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.
Nan Meka#
Nan: I think that, as somebody entering a startup, you might get enamoured with the size of its fundraising. Having been in a startup, however, I know that fundraising is not an indication of successful product–market fit, a successful commercial model or a great customer experience, so it is one metric I definitely ignore.
James: It’s great to have you on the show. I want to start by asking about your corporate background.
Transitioning from Corporate to Startups#
James: You worked at KPMG, Macquarie and a bunch of other really corporate places, and now you’ve been in startup land for a little while. What led you out of the corporate world and into the startup scene? Was there a particular moment that triggered that transition?
Nan: Earlier in my career, I was on the other side: I was assessing and investing in internet businesses. I was also in the gaming space, developing commercial models and supporting digital businesses with their strategies. I spent most of my earlier career in the consumer tech space, particularly on the corporate VC side, in strategy and M&A, as well as on the early-stage startup and scale-up company side in the last year.
As a non-technical person, I really didn’t think there was a pathway for me into early-stage startups, especially with my random background. I found that was the furthest thing from the truth because there was pent-up demand for malleable generalists who learn fast, solve problems, help scale the business and create defensibility against the internal and external shocks that an early-stage business constantly experiences throughout its journey.
The startup ecosystem wasn’t so big back in the day—and I don’t really want to show my age right now. I think Blackbird VC was only just coming to fruition around that time, so it was a very nascent period for early-stage investing in Australia. There wasn’t much of a community or many meet-ups in this space. I basically had to reach out to founders I admired and identify problems they were solving that deeply interested me.
I’m not going to lie: it was hard to make that leap from a very structured, well-resourced environment to one that was grey, ambiguous, chaotic and all of the above. Luckily, I got my first foray into startups about seven years ago when I joined a little online bus-booking business. It ended up scaling to about $200 million in gross sales a year and helping millions of customers travel more easily.
I worked in an area called business operations. What is business operations? The purpose of my team was to drive the growth of the business by launching and scaling new initiatives, optimising day-to-day operations or doing a mixture of both. I was fortunate enough to work on many different problems across product, marketing and customer success, ensuring that the business was solving the right problems in line with company-level objectives.
For example, we had a backlog of customer queries, so we asked how we could improve the customer experience. That’s deeply important in the online travel space: you need the ability to connect with somebody in real time and have your query answered because you’re about to miss your bus, which will affect your journey and experience. I looked at streamlining processes to handle those queries and at ways to improve metrics such as NPS. I also worked with marketing to launch loyalty programs and improve retention rates.
There was a variety of work. I wasn’t an expert in anything, but I was deeply curious about how things worked and had a very growth-oriented, learning mindset, like a baby just coming into the world.
More recently, I was the Head of Operations at Simply Wall St, a B2C SaaS app that has helped more than five million retail investors make better stock decisions. I don’t know if you’ve used it.
James: I have. I had a little bit of a play around with it in the lead-up to this interview, but not before then.
Nan: It’s great, isn’t it? I’m not attracted to just any startup, but to a startup that’s solving a business problem—or any problem—that hits a personal note with me. I was already a Simply Wall St user because it helped me on my personal retail-investing journey. There was a lot of asymmetric information. I didn’t have access to a clunky Bloomberg terminal, which was prohibitively expensive. I believe they were about $150,000 per terminal or licence—something crazy like that—which a hedge fund or large company would have. As a result, I didn’t have the same level playing field.
I saw a business and a founder, Al, who were deeply passionate about that space. He was levelling access and simplifying the journey for the average Jane or Joe. That’s what attracted me to the business.
I’m now a VP in the finance team at Pet Circle, which is obviously a leading online pet company in Australia. It was a tough decision to leave Simply Wall St because I went from an early-stage startup solving super-interesting problems to a business doing exactly the same thing, but further along in its scale-up journey.
The decision came down to my skill set. I wanted to level up, expand my toolkit and join a company during that journey. I fell in love with the founders’ stories and their ambition to build a great, enduring business that aims to meet all our furry and scaly friends’ needs. Hearing that vision from Mike, our CEO, and our CFO during the interview process—and hearing their excitement—really drew me in.
My team and I help the business make the best decisions possible. We enable business leaders to make the right choices for the customer and the company; support and optimise existing business lines; help the business plan better; and look at new growth opportunities, such as entering new markets or adjacent businesses in the pet space.
James: That’s super cool. Thank you so much for sharing it. You’ve done some really cool things in your career, and it’s great to hear some of the details of what you do day to day.
I want to ask about one thing in more detail. You touched on attachment to the mission and how a startup relates to your current skills, but if someone is looking to make the leap as you did, what should they look for when joining a startup?
Finding a good startup#
James: If you could run the clock back, what would you look for now that might increase the odds of it being a good experience?
Nan: That’s a great question. I’ve started doing this much more: interviewing the startup or business that’s interviewing me. People should spend the vast majority of their time figuring out whether this is the right company for them to join, above anything else. It needs to be aligned; otherwise, you’re not going to be excited about coming to work every day, especially when things get difficult.
I would ask certain questions before joining a startup. You can do some desktop research, but you should test the rigour of the business model in particular. Is it a big market? What does the team look like? Are they strong executors? Is the team diverse? Are they creative? Are they good operators? Diversity is super-important.
In my experience, I’ve optimised for companies operating in really big, growing markets. Online travel is huge. Pets are a $15 billion market in Australia alone. In the retail-investing market that Simply Wall St is tackling, there are about 300 or 400 million retail investors worldwide. Those are huge, growing markets. More people are entering them, taking note of them and paying for services and goods in them.
I also try to get a sense of how the product was doing before it launched. Before an interview, I do the desktop research I mentioned and dive into customer feedback, whether on Trustpilot or in Google reviews. That gives me a sense of whether the feedback shows that the product is solving a real customer pain point, or whether a problem has been invented because it sounds cool but doesn’t make for a sustainable business.
Another thing I’ve noticed that drives me crazy is the amount of marketing around fundraising. As somebody entering a startup, you might get enamoured with the size of its fundraising. Having been in a startup, however, I know that fundraising is not an indication of successful product–market fit, a successful commercial model or a great customer experience, so it is one metric I definitely ignore.
You see many companies saying, “Wow, we’ve raised $100 million. We’ve raised $150 million.” Then you see them in the news saying, “We haven’t met our revenue targets or some of the other metrics we planned to hit, so we’re letting go of 15 to 20 per cent of the workforce.” This is happening a lot now. Even yesterday, I saw a local news story about a company letting go of 16 per cent of its workforce after it had just raised $125 million in a round led by the Atlassian founders. It’s important to distinguish fundraising from business success.
There may be little or no information because startups are private companies. By the time I get to the interview, I ask my interviewers point-blank about these topics. I’ve asked, “What are your actual challenges? Is activation the issue? Is it acquiring customers? Is it retaining customers?” I really dig into whatever information they can give me. If they try to gloss over it, I think something is suspect. It’s important to dig into that information and not be afraid. Just because they’re interviewing you doesn’t mean you can’t interview them back. It’s a two-way process.
I’ve been an angel investor, and I’m also an operator in startups and scale-ups. I focus most of my attention on the founding and executive team because, in early-stage businesses, revenue and certain other metrics might not be ascertainable. I tend to look at whether the founders are the right people to build the product in this market. Are they customers themselves? Do they know the customer well, or are they just doing it for bragging rights?
Do they have passion that can be sustained for decades? Building a startup is tiring; there are more bad days than good days. You’ve got to have great, big, bold ambitions to change the world and help the customer. The founders can’t just optimise for the financial return and think, “I’m going to be a multimillionaire out of this.” They must deeply love what they’re doing. Do they care beyond the product? Do they care about people and about building a generational business that will transcend time and have long-lasting impacts for its customers? That’s important to distil.
One red flag is if they cover up the challenges and problems I’ve mentioned. I would counter by asking, “What area of the business do you think you can improve?” Look at whether their response shows humility, real ownership of the problems and an acknowledgement that there’s work to do. That shows they’re grounded in reality and understand that everyone needs to come together to solve those problems, instead of glossing over them until everything blows up.
Finally, is this a team I can and want to learn from? Even though a founder or CEO has different skills from you, there are important meta-skills beyond the technical and other hard skills. You can learn just by observing how they communicate, prioritise and handle stress. That’s incredibly powerful. You don’t want to feel like the smartest person in the room when you’re with the team or its founders. If you are, you’re not going to learn anything, so I would avoid businesses like that as well.
James: That’s really great. As you said, if a company is going well and has things to share, its people will be more open to sharing them. If things aren’t going well, perhaps they won’t be. Even without getting a direct response, you can still get an idea of what’s happening.
There are many useful suggestions there that I hadn’t considered, such as looking up reviews to see what people actually think. Your point about funding is also interesting because there is so much media coverage of capital raises. It’s easy to think, “They raised lots of money, so they must be a good company,” and disregard the things you mentioned: are customers having a good experience with this product, and are the founders going to stay in it for the long haul? I like that a lot. I’m definitely going to use some of those tips.
Nan: And if all else fails, watch a lot of true crime. You get really good at investigating.
James: That’s amazing. You mentioned wanting to be in a team that will help you grow, learn and develop, where you don’t feel like the smartest person in the room. I feel this is something you do really well. You’ve done plenty of learning outside work.
Learning and Career Progression#
James: You completed a Master of Finance and different VC programs, including a few almost bootcamp-style training programs. How do you think about developing your skills, both in and outside your role? How have you used those external programs, as well as your current roles, to progress?
Nan: University can only teach you so much. The real lessons start when you enter the workforce and begin interacting with customers, different functions and your team. It’s about being open, deeply curious and understanding why we do what we do.
If there’s any skill I would suggest cultivating, it’s curiosity. It encourages learning and the exchange of ideas. It helps us communicate better with one another in our teams, builds deeper connection and empathy for what a teammate or another function is doing, and fuels innovation. When we’re curious, we look at tough problems more creatively and sit with them until we deeply understand why they’re so challenging.
In my case, I wanted to learn more about product management and growth. At Simply Wall St, for example, I interacted a lot with the people developing those strategies and building those teams, but I didn’t have any depth of understanding beyond what I’d read online. I didn’t want that superficial understanding, so I invested much more time in learning from others. I set up coffee catch-ups with people to understand what they do, why it has an impact on the business and why it’s so important, and asked them to break it down for me.
I also invested my own time after hours in training. I started doing Reforge courses, which are a great way to deepen your understanding of product and growth. I learnt how product managers do their jobs, how strategies are set at that level and even how they interview their users. From a growth perspective, I learnt how to build a growth model in a tech business and think about pricing and monetisation. These are some of the many elements that make up growth, which is deeply complicated because it’s a newer area and very different from traditional marketing channels.
For me, it was about investing a lot of time in levelling up: reading, subscribing to newsletters and following people on Twitter to learn. I was deeply curious and wanted to understand why things worked—not because I wanted to do those jobs, but because it helped me build greater empathy and understanding. I was on the leadership team, supporting these teams in growing, building and defining strategies. I needed that understanding; otherwise, I would add no value.
James: It’s interesting that you mentioned aligning the startup or company you join with a personal pain point, something you’re interested in or a product you already use. That really helps with curiosity. If it addresses one of your pain points, you’re interested in it and you also work there, you’re much more likely to stay interested than if your pain points and workplace are completely unrelated. You have better odds of being interested if you work somewhere relevant to you. One hundred per cent.
Mistakes young people make#
James: Let’s continue. We only have a little time left, so I want to touch on your career more broadly rather than on the day-to-day, and ask for some career advice. I’m sure you’ve seen many junior marketers, growth people, product people and others come through the companies where you’ve worked. What mistakes do you see them make? Is there anything you wish you could tell everyone starting their career not to do?
Nan: I’ve often received the same career advice from parents or, respectfully, older people: “You’ve got to know your worth when going for a role.” When they talk about worth, they mean your compensation—your total compensation. I understand that it comes from a good place and is about ensuring that you and others value your time.
The biggest mistake I see people make, however, especially when moving from a corporate job into a startup or scale-up, is trying to optimise their salary. Early in your career, you should definitely optimise for learning over earning a high salary, and over the role title as well. I strongly believe that if you invest in learning first, you’ll develop a highly sought-after skill set. That translates into a valuable role, with a high salary ultimately being a by-product.
In my experience recruiting and interviewing candidates, this comes up at the offer stage, especially with people who have two to four years’ experience and have come from large corporates. They think they should therefore be earning even more. They may want another $5,000 to $10,000, which is totally immaterial after tax, or they want a particular title in a startup because the role they’re going for isn’t sexy enough.
It’s all immaterial because you’re forgoing a valuable, steep learning curve; the immense amount of ownership you get from day one; and the conviction you build in yourself through repeated opportunities to be tested, fail, learn, pick yourself up and become stronger. You don’t get those opportunities at a larger organisation because there’s so much cushioning and protection.
I would caution people to think carefully about why they’re going for a startup role and not optimise for earnings. Startups and scale-ups are resource-constrained, so the money might not be in the budget. You might miss an opportunity you can’t get back—one that many people are vying to get into.
James: Today, startups are the new sexy thing to do, so people want a nice title and things like that. I completely agree that learning is particularly important when you’re young. As you said, the learning and knowledge you gain will lead to a high salary sometime in the future; you don’t necessarily need it right now. In fact, choosing a high salary when you’re young might limit your growth in some cases, where you’re being overpaid to do nothing. It’s important for people to recognise that.
Nan’s Advice for Graduates#
James: Let’s do one more. This is a question I ask all our guests: Nan, if you could rewind the clock to when you were just graduating from university and heading out into the world, knowing everything you know now, is there anything you would do differently? Is there any advice you wish you’d known then?
Nan: I’ve definitely put my foot in it a lot and made many mistakes, and I’m really grateful for that. Don’t shy away from failure—absolutely not. Having said that, you can at least mitigate its impact. Being hit constantly can be very demoralising to your confidence, and it often takes time to pick yourself up. You need to realise that things aren’t personal; this is just the way of the world. You don’t have the cushioning and protection of university any more.
I wish I’d developed greater self-awareness about my behaviours, what I’m really good at and what I’m terrible at. I wish I’d been more open-minded about unlearning the behaviours that held me back from growing. Sometimes that can be humbling and take you a few steps back, but I think that’s okay.
The way university is set up, and the way society pits people against one another through competition, gets into your head and makes you want to keep moving forward. I wish I’d taken a step back to address some of those areas.
For example, one thing I struggled with was going from being a strong individual contributor to a people leader. It’s a completely different job, requiring new abilities and a totally new set of problems, muscles, skills and tools. I had to make significant changes. Instead of going deep into my work, being myopic and becoming very good at executing tasks or building a particular skill set, I had to look at the bigger picture and understand and communicate the context in which the team operates.
I went from being a master of my craft to training others to be good at their jobs, because that’s when you’re successful: when you’ve been able to help others. I went from solving problems with the tools and resources I had to allocating resources and influencing others, which became more important in this role. I had to move from a functional mindset—thinking about my function and what’s required to do the job really well—to a company mindset focused on what’s good for the business.
You often have to unlearn many things. It takes time because you’re like a computer: you’re programmed a certain way by society, external factors and internal drivers. I sought a lot of help, both externally and internally. I wasn’t afraid to tell people, “I don’t know how to do this, and I need to get better at it. How do I do that?” Some people might see that vulnerability as weakness, but it isn’t. It’s so powerful to be vulnerable because a weight lifts off you. You think, “Great, I can learn without any judgement,” and they’re probably thinking exactly the same thing.
I think you should focus on unlearning and becoming more self-aware—on your internal engineering and make-up. Spend much more time knowing yourself than knowing the external business; that can come second. I wish I’d done much more of that. I wish I’d worked out what actually motivated me, rather than what my parents wanted me to do.
When you graduate, everyone goes into an investment bank, a Big Four firm or a consulting firm, and that’s treated as a mark of success when it really isn’t. There are alternative career paths. Because I’d been so conditioned, I thought success only came through that path. It didn’t bring me any joy, and that’s probably why I changed so many times: I became deeply frustrated but hadn’t spent enough time asking myself why.
I didn’t spend enough time getting to know myself, my creative side or the problems I’m drawn to. Now I’m freer, more open and very honest about it because I don’t want to keep switching. I want to solve a problem I’m deeply passionate about and love working on day in, day out.
James: That’s so important. It’s great to see you go on that self-development journey, learning more about yourself and building self-awareness. I completely agree. We’re all somewhere, trying to chase something. It’s cool that you can look back now and see how far you’ve come. You’re doing some really amazing things, and we’re very fortunate to be able to hear your wisdom. Thank you so much for sharing it with us.
We might wrap it up there. Before we head off, where can people find out more about you and connect with you after listening? Is there anywhere you’d like to send them?
Nan: I’m on Twitter and Instagram, but that’s more for my travel and food photos. I’m also on LinkedIn, so do connect with me there. I’m always happy to connect with people, including at startup meets. I’m deeply passionate about the community and investing, so if you want career advice—I don’t know why you’d come to me—or want to hear about my mistakes or war stories, I’m happy to share them. LinkedIn is the best place to catch me.
James: Thank you so much again for coming on the show, Nan. It’s been really interesting and insightful to hear your thoughts and your journey. Thank you for sharing it with us, and we’ll catch you around.
Nan: Thanks, James, for the insightful questions. I feel like Baby Yoda.
James: Thanks for listening to this episode. I hope you enjoyed it as much as I did. If you want my takeaways—the things I learnt from this episode—please go to graduatetheory.com and subscribe. You can get my takeaways and all the information about each episode straight to your inbox. Thanks so much for listening today, and we look forward to seeing you next week.