Robin Wolaner, Author Naked in the Boardroom: Women must Suspend Disbelief

Video Interview with Robin Wolaner, author of Naked in the Boardroom

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Video Interview with Robin Wolaner, author of Naked in the Boardroom.  Robin is a company founder and former publishing/internet executive; her book, Naked in the Boardroom A CEO Bares Her Secrets So You Can Transform Your Career  , was published by Simon & Schuster in March 2005. She is the Board Chair for Skout Inc She was the Founder & CEO of TeeBeeDee, a social network for people 40+.  Previously she was Executive VicePresident for CNET Networks.
You can find Robin @ her website & on Twitter @robinwolinar
Transcript follows & video above.

  • Could you tell me briefly about your past history in sourcing venture funding?

Sure, well I did it so long ago. The first time was back in 1985 when I was the founder of Parenting Magazine. Because I’m out here, I looked first to Sand Hill Road & vcs for investment. Magazines were really not in their sweet spot. It wasn’t a technology company. I met some guys who became giant vcs later on but Bob Kagle , Tim Draper who made an angel investment in Parenting before he even started Draper Fisher. My dear friend David Nierenberg who left the venture world for a hedge fund that I’m an investor in. So I met great people but it really wasn’t a venture kind of a deal & I ended up raising the money from Time Inc instead. After that the next time I went the venture route was for TeeBeeDee which was a social networking site that I founded in 2005. I raised angel money first & then venture money. So that’s my more recent experience. We closed our Series A in the beginning of 2007.

  • What personal lessons being a woman have you taken out of your successes &/or failures in that regard?

Well I don’t really feel like being a woman had any impact on my raising money. I think what has an impact on raising money (& probably not in this order but the ones that come to mind) are your track record. You have succeeded previously, obviously a great thing, even if you’ve failed previously. I lost all my investor’s money & my own money in TeeBeeDee. Yet when I joined Skout it really wasn’t a factor. In fact several people from prominent venture firms said you learned more by doing that & it’s made you more hands on which is more appropriate for today’s startups. Small startups don’t take as much capital. So I don’t actually think that being a woman had any effect but track record has an impact. Now there are fewer women who have led companies, who have founded companies who have succeeded or failed than men. So of course that’s a factor, there are fewer of us. But once you have that track record I don’t believe that you’re either advantaged or disadvantaged with venture capitalists. I believe that now in today’s kind of startup, in the world that I’m in which is the consumer technology company, being an engineer as a founder is really important. There just aren’t that many women engineers. We know that Larry Summers got fired from Harvard for saying that. I don’t agree with his reasoning but it is true. So every time you’ve got something that reduces the pool of available women whether it’s whether they’re in engineering or whether they’ve had the track record, there’s less for the vcs to invest in. But vcs are complete sheep. They follow the trend, right!

They do.

So if a woman walks in with what they’re funding that week (I’m not saying they all do but the lion’s share of them are lemmings) so if a woman walks in with that hot sector that they’re all funding that week, they’ll fund her company. Whether she’s done it before, female, male or anything in between. They will overlook anything in the race to get in on the next hot deal. So I think that people make more of it.

Definitely more enlightened here than it is in London, that’s for sure.

I’m sure that’s right, I’m privileged to live in Silicon Valley.

I would say so, it’s like heaven here compared to London & Ireland.

It is like heaven here, much as I like Ireland.

  • What attitudes towards you being female have you noted from venture capitalists when you have been sourcing investment?

Not of being female. I’m older now so I see the baby vcs who are really young enough to be my kids, I’m in my 50s. I have a funny story from the days when I was raising money for Parenting. Trying to convince these guys to take a bet on a magazine, they wanted an industry expert to talk to them about advertising because I wasn’t an advertising expert. So I got the woman who was then the head of advertising for the Magazine Publisher’s Association & she happened to be a former Penthouse Pet. I had worked with her at Penthouse. I think these guys thought ‘Oh my God we’ve died & gone to heaven!’ This is what they look like in publishing, very different from Silicon Valley. She was lovely, Scottish actually but they still didn’t invest. I think you could bring in the great beautiful guns but it didn’t matter, they weren’t funding magazines, they weren’t funding mine.

  • What qualities do you think women entrepreneurs need specifically for sourcing venture capital? Many have mentioned women’s intuitive abilities & I quote you “Women get more credit (than men) for being intuitive. Some of the things that stop women from listening to their gut are they hold themselves up to unrealistically perfect standards and so then their gut starts giving them insecurities instead of messages that are really helpful, like ‘oh I’m not qualified for that’ which is not something you generally hear men say. I think women have some real potential for being more emotionally in tune.” Do you think these qualities could serve women entrepreneurs when sourcing venture?

Did I write that? Well it was a while ago & maybe I’ll edit it on the fly now. Because what I think is, in a way it’s bad to be in tune with your emotions when your emotions are making you feel insecure. I had a friend who is an amazing success story today C level exec. She was describing a job that was being recruited & she was telling me all the reasons she wasn’t qualified for it. I guarantee you a man in that position would not have that conversation. So in a way listening to your gut is good but not when it’s giving you the message of ‘Oh, oh heres the hole in my resume!’ Guys don’t do that & women need to stop doing that too.

I wonder if that’s the gut, it may be more the lack of confidence & insecurity rather than the gut feeling?

Yeah so I think that quote is more of a mashup than what I believe. What I believe is that women need whatever it takes to make them feel invulnerable. Basically if you’re going into vcs as a founder, you have to suspend disbelief or you wouldn’t be a founder. The odds are overwhelmingly against you. Most things fail. So you’ve got to suspend any disbelief about your ability to get it done. I don’t know if most founders see the possible problems. I’ve worked with male founders. I’ve worked with female founders. I’ve been a founder several times. I don’t know any of them who fit the image of ‘never doubt, the complete Silicon Valley asshole theory. I’ve met those assholes later in their lives & I don’t think Larry Ellison would ever admit to a moment of self doubt. But the founders that I meet generally ‘Oh my God can I actually get everything to happen?’ & you just have to suspend that. I think in some ways men are better at denial than women.

Yes I have had feedback during these interviews that women tend to be more upfront & realistic.

Self deprecating! I did rehearsals with one of my girlfriends who’s a C level exec herself, has been an entrepreneur in residence venture firms. When I did my pitch (I guess it was for TeeBeeDee) she was like… self deprecating….self deprecating…take it out! So it’s a good tip. Get somebody else.

Great to have a mentor like that heh?

Well I hate the word mentor myself, I call them tormentors. But have a friend, have somebody who’s going to give you the tough feedback.

Written by
Pemo Theodore

Pemo Theodore is a Media Publisher and a great people connector. She was Founder Silicon Valley TV which served the San Francisco Bay Area for 10 years! She has produced Silicon Valley Events for Investors & Startups for 10 years. Pemo loves to video interview venture capitalists & founders to engage the human behind the success stories.. She has been Executive Producer of FinTech Silicon Valley for 6 years, organizing twice monthly FinTech talks & panels in San Francisco & Palo Alto and audio podcasts. She believes in learning through a great discussion with experts in the domains. Pemo has a talent to bring the right people together and is an incredible networker. Pemo's events have been seen as supporting Venture Capitalists & Angels in sourcing great deal flow from startups who attend her events. Many founders have received funding through meeting investors at her events. Her favored medium is audio & visual media and she has built up a great body of work of videos of panels & interviews and podcasts in Silicon Valley startup ecosystem. She has lived & worked in Canada, Australia, New Zealand, Ireland, London, Northern Ireland & Silicon Valley. Bio

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Written by Pemo Theodore