How I Got Ahead by Being a Cocky Bastard
“It doesn’t matter if I burn my bridges behind me; I never retreat.” Fiorello LaGuardia
“We like to think of our champions and idols as superheroes who were born different from us. We don’t like to think of them as relatively ordinary people who made themselves extraordinary.” Carol Dweck
[Note for Medium: This is an excerpt from my forthcoming, How to Get Ahead When You Have Nothing to Offer, a collection focusing on what I’ve learned through helping build the careers of hundreds of young people and growing dozens of businesses over the last 5 years.
Previous chapter is titled “Be Humble.” This chapter is titled “Be Cocky.” This is the first 1/3–1/4th of Be Cocky.]
Wait, I thought the last chapter was “Be Humble.” What gives?
Be both. Be humble and cocky at the same time. It’s not the contradiction it sounds like.
The gist of “Be Humble” is to present yourself humbly and to not pass up opportunities that may have a high payoff in the end but appear to be below you at first. You’ve probably heard stories of people working in lowly jobs just to earn enough to spend on valuable books or to be near somebody influential. That’s the gist in “Be Humble.”
Be externally humble and internally cocky.
Present yourself with humility and don’t instantly view anything as beneath you but also be proud of yourself and overestimate your abilities. A cocky person can be described as somebody who thinks too highly of himself, right? If so, take the “objective” picture of your skill set and your abilities (if you’re reading this, probably either nothing or close to nothing) and throw it away. Instead, imagine yourself as somebody capable of learning anything, doing things few others can or will do, and able to push your professional and personal limits. Don’t announce this image to the world (better to have others underestimate you than overestimate you) but store it in your mind. This is the image of yourself at the core of “Be Cocky.”
“Be cocky” is not exactly popular advice. The image of the cocky person in one’s mind is somebody who thinks more highly of themselves than they should. But this kind of cockiness is a false sense of esteem better described as arrogance. Arrogance is viewing oneself better than others and entirely driven by the desire to see oneself brought up and raised above others in the eyes of the respective community. Cockiness doesn’t care about this comparative aspect. The only comparison you should make when being more cocky is between who you want to be and who you are today.
All too often I meet young people whose humility in getting opportunities is top-notch and they suffer no real difficulties in landing a gig but who then plateau or stagnate from their because they are afraid to be cocky. They don’t want to challenge and push themselves for fear that they have to prepare or study first or that they must put in long hours and climb a seniority ladder in order to get the promotion. Their fear is driving them to plateau in their pursuits rather than to flourish. Fear of cockiness extends from a deep-seated fear of not being enough and not measuring up to the expectations which we believe others hold of us.
Especially with high achievers, there’s a strategic leveling-down that a young person will do. The tallest poppy gets cut off, after all. Be too ambitious and too sure of yourself and you may push yourself further than ever before and try new challenges and learn new skills, but if you fail, many more will see your fall from grace than if you stayed conservative and didn’t push yourself too much beyond the pack. This was my own strategy for years. I would have big goals and ambitions but would never broadcast them to peers or to people who held some kind of power over me in their judgements (i.e., potential business partners, investors, employers, etc.). If I undertook huge, difficult projects and cast myself as the type of person to achieve them and I achieved them — great, I’ve done what I said I would do. But if I failed to achieve them, then I looked like a silly person who thought too much of himself.
That’s where Be Humble comes into play. Protect your downside by externally reaffirming that you are always learning and a novice at every new level of the game. But don’t let Be Humble poison your inner spirit. You can protect the downside and maximize your upside by projecting the humility of Aristotle while internalizing the self-assuredness of Jobs. The reality is that most people think of you much less than you think but that you can still protect the downside in your failures and pump the upside in your successes by projecting humility and pushing yourself beyond previous expectations.
Be Cocky is not about measuring yourself against others. It is an entirely individualistic act. The reality is that to achieve great things and to get ahead from being at having nothing to offer, you need to evolve and become a future, better version of yourself. You need to not merely endorse the idea that you can get better and become better, you have to know it and act on it. The cocky person knows they deserve better than they currently have and is not going to stop until they get it. The cocky person knows they can learn new skills under pressure. The cocky person knows they can increase their earning potential. The cocky person knows they can grow their business, even when they’re rolling at maximum bandwidth. The cocky person knows they can step up to the plate and take on new challenges.
The cocky person doesn’t win every challenge but doesn’t shrink away from them when they appear. They learn how to grow through challenges and adversity (see Be Antifragile for more on this…but you have to be willing to take on the challenge before anti-fragility can actually help you!).
The opposite of cockiness isn’t humility, it’s cowardice.
After working for a year on growing Praxis and getting it off the ground, we had case studies to show that our model of startup apprenticeships was working. We took people who had little more than ambition and time and accelerated their careers beyond their peers in a short nine months. We were ready to scale the model and decided the biggest chokepoint would be in bringing on new companies. It didn’t matter if we had thousands of hungry young people looking to take control of their careers if we didn’t have the companies to host them.
We put out a call for applicants for a Director of Business Development. This person would drive our growth by signing up new, interesting companies with whom our participants could apprentice. Somebody with years of experience in the startup world and a Rolodex of founders, investors, and advisors could plug us in practically overnight and grow the network.
At this time, I was still doing a little bit of everything. My days consisted of reviewing applicants, writing content for our blog and earned media, reviewing our curriculum to make sure it was free of bugs and typos, and doing as much recruiting as possible. The job was far from glamorous but provided me the opportunity to get an idea of just how many moving parts a new company required to operate.
I watched as the applicants for Director of Business Development came and went. Those who had the networks did not understand what we were doing. Those who understood what we were doing did not have the networks. Our existing business partner network was reaching capacity and we needed to get new businesses on board and fast. The job required a number of different prospecting and sales techniques — going through investors and advisors for introductions, cold calling and emailing businesses that were growing, pitching founders, HR people, and investors on taking a chance on a fresh, young employee in a company, and even putting out fires when things would go wrong and making sure both the business partner and the participant were happy. I didn’t really know how to do any of these things but they sounded interesting to me and I knew I could learn how to prospect, pitch, and extinguish if given enough reason and just not enough time. So I left our office, let the CEO know I would be back soon, and sat down for an hour and a half at a local cigar shop with a blank Pages document and a cup of coffee. On that document, I drafted up a three-year plan for identifying and partnering with some of the fastest growing companies in the country. I researched a number of tools for finding growing companies — the Inc. 5000 Fastest Growing Companies, AngelList, Crunchbase, and others — and thought of every way that I could approach them and pitch our partnership. Using a mix of cost-of-living and startup-growth-rate indicators, I selected a list of a half-dozen US cities on which to focus and start developing relationships and scheduling business trips immediately. I even drafted up a plan for international expansion in years 2–3.
In the executive summary of the proposal, I openly admitted that I was (considerably) less-experienced than most of the people with whom we had been speaking and that there would be a learning curve for me to scale in taking on this job (see: Be Humble), but I also admitted that I knew exactly what the product was, was driven to make it a reality and prove it to the world, and wanted to move into this space so that I could meet the caliber of person with whom I’d like to do business (more on this kind of strategic career positioning in Be Ambitious).
I sent the proposal over to the CEO, finished my coffee, and made my way back to the office. If he bit, immediate study and implementation of the proposal was on the table. If he balked or showed a bit of skepticism, I’d have to step up to the plate and make the case for myself that I could learn how to do sales and business development, despite just turning 21 and never really having done it before.
Arriving back at the office, I was greeted by a skeptical look.
“There’s one major problem with your proposal.”
Not possible. I had thought of every major objection and provided myself enough wiggle-room that any objection could be rationalized away with another part of the proposal.
“What’s that?”
“It’s too good.”
Oh.
“We need you doing what you’re doing now or need to find somebody to replace you — somebody to do application review and everything else you are doing so you can focus 100% on growing the business partner network.”
He was right. The team at this time was only three people — him, myself, and our education director — and we were running at full speed ahead. We drew up a plan to hire an alum and one of our own participants to take over and scale out much of the work I was keeping held together by metaphorical gum and duct tape at that time.
For the next two and a half years, I worked as Director of Business Development at Praxis and built a portfolio of business partners and connections worth well over $1B to myself and to Praxis. Today, I do business with several of these partners despite not working at Praxis anymore and continue to benefit from the social capital accrued during this time. I’ve learned firsthand from dozens of founders what it takes to grow a business, what it takes to hire well, and how to psychologically stand up to the difficulties of entrepreneurship. These are things most people only read of. It’s hardly like this was just handed to me for having the gall to send in an ambitious proposal to the CEO and convince him I could take on the work. In the beginning, I had business meetings where I felt eviscerated, forest fires I had to learn to extinguish, and a growing network of connections to keep happy and develop. Bouncing back from tribulations was a skill learned that made me stronger and accelerated my career more than simply putzing through the motions of a “regular” career progression (see Be Antifragile).
These opportunities would have never presented themselves to me and I would likely still be working my way through school or a slightly-above-entry-level job somewhere and wishing I could gain this experience if I had not been cocky. There was a voice inside my head that urged me not to send such a proposal along, telling me that if I failed I would look silly in the workplace. I shut that voice up (or overpowered it) and hit send. That decision pays dividends to this day.
[The next section focuses on strategies and tools I used to shut that voice up and condition myself for virtuous cockiness.]
