Success: 30 Interviews with Entrepreneurs & Executives

Introduction

Success is a subjective term. For some, success means having a big house, fancy cars, and a large bank account. For others, success means freedom: the freedom to do what you want, when you want. Everyone has their own definition of the word, which stems from our tastes, feelings, and life experiences.

A couple of years ago, I conducted an experiment. I wanted to know what some of the world’s most successful people, in my eyes, thought of the word success. I wanted to know what success means to them and the principles they live by. So I hustled, reaching out to hundreds of people, facing many rejections, to conduct insightful interviews.

In this book, you will read 30 interviews I’ve conducted with successful entrepreneurs and executives nationwide. For each interview, I asked everyone the same eight questions. These questions were meant to grasp their take on the word and uncover their life principles. These interviews changed my definition of the word success, as well as my entire focus on what my life’s work should be about. I was truly inspired by what I gathered, and I hope you’ll be inspired, too.

Colin Day

Colin Day founded iCIMS in 1999 and is the company’s president and CEO. Prior to founding iCIMS, Colin worked in sales and new business development at Comrise Technology, an IT staffing firm. After successfully opening a new branch office in Washington, D.C., Colin recognized an opportunity to carve a technical platform out of the company, and iCIMS was born.

In addition to his responsibilities at iCIMS, Colin works to develop Software as a Service (SaaS) industry awareness and to educate human resources professionals on how to evaluate recruiting technology. He has contributed to various publications, including Human Resource Executive, Employment Marketplace, and Human Capital. He has also spoken at various engagements, including ReedLogic’s HR Software Leadership Conference.

Colin has received numerous recognitions and awards. He has twice received Human Capital magazine’s HR Future Leaders Award, and has twice been rated one of the top five forward-thinking innovators in Fast Company magazine’s Fast 50 Readers’ Challenge. In 2007, Colin was named Ernst & Young’s Entrepreneur of the Year in the information technology software category. In 2008, Colin was recognized as one of the state’s most dynamic business leaders in NJBIZ’s Forty Under 40 award program. In 2009, he was a finalist in the Green Executive of the Year category of the NJBIZ Green Leadership Awards, and in 2011, he was named a finalist in the Executive of the Year category of the NJBIZ Business of the Year Awards.

1. How do you define success?

Stay true to yourself. It’s one thing to get to where you want to be, quite another not to take shortcuts/lose your soul/bend your morals along the way. Our world is too focused on short-term growth. It’s what the analysts/markets applaud right now. It doesn’t necessarily build something enduring for the customer, and isn’t that why we all got into business? You’ve got to wake up and be proud of what you’ve built, and the barometer for success should be beyond money and growth.

2. What is the key to success?

Surround yourself with people who are smarter, more experienced, and more capable than you are, and then figure out how to get them all aligned around a common mission, vision, value system, and culture.

3. Did you always know you would be successful?

Not at all. I knew I always wanted to work for myself, but I didn’t always know I’d be successful. I still wonder if I am, and I constantly try to redefine success each year.

4. When faced with adversity, what pushes you to keep moving forward?

I’ve always had an extreme fear of failure. When I was young, I used to avoid certain things if I didn’t know how to do them or have the confidence that I can do them better than others. I’ve brought that fear to the business world, and I am trying to make sure it’s a healthy fear.

5. What is the greatest lesson you’ve ever learned?

Be yourself, and don’t be afraid to go in opposite directions. When our competitors started dropping prices, we raised them. When they started building out a broad portfolio, we stayed focused and went deep. When they got starstruck by enterprise customers, we remained focused on the small and medium-sized business (SMB) marketplace. Blue ocean strategy allowed us to stand out and win at what we do best.

6. What do you enjoy doing in your spare time?

Sleeping. I have two kids.

7. What makes a great leader?

I am still trying to figure this out. I think it’s an ability to persuade people who are smarter and more capable than you to follow you, and then get the hell out of their way.

8. What advice would you give to college students about entering the workforce?

Don’t try to chart it all out. Life is random. I graduated with a psychology degree and joined a recruiting firm out of college because it was close to where my girlfriend lived. They built software that we took and spun out. That led to my company, iCIMS, where we now support over 1,500 companies. I never thought following a girlfriend would be the catalyst. Be open to any catalyst, but know an opportunity when you see one.

Craig Newmark

Stephanie Canciello, unali artists

Craig Newmark is a self-described nerd, pioneer of the web, speaker, philanthropist, and a strong advocate of the use of technology for the public good. He is the founder of craigslist.org, which he started in