What No One Ever Tells You About Becoming A VC

I get asked the same question all the time. Over email, on Twitter, in person. Everyone wants to know the same thing: How did I break into venture capital? Each time I’m asked this question it reminds me how eager I was to find any nuggets of advice that I could utilize when I started on this career journey, and that I should probably write my story down. With each passing year, month, day, and minute it gets a little fuzzier to remember exactly how I got to my current role as an investment manager at [Redacted] Ventures. So, here’s my story.

Before August 2013: My Career Pre-VC

After college, I spent four years working in investment banking at BMO Capital Markets where I served as an equity research associate, focused on the exciting world of real estate investment trusts (or REITs). The final two years at BMO, I started to get more fascinated with the idea of starting my own venture and focused most of my free time on developing MERIT, Inc, a long acronym, that doesn’t really matter now for a startup non-profit which used for-profit technology to match students to their ideal mentor. At the same time, I decided that if I wanted to change the world, I might want to start with getting a business degree. I participated in Management Leadership for Tomorrow’s Pre-MBA program and set my sights on going to business school to become a more skilled and informed entrepreneur. And right after b-school, in 2013, I headed to San Francisco to start my “dream job” at Bridgespan, a leading nonprofit consulting firm.

February 2014: The Turning Point

II had been living in San Francisco for about 6 months and working at the job I wrote about in my b-school essays (see, writing it down does make things come to fruition). However, my dream job quickly turned into a “meh” job where I found myself asking, Why did I take a pay cut? Am I really enjoying this work? After a month of feeling lost, I remembered that I really enjoyed my internship during b-school as a venture capital associate. I thought to myself, Why couldn’t I just become a VC now? I’m living in the mecca of innovation and if there is a place where VC roles would be prevalent, it’s San Francisco and Silicon Valley. I started my job search for a senior associate or principal role in VC.

March 2014: The Search

At the time of my VC job search, I had no clue where to start. Looking back, I would suggest that any aspiring VC first search for secondary sources and resources available online. I later found out that there were many online accounts from VCs and former VCs on the resources they had used in the job search process. But for a guy that never reads the directions before installing electronics, I felt the best way to learn would be by conducting informational interviews and sending in applications.

My first strategy was to reach out to every person I knew from my hometown, educational background, and LinkedIn networks about venture capital and early stage technology investing. I found that my conversations in these initial informational interviews were not that helpful because I honestly wasn’t prepared. So instead of getting real insights and customized direction from people who worked in the field, my conversations were limited to broad topics and general advice for an aspiring VC.I hadn’t taken the necessary time to think about what I was looking for in a VC role (stage, vertical), which would have given people something tangible to comment on or help me achieve.

My second strategy was to apply for each and every VC role I could find. This was also problematic. Candidates for most pre- and post-MBA VC roles are found through the VC firm’s network. Any roles that happened to be posted on LinkedIn, Indeed, or any other job listing welcomed me and thousands of other candidates eager to join the investor ranks. But somehow within my first three months of the job search, where I knew little to nothing about how the VC job process worked, I secured two in-person interviews.

August 2014: The Feedback Loop

Those early informational and job interviews were helpful — not in employment, but in constructive feedback: The consensus was that I was not ready for a role in venture capital. I lacked work experience in technology, and, more specifically, high-tech startups, that would be a key indicator of value as a junior VC. I left many of those conversations with recommendations on what my next role(s) could be to eventually earn a role as a senior VC. As much as the role of junior VC is an apprenticeship, firms are generally very lean in personnel and resources so they search for post-MBA candidates that can really contribute to the success of the fund. They are looking for an individual who has some experience or expertise that can fill a gap in the current team (e.g., the firm is interested in investing in blockchain and therefore searching for a candidate that has worked in the blockchain industry). I was under the impression that venture capital firms were searching for smart generalists (like consulting firms and investment banks) that they could to train to be VCs. That was incorrect.

November 2014: Hitting Pause

I realized early in my search that I couldn’t focus solely on my fleeting goal of becoming a venture capitalist. After hearing from many VCs and growth-stage startups that I wasn’t the right fit (and some just never wrote back), I started applying for roles in finance that had appreciated my skill set before. Eight months after I started my job search, I found myself with an offer from a very large bank in the USA, working for the global risk department as a project manager. It wasn’t exciting, but I took the job anyway. In my free time, I kept looking for VC roles. I also invested in a career coach. I received one early in my search as part of my transition from Bridgespan, but I admittedly wasn’t open to it. This time, I had a “north star” of a career objective and financial resources to pay for a quality career coach. I worked with my career coach for about six months, and she really helped me learn how to frame my career aspirations, acknowledge how my previous skill-building could contribute to those aspirations, and identify the skills and roles that could bridge the gaps between the two.

November 2015: Hacking My Experience (Nov ’15)

During the “design research phase” of my career development and through reading any and every article about VC, I was able to finally discover what VC firms and entrepreneurs were looking for in new VC hires. They are looking for individuals that have a strong network of other investors and talented founders as well as some type of superpower, which could be an operational expertise or industry expertise. This is when I realized my previous experience wasn’t antique trash, but was valuable and I could leverage it in the next chapter of my career. So, I became determined to use my experience to obtain the following: Gain experience helping early stage founders Solidify and display my “superpower” or expertise to the general VC community Get experience assessing startups and tech markets Grow my network of investors and founders as well as my reputation as a contributor to each community

January 2016: My Big Breaks

After I determined what experience I needed, I began to apply to part-time or contract opportunities in congruence with my continued search for full-time VC roles. My first real opportunity was as a startup consultant for the New-Orleans based Camelback Ventures. I had met the founder through a friend a year prior and he reached out to me when they were looking for candidates for the role. I was really interested in the role because it would give me hands-on experience with early-stage founders who were looking to leverage technology to solve inefficiencies in the world of education.

I was brought on to assist the four founders, given my experience as both an edtech founder and a nonprofit consultant. I learned so much working with them on product market fit, sales pipeline strategy, the fundraising process, and hiring strategies. Camelback Ventures gave me that opportunity to expand my startup experience outside of MERIT Inc. Once I had experience working with Camelback Ventures, I was able to pitch to other accelerators that operated in areas outside of education, such as real estate and fintech, for paid and unpaid opportunities working with early stage founders. This gave me a glimpse into all the problems that entrepreneurs face in the early days of their venture. Instead of holding those common learnings to myself, I decided to share this content with the general masses of entrepreneurs. I had read many times from VCs the importance of blogging to establish a brand as an investor. But, I initially assumed the activity was a lost cause given that there was so much noise on the internet. But, my perspective was changed after reading from an established VC that an aspiring VC should not view their blog as a popularity contest (i.e., your views and readership numbers don’t matter), but should see it as an extension of his or her resume. At first, it felt like I was screaming into an empty room, but later in my job search, I received compliments on my blog from interviewers; many had read some of my content to see if I had a point of view.

Sharing my content through Medium and Twitter eventually caught the eye of Arlan, the managing partner of Backstage Capital. Backstage Capital is an amazing team of VCs who are focused on investing in talented startups that are led by founders from underrepresented demographics. She reached out to me in early 2016 through Twitter and asked if I would be interested in chatting about Backstage. She offered me a temporary role, which ended up lasting for more than a year, as Backstage Capital’s first Investor in Residence.

This opportunity gave me clear insight into what the role of a venture capitalist entailed. I had the opportunity to do market deep-dives on companies we were conducting due diligence and source deals on behalf of Backstage Capital. I was able to build analytical skills that were unique to venture capital as well as build a strong deal flow from a network of talented minority founders, something that is uncharacteristic of most traditional VC firms.

Once I was able to articulate my experience in advising early stage founders, my expertise in legacy industries, and proprietary deal flow, I realized I still needed to grow my network of current VC investors. I came across John Gannon’s Going VC program. I had become an avid reader of John’s website, which tracked VC role openings and had a repository of VC blog posts and articles on how an aspiring VC could break into the industry. I was a member of Going VC’s inaugural class and got more out of it than I anticipated. I learned how to design my materials and package my experience.

By working for Camelback Ventures and Backstage Capital, while also blogging my perspective and participating in GoingVC, I was able to fill gaps in my experience. I would not be at my current role if it were not for those three organizations.

November 2016: Draft Day

In mid to late 2016, I was still interviewing with venture capital firms. I had done a better job of using “warm leads” from b-school and professional contacts to secure interviews with firms. Even though I was more prepared in my VC interviews this time around, given my teaser decks (which had a portion of my investment thesis) and in person materials (which had investment recommendations), I wasn’t convinced I was any closer to gaining employment in the VC field. Then, I met with [Redacted] Ventures’ entire investment team and presented them with my thesis on the future of commercial real estate tech. I must have done something right because I heard back a week later that I got the offer. It felt surreal to accept a role I had been chasing for so long. However, I acknowledge that I wouldn’t have been able to break into this role if it weren’t for me taking the time to gain work experience in the VC profession and the contributions of my personal and professional relationships. Maybe “breaking into VC” isn’t a true characterization of my journey from non-profit consultant to corporate venture capitalist. I didn’t recklessly break into the industry, but instead I took my time, organized a team capable of helping me secure the “one big job,” and diligently waited for the right time and place to conduct my heist and end up with my sought-after role.

This post was originally published by Earnest Sweat on The Importance of Reading Earnest.