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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  1. 1. Were you serious with changing our name?
    2. “And if Don were in business today, he’d surely be a Partner at a bank or PE firm . . .” WHat would Pete be in?

  2. Wasn’t finance “the most prestigious and highest-paying industry” in the ’80s?
    What is “the most prestigious and highest-paying industry” in the 2010s?

    1. Avatar
      M&I - Nicole

      Probably tech.

  3. also for #6 if Lee Garner from Lucky Strike wants you to dress up as Santa Clause at the Christmas party and allow him to flirt with your trophy wife, you better let him do that too haha

    1. Yes excellent point – or if he makes you hook up with the hot receptionist (one can always hope…).

      1. Avatar
        Pete Campbell

        #7 If a gay employee rejects advances from Lee, fire him.

  4. Best article ever. Don’t bring a John Deere to work – “it’s like Iwo Jima out there.”

    1. Haha yes, great line.

  5. Is the cocaine thing serious? I’m actually asking since a 100 hour weeks really could drive one to that point….

    And also Brian, you should write an article on how to not go to parties, events and save money (except company-sponsored events where drinks are free)as much as possible and still maximize networking options.

    1. No most bankers don’t actually do drugs, they just talk about them. Thanks for the suggestion but I’m not qualified to write about that as I rarely network these days (too busy/constantly traveling).

  6. Does every BB office have a Joanie? Va-va-va-voom. 90 hrs a week in the office would seem like a joy.

    1. Unfortunately no, should be a requirement though

  7. Great article. I’ve been a secret reader for a few months now. My question/comment is in the recruiting process though. I spent May-July(this year)tediously preparing my resume. Everyone that reviews it (friends, career center, advisers) all say it’s a home run. Good GPA, relevant work experience with a few unique companies, and I have all the community / leadership development that most banks are looking for (my opinion). Starting in August I began emailing resumes/cover letters as well as mailing them and I’ve submitted it to over 12 banks, some bb some boutiques. I live in the midwest and have applied to mostly east coast with a few west coast companies And here we are entering November and I haven’t heard a yes or a no from anyone.

    the question: Typically, for people that live far away and aren’t from a target school, would we be one of the last people contacted for interviews? And do you think that for someone in my case, this process would be initiated by a phone interview first? please comment or email.

    1. You can have the most spectacular resume ever, but it doesn’t matter if you applied the way you did: you need to get on the phone, start cold-calling like crazy, and pound the pavement until you get in. Sending out blind applications online does nothing. At this point you haven’t been selected for anything, so please read everything under Recruiting at the top of this page and implement everything there… there are dozens of articles on how to network properly.

  8. Hello Don,

    I am just in trouble in having a english name. I mentioned “Don” is a good name, and what else? because I am from China, so I am not good at distinguish what is good or bad for. so could you give me some more suggestion, how to judge a name. mank Thanks.


    1. That wasn’t a serious point… I’m not literally advising you to change your name.

    2. Avatar
      Don Draper

      Don Xiang Draper would raise eye brows during screening

  9. You do have a knack for adapting TV shows to the IB lifestyle. Maybe you should have a special section on the website for this ;)… about doing Weeds next? It’s my fav show, and a Nancy Botwin guide to investment banking wouldn’t be such a bad idea, you could even list Mexico as the destination for laid-off bankers heh. But wait, I forgot that there are almost no women in banking..

    1. Haha I’ve never seen Weeds before but will check it out when I have a chance. I also thought about some of my other favorites (The Wire, Breaking Bad, etc.) but those are much harder to apply to banking. It sort of has to be something business-related or at least have bureaucracy in it… maybe Damages.

      1. definitely try for breaking bad, that would be bad ass if you could put that together

  10. Haha, great read. I’m actually finishing up season 1 – and yes it’s a good show about the corporate world.

    #10 is big. Think on your feet. “It’s toasted.” I wonder what the equivalent in finance would be for all the piece of crap financials that have piles of mortgage debt. “We’re still here”?

    #11 Peggy was his paid secretary – not everyone has one these days but I guess the idea is what’s important – somebody on your side.

    I found my old boss was into this show but not too many folks younger knew about it. Guess it’ll start growing.

    1. “At least we’re not Enron.” All aspiring bankers should be watching.

      P.S. Don’t use your real full name for comments on the Internet, fool…

  11. Is the whole cocaine use thing a certainty within the investment banking fraternity? Is it a world wide phenomenon or is it indegenous to the USA only? I’m a South African.I’ve Wall Street 2 money never sleeps. Is the movie an accurate depiction of the Finance industry?

    Many Thanks

    1. Avatar
      black label

      i dont think its that hectic here in south africa, with regards to cocaine and all.

      here in joburg, when times get tough, whip out a 6 pack of black label, and hope for the best!

      hopefully in 2-3 years, when im done with my studying, il be working at one of the banks here.

      any advice as whether or not vacation work(internships) are available here?
      seems like they only care about accountants and the big 4 here.

      thanx for any help!!

      1. They are available but maybe not as common as in other regions.

    2. It’s a movie, so no it is not an accurate depiction of anything. Cocaine use happens but it’s not as common as you would think… I just write about it here because drugs and killing people are my favorite topics and it fits in with the Inquisitions theme.

  12. Awesome blog post, just caught up with all mad men episodes, and this is exactly how I felt. Your great writing has way better train of thoughts of course, much appreciated!

    1. Yeah Don Draper should really be an inspiration to all new bankers… forget about Gordon Gekko.

      1. He’s in PE anyway.

  13. Good read as always, but I was hoping to begin watching Mad Men at some point ;/

    1. Yeah I was going to put a spoiler warning but felt it took away from the flow – you can still watch even if you know the basic outline, there’s a ton of stuff I couldn’t fit into this.

      1. love mad men. wish i could get around to watching all of it.
        do you see financiers’ fashion heading in the direction MadMen?

        1. I’m the worst source on this one, but I don’t think Wall Street fashion changes much from year-to-year so probably not – plus most bankers don’t watch the show.

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