Transcript follows & video below. This is Part I of the interview. You can view Part II and Part III here

What is your sweet spot, in what kinds of businesses do you like to invest?

We have a team of 6 partners here, so 3 of us on the life sciences side & 3 of us on the tech side. In technology we are very old fashioned in many ways. We invest at Seed or Series A. We like to take generally sort of a lead role & really partner meaningfully with the companies that we back. Then we’ll look for high upside, highly scalable, highly ambitious entrepreneurs that we can work with & build businesses with over time. So we’re old fashioned in the way that we believe in real leadership, really owning a decent chunk of a company, really partnering with entrepreneurs & then we try & be useful in the sense that we try & be transparent & honest & fast & have a lot of the brand qualities that I think an entrepreneur is looking for in terms of finding an open minded, evidence driven, pragmatic partner, that’s willing to do some real work with them.
Fred Destin

Fantastic & I know I’ve been following your blog for a few years & I know that you do write some amazing stuff & some great exposes in the past. Thank you.

Thank you I appreciate that. I think that a lot of the issues that we’re faced with are down to inappropriate communication or perceived lack of transparency. I do try & fight that by being as open & frank & as candid as I can around the entrepreneur versus vc relationship or the entrepreneur versus angel relationship.
Fred Destin

Yes & it just encourages so much trust in the community, that sort of transparency. Thank you. What percentage of women startups do you get pitches for? And what percentage have you funded?

We were running an event here recently in Boston (we do Founder Events & then we do CEO Events) & this one was a CEO event. Its either the people we’ve backed or its people that have made money for us, it tends to be more mature types. We had Scott Kirsner and he was there talking about the necessity of having a more diverse ecosystem in Boston, what Boston could do better & suddenly I semi interrupted him & stood up & said ‘Listen by the way, there’s 50 of us in the room here & there’s only 1 woman!’ And it turns out I’d invited her, a newcomer to the scene, it was Gina Ashe from Krush. She was the only female entrepreneur in the room. So I think there is a long, long way to go, this was striking evidence that it’s rare & continues to be rare, no question!
If you’re asking how many we’ve funded, we do have a few. We have in fact some phenomenal female execs. So I backed Helene Monat @ adsafe media whose really been there since the start in helping structure that firm. We have backed Mara Aspinall ON-Q-ITY here in Boston who is a life science’s business focused on cure for cancer in particular circulating tumor cells in the human body. She’s a female exec, she’s a fairly dominant type of CEO & a great performer! So we have a few, but just like everybody else I will tell you it remains the minority. It’s true if you look at the venture funds as well as looking at the companies that are backed which I think is part of the problem.
Fred Destin

Yes as Mark Suster says ‘It’s a Numbers Game!’ I think. Have you noted differences with women entrepreneurs in how they pitch & build businesses?

Well I think it is very difficult to not fall into broad generalizations when you’re trying to answer that question frankly. To a certain extent, I almost don’t want to insult the women I work with & pigeon hole them. I will say one thing though. Let’s take Paypal for an example. There’s a good body of evidence that Paypal became such a fabulous company because it had a lot of diversity. Diversity in the sense of sometimes complex talent with people coming from very different walks of life. So Elon Musk who went on to create the electric car company, Tesla, well the rest of the team had highly varied background. There’s a recognition that a richness comes from diversity. You really need, especially in the age we live in, where there’s a lot of lateral thinking that happens between biology, chemistry, IT etc, you need a lot of lateral thinking, you need different ways of doing things! The only certainty is the lack of certainty, in other words we live in a world of continuous change! And diversity is the best response you can have to that! So I would just consider that have female people in your company, having women you can work along with is a strong factor of diversity. And I’m just amazed that more people don’t leverage that more!
Fred Destin

Yes I interviewed a woman entrepreneur & she said that its a reflection of what’s out there in the world which is gender diversity! So if you have that within your company you can then target your markets in a more balanced way, which I thought was a really good point. Cindy Gallop, Founder of IfWeRanTheWorld, said in a recent interview: ‘VCs fund in their own image: white, male. The cycle is self-perpetuating, so (predominantly male) VCs have a preconceived notion in their heads of what they think constitutes the kind of entrepreneur to back. John Doerr apparently said, ‘If you’re a white, under 30, tech geek with no social life and a Harvard/Stanford dropout, line up for VC money.’ He didn’t say ‘male,’ but he might as well have. If it had been a 17-year-old Russian girl who came up with ChatRoulette would there have been as much interest in funding whatever she might do next?’ What is your take on this Fred, & if this is happening how can women startups find an opening in this culture?

Well so the venture world probably favors a style of leadership that is highly directional. It depends on how well your Board listens but a bunch of the Boards I’ve been involved with are basically an environment where influence matters a lot. And where people expect you to show extremely strong direction. A lot of times you are basically faced with 4 or 5 white males from Stanford or Harvard, whatever they may be, expecting a lot of direction. So it’s not a natural environment where you if you don’t belong to that world, whether you’re a female or whether you’re Russian or both, where it’s particularly easy to express yourself. Because there are almost unwritten rules of the game as to how you manage these environments. Now I think the good news is that we’re moving towards a world where look at the work that Brad Feld has done; we’re moving towards a world where there is a lot more acceptance of our own ignorance. And I always posit ignorance as a starting point, in other words I’m not sure it’s going to work but I’m for sure going to measure it. But I don’t know at the outset what the recipe is for success because I don’t think there is one. I think there is a lot more open mindedness that should help. You know female leadership style has more to do with building consensus, with being a leader who’s accepted by skills & ability to take input etc. So maybe this leadership style may be more efficient but not one that people are used to in the venture environment. Of course people fund within their zones of comfort. Because the venture game is so much about long term trust relationships & whether you fall in love with a project, the people running it & whether you know you have the feeling that you’re going to be able to count on them. So anything that is a strong affiliation, whether it’s ‘I recognize myself as younger’; ‘We come from the same university’; whatever it may be, it helps people get over these hurdles. A challenge that the venture industry has to embrace is, which is hey you know there are actually a lot of ideas that are way outside your normal comfort zone that may deliver outsize returns that don’t come from this typical profile. And you know maybe women fit that mold too??
Fred Destin

So encouraging them to be more risk or adventuresome?

I’ll tell you what I would say, generally speaking, I think when you’re going into entrepreneurship & you’re going to meet entrepreneurs, the women that I’ve seen that do best are women who are absolutely willing to embrace who they are. So there is absolutely no attempt at being tougher than the boys or whatever it may be? In fact you use humility frankly & female characteristics to their full. You’re just not ashamed to be a woman! You’re absolutely are who you are! You’ll dress the way you feel like dressing! That gives you inner confidence to be more yourself in these environments & ultimately if you can’t be yourself & you can’t make it without faking who you are, you’ll never make it! So I think we’ve moved very far away from an environment where it was recommended that women try & fit into a certain mold. I think in the world of entrepreneurship, a Caterina Fake or a Gina Ash or whoever it may be, are very complete personalities. They are very awesome personalities & every instance of successful women entrepreneurs I can think of are people who embraced who they are. And by the way the same is true for a geek. If you’re a geek don’t pretend to be a businessman. You good as a geek! It’s about embracing your inner actor in a way when you go & pitch to vcs & when you go & play the game of being an entrepreneur. I think it’s difficult enough that if you can’t fully be yourself you might never make it, so you might as well completely embrace who you are. Embrace everything idiosyncratic about you & turn it into strength.
Fred Destin

Cindy also says: ‘I think not as many women as men actively seek VC money because they’re not as tapped into the boys network as male entrepreneurs are. Young male entrepreneurs can very easily become the flavor of the month and get introduced around from one VC to another — get the perception going that they’re ‘hot’ and get their funding. It doesn’t happen for women that way.’ Do you think that networking with Venture Capitalists is harder for women entrepreneurs?

I’ve never really thought about that angle. I think in the US market, which I’m new to, its very much trusted by Stanford & Harvard. If you mapped the vc population back to these 2 organizations, you’d probably find more than 50% of practitioners come out of that school. So I would surely see that that would be a definite advantage. I would however tend to discount that argument a little bit because I think fundamentally most people within our world want to help entrepreneurs, despite all the bad press that may have been out there! People do this job because they like entrepreneurs because they want to interact with them, they want to help them build a business. Whether you’re a male or female, I mean I don’t know, who cares? If I can turn the argument on it’s head about the old boys network? If you’re a charming woman & people like interacting with you because you’re a charming woman, that can be an advantage too! And maybe I’m speaking out of school here but the fact that you bring a different flavor could be an advantage too!
Fred Destin

Thank you that’s a really great perspective.