The unequivocal best part of our job is playing a cameo role in the journeys of seriously talented people; doing our small part in helping them turn their grand visions into reality.
Every investment we make is a big decision, because we’re making a commitment to walk alongside early-stage founders for a considerable period of time. In the Western world, the average marriage lasts eleven years; a venture fund has a minimum lifespan of ten years.
This post is about our biggest investment yet - in one of the most talented, ambitious, and relentless people we’ve come across, after having spoken to thousands of founders over the past four years.
This investment is the unstoppable Jessy Wu, who joins our team as an Investment Manager and our Head of Community. In addition to leading her own investments end-to-end, Jessy will drive our efforts to build the AfterWork community into the vibrant spiritual home for startup operators, thinkers, and hustlers. Our community will be a space where members can connect with one another, and work with our portfolio companies on their long and arduous road from anomaly to icon.
We’ve gotten to know Jessy over the last 9 months she’s been a member of the AfterWork community. We’ve been routinely blown away by her clarity of thinking, her ability to run through brick walls as if they’re made of tissue paper, and her give-first mentality to our community, portfolio companies, and the broader startup ecosystem. As venture investors, we think in decades instead of months or days; and we’re excited to start on our ten year journey alongside Jessy.
What we loved about the investment opportunity
Jessy is on par with some of the most experienced and effective operators we’ve ever met
Jessy studied Philosophy and English Literature at the ANU. She likes to say that when she graduated, “the philosophy factory wasn’t hiring”, and she was fortunate to land a role in management consulting. However, we believe that a robust foundation in thinking in a structured way about hard problems, alongside a healthy dose of curiosity, makes for an excellent early-stage investor.
Jessy’s philosophical training shines through when she’s unpicking an investment decision. She’s innately curious and comfortable confronting her biases. The world of early-stage investments isn’t black and white: successful venture investors appreciate the role that chance plays when constructing their portfolios. Jessy is comfortable with uncertainty, and views their world through the lens of expected values.
Additionally, AfterWork is a startup too. This means there is always a fire to put out, or a task that’s never been done before. Jessy is as comfortable getting shit done as she is debating philosophy of language with Wittgenstein. In the nine months we’ve worked with her, Jessy’s done the heavy lifting with organising community participation in deals, run our social media presence, onboarded a dozen community members, and organised a launch party.
Jessy doesn’t wait for opportunity to come knocking
When you kick up as much dust as Jessy, something is bound to stick. Jessy is courageous and throws herself behind what she does with the utmost vigour.
Sliding into DMs is one of Jessy’s spikes, and one of her favourite tools when it comes to creating her own luck. In fact, that’s how she came to become involved in the AfterWork community!
As early -stage VCs, we also don’t wait for the best deals to land in our inboxes. It’s in our DNA to knock furiously on the doors of the most brilliant founders, and earn our right to be a part of their fundraises. We don’t believe anyone exclusively creates their own luck, but we are excited to back those who will chase luck down.
Jessy’s courage is next level, and personifies AfterWork’s core values
It takes serious gumption to back yourself and go all-in on your idea. As all early-stage founders know, the beginning of the road is rocky, lonely, and unglamorous. We see this everyday in companies we meet with, and we admire the courage of the founders who take the plunge. Not too recently, we dived in the deep-end ourselves. Although we’ve started getting rungs on the board, AfterWork is still early and unproven.
Courage is the trait we most admire in Jessy. What’s more, Jessy loves to put her courage to work going into bat for others. Here she is unafraid to vocalise what so many were thinking and feeling to the CEO of PwC Australia:
Courage is also important in the context of being a first believer in a company. Investors know it’s easy to follow a lead and pile money into a company that’s already proven. It takes bravery to stand up for what you believe in when making an investment or standing for a point of view. We’ve seen this play out both in investment decisions and in day to day discussions. Jessy isn’t scared to stand up for what she believes in, and doesn’t let discomfort get in the way of speaking truth to power. At the same time, she also personifies the statement “strong opinions, weakly held”.
Jessy brings skills that can amplify the rest of AfterWork
Jessy makes the team more whole. Our weakness has been a fear of putting ourselves out into the world. If you’ve followed AfterWork on social media for the last 2 months, you might find that hard to believe. In truth, Jessy has been the force-of-nature behind supercharging our brand-building efforts. Her conviction in what we’re building, and enthusiasm about our story, has given us the prod we needed to step into the spotlight and share our story with the world. In doing so, we’ve attracted so many additional community members who found a resonance with what we are building.
The challenges we saw
What if Zoom isn’t like real life?
As a community-powered VC, we’re lucky to get to know a bunch of top-tier talent in the community - and now we’re excited for the first of them to make the leap to become a formal member of the team. Over the next decade, we anticipate the vast majority of hires will come from the community.
But as much as you can get to know someone over Zoom calls and an overactive Slack channel, until April 2021, we’d never met Jessy in person. We can imagine Jessy probably also felt some trepidation when she walked into the arrivals section of Perth effort. But spending two weeks together in WA solidified our transition from internet friend, to team member, to lifelong partners in crime.
How can we make sure building AfterWork sustains Jessy’s interest for the next 10 years?
As VCs often say to portfolio companies - people are the most important component of every business - regardless of size, stage, or sector. To attract the best talent, we knew we needed to be intentional about creating opportunities for people to become formidable versions of themselves, over a significant timespan.
As we got to know Jessy, we found out that she strongly identifies as a “two” enneagram. This means she thrives when she’s able to prop up other people, particularly when they’re important to her. We’ve certainly seen this in action - and many times we’ve been surprised and moved by Jessy’s generosity towards us, our portfolio companies, and our community.
As such, we worked together to design a role which combines Jessy’s restless curiosity with her desire to build something for others that’s lasting and scalable. We see Jessy as a core member of the founding team, and are excited for AfterWork’s success to be aligned with her own growth over the next decade.
How we got conviction
We’ve worked with Jessy for the last nine months, and what we’ve achieved together has been a group effort. She’s gone above and beyond to help build AfterWork Ventures in the wee hours she had ‘after work’ and we can’t wait to see what she achieves as it becomes her life’s work.
