Have you heard the one about the guy who walks into his boss’ office to quit his job and walks out with a new business, capital, an office and a board member? Probably not. But this is the story. It happened to me 26 years ago. It seemed surreal at the time and feels even more so now. And it’s all thanks to a world-class mentor who serves as a powerful reminder that mentorship is the intangible force behind most business and entrepreneurial success.
The story starts in the fall of 1998 – my senior year at Duke University. I was one of a handful of student leaders (as a class president) invited to attend a capital campaign fundraising dinner for million-dollar-plus donors. As fate had it, I was seated next to Howard Anderson – then the founder and CEO of The Yankee Group, a technology market research firm (now part of 451 Research). We struck up a conversation over dinner, and he asked me what I was thinking about doing after graduation. When I told him I just had an on-campus interview with IBM, he quipped that “friends don’t let friends work for IBM!” As the night concluded and he got up from the table, he handed me his business card and said “you should come work for me.”
I had never heard of The Yankee Group (though it was enjoying a 3-year run on the INC 500 Fastest Growing Companies list). And had never thought about Boston as a destination for where I wanted to go. But my gut told me something about this guy Howard made sense. I emailed him the next morning. We set a time to meet on campus a few weeks later; he specifically asked for 7AM on a Saturday morning. I’ve always been an early bird, so that wasn’t an issue for me. But I know it was one of his tests for evaluating a college student; were they willing to meet at 7AM on a weekend?
It was sort of a job interview. A really fast one. It concluded with him offering me a job. No details whatsoever about pay or even much about a job description – other than it was a sales position. Nonetheless, we shook on it right there on the spot. That happened to be Parent’s Weekend at Duke and my mom and dad were in town. When I came back to my apartment, my dad asked me how the interview went and I said “I took it.” You can’t imagine the incredulous look on his face when I told him this. In one of his past lives, he had been a college recruiter for Firestone – and was looking forward to guiding me through the job interview process. Instead, I was pretty much one and done.
I started working at The Yankee Group in the summer of 1999 after I graduated. I was there with the keen sense that – although I was truly an entry-level sales guy – I was also personally recruited by the CEO. And I felt an enormous obligation to work my butt off and be successful. But in the backdrop of all this was a lingering idea I had during my college days. And after a mere six months into my job at The Yankee Group, I felt both a mission-driven calling and an entrepreneurial urge to start a company. It wasn’t part of the plan. I’m not sure I ever really had a plan. But I decided I had to go pursue it.
I was truly distraught over the idea of telling Howard that I was going to leave my job – the one he personally recruited me for – just half a year into it. I felt an enormous amount of guilt that I was going to be letting him down or be disrespectful to our ‘handshake pact.’ So, it was with this heaviness and nervousness that I walked into his office one morning and asked if he had a few minutes to talk.
I sat down and nervously choked out words that went something like “I’m so grateful for this opportunity, but there’s just something I need to go do.” I briefly explained what I was thinking. And then there was the long, awkward pause. Just as I thought my worst fear would come true – that he’d be hugely disappointed or angry – he enthusiastically erupts with “Good! Great! Go do it!!” I was stunned and didn’t really know what to say. I started to go for the door and as I stood up he said “you’re going to need funding and a good board and an office…I’ll give you $30,000 and be on your board and I have an office for you across the river.”
I walked in to quit my job that day and walked out with a new company, funding, a board member and an office. All built on a handshake and a verbal promise. It sounds preposterous.
Howard remained on my board for the next decade until the company was acquired. He has been a mentor ever since. He’s had a legendary career on many fronts, not only as the founder of The Yankee Group and YankeeTek Ventures but also one of the largest venture firms in the country, Battery Ventures. In addition to investing in and nurturing hundreds of entrepreneurs, he has also spent decades teaching at various universities, including Dartmouth’s Tuck school, MIT Sloan, Brown University and Florida Atlantic. I’ve guest lectured for his classes every year.
Between his former venture investees, employees and students, there are now hundreds – maybe a thousand? – of us who have benefited from Howard’s super mentorship. Although Howard certainly invested financial capital, his greatest contribution has always been his investment of human capital – his own time and wisdom. This world could use as many Howards as it can get. Entrepreneurship, start-ups, business success in general – it’s all powered by super mentors and others who believe in us.
I’m now part of Howard’s pay-it-forward legacy. I’d bet good money that most readers reflecting on their success and fortunes will recognize they are part of someone’s pay-it-forward legacy too. There are many ways to think about patriotic duties to our country in the year of our 250th birthday of the United States. When it comes to driving the economy, investing in talent and spurring entrepreneurship – there’s nothing more important than to mentor.