The Role of Mentorship in Venture Capital


Today we are tackling the subject of how mentorship works in venture capital. Steven Cook of  Chicago Ventures contributed his thoughts, which are highlighted here, as well as are the firsthand accounts of Rakith (Jay) Jaywardene, our current intern, and a senior at Case Western Reserve University.  


An Apprenticeship Business

Steven confirms how essential mentorship is to the success of any VC endeavor. Specifically, Steven compares it to an “apprenticeship business” of sorts: “At the end of the day, venture is very much an apprenticeship business. You can learn as much as you can from the outside looking in, and of course, having experience working at startups and working in the tech world definitely helps, but there’s just a lot of nuances to the job that really takes experience to understand.” And to get that experience, Steven added, “It’s really important to have solid mentors who can give you that guidance when you’re coming into a situation for the first time.”

If that experience comes specifically from someone who has been both on the operating and investing side of the VC table? All the better, according to Steven, “It just accelerates your learning and ability to adapt and be successful in this environment.”

Steven added: “It’s hard to be successful in this world without a mentor. You can pay your dues and go about your business on a daily basis, but unless you’re seeking out that advice, then it’s really hard to grow and really build a career.”


Beyond The Basics

When you think of internships, sad images of newbie drones relegated to the exiles of photocopying, getting coffee, taking lunch orders, and the like may come to mind. This is the exact opposite of what a mentorship should entail.


According to Jay, Refinery Venture’s current intern, the hands-on, in-depth experience of a mentorship made all of the difference: “I was very lucky and fortunate to have the opportunity to actually have a say in a lot of the deals that we were considering… Just to have the ability to have a say in something, rather than just due diligence and data analysis, is something that’s been critical.”


Also proving priceless? Challenging conversations and real-world experience. “[One-on-one time] has been a tremendous gift, [allowing me] to be able to really get Tim’s perspective on any of the questions that I have and just really understand what his thoughts are in broader terms on the industry and the dynamics of the industry today.”


So, what advice can be given to both the mentor seeking a mentorship and the mentor deciding who to invest their valuable (often limited) time into?


Steven says that, first and foremost, studying the industry needs to be a priority for hopeful mentees. “I think the people who are most successful in these types of roles are people who just have a genuine curiosity for how the world works.” And the best way to do this? “Start studying the industry, read the blogs, read the books, start networking with people who are in the industry, ask them to connect you with other people… that snowballs into many different opportunities, whether that’s internships or jobs or just getting to know interesting people and making connections that will be valuable later.”


It’s A Small World, After All

Once that proverbial ball gets rolling, according to Steven, it just flows from there. “Once you get inside this [VC] world … it’s pretty easy to get to know a lot of the different investors.” Steven states that, “once you connect with somebody, they’ll connect you to somebody else, who connects you to two other people and you get to know people.”


Jay offered this advice regarding networking that they’ve found to be fruitful as well: “I think before networking even occurs, someone has to find a way to show that they could provide value or provide an opportunity to ask insightful questions.” This could include reaching out to people through channels such as LinkedIn, thus allowing you to show visually that you are interested in the space and have put the time and effort into understanding the area through personal projects or club experiences or work experiences of some nature.


Steven shares some further advice for hopeful mentees approaching their desired mentor: “Make it as personalized as possible, really demonstrating that genuine curiosity about what’s happening in the venture world.”


Take Two, Or More

Another thing of note that many do not realize is that mentorship does not have to be limited to a single pairing. Throughout your VC journey, as you evolve and learn, you may have many mentors along the way, each of who will most likely be wearing a different hat and fulfilling a different role. Some may have official advisory roles, for example, whereas others could simply step into that mentor role by answering questions. Both are incredibly valuable. In fact, in their own way, one could look at it as everyone in the VC realm—from the youngest to the most seasoned—could (and should) take on some sort of mentorship role in some kind of way.


Choose Wisely

And for mentors, how do you pick and choose who you’re going to mentor? Steven says to look within your network. And, of course, they have to have that vital “genuine curiosity,” which Steven explains is often the biggest indicator of success in the VC world.


Finally, as an inspiring call to action, Steven leaves us with a list of podcasts that he has personally found to be useful along his VC journey. So whether you are now in the mentor or mentee role (and some of you will be in both simultaneously), do not hesitate to avail yourself of the following information, then go forth and make VC magic.

·      Acquired

·      Invest like the Best

·      Venture Stories

·      16 minutes podcast by a16z

·      NFX Podcast

·      The Consumer VC

·      The Full Ratchet

·      Recode Decode