If my childhood was a wild vine meandering where life took me, my high school was the trellis of rigid structure that allowed me to climb and grow. Brother Rice is a very serious, all male catholic school outside of Detroit. The strict rules and iron discipline never bothered me – instead it was structure and I let my vine climb around it and grow to new heights of academic and athletic achievement. Brother Rice was a modern day Sparta with a strong dose of enlightened Athens mixed in. I put on 20 pounds of muscle each year. I developed a strong grounding in STEM as well as History, English and Theology. The signature moment for me came just before Christmas of my senior year when Harvard’s athletic department called me and asked if I would like to play football for The Crimson. It was a storybook ending to a wonderful childhood. 

Four years at Harvard was a massive growing experience for me. In many ways, I was woefully ignorant and lacking in perspective when I arrived. It did not take long for my friends and colleagues to shine light on the misconceptions and naïve ideals. I learned as much at the dining table as I did in the classroom or athletic field. Like a whetstone, Harvard ground away my rough edges and sharpened my critical thinking skills. For nine months of ever year I experience the lofty heights of Ivy League education. I also met a series of incredible people. Ironically, one day during my sophomore year, I stumbled out of the science center after pulling an all night coding session. I ran into my computer science teaching assistant and she said “Aren’t you going to hear Larry Ellison speak?”

“Who is Larry Ellison?” I asked in a No Doze induced voice.

“C’mon, find out for yourself,” she said. 

I trudged back into the science center, only to be amazed. Larry Ellison was full of fire and brimstone. He railed for 45 minutes about his idea that the “Network was the computer” and outlined the ideas that would become SaaS. I was impressed and inspired.  

If the school year was filled with lofty ideas and worldly personalities, my summers were the opposite. I interned with my uncle in heavy duty manufacturing. In my favorite summer, I had to interview each machine operator and uncover systemic problems. (The kind of problems that everyone had stopped questioning and just accepted.) Once I found such a problem, it was my job to propose revolutionary innovations that would reinvent the processes. I was in over my head, but I learned to swim. My interviewees were an intimidating lot – burly bikers loaded with tattoos, men who had grown up tough and did not take kindly to an Ivy league kid asking a bunch of questions. I had to learn how to build real rapport and establish trust and credibility. I took a lot of ribbing, but I forged friendships once I started really getting to know them. One operator worked all night and ran a fish store by day. Another used his mechanical skills to buy old cars and restore them to immaculate condition. I found that my preconceived judgements were flawed. It was a fantastic education in understanding people and it pulled the weed of Ivy League arrogance from my soul before it ever took hold. 

When I left Harvard, I joined a strategy consulting firm in Palo Alto, CA. R.B Webber & Company was an elite Silicon Valley name. The firm prided itself on only hiring from Harvard, MIT, Stanford and Yale. I joined the firm in 1998 – the height of the dot.com boom. It was a heady and exciting time to be in tech and Silicon Valley was the undisputed heavy-weight champion of technology. It was clear to me that I was the last picked recruit, but I used that knowledge to work even harder. The job did not pay well when compared to the cost of living in Silicon Valley. I lived in a closet, yes an honest-to-goodness closet, for $500 a month. My roommates were guys attending Stanford Business School. I learned as much from them as I did from the job. I spent a lot of my time going to the library to pick up books on strategy that they recommended. I spent most of my weekends in the office reading. In three years I built a reputation as a dogged researcher, financial modeler and interviewer. Using the same skills I developed interviewing machine operators, I got to know my clients and their customers. At the end of the third year, one of my clients invited me to join their company. I left R.B. Webber having met some of the finest minds I have ever known.

My next stop was Appareon, a software company that wanted to build the next generation of supply chain technology for the Apparel industry. The company was years ahead of its time. The vision was superior. We had the best backing you could imagine. We were well funded, but alas, we were not funded enough for such an ambitious undertaking. By January of 2001 the “dot com nuclear winter” had settled in. Funding had dried up. When we ran out of capital, we put the company on ice and scattered to the four winds. Despite the failure, it was an incredible experience for me. I had been the right hand man for the CEO – crafting the pricing plan, market plan, forging business alliances, working with our early customers and participating in our capital raising. It was another amazing chance to learn. 

With no one hiring, February of 2001 was a daunting situation. I decided it was time to start my own company. I wanted to start a software company of my own, but without any funding available, I had to rely on my own resources. Then the phone rang – one of my industry contacts asked if I would consult for them. It rang again two more times. By February 6th of 2001, I had incorporated San Francisco Consulting Group, Inc. with three paying clients. 

My first challenge of leadership came in those first 7 months of San Francisco Consulting Group. I was alone. I was unsure if I was “for real”. I could not decide if what I was doing was “temporary” or the real thing. Indecision plagued me. I was lonely. On September 10th, 2001, I decided I would make this a real business. I took out my first loan. I hired employee number one, a very talented consultant I had known previously. The next day was 9/11. That was a day of real decision for me. Should I fold, layoff my first employee and join the CIA or make SFCG a real business? I thought about it for a week. Ultimately I concluded that the patriotic way to fight terrorism was to do what I do best, preserve and build my company. I made my decision and did not look back. 

By 2004 I had four employees, a profitable business and got married. There is a wonderful personal story of how I met my wife, which I will summarize: I was at a San Francisco Chamber of Commerce lead swapping meeting. A colleague of mine who owned a catering company asked if I would take the elevator down to the street and pick up a food delivery for him. While waiting for the food to arrive, I struck up a conversation with an enchanting girl. She was waiting as well. I gave her my card before I left. Our first date was four days later. In two weeks we knew we were soul mates, even if everyone else thought we were crazy. We dated for 14 months before getting engaged to “prove” to our friends and family what we already knew. Our wedding is one of the happiest memories of my life. It was the start of something amazing that has lasted to this day. 

In 2005 I discovered Siebel’s “CRM On Demand”, which was an alternative to Salesforce.com. I never liked Salesforce.com – they were extremely arrogant, even for Silicon Valley, and they treated me poorly as a customer and a possible partner. If they were not going to respect me, I would not do business with them. I decided to partner with Siebel. On Friday, September 9th, 2005 I got the partnership paperwork from my counterpart at Siebel. He said “I can’t tell you why, but I can only tell you that if you do not sign this paperwork today, it will be revoked on Monday.” I knew what that meant. I signed the paperwork. On Monday Oracle announced they had acquired Siebel. I was now an Oracle partner. I recalled my college encounter with Larry Ellison. “Well, this ought to be fun!” I thought.