Always a Teacher at Heart: Positioning to Follow Your Passion
Thomas Darden, Charter Class
When you sit alone and take time to reflect on where you see yourself in 5, 10, or 20 years, what images come to mind? Do you see yourself in the same field doing the same things? If you see yourself considering a possible change, how do you position yourself to make that change? Even if you are totally fulfilled by what you are doing today, how do you best position yourself to be ready to make a transition in case you change your mind in 20 years? This is exactly where I was 20-25 years ago.
When I commuted on the train to my job as an executive for the School District of Philadelphia, I had plenty of time to reflect on my career journey. Most mornings, as I passed through inner-city Newark, NJ and thought about my own inner-city upbringing, I was often amazed at the path I'd taken into the world of public education. While it's taken me more than three decades to finally become directly involved with education, in truth, it's probably where I always wanted and needed to be.During my 35-year career I've lived in 12 different cities and worked in three major industries for companies that ranged from one of the largest in the world to early-stage startups. I've helped start two companies, founded a venture capital and private equity firm, and successfully changed my career path three times—from engineer/manager to investor and now into public education.My journey has been more amazing and satisfying than I could have imagined, because I consciously sought out change and a manageable level of risk in my career decisions rather than the consistency, comfort, and security that is probably more the norm. I sought situations where I didn't have all the answers, so I would be stretched enough to grow, and the lessons I learned from willingly seeking out risk helped me develop the confidence to make tough decisions and career transitions.Many who view starting your own venture capital firm as a crowning career achievement have asked me with great interest why I made a transition into public education. Some who might be thinking more about following their own calling or simply finding a meaningful way to give back, have asked me howI made this transition.In this article, I address these two very important questions, first providing some perspective on my career and the lessons about risk and ambiguity that I learned along the way. Hopefully, you will find these lessons helpful in learning how to: (1) map yourself and your options in relationship to your passion, (2) navigate your own journey, and (3) prepare yourself to be both comfortable and well-positioned to make important career and life decisions.
A Career Lived Consciously on the Edge
When I was in high school in the early 1970s, I really enjoyed helping others learn and thought seriously about becoming a teacher. I had several coaches who were also my teachers, and their dedication, on and off the field, helped me grow both as a person and as a student. Their example of using sports and education resonated with me, and I could easily see myself following in their footsteps.
However, I entered high school at a time when this country was aggressively recruiting people to become engineers; as I happened to be good at and really enjoyed math and science, I ended up pursuing a career in engineering instead. From that beginning, I soon fell into the world of venture-backed startup companies in the early days of Boston's Route 128 technology boom. After 11 years in startups, I jumped into venture capital investing as a member of the Charter Class of Kauffman Fellows, and I eventually started my own venture capital and private equity firm. Each time I transitioned, I made a conscious choice to try something new, to accept and manage risk and to deal with the ambiguity that came along with each transition.
The First Big Lesson: 1977–1984
I started my career in the late 1970s in the auto industry with General Motors, where I was responsible for providing design engineering support to a $750 million product line—people looked to me every day to make million-dollar decisions. I quickly learned that people didn't care if I was half their age, as long as I could quickly figure out their problem, develop and present a solution, back it up, implement it, and move on to their next problem (there was always another problem in high volume manufacturing). I learned much from my GM experience about how to be a disciplined and effective engineer, and a little about what it took to run a large organization by watching our leadership team make tough decisions.
When I decided to leave the comfort of a large company located in my hometown and seek out a new opportunity, everyone in my family thought my wife and I were crazy (she was also an engineer). They couldn't understand how we could trade the "sure thing" for the uncertainty of moving a thousand miles away to a place where we didn't know anyone or have prospects of stable work.In retrospect, the decision to move was actually very easy because we were seeking a better education for our son who had lost his hearing from meningitis. He was attending a state-run school for the deaf, and the educational expectations of the institution were, to put it mildly, substandard—even for the nineteenth century, and he was going to be living in the twenty-first century. We immediately began to make the mental transition by first buying boxes to pack up our belongings and then looking for jobs; by committing to the move and the change in this way, we were subconsciously accepting that things would be ambiguous.Rather than "do what's right and live with the consequences"—the real, and simple, lesson is that randomness and uncertainty always accompany any major change and are by-products of what are usually manageable risks. In learning to be comfortable that you can "manage the risks" and handle the ambiguity (without "freaking out"), you have to ask and answer a deceptively straightforward question: "What's the worst that could happen?" In the case of our son's education, our final assessment of the cost of NOT providing the best education possible for our son clearly outweighed any potential risks of our decision to move.In most career and life decisions, there is no way to know whether you are truly doing the right thing. When the balance of pros versus cons is unclear, subconsciously, the ambiguity can often be paralyzing, causing us to just "stick with what we know" rather than commit to the change that accompanies any big decision. When faced with lack of clarity around a decision, I've found success with the approach of simply committing to the decision to make the change. I always found that when I fully committed mentally to the change, I was better able to cope with whatever happened, and I was often surprised at my own creativity in dealing with the various issues that arose.
From Engineer to Startup Junkie: 1984–1995
I had no idea where our move would lead my career and was extremely fortunate that the best school we could find for our son was located near Boston's Route 128 area. Because of the skills I had gained at GM, I landed in my first startup, GTECH Corporation which pioneered the online lottery business. The company happened to be looking for engineers that had experience with both design and manufacturing, and I was the only engineer they interviewed who could work between both groups to quickly solve problems that exist at the intersection of the two.
Having come from the auto industry—where no one made a move unless the decision had been vetted for at least two years—I initially found it somewhat difficult to adapt to an environment where there were no systems or procedures and things were changing on a sometimes daily basis. I learned to remain calm and make and implement the best decisions in this high pressure, unstructured, startup environment using the lesson from our move: ambiguity always accompanies change.No one in authority knew how to truly manufacture in high volume, and I was able to utilize my seven years of experience in a large manufacturing company to help the team learn how to modify both our design and manufacturing processes and efficiently scale up for high quality manufacturing. We had our issues, but we were ultimately able to demonstrate success: We experienced tremendous growth, and four years after our launch had an IPO that generated a significant return to the seed investors.A year after we went public, I found myself becoming bored with managing day-to-day operations in my department. Fortuitously, I was invited to join another startup by a CEO sitting at the table next to my team at our favorite lunch spot. He overheard me "lecturing" my team on how to address some challenges we were having with a new product. This CEO was running Surgilase, Inc., an early-stage medical laser company right across the parking lot from GTECH, and he was waiting for me outside the next day at lunchtime. He told me that my skill set was just what he was looking for and asked if he could give me a detailed pitch.After work that night, I stopped by and learned more about the team, the company, its product, and its investors. Surgilase had many of the same early-stage dynamics as GTECH, but I had learned a lot during my GTECH experience. I could clearly see the path to quickly solve their problems, and I was also intrigued and excited by a new opportunity—the next day, I decided to join Surgilase.Within a month, I was on board and again neck-deep in the spine-tingling startup world. We were bringing a new medical device to market in the late 1980s, and we were selling a high-end piece of capital equipment into a healthcare market experiencing its first bout of cost and funding pressures. Our product experienced great initial success, but our sales fell off as the healthcare crisis expanded. Our investors informed us they would no longer fund us, and for two years we fought to stave off bankruptcy.During this period, my wife had transitioned out of engineering and was in law school full time; our children were 6 and 10 years old and in private school, and I was basically both Mr. Mom and an executive in an unstable startup. My wife never knew that our startup was on the verge of bankruptcy for most of that time, and to this day she is happy I never told her. (I decided not to tell her because I was comfortable that I could manage the risks and I didn't want her career derailed by unnecessary worry.)Out of necessity, I learned how the entrepreneurial drive to survive and succeed compels the challenge of long accepted approaches to managing and leading. In order to re-conceive how to bring new products to market and overcome the bureaucracy of the FDA, we had to develop practical new approaches to product development and marketing. We helped Surgilase survive by bringing out six new products and gaining FDA approval for all six in less than nine months. We learned how to manage cash flow (i.e., how to manage our "float") and how to make critical decisions in as close to real-time as is probably possible (and prudent).One of the big takeaways from my second startup experience was that if you can learn to live with constraints out of necessity, it's even easier (and more profitable and efficient) to live this way when times are good. In the process of managing the constraints, you essentially learn to compartmentalize the variables in ways that engender confidence along the way—which also helps with managing ambiguity and risk.We eventually sold Surgilase and made a 2x return for our investors. After that tough and pressure-filled four-year experience, I was happy to move on to my third startup. In 1991, I was the seventh employee of UltraCision, another medical device manufacturer. Our goal was to bring to market an ultrasonically activated device called the Harmonic Scalpel that cut and coagulated at the same time, effectively allowing for bloodless surgery.Our CEO was the most aggressive executive I had ever seen. He was always pushing us to think about growing the company faster than we thought humanly possible using what I came to call "mini-plans," in which he would break up our 5-year plan into quarterly goals or focus areas for the company. One quarter we'd be a product-development company, the next quarter a cost-improvement company, the following quarter a manufacturing company, and then a sales and marketing company.Over the course of four years we overcame significant challenges. For example, in developing our technology we were operating on the cutting edge of the established theories of ultrasound technology, and at one point the product stopped working. After trying everything, we finally decided to throw out the established theories and actually think from scratch (i.e., I finally learned what it really means to be an engineer). We went from running at a loss to achieving 65 percent gross margins by instituting a "designed experiments" approach to our product development and manufacturing, and we came to be seen as a revolutionary company in the then-emerging surgical field of laparoscopy.To be absolutely fair and forthcoming, we had an especially talented team in my third startup; I was challenged to be better than I ever thought I could be, which was often more than humbling. With every challenge we faced, each member of our team was forced to think hard about how we could contribute to addressing our problems, and we each discovered and added our unique strengths in the development of solutions.In terms of making big decisions, my UltraCision experience taught me that if you can remain calm in tough, pressure-filled, situations there is always a solution—provided you have a strong team that is well-led and mutually committed to success. In addition, the "mini-plan" approach our CEO used at UltraCision was an effective strategy for helping our team stay focused on the challenges we faced—one step at a time.
The Venture Capitalist: 1995–2008
As we were selling UltraCision, I was finishing up an MBA at Babson College. Two of my professors, Jeff Timmons and Bill Bygrave, had been working with the Kauffman Foundation to create the academic components of the Kauffman Fellows Program. Both encouraged me to apply, and I joined the Charter Class of Fellows in 1995 and served my Fellowship with Advent International in their Boston office.
Pursuing Success Full Steam Ahead
When I entered the Fellowship, I initially thought I'd spend two years working on an idea for a business I had developed while also learning more about how to raise money to fund my plan. Little did I know that the managing, leading, and coaching skills I'd built over the prior 17 years would be useful as an investor—I was intrigued enough that I decided to stick with it for a few years after my fellowship to find out whether I could be a good investor. The risk was manageable, as at worst I'd start my own business or gravitate to another startup in the Route 128 area.
Over the course of my 13 years in venture capital, I became a reasonably good investor and learned several lessons along the way. In any business there is a desire to know your customer, but in working aggressively to generate returns for limited partners, it is easy for venture capitalists to get the business equation turned upside down (especially during periods when returns are hard to come by). The equation that worked for me is one that I think all venture capitalists know, but sometimes find difficult to hold onto: serve entrepreneurs first and the returns will follow.As venture investors, it's easy to stray from serving entrepreneurs first. LPs demand our attention, and raising the next fund can become the main thing; when our priorities are confused, management fees can easily be viewed as wealth creation rather than wealth transfer. If we truly want to build wealth alongside the entrepreneurs we back, then paraphrasing George W. Merck of Merck Pharmaceutical, I believe as venture capitalists, ''We must always remember that we invest to partner with and support outstanding entrepreneurs and to build great companies…if we remember that the entrepreneurs we back are the key, wealth creation will never fail to appear. The better we remember that our entrepreneurs are the key, the larger the wealth creation will be."1
Finding Balance and Discovering Purpose
We started Reliant in mid-2000, just prior to the internet bubble bursting, so we were forced to maintain a laser-like focus in order to survive that tumultuous time in the VC industry. In fact, for the first four years, I did almost nothing else—when I finally looked up, I found that I was missing the balance that everyone needs in their life.
In 2005, I made a decision to regain that balance, and I naturally gravitated back to my involvement in education-related activities. I had always been involved in some capacity with education, from setting up and running tutoring programs in high school and college to founding a nonprofit called Science is Fun with my wife in 1987. (My wife still works with this nonprofit that gives 3rd-8th graders a fun-filled introduction to science and technology with the goal of helping them build a lifelong comfort level with the world of science.)Throughout my career, I had always found time "outside my day job" to sit on the boards of various schools and education-related organizations, and I've also served on two governor's commissions that studied urban and state educational issues. While I never became a teacher, education made a difference in my life, and throughout my career I have tried to do my small part in helping others have the same educational opportunities. It was only natural that I look for ways to pursue something I was passionate and knowledgeable about, and where I could make a difference.I began looking around Chicago to find worthy educational causes. In 2006, I joined the board of the Chicago Public Education Fund and the board of trustees of National-Louis University (one of the first colleges of education in the country). These two boards were doing important work in urban education, and they got me intimately involved with key issues facing the Chicago Public Schools (CPS). I got a chance to interact at a strategic level with Arne Duncan, CPS's then-CEO and our current Secretary of Education in the Obama Administration. I also began mentoring CPS principals and meeting regularly with the CPS Chief Academic Officer.I could have stayed in the background and continued to serve on education-related boards, giving my time and money to this cause. However, not only was education my passion, but I had stayed involved and abreast of developments in the field, so I was well positioned to fulfill my passion—under such circumstances, a transition can almost seem natural.
The Educator: 2009–Present
Our schools are still structured to serve an industrial age that no longer exists. Because of my entrepreneurial and venture capital background, I knew I had developed a valuable capacity to help others manage change and ambiguity—a skill I could use to support educators in overcoming their apprehension about making the very tough, but necessary, changes required to significantly improve education in this country. Once I came to this realization, I could no longer sit on the sidelines of this crisis.
Similar to my transition into venture capital via the Kauffman Fellows Program, I found The Broad Superintendents Academy (TBA), an education-related fellowship sponsored by another billionaire philanthropist, Eli Broad. TBA is a 10-month "boot camp" that helps executives, former military leaders, and education professionals learn to apply their leadership experience in addressing the challenges facing large urban school districts.2 I went through the TBA fellowship in 2009, and simultaneously started working with the School District of Philadelphia.
The "Why" and the "How": Positioning Myself for Transition
If you had asked me in the mid-1980s what I'd be doing with my life when I turned 50, I would have been sure I would be running my own company or doing something related to entrepreneurship. Once I was in my first startup, I was hooked—I loved being an engineer and entrepreneur, worked long hours in each startup, and found the excitement addictive. When I transitioned to venture capital, I liked it a little less but still found tremendous enjoyment and satisfaction in interacting with and coaching entrepreneurs.
As my former partner in Reliant often said, "No one wakes up in the morning saying they are ready for change." They may need one and even intuitively know how, but as human beings we are probably more wired for stability, so it's not natural for most of us to consciously seek change. Most people need a strong catalyst to even consider it, and for a major life change like a career shift the catalyst is often not of our own choosing.So "why" did I make the transition into public education? Why was I positioned to make this change, and what might it mean for you at this stage of your career? Three things convinced me.First, my wife had made several successful transitions over the course of her career, from professor to engineer to patent attorney, to starting her own law firm, to helping a firm build an intellectual property practice, and finally to becoming an actor. She started acting classes to help with her "stage presence" during her infrequent litigations, but realized that in acting she found a path to truth and honesty and a vehicle to more fully realize her passion to help others. Though she made a dramatic career change, she continued her string of successes, landing a semi-recurring role on As the World Turns after just a few years. My wife inspired me by demonstrating that if your true passion lies elsewhere, you don't have to continue with what you've been doing or what you've been trained to do. After watching her transition and seeing her find a way to realize her passion, I began to listen to my heart—I thought long and hard about how I wanted to spend the last third of my working career.Second, I asked myself a simple question: "Of the activities I'm engaged in, which ones give me the most enjoyment—where do I get my energy from?" I truly enjoyed working with the entrepreneurs but I was less enthused by the fundraising and the deal-closing process. I began to realize that I most enjoyed the energy I got from mentoring principals and helping them address issues and challenges in their schools.Third, I believe that if, as a nation, we do not significantly improve the education we provide to all our children, we will one day act surprised to discover we are no longer the country we think we are. Overall, U.S. public schools have made little or no progress in recent decades, and the quality of U.S. education has significantly worsened in many of our large urban areas. Lack of significant improvements in our urban public school districts will have dire consequences for large segments of our society and the cities in which they live. I also believe that perhaps no other country is as well positioned to play the role we could in helping to address some of our current and pending global problems, provided we have a well educated citizenry.In terms of "how" I made my transition, in hindsight it was primarily possible because I was well positioned. I was knowledgeable about the field I was committed to pursuing, and comfortable with the ambiguity and risk that accompanies major change.I had consciously stayed connected by always staying up-to-date on educational issues and serving on boards where I could simultaneously learn and give back in terms of both my time and money. I sought out progressively more influential education-related boards that I felt were making a real impact. Staying abreast of the issues also entailed reading Education Week (the Wall Street Journal of the education industry) every week for over twenty years and annually seeking out the best books on what was needed to improve public education and why (e.g., Horace's Compromise by Ted Sizer3). I had a good command of the issues, and some level of influence and a solid network (stemming from my non-profit board work).The other key was the lessons I learned during my experiences in the fast-paced and challenging world of entrepreneurship and venture capital. For all these reasons, I was able to find my way to the School District of Philadelphia to work directly with my passion, at last.
Following Your Heart
I often reflect on the thirty-odd years it took me to finally become directly involved with education. I now fully recognize the importance of being well positioned and comfortable enough to take on the challenge of pursuing my passion—not everyone is fortunate enough to be in that position.
I am privileged to be able to do something that I absolutely love doing every day, and my wish is that everyone be prepared and able pursue their passion. We are all deeply passionate about something, and there are no limits on what our futures hold. If you can learn to be comfortable with the ambiguity accompanying the changes required to follow your passion, and you find ways throughout your career to stay connected to what you are passionate about, you will be well positioned and on your way to following your heart and pursuing your passion full time.
Thomas Darden
Thomas E. Darden, Jr. most recently served as Deputy Chief for Innovation and Partnership Schools for The School District of Philadelphia, the ninth largest school system in the country. Previously, Darden served as Managing Director of Reliant Equity Investors, a firm he co-founded in September 2000. Prior to Reliant, Darden was a Managing Director at Wind Point Partners, and he has 17 years of experience in a range of management roles at both startups and Fortune 100 companies. In addition, Darden was a member of the Charter Class of Kauffman Fellows. He holds a bachelor's degree in engineering from the General Motors Institute, a master's degree in business administration from Babson College, and he is a graduate of the 2009 class of The Broad Superintendents Academy.
1 George Wilhelm Merck, address to the Medical College of Virginia, Richmond (1 Dec 1950), quoted in James C. Collins and Jerry I. Porras, Built to Last (1994, 1997), 48.2 "The Broad Superintendents Academy," n.d..3 Theodore R. Sizer, Horace's Compromise: The Dilemma of the American High School (New York: Mariner Books, 1984).
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