The Antidote to Getting a VC Job: 10 Prescriptions for Aspiring Investors

Preface

Venture capital (“VC”) found me through entrepreneurship. In fact I knew nothing of it until I came across the blogs of early-stage investors Fred Wilson and Paul Graham.

At that time, I was reading everything I could find on startups and technology. I had a small online business I’d founded while at university and was increasingly fascinated by the art of building things (including companies), technology, and the future.

So when I discovered that there was a job where you supported and backed a portfolio of ambitious technology startups, I knew I had to find a way in on the action.

However, I didn’t fit the profile: I wasn’t an ex-operator or engineer. I didn’t work at a top-tier investment bank or consulting firm. I had no MBA. I lived and worked outside of London and my network was lacking.

It would take 5 years of stepping stones, career experiments, and what at times looked like unfocussed meandering to others, before I eventually landed a role as an Associate at Downing Ventures.

I now get asked almost every week for advice on how to get a VC role. I often hesitate in sharing much, mainly because I’ve only done this once and what works for one person at a certain time won’t necessarily work for others.

That said, I get the VC career question so often and since I’m keen to help more people but can’t always meet individuals for coffee or take calls with them, I decided to weave together a comprehensive blog post on the topic that can provide guidance at scale.

To be more helpful, this article takes account of experiences beyond my own and includes anecdotes of both prominent and lesser known investors. But be warned: there is no sure-fire path to a VC job. Fortuitous circumstances and luck play a substantial role and this is mostly beyond our control.

However, if you reflect on your aptitudes and experiences, complete this Guy Kawasaki test yet remain driven, and know for sure that that even if it takes 3 to 5+ years to get there you are willing to pursue a VC career, then this blog post is here to help you get started.

Introduction

A job in VC is highly coveted. It’s one of the most impactful professions (Apple, Google, Tesla, Amazon, and Fedex were all VC-backed) and it can be highly rewarding but it’s also one of the most competitive to crack.

Today there are countless guides on how to break into the industry and with global venture investment at record highs (over $254bn deployed in 2018 alone — the highest since the dotcom bubble!) hiring in the sector has picked up pace.

Make no mistake though, the venture industry is still tiny and employment is sparse. In the UK, for example, there are 170 active firms (up from less than 50 a decade ago) with only 1,400 investment professionals in the country (the USA is around 6x that amount.)

At any one time there are a few dozen vacancies advertised in the UK in addition to roles that are barely public and are filled through referrals. Contrast that to the legal profession, which has close to 10,000 firms in the UK, employs some 100,000 lawyers, and at any one time has thousands of job vacancies.

Getting a VC job certainly takes some luck and if you’re an outsider, you’ll have to work doubly hard. Nonetheless, it may be possible over the long term to cumulatively stack the odds in your favour for a snowballing advantage, but even then, I wouldn’t recommend you entirely stake your career happiness on getting a role in the sector.

More realistically, and as you will see with Prescription 10, you are better off being open to a wider range of career possibilities because if you have what it takes to work in VC, you can still find fulfilling work in other domains.

The Antidote

So how does one to get a job in VC? In some ways you have to do exactly the opposite of what you would instinctively want to do. Most VC job guides provide tactical steps (join a startup, attend events, network with entrepreneurs/investors etc), which is no doubt useful — and you’ll get some of that here too — but considering tactics in absence of higher-level strategic principles inspires a short-term mindset and plays to our craving for quick fixes and easy wins.

This post provides an antidote to our instinctive desire to seek ‘the easy path’, which doesn’t really exist. My hope is that this guide will alleviate false assumptions on how to get a VC job, all the while leaving you better off by inspiring long-term ideas on what you can do to pragmatically improve your chances.

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The 10 Prescriptions

What follows is a list of 10 prescriptions of what I’ve observed as effective from the VC career paths of investors in the UK and USA. It’s impossible to excel at all 10 things (I struggle with a few myself) but if you can excel at a few and do the rest of them reasonably well, you’ll stand out and have a better shot at making it.

As you read the prescriptions, be sure to keep in mind what a VC job entails— i.e. (1) finding attractive investment opportunities, (2) earning credibility and trust with the best founders so that they invite you to invest in them (3) helping those founders succeed—and consider what you can do to develop the skills necessary for the job even before you have it.

In no particular order, here are the 10 prescriptions:

1. Don’t ask for help. Be the helper. Don’t be extractive and transactional. The venture community is small and a venture career is long. Find ways of helping others do well. “It’s easier to win if everyone wants you to win,” says Randy Komisar of Kleiner Perkins. And helpers tend to have this effect on people.

So help founders, help investors, and do what you can to support the tech and entrepreneurship community. Least of all you will feel good doing it, but do help even when you expect nothing in return.

A word of caution though: don’t revert to a VC trope and end every meeting with a disingenuous “let me know how I can help” when you don’t really mean it. Find things you can actually help with, while giving consideration to your existing commitments.

Case Note: Prior to joining Backstage Capital London, Andy Davis was already going above and beyond for founders. He built an intimate community of black tech entrepreneurs based on regular meet-ups he hosts and it has grown through word-of-mouth on the value it brings to members.

Andy was helping founders with business models, pitch decks, introductions, and fundraising all before he was recruited to join Backstage Capital. His contribution to the tech community was so evident that whichever fund hired him, it would be partnering with a true value-add individual.

Further Reading: Give and Take.

2. Don’t cold contact. Build relationships. Some people spray-and-pray templated LinkedIn messages, emails, and generically try to cold contact people they don’t have any connection with. Sure, some of these messages will get a response but many get ignored given the volume of inbound messages that investors receive.

So avoid cold contacting where possible. If another trusted individual can introduce you instead, that will get more attention.

How do you get “warm” intros? By building long-term relationships. Someone you’ve met once is unlikely to introduce you with any credibility to their network. But someone you’ve passionately discussed ideas with at an event, or perhaps someone you’ve worked with on a project or socialised with — that person will be more willing to credibly connect you to interesting contacts.

Case Note: There’s a philosophy in tech entrepreneurship about starting a company by doing things that don’t scale. It takes more work but if at a small scale you can “recruit users manually and give them an overwhelmingly good experience,” writes Paul Graham, you’ll find that “it’s like keeping a fire contained at first to get it really hot before adding more logs.”

The same can be said of a personal network. Starting small but with depth is more impactful than networking wide but superficially.

Here’s Ana Díaz Hernández recalling how she landed a role at Kapor Capital:

“I fostered a personal connection with partners at the firm. I met Mitch Kapor and Freada Kapor Klein through mutual interests in advancing diversity in tech and began to learn about the great work they did through Kapor Capital and the Kapor Center for Social Impact.

As a Latina in the startup world, the diversity work of the Kapor Center was very resonant. I had been interested in venture capital for a while, but it was our relationship, our values alignment, and the desire to work together on advancing social impact in technology startups that got me to join the team.”

Further Reading: Never Eat Alone. Also see Friends as Ends in Themselves.

3. Don’t be interested. Be interesting. Everyone that applies for VC jobs says they are interested in technology and entrepreneurship. However, that’s table stakes and it doesn’t say much about you. To stand out, you have to evidence your interest and passion by doing things that are interesting.

Instead of just reading TechCrunch, following VCs on Twitter, and listening to tech podcasts, invest time in doing things that without a doubt evidence the depth of your passion and interest in technology and entrepreneurship.

I can’t prescribe exactly what you need to do here but there are some rules of thumb that can help you identify opportunities that will serve you well. The chosen activity or venture should ideally:

• quench a personal curiosity;
• require significant time investment;
• contribute to a discussion or topic entrepreneurs and investors care about;
• be relatively original.

Case Note: An inspiring example here is Jenny Gyllander. At university, she conducted 18 interviews with VCs for her 110-page thesis titled:

‘Dear VC, now it’s your turn to pitch’ — an exploratory study on Venture Capital firms’ brand and reputation.

Clearly Jenny’s interest went beyond what most people who are ‘interested in VC’ do, and it didn’t stop there.

After university, Jenny worked at a design agency before joining Slush, one of Europe’s largest tech conference organiser. She was quickly promoted to CMO thanks to her impact and some years later she was recruited by the team at Backed VC.

Even though Jenny had now joined a VC fund, she continued to explore her interests with depth. This eventually manifested through a side project called Thingtesting, a dedicated Instagram channel to discover and showcase emerging direct-to-consumer brands. With over 25k followers on the gram, Jenny has since turned Thingtesting into a full-time job.

Further Reading: Pick the Idea That’s Craziest.

4. Don’t “pick brains”. Present theses. Remember Prescription 1? Many people violate it by cold contacting investors and asking to pick their brains over a coffee. This is a bland way to connect with someone if you are looking for career advice and help. Most investors ignore these one-sided requests.

A better way is to reach out (ideally via a warm intro) with a specific topic that is relevant to the person you would like to connect with. For instance, has the person recently announced a deal in an area you’ve been tracking and you have ideas to share on how it will develop?

Consider reaching out to people with a view to share knowledge and engage in discussions. That’s more compelling than ‘can I pick your brains?’

Case Note: Before getting into VC, Andrew Chen shared his startup knowledge by authoring hundreds of essays online. This got the attention of one the founders of A16Z, which eventually recruited him to join the fund. As he remembers:

“I moved to the Bay Area in 2007, as a first time founder with a lot of energy and a lot of questions. I spent the first year meeting everyone I could, reading everything about tech, and writing down all that I was learning. A few months in, I was shocked to get a cold email from Marc introducing himself. Who knew that sort of thing happened? My blog was pretty much anonymous and I could be anyone — but he reached out to talk ideas, which made a big impression.”

Further Listening: Inventing the Future with Josh Wolfe.

5. Don’t apply online. Get referred. Job postings in VC get many hundreds of applicants within a short time of being posted. And these applicants are far from average. They are smart, ambitious, and often have compelling work experience. Standing out in a swarm of cold but truly exceptional CVs is challenging. And even if your CV does get attention, the document rarely conveys your story in its truest and best light.

While I wouldn’t completely rule out applying online, if you are following Prescriptions 1 and 2, you will be in a better position to first seek help from people who know you well and who might be able to connect you to a particular fund that is hiring.

These people can help surface your CV by referring you, thereby making a recruiter’s job easier. After all, if a trusted party can vouch for you, it saves hiring managers time from filtering through hundreds of other CVs.

To be worthy of a strong referral, see Prescriptions 1 through to 4, and invest in demonstrating that you have the potential to do well in VC.

Case Note: Legendary investor Bill Gurley of Benchmark got his break when a newsletter he wrote on the tech industry caught the attention of a well-connected investment banker. He recalls:

“Frank Quattrone [the investment banker] called me out of the blue and said, “We’re leaving Morgan Stanley, we’ve heard a lot of things about you, we want you to join us.”

Frank and I had a long talk, and he said, “What do you want to be long term?” I said, “I’d love to be a VC.” He said, “Come to work for me, I’ll move you to Silicon Valley and introduce you to every venture capitalist that I know.””

Bill subsequently went off to work as a tech analyst for Frank Quattrone. And sure enough, his work efforts and network paid off with referrals that launched his VC career: Bill Gates referred him to the VC fund Hummer Winblad, which he joined briefly. Then Frank Quattrone introduced him to Benchmark, which he joined in 1999.

Further Reading: How to Be Great at Your Job.

6. Don’t be an expert. Be a generalist. If you are early in your career and break into VC, you will likely start out as an Analyst or Associate, in which case a fund wouldn’t expect you to join guns-blazing as an expert in a specific area. You will still have much to learn and be expected to work across a wide range of tasks.

So at least initially, you’re better off starting with a broader set of experiences. Not only will you better relate to founders across several business functions, you’ll get to know yourself better, with a wider range of experiences about what you could be exceptional at. Once you’re a more experienced investor, you can use this knowledge to help further your specialism.

Is there a generalist skills palette that can serve you well coming into the VC industry? Once again, there is no formula but a foundational understanding of all the following is a good start:

• Sales
• Finance
• Marketing
• Product
• Communication
• Psychology

Case Note: Mary Meeker, author of the popular annual Internet Trends reports, is arguably one of the greatest technology analysts of our time and yet her path did not evidently start with any core specialism:

She studied Psychology for her undergraduate degree and then expanded her repertoire by doing an MBA — a mostly generalist business degree — with some specialism in finance. She then went on to work at a number of investment banks before joining the VC fund Kleiner Perkins (she now runs her own $1.25bn fund).

Today, Mary Meeker is seen as an expert on the Internet but I have no doubt that her exposure to psychology, the MBA, and her analyst roles at investment banks made her a better investor. This is why, as a Fortune magazine reporter once put it,

“…she is absolutely first rate when it comes to spotting big-picture trends before they come into focus. She gathers massive amounts of data and assembles it into voluminous reports that, while sometimes rambling and overambitious, are stuffed with a million jumping-off points.”

Further Reading: How to Fail at Almost Everything and Still Win Big.

7. Don’t learn startups. Learn to learn. It’s important that you don’t just spend all your time reading startup advice. Go a step further and first learn how to learn. Sarah Tavel of Benchmark nicely sums up why this is important on her blog:

“In VC, you’re constantly ramping up in a new area. Each company you evaluate brings with it its own ecosystem that you need to understand. Similarly, trends in the tech ecosystem turnover so quickly, that if you ever stop adapting and learning, you’ll quickly become a dinosaur and won’t know a Snapchat when you meet one. That drive to constantly learn will help you adapt to new environments and challenges.”

So work on strengthening your learning capacity. This will help you pick up new ideas and concepts with speed. Some of the best investors have this down pat. Like investigative journalists, they know how to traverse a new area, speak to several experts, and distil the essence of what was previously unknown in order to make an intelligent investment decision.

Case Note: A brief personal story is worth sharing here. By the time I became a venture capitalist, I’d exercised my learning muscles to a point where I was comfortable (and in fact quite relished) the challenge of having to learn new things often and with efficiency.

I did this first through hobbies: learning to skateboard, learning to play basketball, learning to make music. Then academically: learning how to research, learning how to write. Then in business: starting an online business, learning and reading everything I could find on entrepreneurship, and doing an MBA.

With each learning journey, I picked up key ‘learning’ lessons that I continue to use to this day. No doubt I still have someway to go in getting better at this, but by learning lots of new things prior to my VC career, I found the transition to a fast-moving industry less jarring.

Further Reading: Ten Simple Rules for Lifelong Learning, According to Hamming.

8. Don’t be a critic. Cheerlead and build. Being a critic is easy. In fact it’s more tempting to be a critic when you’ve never built anything of substance yourself. You may also find it harder to relate to entrepreneurs who are building hard things. In addition, being more of a critic than a builder makes it difficult to engage your creativity, which you especially need when assessing novel ideas.

To get around this, spend more time with entrepreneurs and look for ways to support and act as cheerleaders for them (see Prescription 1 again.)

Secondly, work on building something new yourself. It doesn’t have to be a business by the way (I build books). But it should be something new, and with the potential to be of value to others.

Naturally, this thing will also be vulnerable to criticism and rejection, something entrepreneurs have to face daily. But by building something new, you’ll flex your creative muscles, which will make you stand out from all other aspiring VC candidates.

Case Note: June Angelides is an investor at Samos VC but before that, she built something of significance outside of her day job at Silicon Valley Bank.

While on maternity leave, June founded “Mums in Technology”, a child-friendly coding school that taught over 250 new mothers how to code and in an environment where they could bring their children along.

June built “Mums in Technology” out of a genuine need to fill a gap she spotted and felt a deep care for. She didn’t build it to get a VC job but incidentally, her experience of building things no doubt contributed to her being recruited by one of the UK’s leading VC funds.

Further Reading: Originals: How Non-Conformists Move the World.

9. Don’t covet venture capital. Learn its downsides. Like any other job, there are things that investors don’t like about their work. Yet, the best candidates for the profession—and probably those who will have a longer-term career in the industry — take time to understand and accept these challenges.

What makes being a VC hard?

For one, it’s very difficult to make money as an early-stage investor. And then there’s a psychological toll to pay: saying “no” to most of the founders you meet each week can be dispiriting; working through several company failures is anything but simple; and, as Max Levchin (co-founder of Paypal and a serial entrepreneur) puts it, “you have to work relentlessly for ten years just to determine if you’re any good at the job.” (Note: there are some ways of getting shorter feedback cycles.)

Furthermore, starting out as Associate can be unstructured (unlike other professional careers) and all-consuming. However, if you can be cognisant of the downsides and your enthusiasm for a career in the sector remains firm, VC could be the right profession for you.

Case Note: Max Levchin is a well-known serial entrepreneur. He co-founded Paypal, Slide (sold to Google), and at the time of writing is the CEO of Affirm.

Like many successful entrepreneurs before him, Levchin considered a career in a VC after founding and exiting his businesses. But it wasn’t long before he realised that VC wasn’t for him. Here’s an excerpt from an interview the journalist Gary Rivlin conducted with him:

“…Levchin recognized he wasn’t venture capital material. He had practically birthed Yelp in his offices in the mid-2000s and provided the online rating service with its early seed money — and then felt he was the “helicopter parent” that no entrepreneurial venture needs early in its life.

“I remember very distinctly a moment when I thought, ‘Why don’t you get out the way and let me drive this car now?’ ” he confessed. “I was becoming the investor no entrepreneur wants: the guy everyone is wishing would stop with advice and unwanted help.”

Levchin had a similar experience after providing seed money to the founders of Pinterest, the digital scrapbook site. “I’m self-aware enough to know I’m clearly too tactile to be a venture capitalist,” Levchin said. “I really want to be the one doing the building and not offering advice from the sideline.””

Further Reading: Becoming a Venture Capitalist.

10. Don’t pursue a VC job. Plant seeds of possibilities. Victor Frankl put it best in his timeless classic, “Mans Search for Meaning”. In writing about happiness and doing well in life, he notes:

“Don’t aim at success — the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s personal dedication to a cause greater than oneself.”

I appreciate this quote has whiffs of impractical idealism. Yet, there’s something in it for aspiring VCs too. Indeed, those who have the best prospects of getting a job in the sector often aren’t the ones directly applying for VC roles. They are busy doing things—many of which I’ve shared in this blog post—that make it more likely that an opportunity in VC will ensue.

So don’t try to pursue VC jobs directly. Instead, help people in the tech ecosystem, build genuine relationships, do interesting things that pique your curiosity, share your ideas widely, build foundational competences in key business functions, learn how to learn, and build something with some significance.

Doing these things might not necessarily get you a VC job, but they will most certainly plant seeds of possibilities that will open doors to a wide range of fulfilling careers.

Some Parting Words: VC attracts people who are curious about business and technology; people who thrive in varied and dynamic environments where the learning never stops; and people who, fundamentally, enjoy working with other ambitious people.

But VC isn’t the only career choice available to such people. These same themes — business, technology, learning, ambition — can be found in other jobs too. So as you cultivate what it takes to be a VC, I would encourage you to keep an open mind to non-VC opportunities where your talents could be just as fruitful.

Further Watching: Why Greatness Cannot Be Planned: The Myth of the Objective

Special thanks my venture friends, Check, Jayanth, Kathy, and Matt, who read an early draft of this post. And shout out to Albert Wenger, who helped guide my early thinking on a venture capital career and purpose.