Venture Capital JourneyWith Lessons From Failure (ft. College Student)

Andrew Lee
8 min readJun 1, 2021

Taking a career path towards medicine upon the first entry of college, I encountered an unprecedented conflict — not during the first or second but my last year of a college career. Before diving deeper into the abyss, its background story might be appreciated.

For someone who enjoys problem-solving, college is a paradise since almost every aspect involves a variety of problems. On top of that, one can experiment and improvise their solution with numerous resources. Until I identified a significant problem, I had been merely focusing on how to go to medical school like many of my colleagues: high GPA and MCAT score, volunteer, shadowing, and research experience, etc. Although these components are needed, medical schools are obviously not looking for clones with different names. My problem was that I was deviating from the real me by disregarding what I’m good at and passionate about. Augmenting one’s own strengths and adjusting weaknesses can bring each individual’s uniqueness for diversity, which means more representation, to transform the current healthcare system into an inclusive health ecosystem that revolutionizes how people get and remain healthy. To resolve my own problem, I started to harness my effort and time on “how I can iterate a meaningful value with my talent.”

I’m still passionate about practicing medicine with a broader perspective by gaining experience in both clinical and non-clinical aspects of healthcare.

Its first byproduct was a student organization that my friends and I founded to help students with Korean heritage find academic, social and career resources. I strongly felt that there was a lack of unity and support in this specific community despite more than a thousand organizations across the campus available at the time. When the entity was established, we moved on to the next step — exposing ourselves to potential members. We expanded our channels via Instagram, Youtube, and SEO. Of course, we displayed our presence through multiple fundraising events and partnerships with local business entities prior to COVID-19. Even during the pandemic, we continued delivering our service with more guest speaker series and virtual meetings. Here are some key statistical outcomes: +120 members, +$4,000 funding raised, +5 partnerships ( ≤ 50 % member retention rate is something that needs to be improved to grow further). These two years of experience taught me how to learn constantly with grit to provide solutions for problems that are around me.

The second byproduct needed even more grit. Thanks to my university, I was able to join a pre-accelerator program designed for undergraduate students to learn skills necessary to build their own venture and reach a suitable product-market fit. The curriculum offered content and knowledge in the following categories:

  • Hypothesis Generation, Experimentation, and Business Model Canvas
  • Customer Segments
  • Interviews
  • Value Proposition
  • Analyzing Findings
  • Minimum Viable Product
  • Customer Relationships
  • Storytelling

Throughout the program, I was assigned a mentor, Steve Schaffer, a founder of and an angel investor. He was very willing to help me with practical advice by holding a weekly one-on-one meeting with topics ranging from user stories to business models. Moreover, Jacob Guss, an MBA student at UT Austin and a founder of Bold Move Beverages helped me with pitch decks and networking, specifically. With such a great opportunity and amazing individuals, I was able to launch my own venture, Yeon. Yeon helps college-applying students learn about college life and beyond through compatible mentorship and affordable service within a sustainable virtual community.

Without any doubt, I truly loved the first-hand experience in entrepreneurship, and the fact that I realized this opened my personal door to the startup community. To further pursue my interest, I decided to look for opportunities to gain experience in Venture Capital, and here is how I reasoned through:

“A simple idea can change the world,” — I have solid faith in this sentence but with a few more words — “A simple idea at the right time with the right team can change the world.” When talking about the team, I believe this is where VCs come in. They spend countless hours to find which business can fit in that category even though each firm has its own investment thesis. But once they find one, they support with financials and resources like networking opportunities, entrepreneurial events, and necessary education to take on an accelerated adventure. Don’t get me wrong, though. The journey requires lots of sacrifices and effort. However, the beauty of this role is that people in this industry are one of the few that have the privilege to take part in shaping the future, bringing disruptive solutions to the world. For someone who enjoys problem-solving with grit, this is a great opportunity to be a part of the community and excel as an entrepreneurial leader. My eagerness to learn from a variety of startups and their founders on a daily basis makes me wake up early in the morning and drives me forward to keep learning. Coming from a pre-medical/science background, I believe that this gap-year moment is “the right time” to find “the right team” and take on a novel journey of mine onward.

Okay. Enough of sugar. The reality didn’t seem to understand my motive and intention (It’s actually the other way around; I was not prepared). So I’m going to share my failures and lessons learned from them. On a side note, this article by Kelvin Yu is very relevant as he shares his experience in his interview for a Venture Capital internship. I love how he maintains a positive attitude and manages to learn from his mistakes. That’s a sign of grit, right?

The core foundation: Networking

Here is an interesting statistics believe it or not: the average cold email response rate is less than 5%. The point is not whether this statistic is true but more about the fact that it is extremely inefficient. Well, if something is inefficient, it is a problem. Is there a solution for it? In fact, there are plenty. This is one of them but I’m not talking about business vs. consumer perspective but human nature and psychology. When I applied to two different firms but with the same resume and cover letter, I received an interview from one but not from the other. Interestingly, the firm that I received an interview with is where one of my friends interned. Thanks to his referral, I was able to do a short coffee chat with the co-founder even before the actual interview, where I felt much more comfortable. Venture Capital is a highly people-oriented environment, which means their inboxes are always full of mails from a number of contacts. Thus, a cold email out of the blue is likely to be ignored. Nonetheless, it’s important to note that there could have been other factors that resulted in the immediate rejection. Now, the main takeaway here is not to stop sending cold emails but increase the chance of recognition by going outside of a comfort zone to attend events and connect with a variety of people in the industry while sending emails at home.

For those who know that they want to break into Venture Capital in the first three years of college, joining relevant business organization and connecting with upperclassmen are great ways for networking.

Documenting insight/opinion with logical reasoning

It is worthwhile to mention that I did not get an internship from the firm, where I was referred by my friend. To clarify the process, I had a first-round with an associate, and it was mainly about getting to know more about me. Then the second interview centering around with their portfolio companies was with the co-founder I had previously met. This went well too until the final interview with the other co-founder of the firm. I was very naive to think that the last interview could be a breeze like the other two. However, I was asked questions regarding specific sectors beyond their portfolios and my opinion. I was not prepared for this knuckle curveball. Of course, I said something but it could’ve been better if I shut up and admitted that I didn’t know anything. The thing is that I knew the answers but did not know how to organize them in my head (the moment my neural synapses housing the cerebellum and prefrontal cortex went boycotting) and deliver it comprehensibly. After this failure, I decided to write blogs about my work that delves into companies I find interesting, their industry trends, and analytical hypotheses. I heard people call this sort of work an investment thesis but I don’t want to put a fancy word upfront when I barely took a baby step with the learning process. To an extent, this hope-to-be articulate and insightful work can help me organize my own portfolio and maybe grab the attention of others in the near future.

Learning is not enough but proactive learning does its job

The third internship opportunity was not with Venture Capital but with Venture Studio (what’s the difference?). This meant more learning on top of learning! This failure gave me an important turning point in my learning process. Unlike the other two firms, this Venture Studio was actively looking for interns at my university. So I happen to witness other students who were applying — an MBA student, a JD candidate, an undergrad with a finance and engineering degree, etc. Even from the point, I started comparing myself to others, I happened to stop learning proactively. Proactive learning, at least in my definition, means that I should clarify the purpose to myself, strategize how to learn, and digest information effectively. In this context, I needed to learn something that demonstrates my interest and adds unique values that can be beneficial to the firm (because it’s not a competition). Instead, all I did was practicing more interviews and merely researching about the firm and its portfolio companies. It doesn’t mean what I did was not helpful but there was no clear purpose in my learning process. Yet, I still have two more firms that I recently applied to, and one of which gave me an assignment to tackle for the next round of interview. Let’s see what I’ll learn from the upcoming opportunities.

Final Thought

I believe that I cannot afford to feel negative emotions towards what happened in the past because nothing can change it. Therefore, the most logical action is to learn from the past and better prepare for the future. A little moment of desynchronization should not put one down but act as a stimulus to move forward. This is where we live and how the world functions. People are like countless stars spread in a broad universe with distinctive shapes and colors. However, all of them can shine upon the world, and adding more of them will gleam even more.