Breaking into VC — Art or Science?

Daryl Lim
15 min readFeb 27, 2023
Photo by CHUTTERSNAP on Unsplash

Breaking into VC is a goal for many aspiring investors, entrepreneurs and students but is it an art or a science? The answer is, it’s a bit of both.

While there are certain skills that can be learned, the VC industry also requires a unique combination of creativity, intuition, and interpersonal skills. To be successful, one has to have a strong understanding of both the financial and technical aspects of investing, as well as the ability to form relationships and make decisions that are based on more than just data and analysis.

In this article, I speak to people across the globe who are democratising access to VCs and discuss the skills and attributes that are essential for those looking to break into this competitive field.

#1 🇨🇦 🇭🇰 Katie Ko (Ripple Ventures)

  1. How did you begin in VC?

My journey in VC started pretty unknowingly. Throughout university, I made an effort to immerse myself in the startup ecosystem, and worked as an operator across multiple startups ranging from e-commerce to fintech. I also co-founded an eco-friendly underwear company, SINGLA Intimates, where I led marketing and growth.

As time went on, I grew an interest in venture capital. Curious what the other side was like, I joined Front Row Ventures as a Partnerships Associate, where I built relationships with various accelerators, VCs, and university campuses.

I later transitioned into an Investment Associate, as I was curious about founder conversations and the diligence process. That same summer, I was selected to participate in the RippleX Fellowship programme, a fellowship designed to equip underrepresented students with opportunities to learn about startups and venture capital.

Upon completion, I joined Ripple Ventures as an Analyst, and I’m honestly so grateful for my opportunity at the fund. I appreciate each interaction with founders, interfacing with emerging tech, and the community I’ve gained in my short time in the game. Best part is getting to collaborate with an all-star team, who I adore and admire greatly.

2. What is the most important skill in VC?

Strong opinions, loosely held. A big thing I learnt being at Ripple is that you’re essentially hired to make decisions. Conducting research and meeting founders is only part of the equation, ultimately it comes down to your ability to synthesize high-level concepts and craft a compelling case to justify your opinion.

3. What is one word of advice you have for aspiring VCs?

Start networking early. While it is important to be able to make decisions and understand the technicals, a large part of VC comes down to who you know. In Toronto especially, the ecosystem is super small and everyone kinda knows each other. At Ripple, we’re known for bringing founders and funders together, and in my opinion it is one of the most effective ways to build relationships. You never know who you’ll meet, and when you’ll cross paths with again.

It’s a relationship business. People in the ecosystem are usually 1–2 degrees of separation away from each other, and people talk. Companies or people alike, we invest in lines, not dots. Showing progress, both the ups (and downs) of your journey is valuable to our understanding of your story, and why we should take a bet on you.

Katie is currently an Analyst at Ripple Ventures, an early-stage venture fund focused on leading pre-seed and seed stage investments ($250K to $1M) into enterprise software, developer tools, and web3 infrastructure companies.

Previously, she worked in product roles at start-ups such as UserVitals & Bindo.

About RippleX Fellowship: The RippleX Fellowship is a 12-week extracurricular program powered by Ripple Ventures that runs every school semester.

Throughout each cohort, students are coached and taught the intricacies of startup building and venture capital. It connects students all across North America with a common interest of becoming better equipped as founders, VC’s, and employees at startups. It builds the skillset, knowledge, and network that otherwise are rare to acquire as a student.

#2 🇺🇸 Blake Weissman (Hawke Ventures)

  1. How did you begin in VC?

This cold email started my career in VC.

I was building a non-profit organization at the time that was gaining fast traction. The work we were doing was more important than my schoolwork and I wanted to get credit instead of flunking out of school.

So, I cold emailed twenty professors from the University of Michigan asking to move an independent credit study program forward. Only one got back to me. After reading the email I sent to him, he said.

“Do you have time tomorrow for a call?”

At the time, I had no idea what venture capital was. I wasn’t focused on getting a summer internship or job like my peers. I was more focused on building this non-profit to great heights.

That one call turned into a lifelong friendship with that professor, now mentor, and confidant. After a few months of building together, he sat me down in his office and told me that if I wanted to make real positive impact in the world, I needed to get my feet wet in the for-profit space.

Let me make an introduction to a former student of mine. He runs a VC firm. Maybe you can do some work with him while you build.

And just like that, my VC career was off to the races.

2. What is the most important skill when breaking into VC?

Getting an email like this is my dream scenario. It’s a perfect intro. This intro helps me along my journey of building a more equitable VC ecosystem. It’s aligned with my personal thesis, it’s made my life easier, and there wasn’t anything expected in return.

I had an investor friend from Capital Factory who would put his hands together in prayer when he was asked about people he didn’t know that would forward him deals that fits his firm’s thesis with an offer to intro. Couldn’t be a better scenario when someone goes out of their way to help you reach your goals.

The investor’s main incentive is finding and cultivating high quality deal-flow. That’s what’s going to make or break the fund for the short and long-term. There’s never a shortage of high quality deal-flow and if you find one that a VC can explore, send it over to them.

The skill is to do it in a way that grabs their attention, is relevant, and actionable. After asking some VC friends about what the best case scenario is when someone sends them deal-flow, the common consensus I’ve been hearing is a company that’s aligned with the thesis, three convincing points, their deck, and offer to make an intro.

For example, let’s say you just went to a conference, met a founder whose raising funds and now want to put them in touch with a VC.

Hey, I know your fund invests in AR/VR seed companies between $500k-$2M. Met a founding team while at a conference that fits your thesis, they’re raising, and the previous team has two exits in the same industry. Here’s the deck. Happy to make an intro.

Imagine you do this process and offer to make 10 intros a week. Something will probably land after a period of time.

I haven’t done this personally. So I’m not going to offer advice that you should specifically do this. However, I know that you making their job easier by providing high quality deal-flow is more likely than not going to help you get a foot in the door.

3. What is one word of advice for aspiring VCs?

Build ecosystems.

Photo by Guy Bowden on Unsplash

Blake Weissman is the co-founder of the Hawke Ventures Fellows program that has helped underrepresented professionals land venture-related jobs, totaling up to $650k in salary earned. He has been featured in the press for his work helping promote Black-Jewish relations and now has built BackpackVC LLC to service fellowship programs for professionals interested in breaking into various financial industries like venture capital.

He has a BA from the University of Michigan and is currently living in Israel. If he’s not befriending like-minded collaborators to build high quality venture ecosystems, he’s studying his Jewish religion and spending quality time with friends and family.

The Hawke Ventures Fellows Program is a 12 week program that helps equip the world’s most talented underrepresented professionals with the tools to succeed in venture capital where they build high quality relationships with vetted students, experienced venture capitalists, and learn the skills of a venture analyst that apply to first time fund managers, aspiring venture capitalists, entrepreneurs pre-raise, and startup ecosystem builders looking to scout.

#3 🇺🇸 🇬🇷 Isabella Mandis (Girls Who VC)

  1. How did you begin in VC?

I have been interested in technology for as long as I can remember. In middle and high school, I was involved with Girls Who Code and supported them as they developed their curriculum for younger students. I realized that while I am interested in the space, I did not want to be a software engineer. I started working at different startups and loved that experience. That was when I knew I wanted to be involved in the entrepreneurship space.

I then started reaching out to more founders and scheduling calls with them to learn about what they were building. I had always heard of venture capital but did not know much about it. As I started to do more research into the field I learned that I was basically sourcing for fun.

When I got to Harvard I joined the Venture Capital Group and the MBA Fund. These were my first hand-on experiences both sourcing and actually investing. I started to reach out to female venture capitalists for mentors and was looking for a community of young women similar to me who wanted to enter the field. When I couldn’t find it, I built it. Girls Who VC is now the first organization dedicated to bringing young women into venture capital!

2. What is the most important skill in VC?

So much of Venture Capital is networking — whether it be people in the field or startup founders.

There are so many resources to learn about new startups. Familiarize yourself in the space. Then, start reaching out to founders and hear about their companies. Keep a list of the companies you speak to, the founders, and what your thoughts are. But don’t stop there, also reach out to venture capitalists to hear their thoughts on the space or specific companies.

Being outgoing is such an important skill: reaching out to people, scheduling calls, and then being active and engaged in them. Once you start meeting with founders and learning about different sectors, put your ideas out there and make them available to the public, whether it be through Twitter, LinkedIn, a blog, or a newsletter.

3. What is one word of advice you have for aspiring VCs?

Photo by Noah Näf on Unsplash

My advice I have for aspiring Venture Capitalists is to be unique. Venture capital firms are much smaller than companies in tech, banking, or consulting. They want each person on the team to bring something unique to the table.

It is important for you to develop a niche that makes you stand out from other people. Maybe you know a lot about a specific industry, maybe you know a lot of startups, maybe you created a startup so you can help portfolio companies as they grow. Whatever it is, make sure you think about what you are bringing to the table and how you can add value to firms.

Isabella Mandis is the Founder and CEO of Girls Who VC, and a student at Harvard concentrating in Statistics with a focus in Data Science, with a secondary in Education. She is passionate about entrepreneurship, technology, and education.

Girls Who VC is the first organization dedicated to increasing the number of women in venture capital. We are forming a pipeline of talented and motivated young women ready to enter the field of venture capital with the educational resources and mentorship we provide. We offer education (programs + content), community (networking + support), and access (training + internships. We produce content 6–7 times a week and have events with women in VC every other week.

Join our community! https://www.girlswhovc.com/get-involved
Subscribe to our newsletter!
https://www.girlswhovc.com/newsletter

Follow us on social media! @girlswhovc

#4 🇺🇸 Michael Retchin (Pillar VC)

  1. How did you get involved in VC?

About six years ago, I was not familiar with the concept of biotech. I just knew that I really liked genomics and startups. I wondered if there was an intersection between the two.

I decided to make a list of companies I found most interesting. I found the emails of all the key executives and cold emailed all of them. I went a step further, and emailed their investors, too. In all, I emailed about 200 people. I said: I exist, and I am interested in biotech.

Photo by National Cancer Institute on Unsplash

I was amazed that anybody responded. I got connected with Nick Plugis, an associate at Flagship Pioneering, which is a venture capital firm that starts and invests in their own biotech companies, including Moderna.

From the moment I met Nick, I knew he was someone with a lot to teach me. After he quizzed me on CRISPR, RNA, and machine learning for about a half hour, I asked for an internship.

So he asked me: What do you want to be doing in 10 years?

I said: I’d like to start a biotech company.

What about in the next 10 weeks?

I figured I would get him coffee and work on spreadsheets. Then he asked me a question that I still vividly remember:

Do you want to start a biotech company with me this summer instead?

I instantly said yes. That summer, working with Flagship partner Avak Kahvejian, we created the very beginnings of what would become Cellarity. I would continue building Cellarity with Nick and Avak through the Series A fundraise. I then decided to pursue a graduate degree.

Six months after leaving Cellarity and planning for that pursuit, I was a visiting researcher at MIT. There, I introduced myself to everyone: “Hi, my name is Michael. Nice to meet you. I am hoping to start my next biotech company. Who should I talk to? Who’s the best person on campus?”

And they all pointed to this one guy named Tony Kulesa. So I met him for coffee.

Now, a brief tangent: Tyler Cowen and Daniel Gross’ book Talent: How to Identify Energizers, Creatives, and Winners Around the World is a kind of field guide to finding extremely talented people. How do you know they’re really talented, exceptional?

One of the main identifiers in Talent is when people seamlessly coin original language to describe their ideas. In retrospect, this was something that Tony was doing a lot — creating very interesting ways of looking at the world. Specifically, a new vocabulary for understanding biotech innovation.

Tony was starting a new venture incubator called Petri. The idea was to give small checks, necessary services, and mentorship to help biology researchers start and lead companies out of academia. At this point, I had been thinking a bit about learning venture capital. This seemed the perfect opportunity. More importantly, I thought Tony would make an amazing mentor. He’s become so much more, including my close friend.

Petri has since evolved into Pillar VC’s biotech practice. We lead seed rounds of pioneering biotech companies, typically as their first venture financing. Because we’re scientists and former founders ourselves, we like to roll up our sleeves and help founders recruit advisors and employees, set up lab space, plan for scientific and technical milestones, subsequent fundraising, etc. Whatever the founder needs, we’re there.

2. What’s the most important skill when breaking into VC?

The most important and differentiating pieces are your knowledge and your network.

If you break down the job of VC, it’s 5 or 6 things: marketing, sourcing, diligencing, picking, winning, supporting. Winning means earning the right to invest in a company, which might be a bit counterintuitive. It’s this step that only a venture capitalist can do, because you can’t win a deal if you don’t have money.

Everything else though, you can do that without being a VC. You don’t have to be employed at a venture capital firm to do any of those things.

For example, when I see a really cool paper, I email the authors. But it’s not like I need to work for a VC to do that. I just found the author’s email. Nothing in that is proprietary.

So my advice to very motivated people is essentially just “pretend” (not impersonate) like you’re already a VC. How would you spend your time if you were a VC? Start doing it, part-time. Be intentional. Then write up what you learn. Publish it or send it out to investors for feedback.

3. What is one word of advice you have for aspiring VCs?

People always say build your network. But my advice is to be very targeted and focused when networking. The reason why choices often feel difficult, even paralyzing, is because one has nothing tangible to weigh. They start out nebulous.

This includes the choice of what to do next, how you spend your time. So I recommend you enumerate specific persons you want to meet or even archetypes of persons. You could do the same for the kind of conversations you’d like to have, the kind of relationships you’d like to build, the knowledge you want to gain. Be as specific as possible.

In summary, don’t just set out generally to network and learn, actually be focused. Devise a tailored strategy.

Reach me for specific advice at michael@pillar.vc.

Michael is currently Senior Associate at Pillar VC, helping biotech founders build generational companies. He also leads Nucleate, a global nonprofit that empowers next generation biotech leaders.

He was formerly the president of Columbia Organisation of Rising Entrepreneurs, the largest student society at Columbia.

Michael collates Biotech VC Fellowships & Internships via this Airtable.

#5 🇸🇬 Koh Jia Way (Insignia Ventures Academy)

  1. What made you interested in VC?

Ever since meeting and working with the Malaysian Global Innovation and Creativity Centre (MaGIC team) in its initial days where they brought together the startup community in Malaysia, I’ve always been interested in providing opportunities to the startup ecosystem, whether it is to connect founders to investors, showcase startups, help startups to grow or connecting investors for potential co-investment opportunities.

2. What is the most important skill in VC?

Understanding the industry you are investing in is no longer enough in these volatile times. Being in the VC scene means you will need to be constantly updated with the latest news and understand what it means to you and your portfolio to be able to make decisions in an instant.

You will also need to keep your ear to the ground — subscribe to tech publications (TechinAsia, e27, TechNode, Dealstreet Asia and so forth, or specific publications to the industry of your choice), be aware of market changes and constantly meet the relevant circles.

Photo by Annie Spratt on Unsplash

3. What is one word of advice you have for aspiring VCs?

Be ready to put in the work for your portfolio. Gone are the times when founders accepted funds from any and every investor. You’ll need to figure out what your value proposition is — will you help the founder access a new market? Will you help your founder by connecting them to a corporate client? It is important that an aspiring VC ask themselves — why should a startup take your money and what can you do for them.

Jia Way was formerly the Associate Director of the Business Angel Network of Southeast Asia. BANSEA is the region’s oldest angel investment network and a leader in the promotion and development of the angel investment community.

Prior to that, she was the Program Manager at e27, a platform for startup news in ASEAN; and on the organising team of Echelon — a leading Southeast Asia technology event that draws more than 15,000 visitors annually. Jiaway was also the Project Lead for TOP100 — a regional startup pitching competition for ASEAN’s emerging startups and the project lead for Echelon Connect which facilitates investments into startups.

She is currently the Program Manager at Insignia Ventures Academy — Asia’s first experiential Venture Capital (VC) accelerator to nurture the next generation of leaders, investors and entrepreneurs. VC Accelerator is a 12 week virtual and part time program that aims to help Venture Fellows break into the VC scene, it is now in its 5th Cohort this March 2023 and has had over 100+ graduates from the program.

✋ Hi, I’m Daryl. I’ve spent the last few years working in startups all across the world, deep diving into verticals such as Generative AI & Future of Work and speaking to the very best in the space.

🌐 Across the World in Venture is a repository of articles, where I sit down together with Founders/Venture Capitalists (VCs) across the globe to better understand venture investing in different geographical regions around the world, bringing to light untold stories of under-represented founders and investors.

Always open to feedback and you can reach me via Linkedin or Twitter.

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