Life as a Story Ventures Fellow

by Emma Reilly

Before COVID-19, I was on track to graduate from Yale University in the spring of 2021 with a B.A. in History of Science, Medicine, and Public Health. When the pandemic hit, I spent months thinking through the reality of a virtual senior year, and ultimately decided to take a gap year with the hope of a more “normal” 2022. As someone who struggles with the uncertainty of change and is painfully indecisive, the act of withdrawing from college was the most difficult decision of my life. Once I committed to postponing my senior year, I spent time considering how I wanted to spend my time off. I was fortunate enough to be able to use this as a year of discovery when, for many, it was a year of loss.

With past internship experience at a sports media agency and an investment bank, I wanted to explore a new industry. My previous internship in private capital markets sparked an interest in venture investing and learning about how companies are built during their earliest stages. When I had my first conversation with Story Ventures I knew nothing about data technology, but was intrigued by the way Jake & Brian spoke about their data-driven thesis and their excitement to have me join the team, frankly, when I needed it most. I started the fellowship program at Story in September 2020, and for the next six months I was embedded in the world of venture.

Working in Venture Capital had always intimidated me because I saw the industry as a black box — difficult to get into, risky, and seemingly reserved for the lucky few who manage to perfect it. I was taught, like many, that there is a well-established pathway into venture: college, investment banking or consulting, then business school, before landing a coveted role at a fund, which even then wasn’t a guarantee. It’s rare for anyone to bypass this track and get into venture without checking each of these boxes, but at Story, they don’t emphasize the importance of this trajectory. Instead, they look for people who are insatiably curious, hard working, detail oriented, and willing to think creatively, outside the box.

The Fellowship

My first day was, in a sense, everyone’s first day. The Story team was in the process of moving into their new NYC office and there was still so much to do. I didn’t know what to expect or what I had gotten myself into, but one thing was certain, I was terrified. I had a clear image in my head of what my first day would look like — intimidating, stiff, a whirlwind of confusing technical jargon. Instead, caught in the fervor of moving chairs and setting up desks, I quickly felt like part of the team. They were building out their new office, and I was thrilled to be part of an exciting new chapter.

What I enjoyed most about the fellowship was that my tasks changed constantly, giving me the opportunity to plug into different facets of the business. Overall, my time was split between investing and operations. On the investing side, I listened in on calls with Jake and Brian to acclimate myself to the terms, themes, and common practices of venture. I had the opportunity to write investment deal memos, research new tech regulations, and create marketing materials for fundraising and pitch meetings. On the operations side, I was exposed to the processes of how to scale and manage the day-to-day operations of a young and growing fund. I spent time organizing and tracking deal flow, streamlining internal processes, and working on content and brand strategy at the fund level. Carlie taught me every tip and trick of operating a business, from how to institutionalize processes, to setting up the wifi ~before~ moving into a new office space. ;)

Though there are many anecdotes I could share about my day-to-day experiences at the firm, the better narrative is about why I believe Story Ventures is different from every other venture firm.

For starters, Jake and Brian operate as though it is their will against the world. I often asked them if they ever thought they’d fail while building Story, and their answer has always been “failing isn’t an option”. For the past five years, there was no forward or backward thinking, just doing. I experienced this first hand during their most recent round of fundraising. I’d watch Jake run, quite literally, from meeting to meeting with the occasional bathroom break and push-up session, while Brian would be hunkered down in the conference room with a calendar of back-to-back meetings and a smile on his face.

Despite the intensity of their work, the beauty of building a company alongside your brother is that it allows for a certain amount of comfort and casualness in the work environment that is a breath of fresh air. The Story Team created a culture of conversation and respect that naturally removed the barrier between my work and theirs. Because of this, I got to spend 80% of my time working on projects, and 20% of my time absorbing every word that was said around me and adding them to my ever growing notes. The days were fast-paced, full of investor meetings, company pitches, and debates on the future of technology, with a pinch of playing music, discussions about our “inner age”, and Jake’s occasional dad jokes. Despite my lack of experience, they always offered me the freedom to explore companies that were of interest to me — I can’t speak on other firms behalf, but I’m assuming this is not the norm.

Jake and Brian’s pick of Carlie to be their Chief of Staff is further evidence of their ability to cultivate a refreshing environment in an industry that can often feel stagnant. With her background in operations, marketing, and management, Carlie broadened my experience beyond the investing side of the venture world. She took on the role of my mentor, and when she wasn’t teaching me work-related knowledge, she was passing on life and career advice that I didn’t know I needed. Despite having a hand in every corner of the fund while simultaneously building out an office, I think everyone at Story would agree she kept us running.

From a thesis perspective, no other NYC firm invests solely in data technologies. With a data-first mentality, Story believes the largest businesses will be built on the backs of significant data feedback loops: data capture, data organization, and data application. Despite the complexities of investing in data technology companies, Story has perfected the process of exposing individuals like me to this ecosystem in a way that’s comprehensible, by building a compelling narrative around their thesis. This is something that’s increasingly important for helping people new to the tech ecosystem understand and engage with the data that underlies our lives.

Although their thesis is unique, what truly differentiates Story is how they view the long-term impact of their investments. Carlie and I have had many conversations with Brian about the advancement of technology, and I believe his thoughts reflect the authenticity behind the Story thesis — an authenticity that I never expected to see in venture. At its core, technology increases efficiency and decreases friction as people are benefiting from unprecedented levels of access, knowledge, and transparency. While this is true, it also has second and third order effects, not all of which are positive, including mental illnesses and data overload. As someone who personally struggles with mental health, hearing Brian discuss these startups not solely as financial opportunities, but also as companies focused on the people that benefit from their services, was refreshing and reassuring. Venture Capitalists have the power to invest in founders and visions, and Story emphasizes the importance of finding those who are creating the building blocks of the altruistic side of technology.

Coinciding with their mission-oriented investments, Story’s ability to see the potential in people and measure their hunger to build something great has contributed to their community of exceptional founders. This is in part due to the way Story conducts business — direct with no BS or sugarcoating, which has naturally attracted like-minded people. For Jake, Brian, and Carlie, the investments never end at the term sheet. The benefit of having a concentrated fund is the ability to be a true partner for founders, and support them emotionally as they build. I watch them prep founders before big pitches, provide advice through legal negotiations, and emphasize the importance of sending the elevator back down to mentor and support younger founders. Seeing the work that is put into helping entrepreneurs evolve gives me a great sense of comfort knowing that these are the people and companies shaping the development of society.

Conclusion

More than six months have passed since I started at Story Ventures, and I’ve left with an interest in data technology, clarity on what I want to do, and three amazing people that I truly believe have had the greatest impact on my life this year. During a time when most students chose to return to campus, I found every excuse to continue on with the fellowship, as I got teary-eyed every time I thought about leaving. I believe I had an extra special experience given that I saw the granular details behind building a young fund. In a few years, once they have an office full of employees and a scaled fellowship program, people will miss out on the rush of the early days: outfitting a new office space and lengthy conversations about defining the brand and culture of Story. Yet, they’ll still be a part of the same Story team that I had the pleasure of meeting.

It doesn’t take long for one to learn that Jake, Brian, and Carlie bring humility and authenticity to an industry often portrayed as the antithesis of those qualities. Every morning, my mom would joke that I was going to hang out with my “friends”, but that’s truly the environment that the Story team has built over the last five years. They felt more like mentors that took me under their wing than they did bosses, a quality that I believe is rare these days. They place an importance on every word you say and repeatedly ask for your input — and as a confused college student, filled with uncertainties during a particularly disconcerting time, this has given me purpose and direction.

Though the pandemic has created lingering uncertainties in my life, I know for sure that I’m counting down the days until I can call myself a proud investor in the Story fund.

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