The 2010s emerged as an incredibly promising time for bright-eyed founders. Household names like Lyft, Snapchat, and Slack were being founded on the heels of their big brothers, Facebook, Google, and Amazon. VC made a historic shift, with mega funds knighting unicorns faster than new iPhone releases.
And in the middle of this prosperous startup boom, Dennis Kim was finding his own way. Like many other college students who aimed to build the next Facebook in their dorms, Dennis was also looking to make his impact on the world through his virtual education platform.
“I created a marketplace for connecting international high school students with smart college mentors, for all kinds of educational services. There was a management system, kind of like a virtual classroom, to support this environment where mentors and mentees could interact. They could upload PDFs and raise their hands.”
It was a pre-quarantine Zoom-style education solution. The startup would take up plenty of Dennis’s time, but it was only one waypoint on a much longer and complex path of self-discovery. It’s a path that you can’t understand unless you start at the beginning.
Dennis was born and raised in Seoul, South Korea. But, at ten years old, he moved to Washington as a foreign exchange student. In fact, Dennis called me from Washington, even though his current job is based out of Philadelphia. Dressed smartly in a polo, taking the occasional pause to capture a new vignette, he recounted his early experiences in America.
Dennis felt lost when he first arrived, especially because he had almost no knowledge of English and he was alone. Later, he’d also learn that the exchange program was a fraud, and had to scramble to look for a new home.
Coming of age in a foreign country, he had to put in extra work just to be on the same level as his classmates. “I remember waking up super early to become better at English and taking all the extra steps because I had a heavy accent,” Dennis recalled. “During the process of finding my family and assimilating into a different country, I really developed this grit…It’s the value that I have, where I put in the work no matter how the process will turn out to be, and I learn by constantly practicing.”
Despite the difficulties, Dennis flourished. He found his second family living with a fourth grade classmate. And when he returned to the States a few years later, he had a ticket to one of the nation’s most prestigious charter schools, The Thomas Jefferson High School For Science and Technology.
As a teenager, his English was significantly better, and his interests had just begun to materialize. He became the class council president, earned a semifinalist designation at the Siemens Science Competition, and competed in Lincoln-Douglas debate.
Living between different countries, refining his interests, and interacting with different groups, Dennis learned another valuable lesson. “All those experiences also helped me be more open-minded. There’s always this element for Asian-Americans to fit into different groups. It’s the identity question. Living in America, I came to learn how different people have different opinions, and different ways of doing things.”
Being an immigrant turned out to be a blessing for Dennis. He built within himself a deep mental resiliency and a toolset to adapt to any situation he was put it. And in a fateful foreshadowing of Dennis’s future, his high school graduation hosted the founders of Robinhood, the $11.2 billion investment platform.
When Dennis arrived at Harvard, he began fleshing out a passion for entrepreneurship through a class led by Professor Paul Bottino. The course, Startup R&D, would give him the opportunity to bypass the classroom environment to work on his startup for academic credit.
The class threw Dennis headfirst into entrepreneurship. He spent his hours at the i-lab, Harvard’s entrepreneurship center. He met classmates who were both talented and business-savvy. And he listened to seasoned founders discuss their own startup experiences.
Dennis worked tirelessly on his startup, but another avenue to interact with entrepreneurship had opened up in front of his eyes: investment. As president of the Harvard College Entrepreneurship Forum, he connected students with high profile venture capital investors in a fireside-chat setting.
“I was constantly inspired when organizing these chats and participating in them, as well. In particular, in interacting with investors, I was always fascinated with how these guys had such conviction around something that hadn’t occurred. And I was interested in how they materialized that interest by connecting with entrepreneurs who also shared that vision.”
It also helped that his startup cofounder’s father was Jim Breyer, one of the original investors in Facebook and a member of the prominent VC fund Accel Partners. Hearing stories of Breyer’s discovery of Facebook, his new bet on AI, or his interactions with founders proved to be the tipping point. Investing was just as viable a path as entrepreneurship, and he could learn a lot on the job, too.
“I believed it was probably better for me to understand how different mechanisms in the startup world work. How different businesses run. What drives them. How they’re impacted by the environment. What it takes to build a business that is solid, from the bottom-to-the-top.”
As an investor, he’d have a finger on the pulse of the entrepreneurship world and work with startups across different fields. “I wanted to be part of the ecosystem, insure this risk by being an investor, and be helpful to many entrepreneurs.”
Most firms hire with the expectation that you have at least two to three years of experience under your belt, but Dennis started right after college.
As a young person in VC, he immediately gets access to the tools to make or break startups. “It’s definitely a privilege having a platform. I can chase entrepreneurs and support their dreams through capital infusion and through tactical work we can do together. But being young adds a humbling layer to that privilege.”
Whereas other investors may be able to transfer domain experiences into their deal flow, Dennis has to put in extra due diligence to develop his frameworks. Without a family to attend to, though, he can spend more time mastering the requisite skills. How can he learn more about an industry? What additional step can he take to strengthen his paradigms. What new tactic can he use to help an entrepreneur?
Dennis has spent the past few years learning and applying these skills at Susquehanna Growth Equity, a firm that invests $5-$100 million in software, SaaS, and internet businesses. And lot of his time goes to sourcing deals so that his firm can invest in quality companies.
To source, Dennis uses multiple tools. When there’s an industry conference, he scrapes the list of attending companies to search for potential investments. He also uses tools like LinkedIn Sales Navigator to interact with entrepreneurs and filter for certain criteria that the firm is searching for.
Sourcing also tends to snowball, building on old connections to generate new. Bankers, accountants, lawyers, and other startup intermediaries have their own network of entrepreneurs and drive deal-flow, too.
However, Dennis explained that even though he looks at many startups, most don’t make the cut: “a lot of a good firms or good funds…look at or engage with 10,000+ companies and will only invest in less than twenty.” This means most of his job is passing on perfectly good deals.
To cut through the noise and find the best investments, Dennis keeps an eye out for a couple red flags.
The first red flag is when businesses are attempting to create a market that doesn’t already exist. Unless he heavily believes in the potential of this new market, he’s often hesitant to take on the deal. These startups often base their predictions on an external variable they can’t control, and that spells uncertainty.
Second, counterintuitively, Dennis often takes a second look at companies with large amounts of funding.
“Many entrepreneurs pride themselves in their ability to raise capital. And I commend them; their idea is being validated. But it becomes very tough for investors to verify whether the product itself is gaining all the traction/revenue or if it’s just the capital producing it. They could have a faulty product, but if they can put a ton of money into their sales and marketing team and people are hitting the phone out-bounding, they could present a nice growth story.”
In other words, an investment that returns plenty need not be tied to plenty of investors.
Dennis’s situation as a young person in VC may seem like the exception rather than the rule, but he reminded me that the landscape is changing. It’s becoming more equitable by the day. The first step is acknowledging that you want to be an investor and making that an integral part of your identity. Find any opportunity you can, whether it’s a part time job or internship.
“You can leverage your college career, website, cold call, email, express interest, etc. [And] if an investor made an investment that you have an opinion on, don’t be shy. Find the guy’s email and share some insights and ask for a phone call out of pure interest. All these little things will add up,” Dennis explained. “I see a lot of firms, competitors, and peers, take in younger investors,”
Immigrating to the United States, adjusting to cultural differences, and absorbing as much information as he could from those around him, Dennis reminded me of the importance of adaptability. No matter your situation, if you internalize your values and tirelessly seek improvement, you will succeed.
Know what you want. If you know what you want, figure out a way to get it. There are always ways to get it. And all the things that you aspire to be, make it your identity. If you want to be a hardworking guy, relating with a lot of people and just crushing life, whatever it is, that is your identity. Believe in it.