In college, I wanted to begin a career on Wall Street. There were a number of books on investing that resonated with me, like Dodd and Graham’s Security Analysis, and Malkiel’s A Random Walk Down Wall Street. These works preached of a mindset that made sense to me, with lessons about the difference between speculating and investing, building in a margin of safety to decisions, and simplifying problems.
I was also lucky enough to meet some talented and creative professionals who learned about business, people, and leadership from their careers in finance. However, I saw things about the culture and lifestyle on “The Street” that didn’t jive with me. To be clear, these weren’t necessarily the same criticisms of sadism and evil broadcasted by the mass media (yes, there is greed and abuse on Wall Street, but also many good people). My observation was that quite a few of the young folks going into careers at banks surrounding firms were quite sheepish, and clung to prestige as a crutch. They learned how to use financial statements and build models, an exercise that I’d recommend to anyone wanting to go into business, but never moved beyond the hard skills.
Many people choose the path of salary man in this domain, essentially becoming the grunts or button pushers of a company. It can be a decent living, but it is also a multi-decade grind of working on someone else’s terms. However, I liked that a person could graduate past this and realize great success if they learned to make their own deals and investments. I knew that this was happening at the top levels and that I needed to contact the true decision makers if I wanted to skip rungs on the ladder.
Because of this, I went straight for the jugular by emailing the hedge fund managers that I admired the most. With no introductions, I established contact with dozens of executives, a few of whom were bona fide magnates. Even though I was never invited to tag along with them on their yachts, making the connections was a huge win for me. I knew that my message needed to be tweaked to increase success, but at least my signal was getting picked up.
While I interviewed my entire senior year for analyst and trading positions at many of the big banks, I ended up taking my first job outside of that world, where I was able to combine my interests in technology and economics. I did not find my dream job on Wall Street, but also learned a great deal about myself through the process. I made huge leaps in my ability to network and found the courage to reach out to A-listers for the first time.
Unfortunately, I lost that part of myself for a little while, until only recently, when I woke up from a drowsy spell of complacency. I’m glad to once again be in touch with the hustle mindset, as it’s one of the things I take pride in, and a lot of people took to my underdog story during the journey toward that first job. Below is how I used that sense of pride to overcome shyness and put myself on the line. I’ve outlined a few steps to improve the odds of winning.
Always be Intentional
If you lack a good reason to reach out to a big name, don’t bother. These interactions should always be win-win. A-listers wake up with the same number of hours in a day as anyone else on this planet, and most of them are usually booked solid. Unless your call/email is laser targeted, you’ll probably be passed on for a response.
On the flip side, once you have a good reason, follow through. I don’t always make good on this one, and I recently looked back at some of my emails thinking, “if only I had pressed further – I could have built a great relationship. The groundwork was already laid.” This was incredibly stressful for me at first, but turned into a huge rush and a sort of game to me.
We are all human and second guess ourselves, but there usually is a reward one step beyond our comfort zones. When getting ready to open correspondence, ask these questions to help remain intentional:
- What is my end game?
This is probably the hardest question to answer, and the period of reflection can be uncomfortable. The philosopher Kierkegaard said that anxiety is the dizziness of freedom. In a world of so many alternatives, choosing a single end game and cutting off other options can be paralyzing. However, properly selecting a path can free up tremendous willpower and motivation to pursue a meaningful goal to its maximum. Answer this question, and half the battle is won.
In my case, I gave up seeking consulting, political, sales, and other paths that appealed to me at some level, so that I could go after the one that appealed to me most in that time. It helped me go all-in on the matter, and people gave me the time of day because they smelled the conviction on me. You can always move on to other interests over time, but give your lead horse a fair shot.
- If I can have only one thing from this person (a look at my resume, a read of my blog post, a date for coffee), what would it be?
Don’t bend to the temptation, and only bring up this one thing in your initial back and forth. People respond best to one request at a time, and become increasingly annoyed as the list of asks lengthens. I personally would be happy to pick a buddy up from the train station, but would become less pleased if also asked to pick up their dry cleaning and grab them lunch on the way over. Keep the request small when building rapport – once you have someone in exchange with you (answering an email, or giving advice), they are invested in you at a conscious and subconscious level. Good things can happen from here.
- How can I cut this message in half?
Getting to the point is critical in a first interaction. You begin as an outsider and have to prove yourself. If you are anything like me, you’ll feel a need to justify your back-story and talk about yourself. Resist your ability to display social proof and creative prowess. Approach with hat in hand, explain the reason of your reaching out concisely, and step back. Directness is courteous of others’ time, and signals competence in a business setting. Long-winded copy writing has a place, but it’s not here.
- Does my fist sentence build rapport?
It’s not the end of the world if you don’t share the same blood type as your recipient, but a bridge of connection can make the difference between a reply, and the trash bin. If you haven’t read a book by them, or attended a conference, find a cause that you share interest in or an aspect of their past. If you are pitching an idea, speak to them about why this is especially interesting to them, and how they will benefit.
- Have I done all that I can to offer this person something worthwhile?
Think hard, and if the answer to this question is an honest no, then get back to the drawing board to come up with better offers. A job seeker can provide to work for a free trial period, or an entrepreneur can send a free sample product. There are so many ways to do something for others, and the gesture of asking is usually what matters more than the offering itself.
- Would you respond to this?
If you saw the subject line in your inbox, would you open? If you opened, would you be overwhelmed by three paragraphs of information as your important meeting approaches? Put yourself in the other person’s shoes; they are probably up against deadlines, receive thousands of emails per week, and don’t always have good days. Empathy goes a long way, and is the key to achieving “psychic powers”.
I have a high powered mentor who told me, “I am at the point where I’d rather give thousands of dollars to a cause than to offer them a day of my time. I might be selfish on some level, but that’s not the reason I’d make that trade.” To him, time had become the scarcest of resources.
Show Your Human Side
Take any celebrity or big name that you can think of – If you force feed them a Taco Bell Beefy 5 Layer Burrito…they’re going to have explosive diarrhea in an hour (I see you, Barbara Walters). They all have good days and bad, deal with heartbreak and embarrassment. No matter how high you go, you are still a person. We don’t relate to each other through sterility – it’s vulnerability, humor, and sincerity that allow us to be remembered by others.
I’m not saying that you should be cracking profane jokes on a cold call or be anything less than respectful, but a moment of self-deprecation can set you apart from all of the other randos on the internet. Acknowledging that your audience doesn’t owe you anything or that you’re struggling and could use a piece of advice has gotten responses for me.
Don’t Pander – People respect unapologetic hustle
If we cross the line from respectful to desperate, it’s only going to count against us. Being humble is an asset, but showing weakness signals low value –that little good will come out of dealing us. I’d venture to say that this was my biggest misstep in my early attempts and networking, and it comes from the mindset that we have nothing worthwhile to offer. Below is the difference in tone between deferential confidence and outright self-dismissal – one is a quick peck on the butt, the other is an excessive kiss.
I appreciate you taking the time to read this, and I’ll keep it brief (Acknowledge your audience’s needs).
You are already a heavy hitter in the semiconductor business, and I noticed that your company also began exploring cloud storage (Show awareness). I’d like to put you in touch with Don Smith, who is of similar stature in that industry (your ability to connect signals value). If you don’t already know him, I think you two would get a lot out of each other. He is very approachable and is a pioneer in the field (More social proof). Would you like me to make the introduction?
PS: I’ve always admired your style of business. Would it be at all possible to set up a 15 minute phone call where I could ask you a few questions (Politely make an offer, signal that you are worthy of their time)? It would make a big difference in my personal development if you were able, but I’d also be grateful to keep touch via email if that weren’t feasible at this time (Shows that you know exactly what you want, but gives them an out).
Let me know what’s best for you, and thanks.
I know you are busy, but I hope you’ll see this (Already on defensive).
You are already a true titan of the semiconductor business with an amazing track record and company, which looks to be moving towards cloud storage. You probably know Don Smith already, but if not I might be able to introduce you to him (not sure of your ability to line up an introduction). He is big in the cloud storage industry, and might agree to a meeting.
PS: I’ve always really admired you. I don’t know if you’d ever want to take a phone call with me, but I am new to the business and am trying to break in (Still an outsider, no contingency or alternatives given).
Anyways, thank you so much for your time.
A few points to hit on here:
-Remember that the one making the offers is actually in a position of power (you in this case!)
-Never lie; you will probably get caught if the engagement goes on for long enough. However, it’s important that you put your best foot forward. Some people have initial guilt about spinning their reputation in a positive light (others are the complete opposite). However, I’d argue that if you are within the bounds truth, omitting that you are still a college student, or that you’ve never put together a high powered introduction before is perfectly fine at first. If something becomes material, cross that bridge when you get to it, and disclose the information.
-Be confident in your ability to make good on your pitch, but don’t purposely overpromise. I have a mentor that I really admire, who rose to become treasurer of a decently large bank by a fairly young age. One piece of advice that he offered me was to say yes when opportunities or ideas come, and figure out how to do them afterwards. To me, this is part of what having grit means – being adaptive, and willing to see something through, even when the roadmap isn’t laid out yet.
-It takes a confidence look outside oneself at another persons needs. If you are focusing on another person and how you can help them, you’re on the right track. To be very clear, focusing on some else is different than focusing on what someone else thinks of you. There are a lot of people out there who fixate on evoking a response out of somebody, or analyzing their behavior. However this can have a narcissistic bent to it, and not actually be about the other person. Showing true concern is a programmable exercise, and genuine care for others is a great sign of security within – just another thing that signals your high value.
Cross your T’s
I want to stress something here, and Tim Ferriss does a great job of explaining this in The Four Hour Workweek. Showing up puts you ahead of at least half of your competition. In the book, he talks about how you can often find success approaching the most beautiful person at the bar, as most people sell themselves short and hit on the second or third best looking. This applies over and over again in life, and your sheer effort can make up for a lack of finesse in many cases. It certainly did for me, and you’ll be able to see where I fell short of my own advice in this article when you check out my actual emails below.
In my emails to the top dogs, people running huge hedge funds and other institutions, I’d put my response rate at about ten to twenty percent. Not bad when you consider the pull that these people have. Out of respect, I will not include their names, but it’s safe to say that they show up in the major news media outlets, have written books, and are recognized as among the best in their trade.
If you are afraid, don’t worry about perfection, and just try – you will not be arrested for sending out a polite email into the universe. However, once you are over this fear, and have tasted the honey, you might as well maximize your chances of success. Even if you don’t know how to write the perfect email, there are landmines that you can easily avoid. Here are a few big ones.
–Spelling and punctuation errors
This is an instant deal breaker for some. As a self-respecting human being, make sure that your letters are in the right place. I get misspelled emails all the time, and in an era of spell check, they simply imply that you don’t have three extra seconds to click on the word with a red squiggly line under it, and press backspace. Correctly use pronouns, apostrophes, and tenses. If you are not a connoisseur of the written word (I am not), then get a “smart” friend to read your email over. It’s free to outsource 99 percent of the time and takes about two minutes.
There really isn’t any excuse. I’m not talking about a benign use of “Thx” if the conversation goes informal. However, if you are writing to a role model, “your a big inspirationto me”, it’s going to look amateur.
Your email (or call for that matter), should give the impression that you are ready to play ball, but by no means should you strive for robotic style (sorry my cyborg friends). This is in line with my suggestion to be human above. Come off as a smooth operator, not a Britannica groupie. Showing moments of vulnerability or excitement are game changers that can demonstrate that you’re special. Just refrain from calling them buddy if you aren’t friends yet.
There’s plenty of middle ground where you can carve out your personal style, but it is amazing how many times I’ve encountered messages from people who are entirely too formal, or informal. This is where knowing your audience comes in place. It might make sense to address a Wall Street exec as Ms. Jones, rather than Kate, but it’d probably be out of place to email a musician or artist that you admire with a formal prefix before their name. You’ll get the hang of this, and realize that you’ll never know the perfect answer for everyone. Just use common sense.
–Reach out at normal hours
If you want a response, send your message out a little before or after working hours. Allow the herd to send at hot times like 9am-12pm or 2pm-5pm. Sending between 6am and 8am, or 6pm and 7pm have worked best for me. I’ll have to revise once I actually crunch response rates, so this isn’t just anecdotal.
Before you worry about whether you’re sending within the optimal 15 minute window, know the basics. You do not want to be the guy that sets a media baron’s blackberry off at two in the morning. Let someone else do that. Even if they sleep through the night, if you’re message is buried under eight hours’ worth of other email, A) your chance at a response will go down and B) your message will have waited X hours for a response, so it becomes implied that the message can wait for another X hours.
You’ll be surprised by how strategically timed emails can yield near instant replies. We all tend to act on whatever has grabbed our attention in the moment.
By simply doing these three things, you will be far ahead of your competition.
Now that we’ve talked about the emails, let’s actually look at an email thread. I’ll be very clear in reiterating my above point. These emails did not get me a weekend in the Hamptons with the rich and famous. However, they offered the critical revelation that a well-crafted message can get a direct response from the elite, and the odds aren’t infinitesimally small. These messages can get read if you approach strategically and consistently. After that, it simply comes down to crafting the right message.
Here’s the thread:
Within five minutes, I got the below back from one of the top twenty hedge fund managers in the world.
A conditional no – unless someone at the firm is willing to work with me. He was honest, and wrote back directly to me. Expectations were already surpassed. If I were pitching a product, I still had room to try and convince, I’d just need to turn to someone else within the firm willing to work with me. The thread progresses, and without my asking, I get an email from the fund owner’s right hand man – a famous man in his own right.
Again, I was not given an outright no – if I could somehow offer more time (which I couldn’t), there was still the possibility to inquire further. At this point, I decided to question his response politely. In hindsight, my reply, was a bit “me-centric”, but it goes to show that you don’t have to be perfect to keep the ball rolling.
The reply I received:
This was great the fund’s number two guy gave me a soft no, and told me to keep in touch over the year. You might, protest that this was his way of getting me off of his back (it was), but he respected my reaching out enough to leave that line open. I did keep in touch with this guy, and I actually leveraged this experience to get a great internship at another fund, because other owner know this guy well and thought my conversation with him showed hustle. This was a great turning point for me, and I don’t see why anyone else couldn’t achieve similar results.
Mind you that I went to a state school with very few alumni in this industry, no family in the business, and a decent, but not exceedingly strong academic record. Yet, I guarantee that very few Harvard or Stanford guys were following through like this, and getting around the gatekeepers. I don’t elaborate on this to stroke my ego (at least I don’t consciously admit it) – it’s simply to demonstrate that intrinsic drive to succeed is an attribute assessed on its own, largely agnostic to background and pedigree.
Others will always have born advantages, but there is always a prize for those who hustle, given even with their limitations. I’ve had similar results with others on an equal footing, and it’s never hurt me to make the effort. Coming soon, I’ll address how you can get in touch with VIPs, creatively and conventionally. Happy hunting in the meantime.