Top 5 Lessons Learned from Boardwalk Empire

I just got through Boardwalk Empire. It was all the things that the critics and fans say about it: entertaining, gratuitous, spectacular, and perhaps a little dark. However, I also found it instructive. I don’t mean literally of course (right guys?) but rather metaphorically when applied to my life as an entrepreneur, a thinker, and a friend to my friends. Perhaps you’ll agree with me, but if not, see #5 below.

Before you write off this whole exercise as ‘just a TV show’, keep in mind that there are some genuinely great teachers involved: Martin Scorcese, Terrence Winter, and much of the actual history that inspired the story.

Without further ado, the top 5 lessons learned from Boardwalk Empire:

5. Chumps come and go, but bosses are forever

One of the most basic surface-level observations is that there’s a big difference between the town plebes (who live in modest houses, wear modest clothes, and eat modest food) to the contenders that rub elbows with bosses and are trying to climb up in the world. Thats all good stuff: when in doubt, aspire to greatness. However, of those who are trying to play he big boys’ game, many are chumps. Total chumps. Chumps lose sight of the big picture, of the people that are important, and of the consequences to their actions. On the boardwalk, that will get you shot or screwed. Even while Hague is on the opposite side of the table to Nucky, he offers his perspective: “Guys like Edge come and go. Bosses like us are here to stay.” The real life takeaway: great people operate with great perspective.

4. Always take good advice (but only good advice)

Everytime someone recommends killing someone on the boardwalk, the recommendation is acted upon. (see: Nucky, Horowitz, Jimmy, The Commodore, Chaulky, etc). It doesn’t always work due to #1, below — but that’s a different story. The takeaway is to surround yourself with people you can trust see # 2, below, and if you do that right, you should also respect the perspective provided by your advisers. The converse is also true, as finally proven by Jimmy. The takeaway: creating a poorly selected roundtable can create advisors who are not really looking out for you, resulting in downfall.

3. Always offer more than you take (but remember to take)

As we observe Nucky in action. We see again and again that even though he’s a gangster, classically corrupt politician, and racketeer — he never turns down a favor, and gives away money like candy. But he’ll take too, when the opportunity strikes. The $1MM price tag of bailing out AR may have flown by the modern viewer — but before the gold standard fell off and with sharply lower general costs of living, that’s more than $25MM in purchasing power today. Well played, Nucky. Interesting that he is later lectured by AR to be patient and opportunistic. The takeaway: be as generous as you can, and wait for the opportune moment to take what’s yours.

2. Value trust above all else


One of the main differentiators between chumps and bosses is that bosses are true to their word (whether what they’ve promised is good or bad is a different question) while chumps are caught scheming and backstabbing blatantly. The people that bosses allow themselves to rely on – Chaulky White, Daugherty the AG, Capone, Luciano and even Jimmy (until he starts over reaching) have relationships built on trust and cemented through mutual favor debts. Or, if you’re AR, take our life insurance policies against your staff. Total boss. The takeaway: you’re only worth your word. Protect it’s value and expect the same of others.

1. You cannot take down a boss (but the boss can take down anyone)

Each time one of the major bosses faces a major adversity (Rothstein and his World Series indictment, Nucky and his mutiny, Horowitz vs Jimmy, Hague with Senator Edge, Torio vs the Greeks, Chaulky vs the Klan), they are given the chance to show why they are indeed a true boss. They show persistence, resourcefulness, creativity, and shrewd understanding of what the people around them want. In fact, in each of the major challenges above, the boss not only comes out on top, but creates one or more strong allies in the process. The takeaway: stay strong when things look their darkest. If you’re a true boss, you’ll come out stronger on the other side. 

And if not, at least you made room for the rest of us.

My thanks to my Clothes Horse cofounder Dave Whittemore who inspired a discussion that inspired this post.

  • Dave S

    Great blog and a cool take on the ‘teachers’ of Boardwalk! I couldn’t agree more!

  • Larry

    Interesting lessons. It is funny, Breaking Bad has the opposite take on #1. But then again, maybe the bosses weren’t really bosses…