Jomayra Herrera is a principal at Cowboy Ventures, a seed-stage focused venture firm where she focuses on investing in the future of work and edtech companies. Prior to Cowboy, she spent nearly 3 years as an investor at Emerson Collective. As an early hire on the investing team, she played an important role in building key investment theses, creating internal processes, and helping to grow the team. During her time there, she led the firm’s investments in companies like Handshake and Career Karma. Before Emerson Collective, she worked at BloomBoard, an early-stage education technology company, where she focused on customer success and sales.

Episode transcription:

[00:00:25] Jomayra Herrera: Hi, I am Jomayra Herrera. I am a Principal at Cowboy Ventures, and we are a seed stage focused fund based in the Bay area.

[00:00:33] Jahn Karsybaev: Jomayra, thanks so much for finding time joining us on the podcast this afternoon. You're joining us from Orlando, right?

[00:00:40] Jomayra Herrera: That's correct. Sunny Florida.

[00:00:42] Jahn Karsybaev: Awesome. Yeah, we'll be serious, South Florida. Tell us a little bit more about yourself, your background. And then I want to spend some time talking about where you currently wake you up.

[00:00:53] Jomayra Herrera: Yeah, of course. Well, I suppose my background actually starts here in Orlando, Florida. It's a little bit full circle. I was born and raised in Orlando. And as you can imagine, especially when I was born, there was no conversation around tech venture capital or startups where I was, but I was lucky enough. I was the first in my family to go to college and I was lucky enough to go to school in the West Coast, in the Bay area. And through that experience, as someone that was going to be first in her family to go to college, I was like, okay, I'm going to be a doctor, a lawyer, an engineer.

It has to be one of the three. I know nothing about science or math. And so I was like, lawyer. I also enjoy arguing, so it felt like a good fit, and so I did everything you're supposed to do to get prepared for and go to law school. I did the internships. I prepared for the LSAT and when the morning of the ALSAC came, I just realized that when I thought about where I was spending my time, it was never really thinking about being a lawyer or I didn't really have any passion around that career. When I thought about where I was spending my time, it was always in schools, working with kids, and primarily K-12 schools. And I promise I will get to the point of how I ended up becoming an investor, but I realized that what I cared deeply about was economic mobility and education.

[00:02:16] And so I ended up going to graduate school for education, and during that time period, I really focused on adult learning and really childhood learning and just fell in love with the idea and the mission of reducing inequities for people all across the board. And after graduate school, I started my career on the operating side, selling software to school districts. And anyone that has done that knows that it is very challenging. You learn a lot, you learn a lot about how to hustle, and you learn a lot about what not to do. but I really enjoyed that experience. And one of our angel investors happened to be Steve Jobs’ widow Laurene Powell-Jobs, through her family office, Emerson Collective.

And so through that relationship, I just got to know the organization better. And then I ended up joining their first investing hire, I didn't know anything about venture capital other than having worked at a venture backed startup, but I learned a lot on the job. And we went from effectively, like a very, very small team of just a few people to about 20 investors.

[00:03:19] By the time that I left and we became a multi-asset family office, and just by nature of my background, I spent a lot of time investing in education and future work-related companies. And I know like the story's not rambling, but I'm almo