Life as a VC Associate: Lessons from 2.5 Years

I got my shot in venture capital 2.5 years ago when Fede, Chris and Joe brought me on board as Playfair’s first ever Associate. Having recently been promoted to Principal, I wanted to take a brief moment to pause and reflect on the lessons I learned in the first chapter of my career as a generalist VC.

Before I started at Playfair, I loved reading whatever industry insights I could get my hands on, including a number of insightful blog posts written by investors I hold in high regard, such as Chris Corbishley or Check Warner. In keeping with that, here are my reflections of what I wish I’d known when starting out in VC.

The foundations of my career in VC were formed in three distinct stages: explore, develop, focus. Each stage has provided me with important lessons that I will now attempt to bring to life with real-world examples from the past 2.5 years.

Stage 1: Explore

Do you know what you know and what you don’t know? This first stage is all about finding and testing the edges. From there you can hone back towards the centre with confidence.

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i. Meet founders

Founders are the beating heart of venture, without them this industry would not exist. There is no substitute for getting out there on day 1 and meeting founders.

Be humble, be open-minded, bring your fresh perspective as an advantage. Don’t pretend you know everything (you don’t), don’t try and be an arch-interrogator, and especially don’t waste founders’ time.

My first ever demo day was Entrepreneur First in March 2019, a few weeks after I joined Playfair. As a team, we watched 30 pitches on stage and collectively triaged the top 10 for a meeting. Regardless, I was excited to go around the stalls afterwards and meet every founder face to face. I’m so glad I did otherwise I wouldn’t have met Rayna and Georgina from Vinehealth. After introducing them to the rest of the Playfair team, we went on to lead their pre-seed round and we’ve loved every minute working with them since.

ii. Meet investors

I see other VCs as my colleagues and friends. There is no other industry quite like it. Embrace it, give before you take, ‘network’ in your own style. Don’t try to ‘play the game’, don’t follow the crowd, don’t be everywhere yet nowhere.

Diversity of thought and perspective is incredibly powerful. Much has been written about the homogeneity of the VC community (luckily, it is slowly improving), but under the surface, you will find a brilliant array of backgrounds and personalities. Seek out this breadth, it will broaden your mind but also make life much more exciting.

Equally, there is no networking ‘game’ to be played. Those who try have already lost. This is a small, transparent world of smart people who can smell an opportunist a mile away. Build relationships with people you like and where there is a natural two-way relationship.

This is what I mean by ‘network in your own style’. This stage is about first testing and discovering what your own style is because there is no ‘right’ way to building a network, there’s only your way.

I’d like to shout out to a few people who I met in the early days, some before I’d even got a job in VC, all of whom have helped me think differently and who I always enjoy bouncing ideas off. Some are building careers in VC, some are building companies as founders, some are doing something entirely different.

Thank you Alexia, Kam, Pippy, Freddie, Archie, Hector, Belinda, Elena and so many more since 🙌

iii. Be a deliberate generalist

It’s fashionable these days to be highly specialised; an ‘expert’ in XYZ. That’s fine later, but I’d argue it’s crucial to start as broad as possible. There’s a huge amount of unexpected transferable learning across different industries and even across traditional B2B/B2C lines. It’s also unlikely you’ll branch back out once you’ve found and doubled down on your speciality so enjoy the freedom while you have it.

Personally, I enjoy the challenge of switching contexts. From consumer FinTech in one pitch to computer vision for waste management in a second and a productivity tool in a third. From this approach, I’ve built a breadth across sectors I never thought possible, a depth in industries I never would have thought interested me, and I’ve had a lot of fun keeping it fresh along the way.

David Epstein wrote a great book challenging today’s prevalent thinking: ‘Range: How Generalists Triumph in a Specialized World’. Whether you agree or disagree with the title, it’s a well-researched and argued read that will get you thinking.

iv. Embrace imposter syndrome

You will never stop feeling like an imposter in this industry so stop trying to. I would even say that feeling that slight sense of being out of your depth is a good sign that you’re learning and pushing yourself.

With the key Stage 1 goal being to get yourself out there, literally and figuratively, you can judge your success by keeping this feeling front and centre. Don’t try to fight imposter syndrome, own it.

In April 2019, after recently joining Playfair, Chris suggested I take his place at a Founders Network event in Shoreditch. I was asking myself what on earth I had to say or share as a twenty-five year-old with next to no experience yet in VC. A former Goldman Sachs partner-turned-angel didn’t help my feeling of imposter syndrome when he verbalised this question to me before the event started.

Honestly, that question is what lit a fire under me to prove I was there for a reason. It was a Q&A session from founders on what VCs look for in a pitch deck so I realised I actually had four years of personal experience doing this as an investor through crowdfunding. That was the confidence I needed to share some sensible, safe advice that I’d learned and assimilated from other experts over the years. It also motivated me to make sure next time I was on stage there’d be no one asking why.

Stage 2: Develop

Alongside exploring and testing the edges, there are some fundamental hard and soft skills you need to develop to ultimately be able to own the end-to-end investment process. From sourcing and diligence to negotiations and legals through to portfolio support and future funding.

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i. Learn how to bring the best out in people

You’ll have noticed that most of Stage 1 is external-facing. In Stage 2, it’s important to pay more attention inwards. Each associate’s fund is their centre of gravity vis-a-vis the rest of the VC world. How can you try to elevate your fund to the top table of venture capital? Answer: ‘The whole is greater than the sum of its parts’. If you can learn to bring the best out in your team, you’ll be amazed how much more a few individuals can achieve than you think.

In a well-balanced team, everyone will have their own style of working. Structured/unstructured, 80:20/perfectionist, talkative/listening, extroverted/introverted, etc. Remember your style isn’t the ‘right’ way, it’s just your way. Figuring out how you can fit together with the individual tetris blocks of your team is the key to supercharging yourself, the team and ultimately your fund.

I’m incredibly proud of the work we’ve done as a team for Female Founder Office Hours. Five bi-annual events since founding it in 2019 have managed to bring together over 700 founders for 2,800 one-to-one mentoring and pitch meetings with 90 investors.

I honestly believe the only way we’ve managed to do this amongst just a few of us with full-time investor roles is by playing to the strengths of our team. Some of us have the investor connections, some the press and industry connections, some the organisational skills, some simply the creativity to keep the initiative fresh.

As a team, we all feel strongly about the state of diversity and inclusion in our industry today so we have a vision to play our part to improve it. That energy has fuelled a true team effort that we would never have thought we’d have time to combine with our day jobs.

ii. ‘Never split the difference’

Chris Voss’s ‘Never Split the Difference’ is a must-read for any associate learning the art of negotiating. Written by the FBI’s former lead international hostage negotiator turned writer and lecturer, this is 50% business book and 50% first-person account of real-life hostage events that mean you can’t put it down.

Fundamentally, VC is a people business and so even at the most transactional moment of negotiating a term sheet, you need to understand and develop the soft people skills that will win you much more than a good price. You need to find the delicate balance between a good deal for your LPs and a fair deal for the founders you’re partnering with for the next decade.

If you’re time-poor and don’t think you’ll ever find time to read this book or any of the others I’ve mentioned in this post, I’d be very happy to share the notes I’ve taken while reading – just drop me a message on LinkedIn.

iii. Become a part-time lawyer

Start by reading Venture Deals, by Brad Feld and Jason Mendelson. Then get into the nitty-gritty of every term sheet and long-form document (investment agreement, articles, etc) that crosses your desk. Understanding which terms VCs and founders find most important, what ‘market’ is, and how far you can push or be pushed on any one term is critical armoury as you learn to negotiate and close deals.

Some people might find legal terms and the seemingly endless back-and-forth negotiations through multiple sets of lawyers an entertaining challenge; most do not. The best way to navigate this crucial phase of negotiations is to know what you’re talking about so you can lead the discussion rather than constantly playing catchup.

For this example, I officially hand over to our Managing Partner, Chris, who is our resident legal expert having spent 8 years as a corporate lawyer and qualifies as a geniune part-time lawyer.

iv. Hone your pitch style

There are infinite different pitch styles across many different types of pitches. In my experience, the key types are:

1. The first pitch;
2. The follow-up ‘dig deeper’ pitch;
3. The ‘deep dive’ pitch;
4. The ‘sell mode’ pitch.

The key objectives from each are to uncover the strengths and weaknesses of a founder and their business while simultaneously reverse pitching them your own strengths as an investor/fund. Depending on how ‘hot’ or attractive the round is, you should flex the amount of emphasis you put on pitching yourself vs the founder pitching you.

Style-wise, pitch styles fall along a spectrum, including:

1. The unstructured chat
2. The data gathering chat
3. The passive deck-based chat
4. The active deck-based chat
5. The befriend-the-founder chat
6. The Hercule Poirot chat
7. The juggler chat (a skilful combination of the above)

There are investors who go into pitches totally unprepared. Some people have the gift or experience to wing it. Most come across very transparently to founders who, if you stop to consider it, are on the other side of dozens of identical meetings so can see a bullshitter from a mile off.

Preparation can come in hard and soft forms: deck reviews or considered thoughts. Just remember, there is a difference between an unstructured chat and an unprepared chat.

As long as you respect founders and their time, there’s no right or wrong way if it allows you to get to know them and they you.

Below is the template note structure I use for almost every pitch I take. I would highly recommend trying this: start with a blank note, build it up and cut it down iteratively until you have something similar that works for you and your pitch style. Of course, you don’t need to use one at all if you prefer.

Likes/dislikes/follow-up are used at the end of the call to summarise my key thoughts from the meeting for both my own reflections and to discuss with my team.

Core questions have been adapted from a couple of VCs and in a brilliant book by Ali Tamaseb, Super Founders. They have served me extremely well in getting to the heart of a startup’s problem statement and the way the founder is thinking about product-market fit. They also afford a useful amount of long-distance perspective, particularly useful when you find yourself on 20–30 pitch calls in a single week.

Questions pre-call are where I write up any questions I have from reading the deck ahead of time or discussing key areas to probe with my team.

The remainder is my synthesis of the core parts to any business. These aren’t designed to be ‘filled in’, usually I don’t write anything under a couple of these sections. They’re a way of structuring my thoughts for reflection on the call, immediately afterwards and if referring back at a later date.

Stage 3: Focus

By now, you’ll have built up a solid foundation of core skills across the beginning and middle phases of the deal lifecycle up to the point a new deal closes. The goal now should be to focus on honing these two phases and growing into the third and hardest phase: company building.

You’ll also almost certainly have realised you never have time for anything. Your ultimate goal has become prioritising what matters most — to you and your goals — and focussing relentlessly on that.

You should try imagining what type of partner you would like to be in the future and design a path towards that goal. This will naturally highlight your strengths and allow you to focus on those.

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i. Learn how and when to say no

Ironically, this is a job where you spend your life saying yes to everything to gain access to founders and then spend your life having to say no to 99% of those founders. These well-known statistics might suggest you should focus on adding to the top of the funnel to get a higher chance of 1 company filtering through. This is a false economy. The reality is you’re better off improving the conversion % by being more ruthlessly focussed on the companies you’re meeting in the first place.

It’s much easier to say yes than no in VC. In Stage 1, you’ll have embraced the Yes Man mentality; now you need to use that experience to have more conviction about how likely a pitch is to ultimately have the qualities of a $[100m] revenue/$[bn] valuation outcome (insert your own fund’s criteria; unicorns aren’t the only VC animals in town). This is an opportunity cost problem: for every middling or out of scope pitch you take because you’re on the fence, you fill a space for a potential standout one.

Being brave and switching my mentality from ‘yes’ to ‘maybe’ has been one of my hardest personal challenges over the last 2.5 years. The lightbulb moment for me was realising that saying no allows you to say yes. It’s an investment in the calculated probability of a future ‘yes’ vs the door-closing ‘yes’ of the present.

Personally, this struggle is what pushed me closest to FOMO-driven burnout. It’s doubly a silent killer because you don’t know what opportunities it prevented you from seeing. Remember that just because you don’t see something, doesn’t mean it doesn’t exist.

ii. Learn to look after yourself

This is inextricably linked with learning to say no. Above are a load of business reasons; here are a few personal ones too.

I was close to burnout as a banker (which I hated) and I’ve been close to burnout as a VC (which I love). In this career, it’s your responsibility to balance your own work/life balance. VC is an infinite job, but you cannot work infinitely. Try to resist the temptation to sprint to the FOMO lurking around every corner; this is a marathon.

Working with Chris at Playfair, I set myself three achieveable self-management goals. In addition to the thoughts above, these are some practical steps I’ve taken which have already improved my own mental health, but which you should entirely adapt to what works for you.

1. Pace. Maximum 3 days of 11+ hours screen time per week.

2. Breaks. Minimum 3 walks a week with no phone.

3. Projects. Maximum 3 projects at one time.

iii. Fundraise with your founders

Once you’ve invested in a founder’s startup you become quite literally fully invested in them and their business. You live their highs and their lows, and nowhere more than fundraising.

By this point, you’ll have an armoury of skills to support your founders in almost every part of their pitch and DD process. You’ll have the network to make investor introductions, you’ll have the experience to perfect their deck and practice their pitch, you’ll have the negotiating expertise to help them with term sheet and legal negotiations. You should have the personal relationship to be there for them to smooth the rejection of inevitable passes. You should also be there to celebrate and encourage the wins — big and small — throughout the process.

Done right, when your founders raise that next round, you’ll feel like you raised it with them as a cofounder.

Over a few weeks around Easter 2021, Victor, Peter and I got together to plan Recycleye’s seed fundraise. It was a particularly busy time at Playfair, while founders always have a full-time business to run simultaneously, so we spent a lot of evenings and weekends jumping on and off the phone between PowerPoint editing, commenting and ideating. It felt equally like being in the trenches together and atop a mountain telling the world about our vision and why we should be heard.

I’d hope those joint efforts played a small part in ultimately finding our ideal lead investor and oversubscribing the round. The celebratory home-cooked barbecue and tiramisu will certainly live long in the memory.

iv. Find your trusted allies

By now, you’ve embraced ‘networking in your own style’ and this has naturally built a network of people around you that you can reach out to for different things and you know to varying degrees. The next phase is figuring out which people in this group are your trusted allies.

Who are the top ten people you would immediately go to when asking for a favour and who you would do the same for in return? Who can you cut through the bullshit and be vulnerable with? Who do you see as a long term friend whose opinion you will trust and value regardless of whether they remain in a directly relevant role in venture?

These trusted allies are a small private family of mentors and advocates on the journey with you, whether they stay in VC or not.

v. Who do you want to be in 5 years?

Whether you’ve just started as an intern or analyst or are a few years into being an associate, a useful exercise is to ask yourself what type of partner you’d like to be. Now you’ve found and tested the edges, you can sketch the outline of your ideal future self and map out what you need to do to get there from where you are today.

Here are a few key questions you could start to ask yourself:

1. Having explored being a deliberate generalist, do you enjoy this breadth or do you prefer going deep into a couple of specific sectors?
2. What will make founders choose you?
3. As a board member, do you want to be an operator, fundraiser or strategist?
4. Can you leverage the best from a team or do you perform better as a lone wolf?
5. Are you a thought leader or do you prefer to assimilate research and ideas from others to form your views?
6. What is your public persona? Are you a Twitter fiend, ‘in’ with the press, a LinkedIn guru, or simply someone who tries to get on with the job in the background and hopes results speak for themselves?

These are just a few important questions that have made me think. For some of them, you’ll have an instinctive answer, for others you'll have no idea, and for many, you’ll likely tend towards a safe middle-ground. Whichever path you end up on, just make sure it’s deliberate. This is an industry built on conviction after all.

*Being wrong is the best way of being right*

Photo by Andrea De Santis on Unsplash

My final word is by far the biggest lesson I’ve learned so far in VC: being wrong is the best way of being right. To take this lesson on board, you need to buy into its open-to-fallibility mentality. It’s hard, it takes a lot of courage and I still continue to fail to stick to it because it’s easier not to.

I believe that being open-minded to the idea that you can be wrong at any point about anything is the only way to keep yourself fresh and ahead, and to ensure you’re always learning the new definition of ‘right’.

So, in the famous spirit of VCs holding seemingly contradictory points of view simultaneously: use your associate years to explore, develop and focus on building your unique conviction; then allow it to be challenged, always.

I want to say a huge thank you to the entire Playfair team who have become a true family to me over the past 2.5 years. I wouldn’t have had this opportunity anywhere else, wouldn’t have learned these valuable lessons, and I definitely wouldn’t have had as much fun along the way. 🙏 Fede, Chris, Joe, Jeevan, Simon, Elise, Andrew, Alie, Jeremy. Here’s to more of the same 🙌

ps. If you made it to the end, thank you for reading, I hope it was useful. I always love meeting new people who are passionate about venture and tech so please do reach out :)