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.
James: Hello, and welcome to Graduate Theory. Today’s episode covers the importance of personal branding, the advantages and disadvantages of working at an established corporation versus a startup, and how to find jobs without waiting for permission. It’s one of the best conversations on Graduate Theory. Please enjoy.
Intro#
James: Hello, and welcome to Graduate Theory. My guest today is a computer science and marketing graduate from the University of New South Wales. He’s worked in marketing, consulting, design, sales and operations at companies including Amazon, Uber, Deloitte and IBM, as well as several startups. He is currently a product manager at Atlassian. Alongside this, he is a co-founder and chief meme officer at Earlywork, which now has an audience of over two and a half thousand people. It has been featured by the Australian Financial Review, Startup Daily and SmartCompany. He’s part of the angel-investing program at AirTree Ventures, an angel investor himself and an adviser at 98, a cross-continent Gen Z marketing agency.
Please welcome to the show, Dan Brockwell.
Dan: James, mate, thank you so much. I think we’re going to have some fun today.
James: Absolutely. There is so much I want to discuss with you, Dan.
Personal Brands in 2022#
James: Personal branding is constantly evolving. How important is an online personal brand in 2022?
Dan: I would modify the question slightly: a personal brand for whom? Are you a startup founder, job seeker or investor, and what do you want to use it for? A personal brand can serve very different purposes. It may be career-related, or it may support your work as a musician or artist outside your career. Only recently in human history has it become possible to write something once and let many people see it so easily.
An online personal brand lets you share your story much more scalably: you do the work once, then many people learn who you are. There’s an old expression, “It’s not what you know, it’s who you know.” The modifying factor is actually who knows you.
The further refinement is: who knows you for what? An online personal brand gives you more shots on goal. You may be a poor striker in football, but if more people learn what you do, enough shots will eventually produce some goals.
James: Online technology also makes the marginal cost of distribution effectively zero. Sending a newsletter to ten people costs the same as sending it to a thousand or a million, so there is almost no limit to the number of people a personal brand can reach.
Dan: Absolutely. Naval Ravikant, the founder of AngelList, describes code and media as two highly scalable forms of leverage. You can write software once and scale it to millions of people, or create content once and do the same. A third example is law: legislation is written once and can affect millions for a long time. But changing the law requires far more permission and hierarchy than creating code or content. Today, young people can build online careers by writing content and software without waiting for anybody’s permission.
James: That’s powerful. You have built a substantial personal brand.
How Would Dan Start a Personal Brand in 2022#
James: If you began again today, how would you decide what to discuss and where to publish it?
Dan: Think about content and context: what to say and where to put it. I have no regrets, but I wish I had begun documenting what I learned when I entered the technology and startup world during my first year at university. My first proper university job was at a startup. Sharing that early journey with friends—many of whom did not know that world existed—would have been fun.
You can be young and inexperienced while still knowing more about a particular subject than many others. Everybody has a unique journey. You do not need to be the best in the world; you may simply know much more than your friends about something, such as running a podcast, and can begin documenting it.
In terms of format, I would experiment more with video. I have favoured text because it offers a strong return on effort: beyond the writing itself, production requires little work, yet it scales widely. Video is deep, engaging and human. We will explore that opportunity with Earlywork through Earlytalk on TikTok.
Choose subjects that genuinely interest you and that you are already learning about. Most people read about hobbies, passions and other fascinations in their spare time. The best content comes from authentic curiosity combined with an experience that other people may not share. The magic lies at the intersection of your distinctive experiences—perhaps knowledge about creating a podcast—and the subjects that naturally draw your curiosity.
I also see content as a tool. If you create something for others, ask what need or problem it addresses. Content should be actionable: somebody should be able to read a newsletter or hear a podcast and apply its ideas directly in the following week. Your content may begin by solving your own problem, then reveal that others share it.
James: I think it’s powerful regardless of age. Your point about video was interesting too. Keeping up with all the different media landscapes can be tricky, but video is particularly exciting. I think TikTok may now receive more searches than Google.
Dan: More mobile searches.
James: That’s incredible.
How to convert your personal brand into opportunities#
Dan: It has grown enormously.
James: Suppose you have started building a personal brand through Substack, Twitter or another platform because you want to market yourself and attract opportunities. How do you convert that brand into tangible opportunities?
Dan: My thesis with Earlywork was to build the customer before the product. A brand creates an audience. When you curate an audience around a niche interest, it becomes valuable both to its members and to others. As your personal brand and audience grow, ask what the audience has in common, which problems its members share and how you can solve them.
Earlywork began as a Substack newsletter. In September 2020, I started curating technology and startup internships and graduate roles for ten friends in Sydney. It grew to roughly 600 subscribers, perhaps approaching a thousand, before I launched a community around the newsletter with my co-founder, John.
The content was gaining traction and people enjoyed reading it. We had a small LinkedIn group of highly engaged users, whom we supported closely in exchange for feedback and suggestions. I began to see that young Australians interested in technology and startups lacked a strong social fabric. The content therefore evolved into a community. A one-way conversation, in which we distributed free information, became a two-way dialogue: we spoke with our audience, and its members spoke with us and one another.
James: That’s a great example of turning content into a real community. Once an audience reaches critical mass, shared problems and desires become visible, making it clearer how to serve its members.
Dan: Exactly. If you started a newsletter about tricycles, reached 10,000 subscribers and achieved a 40 per cent open rate, a tricycle company would gladly sponsor it. Tricycles are not my primary focus, but any audience built around a strong niche interest will attract people on the other side who can provide something relevant. By curating that audience, you can connect parties with complementary wants and create a system that helps both obtain what they need.
James: That’s powerful, and I love what Earlywork is doing. From high school through university, I looked for other people who wanted to do interesting work and make an impact. Earlywork has found at least 2,500 people with a similar outlook and brought them together in one place. It’s fantastic.
Startups and Corporate Comparison#
James: I want to talk more about startups in Australia. At university, many people aim to get good grades, secure a good job and join a successful large company. What would you say to someone considering that path and wondering whether a startup might be better?
Dan: This is an interesting choice for a first full-time job after a couple of internships. I do not want to prescribe one answer because it will differ between people. I have moved from startups to corporations, back to startups, then into a corporation again while building a startup. I can describe the patterns I have noticed.
The first startup advantage is breadth of learning. The smaller the company, the broader your role and the more hats you wear. When you’re young, exploring many types of work can be valuable. At Offload, a logistics startup, I handled recruitment, market research, customer success, graphic design, copywriting, email marketing, analytics and legal work under the title of operations—which could mean almost anything.
Second, startups tend to move faster because they have fewer approval systems and layers of hierarchy. You can create and release things to customers sooner, learn more quickly and grow faster. That velocity of learning is extremely important for a young graduate.
Third, startups tend to offer greater autonomy and ownership, although exceptions exist. A junior employee might own the entire marketing function. That responsibility creates room to experiment, make mistakes and learn from them.
Fourth, startups are more likely—though not guaranteed—to address genuinely unsolved problems rather than refine a solution and customer base that already work. I find unsolved problems tremendously enjoyable.
Finally, many startups offer equity. Not every company becomes Uber, but owning part of the business gives you skin in the game: as you help it grow, your holding grows too. An eventual initial public offering or acquisition could create a significant opportunity, although an early-stage company’s future is very difficult to predict.
I love startups and have enjoyed them, but large companies offer their own advantages. People should consider both sets of benefits in light of their career stage.
The first corporate advantage is brand equity. Fairly or not, people use brands as a proxy for competence. You should not spend your life at famous organisations simply to display their names, but early in your career, experience at Google or Facebook provides a stamp of approval. People know you passed the interview process and learned how that company operates. Large companies survived and grew because they did certain things well, so you absorb their processes. I have learned excellent tools from Atlassian, Uber and Amazon. You can also acquire brand equity through internships without committing to a graduate role at the same company.
Second, large companies generally provide more structured learning and mentorship. At Atlassian, I have a mentor, an associate product manager program guide and a manager. The company offers sessions with senior product leaders and external startup founders, along with asynchronous video courses. Large organisations have had time to build extensive libraries, talent pools and structured learning resources.
Some startups also let you work directly with founders and receive substantial mentorship. Structure may be overrated; mentorship is the crucial element, and young people with suitable tools and resources can teach themselves.
Large companies also place you in a broad talent pool of intelligent people who may later become your investors, co-founders, employees or managers. Atlassian has many excellent product managers. I can speak with them, observe how they work and think, and absorb valuable lessons.
The counterpart to a startup’s unsolved problems, autonomy and ownership is a large company’s scale. You may work on a product used by millions or even billions of people, such as Google Maps.
Writing code once and improving a task in millions of lives creates immediate impact that startups may take years to reach.
Mature technology companies also tend to pay higher salaries. Early-stage startups usually pay somewhat less, although growth-stage companies can compete with large technology firms. Established software companies often make substantial revenue at a low marginal cost and can afford high compensation to retain people.
The final consideration is safety. I mean job safety, not career safety. A role at Atlassian, Amazon or Google is less likely to disappear, while a startup could collapse within six or eighteen months. But job risk and career risk are different. Joining a company that fails after a year or two may still benefit your career because you held significant responsibility, learned rapidly and delivered measurable impact. If your financial circumstances are difficult, however, a large company may be the safer choice.
Ultimately, the decision depends on the problems you want to solve, the skills you want to develop, the environment you prefer and your career goals.
James: That was a balanced view of both environments. Through Earlywork and my growing awareness of Australia’s startup ecosystem, I’ve seen that people may undervalue the experience smaller startups can offer. Many graduates move directly towards large, secure companies, but startups can also provide excellent opportunities.
Dan: Exactly. People often want to join Google or Microsoft to learn from experienced, highly skilled colleagues, but those people do not always remain at large companies; many join startups. At a company such as Eucalyptus or Dovetail, you may receive mentorship from people who developed their skills and processes at major organisations. A growth-stage or breakout startup can therefore offer a sweet spot: a fast-paced environment with high ownership and mentorship from top-company alumni.
James: That’s a great point.
Dan’s Thought Process behind going from Corporate to Startups#
James: You interned at several large companies before moving into startups. What was your thought process? Many listeners hold relatively safe corporate roles and may see a startup as risky. What helped you and others make that transition?
Dan: I was fortunate that my first university role was at a startup. It began with a cold email and an ambassador program, which led to a job. Two months later, the company was acquired by Airbnb and I lost that job. I thought it was exciting and joined another startup, so I gained exposure early.
Young people who think seriously about their careers, go the extra mile and pursue side projects are already ahead through their effort and care. If you’re deciding whether to leave a large company for a startup, first ask which problems you genuinely care about. What matters enough that you think about it over breakfast on the weekend? Do not join merely because the company might become large and make you wealthy.
Startups can be difficult, and their hours vary, so I will not generalise. Identify the problems you want to solve and the Australian companies addressing them. Review the portfolios of leading venture capital firms such as Blackbird, AirTree, Square Peg and Folklore, then investigate the companies operating in problem spaces you care about.
Next, consider learning: what will you learn, and how quickly? Do you want technical or design skills, a broad strategic perspective, or product-management experience? Be intentional about the skills you want and ask whether that environment will teach them.
Finally, consider camaraderie. Look at the team, culture and manager. Do you want to spend substantial time with these people and become more like them? If you leave a corporation for a startup, join a strong team addressing a market you genuinely care about with a product that has a credible, differentiated way to solve the problem.
James: Those are valuable questions to ask during the process. Good questions help you reach better answers, while trusting your instincts can also be useful. If a company or field does not feel right, that may be a signal to investigate other opportunities.
Dan: Trusting my instincts was something I struggled with throughout university. When I received a job offer, I would write an extensive list explaining why it was good or bad. Emotionally, I often already knew I did not want the role, yet I would conduct an excessive analysis and speak with 20 people. I naturally overanalyse.
Learning when to trust your instincts is important, but you should still collect data. Speak with people in positions you would like to occupy and gather advice from varied sources. Give greater weight to people doing the work that interests you and holding the kinds of roles you want.
Then return to your values, what you truly care about and your gut feeling. Usually, the right answer will be within you.
James: That’s important: don’t simply trust your gut without information.
Dan: Gather the information.
James: Then make the important choice yourself.
Dan: Exactly. You may collect information and reject most of it, but you have completed the due diligence. We all have blind spots and biases, and sometimes we simply make poor judgements. A second opinion is valuable. At times, my instincts have told me to proceed, only for other people to identify something I had not considered. Seek advice, but you do not have to accept it.
James: That’s true.
Getting Jobs without a job opening#
James: You mentioned reaching out to a company and creating a job opportunity. Few people do this, although many employees tell me it is a good idea. Instead of waiting for a listing and competing with thousands of applicants, you contact and meet people at a company you admire. What has your experience been with this unconventional approach?
Dan: Job listings are only the tip of the labour-market iceberg. People apply to the visible roles and hope for the best, but startups are constantly growing, raising money and hiring. Referrals, informal introductions and other hidden opportunities fill many roles. Startups value proactive people, so do not wait for a job listing—create one.
I worked at three startups during university. The first was Tilt, a social-payments startup. Some friends and I had been conceptualising an app called Friends with Deficits to track debts between friends in different currencies. Competitive research led me to Tilt, which had already solved the problem. I discovered its ambassador program and emailed the Australian country manager to ask whether I could join. After a few months as an ambassador, I converted the opportunity into a growth internship and led a program involving several hundred students across Australia.
That opportunity came from two things: a proactive cold email and participation in something related to the company before holding a formal role. An ambassador program is one route, but you might join a beta-testing group, conduct user research or promote the company. You can become affiliated with an organisation before becoming an employee.
My second internship was with a restaurant-ordering startup whose app let diners order from their phones, similar to me&u or Mr Yum. Before launch, I saw its Facebook advertisement for a referral competition, shared it across university discussion groups and reached the top ten referrers within about 24 hours. I then messaged a founder or operating executive on LinkedIn, explained my interest in the problem and the promotion I had already done, and asked whether they were open to a marketing intern. We met once at Westfield Bondi Junction, and I worked with the company for about six months.
Cold LinkedIn messages are powerful. Structure them around “who, why and what”: who you are, why you are contacting this person and what is in it for them. Explain, for example, that you are studying a particular subject and interning somewhere relevant; describe what you admire about their work; and ask whether they are open to an intern. Do not ask only whether they are currently advertising one. People without a listing may still be open to a conversation.
It also helps to create value before making contact. I had already promoted the app, demonstrating that I would act without waiting for instructions and find ways to help the company.
The third example was Offload, an Australian road-freight logistics startup advertising a full-time operations role. I was working at Amazon, developing my interest in logistics and wanting to return to startups. I could not work full-time, but I applied and messaged the chief operating officer. I explained my Amazon and Uber background, my interest in logistics and the fact that I was completing university, then asked whether the company would consider somebody part-time. After several interviews, it agreed. The role began part-time and later became full-time. I worked there for about six months and loved it.
The lesson is that a job description may only approximate what a company needs. If it requests two years of experience, apply anyway. If it says full-time and you want part-time, apply anyway. Do not eliminate yourself; have the conversation. If the company likes you, it may create space. If it genuinely needs somebody full-time, that is also fine and is not a personal rejection. As you speak with more companies, you will discover and create opportunities that did not seem to exist.
Cold LinkedIn messages to startup founders and hiring managers are powerful, but there are other ways to stand out. Send a video résumé or pitch—perhaps through Loom—to add a personal dimension. Seek referrals, offer feedback on the company’s app, redesign its website, rewrite its copy or show how you would improve the product. You might write an article analysing how a company such as Eucalyptus grew through Instagram marketing. There are many ways to go beyond a résumé and cover letter. If you want to be a candidate pool of one rather than one of 500, do something different.
James: Combining those tactics with the personal brand we discussed earlier can be extremely powerful when applying for jobs.
Dan: A personal brand creates luck. I have been lucky many times, and much of my career success has depended on it, but a personal brand amplifies the number of fortunate opportunities that appear.
I was active on LinkedIn as one of those slightly cringeworthy, career-minded teenagers. After winning an award in business consulting, I posted about it and received a message from somebody at Google who liked my profile and asked whether I wanted an internship. He moved to Uber a few months later. We lost touch, then reconnected when he was recruiting interns and had one remaining position.
I said, “Sure, that’s awesome,” and ended up with a sales internship at Uber purely because someone had seen my LinkedIn content. That’s the point of a personal brand: it isn’t who you know, but who knows you and what they know you for. Your content creates that initial encounter and can lead to opportunities. It is essentially advertising for you.
James: That’s cool. It’s exciting that everyone has this ability. There’s no barrier preventing you from creating your own luck, as in your story of people approaching you with job opportunities.
Dan: That matters from an equity, diversity, access and inclusion perspective. Traditional hiring in consulting, law and banking has often carried a perception of nepotism: that you need friends or contacts inside the firm. Online content is permissionless. Anybody can create it without knowing the right people. Consistently producing good work attracts people who care about the same subjects. We should help more young people, particularly those from underrepresented and disadvantaged backgrounds, use content creation to advance their careers, because it provides a substantial advantage.
James: Totally.
What Dan Thinks Of Range#
James: You have worked across marketing, consulting, sales and technology. How has that range of experience helped you reach your current position? Has it been valuable?
Dan: It has been essential. My younger self wanted to try everything, which seemed uncoordinated at the time. But I had an early thesis: I did not know what I wanted to do, so I should sample many things.
That helps in two ways. First, you discover what you like and dislike. I tried sales, marketing, design, operations, project management and front-end web development. You acquire varied skills, test different work and see the world from different perspectives. I eventually discovered that I most enjoyed product marketing, sales and content—work with a strong human element—rather than purely technical or numerical tasks.
Second, a generalist skill set is valuable if you eventually start something and take it from zero to one. It gives you a holistic problem-solving mindset. When addressing a problem at Earlywork or in my job, I consider the technical perspective, design because I have worked in design, the customer and marketing perspective, and the sales pitch because I have worked in sales.
When you are early in your career and uncertain about your direction, collect varied data points. More experience gives you more lenses through which to view the same problem, which generally produces more robust and successful decisions.
James: David Epstein’s book Range, which I’ve discussed on the podcast, argues that breadth can support success and help people find the right career. That contrasts with the classic 10,000-hours principle, where becoming good at something means focusing on it exclusively for years. Your approach is to develop experience across several areas.
Then, somehow, those experiences will interconnect and create an advantage because the diverse pieces line up. As you said, they give you a much better perspective and let you see things in a new way. It’s extremely powerful.
Dan: The specialist-versus-generalist question is interesting because there is a balance. People describe a T-shaped model: being competent across many areas and excellent in one or two. That’s broadly the model I follow. I’ve always liked Scott Adams—are you familiar with him, the creator of the Dilbert comic?
James: Scott Adams.
Dan: He is one of the best examples of a talent stack. Adams was funny, but not the world’s best comedian. He could draw, but was not the world’s best artist. He understood corporate offices, but was not the world’s best corporate employee. The intersection of those three above-average capabilities let him create a distinctive, humorous comic about office culture and achieve enormous success.
I have not read Range, so forgive me if I misinterpret it. Exploring widely early is valuable, but you will find subjects you naturally gravitate towards, enjoy and find energising. The magic comes from identifying two, three or perhaps four of your strongest areas and finding their intersection.
A strength may be a skill or knowledge of a field. Suppose you have worked extensively in sustainability and also love making TikTok videos. If you understand social media, short-form content and humour, you might create a sustainability TikTok channel.
I constantly think about intersections. Everybody has a rich, complex life story, encounters different things and develops particular strengths. Combine those strengths into an offering nobody else can replicate because nobody else is you. James, you are the best at being your particular version of James—without insulting my other friends named James.
People often struggle to identify their strengths. Ask which school subjects you most enjoyed and performed best in. Reflect on the activities that drew you as a child because you found them fun, exciting or interesting.
In year three, a friend and I both wanted to be creative. We saw funny, creative television advertisements and decided marketing and advertising were fascinating. At university, I initially studied finance and biology, but eventually returned to marketing. I rediscovered my childhood interest in telling the story of why something is a valuable solution for somebody.
You can also ask your five closest friends and family members what you do better than most people, which skills they associate with you and where they see weaknesses. Their answers will reveal patterns. Even if you lack self-awareness, people around you hold perceptions of your strengths. When a young person is uncertain about what to do, finding those early intuitive strengths and inclinations, then considering how to combine them, is powerful.
James: Skill stacking shows that you do not have to be the best at any single thing; somebody will almost always be better. Combining abilities helps you discover where you can thrive. Identifying strengths and weaknesses matters, but it can be difficult to assess yourself during ordinary life. Other people’s perspectives can help reveal whether you are funny, for example, or what else you do well.
Dan: The caveat is that other people’s opinions do not necessarily reflect what energises you internally. They may not have seen every interest. You might perform well in mathematics at school through hard work without enjoying it, so everybody calls you “the maths person”. Meanwhile, you may love drawing and painting, despite not yet being as skilled, because they give you passionate energy.
To be honest, I back passion and energy as a better long-term bet than simply getting good grades in something. They usually coincide: you tend to do well at the things you’re passionate about because you think about them often and that is how your brain operates. But the relationship isn’t always one-to-one.
Dans’ Advice to New Graduates#
James: I’ve learned so much from this fascinating conversation and have many takeaways. I have one final question, Dan. What advice would you give people graduating and starting their careers in 2022?
Dan: Regardless of whether they enter a startup or corporation, I would say: optimise for learning. By that I mean the learning you want, not simply accepting your company’s structured program. Identify what you want to learn and ask how you can learn it as quickly as possible. How can you practise, teach and engage with it? Perhaps you want to become an excellent public speaker, salesperson or developer. Be intentional about how you spend your time—not every second of the day, because you need breaks, but at work and on side projects. Ask what you are learning and how quickly, and create a clear framework and plan.
The other piece is to find people who care about similar things. That begins with an ongoing question: what problems would you like to work on ten or more years into your career? Perhaps it is climate change, nuclear warfare or artificial intelligence. There are many fascinating areas, and exploring them takes time and reading. One of the best things you can do is talk to other people, because co-learning is beautiful.
Find capable people with good values who care about similar problems and are doing something about them. Learn from them and teach one another. Looking back at university, I still have friends who followed very different paths: cryptocurrency, law, video-game design and PhDs. The common threads are a strong core of values, curiosity and intentionality. Find people with whom you resonate, because those around you will have an outsized impact on how your career progresses.
One more thing: start creating content now. Find what you care about and make a newsletter, TikTok videos, social-media posts, art or anything else. The format doesn’t matter. Creating content will help you find people who care about similar things, and that will be a superpower for years to come.
Contact Dan#
James: This episode has been fantastic and offered me so much value. Thanks for coming on the podcast, Dan. Before we let you go, where can people find and connect with you?
Dan: On Twitter, I’m @DanBrockwell—B-R-O-C-K-W-E-L-L—and I post there often. My baby and my love is Earlywork. The website is Earlywork.co, and our free career advice and resources about the future of work for young people are at Earlywork.substack.com. You can also find our Slack community through the Earlywork website. It has about 1,800 young people across Australia and New Zealand learning together about careers in product management, marketing, design, engineering, cryptocurrency and sustainability.
We’re trying to build the leading community for young people creating the careers of tomorrow. If you want to do exciting work, create your own things and make a positive impact, we’d love to have you in the community. I’ll see you there.
James: Thanks so much for coming on, Dan. We’ll see you soon.
Dan: Absolute pleasure, James. Thank you so much.
Outro#
James: Thanks for listening to this episode with Dan. I hope you enjoyed it as much as I did. I think there were so many nuggets of wisdom throughout this episode. If you want to get my takeaways, the three things that I learned from this episode, please go to Graduate Theory.com/subscribe, where you can get my takeaways and all the information about each episode, straight to your inbox.
Thanks so much for listening again today, and we’re looking forward to seeing you next week.