01 Jun 2011
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Mr. Start-Up

Mike Cassidy (MBA ’91) has launched and sold four tech companies since graduating from HBS. Now, at Google, he’s having even greater impact.
by Deborah Blagg

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Issue Focus: Entrepreneurship

As a second-year MBA student, Mike Cassidy asked if he could stray from an assignment to write market assessments and instead create a start-up business plan. “The professor was Walt Salmon, and fortunately he was all for it,” recalls Cassidy, who eventually made good on the plan to launch Stylus Innovation, a computer telephony software firm, with $1,500 he and two MIT friends scraped together from personal funds and a $10,000 prize for winning MIT’s business plan contest. In 1996, the youthful trio sold the company to Artisoft for $13 million.

Prior to HBS, Cassidy had earned two degrees in aerospace engineering from MIT and considered becoming an astronaut. After selling Stylus, he briefly indulged a long-held passion by studying jazz piano, before settling into a spectacularly successful career as an entrepreneur, building and selling three tech companies — Direct Hit, Xfire, and Ruba. In spring 2010, when Google bought Ruba, Cassidy’s online travel guide business, he joined the Internet search giant as director of product management. He was the driving force behind the February 2011 launch of Social Search, which incorporates content shared or created on social media sites into Google search results.

With four successful technology start-ups on your résumé, you’re now on the payroll of a big company. Has your entrepreneurial mindset changed since you started working at Google?

I’m having a blast at Google. It’s amazingly fast-paced. It’s been the most intense, frenetic nine months of my life, and that includes launching my own companies. The difference is that my mindset here is project-based rather than focused on building a start-up.

As accomplishments go, how would you compare launching your first product at Google to a product launch at one of your previous companies?

When you build a company from nothing and create a product that has 15 million users or reaches a market value of $100 million or $500 million, that’s a great feeling. At Google, the scale of your impact is much bigger. The first day we launched Social Search, we reached a billion people! That’s pretty cool.

At this stage in your business career, is reaching lots of people a primary motivation?

I want to build products that people love. I’m a capitalist at heart: I believe entrepreneurs who create useful products or services are contributing something of benefit to society. Working in Silicon Valley, where so many companies are developing ideas to make people’s lives more fun or more productive, is an amazing opportunity.

The other thing that’s important to me is to interact with people in a way that will earn their respect and make them want to do business with me — as investors, partners, or customers — again and again. I like to think my success is helping others to become successful.

You didn’t have a lot of previous experience in the niches where you’ve launched start-ups. How did you know your concepts would fly?

The short answer is, we didn’t know. Three out of the four times I’ve started companies, our original idea was not very good; we had to change direction significantly. But I believe in getting into the game, getting into an industry, even if your concept isn’t perfect. Then, as you figure out that your idea may be flawed, you’re also learning what’s missing in the industry and what people are looking for. In the start-ups I’ve launched, that knowledge helped us, eventually, to build a very successful product.

Do you think that iterative approach is best suited to high-tech start-ups, or would it be as valid in another sector?

If you believe in rapid iteration, starting with a simple concept, quickly getting customer feedback, and just being good at executing, then it could work in a variety of fields. But my hunch is our dramatic user growth and financial successes happened partly because we were in a highly leveraged environment.

In Direct Hit, the company we launched and sold a year and a half later for $500 million, our software product was built by three people. If it’s software, or high tech, or the Internet, then it doesn’t matter whether 10 people use it, or 10 million, or 100 million: It’s the same amount of work to build the first product.

You emphasize speed in product development and execution. Is that approach contrary to the conventional wisdom that you build businesses by building relationships?

Absolutely not. I have over 5,000 contacts in my database. One of the reasons I’ve been able to succeed is that I have an amazing network of talented people to call, who can help me solve a problem within a day, or an hour, that might otherwise take a month.

There are studies that look for consistent traits in entrepreneurs: Are they a firstborn child? Were their parents entrepreneurs? Did they move a lot when they were young? I think one pretty consistent finding has been that successful entrepreneurs do a great job of building relationships.

Your approach to business is pretty intense. Are you a tough boss to work for?

I try to be super supportive. I find co-workers who share my love for work, and my energy and drive. After that, I just try to remove the bottlenecks so we can all work together as a team.

Sometimes I get calls from CEOs who are nine months or a year into running a new company, and they want advice about how to motivate employees who don’t share their level of commitment and sense of urgency. I tell them they’re asking the wrong question at the wrong time. You’ve got to hire people who are just driven right from the start. You don’t want to have to push them; they should push themselves. That’s the key.

How do you find people with that kind of drive?

First of all, I love working with people I’ve worked with before. Most of the first dozen people at each start-up were people I already knew. Before hiring anyone new, I make sure someone I know and respect can vouch for them by saying something like, “This person is amazing.” Or I’ll find people I know from a different context. Two of my best colleagues were intense athletes. I played Ultimate Frisbee with one, and I could tell by the way he played he’d be a terrific person to do a company with. The other was a woman who almost made the Canadian Olympic marathon team. People who are intense about sports often bring that same trait to the workplace.

How do you maintain personal balance with such a demanding work life?

I bike or run to work most days. It helps me to step back and see things in a different way. I’m home at 6:30 on weekdays to have dinner and generally don’t go into the office on weekends, with very few exceptions.

You experienced great financial success at an early age. What impact has that had on your lifestyle?

Nothing I’ve done after selling my first company has had much of an impact on my lifestyle. That gave me enough money to buy the kind of house I wanted and set aside enough for my kids’ college tuitions. I’m not really into material goods. My friends roll their eyes at me, but my only car is a 2000 Nissan Maxima. I guess I’m most excited about money as a way to save time, which is much more valuable to me.

What was the most important thing you learned about entrepreneurship while you were a student at HBS?

One really critical thing it gave me is the ability to communicate in a compact, compelling, and concise way. When you’re in a class with super-smart MBAs, and you have maybe 45 seconds to air your point of view, that’s a unique exercise in concentrated analysis and charisma. It’s fantastic practice for everything you do in a start-up, from raising money and recruiting employees to closing business development deals.

Do you have any advice for would-be entrepreneurs?

We live in a time and place where there are amazing opportunities for business ventures. Whether you’re just starting your career or you’re ten or fifteen years down the road and looking to change direction, don’t hesitate to jump in. I’m a huge fan of starting your own company, because I think it lets you get closer to life. Your destiny is in your own hands. If it’s Sunday night and you’re not excited about going to work on Monday, being an entrepreneur may be the cure for that.

— Deborah Blagg

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Class of MBA 1991, Section G
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