How the Sausage Gets Made

What fifteen years inside corporate breakups, VC boardrooms, and crypto chaos taught me about innovation

A senior HR leader looked at me, confused. “And…why would you want to do that?”

“I don’t know, exactly,” I shrugged. “I just have a feeling it would help me know who I was writing for. You know, what does the average person here think about what’s actually going on?”

That “tour with the average employee” never ended up happening. We wrote the comms the normal way, by listening to executives who listened to managers who listened to the finance team who listened to the country GMs, who conveyed it all to the HR team, who hired our small consulting shop to put it all into neat little words and glossy PDFs.

But I’ve always wondered: What was it really like for people who worked on the ground floor?

Years later, when I worked at Union Square Ventures, each Monday invited a new founder prototype, each wearing their very strong convictions about some far-off future-state view of the world as it could become.

Over the course of an hour, they’d pitch us their ideas, and we’d interrogate them about their big vision, their underlying tech stack, their business model, their team, and their willingness to incorporate feedback.

I was 28 years old and had no idea how startups got funded, let alone how ideas went from theory to execution. But it was my job to help every company find their way through the murky middle, largely by way of connecting them to other people who’d done it before.

One day I realized that I was getting a very skewed look at the world of entrepreneurship and innovation. My “investor radar” was getting sharper, but I was totally blind to the thousand micro-decisions a founder had to make just to get to our front door.

I had a lot of questions about some of the odd behaviors I noticed among founders who came into the room:

• What was with the frantic, last-minute edits to their slide decks?

• Why insist on a live demo of something they’d clearly just finished the night before?

• Why wear a hoodie to a meeting where millions of dollars were on the table?

When I’d meet with these new teams shortly after they raised their seed or series A investments, I started noticing some surprising patterns. Founders who were completely oblivious about major pop culture events. Shared office sublets, with dirty dishes piled up on sinks. Processes held together with duct tape and glue.

Something didn’t quite land for me between the big-picture vision and the messy reality. If these were the future titans of industry, I had to see the raw materials.

I needed to know: What really happened in the months (or years) before they ever stepped foot in a boardroom?

So I inserted myself with gusto into the community I’d always understood the least: The crypto community. Over the course of three years, I enmeshed myself with a new persona of peers. Not the senior executives. Not the VCs. The builders.

I was 35 years old and had no idea how crypto really worked, let alone how to insert myself into the narrative texture of this industry as a non-engineer. But I made it my job to find a way to make myself useful as a community builder and a connector. So I’d show up hacker houses with “NO VC’S ALLOWED” signs on the front door and watch engineers sabre champagne bottles and talk about token economics, while regaling them with stories I’d heard of how Twitter first came to be.

I learned that thousands of people traveled the world like nomads, picking up crypto projects like new hobbies and treating the developer event circuit like a summer camp for grown-ups. I met people at the very earliest beginnings of their ideas. One month in, three months in. I heard them pitch their dreams with a feverish certainty. I believed them when they told me this wasn’t just another crypto project; it was the one the world had been waiting for.

I was there when those projects launched, fresh off whiteboard planning meetings and straight into hackathons. I was there when projects collapsed, hot off the FTX meltdown. And I heard, all along the way, the repeated mantra from the true believers drone on, like a drum cadence from a marching band:

WGMI
We gonna make it

As the months and years went by, I started to see the cracks in the plaster. Bad hires that nearly took down companies. Legal decisions that made my jaw drop. Stories of massive financial loss. Stories of massive financial windfalls. Teams coming together. Teams falling apart. But I kept showing up. I kept getting jobs. The building continued.

The same founders who had looked me in the eye and told me their dreams years before started to pivot. Some shut down their businesses entirely. But what surprised me the most was how they didn’t lose steam. They kept showing up. They changed their minds, but they kept playing, anyway.

So when the market rebounded and a new cycle started fresh, they just dusted themselves off and came back with a fresh idea and resurfaced. One free life redeemed.

Ah. I finally realized. So this is how the game is played.

A senior HR leader looked at me, confused. “And…why would you want to do that?”

“I don’t know, exactly,” I shrugged. “I just have a feeling it would help me know who I was writing for. You know, what does the average person here think about what’s actually going on?”

That “tour with the average employee” never ended up happening. We wrote the comms the normal way, by listening to executives who listened to managers who listened to the finance team who listened to the country GMs, who conveyed it all to the HR team, who hired our small consulting shop to put it all into neat little words and glossy PDFs.

But I’ve always wondered: What was it really like for people who worked on the ground floor?

Years later, when I worked at Union Square Ventures, each Monday invited a new founder prototype, each wearing their very strong convictions about some far-off future-state view of the world as it could become.

Over the course of an hour, they’d pitch us their ideas, and we’d interrogate them about their big vision, their underlying tech stack, their business model, their team, and their willingness to incorporate feedback.

I was 28 years old and had no idea how startups got funded, let alone how ideas went from theory to execution. But it was my job to help every company find their way through the murky middle, largely by way of connecting them to other people who’d done it before.

One day I realized that I was getting a very skewed look at the world of entrepreneurship and innovation. My “investor radar” was getting sharper, but I was totally blind to the thousand micro-decisions a founder had to make just to get to our front door.

I had a lot of questions about some of the odd behaviors I noticed among founders who came into the room:

• What was with the frantic, last-minute edits to their slide decks?

• Why insist on a live demo of something they’d clearly just finished the night before?

• Why wear a hoodie to a meeting where millions of dollars were on the table?

When I’d meet with these new teams shortly after they raised their seed or series A investments, I started noticing some surprising patterns. Founders who were completely oblivious about major pop culture events. Shared office sublets, with dirty dishes piled up on sinks. Processes held together with duct tape and glue.

Something didn’t quite land for me between the big-picture vision and the messy reality. If these were the future titans of industry, I had to see the raw materials.

I needed to know: What really happened in the months (or years) before they ever stepped foot in a boardroom?

So I inserted myself with gusto into the community I’d always understood the least: The crypto community. Over the course of three years, I enmeshed myself with a new persona of peers. Not the senior executives. Not the VCs. The builders.

I was 35 years old and had no idea how crypto really worked, let alone how to insert myself into the narrative texture of this industry as a non-engineer. But I made it my job to find a way to make myself useful as a community builder and a connector. So I’d show up hacker houses with “NO VC’S ALLOWED” signs on the front door and watch engineers sabre champagne bottles and talk about token economics, while regaling them with stories I’d heard of how Twitter first came to be.

I learned that thousands of people traveled the world like nomads, picking up crypto projects like new hobbies and treating the developer event circuit like a summer camp for grown-ups. I met people at the very earliest beginnings of their ideas. One month in, three months in. I heard them pitch their dreams with a feverish certainty. I believed them when they told me this wasn’t just another crypto project; it was the one the world had been waiting for.

I was there when those projects launched, fresh off whiteboard planning meetings and straight into hackathons. I was there when projects collapsed, hot off the FTX meltdown. And I heard, all along the way, the repeated mantra from the true believers drone on, like a drum cadence from a marching band:

WGMI
We gonna make it

As the months and years went by, I started to see the cracks in the plaster. Bad hires that nearly took down companies. Legal decisions that made my jaw drop. Stories of massive financial loss. Stories of massive financial windfalls. Teams coming together. Teams falling apart. But I kept showing up. I kept getting jobs. The building continued.

The same founders who had looked me in the eye and told me their dreams years before started to pivot. Some shut down their businesses entirely. But what surprised me the most was how they didn’t lose steam. They kept showing up. They changed their minds, but they kept playing, anyway.

So when the market rebounded and a new cycle started fresh, they just dusted themselves off and came back with a fresh idea and resurfaced. One free life redeemed.

Ah. I finally realized. So this is how the game is played.