VC firms across Europe are stuffed full of mid-level investors wondering whether they’ll ever ‘make’ it to partner. There will never be as many spots at the top as there are underneath — and so many investors who are denied partnerdom choose to either leave the industry, or start their own firm.
But that wasn’t the route taken by Dinika Mahtani, who heads up early-stage investor Cherry Ventures’ London office. She joined the firm as a principal in 2021, having previously been a general manager at Uber — and just two-and-a-half years later was promoted to partner.
It was the result of years of work, and a very carefully and clearly formulated plan.
On the latest episode of the Sifted Podcast, she shares her advice for any other startup operators wishing to jump over to VC, and investors wanting to shape their own ‘path to partner’.
1/ Get to know other investors
“I spoke to one of my colleagues who was in my team at Uber, Annie Case, who now works at Kleiner Perkins, and had made the transition from Uber to venture in the US. She introduced me to basically everyone she knew. I started meeting investors at firms that I came away with being like, ‘I would not fit in there, or I would not want to work there’. I started doing these meetings casually for a year and a half, and during that period I was also building my angel investment portfolio.”
2/ Start angel investing
“My angel portfolio was about 15 to 20 companies — so not huge, but not tiny either.
“I would go to pitch events, [to get in touch with] founders very early in my angel journey, and I was very thoughtful about where I could add value, how I was selling myself. I built a small programme — sort of how to pitch yourself as the most value-add investor when you have a very small angel portfolio — and then [afterwards] building that up was much easier. There were also a lot of my ex-colleagues who spun out of Uber to build new companies — so that was an easy jump onto the angel investing path.
“Then it came to a time when my husband was like, ‘You need to make a decision, whether you want to just keep spending your weekends trying to help founders raise money and build their pitch decks for them, or you want to professionalise this and do this yourself’. And it took a while, but I only made the transition when I found a fund that was the right fit for me.”
3/ Set expectations for your first few months
“In joining Cherry I made sure that there was no pressure on me to do a new investment or my first deal within a set time, because I knew that deploying firm capital was going to be a big deal.
“So I shadowed one of our founding partners for six months. I would sit in on his calls. I would tell him how I felt about an investment. I would be shadowing him the entire time, but we had pre-agreed that this would be okay.
I made sure that there was no pressure on me to do a new investment or my first deal within a set time
“In month four, I took my first deal to IC [investment committee] because I felt like I was ready, but that was really important for me, just to understand how the firm worked, what was a ‘Cherry’ deal […] and how to navigate that transition from operator to investor.
“The things that I was naturally good at as an operator were connecting with entrepreneurs, building relationships, understanding what they need — like the winning part — so convincing folks to want to work with me, that was the easier part of it. It was more the, ‘Hey, is this going to be an interesting deal for Cherry?’ [that was hard]. Every firm is different, and so I wanted to get that right, and it’s very important for folks to learn that as early as possible in their journey as an investor.”
4/ Map out your path to partner
“The path from principal to partner doesn’t exist for a lot of people, because there’s either no space in a partnership, or because it’s the way partners want to build a firm that’s either very partner specific, or founding partners only.
“When I was hired as a principal at Cherry, I only did so because there was a path to partnership. And I made that clear before I signed my contract. I made it very clear to the entire partnership from the off that, ‘Look, this is something I want to embark on. I need all of your support. If you think that I could be qualified to go on this journey with you, then let’s do it together.’ So there was an openness from the very start.
“Ultimately to LPs, the message that has to be delivered is, ‘This person has successfully done X, Y and Z.’ I wanted to understand what those things were — and there were five things.
“One was deal sourcing. The second was writing an investment memo and taking a deal from sourcing all the way to investment committee. The third was winning. Winning is hard, winning deals. The fourth was firm building, and the last was thought leadership — being thoughtful about the things that I knew and how I conveyed that.
“What I did with those five things was give myself three-month periods where I would check in with myself and the partnership and ask how I was doing and when things were off track. We come back and discuss how to fix it, or if it was fixable, or if I was moving in that right direction.
“But most importantly, I joined Cherry because I wanted to build out the UK investment practice; to help us see the best founders coming out of the UK and be able to lead those deals by ourselves, not with the help of other VCs bringing us in. I wanted us to be high conviction and make sure that the best entrepreneurs in the UK knew Cherry, and I wanted to put us on the map. And I think we’ve moved in that direction, very much so. I’m very proud of the 10 teams that are part of our UK portfolio now, that are brilliant, and some of them we won against multi-stage firms. I’m very proud of what we’ve accomplished, and the fact that I’ve managed to put Cherry on the map out here, and I think that was what led to my success being a partner.”
5/ Own a ‘book’
“I started my career on a trading desk. There were 30 men, and there was one woman, and she was brash and very hard to work with. But one day during sort of my analyst programme, she asked me out to lunch, and she told me: ‘The thing you have to do to future your career is always own a book.’ I was like, ‘What do you mean?’ She was like, ‘Always own a book as a woman.’ What she meant was, try to always have a P&L so that you can prove that you’re worthy by performance standards, that you have something to show. For her, it meant being a salesperson on a trading desk and always being better than her peers.
The thing you have to do to future your career is always own a book.
“At Uber that advice was continued by someone who I consider a mentor, Pierre-Dimitri [Gore-Coty]. He told me: ‘Before you leave Uber, you need to be a general manager, because you need to understand what it is and what it will feel like to run part of the business.’ It was so empowering and the best advice.
“And now I do that at Cherry. I’m deploying money. I have a portfolio. You can judge me very openly, based on how successful my portfolio is, and that’s motivating to me, but it’s also something I know will keep everyone honest when they assess me looking back at my career.”
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