Antonia Dean’s career has been built on baby steps — each move bringing her closer to her true passion: helping startups succeed.
Based in Cheltenham, Pennsylvania, Dean is a partner at seed-stage venture firm Black Operator Ventures. Her time at Venture for America and Comcast, building programming that supported local startups, taught her that what she really wanted to do was invest in these companies.
Today, Dean uses her role to give money to companies that others may not see the opportunity in, Dean told Technical.ly.
Before that, Dean first went to law school and worked in the cosmetics industry. Neither excited her as much as the problem-solving nature of the startup world.
“I started showing up to things where investors were, even if I wasn’t an investor. I started really leaning in on every opportunity that got me closer to dealmaking.”
Antonia Dean, partner at Black Operator Ventures
While it was a big leap, she learned that there’s never a right time to make a career pivot. When you want to make a change, you have to slowly start pursuing it, she said.
“Opportunity meets you when you’re doing the thing, not when you’re waiting to do the thing,” Dean said.
In this edition of How I Got Here, Dean shares her journey to the startup world and her advice for people looking to shift their careers in a new direction.
Where did your interest in startups come from?
I went to undergrad at Florida A&M University in Tallahassee and then I went straight through to Harvard Law School. I realized about two-thirds of the way through that degree that I did not want to be an attorney. I graduated with my law degree and went into the cosmetics industry as a cosmetics brand manager.
I was working for the Estée Lauder Company, and I was in the new ventures group. Essentially, it was my job to come up with new brand concepts and launch new startup brands from within the company.
That’s where I really got bit by that startup bug. I kept being told, “Act like a startup, think like a startup, don’t do it the old way.” I wanted to do more of that and so I left the cosmetics industry to get into startups.
After that realization, how did you enter the startup world?
I went to a startup nonprofit called Venture for America, which was helping recent college graduates get jobs at startups, understand what it takes to be an entrepreneur, and then, when they were ready, we were giving them grant dollars to be able to start companies.
I helped that org raise its first venture fund and that is where I really realized, “Oh, this is what I like.”
I moved back to Philly and worked at a private equity firm called Archetype, and from there, I got recruited to join Comcast in their startup engagement team, working across LIFT Labs and a couple of other programs. There I was doing both direct investing in the startups, managing a few funds and doing pipeline development.
But I really wanted to do more direct investing. I connected with my current partners and made the move to Black Operator Ventures about three years ago.
What do you enjoy about your current role?
This point in my career brings so many disparate experiences together.
It combines being a profit and loss leader, being the person who’s launching the product and some of the strategic work that I’ve done in terms of thinking broadly about where opportunity lives.
The role even actually combines my background as a lawyer, frequently being able to draft the terms of these deals and understand exactly how what set of terms gives us the best potential return on our investment.
The best part of my job is talking to founders, hearing their pitches, helping them refine their go-to-market or business model and helping them probe and think differently about their initial idea and where the real potential may lie.
How challenging was it making the move to full-time investing?
I realized in late 2018 or early 2019 that what I wanted to do was invest full-time, and it took a good number of years to make that a reality. COVID shook everything up about a year into that journey, but I also realized that sometimes people will not necessarily see the potential in you.
There are always situations where you can be like, I know I can do this thing. I just need someone to give me the shot. You can sit and wait for somebody to give you the shot, or you can just go start doing things.
So, I started showing up to things where investors were, even if I wasn’t an investor. I started really leaning in on every opportunity that got me closer to dealmaking, like talking to more founders and hearing pitches from people on the side.
When I was at Comcast, I got to do one or two deals a year, but I leaned so hard into doing those deals and making sure that they were the absolute strongest.
How do you know when you’re ready to jump into the next role?
The moment you start thinking, “that looks cool, I kind of want to do that,” is the sign that you’re ready. Ready doesn’t exist. You have the idea and then you just jump.
If you’re really into startups, but maybe you’re not in a position to take that kind of risk, and you don’t want to leave your corporate job, start working for them on the side.
I’m not saying, quit your job, sell all your furniture. But if you see someone doing something, and you’re like, “That’s really interesting. I’ve never thought of doing that,” I promise, there is a way that you can start to do something with it.
What advice do you have for people who are starting their investing careers?
For someone who is at the start of their career, always understand what your role contributes to the overall company. You’re either helping to bring in customers or you’re helping to operate the company and understanding where you fall will always help you be able to put your contributions in context.
For someone who’s interested in investing and becoming an investor, be very curious about the world around you and start to have your own personal investment thesis.
The more you are curious, the more you will start to see interplays and similarities and things that are occurring outside your target niche that have an influence on it. The deeper your bench of experience, the better deals that you will make.
