AMA: I'm a VC Investor

Hi I’m Ashley, I am an investor at a UK focussed venture capital fund, with a background in FX & Fixed Income trading and Corporate Finance in the finance function of an Oil & Gas Supermajor. As a VC investor I work across the full fund and investment lifecycle from sourcing to execution and get involved in all things portfolio management, fundraising, and fund operations.

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How do VC jobs differ to private equity? They seem similar in principal activity but the cultures look very different.

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Hi Ashley.

Curious - if you’re outside of the industry, who would you bring into an operations VC role? What sort of background/profile would be ideal?

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I agree, I would also like to understand the difference

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Hi Greg, You’re absolutely right in principal both involve investment in private companies but they differ typically based on maturity of the businesses in which they invest this means that they have some nuances despite ultimately seeking the same end goal.

Private Equity often focusses on ‘later-stage’ more profitable businesses where there is more visibility on the numbers as such ‘traditional’ valuation methodologies can be used and the analysis can be a lot more ‘numbers driven’.

VC is a lot more people focused as you are investing at the earlier stages where there is a lot less clarity on the business, you are really taking a position on the people involved to be able to deliver, the strength of the idea and the market in which the business operates.

Culturally I would say this is reflected too, especially depending on the stage of investment and the fund you are at, at the earlier stages you’re given more freedom a lot of your day involves meeting founders and immersing yourself in the start-up eco-system, forging connections. In my experience it feels a little bit less office intense work (more meeting/event hopping for organic sourcing) unless you are actually in the middle of a deal!

Hope this helps!

Ash

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Hi Relaxer,

Good question, I assume you are referring to operating partners and not fund ops. In my view there are several profiles that would get a look in (this does depend on stage though) :

Sector Based - People with a depth of expertise and immersion in a sector that is of interest to the fund often make great operating partners, they have their finger on the pulse and are often at the forefront of emerging trends. If you have spent your whole life in the media industry for example you will have a depth of knowledge or a more refined view on the market that many ‘traditional’ investors may not have and this is often valuable to funds.

Proven Operators - Often ex-founders or leadership roles in ‘successful’ start-ups, people who have been there and done it before have an advantage. They are likely to have come across similar challenges to a VC’s portcos along their journey and can be great value add to emerging companies, helping them navigate and allowing VCs to leverage their expertise. COO’s do really well or CRO’s. VC’s like them because they also make them more relatable to their own founders.

Role Based (stage influences this) - Functional specialists who can plug specific capability gaps across portcos (this is a lot more common as you move up the business life-cycle). This might include go-to-market, hiring/talent, product, or finance expertise. If a profile has evidence of ability and a willingness to really get involved in the nitty-gritty they will likely to well.

Often the profiles that a VC would consider overlaps with those required to undertake board positions. If a profile can be deemed a valuable addition to the board of a company it will be also be viewed as a valuable addition to a VC fund as an Operating Partner except you are expected to get more involved (so show a keenness to get your hands dirty)!

Hope that helps

Ash

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Yes this is it/

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I am a 48 year old developer and would like to work in a trading development as I feel it would be a great opportunity to learn. Would getting my CISI Level 3 help towards that?

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I’m interested in a potential career in a startup. As a VC, what are the biggest red flags you notice when looking at the founding teams? Are there any things that are easy to spot which give you an idea of what the working culture at a startup will be like?

It seems like most startups are very demanding and intense and I’m wondering, have you’ve seen many good companies that have a more benevolent approach to work?

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Curious to hear how a trading background helps you get a VC career. I’d always assumed that IB roles were better but have you found that trading experience useful?

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Hello Ashley. I would like to get into VC but I have also been put off by the point in the cycle. Surely it’s a bad time to get in if you’re just managing investments made in previous years whose value is going to be hard to realise? How do you avoid this experience?

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Hello Ashley. Thank you for being here. I would like to work in venture capital. I am studying modern history at university and have realised that my passion lies in developing companies after running a small pizza delivery business during my second year which became a success. I have applied for graduate jobs but have got nowhere. I have also been vibe coding a lot and have a good insight into the future for apps and digital companies. How can I get into VC from here?

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Hi Graham,

Thanks for the question.

I think it is heavily dependent on your current knowledge/exposure to markets. Assuming you already have a solid foundation either through past experiences, projects or general immersion then the qualification will not automatically unlock new avenues for you or open doors that were otherwise closed to you.

Roles in S&T are usually not gated behind pre-requisite requirements like (ACA,CFA,FRM etc.) which I would say are more typical of the AM/PM and IBD routes (especially when pivoting). For the kind of roles you are targeting, I would expect your developer experience to do most of the heavy lifting.

That said, I have always been a strong advocate for learning and taking on external qualifications (provided it is financially feasible), some call it signalling but in my opinion these non-required qualifications act as a self-assurance mechanism helping people overcome any doubts in their own minds instilling a level of confidence to go for things and have a “stab at something” that they may otherwise be reluctant to. If you have no prior background/knowledge then I would definitely recommend an external qualification like CISI since it would give you a solid introduction to financial markets and help you become more familiar with the language, products, and structure of the industry.

Whether you choose to do the CISI or not my key recommendation would be to get some “hands-on” project-based work that shows that you can apply your developer knowledge within the lens of financial markets. I think this will be substantially more beneficial to your applications, confidence and credibility improving the chances of completing a successful pivot.

Good luck!

Best Ash

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Hi Grind and Shine (love the name btw looks like you got the start-up culture ready to go),

Good question and happy to answer. Hopefully this is useful, although I suspect we may be approaching it from slightly different angles and have access to different information.

From a VC perspective the things I would look for are:

- Meeting dynamics - How do the founders interact with each other? Does one person dominate the conversation? Do they interrupt each other, or defer too much? You can usually learn a lot from body language.

- How open are they to office visits - This can be quite revealing. If a company is unusually reluctant to have people spend time in their offices/meet the wider team, or get a feel for the environment. Whilst there can be perfectly valid reasons for not wanting to do this, but I think openness and transparency here can tell you a lot about confidence in the culture they have built.

- Structure of the Cap Table - Unbalanced equity splits between founders can sometimes be a red flag, particularly if they don’t reflect contribution, commitment, or how the business was actually built. It is not always a problem, but it can suggest underlying issues around fairness, control, or decision-making. I would also look at the size of the available option pool.

- Staff turnover - If a company has unusually high churn, especially at an early stage, I would want to understand why. Sometimes there are legitimate reasons, but repeated turnover is often because of lack of clarity, cultural issues, or simply a difficult/hostile working environment.

- Ask about events they run for team bonding and work-life balance - Often you can also ascertain a lot if you ask the actual employees if they are quick to defend the company then it is likely that the fostered culture is good if there is a delayed or hesitant response that can be quite revealing too.

I have seen both ends of the spectrum but dejection and an unwillingness to expedite the investment process from my perspective is usually a clear indicator!

Hope that helps and good luck breaking in to the start-up world!

Best Ash

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LOL I genuinely really like this question! Something I have often thought about myself.

TLDR – My short answer is that trading is definitely not the conventional route into VC, and there is no/very limited technical overlap. The day-to-day work is very different. But the experience and habits I built in trading have been genuinely very useful in my VC career, particularly when it comes to judgement, decision-making, and comfort with risk.

My path has been fairly atypical and is something that me and my team joke about a lot!

I think you are right typically VC/PE careers are often associated with historical IB experiences (PE in particular). I think VC is somewhat more “accepting” of non-traditional profiles especially at the earlier stages. There is less of the unspoken rule “we only hire from X or Y and only look for ex-bankers or ex-consultants” (that mindset definitely still does exists especially at later stages, but it doesn’t / shouldn’t necessarily preclude anyone from breaking in or at least trying to!)

Leaving the “politics” of investing roles aside for a moment. The hiring process really becomes about what you bring to the table. In my case whilst there is not much overlap in the “hard-skills” or “technicals” you use in trading and those prevalent in VC. When I reflect on it there are a lot of aspects where I think my career in trading and the skills I developed there have been extremely useful.

Firstly the “technicals” in investment management are ‘teachable’ / ‘learnable’ so really this is something you can drill and get better at over time and through exposure it just needs work; which is why I really don’t like the aforementioned mindset (and often reality) of precluding candidates based on background. Where I have found my background useful in my VC career is related to the perceived ‘softer’ skills.

1. The ability to form a view and execute accordingly - Some trading strategies require you to form a view and gain conviction. You would often justify to yourself the causal links and impacting factors when taking a position, this is essentially the same logical chain of reasoning in the world of investing especially when developing investment theses and looking at markets.

2. Focus on core variables - Trading taught me how to juggle and decipher information whilst filtering out noise; how to hone in on the most crucial variables; this maps really well to the world of investment management when you are forming a view and when you look to build models / undertake scenario/sensitivity analysis knowing what factors to diligence and where the outcomes can be made or broken. The key difference is the feedback loop in VC is just so much longer and you do not have the ‘safety’ of liquidity.

3. This feeds in nicely to the next skill comfort around risk - Trading really helped me get comfortable with the idea of risk and making decisions; capitalising on opportunities when they present themselves. Something investing is all about! Although I found trading somewhat more forgiving (but much faster) than investing since the risk is still binary but less absolute; in FX there is no real chance of something going completely down to 0 and given the liquidity of the market you can always close your position if you change your mind (but you would still feel the loss because of market movements and loss on spreads).

So overall was a weird transition (even to this day) but I did and continue to find my prior experience useful!

Best Ash

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Hi Personobscura,

I completely understand your reservations. But in truth, that is just the reality of the market right now, and VC has never really been a job that is exclusively about making new investments. It is a combination of execution, portfolio management, capital allocation and trying to create value over time, especially at the early-stage and as you become more senior.

In some ways, that is part of the appeal! New deals whilst an important part, is still only a part of the overall picture a lot of it is about helping companies navigate difficult periods, supporting founders, capitalising on opportunities if a follow-on opportunity presents itself and trying to generate value even when the environment is less forgiving.

If you do want to focus on new investments however, then the best way is to target large shops where there is clear delineation between roles, or target funds that have recently finished deploying and are raising their next fund/have just finished raising. If you take the classic GP-LP structure the first few years of a fund are typically the main deployment period, so joining at that point should maximise your exposure to new investments.

Alternatively, you could look to apply to other fund structures that have more durable deployments such as VCT’s; who effectively offer a steadier stream of new investment focus.

Either way, do not let the market hold you back if you want to join VC!

Hope that helps

Best Ash

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Hi Studentfinance,

Firstly, kudos on the entrepreneurial background. Running a small business successfully, shows clear commercial instinct and something a lot of VC’s value. The fact that you have built something yourself will already give you a different perspective from a lot of candidates and can be a real edge. Make sure you capitalise on that and capture what you learnt from your experience and how it can translate to your role as an eventual investor.

What were your key struggles? how did you overcome it? was it avoidable in hindsight? and what would you do differently? One of the best things you can do is evaluate your own business with an investor hat on, I think it will give you really valuable ammo for some conversations down the line.

If you do not yet have direct experience in VC, one of the first things I would suggest is looking at entry points like Newton Venture Programme. They are a very good way to build knowledge, meet people in the ecosystem, and make your interest for the investment side more apparent on your CV (plus they have a free programme). I believe their MD actually did an AMA on here recently as well, which may be useful (Link).

Beyond that, networking is still one of the most effective ways to break in, but it works best when it is done thoughtfully. Try to set up targeted conversations have a clear view on the sectors you are interested in, know which funds invest in those areas then try to set up meetings.

Alternatively a good networking space is events, if you strike up initial conversations with VCs and try to get one-on-one follow ups that will work well. VCs especially early stages are a lot more visible than most at these events. If you do manage to set these up make sure you come prepared to those conversations. Try to write short summaries (super brief IC memo’s) about companies you would invest in and why so you can share these ideas with VC’s (do the job before already having it – “I saw this company recently and think this…..what would be your take on it from a VC perspective…..” they will likely have to come back to you on their thoughts though :p).

If you are attending an event and a company has presented, something that I found works really well is speaking to the VC investors at the event and exchanging thoughts on the companies that presented, if you think they are worth investing in and why (this works really well and leaves an impression since these events are often neutral territory and people are more open to a conversation!).

Good luck and keep going!

Best Ash

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Thank you alls/

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Hi. I bought pizzas from Aldi and sold them for a 300% markup after adding a few toppings (also from Aldi) to friends in my Whatsapp group who wanted food late at night. I did quite well out of it last year

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Thank for this. Can you say whether this short youtube video is an accurate portrayal of VC life please https://www.youtube.com/watch?v=hx5P1O10VFM

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