From a venture investor’s diary #8: on “founder-investor fit”

• By ssyc1
• September 9, 2026
• No Comments

(image credit: Hans-Peter Gauster on Unsplash [adapted])

Have you been hearing about “founder-investor fit”? I have and it made me realise this is definitely something I test for (I am thereby adding the word to my vocabulary!)

I’m always saying that an investor can be a multiplier for a founder but only if we can work well together, which often requires us to understand each other’s strengths and weaknesses.  When I think about it some more, I think about mutual respect and understanding being are 2 key ingredients in getting the best out of each other (or any partnership for that matter)! 

I write “respect” with gravity and not superficially: the respect comes from you the founder-CEO knowing this investor – whom you’ve chosen – has strengths, knowledge and experience you can tap into, and it comes from the investor also always respecting the founder’s strengths – the deep knowledge he has of his product, his people, and his industry.  

Ensuring you leave the founder-CEO to do his job is also part of this respect – I am reminded of the learnings that some operator VCs often have to do early in their operator-to-investor transition.

I write “understanding” in a similar vein: understanding the strengths and weaknesses of each other – especially when supported by a shared and aligned vision – is key to success in collaborating!

An interesting take with some deeper insights on this is how founder-investor fit isn’t just about shared vision but also about shared risk tolerance for being wrong and especially in situations where disagreements risk becoming institutional crises. 

We always think self-awareness and intellectual honesty solve (or pre-empt) quite a lot problems – and our honesty preference extends to encouraging founders to take the pain and to work with as much honesty as possible (I smiled when I read this from another VC, “don’t kick the can down the road”). 

But these specific suggestions are very helpful too and I note 2 of them here:

– Establish clear decision-making frameworks before you need them – so you have some mechanism for resolution to a disagreement rather than having to fight it out in public. 

– Have explicit conversations about investor exit – it forces both parties to be honest about their time horizons and what they’re optimizing for.

But what I love most is the advice to manage investor relationships as a strategic asset.  An equally important advice to founders that I’ll highlight here: your ability to manage investor relationships is part of what investors are evaluating.  Yes, this definitely resonates, so does this:

“We are looking for founders who are coachable but not passive, who listen to feedback but maintain conviction, who can disagree productively with smart people.”

I look back at one of the first posts I wrote about what we look for in founding teams and #5 being “getting the funding part right” and I had written about the partnership element as well as the governance element.  Some things really are fundamental!