Lifting the lid Part 2: How the Playfair team got into Venture Capital

Chris Smith
Playfair Blog
Published in
13 min readJan 25, 2023

TL;DR We know that our industry can be somewhat opaque. We were overwhelmed by the interest in our first Lifting the lid post back in April 2021 so in Part 2 three more members of the team reveal the story behind how they landed 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

Sheff (Associate)

Until I reached 18, I wanted to be a professional football referee. In fact, I was totally unaware of technology, startups and the world of Venture Capital. I spent my weekends on pitches across Blackpool and West Lancashire whistle in hand, developing a thickness of skin which still comes in handy today.

Studying Economics at University brought about a natural shift in my life ambitions. I desired to wear a suit over a kit and, like most of the people on my course, completed internships within large banks. Whilst these gave me excellent exposure to the professional world, I knew that the large corporate banking life was not right for me. The suit and tie just never seemed to fit right.

Whilst I was trying to figure out the right career path, I found myself increasingly spending time in Leeds casinos exploring my interest in poker. It was intellectually stimulating, people-focussed and financially rewarding. I was obsessed. I made the decision not to search for ‘proper’ graduate jobs and to give professional poker a try. Some of the transferable learning from this time can be found in this post: From Seedy Casinos to Seed Investing at Playfair.

As COVID forced the world online, (and closed the casino — my workplace), it was clear the time was right to get a ‘more normal’ job. I joined Neudata: a startup selling fintech to technology startups. I was exposed to the highs, lows and controlled chaos of a high-growth startup in a revenue generating role. I liked making a material difference to the company and the variety brought about by the more flexible structure a startup creates.

It was only 6 months before I joined Playfair that I learned the meaning of Venture Capital and that I was desperate to join this industry.

‘Breaking in’

I thought I would struggle to ‘break in’ to VC. I am aware of how competitive the roles are and job descriptions didn’t instil me with confidence regarding my skillset.

Typical VC job description

I later learned that VC roles are varied, and the most forward-thinking funds realise that a variety of experiences create the best teams.

Venture is about people. People prefer storytelling to numbers and startups prefer doing to modelling. The most successful funds are now actively seeking candidates with operational experience. Playfair were excited about how my background could add fresh perspectives to the team.

Playfair’s job description for comparison

The trick is to take your experiences and think deeply around what you got out of them. How can you derive unique insights? Do you understand certain markets, business models, or technologies better than others? Are you obsessed by a specific industry? Have you built a following? Can you uncover unique companies through a proprietary network? Do you connect people? Where do you excel?

A good fund should be assessing for these skills, rather than box-checking for recognisable names on the CV.

Find your ‘thing’, and then find the fund who is interested in your thing — attitudes are changing and a variety of experiences are valuable!

João (Analyst)

When I was 16 years old, I remember hearing in the news that Portugal had just gotten its first unicorn. For a kid who had never even heard of what a startup was, the whole idea that my country had just been announced as the birth place of a mythical creature was somewhat far-fetched, even though this unicorn’s name was Farfetch (pun-intended) and it was very much a real company.

I was so intrigued that I spent the next couple of months just diving deep into this amazing world of startups, consuming every single piece of content I could find. Needless to say, at the time there weren’t many 16 year olds spending their free time attending online demo days and pitching competitions or skipping school without anyone noticing to volunteer at Web Summit.

If I had to pin-point my crucible moment — the moment that I realised that working with startups was what I wanted to do for the rest of my life, it was that first year that I attended Web Summit. Being surrounded by all these incredible founders with fascinating ideas of how they were going to change the world allowed me to understand that this is what I wanted my future career to look like every day.

My mother is a paralegal and my father is in the army. In fact I am the first male in the family to not join the military. I am also the first person in my family to ever study or work in business. So as you can imagine, it wasn’t easy to explain to my family what a startup was let alone that I wanted to build a career around startups.

I then started my undergrad in Business Administration and immediately started looking for ways to work with exciting early-stage startups. There was just one small issue. No founder was open to the idea of hiring an 18 year old 1st year undergrad. So I looked for ways to create an opportunity where there wasn’t one. I ended up building an organisation where we would assemble teams of like-minded students who wanted to work with early-stage startups and we would join these startups to help them solve a particular challenge that they were facing (be it in Operations, Strategy, Sales, Hiring or even Fundraising) and we’d do this completely pro bono. This allowed me to get significant operational experience over the following 2 years. Many of these startups ended up not making it, but some of them actually became successful and one of them went on to achieve unicorn status.

I also realised during this experience that even though I could try to help these startups operationally, there was only so much I could do and I really wished I had the possibility to also help providing them with the capital they needed to grow. This was exactly the job description of a VC.

I then started thinking about what attributes or skills I wanted to develop in order to succeed in VC. Besides having worked with startups some of the areas that I wanted to focus on were: building up a network of VC’s and startup founders, developing some financial modelling skills and in my case given my deep interest in technology, having a technical background. With this in mind I spent the next years preparing and developing these elements. I developed financial modelling skills during my time in M&A and PE and my technical knowledge through my Master’s Degree in Machine Learning & AI (getting fully emerged into Python territory). I also continuously worked on building meaningful and long-lasting relationships with VCs and founders alike.

In the summer of 2021 a great opportunity came. I joined the initial team of an emerging Web3 VC fund. We were just starting out so we focused completely on fundraising and finding LPs that would support our vision of investing in the most promising Web3 founders and projects out there. The team ended up raising $30M from investors like Marc Andreessen, Chris Dixon, Gavin Wood and SoftBank among others.

After the summer, I stumbled across Included VC, an 8 month Fellowship where aspiring venture capitalists from diverse, overlooked communities get exclusive access, education and mentorship from some of the world’s top VC’s. I ended up joining the cohort. At Included I got to learn and work side-by-side with amazing people from more than 40 nationalities. Each of us had an incredible and unique life story but what united us was our passion for startups and desire to break into VC. Along my journey at Included I got the chance to learn from some incredible mentors like Daniel Blomquist, Kamil Mieczakowski and Matthew Goldstein whose invaluable advice allowed me to better understand how I should go about building a career in venture.

In 2021 I joined Techstars as the first EMEA-wide investment team hire and focused on finding inspiring early-stage founders to invest in and working with Techstars local teams to expand our reach within the region where we were making around 240 investments a year. This was an incredible formative experience that truly allowed me to learn and understand the ins-and-outs of early-stage startup investing.

After spending some time in the industry getting to know many VC teams across Europe and the US I realised how different each of these teams were and how that impacted their dynamic of interacting with founders and working together. It was only then that I truly understood that capital in itself is a commodity and whilst many of us tend to idolise the mega-funds and assess a fund’s quality by their AUM, in reality nothing is more important than finding an incredible team with whom you identify and see yourself working and growing with.

This factor was what eventually made me realise that Playfair was the right place for me. Unfortunately, to this day there are many aspects of the VC world that need improving.

The whole interview process at Playfair was marked by a series of “green flags” (as I like to call them). Prior to the whole process, the Team posted an incredibly detailed Medium article explaining each of the recruitment phases. Each step was clearly designed to objectively assess a different candidate dimension and focused on avoiding biases. Although it was a long process it was also one of the most organised and streamlined processes that I have ever been through. Usually we’d be informed if we moved to the next phase or not by the next day and the next step would be scheduled for the following week. By the end of the process I truly felt like I had been on a journey with the whole team which helped me understand that this was the team that I wanted to join.

Overall, you never know what tasks or business problems you will be asked to solve and each VC process is unique in some ways but there are definitely concrete steps that you can take in order to not only be prepared but also make sure that you can stand out. In essence there are 3 key areas that you can focus on developing:

Startup Knowledge:

  1. Learning about all the different challenges and phases that a startup goes through along its journey. Some of my personal favourite resources are: “How to Start a Startup”- Y Combinator & Stanford short course, “The Lean Startup” by Eric Ries
  2. Keeping up with the news on the startup world through publications like Sifted and TechCrunch

VC Knowledge:

  1. Get acquainted with all of the terms used by VC’s particularly in the realm of term-sheets. A good source for this is Venture Deals.
  2. One of the most overwhelming things in the beginning is also to quickly be able to get a sense of the VC funds landscape and be familiar with all of the key players in your region and/or area of expertise. A good start here is to check for example some of Dealroom’s reports, The 20 Minute VC, Landscape’s Lists are also good to get a feel on founder’s feedback on specific funds. In general, keeping up with the general sentiment on LinkedIn and Twitter is also a good way to get more subjective/informal data.
  3. Learn about the VC Investment Process and get familiar with tasks like putting together an Investment Memo because chances are you’ll be asked to perform a similar task during a VC recruitment process.

Sector Knowledge:

  1. If you’d like to focus on a certain area it is also important that you get familiar with the dynamics of that space and get expert inside knowledge. There is no silver bullet here given that there isn’t an all-in-one data source that is relevant for all sectors but a good place to start is checking the articles and reports that the VCs in your area of interest are posting. For example for someone who is particularly interested in B2B SaaS, Christoph Janz’s SaaS Funding Napkin and The Goldilocks Zone of SaaS Metrics articles are a must.

You should then make a list of which VC funds you’d like to work with. Start by filtering by the stage that you’re most interested in, which in my case was early-stage. If you’d like to focus on a specific sector as well, feel free to narrow down your search accordingly.

At this point 50% of the work is done and the most important phase begins… applying all your knowledge into actually applying and interviewing for VC positions.

Clare (Analyst)

My background is the epitome of “there is no typical path into VC.” I’ve always been interested in anything and everything, and it’s probably this insatiable curiosity that landed me here at Playfair.

The short story here is that I’ve always found startups and the tech world fascinating. After my freshman year at college, I got accepted into an internship program by my university’s entrepreneurship centre and was able to spend the summer working for an early stage HR tech company.

This was my first experience with startups and I absolutely loved it. From there, I’m sure you can imagine how the rest of the story goes. I spent the next five or so years finishing up my bachelors degree, “finding myself” through traveling, trying different roles in different industries, and getting my masters. Throughout it all, the one constant was that I kept up to date with news from the startup world.

I eventually found my way back by joining an early stage fintech in London and then finally ended up at Playfair.

That’s the short story.

The long story is that I’ve always tried everything that I could. Growing up, I dabbled in more sports than you probably know even existed. I lived in Madrid for 6 months because I was tired of my Spanish being “conversational.” I spent so much time befriending countless people that I have nothing in common with, just because I thought it would be cool to get to know someone different. I even travelled alone for 15 months to force myself out of my comfortable

Throughout it all, I had no idea what I was doing. I pursued whatever interested me until I stopped learning and growing from it. Then I moved onto the next thing. This mindset is the reason I jumped from the telecommunications industry to fashion to mobility to fintech in such a short time. It’s also the reason why I fell in love with startups. They’re constantly evolving and changing so there’s always something new to learn or room for growth. It might already be apparent from the outside, but as an operator, you experience an entirely different level of growth and knowledge that only comes with jumping in and getting your hands dirty.

This is where my entrance into VC comes in. I was working at a fintech startup and, even though I was continuously growing, my learning soon slowed. I was already eager to jump to another industry after just a few months and had started shopping around when my friend sent me a job listing. According to LinkedIn, over 500 people had already applied for the role, but it sounded too good to not apply to. Soon I was chatting with Jeevan and Sheff and reviewing pitch decks with Henrik. The process felt so natural and challenging (in the best kind of way). I came away from each step of the interview with so many questions about things that I had learned and felt my curiosity truly blossoming for the first time in a long while.

I never imagined that I would make it this far if I’m honest. I just remember continuously hoping to make it to the next stage because I wanted to see what new thing the team would put in front of me. Now that I’ve been in the job for a bit, I can confirm that every day is just like this. You wake up unsure of what you’ll come across but eagerly head to the office to find out. This is a passion that’s innate in all VCs; I’ve seen it in the whole Playfair team and in others that I’ve met along the way.

And that concludes the long story of how I made it into VC.

My takeaway is that breaking into this world isn’t about how much you prep for the interviews or about your background, it’s about genuine curiosity and excitement for what there is to explore out there.

If that’s something that you think you have, you’re on the right track. Just be patient and keep an eye out for any opportunities that arise. VC is so broad and open ended, any experience you gain in the meantime is applicable and makes you a stronger candidate. For naturally curious people, don’t be afraid to tap into those inklings and learn about even the most random things. One odd fun fact can be all the edge you need against the thousands of other candidates you’re up against.

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.

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