I can’t describe what it’s like to be Black and work in tech — everyone’s story is different. That said, two experiences come to mind:

1) Years ago, back when I was working at startups instead of covering them, I was in the green room at a tech conference. After several hours, one of the security guards assigned to the space approached me.

“Can I ask you a question?”

“Sure,” I said.

“How come we’re the only brothers in the room?”

I did a quick scan. He was right. There were probably 75 people there, but the only Black people in the space besides me were guarding it. I was so used to being the only chip in the cookie, I didn’t even clock it.

2) After I launched this podcast, I was at a different conference and got deep in conversation with a partner at a VC firm who invited me to join him for lunch. As we walked into a VIP area together, a guard grabbed me forcefully and restrained me.

When he realized I wasn’t keeping pace, the investor turned around, saw what had happened, and looked horrified.

“He’s with me,” he said. 

We went to eat, had a great conversation, and never discussed it again.

Pattern-matching is crucial in Silicon Valley, but when your mere presence in a room defies expectations, it changes the power dynamics and the rules you’re expected to play by. That’s why I invited Sean Green and James Norman of Black Operator Ventures, on the show.

“I don't want the next founder who looks like me to have to go through that same type of journey,” says Sean. “I just think we should be able to make it faster, quicker, and help them accelerate faster.”

Experienced operators and fairly sector-agnostic, James and Sean lead seed rounds for SaaS founders across the US and Canada. “We set the governance, both operationally and technically,” says James. “Average check size is about $1.2M, and then we selectively co-invest with pre-seed people we’ve known for a long time.”

We talk about why fundraising is a power-dynamic game — not a meritocracy — and why underrepresented founders have to master the theater of venture capital without losing themselves in the process. 

James and Sean also break down what they look for when leading seed rounds, why warm intros function as the first real filter, and how founders can manufacture momentum even without friends-and-family money.

If you’re an underrepresented founder trying to de-risk your leap, get into the right rooms, or just trying understand why the rules feel unwritten, you’ll want to listen.

(1:52)  What motivated Sean and James to start Black Operator Ventures

(6:51) Where are they looking for opportunities?

(8:27) Top priority: Founders building real-world solutions with few regulatory hurdles

(11:44) Why obtaining a warm intro to a VC is a founder's first test

(15:20)  Fundraising is theater: Study the audience to learn your role

(22:29) Red flags first-time founders should avoid waving

(27:00) Tactical advice for aspiring founders who still work full-time jobs

(30:24) “ It doesn't seem risky because we're betting on ourselves, and we believe we can do anything.”

(34:38) How to find out if you should bootstrap or find a backer

(38:30) Which signals tell Sean and James a founder is ready for a check

(41:55) Why founders still need to spend some time in Silicon Valley

(46:02) Black founders can " 10x ourselves with AI in ways that other people can't."

(48:32) One action you can take this week to extend your network

I moved everything off Substack so I can centralize here.

Become a paid supporter. It directly buys me time to make more deeply-reported, founder-first conversations like this one.

Thanks for reading,

— Walter.