Ellen Siminoff: “Learn How to Sell”

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Ellen Siminoff, CEO of Shmoop

Ellen Siminoff is an entrepreneur, executive and advisor in Silicon Valley. Currently chief executive of Shmoop, an online educational resource for kids, Siminoff was one of the first executives at Yahoo, where she served as senior vice president of entertainment and small business. She was also chief executive of Efficient Frontier, a search engine marketing solutions firm sold to Adobe. She is on the board of directors for Mozilla, Zynga, and SolarWinds. She received her MBA in 1993 from Stanford GSB.

In 10 words or fewer, what is the big idea behind your business?

Return joy to learning and teaching.

What is the best advice you’ve ever received?

Go West. When I was studying at Princeton a number of people told me to apply to Stanford. I didn’t even know I was interested in technology or would become an entrepreneur. Apparently, some people knew me better than I know myself!

What was the most difficult lesson you have learned on the job?

Embrace turnover. A lot of people are fearful and worry when people leave their companies. People are relevant to companies at different phases. They select out when they are no longer believers. You want to get those people out as aggressively as you can. At every company I have ever been involved with, there has been a panic when someone important resigned. In almost every case, a month later, the company finds someone else and moves on.

What advice would you give other entrepreneurs on how to build a great business?

Learn how to sell. I have never seen entrepreneurs do poorly when they are good salespeople. In Silicon Valley we are great at building great technology and better mousetraps but at the end of the day, a company needs revenue. You need to learn how to reach customers and get them to buy. There is a perception that marketing is good and sales is somehow of a different order. But when times are tough the first thing a company cuts is marketing. You never get rid of good salespeople. And good salespeople often become CEOs.

What inspires you — how do you come up with your best ideas?

There are a couple of times in your life when education really matters to you: when you are going through it yourself and when you become a parent. My husband went online and became angry when he saw what was there in education. So much of what is online discourages students from learning and makes it more complicated. With Shmoop, my husband wanted to make learning fun and educational. He can explain Hamlet or calculus in a way that gets kids excited. Once we nailed the tone and the voice of the site, it almost wrote itself. The voice we landed on is a mixture of the way Dave talks with the voices of our favorite teachers. I had the world’s greatest algebra teacher. We took the material everyone else was teaching and made it live and breathe.

What is your greatest achievement?

I like to think I’m a good mom. My kids are 13 and 9. It’s a mix of listening and responding, as well as being clear with expectations and helping them with whatever they are doing.

What do you consider your biggest failure?

I was a dreadful organic chemistry student. It has not been helpful to me so far.

What values are important to you in business?

Honesty. I know that seems trite but what I mean is that you should do what you say you are going to do.

What impact would you like to have on the world?

I think my children will far exceed anything I have done. I would like to make a difference for one student who is slogging it out in school. Maybe it’s someone who was not planning to study for the SAT and now is motivated to do better in order to go to a better college. If we can change one kid’s life, that matters.

What was your first paying job?

My first real job was at Princeton. I sold advertisements for a magazine on campus called Business Today. It was founded by Steve Forbes at Princeton. We sold sponsorships to major companies and sold ads. I got commissions and I got paid. Instant gratification! I thought that was terrific. My parents paid my tuition, and I made enough doing sales to cover all my other expenses. I was really proud of that. I just “got” business. After sophomore year I flipped from pre-med to business.

What is the best business book you have read?

I’m reading a book called Java. I think I would have been a great programmer. My son, who’s nine, loves to code, and we read Java together. He also has a tutor, and we are taking online courses through Stanford and MIT.

What businessperson do you most admire?

My husband. I don’t know too many people who can be financially brilliant as well as creative. Most people are either creative or analytical. He can manage money at a sophisticated level and also write really brilliant and funny copy.

What is the most valuable thing you took away from your time at Stanford?

B263. Optimization Models. That class taught me how to optimize results when there are a bunch of things you cannot control. The main idea is that if you can’t control it or have an impact on it, then get it out of the equation. I also remember in an organizational behavior class I learned that the most powerful person in the company is the one who sits in the most central location because they have the benefit of communication. My favorite professor was Jack McDonald. He taught an investment class. He was supportive and a good mentor — one of those people who did more than teach. He was there to empower you to get beyond Stanford.

What do you think is the greatest innovation in the past decade?

I love my iPad. It has brought happiness to my life. I do email, play games, surf the internet, and read everything from The Wall Street Journal to Google News.