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