Careers in startups are generally filled with high levels of risk and unexpected turns.

And New Zealand-based Sam Wong’s career is no different. 

Last month, Sam presented to the W21 Student Fellowship cohort, sharing insight from her startup career to date. She imparted on us three pivotal pieces of advice, including that you should never stop learning because this is a driver for progress and innovation.

Setting the scene

After obtaining her law degree from UNSW, Sam practiced corporate and litigation law for five years. With plans to move to Paris to practice International Arbitrage, the financial crash of 2008 forced Sam to rethink her career.

It was at this time that she chose to make the bold leap into the tech world.

In the quest to secure a job at a startup, she remembers telling “anybody and everybody” that she would work in any position regardless of pay.

Eventually, her handwork and tenacity paid off, and she was offered multiple jobs in several startups.

Some of these were unpaid and unsuccessful, however, one of them wasn’t. Her luck changed when she landed a job at Surfstich.

Default to open

Sam’s first piece of advice was, when applying for jobs, you should “default to open".

If she hadn’t posted on Facebook, spoken to so many people and been open about the job application process, it’s unlikely Sam would have gotten the job at Surfstich. 

She outlined how each startup’s journey can be placed within one of four quadrants below — here more funding and faster growth can result in a ‘pickier’ attitude to hiring. Sam was careful in detailing that ‘picky’ meant hiring someone who best fit the role advertised. 

When applying, adequate research into each company can reveal its position on the graph and possibly divulge how ‘easy’ it may be to get a job there. Startups are often scared of “bad hires”, and it can slow down progress, costing them in time. 

As an inexperienced university student, constant rejections are incredibly disheartening. But Sam’s advice hinted to me that I may just be looking in the wrong place.

Backing yourself

In true startup style, Sam’s journey with Surfstich was filled with hard work and an intense drive to learn. Sam’s second piece of advice highlighted the importance of “say[ing] yes to things you’re unqualified for” and backing yourself to learn quickly on the job. 

As mentioned (and lived) by Sam, when applying for a startup role, you should never disqualify yourself from a role because of your supposed professional inexperience and shortcomings. In early-stage startups, job titles are never as explicit as in more established companies, forcing founders and initial employees to take on much more than the initial job description. 

However challenging it may be, the most invaluable asset to a startup is an individual who is able to contribute beyond their job description.  

Live and learn

After years of evolving tasks and titles, Sam hit a learning plateau, and what she did in response leads to her third and final piece of advice: “optimise for learning not money”. 

This mindset makes learning the priority, rather than aspiring for wealth. This is important because having an money-fuelled ego can cloud the main objective of a startup, whereas a focus on learning can only improve the product. 

Sam’s priority of learning led her to apply for the Startmate Accelerator program, during which she started her own legaltech startup called Capacity HQ.

Soon after, Sam joined Startmate, imparting her own pearls of wisdom to following cohorts.

From there, Sam began her journey at Blackbird as Partner, leading investments on countless successful ventures. 

The graph above shows a possible projection of “riding the growth” from the infancy of a startup, to days past series A or B. This pathway mirrors a steep learning curve as outlined by Sam, revisiting all three ideas of “optimising for learning”, saying “yes to things you’re unqualified for” and “being default to open”. 

Sam’s recount of her journey through law, tech and venture capital, highlights not just the highs that a career in startups can bring, but also the intense lows that one can experience. 

When imparting wisdom upon impressionable and eager students, it’s crucial to paint an accurate picture. In this case, Sam Wong did just that. Neither crushing dreams nor providing false hope, her shared experiences produced a sense of reality as well as encouragement and hope. 

Chaotic and highly risky,  sometimes “you may not have a job in 12-24 months”, but in the startup world, you “own the sense of accomplishment” , building something that can offer real impact to an ever changing world. 

In the constantly evolving and increasingly turbulent world of today, the possibility of impacting even a handful of lives is the reason why many of the Student Fellows — including myself — joined Startmate.

Sam’s realistic yet positive recount of her career taught us how to best optimise our time working in startups, with advice applicable beyond our working lives.