Interviews, News

Introducing Guy Bentley

Posted: 12 February 2023

Everyone in the Crane Herd is excited to announce our newest co-conspirator, Guy Bentley. Guy is returning to an investing role after spending the last 3+ years in operating roles at startups.

Guy started his career as a deep tech investor at Future Planet Capital but an interest in fintech led him to Flatfair where he was an early employee. At Flatfair, he worked directly on go-to-market before becoming the Operations Lead where he scaled the Operations function. He then joined Onfido as a Business Operations Manager working on special projects before getting his MBA at INSEAD.

We spoke with Guy on what motivated him to return to investing. Please enjoy.

Scott: You started your career as an investor working with founders building products that originated in research institutions and Universities. What prompted you to go and spend time in operating roles at two separate startups?

Guy: I realised that to support founders effectively and truly appreciate the issues that were keeping them up at night, I had to live through the day-to-day rollercoaster myself. On some days I definitely missed being in an investment team, but I think my operating experience has helped me to be more understanding, as I know what it feels like to be on the other side of the table.

Scott: So what was your most memorable challenge from life in the trenches?

Guy: As someone with limited knowledge of technical data science jargon when I started, I remember having an impasse with our chief data scientist late into the night on Christmas Eve. We were going back and forth over defining logic for the sales architecture in our data warehouse; what was and wasn’t “theoretically possible”. I had the tough job of translating our commercial ideas, negotiating, and finally executing with the data team. This meant working through all possibilities with a fine tooth comb and having a crash course into the modern data stack. That was a pretty memorable Christmas looking back. 

Scott: And what led your interest to go and get an MBA at INSEAD?

Guy: I think as an operator in a startup you often have to act on reflex. There are occasions when everything is on fire and there is no time to stand back, gain perspective and question whether you are driving deliberate action. I felt that the MBA was a good option to develop some of that theoretical, top level thinking, whilst building a network of incredible people. Having already studied and lived in Bordeaux for a year during my undergrad, INSEAD was a natural choice for me to return to France. It is an extremely international school with 95 different nationalities represented in our class, and has the largest number of alumni unicorn founders in Europe.

Scott: As lucrative as the offers must have been to go work in banking or consulting, why did you decide to move back into VC? 😉

Guy: My PowerPoint skills were never good enough to be a consultant! I prefer to be at the coal-face, rolling up my sleeves and helping, where I can, to build lasting companies. I love meeting and building relationships with people, so getting to work with passionate founders on a daily basis is hugely positive for me.

Scott: Why did you choose Crane?

Guy: Crane has a great reputation in the market and is one of the few funds that take a truly active role in supporting founders to build enterprise software businesses from pre-seed all the way to $100m+ in ARR. I was impressed by the line up of venture partners in customer success, go-to-market strategy and product marketing, who run workshops with founders immediately post investment. This really stood out for me when compared to other funds’ approaches to supporting their portfolio.