The Hidden Power in Being Insecure
I wrote my first ever blog post about 4 months ago and was really surprised by the response that I got. Titled “The Future of the Home”, it was an introductory post to what was to become a more regular series of discussions around the area that I spend the majority of my time focusing on. It was released as a means of cutting my teeth on using such a platform to engage with my community. In the end, it was ready by more than 15,000 people and spawned at least one article from a credible publication where it was cited. Maybe that’s not uber-influencer status but it felt good.
Since then, I have been debating and curating the next topics to discuss. I have been studying the future of housing for the last four years and have written several posts that will dig deeper into this area over the coming months. In addition, I will be co-hosting events with Silicon Valley Bank throughout the year to further engage the Bay Area with our insights and our rolodex of incumbents and entrepreneurs who are seeking to change how homes are built, bought, maintained and lived in for the coming decades. I hope that this series will create a better collaboration between Silicon Valley and the ecosystem that surrounds the world’s largest asset class.
However, the best laid plans of mice and men often go awry. As I was set to release the next in the series on housing, I read an article that inspired me to diverge for a moment. Titled “We Don’t Talk Enough About Money in Silicon Valley. No, Really.”, Hunter Walk from Homebrew opened up about a topic that always seems relevant to the Valley but feels taboo to discuss. From the opening line where Walk talks about making someone uncomfortable by disclosing that he is a millionaire to an upfront discussion about how much his family gives back and the struggle to raise “normal” kids in a world of privilege, I found myself identifying with so many of the points and questions being raised. And there within the beauty and simplicity of the post, it struck me that there is an opportunity to provoke engaging dialogue around sensitive topics if done correctly. That led me here.
We’re All Great; Just Ask Us!
Silicon Valley has a special way of ensuring that one is constantly aware of the deficiencies in your life’s achievements. Some days it feels like everyone I speak to has at least one PhD from Stanford which they got after attending Harvard Business School which they did at the same time they were earning a double masters in engineering from MIT. Everyone has started and sold multiple businesses and has nine figure net worth which was obtained after being employee number 9 at Facebook. Their parents are doctors and their siblings have all written the great American novel. They see the future and speak about abstract concepts in ways that keep your head spinning. They have the confidence (sometimes arrogance) of someone who was destined for greatness.
This really shouldn’t come as a surprise when you think about it. The innovation economy thrives on confidence: the confidence to challenge a previously-held belief about the world, the confidence to ask total strangers for millions of dollars to back an idea with a 5% chance of success, and the confidence to invest in people and ideas and thoroughly believe that you will produce positive economic outcomes. It all requires a level of confidence that can overcome the stark realities of what is likely to ensue. If you are going to take on a long and arduous suicide mission, do you want someone who barely made it out of basic training whose best quality is ability to jump on a live grenade or do you want to call in the special forces?
However, in a microcosm of society where every day you are comparing yourself to the next person is it really possible that everyone believes they are as great as their pitch deck says they are? Is everyone buying what they are selling or is it just the ultimate defense mechanism? Does half the Valley go home at night and wallow in self-doubt or do they practice their best Stuart Smalley and repeat over and over that they are good enough, smart enough and doggone it, people like them?
So, Who is Who?
So if we take self-promotion as a necessary survival mechanism in the Valley, the question becomes how do you sift through all of it? As an investor that focuses on early-stage companies, this is one of the most important tasks that we do. A great team is the foundation of every great investment and underwriting that team across a multitude of dimensions is essential to success. But so is a great cap table and advisory board. And so I have created a mental framework for how I size up each of those potential contributors to help me better underwrite human risk.
Placing people in a two by two matrix is a bit rudimentary and certainly doesn’t perfectly analyze the complexities of human depth. But it can be helpful directionally. In my matrix, one axis represents talent (both perceived and actual) and the other axis represents self-promotion. In doing so, I end up with four segments of people that I label as No Names (Low Talent, Low Self-Promotion), Ambassadors (High Talent, Low Self-Promotion), Write Offs (Low Talent, High Self-Promotion) and Catalysts (High Talent, High Self-Promotion).
· No Names: I won’t spend much time here. The truth is I call low talent, low self-promotion quadrant individuals No Names because it isn’t worth it to name the category. Not because they aren’t human or worthy of my time, but because I NEVER meet them. Someone who lacks talent and isn’t willing to promote themselves of their idea doesn’t exactly end up in front of a VC.
· Ambassadors: These are the people that you wish you could just surround yourself with. They are highly accomplished and talented yet are down-to-earth, coachable and put others before themselves. They are rare, but when you meet them you instantly want to be part of their network. I call them Ambassadors because they embody everything you want Silicon Valley to be and make you want to move here just to be around people like them. More often than not, they have had considerable success in the past and no longer need to play the game but generally love being a part of the ecosystem and giving back. You want as many of these people in your rolodex or portfolio as humanly possible, but it’s hard.
· Write-Offs: The scariest group. These people are masters at pitching and self-promotion. They have studied how to play the game, know all the jargon du jour, and often have several signs of potential talent. But when the rubber hits the road, it just isn’t there. They don’t have true vision or true leadership or exceptional technical capabilities. They can raise a round or two of capital before the well runs dry. The moniker of Write-Offs is earned because they are the part of the portfolio that goes to zero.
· Catalysts: The most common person in the Valley is a Catalyst; a truly talented person who is not afraid to tell you. They’ve got moxie and charisma and the traits to back it all up. They are often the key to making your portfolio because their talent enables them to succeed at taking audacious chances and their self-promotion enables them to convince others (investors, employees, customers) to go along for the ride. They produce the outlier events.
As you can see from the matrix, self-promotion isn’t considered a negative. It is often an essential part of producing outlier events. But there are two key ways in which self-promotion must be analyzed and managed. First is understanding when self-promotion is baseless. Minimizing the number of times you are fooled by and invest in a Write-Off is a key to being a great human talent underwriter and imperative to producing great investment outcomes. Second is helping founders where self-promotion is rooted in real talent to harness that when needed and check it at the door when best served in doing so. Catalysts by nature are going to be in a constant mode of self-promotion to secure investors, motivate employees or LPs to power through tough periods, and even convincing themselves that everything will be alright. But helping a Catalyst become an Ambassador (at a very minimum among their trusted advisors) can have profound impacts. It allows them moments of vulnerability and opens them up to external counseling and perspectives that can be useful as the company grows.
Insecurity Can Be a Powerful Motivator
Self-promotion and insecurity are not mutually exclusive traits. In fact, I’d be surprised if they aren’t highly correlated. So in a world where it is ideal to portray and external image of power and confidence, how do we breakthrough the bravado to understand when that is masking a deep level of insecurity? And further, if we can breakthrough and discover this, how do we better enable the people we meet to deal with insecurity in constructive ways and realize that they are not alone?
Let’s start with the man in the mirror. In many ways, I have felt inadequate for a long time. My father left when I was five (good bye feelings of self-worth), I have never been a star athlete (unless you count darts or bowling, which of course I do) due to my lack of physical prowess, I’m not wealthy by many standards (although blessed financially compared to most), and I am not Ivy League educated. I am the first to graduate from college in my family which boasts no doctors, lawyers, engineers, entrepreneurs or academics. I’ve always been smart, but never guided to use that to its extreme. I’ve spent a great deal of my life devoted to being a good (and present) father which can often be at odds with substantial professional achievement. While I can’t complain about my lot in life, on the surface I am not exceptional by many standards.
Every time I meet with a founder, I have this anxiety that I am going to be revealed as a phony (this may be surprising to those who know me). A mere state school educated, poor boy from Florida with a blue-collar family tree. But much like the fear of failure has driven professional athletes, I utilize this anxiety to power me. It’s drives me to read books and study ideas. It drives me to hone other skills such as emotional intelligence, written and spoken communication, and genuine salesmanship. I do my homework on the likely topics of a meeting and I work voraciously to increase my likelihood of success through hustle, networking, keeping my word and giving at least 2–3x more than I get.
I have to believe that I am not alone in Silicon Valley. There must be a large group of people who go to work every day and think to themselves “I don’t belong here.” Who work so hard to personify their perception of what Silicon Valley is all about but deep down think that the rug will get pulled out from under them at any moment. Who constantly seek to find an edge that levels their playing field because someday their lack of a Stanford degree or experience at Google is going to be revealed. And then the jig is up.
Let’s Be Vulnerable Together
I love the Bay Area despite the feelings that it invokes in me. Ironically, it’s this paranoia and feeling of inadequacy that drives me. My infatuation with my time in the Valley and SF is 100% correlated to this dynamic. In a world that continually embraces and rewards mediocrity, you can’t survive in the Bay Area with indifference to bettering yourself. And, in so many ways, I wouldn’t want it to be anything else.
Self-promotion and confidence are necessary components of Silicon Valley That said, I truly believe there are opportunities to embrace a more open and vulnerable culture without destroying its fabric. For all the accepting nature that SV projects around racial and gender equality, for all its intolerance of social injustice, and for all the altruism of working towards solving the world’s great problems I have to believe that there exists an opportunity to re-imagine what is strong and what is weak. So those who identify with these feelings, I hope you feel empowered to be vulnerable. Or at least, feel good that you are not alone.