Interview with Heidi Roizen (Heroes)
Born and raised in Silicon Valley, Heidi spent the first part of her career founding and growing tech companies. Now she enjoys helping entrepreneurs build companies as a coach instead of a player.
Currently Heidi Roizen is CEO of SkinnySongs, which she launched in January of 2008. SkinnySongs introduced the first-ever collection of radio-hit-quality music in which the lyrics are specifically designed to motivate people to reach their weight and fitness goals. Roizen conceived the idea, wrote all the lyrics, then recruited music industry veterans David Malloy and George Daly to bring the project to life. The SkinnySongs lineup also includes apparel, with other products forthcoming. Roizen and SkinnySongs have been featured widely, including appearances on The Martha Stewart Show, CBS Early Morning, Oprah and Friends Radio and CNBC’s Big Idea. SkinnySongs is now available on Amazon and iTunes.
Roizen also serves as a member of the board of directors of Online Resources (Nasdaq:ORCC). Online Resources powers web-based financial services for thousands of financial institutions, billers and credit service providers, serving more than 10 million end-users and processing over $100 billion in bill payments annually. Based in Chantilly, Virginia, the company is recognized as one of the nation’s fastest growing technology companies.
Prior to founding SkinnySongs, Roizen was (from 1999 to 2007) a Managing Director of Mobius Venture Capital, a technology venture fund with $2 billion under management. In this capacity, Roizen served on the Boards of Directors of numerous private and public companies. Roizen was also elected to the Board of Directors of the National Venture Capital Association – the largest venture capital trade association in the world – in which capacity she served from 2003 to 2007. During this time, Roizen served on the Executive Committee, chaired the annual conference, chaired the Public Outreach committee, and chaired the NVCA’s MAGNET initiative on national competitiveness. She also served on the board of Great Plains Software (was NASDAQ:GPSI) from 1997 until its acquisition by Microsoft in 2001, and also served as a Public Governor of the Pacific Exchange from 1996 to 2000.
From 1996 to 1997, as Vice President of World Wide Developer Relations for Apple Computer, Roizen was responsible for building and maintaining relationships between Apple and its developers worldwide. She and her 300-person team served as the primary contact point for major partners such as Microsoft, Lotus and Adobe, as well as 12,000 other firms, emerging and established, which provided products for the Apple Macintosh.
From 1983 to 1996, Roizen was CEO of T/Maker Company, a developer and publisher of personal computer software, including WriteNow™ and ClickArt®. Roizen's principal functions at T/Maker included strategic planning, product planning and acquisitions, partnerships, fundraising, recruiting and directing the senior management team. T/Maker was acquired by Deluxe Corporation in 1994, at which time Roizen also became responsible for the management of T/Maker under the Deluxe corporate entity. Roizen was also elected to the Board of Directors of the Software Publishers Association (SPA) -- the largest software trade association in the world at that time – where she served as a director for eight years, including serving as the SPA’s President from 1988 to 1990.
Heidi Roizen has been active in numerous charitable organizations, educational institutions and nonprofit entities. She currently serves as the Co-Chair of the Stanford Graduate School of Business Women on Boards Initiative, a committee of the Women's Initiative Network. She is a member of the Board of Advisors of the National Center for Women in Information Technology, and of Springboard Enterprises. She was for many years a board member of the SDForum, the largest association of independent software development professionals in the country. She is a past board member of the Stanford Alumni Association, and also served on its Trustee Nominating Committee for five years. Roizen also served on the Board of Advisors for Stanford’s Department of Humanities and Sciences. She is a frequent guest speaker at business schools across the country, and is the subject of case studies authored by both the Harvard and Stanford Business Schools. Roizen has been named to numerous ‘top’ lists, including the most recent ranking of the “Top 50 Women in Tech” by Corporate Board Member Magazine.
In September of 2008, Heidi was named the Forum for Women Entrepreneurs and Executives 2008 Annual Achievement Award Recipient.
Roizen holds an undergraduate degree from Stanford University (1980) and an MBA from the Stanford Graduate School of Business (1983). Roizen resides in Atherton, California with her husband, orthopedic surgical oncologist David G. Mohler, M.D., and their teenage daughters Niki and Marleyna.
An Interview with Heidi Roizen Managing Director, Mobius Venture Capital
Date: August 15, 2007
NCWIT Interview with Heidi Roizen
BIO: Heidi Roizen has spent her entire life in the entrepreneurial ecosystem of Silicon Valley, first as an entrepreneur and ultimately as a venture capitalist helping other entrepreneurs build the great companies of tomorrow. She is currently a Managing Director of Mobius Venture Capital, a venture fund with over $2 billion under management. In that capacity, Heidi serves on the Boards of Directors of Reactrix, Ecast, Perpetual Entertainment and AuctionDrop. Heidi began her career in 1983 by co-founding T/Maker Company, a software publisher and developer for early personal computers including the IBM PC and the original Macintosh. As CEO, Heidi led the company for over a decade, raised two rounds of venture capital and ultimately consummated a successful acquisition of T/Maker by Deluxe Corporation. In 1996, she joined Apple Computer as VP of Worldwide Developer Relations. After one year at Apple, Heidi decided to return to her entrepreneurial roots, this time as a Mentor Capitalist and ultimately a Venture Capitalist. Heidi has also been actively involved in the trade associations critical to the Valley. She is a past president of the Software Publishers Association and served on its board from 1987 to 1994. She also represented the venture industry as a member of the Board of Directors of the National Venture Capital Association from 2003 to 2007. She also served on the board of Great Plains Software from 1997 until its acquisition by Microsoft in 2001, and is a past Public Governor of the Pacific Exchange. She is also a frequent guest lecturer at Stanford as well as a speaker at conferences for technologists, entrepreneurs, or women executives. Heidi holds a BA and an MBA from Stanford University. She is married to orthopedic surgeon David Mohler and has two daughters.
Lee Kennedy: Hi. This is Lee Kennedy, board member of the National Center for Women and Information Technology, or NCWIT. And this is part of a series of interviews that we're having with fabulous entrepreneurs, women who have started IT companies in a variety of sectors, all of whom had insightful stories to tell us about being entrepreneurs. With me, I have Larry Nelson, from w3w3.com. Hi, Larry. How are you doing?
Larry Nelson: Oh, great. It's wonderful to be here again. And one of the things that is so exciting for us at w3w3.com is that we are helping support, I think, the most fabulous program that we've experienced since we got in the radio business in '98, and the idea that we're helping inspire young women, girls, getting into IT, looking into that, as well as being an entrepreneur. But now, we're also getting phone calls from business leaders, people in schools, who say, "This is such a great program. We'd like to help promote it, too."
Lee: Well, that's wonderful.
Larry: One of the interesting things that we have here that's a little bit of a twist is that we're interviewing an entrepreneur who became a venture capitalist, and also, of course, then, therefore works and helps support entrepreneurs. And we're very pleased that we're interviewing Heidi Roizen, who is a managing director of Mobius Venture Capital. And we've got a little bit of a twist here. Lee and I are here in Colorado, and Lucy Sanders, the CEO and founder of NCWIT, is in California, at Heidi's home base. So, Lucy, let's get started.
Lucy Sanders: All right. Hi, everyone. I'm sitting here with Heidi in her beautiful home in Atherton. I've been here a few times, and I just think it's so much fun to be here and interview you here in your office.
Heidi Roizen: Well, thank you. I hope the dogs don't participate.
Lucy: Or they might. They might have something profound to say.
Heidi: They often do.
Lucy: One of the things that makes it so exciting to interview you is that when I think, about Silicon Valley, I think, about you. And I think that you're synonymous with Silicon Valley. You've done a lot, as Larry mentioned. You've started companies. You're in venture capital. You were educated here at Stanford. You're a part of the community...
Heidi: I was actually born at the Stanford Hospital, which I think, I'm probably the only one in Silicon Valley...
Lucy: And why don't you spend a minute or two bringing us up to speed about what you've been doing lately?
Heidi: Well, I am currently serving on four boards. They keep me very busy. They are all companies that are definitely not in their "two guys and a dog and a laptop" stage any longer, but they're all still companies that aren't through to the end of the road yet. So, lots of interesting challenges in terms of recruiting, customer acquisition, strategic business development, and all the normal things one goes through in startup land. So, I'm working on those companies, and then I'm working on a few entrepreneurial ventures on the side, helping out some friends. I always love having my fingers in the very, very early stages, and so I like having a few of those to work on as well.
Lucy: Well, and I happen to know you're very generous with your time for nonprofits and for Stanford students.
Lucy: The last time I was here, we had a great dinner, where you brought them back to your home. And I think, you're going to have some great advice for us, so why don't we just get right to the interview?
Lee: Well, Heidi, I'll jump in and ask our first question, and that's: how did you first get into technology? Was it when you were a child or in college? And then, what technologies do you think are really cool today?
Heidi: OK. Well, the first question is one that I think, if you're born and raised in Silicon Valley, at this time ‑ born in 1958, graduated from Stanford, undergrad in 1980 ‑ you couldn't help but apply for a job and end up at a tech company. So, even though I was not a technologist ‑ in fact, my undergraduate degree is in creative writing ‑ I ended up as the editor of the company newsletter for a little startup called Tandem Computers.
Heidi: And that's really where I got my first inkling that there was something really exciting about the computer industry. What I realized, at that time, was I kind of looked around, and everybody getting ahead either had an engineering degree or an MBA. And it was a little late for me to go get an engineering degree, I thought, but I figured the MBA thing looked like a pretty good idea. So, I went back to Stanford and got that, and really fell in love with personal computing at the time. It's hard for people... I mean, I sound like such an old geezer when I say this. But, I was the class of 1983, and there were only three people ‑ I was one of them ‑ who owned their own personal computer at school. And now, can you imagine being a graduate student and not having a personal computer? You'd be hopeless. So, started my company right out of school and just never looked back. I had the good fortune to have a brilliant programmer as a brother, who really didn't like the business side, and I loved the business side. And the thing I like to tell people, often, who are non‑technologists, who wonder about being in the technology field, I tell them, "You know, need a mix of people." I don't have to know how to build a car to drive one. And in fact, I'd say, particularly in my early times working with my brother, who was the genius programmer, sometimes he'd build features that were so genius that only he could use them, and they weren't very practical. So, I think, sometimes it's good to be the petunia in the onion patch, as I used to call it in the development hall.
Lucy: Tell us a little bit about the technology that you're thinking about as being the next wave of technical, cool gadgets.
Heidi: I think, gadgets is always a slippery slope, because there are gadgets that I just love. I mean, we're investors in Sidekick and Sling, so we definitely have some gadgets companies out there. If any of you have seen a Reatrix system in the malls and in the theaters, and the Reactive television systems, or an Ecast jukebox ‑ we've got tons of portfolio companies I can tell you about that all have exciting gadgets and technologies. To me, where I'm focused right now is I've been thinking a lot about the demographic that is me ‑ the woman who still wants to look good and feel good, who has more free time, who has more money, who, however, still has family obligations, has a career. We're hitting 50, and when our parents hit 50, we thought they were pretty much close to death...
Heidi: Now, we are shocked to find that we are 50. And I think, what's interesting is that the Silicon Valley ‑ and it's a little bit like Hollywood ‑ get so focused on youth and the youth culture and the spending money that youths have and advertising to youths. And while I've got nothing against young people, I think that the people my age and women my age have been an underserved demographic, when it comes to utilizing the web as a medium for exchange, as a community, as an outlet for all sorts of things and a place to go learn about things. And I'm seeing more and more activities around that, and I can't tell you how many times... this is probably hitting all of my same‑age brethren entrepreneurs, but we're all sort of getting up and saying, "I don't really want to start the next teen cell phone. I really want to start something that my friends and I could use." And so I'm seeing a lot of really interesting companies come about, a lot that combine community with some of the really innovative things that can be done online.
Lucy: Give it some time.
Lucy: Give it some time.
Larry: Yeah, you bet. I'm not that old yet. But, anyhow...
Lee: That's right, Larry.
Larry: They're laughing...
Heidi: Somebody once asked me to predict the future of venture investing, and I said, "Just about the time we finally invest in the ultimate weight‑loss pill and the instant‑tan pill, culture will change so that it's not cool to be thin and it's not cool to be tan, and we'll lose again."
Larry: Oh, boy. My personal friend, Mark Twain, said, "Youth is wasted on the young."
Heidi: That's right.
Larry: Anyhow. I can't help but ask this, Heidi. Many people don't look at venture capitalists as entrepreneurs, but anybody who is a managing director, believe me, they are entrepreneur. But, of course, Heidi has the background and experience of being an entrepreneur. She's now continuing to support and work with entrepreneurs. What is it about you that makes this all happen? And what makes it tick, in terms of an entrepreneur?
Heidi: Well, there are so many answers. And I've had the pleasure to listen to many of your wonderful speakers on this series before myself, and I think, a lot of things have been mentioned about tenacity and creativity and mission and a passion about what you're doing. There are so many things that I can think of. And of course, if you look me up on LinkedIn, I refer to myself as a "recovering entrepreneur," which is a little bit of an inside joke at Mobius. We're recovering entrepreneurs.
Heidi: I think, what I had to learn, going from being an entrepreneur to being a venture capitalist, is it's like being the quarterback and then being the coach. When you're a venture capitalist, you do work behind the scene, you do help a lot. But, they're sort of not your losses, and they're not your victories. And if you're doing your job right, the entrepreneur is on the cover of "Time" magazine, not you. When you're an entrepreneur, the buck stops here. It's funny. I just went on a walk with a fellow entrepreneur of mine, and he was talking about a friend who used to be a vice president of a big company and is now the CEO of a small company, and one of the things he was saying to her is, "Now you understand how the buck really stops here."
Heidi: And I think, for me, what really defines an entrepreneur is something that somebody said to me once. When I was running T/Maker, we had this product line called ClickArt, which is still around today, and it's basically electronic clip art. But, you have to remember, when we did that product in 1984, there were no scanners; there was no PostScript; there was no anything. We were literally sitting artists down, at 128K max. We didn't even have a stylus. They were drawing with the mouse in 72 DPI to create electronic clip art. I mean, that's as basic as it was. And when we shipped that product, I remember staying at a trade show, and I can't remember how many people came up to me and said, "Wow! You know, I thought of that, too." Right? And in the back of my mind, I thought, "Yeah, you thought of it. But, we did it."
Heidi: And I think, for most of these things, it's that "one percent inspiration, 99 percent perspiration." There are so many ideas that just die on the vine because a person doesn't go out and try to actually do them. They think they're a cool idea, but other things get in the way and they don't really work hard at it. And not only do they not work hard at the creative process, but the process I'll loosely call is the destructive process. With entrepreneurs, one of the things I respect the most is, when you come up with an idea, that instead of working on it for the first five days about how you're going to accomplish it, you spend five days trying to prove that it's already been done or it's not doable ‑ not because you're being pessimistic, but before you engage in the creative process, sometimes you have to go and say, "What else is already out there?" And one of my pet peeves as a venture capitalist is when somebody comes and pitches me an idea, and I say, "Have you ever heard about blahblah.com?" And they go, "What's that?" And I get on and I show them, and it's the exact company they were talking about building, but it already exists. My feeling is, today, particularly with Google and other search engines and the Internet, you can find a lot of this stuff out there, and you need to go out and look. But, I do think, ultimately, a long and winding answer, but the short answer is it's like Nike, man. It's "just do it." If you just do it, that's the only way to be an entrepreneur. If you're not willing to just do it, you're never going to be an entrepreneur.
Lee: That is such great advice, Heidi, because so many people, even when they just go out and do it, it's not that first idea that they even end up doing sometimes. It's just having the guts to get out there and start the business and get in that industry and figure out what it is.
Heidi: That's right. And ask a lot of questions and meet a lot of people and kiss a lot of frogs.
Heidi: It's always easy, in retrospect, to say, "Why did I take that meeting with that person?" But you don't know because, just as likely, you could take a meeting with another person. And I just had something happen this weekend, where I was helping someone on a music project. And we were talking to someone who was totally unrelated, and they just said, "Oh, what are you up to?" Totally unrelated to the music industry. And we told him what we were doing, and he said, "Hey, I'm good friends with..." And I won't name the names because it's all proprietary, but let's just say one of the most Grammy‑winning artists in the world. And he said, "I'll give him a call tomorrow and see if he's interested in helping you with this." So, it's like one of those random, like that's not what we were even there to talk about. But, that's how the conversation ended up going, and it could take us in a really exciting direction. You just never know when that kind of serendipitous stuff is going to occur.
Lucy: Your remark about 1984, when you were doing T/Maker and you had to have the ClickArt, I just have to go back to that for a moment and say, in 1984, we were trying to draw things in P‑Roth inside...
Lucy: That's not revolutionary.
Heidi: Yeah, yeah. I remember the first time I showed my husband QuickTime, whenever it came out ‑ 1989, whatever. And I'd bring home my file, because we were under nondisclosure with Apple. And I'd show him this postage‑sized, grainy thing, and he goes, "Wow. I am really underwhelmed."
Heidi: For me, as a computer geek, it was so exciting to see television on a computer. And for him, he was like, "Uh, honey? Have you looked at our TV set? It's like a lot better than this."
Lucy: Because I know you, I think that one of the things that makes you a great entrepreneur is, in fact, you see potential, and you're willing to take the risk to develop the potential.
Heidi: Yeah. It does make one quite dangerous. It's that joke about the person who buys houses because they see the good in every house. And I tend to be a person who sees the upside in things. Which I think, again, in order to be an entrepreneur, you have to be an optimist. You have to believe things are going to work out your way. But, you have to be realistic. And that's where I, again, for lack of a better word, call it the destructive process ‑ testing your idea, going out and thinking about the boundary cases: "What's the worse that could happen here? What's the worse that could happen here? How am I going to prepare for it?" And also going out and really combing the markets to make sure that what you're doing is unique, or, if not unique, that you're going to be the best somehow.
Lucy: Well, along the way ‑ you've been here in Silicon Valley. You were born here.
Lucy: And you've got a great network. And we are really curious to also understand who helped you the most. Who would you look to as being your mentor?
Heidi: I was very fortunate to be born into a family where entrepreneurship was not a bad thing. I think, it's one of the things that makes California such a great place and will play a continuing role in the world economy is because we are just a culture, for 150‑plus years, of people striking out and doing something on their own, and failure not meaning social failure. You can be a business failure and still hold your head up and go to your kids' school and not be embarrassed about it.
Lucy: "I failed today."
Heidi: "I failed today." It's part of the process. I think that, for me, my father was a great role model for me because he was an entrepreneur. He was always thinking. He would say things to me like, "Today is the best day of my life because I have every day before today that I can draw on what I learned to apply to today." So, he was just that kind of person. And he wasn't like Mr. Rogers. I mean, he was just a great role model about how one could look for the opportunity in everything. And he was a very poor immigrant. I think, he graduated from high school. I'm not really sure. His dad died when he was 12, and he had to make money for the family to make ends meet. I mean, he had one of those really hard upbringings that made him very grateful and thankful, and very creative and resourceful. And he treated me like one of the boys. He never said to me, "Oh, you're a girl. You shouldn't do this," or "You can't go to graduate school," or "You can't do anything." In fact, if I said I couldn't do something because of being a woman, he would scoff at me. And my brothers joke that I'm the most like him...
Heidi: So, he actually made me in his image, not my brothers. But, I was very lucky about that. I was very lucky, also, just to be in the computer industry in the late '70s and early '80s, because I really did get to grow up with the people who are the leaders in the industry. And so somebody said to me, "Wow! How did you get to be friends with Bill Gates?" And it's like, "Well, started 25 years ago." [laughs]
Heidi: He was easier to get to then. But, it's things like that, that I think, I just had the great fortune to have a front‑row seat and be a participant in an industry that I really believe has changed the world. So, it gave me a lot of opportunities to learn from other people and have mentors and role models.
Lee: So, Heidi, when you think about all you've done in your career ‑ building your own companies, being an investor ‑ what has been the toughest thing you've had to do in your career?
Heidi: You know, you face so many tough challenges when you are the CEO and "the buck stops here." Someone once said to me, "Gosh, you're so lucky. You're the CEO. You have so much freedom." And I laughed, and I said, "You don't understand that when you're the CEO, you have the least freedom, because you can't just quit." I raised that money. I hired every one of these people. I gave those venture capitalists my commitment that I was going to bring it home for them. I'm not just going to walk out the door. I remember walking into my company every day. We had about 100 employees. And I would count the cars in the parking lot, and I would think about the car payments and the mortgage payments...
Heidi: Everything that was dependent on this company. And so I would say, still, to this day, that the hardest thing you have to do is lay people off. I mean, the hardest thing you have to do is downsize your firm. It's not as hard to fire someone. This is an interesting thing. I would much rather terminate somebody for cause than lay people off because we can't afford it. When you terminate someone for cause ‑ and "for cause" is a real legal term. I don't want to use the legal definition of that. But, what I really mean is, when somebody's not a good fit for the job they're in, I find that it's really in their best interest to tell them and get them to move on to something else. And while that is sometimes hard, I think, it's the right thing to do, and I think, it's the right thing to do for the person. And I've often found that you check in with them a couple years later, they're better off where they are, even though this can be very difficult. I do think, going through the dot‑com bust and having to lay people off, knowing that there wasn't going to be another job they could just waltz into, was a really, really hard thing to do. To me, those were the hardest things I ever had to do. In fact, my T/Maker employees still joke about this time where we had our first loss ever and we had to lay off some people, and it was Christmas. I was about four‑months pregnant. I said to my husband, "I've got to do it myself. I hired all these people. I'm going to do it myself. I'm going to give each one of them the news." So I'm in my office, and they're coming in, or I'm going to their offices. And I'm pregnant, and so the hormones coursing through my veins. So, I am sobbing through these terminations, and they are comforting me.
Heidi: They feel sorry for me. But, I have to lay them off. Sobbing, sobbing, sobbing. And I say to my husband, "This is the worst business day of my life, where I'm terminating some people who've been with me five, six years, and I just feel terrible. And it's Christmas, and I had to tell them, 'No bonuses for you guys, and you're getting laid off.'" I said, "Please go to Blockbuster and rent a funny movie so that when I get home, I can take my mind off of it." So, I come home, and what had he rented, but Chevy Chase's "Christmas Vacation."
Heidi: And I don't know if you guys have seen this, but of course, the whole story is about a guy who believes he's getting a Christmas bonus and builds a swimming pool or something, and then he doesn't get the bonus, and he ends up kidnapping his boss.
Heidi: It was just one of those moments: I just didn't know whether to laugh. I'll never forget that moment. I still cry when I see that show. It was on TV last Christmas, and I'm like crying through it. My kids are looking at me. They're like, "Mom, it's a comedy." Not for me.
Lucy: Not for me. In fact, my answer to this question is the same. I think that laying people off is clearly one of the hardest things that I've ever had to do.
Lucy: We've heard a lot of great advice so far in this interview from you about entrepreneurship, and the Nike "just do it," and who cares if you've thought about it? Just get it done.
Lucy: And other types of advice around doing your homework and seeing the potential. If you were sitting right here with a young person and you were giving them advice about entrepreneurship, what else would you tell them? And one of the things that comes to mind is a conversation we had sometime about networking.
Lucy: And I thought you had some of the best advice about networking that I've ever heard.
Heidi: Well, I have a ton of advice about networking. I'm a little typecast as a networking speaker because Harvard did a case on me a number of years ago that really is about my philosophy of networking. And when they approached me to do the case, I said, "Why would anyone want a case on this? It's all just common sense." It's kind of like that book: "Everything I needed to know about networking, I learned in the second grade." But, it's just commonsense and practical and courtesy. And so, they did do this case, and I do speak on the case a lot. And my fundamental belief is that it's very rare that anything happens as a singular effort. Yeah, you can go climb ‑ well, even climbing Mount Everest, it's a team, right? And entrepreneurship is a team sport with very many lonely moments. So, you have to be the one. I'm working on this project with someone. I got up at four o'clock in the morning a couple of days ago because I thought of something, and I knew if I waited till morning, it wasn't going to be the same. So, I had to get up and come down here and sit at the computer for an hour and write up my thoughts while they were fresh. I think, there are a lot of times when you're just singularly approaching something, but I think, you have to know how to ask for help, and how to give help. Students say this to me all the time, they say, "Well, I don't have anything to give." You always have something to give, everyone has something to give. Good lord, you can come and talk to me and baby‑sit my children while you're talking me. I had one guy who traded me, I would talk to him about his business and he was a personal trainer, so he would train me while I was talking to him about his business.
Heidi: And I think that one of the errors that people make in networking is they try to hard to gather business cards, and they don't think about "What is my connection with this other person, and what do I have to give them? What in return am I going to ask them for?" Again, I will bring it back to this other comment, a lot of times you don't know how the other person is going to help you, and you're not quite sure always how you're going to help them. Sometimes, it's quite surprising, but if you put yourself open to that, and you use some of the modern tools ‑ like I've become a real LinkedIn convert, because I love being able to get on LinkedIn and see who my friends know that I might want to talk to about industries completely foreign to me and vice versa. If somebody has a good friend from college who now wants to do something in the out of home advertising market and sees I'm on the board of Aventure and would like to talk to me. I don't mind doing that stuff because I sort of feel like there's this great, you know, we all help each other in this community and I'm a little bit of a believer in that kind of pay it forward. It's interesting right now because in Aventure I'm working closely on, I have to reach out and ask for a lot of favors, and I've been very aware that for a lot of my current roles in life I'm the one that asks for the favors than asked. Now that I'm doing the asking it's interesting, I'm uncomfortable. I'd much rather do a favor for someone else than ask somebody for a favor. It's my nature, and it's the nature of many people. But, I think that you have to get good at understanding "What am I asking for? Is it appropriate for me to ask it? Is the person capable of delivering it? Is it an appropriate amount of time for them to send and do something for me? And what could I possibly do for them?" I always try to make sure that people know I'm quite open to doing something for you in exchange, and by the way, no is a perfectly good answer, too. If I ask you a favor and the answer is no, just tell me no. I'm very comfortable with that.
Lucy: That's great advice because so many people they really are either afraid to network, or don't know how to network, and that just makes it really clear.
Heidi: Networking is also very awkward; somebody from Stanford called me up once and said, "Can I network with you?" What is that is that like my pen pal or something?
Lucy: Just network.
Heidi: Let's say you want to meet someone, and I guess, with the powers of Google and the Internet and all that, you might want to meet some important person. If you have no context, it's going to be a very fruitless conversation. But, every one of them, their kids go to school, they are on a charitable board, they may enjoy a certain kind of athletic activity. I'm not saying become a stalker, but generally, for example, if you want to get to know a person and they happen to be on the board of a charitable organization go find out what the annual fundraiser is on that charitable organization and volunteer to work at it. Chances are you're going to be able to meet that person over time if you get involved in something like that. And, by the way, you're doing something good too. That's again, one of the powers of Silicon Valley ‑ both good and bad ‑ you've got to be careful, you've got to find out if other moms and dads on the soccer sidelines have MBAs because everybody's kind of in this business.
Heidi: It is interesting that you have so many different places where you meet and run into people, and so many people I do business with are friends of mine in other context.
Lucy: So Heidi, you had talked earlier in the interview about different characteristics that you thought were really important to help entrepreneurs grow and build companies, but when you think about yourself, what are some of your personal characteristics that you have that have helped you to be successful as an entrepreneur?
Heidi: Certainly tenacity. I mean, I'm very tenacious about... you put me on something I'm on a mission and I'm not going to let it go. I like to learn new things, so I like to push myself and try to learn something new. I think, when you're constantly learning it helps you get a better job, [laughs] and in so many areas. I'm definitely a people person, I love talking with people, I love meeting people. I'm very comfortable asking people for their opinions and I think, I'm a pretty good listener. So, I think that that also helps me be an entrepreneur, because you learn from other people, you gather opinions, you mold what you're doing. Frankly, it helps you in terms of going back to asking for favors, giving favors, recruiting people. People generally want to work with people they like and people they respect, which is another thing. My belief is that I'm going to be in this world for, I hope, a pretty long time. One thing I've learned being almost 50 and being in the Valley all this time is that you run into the same people over and over and over again. So, don't burn a bridge unless you've decided that's the best course of action. I like to sleep at night. I don't like to do bad deals, and I don't like to squeeze the last nickel out of somebody just because I have the upper hand. I like to live that way. While there's always different opinions about anything you do, I try to test everything. Does this match my ethics? Can I sleep at night? If my husband or my kids knew I did this, would they think less of me as a person? I like to live that way. I think, an entrepreneurship is not a zero sum game. Your gain doesn't have to come out of somebody else's loss.
Larry: Boy, I'll say. You know, Heidi, one thing I've learned to do is that I'm going to call you "Coach" from now on. I just want to clarify one little thing. You said something earlier about kissing the frogs, or was it kissing your dogs?
Heidi: Yeah, kissing frogs. Although frogs wish it was kissing dogs.
Larry: Yeah. And you also just mentioned that you should ask for help. Do you want to introduce me to Bill Gates?
Larry: No. OK.
Heidi: That's a good one you bring up, because it is one of those, how do you manage a relationship towards a person who's very important or famous? One thing I had to decide early on is, I just set certain rules. And I've gotten very comfortable saying "No" to people. So, people will say to me, "Can you introduce me to Bill Gates?" And the answer is, "No, I can't," because if I did that for everybody, they would.... And the hardest part is people thinking, "I have the best charity in the world. I have something that would be so interesting to the Foundation. Please help me get to the right person. Can you please send this to Bill and Melinda?" And I say no. One of the things that gives me comfort in saying no is that I say, "Look my own husband runs a charitable organization called Refugee Relief that does medical assistance in countries under conflict. He'd be a perfect candidate, and he hasn't even asked Bill and Melinda for money." One of the things I try to do is live by my own rules. The other thing I try to do is, for example, when I sold a company from my portfolio to Microsoft I didn't even talk to Bill about it. I'm not going to mention, "Hey, I'm selling one of my portfolio companies" to him. It's not relevant. I really try to respect that, particularly people who are in positions like Bill where everyone's approaching you all of the time, you need to be respectful of the pressures on that person's time. I think, that's one of the reasons why Bill and Melinda and I have a good and long‑standing relationship. They know that I respect that there needs to be boundaries there, because they don't have the luxury of living normal lives.
Larry: Yeah, that's fact. By the way, of course, you know I was just saying that to....
Heidi: Oh, I know.
Larry: However, last week we interviewed Brad Feld and he did say, "Hi to Heidi."
Heidi: Oh, that's so sweet. I adore Brad.
Larry: All right. Let me ask you this question. In your approach to your professional life, you do so many things. How do you bring about balance?
Heidi: That's an excellent question. If you'd like I can bring my 12 and 14 year olds in here right now to continue the counterpoint to that.
Heidi: I do try to set limits. In my house, although we have wireless access, I'm not the person who walks around with my laptop and uses it everywhere. We certainly have a "no laptop in the bedroom" rule. I don't tend to watch TV and do email at the same time. I have a home office that I come in to do my work and then I try to leave it. I also try to have a commitment with my kids. If I say, "I'm going to stop working at seven," then I'm going to stop working at seven. I mix business and pleasure a lot. I have a lot of social engagements with people. I have a lot of people over for dinner. I try to engage my kids in some of that, because luckily at their ages they find some of that very interesting. In one of the projects I'm working on right now, I ask them for advice a lot. I've been able to pick their brains a lot about it. And they've been really great. I tell them, you know, if I'm having a bad day, you know I had a bad day about a legal contract I was working on. And because it didn't get done I missed a window of production for something. And I said to them, they said you know, "Why are you in such a bad mood?" And instead of saying something like, "Well, I had a bad day at work." I said, "Well, let me explain to you. This company needs a piece of paperwork before we can contract this production facility. We didn't get the piece of paperwork. Now because this production facility can only do things in, you know, they have another client the next three weeks that pushed me out a month. So, here's a one day delay on a contract that's going to cost me a three week delay on the production. And that's why I'm so mad about this today." And so that what is the thing? A teachable moment right? You know, I try to bring them in to the things that I'm doing. But, it is important sometimes to just close the door and say, "I'm sorry I'm not going to do this." I try very hard not to schedule meetings on the weekends. I try very hard not to schedule meetings at night. I try to really limit my travel because it is very disruptive to my family when I travel. And so, I try to make accommodations. Lucy: Well, and your daughters are wonderful. And having seen them at a couple of dinners. I mean the integration works really well.
Heidi: They're pretty cute. Yeah.
Lucy: They're pretty cute. It works really well because they get to see a lot of different people over here.
Heidi: Yes they do.
Lucy: That they wouldn't ordinarily see. They lead unusual lives.
Heidi: We had a nice conversation about Norwegian and other things this morning. So, it was very good.
Lucy: They were very funny.
Heidi: And they do provide very funny moments. One time actually, Bill and Melinda were coming over for dinner. And Nicky was playing on her Xbox. And she knew Bill was coming over and said like "Can I have him sign my Xbox?" "Oh, I guess, you can ask him to sign your Xbox." Which she didn't ultimately do when he came over because she was too embarrassed. But, she said to me, "Microsoft, yeah, they make the Xbox. Do they make any other products?" And I just had to laugh.
Heidi: You know, the eyes of a thirteen year old is like all they make is the Xbox.
Lucy: Well you really have achieved a lot. And you have front row seats to a lot. And I have no doubt, fifty or not, that you are going to be on the front row for many, many years.
Heidi: Not done yet.
Lucy: Not done yet. So, tell us what's next for you.
Heidi: Oh, I'm so excited about what I'm doing. But, I can't tell you. Sorry.
Lucy: I'm going to jump across the desk and strangle her.
Heidi: I know. I know. I am. You know I'm continuing to do my work with Mobee and then a company that we work on. And Brad and Jake my partners there. I mean, you know, we have a great relationship and I'm enjoying that. But, I am definitely an entrepreneur at heart. In fact I've been thinking, at some point on my link and profile. Right now, it says venture capitalist and recovering entrepreneur. And someday soon it's going to say "Relapsed entrepreneur and venture capitalist" because I just can't help myself.
Heidi: So, I just started a little company. I actually funded it yesterday. I'm fortunate enough to have provided my own seed capital. I joke to my husband. I said, "It's very important tonight because we're having cocktails with my lead investor," which of course was me. [laughter] So, we laughed about that. So, I have a little start up that I'm working on, which I will hope to tell you all about really soon. But, it's not quite baked enough yet. So, you'll just have to wait.
Lucy: I just hope it's about fifty year old women.
Heidi: You will, you will buy one of these products. Well, I'm going to give you one. And Lucy. Larry