by Brian DeChesare Comments (33)

The Don Draper Guide to Investment Banking

The Don Draper Guide to Investment BankingA few years ago some banker friends and I were thinking about creating a TV show.

Entourage meets The Office: all the glamor of movie stars and the celebrity lifestyle, but in cubicles rather than Hollywood.

But the outside world has never hated Wall Street more, and post-financial crisis there’s no way a drama like this could ever take off.

Plus, there’s another small problem: it would be impossible to make a show more awesome than Mad Men.

Don’t believe me?

Here are all the lessons you could learn from Don Draper himself:

1. Have a Great Name

You cannot underestimate the importance of having a name that rolls off the tongue: “Don Draper” is 100x better than “Dick Whitman,” so it’s no wonder that Don assumed someone else’s identity.

You’re judged on your name just like you’re judged on your appearance: so if your name sucks, change it or come up with a nickname or shortened version that’s easier to pronounce (just make sure it’s done officially so you can handle those pesky background checks).

Some people succeed without great names, but why take the chance?

2. Don’t Hook Up with Co-Workers

While Don has had dozens of affairs, up until season 4 he never crossed the hook-up-with-co-workers line.

And when he finally did cross the line, he hit rock-bottom and found himself more adrift than ever before.

You’re required to have affairs and random flings if you’re in finance – just make sure they’re not with co-workers or things will head south very quickly once it ends.

3. If You Do Hook Up With Co-Workers, Don’t Take the Marriage Seriously

So you just had a random fling with your secretary, suddenly decided that you’re in love, and proposed during a trip to California?

If Don can do it, you can too.

Remember that you cycle through wives or husbands approximately every 2 years in finance, so it’s perfectly fine.

With the amount of money you’ll make, alimony is almost an afterthought anyway.

4. Don’t Take Your Employment Contract Seriously, Either

Don didn’t even have a contract with Sterling Cooper until everyone realized he needed one, midway through season 3.

And even when he “signed” it, he didn’t use his real name and then broke the contract to leave and start his own firm anyway.

The role of contracts in investment banking is similar: they’re just a formality.

You could be fired at any time, or you could quit as soon as you find a better offer elsewhere – so have fun playing the field.

5. Take 4-Hour, 3-Martini Lunches

Has Don ever not gotten a hotel room with his mistress-of-the-moment after a 3-martini lunch?

You think you have to be available for clients and senior bankers 24/7, and that’s usually true…

…except for when you get that buy-side offer and are on your way out the door anyway.

Remember that no one cares about you at a bank: especially when you’re about to move on anyway, do the bare minimum to get paid and slack off as much as possible.

4 hours may seem like a long time for lunch, but if you’re leaving anyway and all the senior bankers are gone, who would notice?

6. If Conrad Hilton Calls You at 11 PM, Do Whatever He Says

And no, not just because his great-granddaughter is Paris Hilton.

If you have a high-maintenance client who’s worth millions of dollars and demands to speak to you 24/7, you better do whatever he says.

That includes getting his dry cleaning, dressing up as a clown at his kid’s birthday party, redecorating his house, and meeting him in the middle of the night just because he’s bored.

Remember, clients and work come before everything else – even if your wife is about to divorce you and your kids don’t remember who you are.

7. Exploit Loopholes for Personal Gain

So you just found out that your own firm is being acquired by a much larger company and you’d never want to work there.

Simple solution: just do what Don did and gather up everyone important and fire yourselves before the transaction goes through.

If your bank is actually getting acquired, the acquiring bank is smart enough to prevent that specific scenario with the reps and warranties in the definitive agreement

…But there are always other loopholes you can exploit.

Send out emails late at night to feign busyness, work hard during your first and last month and slack off the rest of the time – do whatever it takes to get top-tier bonus.

8. Keep Stacks of Alcohol in Your Cubicle

Bankers may not drink alcohol out in the open anymore like advertising guys did in the 60s, but if you work 100 hours a week you’re going to need alcohol and drugs – ideally cocaine – at some point.

Rather than running out to buy overpriced bottles constantly, keep a stash hidden away in your cubicle.

Once the support staff and senior bankers are gone, you have free reign to do whatever you want.

So if it’s 3 AM and your balance sheet isn’t balancing, just pull out your Jack, take a swig, and hope for a moment of clarity.

9. Don’t Lie on Background Check Forms

Don gets away with assuming someone else’s identity for years, but it finally catches up with him in season 4 as North American Aviation, a new client, demands background checks on everyone so they can receive security clearances.

And if you’ve been lying about your identity for years, background checks are the last thing you want to think about – so Don forces his company to drop the client.

You might think that’s bad – but if you lie on your own background check forms, something much worse will happen: you’ll get your offer rescinded and you might even have your career destroyed with the right chain reaction of forwarded emails.

10. Think on Your Feet

So the government has started telling everyone that cigarettes kill you – and your top client is Lucky Strike.

They put you on the spot in front of everyone else and ask you how to address these claims and market the product.

Simple solution: avoid the issue altogether. “It’s toasted.” – everyone else’s tobacco is poisonous, but yours is special.

Remember that investment banking is a sales job: it’s less about analysis and more about selling, relationships, and thinking quickly.

Even as an analyst you’ll be put on the spot all the time when your MD or VP ask about your work or for specific numbers – so you better be prepared.

11. If You Get Arrested for Drunk Driving, Get Your Most Trusted Friend to Bail You Out

After indulging in alcohol yet again, Don finds himself in a wrecked car and in police custody along with his “female companion” of the moment.

So he does what any reasonable businessman would do: he calls Peggy, the one person he can trust to bail him out without telling anyone else at Sterling Cooper.

You should also have a “designated friend” to bail you out, because you’ll probably be arrested for drugs or alcohol at least a few times.

Just make sure it happens after you’ve already gone through background checks.

Got Don?

While you don’t want to follow everything Don does (e.g. sending a major announcement about your firm to the NY Times without consulting anyone else first), you can pick up a lot from him.

Advertising in the 1960s was just like finance in the 2000s: the most prestigious and highest-paying industry.

And if Don were in business today, he’d surely be a Partner at a bank or PE firm – so watch Mad Men and take notes the whole time.

M&I - Brian

About the Author

Brian DeChesare is the Founder of Mergers & Inquisitions and Breaking Into Wall Street. In his spare time, he enjoys memorizing obscure Excel functions, editing resumes, obsessing over TV shows, traveling like a drug dealer, and defeating Sauron.

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by Brian DeChesare Comments (53)

How to Quit Your Investment Banking Job Without Getting Executed

How to Quit Your Investment Banking Job Without Getting Executed

Midway through every year, a whisper starts growing at investment banks everywhere.

“This sucks. I’m gonna quit.”

Sometimes it’s so bad that you just want out immediately.

Other times, you plan to wait and stealthily make an exit as soon as your bonus hits your bank account.

So here’s how you can break out of investment banking – without dying in the process.

Your Mission

It’s not as simple as announcing that you’re leaving and storming out of the building.

Yes, you could do that… but it will create some problems for you in the future.

To make your quitting successful, you need to:

  1. Make sure no one else knows anything about it beforehand / prevent rumors from circulating.
  2. Avoid burning bridges (if you can) because you might need recommendations in the future.
  3. Line up another offer first or have a plan for what you’ll do after you quit and spend a week on a tropical island.

You probably understand the importance of point #3, but I’ve seen many quitting bankers forget #1 and #2.

How to Escape the Executioner

Here’s what you need to do once you’ve made the decision to jump ship:

Get Over Yourself

Repeat after me: no one cares about you… at all. You are a very small cog in a very large wheel.

In “normal” industries if you tell your boss you’re leaving, he might say, “We really need you right now! Can you stay for a few more weeks?”

Or who knows, maybe he’ll even offer up a promotion or try to bribe you into staying longer.

You don’t have to worry about any of that in finance: as soon as you say you’re quitting, they’ll say, “Good, here’s the door. Please leave now.”

A lot of junior bankers overestimate their own importance – “Trophy Kid” syndrome.

But most people won’t even remember you the next day.

Prepare for an Immediate Exit

Next, understand that once you announce your plan to quit your exit will be immediate.

You don’t get a “going away party” or presents or any of that nonsense – you get escorted to the building exit.

There’s a practical reason for this: you have access to a lot of confidential information about public companies.

If you continued to have access to that information, you could spread it around to other people, competitors, or make a quick million or so with insider trading.

It’s almost as fast as getting fired, but sometimes – depending on the bank and group – they will let you stick around for a few days to a week to hand off your tasks to other analysts.

Save anything important – both physical possessions and computer files – in advance of quitting, because you won’t have time later.

Make Sure Your Exit Strategy Is Lined Up

No matter how bad you have it, it’s a really, really, really bad idea to quit if you don’t already have another offer lined up or at least some idea of what you want to do next.

So if you’re quitting to start your own fashion company, obviously you won’t have an “offer” but you should have some idea of how much money you’ll need, what you’re going to do, and an understanding your market.

And if you are continuing on within finance, you should have an offer somewhere else.

In “normal” industries it’s much tougher to get hired when you’re unemployed, and it’s exponentially harder in finance.

So you should not go and “announce” anything to anyone until you have a signed, accepted offer with another bank, hedge fund or PE firm, or a concrete plan of what you’re going to do if you’re leaving finance.

Make a Clean Break

Once you’ve prepared yourself, you need to avoid screwing up the final step of quitting – actually telling people that you’re quitting.

Here’s what NOT to do:

So once you’re set, go directly to your MD, in-person, and explain the situation:

“I’ve enjoyed my time here, but I’ve just received an offer for [Name of New Job], and they want me to start immediately – so I’ll be leaving.”

At this point your MD will probably jump in and act professionally about it – or he’ll complain about how much work you’re leaving behind, especially if it’s at a smaller bank.

Do not get emotional or give into any demands or last-minute requests.

You’re quitting. If you say “no” to these demands, what will they do? Fire you?

Saying “yes” won’t put you on better terms, either – if they make last-minute demands of you, they wouldn’t write a good recommendation in the first place.

Once you’ve told your MD, go around and say the same thing to your other team members, keeping it brief and unemotional.

Then, depending on whether you have to leave immediately or you have a few days to a week, go and craft a brief farewell email with your new contact information.

Don’t send this out to the entire investment banking department or the entire bank – you’re not that important.

Just send it to your own group, or to anyone you’ve worked with in the past.

A Tale of 2 Analysts

Similar to a tale of 2 summer interns, a quick tale of 2 quitting analysts will illustrate just how important the above points are.

Bitter Quitter

Bitter Quitter was at a bulge bracket investment bank and received a hedge fund offer just before bonuses were announced – right around the 1-year mark.

He hated his life and desperately wanted to get out, but he made the mistake of telling all the other analysts in his office before anything was official.

“I’m really close to getting this hedge fund offer… then I’ll be out of here!”

Rule #1 of quitting your job: don’t tell anyone you’re quitting.

Assume that anything you tell a single person at your bank will instantly spread to everyone else – office gossip happens 24/7.

Bitter Quitter eventually won the offer, but he made the critical mistake of not telling anyone higher-up directly – they found out through the grapevine instead.

So he didn’t even get to “quit” – instead, the staffer approached him and said, “We know what you’re doing. Please get out right now.”

Result: He never got to tell his MD himself, so he left on poor terms and would have trouble getting a good recommendation for business school or anything else in the future.

Clean Breaker

Clean Breaker was working at a middle-market investment bank, and received an offer to move to the corporate finance department of a Fortune 500 company, a few months after bonuses had been awarded.

He also hated his life (notice a common theme here?), mostly because one VP he worked for could best be described as “evil incarnate.” He was incredibly out-of-shape, had no life outside work, no friends, and spent all day making his analysts and associates miserable.

Even though Clean Breaker was miserable, he wasn’t foolish – so he didn’t tell a single soul that he was even interviewing until he had the signed offer in hand.

“Trips to the dentist” and “personal days” are plausible if you don’t use them every single week.

When the time came, he went directly to his MD first and told him the news, then informed Evil VP and the rest of his team.

Evil VP got visibly angry and spent 30 minutes trying to convince Clean Breaker to stay (this only happens at smaller banks), but Clean Breaker held firm and said, “Thanks, but I’m out.”

Result: Clean Breaker probably can’t get a recommendation from his VP, but there’s nothing he could have done to prevent that. But since he handled it professionally, he could easily go back to his MD and ask for help in the future.

How to Quit

Quitting your job is like removing a band-aid: make it quick and clean, and accept that it’s going to be painful in the short-term.

That’s way better than spending an eternity peeling it off and enduring the pain over weeks or month.

So make it quick, professional, and confidential and you might just escape with your head intact.

M&I - Brian

About the Author

Brian DeChesare is the Founder of Mergers & Inquisitions and Breaking Into Wall Street. In his spare time, he enjoys memorizing obscure Excel functions, editing resumes, obsessing over TV shows, traveling like a drug dealer, and defeating Sauron.

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