes: I stayed in New York for a while during the middle of the COVID pandemic, on the Lower East Side. For the Australian listeners, I don’t know if you remember Governor Cuomo having his daily press conferences.
I was in Manhattan right in the middle of that, and I saw the impact COVID had on small businesses. That stuck with me. Picture living in Manhattan, surrounded by bodegas, delis and family stores.
Immigrant families come to America and put their whole life savings into a tiny grocery or deli. COVID happens, the entire city is deserted and everything stops, yet you see these business owners still trying to make a living. That visual stuck with me. A big part of my values and what I’ve learned is that you should always try to work hard and have the grit and determination not just to have your nine-to-five, but to have a business on the side.
That’s really stuck with me. Going back to New York and seeing these family-run delis closing down, I saw the children of immigrants go to school or work their day jobs, then come back and work in their parents’ business, helping with inventory, marketing and all these things.
I took a step back and said, “Look, I can do my nine-to-five corporate job.” I’ve worked with folks who have done that, and that’s certainly fine. Folks have kids, families and other commitments. But I saw the level of grit, drive and determination there and thought, “That’s really freaking amazing.”
For the grads and young folks listening, we’re probably going to work for about 40 to 50 years. I don’t want to look back at the end of that saying I didn’t take a risk, go out and build something, or have something that will last beyond my career.
I really want to have an impact. That’s the fuel in me to say, “You’ve got your day job, but where else can you add value? What other challenges and projects can you take on?” That visual of being on the Lower East Side, with the city deserted and an immigrant family carrying a ton of debt and paying a ton in rent while still trying to make it work, stuck with me.
The second part is that I had a really formative economics teacher in high school. I was probably in years 10 and 11, about 16 or 17 years old, and didn’t really know what to do.
When I was a kid, I wanted to be a pilot. It turns out you have to be good at physics, and I suck at physics, so that was out the door. Then I had Lucas Benda as my economics teacher, and he explained the world to me through markets, like demand and supply.
I thought, “This is really interesting.” As I spent more time learning economics and how markets work, the power of owning assets became clear to me. Economics taught me about different forms of resources—capital, labour and natural resources. Even through university, the big thing that stuck with me was that you want to be in a position where you’re owning assets.
A big part of that came through high school economics and playing games like Monopoly. I realised that if you own all the properties in Monopoly, and everyone passing by pays you rent, then you’re in a good spot.
That stuck with me. It sounds strange to say, but the ability to own assets, build businesses and own equity is something that stayed with me. Applying that now, if you work at a big bank or an accounting firm, you’re an employee.
I wanted to see the hard work I was putting in result in a commercial and financial impact for myself. As an employee, you don’t necessarily see that because you’re getting a wage for working those 40-hour weeks. But you don’t really see, as the business grows, how you’re being directly compensated for it.
A big part of it was owning assets and having equity. To extend that a bit more, starting a business or investing in other companies gives you that almost Rich Dad Poor Dad mindset, which everyone seems to read now.
Those are probably the two things that got me into this.
James: It’s great that you have those experiences and things driving you towards this, and that you’re also helping other people do it.
What makes a successful startup#
James: Have you seen people go through this startup period, creating a company they want to turn into something big? Are there any trends among the people trying this that make them more likely to succeed?
Haynes: I’d say there are three things, based on what I’ve recently seen among folks starting businesses in Australia and whether those businesses take off. The first is this circle of competence. You’re more likely to succeed if your business falls within an area you’re either really competent in or really passionate about.
It’s no secret that being a business owner is tough. You’re working weekends and long hours. If you’re not really competent, don’t have a really competent team, or aren’t passionate about what you’re doing, forget about it, because you’ll be found out. Your short-term interest and enthusiasm will last a couple of weeks or months, and then you’ll find it very difficult.
The second thing is what I call structural shifts. You want to have a business with structural and economic tailwinds. There’s no point making Kodak cameras in 2021, because no one’s going to buy them.
Similarly, you want to solve a problem in a commercially viable way, with structural tailwinds behind you. There’s a really good website called Trends.io where they show you what people are Googling.
They show you, on the retail side, what people are interested in, where conversations are happening, where the structural forces in the economy are shifting and which way the wind is blowing. You want to have a business going downstream rather than fighting upstream.
A couple of really good examples come to mind. Yesterday, I was advising a company where two founders are building a business very similar to Mr Yum. Mr Yum is an Australian technology company that helps restaurants take their menus online, lets customers order via QR codes and handles reservations digitally.
That’s such a big problem right now. Everyone is going into restaurants, they have QR codes, and there’s a structural shift towards using technology in restaurants. These guys are starting a business to take advantage of that. It’s much easier because they’ve got this massive structural tailwind behind them, as opposed to doing something that goes against the wind.
I hope that analogy makes sense: understanding and capitalising on structural shifts. The third thing is resources, both capital and people. Depending on what your business is, how capital-intensive or technical it is, you’ve got to have the right people, skills, financing and liquidity to survive. In the startup world, we talk about zero to one, one to 10, and 10 to 100.
Each stage has different requirements from a resourcing perspective, and I define resources as people and finance. At each stage, you have to figure out: what are the key skills I need to go from zero to one, one to 10, and 10 to 100? What other skills do I need? Where am I lacking? Then go from there. At a very high level, those are probably the three things I see determining whether something grows.
The Importance of Timing for Your Startup#
James: Those are really great pieces of advice. I totally resonate with what you were saying about tailwinds, because if you look at almost any company, the timing of when they came out with their product is one of the most important factors in their success. They’re always riding an underlying trend. Even Google and Facebook were riding the growth of the internet.
If someone starts a YouTube channel, being early on YouTube—even if they’re not that good at it—is going to be a massive factor, maybe more so than their actual skill.
Haynes: To extend this with a few examples, let’s consider a hypothetical: would the Tim Ferriss podcast be as popular as it is now if it started today? There are so many podcasts now.
The Tim Ferriss Show is one of the most popular podcasts out there. He had one of the first productivity and performance-coaching-type podcasts. I’d guess that if he started it now, it probably wouldn’t become as successful in four or five years as it is today. He was one of the first people to do it and do it well.
You also see it with a lot of social media and tech companies where the timing is right. You can be too early or too late. You need to find that structural tailwind and have the momentum where it all comes together and all your ducks are in line.
Some of it is skill, and some is just luck: the right place at the right time.
James: It’s a good point about Tim Ferriss, because there’s a book he’s spoken about called The 22 Immutable Laws of Marketing, I think. One of the ideas in it is about creating your own category or niche.
It’s the same idea: “We’ll create our own and be the first podcast talking about productivity,” which is almost what he did. Then he was able to ride the trend of podcasts becoming popular. As well as his own growth, he was riding the growth of the underlying trend.
I’ve even seen this with note-taking software. I use Obsidian, which is similar to Notion in many ways. I started using it in March last year, quite early on, and certain people were starting to make tutorials.
The growth of that community has really enabled the growth of their brands, probably more than they would have grown through their own improvement if the community had stayed at the same level.
Haynes: Another example is some of the early YouTubers. Casey Neistat, MrBeast and all these really famous folks now started probably five to 10 years ago. If Casey Neistat started today, it’s so competitive that I don’t think he’d be where he is.
Look at TikTok and the D’Amelio sisters. If they jumped on TikTok now, would they be as successful as they have been? I don’t know. It’s an interesting hypothetical, and it supports the point that timing is everything when starting a business.
It’s interesting to shift from viewing a business as, “What is a problem and how can we solve it?” to, “What underlying social trends can we piggyback on and ride?” Nothing lasts forever. It will be interesting to see how some Aussie tech companies, especially Atlassian and Canva, ride that wave. A big part of it is also pivoting.
Once you realise you’re in your first wave and that growth is starting to slow down, where can you pivot and switch to next? Sometimes the pivot can be more successful than the original push. Apple is a good example. I feel like it’s mid-pivot: it was a computing company, but now it’s pivoting into more of a services company with the whole range of products it has. Twitter is another good one.
If folks want to Google successful company pivots, they’ll find examples. Sometimes structural tailwinds change, and it’s on your company to shift with them rather than resist that change.
Upcoming Trends#
James: Are there any trends where you think we’re right at the start, similar to how we were talking about the internet and different communities? What do you think is beginning at the moment, and what would you almost bet on being popular in five years?
Haynes: Let’s first see where we’ve come from in the last six to 12 months, then extend that out for the next few years. In Australia and globally, we’ve been in lockdowns for as long as I can remember—about two years.
Everyone is working from home, eating at home, working out at home and doing Zoom calls. There’s been a fundamental change in the way people interact, and I don’t think we’re going back to where we were previously, at least not to the same level.
In terms of consumer behaviour, there’s been a structural shift and greater acceptance of eating at home, getting groceries delivered at home and working out at home. My first takeaway is that we’re now more comfortable using technology to get things delivered and work remotely.
My second big takeaway is that I’ve seen so many people start e-commerce and Shopify stores, blogs, vlogs and TikTok accounts. Over the last two years, people have been moving from content consumption to content generation.
I think it’s much more acceptable now for people to create content, whether it’s TikTok, websites, YouTube or podcasts. It’s becoming more socially acceptable. Those are the two big trends I’ve seen recently.
How will this play out in the next five to 10 years? I love tech companies. I really believe in the power of technology to disrupt dinosaur industries. If you’re in a space where you’re helping people take what was previously an outdoor function and bring it indoors, or even better do it remotely, there’s a structural tailwind.
What do I mean by that? If you’re a company facilitating or enabling food delivery, remote work or remote telecommunications, you have a structural tailwind. I don’t think we’ll return to the old ways of working because that has fundamentally changed.
The winners are probably companies like Zoom and Peloton. The losers include commercial real estate. I’d hate to be CBRE right now. It will be interesting to see how it all works over the next five or 10 years.
If you’re starting a company that helps people be more remote and live their best lives in a geographically agnostic way, I think you’re onto something. The second principle is that we’ve seen people become content creators, and that’s now okay and encouraged.
If you’re starting a business that helps or advises people on marketing and content creation, including data analytics and understanding their audience metrics, there’s a big structural tailwind you can piggyback on. It is starting to become quite a congested space.
There are a lot of social media consultants, but even on YouTube you get certain niches, whether they’re about property or animals. No one used to vlog themselves buying a house, but now I’m seeing a lot of that.
Figure out a way to be part of that space. I don’t know what the answer is right now, but it’s definitely a structural tailwind. It’s becoming more socially acceptable to be a content creator rather than just a content consumer. Another shift I’ve seen touches on what we discussed earlier about people having multiple jobs.
I don’t think the future model of work is necessarily five days a week, nine-to-five. COVID and lockdowns have shown that people can get work done when they’re not in the office, and sometimes outside nine-to-five because they’re in different time zones.
I remember when I was in the States and COVID hit, a lot of people left San Francisco and New York for other cities, Hawaii or Latin America. They still got their work done. I don’t think we’ll have this culture of, “It’s nine-to-five and you’ve got to be in the office,” any more. What does that mean going forward, and what are the tailwinds? I think people are more likely to take on second and third jobs. They might work at one job four days a week, another one day a week and another half a day a week, or work part-time across three jobs.
They might leverage sites like Fiverr and Airtasker and be in the gig economy, where they’re not really an employee but are still working.
That’s another takeaway from the last two years that I think will stick around for the next five or 10 years and become a structural tailwind. In terms of starting a business in this space, think about the gig economy and understand: okay, you’re a contractor; what skills do you have, and what gaps are out there that you can plug and work on?
For example, if you’re an engineer, can you take on freelance engineering gigs? If you’re a visual creator or artist in Colombia, can you take on a few tasks in the US or Australia and get paid in dollars while living in pesos?
I think you’ll see a lot of that in the next few years. It’s definitely not a good time to be in commercial real estate, because folks are working remotely and things are becoming very location agnostic. Those are some of the structural tailwinds I was talking about.
Another point I’d like to add is that companies are realising the power of users’ data. A big structural tailwind I’m seeing among large tech companies is the realisation that customer data is really valuable.
In acknowledging that, they’ve decided to build platforms. If you have a platform business that connects buyers and sellers, or provides multiple products and services that are interconnected in different ways, having that moat is valuable. The structural shift I’m seeing is companies asking, “How can I be a marketplace? How can I be a platform?”
You’ll see a lot of investor pitch decks where they say, “We’re a platform. We connect buyers and sellers. We rely on network benefits,” or, “We want to build a suite of products, not just one, and fill the value gap from the low end all the way to the nth degree.” That’s another change I’m seeing.
Haynes’ Favourite Failure#
James: I want to take this conversation into your career. Is there a particular failure that you’d call your favourite—one where having that experience led you to greater things?
Haynes: I’ve got several, James. I’m trying to think of the one that had the biggest impact. I joined PwC Australia as a trainee when I was 18. I applied while I was in high school and, to be honest, I barely knew what PwC was.
I came across a website where they were looking for folks and thought, “I’ll apply and see what happens.” I was lucky enough to join as a trainee and was there for just under two years. It was my first job, and the biggest feedback I received was about understanding how to communicate and deal with clients in a corporate way.
I had some really strong feedback: “Haynes, this is how you should think about dealing with clients, how you put together a memo or, in the audit world, a workpaper. This is how you deal with client relationships.”
All of that was new to me. I started at the end of my first year at university. The biggest failure I had at that point wasn’t so much a failure as receiving a lot of really constructive feedback, which you never really get in high school or at university. A lot of feedback there is academic: you’ve got an essay or a test; did you do well, and how could you improve? This was my first job in a corporate workplace.
I received constructive but strong feedback about how to deal with clients in a meeting, or how to go about fixing a client problem.
Putting together an audit workpaper gets very technical. No one had really shown me how the corporate world works. It’s an interesting skill set: this is how you put together an audit workpaper, and this is how you interpret and apply accounting standards. The feedback along the way showed me a couple of things.
First, we generally do a really poor job of teaching folks and getting them workplace-ready and job-ready. You go from high school to university, then bang, you’re at work wearing an oversized suit and sitting in meetings where you don’t really know what’s going on.
I’m sure it has got a lot better now, but that transition from high school straight into the workplace was very steep for me, and I probably made a ton of mistakes. The second thing I learned was that audit probably wasn’t, and still isn’t, for me.
I was in audit there, and one of my first clients was a listed fund manager, an infrastructure fund called Hastings Funds Management. I realised pretty early that audit wasn’t what I wanted to do for the next 40 years.
When I first joined, I had this misconception that your first job is basically what you’ll do for the next 40 years and your career is linear. That’s not the case. At that point I realised audit wasn’t for me.
I didn’t wake up every morning saying, “This is what I want to do for the rest of my career.” I wanted something more engaging than retrospective work for clients. I felt like I wanted to build my own thing and do my own thing. My biggest failure wasn’t one event, but learning how to think and communicate in a corporate way while putting clients first. That was a big takeaway for me.
Along the way, I’ve made so many mistakes. I remember one time, with my first client, one of my senior consultants told me to print a few files and documents.
It was probably my first week at PwC. I said, “Okay, fine. I’ll go print some stuff,” and walked into the printer room with these massive corporate printers. I was used to having a normal printer at home and knew how that worked. The senior said, “Print this stuff. It has to be colour, double-sided,” and gave me a whole bunch of instructions. I thought, “Yes, I’ve got this. How hard can it be? Print some papers and I’m done.” I walked into the printer room and was intimidated by this massive thing.
You needed a card to swipe in and use the printer. It was nuts. I spent 45 minutes in the printer room trying to figure out how it worked. I was like, “What am I doing? I can’t print this, and it’s taken me 45 minutes. What is the senior consultant going to think of me?”
“I’m done. This isn’t going to work.” I think she came over thinking, “What is Haynes doing? Why is he taking this long to print a few pieces of paper?” She helped me out in the end. That was a big realisation that there’s so much I don’t know.
I should be open and honest and say, “Look, I don’t know how to do this thing. Can you help me out?” I don’t think I’m the only one in this situation. A lot of grads listening will be thinking, “I’ve got these really dumb, silly questions that I should know the answer to, but I don’t, because I’ve never experienced this before.”
My advice is to suck it up and ask for help. It doesn’t matter how silly it is. That was an interesting experience.
James: Ask those questions early, because when you’re six months into a role and haven’t asked, people assume you know what you’re doing. It becomes even more difficult to ask then, so get them out early.
Haynes: I always encourage people to ask questions upfront and early, because that’s much easier. It’s a better outcome than waiting until the end and saying, “Sorry, I didn’t know this, so I’ve wasted all my time spinning my wheels.”
I advise all my teams and mentees to be upfront and own the areas where they need help, because we were all grads at one point. Think about some of the most inspirational and intimidating folks you might have worked with, and realise that everyone was an intern.
Everyone was a grad. We’ve all been there. We sometimes overthink things, so remove that and be direct in seeking help.
Questions to ask when moving roles#
James: Speaking of questions, you’ve moved around a little bit and found out that audit wasn’t for you. When you’re somewhere you don’t want to be and looking for somewhere else to go, what questions would you ask people to prepare to move into something you might prefer?
Haynes: You don’t really know what something is like unless you’ve experienced it. There are a couple of things you can ask folks in that role or company before you join: what’s the career trajectory like? Is the company growing? What’s the culture like?
Why is this role open? Has someone left? If so, why did they leave? What’s the message? What’s the vision of the key founders and executives? These are investigative questions you can ask to figure out whether something is the right fit for you.
One important thing to remember when interviewing for jobs is that they’re interviewing you as much as you’re interviewing them. Understand the culture. Do folks go out at the end of the week to have dinner, or does everyone do their own thing? Do they appreciate you asking for help, or is it more independent? Is it a big team or a small team? What does career progression look like? Where do people in this role end up in five or 10 years? Those are the questions I’d ask and think about.
Before I joined Airwallex and accepted the role, I was lucky to know a couple of people who already worked there. I reached out and said, “Look, I’m interviewing. What’s the culture like? Do you enjoy working there? What are your hours like?”
You’ll get the HR spiel, but you really want to figure out what’s going on. My advice is to reach out to folks who work there, especially if you have mutual connections on LinkedIn. Understand where the company is growing, where you would end up after five years in the role, and what skills you would have.
Your career is not linear#
Haynes: One thing I’d wrap this with, James, is the context that your career isn’t linear. This touches on what I said previously. When I first started, I thought a career was a linear trajectory.
You go from grad to analyst, senior analyst and manager. I hate to break it to everyone, but it definitely doesn’t work like that. I think of it as a roller-coaster. There are phases where you’ll go in a straight line, but then you might pivot to another company or change roles.
You might change careers, have a family or kids, take some time off, take a couple of steps sideways or skip a couple of steps. The point is that it isn’t linear. I think career counsellors do everyone a disservice by saying, “Okay, this is the job you want, and this is the linear path to get there.”
I don’t think that’s necessarily the case. It’s more about developing your experiences and skill sets. If you want to be an audit partner, it might seem linear, but a lot of folks now work in industry for a couple of years and then come back. If you want to be a CFO, there are different ways to go about it.
You’ve got the banking route, the controller route, the VP route or the FP&A route. Type A personalities who are about to enter the workforce often see things as linear. My strong advice is not to see it that way.
You may have kids at some point, travel, take time off to do your own thing or set up your own business. That’s okay. I was telling my sister this the other day, because she’s applying for grad jobs right now: it isn’t linear.
You’re allowed not to know exactly what you want. It’s okay to try different things, sample different jobs and see what you like and don’t like. I’m a big fan of reaching out to people in the jobs you aspire to get and picking their brains over coffee. Say, “Look, this is why I’m interested in the role.
“I want to understand what your day-to-day is. This is why I think I’d be a good fit, but before I invest my time and some of my career, I want to understand whether this is the right fit for me.” You’ll avoid a whole load of mistakes if you use this coffee-chat approach to understanding what a career is all about. That’s one way to go about it.
Another friend of mine decided to do a master’s. He worked in investment banking and realised he didn’t want to do that long-term. His passion was engineering, so he did a master’s in engineering. During the program he realised, “This is actually what I want to do.”
It validated his interests and passions and confirmed that this was what he wanted to do for the foreseeable future. Now he’s working in data analytics and computer science, and he really enjoys it. Postgraduate study is another option.
Finding Mentors in Australia#
James: You mentioned so much, but the question, “If I get this role, where do I end up? Where have people who previously did this gone?” is a really great one.
What you said about sitting down with people for coffee is also really important. You don’t necessarily have to know them before reaching out. That’s likely something you’ve done too: reaching out to people who work there and with whom, as you said, you might only have mutual connections.
Lots of people will happily sit down with you. Nowadays, you can easily tee up a half-hour call, and most people will slot you into their schedule.
Haynes: It amazes me how little that happens in Australia. Students or young grads reaching out to people and asking for coffee to pick their brains happens surprisingly rarely. In the States, it’s almost a regular thing.
Alumni and other folks reach out to you almost every other day. Here, I don’t think that has caught on yet. The States also has a stronger college alumni culture. If you went to a certain university, you’ll actively reach out and introduce yourself to people who attended it, regardless of where they are now.
That doesn’t really happen in Australia. It might be because there are fewer universities here than in the States, and people don’t have that same—not patriotism, but sense of belonging to their university.
If you’re a young student listening to this and applying to a company where people have mutual connections with you or went to the same university, flick them an email.
The worst case is that they leave you on read and don’t respond. You haven’t lost anything. The best case is that you have a really engaging conversation. Whether they steer you towards the role or away from it, you’ll learn something you probably wouldn’t otherwise have known and potentially save yourself from a mistake.
I strongly advise people to do that.
James: This applies both to reaching out about certain roles you want and to seeking mentorship if you want to improve in your current role. Because it’s so underutilised in Australia, as you said, there’s even more value in it. The people you’re contacting don’t usually receive these approaches, and they’re often more than happy to help.
It’s important to utilise that while it’s still uncommon.
How to reach out to people#
Haynes: I can’t think of a better way to differentiate yourself from the pool of graduates. Graduate crowds probably don’t know this, but when you apply for a job, you’re one of thousands of applicants, and it’s unrealistic for people to go through thousands of applications.
To the extent that you can differentiate yourself, that’s a huge plus. There was a Tim Ferriss podcast about networking and how to approach people. He talked about it more from an entrepreneurial perspective, but I think the principles still apply.
You have to be careful about cold-emailing people and saying, “Can I pick your brain?” Folks are generally busy, and you need to be conscious of their time and calendars. You’ve got to structure the approach. They look for two things.
One is: is this person legitimate? If I say yes, will they take it seriously and show up on time? Do they have a background, whether tertiary or work experience, that validates their interest? That’s number one.
The second is: what is this person looking to get out of it? What do they mean by “pick my brain”? Do they just want a coffee chat and a referral, or do they genuinely have a specific question they want help with?
When cold-reaching out to people, be very clear about what you want to get out of it. You have to be wary of people’s time.
If you’re looking for a referral, say, “Look, I want to learn more about the role and some of its challenges. Then, if you’re happy, can you refer me to someone?” If you have a specific question, let them know. Being efficient is the name of the game.
James: Being genuine is so important, as is being specific with the ask. It’s something I try to do when asking people to come on the podcast, which is a good exercise for this kind of thing: lead with some kind of value or something happening in their life.
Then give some context about why you’re reaching out, and finish with the specific things you want to discuss. It shows that you’ve made an effort to investigate them, what they’re about and what they do.
If you put in little effort and they say yes, they’ve almost set that as the bar for the people they’ll speak to. People don’t want to set it so low that they’ll say yes to anyone who says, “Hey, can I speak to you?” They’ll set it higher and only speak to people who are genuinely interested in what they do.
Haynes: You have to put yourself in their shoes. When you’ve got a tight schedule, you want to make it impactful. The best way to do that is to be clear about your objectives and what you want to get out of it.
Haynes’ Advice for Graduates#
James: I’ve got one last question for you, Haynes. We’ve covered so much in this conversation, but I want to ask the question I ask all the guests. If you were graduating and about to start your grad role next year, what advice, or one piece of advice, would you give yourself?
Haynes: I’d tell myself that it’s important to keep my personal interests and hobbies and not lose them when going into a grad role.
The process of getting a grad job is well documented, and there are enough resources out there. What we don’t talk about is the importance of keeping your personality and hobbies as you join a big company. I’ve seen this so many times: you go through university with all these hobbies, interests and passions, then enter the workforce and it becomes all-consuming.
It’s nine-to-five, but not really nine-to-five. It depends on your role and company, but you’ll be working long hours. Sometimes you’ll work on weekends and miss birthdays and dinners. Looking back, my view is that you want to keep your passions, interests and hobbies with you for as long as you can.
Don’t let your work life take over your whole life, because it’s easy to do. There is always work; there will always be work. But if you’re into sport, the gym, dancing, teaching or mentoring, or have a business—whatever gives you joy and satisfaction—you need to keep that, because there will be times when work isn’t great.
Whether you’ve had a tough week or you’re really stressed, you rely on your personal hobbies and interests to pick you up. For a lot of people, it’s their relationship with their partner, their faith or working out at the gym. The crazier work gets, the more important those parts of your life become in keeping you grounded and sane.
If your work becomes all-encompassing and there’s nothing else, you’ll burn out very quickly. You’ll also look back and realise that all you’ve done is work and you’ve got nothing else to show for it. My advice for all these optimistic 21-year-old grads is: keep your hobbies, interests and passions.
Have work fit around those, rather than making it the only thing you have in life. It also makes you much more interesting and knowledgeable. As you become more senior, relationships become super important in the workplace.
You’ll draw on those experiences—travelling, having a business or working out—to build workplace relationships as you become more senior. That’s something I’d recommend.
Charlie Munger’s Lattice Theory#
Haynes: There are a couple of principles I’d like to cover as well. One of the things that has stuck with me is Charlie Munger’s mental models. I’m a big fan of Charlie Munger.
For folks who don’t know who he is, he’s almost the second in charge at Berkshire, helping out Warren Buffett, and is one of the smartest people you’ll ever meet. He has this interesting mental model called the lattice theory. I think it’s really relevant for grads and folks listening to the show. Lattice theory is about developing niches in one area while also developing experience and skill sets in another, totally unrelated area.
You put those together and find where they overlap. It’s in that overlap where you’ll have a lot of growth. What do I mean by this? It’s a really good case for entrepreneurs as well. If you’re an accountant but also interested in dance and the arts, figure out the overlaps. Can you be a financial adviser for a creative dance company? You’ll find a ton of opportunities in those overlaps. If you’re an engineer but also into design, figure out what overlaps exist between those industries and dive in there.
If you’re a builder but also really into cars, figure out the overlaps and dive into them. I call it the lattice theory. It’s this mental model of figuring out your current skills, interests and passions, while also developing something else that’s totally unrelated.
Develop skills and expertise in that other area. Over time, you’ll find a lot of growth and opportunity in the overlap between those seemingly unrelated areas. A really good example is a YouTuber called Ali Abdaal.
I’m sure you’ve probably heard of him; I feel like a lot of people have. He combines medicine, being a medical student and being an entrepreneur. He’s able to combine these seemingly unrelated things and do so well because there aren’t many people in that space right now.
If you can combine two or three different niches, find the overlapping area and enter that space, you might find that you’re the only person there, and you’ll do really well. I’m not sure if that makes sense, but it’s a mental model that has stuck with me for a while.
James: We’ve spoken about Tim Ferriss a few times today, but I’ve heard him describe that too. There’s a guy called Scott Adams—I don’t know if you’ve heard of him—who talks about stacking skills. As you said, the crossover between things allows you to excel. If you’re a good accountant and a good public speaker, for example, maybe you’re a really good public speaker about accounting.
As soon as you stack two or three of those skills, you can become one of the best few people at that niche thing, because there won’t be many people who are also good at that combination.
Haynes: I always give this advice to my creative friends, whether they’re musicians or chefs. If you can find another skill set in which you don’t have to be an expert, but are remotely proficient, see where the overlaps are and whether you can be in that overlapping space. There aren’t many people there, and you’ll find a lot of opportunities. I encourage grads to think about that too.
The Fancy Title Career Mistake#
Haynes: The other point I wanted to discuss is the misconception I often see about working for fancy companies and having fancy titles.
It’s natural for folks to want to work for large, prestigious companies with fancy titles. My advice is to do a 180 and veer away from that. You’re better off working for really competent managers and inspirational people than for the biggest consulting company, where you’re a small cog in a bigger ecosystem.
That’s not to say you won’t learn anything by joining the big banks or consulting companies. You’ll get a fantastic grounding in how businesses work.
But if I’m an intern or about to start my first grad job, I’d place more emphasis on the person I’m working for, the role, and the skills and experience I’ll gain than on the name on my CV. I’m part of the Earlywork community, a Slack group of Aussie founders and people working in startup companies. Most people haven’t heard of many of those companies.
If you work at one of these startups and go to a dinner party saying, “I’m head of growth at this startup,” no one is going to know what the company is. That’s okay. You’re learning a lot and building all these skills. As a grad early in your career, you’re better off learning as much as possible and being challenged in as many ways as possible.
In my view, that is better than working in a large company where you’re doing the same thing repeatedly. It might sound great on your CV, but I’m a big believer in developing your skills and having really interesting experiences. You generally get that in smaller companies and startups, where you’re working on a million things at once.
You might be a software engineer, but at a startup with 10 people you’re also helping with product design and go-to-market strategy. You’re wearing multiple hats, and that’s where you get a lot of growth.
When I joined Airwallex, we were a Series C company. I joined as a finance manager, but did a whole bunch of work on tax, go-to-market, audit, financial control, budgeting and FP&A—things you wouldn’t necessarily see at a bigger company.
At a bigger company, you’d have one person looking at each of those things individually. Connected to that, find someone who inspires you and work for them. If you want to enter a particular profession and there’s someone who’s absolutely killing it, is super competent and whom you admire and respect, reach out and say, “Look, can I shadow you for a week? Can I work in your team?”
See if you can make that happen. I feel strongly that folks should stay clear of working at a company just for the name on their CV, and instead work there for the skills and experiences they’ll develop along the way.
James: I’ve spoken to people on the podcast about generalisation and specialisation before. From what I’ve read online and in forums, a lot of people who become successful have a general background and then become almost a generalised specialist. They start as a generalist and become a specialist in one area while remaining quite broad.
Haynes: The mental model for this is, I think, called the T theory. You want to be broad as a generalist, but specialise by going deep in one area. Touching on what we said earlier, if you can go deep in one or two areas and find where they overlap, you’ll have opportunities that not many people have.
Not many people are in those overlapping areas. That’s something that has worked well for me, and I hope I can encourage people to do something similar.
Outro#
James: The things we’ve spoken about today—mentoring, mental models, generalisation, going overseas, seeking opportunities and finding the right boss—are fundamental for grads to know as they begin their careers. They can save you a lot of time and headaches if you’re conscious of them and apply them early, helping you get on the right path as you begin your career.
There’s so much value here. Haynes, thanks so much for coming on the podcast today.
Haynes: No worries, James. This was great. If anyone has any questions, feel free to shoot me a LinkedIn DM or find me at [email protected]. Eighty-seven is the number 87; it’s the name of my advisory business. Feel free to reach out.
I’m always happy to help.
James: Great. We’ll have links to all Haynes’s stuff, his contact details and everything in the show notes. Thanks so much again, Haynes, for coming on. We’ll see you around.
Haynes: Awesome. Thanks, James. Talk to you soon.
James: Thanks so much for listening to that episode with Haynes D’Souza. He’s so passionate about graduates and graduate careers. We covered so much in that episode, and so many little nuggets can make a big difference in your life and career.
If you want to find out more about Haynes, follow the links in the description. If you want to find out more about this episode and see my takeaways, go to GraduateTheory.com and find the link to this episode. The link will also be in the show notes. If you want to get this information and my takeaways from different episodes straight to your inbox, please consider subscribing to the newsletter.
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Thanks so much again for listening today. And I look forward to seeing you in the next episode.