How to Build a Cabinet: Leadership Lessons from the Hamilton Creative Team

The Hamilton Cabinet, who just received a special Kennedy Center Honors this December

The secret sauce is the team.

You might think it’s the writing — the cleverness of invention, the infusion of the old-school revolutionaries with the new school wave of hip hop.

Or maybe it’s the music — the bold orchestrations, bordering on maniacal as they manage to both drive the beat home while graciously leaving room for the vocalists. Or of course there’s the choreography, what with its elegance and agility, revealing sub-plots through dance that enhance the story through continuous movement.

It’s all of those things, of course. This perfect storm is what fostered the breakaway success of the Broadway musical and global phenomenon, Hamilton, smashing through every box office record (as it continues to do today).

But as I see so often with other hyper-growth startups in the tech industry, quite possibly, it’s none of those things.

For me, as an aspiring entrepreneur who closely observes intimate details of startup founding teams from my perch in venture capital, the thing I still can’t get out of my head, after all of these years watching Hamilton from the sidelines with a husband who’s worked on the show since the pre-Broadway run, is not the creative brilliance of the production — it’s the team dynamics of the leaders at the top.

Nicknamed The Cabinet, the four-person creative team of Hamilton (who by the way, just received a special Kennedy Center Honors) just may be the strongest executive team I’ve ever observed. And for the life of me, I can’t figure out how they made it happen.

Building Your Cabinet

At Union Square Ventures, where I work, I interact with dozens of tech entrepreneurs on a regular basis. One of the topics that fascinates me the most about running a business is how you find the right team early on to get all of the pieces to fall into place.

Today at USV, we have 75 companies in our active portfolio, with products ranging from drone marketplaces and flashcard study aids to crypto-currency wallets or period-tracking apps. We tend to invest around the Seed or Series A stage, when companies could be anywhere from 3–30 employees (and may not yet be generating any revenue).

This means we watch a lot of companies go from early inception to widespread scaling mode. The VC partners I work with have participated in many breakout success stories of their own over the years, with companies like Twitter, Etsy, and MongoDB included among our exited “alumni.”

There seems to be no perfect formula for how it gets done.

Once a year, we bring together our CEOs for an annual summit to meet, share ideas, and talk about the challenges of running fast-growing tech companies. Without fail, when we survey the attendees in advance, asking, “What questions would you like to discuss with other founders?” this one theme emerges year after year: Building out and managing an executive team.

There are a million questions and sub-categories that fall under this loaded topic, which is part of why recruiting, both the process of finding people as well as assessing their potential fit in advance, is now estimated as a $200 billion industry today.

But when I hear these questions surface among our founders, many of whom are first-time CEOs, I can’t help but point to examples in other places and ask the question: “How did they make it work?”

How did a guy who read a biography about a Founding Father on his vacation convince three of his friends to turn this story into a historical rap opera? And what can our entrepreneurs, future aspiring visionaries among dozens of specialized domains, learn from their early creative process?

Revolutionary Leadership

“This is going to be big.”

I sat frozen in my seat, afraid to emit any errant sound to distract from the stillness in the air at the end of “Satisfied.”

In the tech world, you might call this a “pitch meeting” — a glimpse at what something could be with the intent to attract investor attention and money to front the real thing. In theatre, it’s called a workshop, a lab, or a reading, and thanks to some clever favor-calling from my husband, the associate sound designer on the show, he managed to snag me a seat at the second ever full run-through of Hamilton.

Next to me sat the sound designer, ferociously scribbling notes on his pad with reminders and ideas to recall for the real staged production a few months down the road. On “stage,” just a large empty room where we crowded in the back with folding chairs, Lin’s smile said it all; you haven’t seen anything yet. Everyone in the room, which consisted of a mix of industry professionals and producers, prayed a silent prayer that it could stay this good for the next two hours, and we all settled a little bit deeper into our seats.

The energy and intensity stood out to me in the room even then, when the second act existed only as a staged singing with music stands, an act incomplete without the choreography that would come to define it.

I’ve been privileged to have VIP access to some of these little-big moments, and when I do, I pay close attention to The Cabinet from afar. With each new milestone — the move from the Public Theatre to the Richard Rodgers, the opening of the first tour, the opening of the second tour, the Grammy’s live performance, the Tony Awards — I’ve been generally “around.” The plus-one at every function who’s just dying to ask a litany of questions as I try in my brain to carve out that special space where the theatrical production ends and the startup story begins.

Drawing from these vignettes, the occasional rehearsal or cast party, as well as second-hand stories from my husband and his colleagues in the sound department, I’ve come to grow even more impressed with the lessons in leadership that I’ve gleaned from the Hamilton creative team.

Here’s what I’ve observed:

  • First, of course, there’s Lin — the crazy visionary without whom none of this would be possible. His is the creative dream-stuff that only exists in the wackiest and bravest of humans, the person who isn’t just thinking about today, but about the tomorrow after tomorrow. He’s the kind of entrepreneur we see so much of in the startup ecosystem and what makes my day job so fascinating and terrifying and inspiring all at once.
  • Next is Lac — one of the two deep technical experts on the production. If Hamilton were a tech company, music would be the back-end engineering, the foundation upon which nothing else would be possible, and the differentiator that no competitors can match. Lac’s brilliance, like the best CTOs I’ve met, is too profound to be explained; his philosophy to particular to pass along. Alex Lacamoire is to Hamilton what Werner Vogels is to Amazon: Precise, soulful, elegant, and a little bit wacky. Lac wrote every single note the band plays, all of the vocal arrangements, and then some. His team, much like the engineers at Amazon, is loyal to a fault.
  • Then there’s Andy, who breathes meaning into message with live action orientations on stage. If the music is the engineering back-end, then Hamilton’s choreography is the product — the front-end, masterfully designed user experience that makes the story accessible for audiences all over the world. Andy’s tenacity and conviction compels everyone to move the same way — and finding the right cast to meet this high bar is essential to getting it right.
  • And finally, there’s Tommy Kail, Hamilton’s director and Lin’s right-hand man since even before day one, as college comrades who teamed up first for the Lin’s founding musical, In the Heights. There’s no such thing as a COO of a musical, but Tommy is as close as they come. Often the smartest man in the room, Tommy’s sharp sense of knowing exactly what needs to get done next (and how) is what earns him such deep respect among cast and crew (even if he scares them a little). While everyone thinks of Lin as the man with all the words, Tommy is the one who always knows what to say, and whether it’s a congratulatory speech on an opening night or a rallying pep talk to boost morale, his composure and certainty will make you want to follow him anywhere.

And that’s The Cabinet. From as far as I can see, they operate a little like this:

Lin asks, “What if…” and Lac responds with, “Yes…and…” then Andy and Tommy build the product and rally the troops. In business, we might put this another way: Lin is the big-picture visionary, Lac is the technical specialist, and Andy and Tommy are the ones with operational expertise to make it happen. As many venture capitalists have learned the hard way, you need both to run a successful business.

There’s something magical, almost reverent, about watching the Hamilton creative team collaborate with each other. There’s an intensity of perfection, an unflappable trust, and a crazy shared dream that binds them together.

A visionary founder alone is often incomplete without a strong executive team they can trust to run with their dream. Everything else — all of the details and the strategies and the execution and the growth — it all trickles down from starting with a strong foundational core at the top.

The Greatest Startup in the World

You can’t just post an ad on LinkedIn to find the perfect co-founding team that can run with your vision. And I’ve noticed it’s so much easier said than done for founders to hand over essential elements of their business operations to a COO, like Lin did with Tommy.

It takes a level of self-awareness and humility that’s unprecedented, a diffusion of ego that you have to get over right from the start.

But if you want to run a successful business (or launch a mega-hit Broadway musical), you need the right team around you to make it happen.

So, how do you find your Cabinet? Is it luck? Do you have to rely on serendipity alone and hope that you’ll intersect with people who can serve as your perfect complements? Or is it strategic? Are there actions you can take or relationships you start to lead you to the right people?

I wish I knew how to find this sort of mutual, complementary, and symbiotic relationship myself. I wish I knew how to help our founders and CEOs find it themselves.

But for now, I’ll continue to see what I can learn from observing this dream-team in action from afar. It’s a pretty remarkable story to tell.

Originally published at Dry Erase.

GM @USV, alum of @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC

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