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The Keith Krach Interview:

The Benefits of Fear and Humor, and What He Learned From the Worst Year of His Life

 

Known for the enormously successful tech companies he’s built and the high-performance teams he’s led, Keith Krach is at the top of many business leaders’ most respected list.

 

Currently, he’s the chairman of DocuSign and served as CEO for six years. Previously, he co-founded and led Ariba, one of the first business-to-business software companies. In less than three years it went public, and was later bought by SAP for $4.3 billion.

 

In this inspiring and unguarded interview, you’ll get a behind-the-scenes look at the times Keith has been tested personally and professionally, and how his values and reactions to fear are what led him to his success.

“In business, it’s all about building trusted relationships. Since you don’t have a lot of time, a key skill is how fast can you build trusted relationships in a short amount of time? Can you do it in one meeting? One of the best ways is to be vulnerable right out of the gate because then someone else does it and the next thing you know it’s not just a mind sync, it’s a heart, soul and gut sync.”

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Notable Revelations in the Interview

 

“I learned a lot about leadership in college through my fraternity. I was president, and it was like heading up a big family. It taught me a great set of values I’ll never forget. That was combined with the time when I was 19 years old I was a foreman of a chassis line in a General Motors plant. The two biggest issues I had to deal with were drugs and prostitutes. My mission was to get rid of it, and we did. The next Summer I was in the General Motor’s New York Treasurer’s office, and I got to see the very bottom and the very top. All those moments were scary, but they allowed me to understand it wasn’t life or death.”

 

“During those times when I had jumped in over my head in a business situation, I told myself that other people are there to help me and I needed to ask for their help. I always figured people know your weaknesses anyway, or they soon will. So you might as well admit it and have fun with it.”

 

“When I was 30 I came out to Silicon Valley and everyone thought I was nuts to leave General Motors behind. I was the #2 person at a software company, and it was like I got whacked in the face by a 2x4. The CEO I was working for had a different set of values than I had. The second day on the job the CEO said, ‘We have a board meeting in a few days, Keith, I need you to say this.’ And I said, ‘I won’t do that, I’d be lying.’ It was the worst year of my life, because on the one hand I had never really quit anything without finishing the job and on the other hand I wasn’t living my values.”

 

“The most valuable lesson I’ve learned in my career was about values. I had grown up in Ohio where there was always a great set of values and a lot of respect for people. It was this close to my face, and yet I didn’t see it. Not until I worked for a company that didn’t share those values.”

 

“If you’re making decent money in a job but working for a company that has a toxic culture or you don’t respect the leadership, you need to quit.”

 

“When Ariba went public on the stock market, the event was really about our family and team. Most bankers and CEOs head to New York, but we stayed local so that we could celebrate with all the employees. What was fun was that I brought my two oldest children. My oldest son asked me, ‘Are we rich?’ And I said, ‘You bet Steve. You are as rich as you have family and friends.’ And you could see the lights go on in his head. Although he did ask me how many shares I had and I told him it was none of his business.”

“Taking a few years off of being a CEO to raise my kids was the greatest thing I’ve ever done. I got the chance to visit my daughter at Princeton, coach baseball, sleep in the room with my youngest soon, cook for their friends...it was just great.”

 

“The biggest setback I’ve faced in my personal life was losing my dad. He had lung cancer and died in my arms. We did everything together -- he was my mentor and best friend. He radiated wisdom. When he passed, I had to be tough and not show emotion as CEO of Ariba. But then I had a delayed reaction two years later: I missed my dad and it hit me like a ton of bricks.”

 

“When you’re stuck in a corner, being pounded, and you think you’re gonna die, my dad said the way out of it is to ‘mock yourself out.’ Use humor. The best defense is a strong offense. It works every time.”

 

“In business, it’s all about building trusted relationships. Since you don’t have a lot of time, a key skill is how fast can you build trusted relationships in a short amount of time? Can you do it in one meeting? One of the best ways is to be vulnerable right out of the gate. The magic of that is then someone else does it and the next thing you know it’s not just a mind sync, it’s a heart, soul and gut sync.”

 

“When in pursuit of the almighty dollar, don’t compromise your integrity or moral compass. People can take a lot of things away from you -- they can say they don’t like how you look or that you’re not smart, but they can’t take away your integrity. At the end of the day, that’s everything.”

 

“My biggest desire now is to inspire the next generation of leaders and entrepreneurs along their journey.”

“When you’re stuck in a corner, being pounded, and you think you’re gonna die, my dad said the way out of it is to ‘mock yourself out.’ Use humor. The best defense is a strong offense. It works every time.”

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“In business, it’s all about building trusted relationships. Since you don’t have a lot of time, a key skill is how fast can you build trusted relationships in a short amount of time? Can you do it in one meeting? One of the best ways is to be vulnerable right out of the gate because then someone else does it and the next thing you know it’s not just a mind sync, it’s a heart, soul and gut sync.”

“When you’re stuck in a corner, being pounded, and you think you’re gonna die, my dad said the way out of it is to ‘mock yourself out.’ Use humor. The best defense is a strong offense. It works every time.”

The Keith Krach Interview:

The Benefits of Fear and Humor, and What He Learned From the Worst Year of His Life

 

Known for the enormously successful tech companies he’s built and the high-performance teams he’s led, Keith Krach is at the top of many business leaders’ most respected list.

 

Currently, he’s the chairman of DocuSign and served as CEO for six years. Previously, he co-founded and led Ariba, one of the first business-to-business software companies. In less than three years it went public, and was later bought by SAP for $4.3 billion.

 

In this inspiring and unguarded interview, you’ll get a behind-the-scenes look at the times Keith has been tested personally and professionally, and how his values and reactions to fear are what led him to his success.

“In business, it’s all about building trusted relationships. Since you don’t have a lot of time, a key skill is how fast can you build trusted relationships in a short amount of time? Can you do it in one meeting? One of the best ways is to be vulnerable right out of the gate because then someone else does it and the next thing you know it’s not just a mind sync, it’s a heart, soul and gut sync.”

Notable Revelations in the Interview

 

“I learned a lot about leadership in college through my fraternity. I was president, and it was like heading up a big family. It taught me a great set of values I’ll never forget. That was combined with the time when I was 19 years old I was a foreman of a chassis line in a General Motors plant. The two biggest issues I had to deal with were drugs and prostitutes. My mission was to get rid of it, and we did. The next Summer I was in the General Motor’s New York Treasurer’s office, and I got to see the very bottom and the very top. All those moments were scary, but they allowed me to understand it wasn’t life or death.”

 

“During those times when I had jumped in over my head in a business situation, I told myself that other people are there to help me and I needed to ask for their help. I always figured people know your weaknesses anyway, or they soon will. So you might as well admit it and have fun with it.”

 

“When I was 30 I came out to Silicon Valley and everyone thought I was nuts to leave General Motors behind. I was the #2 person at a software company, and it was like I got whacked in the face by a 2x4. The CEO I was working for had a different set of values than I had. The second day on the job the CEO said, ‘We have a board meeting in a few days, Keith, I need you to say this.’ And I said, ‘I won’t do that, I’d be lying.’ It was the worst year of my life, because on the one hand I had never really quit anything without finishing the job and on the other hand I wasn’t living my values.”

 

“The most valuable lesson I’ve learned in my career was about values. I had grown up in Ohio where there was always a great set of values and a lot of respect for people. It was this close to my face, and yet I didn’t see it. Not until I worked for a company that didn’t share those values.”

 

“If you’re making decent money in a job but working for a company that has a toxic culture or you don’t respect the leadership, you need to quit.”

 

“When Ariba went public on the stock market, the event was really about our family and team. Most bankers and CEOs head to New York, but we stayed local so that we could celebrate with all the employees. What was fun was that I brought my two oldest children. My oldest son asked me, ‘Are we rich?’ And I said, ‘You bet Steve. You are as rich as you have family and friends.’ And you could see the lights go on in his head. Although he did ask me how many shares I had and I told him it was none of his business.”

 

“Taking a few years off of being a CEO to raise my kids was the greatest thing I’ve ever done. I got the chance to visit my daughter at Princeton, coach baseball, sleep in the room with my youngest soon, cook for their friends...it was just great.”

 

“The biggest setback I’ve faced in my personal life was losing my dad. He had lung cancer and died in my arms. We did everything together -- he was my mentor and best friend. He radiated wisdom. When he passed, I had to be tough and not show emotion as CEO of Ariba. But then I had a delayed reaction two years later: I missed my dad and it hit me like a ton of bricks.”

 

“When you’re stuck in a corner, being pounded, and you think you’re gonna die, my dad said the way out of it is to ‘mock yourself out.’ Use humor. The best defense is a strong offense. It works every time.”

 

“In business, it’s all about building trusted relationships. Since you don’t have a lot of time, a key skill is how fast can you build trusted relationships in a short amount of time? Can you do it in one meeting? One of the best ways is to be vulnerable right out of the gate. The magic of that is then someone else does it and the next thing you know it’s not just a mind sync, it’s a heart, soul and gut sync.”

 

“When in pursuit of the almighty dollar, don’t compromise your integrity or moral compass. People can take a lot of things away from you -- they can say they don’t like how you look or that you’re not smart, but they can’t take away your integrity. At the end of the day, that’s everything.”

 

“My biggest desire now is to inspire the next generation of leaders and entrepreneurs along their journey.”

“When you’re stuck in a corner, being pounded, and you think you’re gonna die, my dad said the way out of it is to ‘mock yourself out.’ Use humor. The best defense is a strong offense. It works every time.”

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