If Hamilton Characters Were Venture Capital Revolutionaries

There’s symbolism in the room where Hamilton made deals.

Annette Miller
The Startup
5 min readSep 2, 2020

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Photo by Austin Distel on Unsplash

Revolution backdrop

As I watched Hamilton over the Independence Day weekend, an unexpected wave of feelings washed over me — surprise, outrage, confusion, disbelief.

We dream in the dark

I viscerally reacted because of the many parallels between the poetic scenes of the play and the current changes stirring in the American venture capital landscape. Scenes that particularly struck me were about the fundamental reimagining of society; distribution of power within sophisticated economic systems; and bitter, political rivalries.

Hamilton’s carefully curated and convened meeting… reminded me of all access barriers which frequently block founders from decision-makers and critical relationship networks today

In “The Room Where it Happened,” a dramatically choreographed ensemble tells the story of how black-box, network-driven political backroom negotiations unfold. Hamilton and Jefferson reach a series of critical compromises.

The way Hamilton’s meeting was carefully curated and convened rang familiar.

It reminded me of all access barriers which frequently block founders from decision-makers and critical relationship networks today. As a founder, to be in the room where deals happen requires, at a minimum:

  • How to get a meeting, usually via a warm intro
  • With whom to meet at a firm
  • What sorts of things they expect you to say, and not say, in meetings

Consequently, there are still many Zoom meetings and virtual coffee dates founders cannot access. To know how nearly always requires grooming, mentors, champions, introductions, and pedigree.

Change is swirling through the world of venture capital in 2020 — a revolution of sorts. Every day, more funds emerge to support women, people of color, Black, queer, and other marginalized founders. It is far from enough — far from equitable, just as American revolutionaries were not given equity in America until they fought for it. Even then, white men were disproportionate beneficiaries of the spoils of war.

Free land.

Voting rights.

Freedom.

Survival and advisors

The production especially shines the light on Hamilton’s interpersonal shortfallings in both his career and private life. As an orphan, his early years were about survival — not how to access elite networks or exercise the subtle art of “relationship building.”

Rather, he was a poor, young immigrant with little to offer his first love — America — and his wife, Eliza, except for his blank-slate reputation and brains. The same could be said of many underestimated founders today, still struggling to even get into the room with decision-makers.

To know how nearly always requires grooming, mentors, champions, introductions, and pedigree

When someone did take Hamilton under their wing (Burr) the advice he got was bad — stop bringing attention to the problems you want to fix in the world. How many underestimated founders have been told the same?

VC revolutionaries

The characters of Hamilton lend themselves well to those in today’s VC environment where social meaning, impact, sustainability, and purpose are being reexamined. This shows up in startups and firms focused on the future of work, healthcare innovations, impact investing, and beyond.

Power redistribution via economic inclusion in the startup ecosystem is palpable in the #HireandWire movement, which urges firms to both invest in Black founders and hire — then advance — Black associates.

Bitter, political rivalries have shown up most colorfully in recent weeks in the spat — or, rather, an attack escalated to a pinnacle of harassment due to misogyny — between a reporter and an old guard VC.

Alexander Hamilton
Underestimated founder

Hamilton was a poor immigrant with no social status nor polish. His brains and relentless pursuit of making an impact on America fueled his ascent to leadership, haters be damned. Prolific and influential writer — a content marketing genius. Always saying “I’m not throwin’ away my shot” and follows through tirelessly. An imperfect man with numerous known transgressions, Hamilton helps build the imperfect nation we live in today. The pride which helped him survive patinas his legacy.

Eliza Hamilton

Investors in, champions of diverse founders

After Alexander’s death, she cements his legacy by championing social issues and raising funds for the Washington monument. Uses her platform, collaborating with her sister, to influence public opinion on slavery. Memorializes her husband’s transcendence from unknown orphan immigrant to founding father by establishing an orphanage to give others a shot — she grows the size of the pie.

Arlan, Lolita Taub, and their contemporaries are who I envision in this interpretation of Eliza. These womxn and men collaborate, push, pull, drag, and inspire meaningful change however they’re able on important issues within the startup funding realm. They are revolutionaries in their own right as GPs (Lolita announced a fund yesterday!; Backstage Capital has been investing in ethnoracial and sexual minorities and women for years), angel investors, advisors, connectors, and friends to underestimated founders.

King George

Old guard GP

Sitting in the incumbent seat of power, he’s aloof and dangerous. The king gets a kick out of underestimating scrappy, young America’s drive for autonomy. Skillful at framing subjugation as “love.” Shocked and angered when his power is threatened.

Aaron Burr

Old guard advisor

Convinced he knows best. Always giving the advice to go with the flow. Ultimately kills Hamilton, hypocritically placing his own pride at the center of their rivalry — a behavior Burr renounced Hamilton for doing all his career.

Thomas Jefferson

Tech bro

After hanging out in France for the better part of a decade, Jefferson arrives home to the newly freed America with a privileged pre-approval to join Congress. Naive to the macro-economic realities of the new nation, he villainizes Hamilton’s US Treasury creation as overreaching bureaucracy. Excellent storyteller, but also a self-obsessed jerk.

George Washington

Experienced founder

He’s been in the trenches and has a profound respect for the fragility and immense influence of the role he occupies. Humble and forward-thinking about the bigger picture of America. But, exploits labor as a slave owner to enrich himself with a grand vineyard estate rather than set a moral precedent for economic equality in America.

Angelica Schuyler

Venture Capital scout

Savvy, smart, and self-aware as hell, Angelica is a feminist revolutionary. A consummate pragmatist, she sizes up Alexander’s character, economic prospects, and social capital. After realizing Alexander and Eliza are the right match, she facilitates their meeting.

“We dream of a brand new start
But we dream in the dark for the most part
Dark as a tomb where it happens
I’ve got to be in the room where it happens”
— Hamilton

Annette Miller is the Cofounder and CEO of Enriched Couples, a financial therapy platform that uses psychology to guide couples through unifying their values, financial priorities, and future goals.

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Annette Miller
The Startup

Marketer, former founder, behavior therapist. Outgoing introvert, gardener, ultra-curious woman with ADHD. Love the word avuncular and park best in reverse.