Blog Post #11: On Owning Your Story, Well-Intended Advice and Why the Short Path Was the Long Road
When I started this newsletter / series of posts, I promised they would not be autobiographical in nature. Today, I realize, some stories are simply worth telling. It occurred to me weeks, maybe months, ago that my venture capital career could have started earlier, much earlier. As I’d mentioned in earlier posts, I became a full-time venture capital investor in February 2021 (during a global pandemic no less). What I haven’t shared is when I received my first venture interview…that was in 2014. Nearly seven years ago. What happened? You ask. The story is a simple one which I share below. But it’s important to note that when I think of it, I reflect mainly on class, well-intentioned but very poorly delivered advice, what it means to have “access” in this country and why traditional but certainly not one size fits all paths like investment banking and consulting are advertised to intelligent and ambitious incoming graduate students who are not only dream of but are fully capable of doing so much more.
When I arrived to Columbia Business School in the fall of 2014, I’d just resigned from the Economist (yes, that one), and turned down opportunities at several other large publications believing that if I wanted to “be something”, I needed to transform my experience into something that reflected a quantitative skill set I’d yet to demonstrate. Months before arriving to campus for my first class, I’d made a spreadsheet of bankers at several large firms and embarked on a proverbial path to wall street that seemed not only sound but highly accessible. All I had to do was meticulously follow the steps both alumna and wall street veterans had described to me over and over again in New York coffee shops as I listened, with wide eyes and sincere interest. With great discipline, and the echoes of my father’s voice, I quieted the voices in the back of my mind that reasoned venture capital and entrepreneurship would be far more interesting for me, in spite of the fact that at the time, New York City was seeing an emergence of both technology-enabled startups and venture capital firms that rivaled the Bay Area. But even with my quieting, my curiosity wouldn’t allow me to look away completely and soon enough, I tested the waters.
Just after orientation, I joined the Columbia Entrepreneurs Organization and sent my resume out for interviews at startups and venture capital firms just “to see” what hiring managers would think of me, someone who’d spent so little time in excel, a mentor (and Wharton alum) who’d written one of my recommendation letters gave me a 30-minute primer on what can now only be described as “creating a list in excel 101”. I wanted validation that I was making the right decision in recruiting for investment banking. I needed to know, with certainty, that the venture capital world would reject me and that considering it was a fruitless task. To my surprise, the interviews rolled in, from founders and start-up executives who loved the exposure I’d had to both social and digital media and the world’s largest media brands and venture capital firms who wanted access to what would hopefully be the next Facebook or Myspace examined through the lens of a young and hungry non-traditional MBA. Some of the calls and requests for interviews I took, preparing meticulously for each conversation in a desire to push the envelope, and myself, even further. Surely when they met me they would reject my uninspiring academic experience (Big 10) and assume that someone who hadn’t spent years in Excel and PowerPoint would be the wrong fit and I could recruit for investment banking in earnest. That wasn’t the case. I was wrong, very wrong. I received offers, several of them. As it turned out, I was exactly what many Silicon “Alley” (a nickname assigned to the technology ecosystem in New York City) firms were looking for. As a fellow CBS alum once described to me, “On a rack of 30 white shirts, the lone black one looks interesting”. I would learn, that my story, convoluted and windy, was fresh and interesting because it was different (and very “New York”) and therefore my perspective was as well. Less than one month after starting classes, I received my first venture capital interview at a firm investing only in digital and social media-based companies. Both managing partners wanted to meet with me and they prefaced the meeting by noting they were “excited” about my resume and that my experience was exactly what they were looking for in a candidate. Though some part of me wished for it, this wasn’t the outcome I’d expected. Unfortunately, with the opportunity to completely course correct, de-risk my career, and live my father’s wildest dreams looming in the back of my mind, I turned it down. I’d had a coffee chat with a prominent investment banker along with a company happy hour (an informal attempt for recruiters at top firms to recruit talent in a social setting) the same day. Today, I’m not sure why I didn’t reschedule though I’m sure there was some part of me that knew had I gotten the job, I would take it and abandon my pre-planned finance path, fulfilling my own dreams in the process but abandoning my parent’s. This story isn’t unique to me, and for both my own children and many generations of MBAs to come, I’m inspired to change it.
Higher education is the hallmark of America’s middle class. What is lost in wealth and prestige is made up for in accolades and an appropriate level of perceived belonging and acceptability (another defining characteristic of the middle class) is a natural consequence of joining exclusive clubs with access determined only by family educational history and / or personal IQ, extracurricular engagement or study habits. Great wealth would never be required to join, but a progressive future is all but be guaranteed. Year after year, MBA and other graduate programs churn out members of the “professional or managerial middle class” (described as making $135,000 and higher in income, adjusted for inflation, and having graduate degrees as a defining characteristic) who go on to create acceptable lives that they can later pass on to their children. Year after year, these institutions produce scores of talented graduates ridden with both debt and guilt resulting in subpar job performance and loss societal contribution. Political leaders would argue that the debt is by far the most crushing aspect of this phenomenon, I argue that the personal angst leading to a global epidemic of clinically described anxiety and the loss of outcomes associated with connecting great talent to even decent causes are miles and away worse. So far, the only thing I hate about venture capital, is that I didn’t…start…sooner.
The world does not need more inroads to wall street or consulting firms. The world needs academic programs that empower and encourage independent thought, programs whose success and rankings aren’t measured by the average income of the average graduate and how direct its pipeline is to well-known firms but by how well they successfully equip students with knowledge, tools and a frame work to succeed, and be well compensated, in fields they want to enter. Had I received and taken that opportunity in 2014, I could have closed 70 deals by the end of this year (assuming an average of just 10 every 12 months). While investment banking and equity research have no doubt done wonders for my career and financial progression, those 70 deals could have done much more. And it is with great assurance that I can say, though the choice would have been confusing to him then, my father would have been proud. With this in mind, I encourage well-meaning mentors, parents, friends and other advice givers to push back on the advice seeker, by posing the questions “Tell me first, what interests you? What do you want to do? Who do you want to become?”. If the answer to the last question is another person, I would follow up with this question, “Which decisions did that person make inspire you?”. The answers you’ll unravel will not only help you give better advice, they will help the ambitious young man or woman in question look deeply within themselves, examine who they are, and better prepare themselves to make decisions to pursue things worthy of both their time and their talent. There are many problems to be solved and even more solutions to be provided, and there are far more than two paths, or even five, to solve them. While professional services, medicine, law and engineering are fine paths, they too, should be chosen.
While, in its totality, I recall that first semester of business school with a great deal of pride, having proven to myself that anything is possible with a plan, I occasionally feel the sting of opportunities left unexplored. I am one of the luck ones though. Admittedly, I find myself fortunate that I have the opportunity to explore these things today and maintain a healthy support system that allows me to do so. Seven years later, I have my dream job and it is without question, those 70 deals along with many more will come. I advise no aspiring student however, to follow my path. My actual advice is simple: Do the thing that you want to do and get well compensated for it and when that is not possible, do what you have to do until you can. Your life will be so much more fulfilling. I offer this advice to individuals young and old, educated and not.
I close with this. One of life’s great ironies is that one of the greatest obsessions of the middle class is transcendence, but what I’ve observed is that the advice most often given results in a continuation of the status quo. The only way to break this cycle is to offer different advice, to embrace risk and ask smarter questions. At its core, well-intended advice is often an attempt to protect an individual from failure in the path not yet known, but my question is, how tragic would it be if this remarkable mind succeeded at the familiar one?
See you in blog post #12.
