Lifting the lid: How the Playfair team got into Venture Capital

Chris Smith
Playfair Blog
Published in
13 min readApr 29, 2021

TL;DR We know that our industry can be somewhat opaque. So in this post, each member of the team reveals the story behind how they came to land their role at Playfair. We hope it will be helpful for anybody looking for a career in VC.

Warning: this is a long post so grab a ☕ or 🍺 and settle in

Joe (Partner)

Note that this is written in the third person since Joe is currently recovering from wrist surgery — thanks Khushi for typing it up 🙏

Three months before joining Playfair, Joe had absolutely no idea what Venture Capital was. He was working as a technical recruiter at Facebook at the time, hiring Software Engineers for European roles — and, evidently, trying on snowmen costumes :)

One of his mutual friends had interviewed for Playfair’s head of talent role with no success and chose to refer him to the role. It was on his first call with our founder Fede that Joe first learned what Venture Capital was, and why the head of talent role was necessary.

At this point, Joe had been certain he wanted to join a startup and move to London. The idea of getting lucky after working for a company that eventually became a massive deal was really attractive to him. Until — Fede convinced him that trying to pick a single winner would be risky, and it would work much better to hedge one’s bets on a few different startups. That argument made a lot of sense to Joe, and he started in March 2015, as the fund’s Head of Talent.

The core job description he had here was to help founders in Playfair’s portfolio do all things talent related. This is where he applied the evidence-based HR approach that teams he had previously worked with had appreciated so much. Having observed Google and Facebook’s approaches carefully, Joe had become obsessed with the science of personnel selection and brought his academia-sourced methods to support our portfolio companies in their hiring decisions. Almost always, this meant sourcing engineering talent and successfully filling open roles with the people he found.

Not long after Joe had joined, the investment team was diligencing a deal that they were 50/50 on, and Fede asked Joe to meet with the founders to give his perspective. After flipping through the deck, he noticed that the cofounder spoke about having significant experience building and managing teams, so he asked a few relevant questions as part of the meeting. Ultimately, Joe was able to give this feedback to the team and support a pass decision that was otherwise really challenging to make.

That was Joe’s first experience being an investor without really realising it. From that point on, he became an integral part of the due diligence process at Playfair, digging into founders’ ability to build teams or coachability for building teams — very core attributes for successful founders. 3 years ago when the investment team was under-resourced, Joe officially joined it and spent half his time doing all things investment related (taking pitches, leading deals and more), with the other half of his time focused on talent.

At the beginning of 2019, with the launch of Fund 2, Joe became a partner and continued to go about doing the same work at Playfair. Today, Chris and Joe run the fund day-to-day, but the whole team plays an integral part in the work we do.

Joe’s story illustrates that there truly is no typical path into venture, and building a personal brand around a specific, unique skill set can help you break in.

Chris (Partner)

It was early 2018. I was living on the Isle of Man and had been at plan.com for a little over 4 years. With my girlfriend (now wife) returning to the UK for work and the learning curve starting to flatten I was thinking about what to do next, although had no immediate plans to leave.

During my research, I came across John Gannon’s blog and registered for his newsletter. I didn’t expect to find much, but then on 13th May 2018, a listing appeared which would change the direction of my life.

A rare opportunity to join a fund as a partner

I actually saw it a few days after it was posted and since most VC jobs get 100s or 1000s of applications, I didn’t fancy my chances.

A quick look on LinkedIn and I found that one of my angel investment founders — Ben — was connected to the Managing Partner at Playfair — Georgia. I asked for an intro and Ben kindly obliged. This lead to a first call with Joe in late May 2018.

Isle of Man problems

Crouched down in a car park to shelter from the 70mph breeze that day (that’s right, that’s not even windy on the IOM), I told Joe about my experiences building my own telecoms business, slogging away as a lawyer, angel investing and at plan.com.

I obviously wasn’t sure exactly what he — or the team — were looking for at the time, but it happily lead to a face-to-face meeting and a full process.

I spent the next three months really getting to know the team through a mixture of calls, face-to-face meetings, pitches with companies and running a full process on one company through effectively to IC. Unlike many other jobs I’d applied for earlier in my career — mostly in-house legal roles — that I didn’t get, this felt right from the first call and every subsequent step confirmed it. I was offered the job and joined in November 2018 🥳

Looking relaxed and casual as a lawyer 🤦🏻‍♂️

Looking back, it wasn’t the things that most people focus on for most jobs that the team cared about. Academic achievements, a good university, and a strong employment track record were all table stakes. What was far more important was the things I had done outside my academic studies or my day job — things that most people don’t do. Whether it was setting up my own business or investing my own money as an angel, these provided comfort to the team of my genuine passion and curiosity for becoming a full time investor.

My key takeaways/tips:

  • With 100s or 1000s of applicants applying to every role in venture, think about extra steps you can take to get your foot in the door and during the process to be the candidate that stays top of mind. During the process, I sent a deck summarising my angel investments and put together a comprehensive list of references (before I was asked)
  • Venture doesn’t have to be a job you do in your 20s or even your 30s — many people have successful careers in other things first and then use that experience to help founders when they become investors. If you can’t find a job in venture now, go off and do something else you’re passionate about to build experience, then come back in a few years. There is no one right path to becoming a successful VC
  • Be systematic about signing up to and reviewing sites for relevant job opportunities and get in quick— I nearly blew it by being slow off the mark!

Henrik (Associate)

My mother is an entrepreneur. My father is a banker. So I grew up simultaneously thinking about how we can constantly innovate the world around us to create useful new products and build businesses that make money.

This early interest led me down various paths through school, university and my early career before I realised my dream job was at a VC fund like Playfair. I want to explain the journey to this realisation so anyone in a similar position knows what they’re aiming for, regardless of the specific path they end up taking.

Throwback to Series 1

As a teenager, it was the popular UK TV programme Dragons’ Den. Later, while at university, it was founding my first tech startup, RendezVu. Also while at university, I started to put my money where my mouth was by investing small amounts of savings in equity crowdfunding campaigns on Crowdcube and Seedrs. I must have spent literally thousands of hours thinking about problems with current ways the world does things, how I could (theoretically) solve them and whether someone’s business solution had commercial legs.

I’m sure I would laugh today at 99% of my entrepreneurial and investor ideas, but that is exactly the point of this phase: testing your ideas, breaking them, figuring out what makes you tick and what gets you out of bed. I didn’t have a masterplan aged 11 while sitting in front of Dragons’ Den on the sofa of how to ‘break into VC’. I didn’t have that plan until maybe a year before I started applying.

My key advice here is: follow your interests, then see them through.

I went through the same iterative process of figuring out what I wanted to do with my career. Studying French and Spanish at university allowed me to spend a year abroad working in private equity, working for a school to rebuild their website, and spare time to launch a social enterprise to provide better access to Oxbridge for underprivileged students. My conclusions: finance was well paid but placed you in a box you knew the size of; building something from nothing was much harder but more satisfying and had no ceiling.

Only slightly exaggerated

I knew I was heading towards a career where entrepreneurship and finance were inextricably linked. But, I knew there was one major gap. I went to work in investment banking for two years. For me, this was the best practical version of an MBA, supercharged. There’s no quicker way to learn how models and ‘numbers’ work than the ridiculous world of M&A.

One year into banking I knew it wasn’t the long term career for me. My simple question and answer to anyone asking themselves the same question: do you see yourself in your big bosses’ shoes in 10 years? If you shudder, it’s time to change tack. Find someone who’s been ‘successful’ in their industry and who you’d like to emulate, that’s likely the career path for you to follow.

If you’re looking for practical steps on how to start the process of getting that dream job in VC, read on to Jeevan’s brilliant key tips and resources below.

This post summarises my personal journey into VC. It has one key message: figure out why being an investor in early stage businesses gets you out of bed and then be sure it does. There isn’t a playbook for being a VC, it’s not a checkbox for high achievers. We live and breathe the job because it doesn’t feel like work. I honestly believe anyone who has figured this out through personal and professional iteration has also built, along the way, the experience and understanding that will get them a job in VC.

If you’re curious what I thought on day 1 of starting my job in VC, here’s the blog post I wrote when I first joined Playfair back in Feb 2019.

Jeevan (Associate)

At a massive corporate, working with equally massive FTSE100 clients, I was surprised to learn that we had a Commercial Innovation team that worked with startups. Having always dreamt of starting my own business one day, this seemed like the perfect next step.

Presenting for the first time in a room full of VCs

Here, I had the opportunity to see the inner workings of the startup world: I was meeting founders everyday, going to events in the ecosystem and learning how founders should sell to large enterprises. This was invaluable in getting relevant experience in a totally unrelated industry and cemented my desire to work with founders long-term as an investor.

I learnt early on that VC is a people business. So building your network is key. I started by speaking to investors. This can be difficult if you don’t have a blackbook of VC friends but try the following: a) going to pitching events and hanging around for the networking part, b) asking everyone in your network if they know anyone in VC and whether they could make an introduction, and c) reaching out to investors directly on LinkedIn/Twitter. The latter can be the most efficient but only if you personalise each message and remember it’s give/take: if you’re asking for their time, try giving them an insight or a recommended company that fits their investment thesis. Launching my own podcast — When Unicorns Fly—was another way of messaging industry heavy honchos and asking for their time.

Corporate livin c.2019

Once I knew VC was my next step, I triaged four channels for getting my ideal fund: 1) Created a short list of funds whom I would follow and track regularly on social media/website. 2) Registered my interest with recruiters such as PER People and KEA Consultants. 3) Signed up to newsletters e.g. InnovatorsRoom TechJobs newsletter. 4) Used my network (this is where the above comes in) to tell anyone and everyone that I was interested in VC so any tips/intros/support is appreciated. It’s super important not to rely on one channel; there are very few junior VC roles out there anyway and once you segment for your ideal fund (for me: early-stage, generalist, UK based), your options are limited so being proactive is super important.

The interview process with Playfair was smooth and fun but tough. It involved meeting the entire team 1:1 and creating an investment memo for our portfolio company Omnipresent. Luckily, there are a huge amount of resources out there to help you prepare for VC interviews but here’s what I found particularly useful:

  • Keep up with the news. Sifted and TechCrunch are great for industry-specific news, follow your favourite investors/funds on Twitter and catch the latest industry reports e.g. Atomico’s State of European Tech and the TechNation’s annual report.
  • Podcasts and books. My must-listens are The 20 Minute VC, This Week in Startups and Associated. I always recommend Venture Deals for the basic stuff and The Innovation Blindspot to get thinking out of the box.
  • Create your own hypotheses about specific sectors or market trends! You can use VC thought pieces to help shape your views e.g. a16z has a great content section.

Most importantly, do not rely on your achievements, previous career or network to bag you a job. Being super passionate about working with founders and showing your dedication will really help you stand out!

Khushi (Off-Cycle Analyst)

Photo by robin inizan on Unsplash

In August of 2019, a few months before my 18th birthday, I packed my bags, said goodbye to my family, and travelled from my hometown in Australia to the US to pursue an undergrad degree at UPenn’s Wharton Business School. I put up a poster of Wall St in my freshman dorm, and I remember that all I wanted to do was work there one day — whatever it took. Beyond competing in the same realm as my peers at Wharton and a desire to work in the place I’d seen in all the movies, I didn’t really know why that’s what I wanted.

Halfway through freshman year, I had the opportunity to explore a world outside the typical finance route, through a Tech Trek program Penn ran in Fall Break, which brought us to San Francisco with the opportunity to meet some of Silicon Valley’s coolest VCs and entrepreneurs. That was the first time I’d even heard the words “Venture Capital,” and the first time I’d met VCs. It genuinely made the lightbulbs go off in my head — I even wrote an entire article about it. It was the first time I’d truly seen the potential of working in, for, and with startups as a viable career path.

When COVID hit and I was back home in Australia stuck with choosing between online school and a gap year, I saw Playfair Capital’s job posting for their Off-Cycle VC position on my LinkedIn feed.

I grew up in Australia and study in the US, so the UK was a geography I hadn’t yet been exposed to, which means seeing that posting on my feed was based on the pure chance of having connected with some people based in that region. I remember reading the description and positively buzzing with excitement. In London, during my gap year? Heck yes. Demo days and meeting new people? Yes please. Working with cool tech startups and breaking into VC? Yes and yes, sign me up.

There was a part of me though, that didn’t think I was the right fit. At this point I was 18, only one year into my undergrad degree, and had no real professional experience to show. Sure, the application said experience wasn’t necessary, but the imposter syndrome I was feeling said otherwise.

Instead of stopping there and not applying, though, I took a leap of faith and reached out to someone I thought would be able to help me understand if I was a good fit for the role: the current Off-Cycle Analyst, Alexandra, who’d just written a “Why I Joined Playfair” post I’d gobbled up.

After a few back and forth questions over LinkedIn DMs, I became more comfortable in my eligibility for the role. So, I applied. The recruitment process itself was challenging but really fun. I reached out to a few of my upperclassmen friends at Penn to help me prepare for the interview process and final task I was given (an evaluation of our now portfolio company Recycleye)… And, well, that’s how I ended up with my very first offer at a VC firm. I joined remotely and 6 months later than planned, thanks to the pandemic, but it’s been a great and informative journey from the beginning. For any other young people wanting to start in VC, all I can say by way of advice is to stop doubting yourselves, understand where your passion for the industry comes from, and to ask for help from those available to you.

If you have made it this far, great job! We hope that this post illustrates there isn’t a typical background for VC, a set timeline to start your investing career, or one route in. If you’re looking to break into VC, keep an eye on our social media as we’ll be hiring for our next Off-Cycle Analyst next month.

Finally, we wanted to give a shout out to two fantastic organisations looking to increase access to VC — Included VC and Future VC — go check them out.

You can follow the Playfair team on LinkedIn, Twitter, Forbes, Vimeo and here on Medium.

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Chris Smith
Playfair Blog

Managing Partner @PlayfairCapital | Class 25 @KauffmanFellows | Contributor @Forbes