Interview with Ellen Siminoff

June 1, 2009

Series: Entrepreneurial Heroes

Entrepreneurs are "people who would be just dreadful employees", says Ellen Siminoff. For those who go the entrepreneurship route, however, the appeal is in "the idea and the people and the excitement of creating something."

Ellen Siminoff

Ellen Siminoff is President and CEO of Shmoop University, an educational website. Shmoop’s goal is to make everyone a lover of literature, history, poetry, and writing.
Prior to Shmoop, she was President and CEO of Efficient Frontier, a pioneer of dynamic search engine marketing management services. She worked with the founders to evolve Efficient Frontier from a groundbreaking idea into the leading Search Engine Marketing agency in the world with business in the U.S., Asia, Europe, and Latin America. Prior to Efficient Frontier, Mrs. Siminoff had six adventurous years as a founding executive at Yahoo! During her tenure, she led business development (VP, Business Development and Planning), corporate development (SVP, Corporate Development) and eventually ran the small business and entertainment business units, representing approximately 25 percent of Yahoo’s revenue (SVP, Entertainment and Small Business). Before Yahoo! Mrs. Siminoff worked for the Los Angeles Times as electronic classifieds manager, where she developed strategy and implemented the newspaper’s own on-line businesses as well as a joint venture of Career Path with five newspaper companies. With her husband, David, Mrs. Siminoff also founded EastNet, a global syndicate barter company distributing television programming to 14 emerging market countries in exchange for advertising time.
Currently, she serves on the board of directors for US Auto Parts, Journal Communications, glu mobile, and SolarWinds. In 2005 she was one of eight industry professionals named "Masters of Information" by Forbes magazine. She is on the boards of directors and advisors of a number of private companies including and Mozilla Corporation. She is a frequent speaker at industry conferences, including Ad-Tech, Search Engine Strategies, and Supernova. She graduated Stanford's Graduate School of Business with an MBA in 1993 after having completed a summer in corporate finance at Salomon Brothers. Mrs. Siminoff worked as a human resources management consultant in New York after graduating from Princeton University with a bachelor's degree in Economics.

Ellen Siminoff


An Interview with Ellen Siminoff President and CEO, Shmoop University

Date: June 1, 2009

Ellen Siminoff: Shmoop University

Lucy Sanders: Hi, this is Lucy Sanders. I'm the CEO of the National Center for Women & Information Technology, or NCWIT, and this is one of a continuing series of interviews that we're doing with really just outstanding women who have started IT companies. With me is Larry Nelson from Hi, Larry and welcome.

Larry Nelson: I am so happy to be here. This is going to be a very interesting interview. As we get into it Ellen is going to see that there's some similarities between us.

Lucy: Well, that's a pretty scary thought.

Larry: Yeah, it is; isn't it?

Lucy: Ellen, run. Today we are interviewing Ellen Siminoff, and she is the President and CEO of Shmoop University. Now, this site is something that our listeners really must go and see. They have a great mission. Shmoop is an education Website, and their goal is to make everyone lovers of literature, history and poetry. I went there last night and started looking around, and I really like the idea of their Book Club where they review books and even have questions for teachers to use with books, and I thought it was really fascinating that people creating their content, master's degree students and Ph.D. students, really looking for great original and creative content to help students and teachers. I found a little humor on the site as well, so it really cracked me up. Shmoop guarantees better grades. There was an asterisk next to it, and it said: "not an actual guarantee." Anyway, welcome, Ellen, we're really happy to have you for this interview.

Ellen Siminoff: Thanks for the great review of this site. That was great.

Lucy: Well, we're really happy to have you and before we get into the entrepreneur questions, I really wanted to know how you came up with the name, "Shmoop," and what's going on with the company.

Ellen: Well, I started the company with my husband. Shmoop is a Yiddish term for trying to move something forward a little bit. So, my husband's grandmother always used to say to him, "Shmoop this, shmoop that" so we're trying to move education and learning forward a little bit.

Larry: Shmoop, I love it.

Lucy: I love it. Down in Louisiana we used to say we were carrying somebody from here to there, even though you're actually driving them. Now, we can say we shmoop around.

Larry: I'm for shmooping.

Lucy: I'm for shmooping. Well so, Ellen, how did you first get into technology? You are using technology in the delivery of your company, obviously, and so our listeners would really like to know what you're looking at as particularly interesting technologies today. Ellen: I got into technology because I was really interested in media, and media became very important to technology. I started a different company with my husband many, many years ago. It was about 18 years ago, and we were distributing television programming in eastern Europe and that made me love the media industry. Then I went to the Los Angeles Times, and I started running their online Classifieds. This was really early. It was like 1994 when the Internet, and if you remember Prodigy and CompuServe and AOL were all fighting it out. I started realizing that technology could be used to deliver media in a really interesting way.

Larry: Wow, that's terrific. Remember, I warned you up front that there's something that we have in common. First of all, on your Website there's so many things I like about your Website, but I am also, like you, a lover of chocolate.

Ellen: All right.

Larry: I'm a cheese head. I used to live in Wisconsin.

Ellen: All right.

Larry: And I still struggle with golf, so I think that's enough similarities, right?

Ellen: Those are great similarities, but have you been shot?

Larry: No, but I almost shot my dad when we were hunting once.

Lucy: Have you been shot? I'm sure there's more to that story.

Larry: It's on the Website.

Lucy: Oh, I better go look at that part of it. Well so, Ellen, I was sitting here thinking about technology today. Do you see any particular technologies on the horizon that you think are pretty interesting?

Ellen: I'm a big lover of the Kindle. I think the approach Amazon and, obviously, some others in that space have taken about taking a text book and providing a much easier way for students to get their information. I think it's fabulous. I think, first of all, we don't need to have orthopedic problems from carrying around back packs loaded with books, and second, text books are really expensive. They has to be a less expensive way to deliver the same amount of material, so I'm really excited about that one.

Larry: Yeah, I am, too. Now that they've got the new, big one, I like that even more.

Ellen: As I get older, the bigger print would be fine.

Lucy: I see them on planes more and more now.

Ellen: Yes, I actually always bring mine every time I travel because, why lug a book around?

Larry: Right, you bet. Well, I get the part about technology and all, but why are you an entrepreneur, and what is it about you that makes the entrepreneur part of you tick?

Ellen: Well, I think entrepreneurs are people who would be just dreadful employees... because it's chosen for us. For me, I have always sort of gone with smaller companies that I like the people and the idea. When I started Yahoo, we were just a handful of folks, and we thought we were changing the world. Hopefully, we did to some extent. I started up Fischer Frontier which subsequently became the largest search engine marketing firm when it was just a couple of guys with a really neat math algorithm. Shmoop, my husband and I came up with in our back yard. So, for me it's about the idea and the people and the excitement of creating it. The other benefit of being an entrepreneur is you have very little bureaucracy. When a decision needs to be made, you sort of look around at your four or five key people and you resolve it quickly, and that's exciting for me.

Lucy: So, along your path you're a serial entrepreneur and you've had a lot of success along your path, who has influenced or supported you? Who are your role models?

Ellen: Well, if it hasn't become clear, my husband has been really supportive which I think is great. We've worked together a number of times, and he's pushed me more than I probably would have pushed myself. I have phenomenal parents who basically told me dream big and we're your number one fans, whatever you want to do. So, they've been great, and I've had some terrific teachers along the way. Back to the Wisconsin thing, I had a great eighth grade teacher at Mapledale Elementary School who told me, "You might be pretty smart. Think about what you might want to do in life". I was in eighth grade, and I still remember that conversation.

Lucy: Isn't it amazing that you do? That kind of influence on young people by teachers, it really sticks.

Ellen: It's amazing. We actually have a page on Shmoop, a teachers' page, that we literally went to the Ph.D.s and Masters I alluded to before and all of us here at the office have said, "So which teacher influenced you the most?" We wound up with this great list of our favorite teachers and how they impacted our lives. And I think that every person who's reasonably successful can identify one of the teachers who made a big difference to them.

Larry: Oh, that's fantastic. You know, you mentioned you and your husband. My wife and I, we've started 12 different companies over the years, and it's an extra little plus that as an entrepreneur you can do that.

Ellen: That's great. That's inspirational. We have a few more to go.

Larry: Well, OK. I'm just a kid, but... Ellen, what is the toughest thing that you have ever had to do in your career?

Ellen: Oh, I think the toughest thing anyone has to do is ask someone to leave a company when that person is doing a good job, but they're somehow... morals or conduct or behavior goes against what you want your company to do. I think any CEO or hiring person will tell you, that's the hardest call you ever have to make.

Lucy: And, in fact, I think we've done about 50 of these interviews, and that comes up over and over and over again, I think, along with having to leave a company you don't want to leave.

Ellen: Yeah, transitions are very hard. I think transitions in life are very hard, and transitions in companies are very hard. The reality is, there's a certain number of years when you're productive to a company, and even if you're doing a good job, you reach a certain comfort level, and sometimes it makes sense to bring in some fresh blood. Lucy: I think that's right, if for no other reason that your network's been tapped out, or something else, that other people can bring in new thinking. So, this gets us into our next question. I think this notion that transitions are hard is really insightful. What other things would you tell a young person or anybody about entrepreneurship, and what kinds of advice would give them? Ellen: I think there's two things I would tell someone. The first is a practical thing, which is, do something you love, and do it with people you love or like, and all good things will come from that. I can't tell you the number of people who turn down great opportunities because their friends told them it was a bad idea, or it didn't fit in the sort of boxes that they had been taught in business school about how to evaluate an idea, or someone told them the business is going to be bad. So, you've got to, a lot of times, go with your instincts, and go with the businesses that make sense to you, and that you doing it, and with people you like, and then I would bet the percentages are in your favor. The second idea I would have for someone is a little less practical, but more of a gut instinct thing, and that is, don't worry so much. I think if you work hard, and you get a little bit lucky, and your timing is good, you will find good opportunities. If I had known how much fun I would have had doing different things, I wouldn't have worried so much along the way.

Larry: Wow.

Lucy: Is there a Yiddish word for, "Don't worry so much?"

Ellen: No, I don't know that one, but I'll have to call my dad.

Lucy: I think it could lead to a new company name.

Ellen: I always think of, hakuna matata, right?

Lucy: Yes, that's right. Exactly. But, I think you're right.

Ellen: It's not Yiddish, but it should be.

Larry: You got it. Lucy: It probably should be.

Larry: Well, I've got to ask another question here that pertains to everything we've talked about so far, but we're now looking at you. What are some personal characteristics that make you a successful entrepreneur?

Ellen: I think it's relentlessness, right? I think anybody's who's willing to face in the Internet world zero wages, zero revenue, you know, and a blank sheet of paper, I think yes, you have to have a certain passion, and relentlessness, and drive, and be internally focused, that you don't need someone every day telling you, "This is a great idea. You're going to do great." You've got to just have it from within and be laser-focused on executing.

Lucy: I'm just writing this down. I mean, I think the laser focus is exactly right, and the relentlessness, you know, we've heard before, as well. Some people have said even, "stubborn," or... Ellen: I don't know that I would necessarily always write stubborn, because there's a fine line between being crazy and being brilliant.

Lucy: That's true.

Ellen: Most of the people will tell you that their original idea was not always their final idea, so you need to have a balance of having great conviction in what your doing, but being flexible with what the environment is telling you.

Lucy: So, you had a very successful career starting companies, and obviously when you start a company, I'm sure you put everything into it, and give it your all, and people often want to know, well, how then do you balance that with a personal life, if, in fact, balance really exists?

Ellen: Oh, I believe in balance. I think you set limits. I think that working smart is a lot better than working every hour of every day. I think being efficient matters. I've seen people take so much time to do something, where that could be done a lot quicker, and I sometimes think when you have more things to do, you're more focused about the things you have to get done. In terms of balance, you just have to. Nobody goes to their grave saying, "I wish I would have worked harder."

Lucy: Absolutely.

Ellen: I have a great family. I run half-marathons. I have deadly, struggling golf game, and I think the Spectaculars are the most fun, coolest organization on earth. So, you've got to get out there and do other thing, and I think you have a better approach to work when you do.

Larry: That's some excellent advice. Gaining balance, or whatever that is, is one of the most difficult thing for new entrepreneurs, but they've got to somehow, as time goes along, really build that balance into their life.

Ellen: Oh, you're so right. And you've gone on with your life, so it's especially... I do know couples where one of them doesn't like to come home and talk about work or the other doesn't. We just incorporate it in our lives.

Lucy: There's an integration process there, I think.

Ellen: Yeah. But at the same point, there are points, you know, my husband... you know, sometimes people are amazed that they'll say something to Dave, and he'll say, "Well, I don't know about this, that's in Ellen's area." And they think that all we do 100 percent of the time is only talk our business stuff, and there are sometimes many days we don't even discuss anything "businessy."

Lucy: Well, that's so healthy, and also, you find things that way. Sometimes you find things when you just open up like that, that relate to the business that you never would have seen if you were just working all the time. So, that's very powerful. So, Ellen, you've achieved a lot, and we like to find out from the people we interview what's next for you. You obviously have a new company and so you'll probably be putting a lot of time into that, but anything else you'd like to share, either what's next for you, or what's next for Shmoop?

Ellen: Well, I think for Shmoop, I think we've done a really good job on lit., and history and poetry. We're going to do more in civics and get some of the math and sciences up there, because I think it's really important to be able to read, write, and do arithmetic. So, we've got to add the third stool.

Lucy: Well, we'd really like to talk about computing.

Ellen: Oh, wow, that would be great!

Lucy: Well, thank you so much. I just love your site.

Larry: I love your site, and I just want to say this one thing. Lucy referred to this, but she buried it a little bit. Right off of your Website, one headline there that really caught my attention said, "Shmoop wants to make you a better lover."

Lucy: Of literature.

Larry: Well, then, in parenths.

Lucy: Oh. Larry: "Of literature, history, poetry, and writing. I'm just getting in the complete line."

Lucy: Oh, OK. Ellen: Well, you know, if you just become a better lover, that'd be OK, too, but we'd like you to like lit., history, and poetry.

Larry: Oh, a fellow cheese head for sure. Thank you so much, Ellen, for joining us today.

Ellen: My pleasure. Thank you for having me.

Larry: And by the way, you listeners out there, make sure you pass this interview on to others that you know would be interested, and they can find the entire thing, and download it at any time at, as well as Thank you for joining us.

Lucy: Thank you. Transcription by CastingWords