As I was approaching my 30th birthday, I reached one of those career crossroads that would change everything for me. I had to choose between “safe and successful” or a major leap into the unknown. Ten years earlier, my experience with a challenging internship at GM (read “Running Scared On GM’s Cadillac Assembly Line”) had taught me some of the benefits of “jumping into water over my head.” But now, I was in for an even bigger challenge.
At 29, I had already achieved a surprising level of success, given where I started.
My dad and I were both thrilled when I won a scholarship from General Motors to get my engineering degree at Purdue University. We were both amazed again when GM granted me a Fellowship to study at Harvard Business School. My dad started referring to the company as “Generous Motors.”
After school, I went to work for GM, and soon became the youngest VP in the company’s history. All pretty exciting for a simple Midwesterner like me.
I could have stayed at the corporation and done very well. But after 10 years of security with “mother GM,” I wanted leave the nest to build something of my own. Silicon Valley was becoming a mecca for innovation, and I just knew I had to see what I could accomplish there.
My dad had hoped I would come home and help him expand his machine shop business, but he knew I had bigger dreams than that, and he gave me his blessing. But when I let folks at GM know my plans, they all thought I was crazy.
As it turned out, my leap to Silicon Valley had me in way over my head—I just didn’t know it. I joined an early-stage enterprise software startup as COO. On the second day of the job, the company founder and CEO said, “We are having a board meeting next week and I want you to say this…” And she asked me to misrepresent our performance to our board. Things sure didn’t work this way back in Ohio, or even in Detroit at GM. It was the beginning of a nightmare.
I told her I absolutely would not, “That would be lying.” At that moment, it was crystal clear that the CEO and I didn’t share the same values. It was the toughest time of my life. I tried everything I could think of to “reform” the company’s culture, but eventually I realized I just couldn’t live with the values of the company leadership.
After months of struggle, things finally came to a head, culminating in what would be another jump into very deep water for me. I was actually at the hospital for the birth of my first son. The company founder kept calling me, demanding that I come in to the office for a meeting with our biggest investor, IBM. I made it clear that my team was completely prepared, and could handle the meeting for me, and I was not going to miss the birth of my baby boy. When she wouldn’t accept it, I finally told her to do something that was anatomically impossible and finished with, “I quit.”
I thought I’d had a great opportunity in Silicon Valley, but now it was gone. I knew I couldn’t sacrifice my integrity to stay at that company. And my pride would never let me go back to GM. The only thing to do was to jump into water over my head again—into the unknown. I quit without having a backup plan. With young kids. Now that’s scary. But it turned out to be a great decision—actually the most pivotal decision of my life.
I was desperate and in a hurry. But I swore to myself that I wouldn’t make the mistake of joining, building or starting a company that didn’t have an uncompromising set of strong values.
Maybe the scariest thing of all was to go looking for a job after a “failure.” I had never had to hunt for a job before. GM scooped me up during my sophomore year at Purdue, and then the executive recruiter for the Silicon Valley startup made that opportunity look so enticing that I never bothered to look at other alternatives. (Never made that mistake again either.) Nevertheless, I was on a mission now.
So, not having any real job hunting experience, I decided to put my Harvard Business School training to the test and created “The Keith Krach Strategic Business Plan—Built for Success.”
It was a complete business strategy for “Me, Myself, and I,” my new temporary business enterprise. I applied many of the traditional concepts like the 6P’s—product, positioning, pricing, packaging, promotion and place—to myself. I also operalizationized the tactics with form letters, templates, configurable resumes, distribution lists of recruiters, friends, Purdue, Harvard and Sigma Chi alumni. You name it. It was all in a big fat notebook that I still pull out to show my children when their time to job-hunt approaches.
I struck gold when I wrote a letter (no email in those days) to an HBS alumni whom I had never met or heard of before, a guy named Chuck Chan. He introduced me to a tiny start-up named Rasna, a design engineering software company. I wound up joining the founding team, as COO.
We were soon recognized as number 3 on Inc Magazine’s list of the 100 fastest growing companies. Eventually, Rasna was purchased by Parametric Technologies for $500 million. Later on, I would recruit some of the old Rasna team to help me found what would become one of the most successful software startups in history, Ariba.
Since those early days of making the leap to come to Silicon Valley, and then leaving the startup I had joined, I’ve had many more opportunities to face my fears and jump into water over my head. Starting Ariba, leading the Purdue University Board of Trustees, and joining the fantastic team at DocuSign have all been exciting adventures. Each one has involved leaving what’s familiar and safe, and jumping into water where I can’t see or touch bottom. And each adventure has been a thrill. Transformational.
I am now addicted to the adrenal rush of jumping into water over my head. I call it “scary fun.” Don’t get me wrong—every now and then I still end up under the desk in the fetal position. But I realize……the key to personal growth and making an impact is facing your fears and jumping into water over your head. Sometimes, it’s the only way to learn how to swim. Try it. Who knows, you might get addicted to the deep end too.
Check out the video below for more examples of jumping into water over your head, starting with my undergrad experiences with Sigma Chi at Purdue.