Portfolio July 26, 2011

The Entrepreneur Questionnaire: Sunny Gupta, Founder and CEO of Apptio


Barbie Hull Photography


Sunny Gupta is Founder and CEO of Apptio, a Greylock-backed start-up based in Bellevue, Wash., that helps enterprise CIOs manage the costs, quality and value of the IT products and services they provide. Notable customers include Cisco, Boeing, Northrop Grumman, Bank of America, Facebook and J.P. Morgan Chase.

Describe your business in 10 words or fewer.

Apptio provides the CIO a business management platform to run IT like a business.

What is the big idea behind your business?

Businesses have witnessed a major transformation in the way they use technology to automate functions such as manufacturing and sales. But most CIOs do not have an equivalent system to manage the business of technology. That is the opportunity we see for ourselves. Globally, organizations spend more then $4 trillion on technology each year. Technology has continued to become strategically important to corporations. There needs to be a paradigm shift that enables more transparency so that CIOs and other technology leaders can make decisions based on facts and not assumptions.

How did you come up with the idea for Apptio?

When I was at Opsware I was sitting in the office of the CIO of Goldman Sachs. We were talking about the acquisition of Opsware by HP and one of the people in the room asked me what I was going to do next. I started asking questions: What are you struggling with? What are your challenges? They described this exact problem. As soon as we got home my business partner and I started calling IT leaders in different types of industries to see if this really was as big of an idea as we thought. That’s when we realized everyone has this problem and no one was solving it.

Why are you excited about the future for this company?

We see a clear window of opportunity and have been able to attract some of the world’s largest companies to run their IT businesses on Apptio. We have the ability to define and build the next major enterprise software category. We also think there is a great opportunity to extend our footprint outside the realm of IT.

Why did you become an entrepreneur?

I was working at IBM as a developer when I started to feel that my career was only going to incrementally grow in corporate jobs. That wasn’t good enough. I wanted to take control of my own career and grow exponentially.

What was the most difficult lesson you have learned as an entrepreneur?

The most important lesson was that customer validation has strategic importance. The key is to continuously reinforce that culture so your team is always thinking about it. The most difficult lesson I’ve learned is personal. At a certain point in running your own business you realize that it is all about the team. You need the right people around you and sometimes you have to make emotionally challenging decisions. As an entrepreneur you start off with people you know and trust but some of those people are unable to help you get to the next level.

What has surprised you about being an entrepreneur?

Entrepreneurship is all consuming and requires a lot of focus. If you are in it for the money, don’t do it. The sacrifice required is unprecedented. You need to be sure you are doing this for the right reasons.

What five adjectives would you use to describe yourself?

Results-driven, competitive, passionate, focused, rational.

What values are important to you as an entrepreneur?

Being focused on results is extremely important. Focus on the areas where you need work rather than celebrating what you do really well.

Integrity and honesty. Rather than speak behind someone’s back I believe in giving direct feedback.

I encourage all our employees to make informed decisions rather than asking for consensus. This is the advantage that a start-up like Apptio has when going to battle with massive competitors.

Encourage fast failures—and be careful not to make the same mistake a second time.

What is the best business advice you’ve ever heard?

Customer validation trumps everything. I learned this at Mercury Interactive.

What is your motto?

In business you frequently are forced to make decisions that are on the borderline of integrity and ethics. The most important thing is to be on the right side.

Which living person do you most admire?

Steve Jobs. The whole world has benefitted from his personal style of innovation. I also greatly admire Jeff Bezos. He has shown a rare ability to continue to innovate from within a large corporation. Amazon started as a book company, then it became an etailer and a Web services company before introducing the Kindle.

What are you passionate about?

Building a next generation business and defining an entirely new business category. Creating wealth for the people around me. And football: I’m a big Seattle Seahawks fan. If I weren’t doing this I would be working in the football industry.

What motivates you?


What was your first paying job?

Washing dishes at a restaurant.

What do you like most about being an entrepreneur?

The ability to control your own destiny. I would always bet on myself.

What do you like least about being an entrepreneur?

The constant scrutiny.

If you could change one thing about yourself, what would it be?

I wish I could be more trusting. It comes down to skepticism and paranoia.

What do you consider your greatest achievement?

The greatest achievement is in front of us not behind us.

What is the last book you read?

The Lincoln Lawyer by Michael Connelly.

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

Of course it is important to find out what your customers want but it is more important to know what they will pay for. The only way to know if your customers really value something is if they are willing to pay money for it.

Never underestimate the power of the team around you. Bad teams can take a great market opportunity and turn it into a failure. Great teams can take a mediocre opportunity and turn it into a success.

“If you are in it for the money, don’t do it. The sacrifice required is unprecedented. You need to be sure you are doing this for the right reasons.”