So Excited to Have Haley Bryant on Board!
Meet Citrine's first Investor in Residence!, Haley Bryant! Haley has invested in 60+ companies over six years—including four unicorns. She’s bringing her experience, perspective, and investor network to our community. We’re looking forward to learning, connecting, and growing together with Haley.
Haley, so great to have you here with Citrine! As Citrine's first Investor in Residence, what are you most excited to contribute to the women in our community?
I’m excited to shine a light on the work that Citrine is already doing, and to bring more deals to the community. I’ve been lucky to meet so many investors at Seed and Series A over the years who will be excited to learn about and collaborate with Citrine!
What first sparked your interest in investing and finance?
I learned a lot as a COO, running the P&L of a bootstrapped content marketing agency. Many of our customers were high growth early stage startups, but I thought investing was for VCs in Patagonia vests who'd spent their whole careers in banking, PE or consulting. The more time I spent reading and meeting people through X, LinkedIn and in person, the more I realized there are many paths into investing. Having a different path meant seeing opportunity in markets others might overlook. That was the seed of my angel thesis when I started in 2020.
What do you think female investors bring to the table that is sometimes overlooked in traditional investing environments?
Sallie Krawcheck once said, "When you go to people who have your view of the world and you ask them for money, it works." She was one of the most powerful women on Wall Street, but had a hard time finding like minded investors who saw the opportunity to close the gender wealth gap. She stayed committed to her vision, and by working with mission aligned funds and angel investor communities, built a $53M Series B cap table that was 90% women and underrepresented investors. Sallie understood that women aren't risk averse, we're risk aware: we dig deeper before writing a check, and we ask the questions that make founders think about the second order impact of what they're building.
You can see the same pattern in who's actually catching what AI hyperscaling misses. Joy Buolamwini found that facial recognition failed worse on darker skinned women than on anyone else, and built the Algorithmic Justice League around that finding. Timnit Gebru raised the alarm on scaling language models without asking who gets left out, and started her own research institute when Google wouldn't let her keep asking. That's not because women are inherently more careful. It's that the people who get hurt by what a hyperscaled product misses are usually the first ones to go build the fix.
If you could give one piece of advice to a woman who is considering making her first angel investment, what would you tell her?
Think in bets, and be patient capital. What has to go right for this company to succeed, and on what time horizon? Most companies fail, so size the bet knowing it's not about any one company, it's about getting exposure to enough of them that could return your capital and multiply it. I've angel invested in 60+ companies over the last 6 years. Many have wound down, been acquihired or are still in an exploratory wilderness period. Four are unicorns. The J Curve shows you your losers before your winners start to emerge, and even then it’s hard to know how big your winners will be. You won't be right most of the time. But write down your assumptions so you can learn along the way, and write the next check with a little more perspective.
Beyond writing a check, what do you believe is the most valuable thing an investor can offer an entrepreneur?
When you start a company, you have very little; yourself and a dream. And pretty quickly, the world will tell you why that dream can’t exist; investors will say no. Customers won’t materialize. Team members will quit. Investors who can offer a safe space to share, remember the dream, and actionable encouragement are invaluable.
What’s something you’ve tried recently for the first time?
One of my favorite parts of being a mom is getting to follow my son’s curiosity. This summer, we went railbiking in Frostburg, tried glass fusing at the Corning Museum of Glass on a roadtrip to Niagara, and we went kayaking in Cape Cod. I’d welcome funtivity ideas!