Profiles in Awesome: Hillary Strobel

I'm continually inspired by the dope, brilliant women who have shaped and inspired my career, so as a special shout out to them, I'm dedicating my next few blogs to sharing their stories with my network. If you enjoy this blog, have been inspired by my story, or enjoy the work I do, you can bet they had a hand in helping me get to where I am today. I'm so grateful to have crossed paths with these folks and I'm excited for you to get to know them a little better. First up is Hillary Strobel. She's the President & CEO of the Flyways, and impact investing firm based in Portland, OR. She's also a mom and one of my very first entrepreneurial mentors. 


Louisa Shepherd: Hi Hillary! Let’s start with the basics. Can you tell us a little bit about who you are and what you do?

Hillary Strobel: Yes! Hi Louisa! You know I love you. As you also know, I'm a single mom, which is the best thing I've ever done in my whole life, and I lead a registered Benefit Corporation [this is a legal designation in the state of Louisiana, not to be confused with being a “certified B Corp,” which is a branding tool offered by B Labs] called The Flyways. We create, develop, and support positive social impact companies, through a combination of patient capital and impact investing. Our vision is to help create a just and dignified economy.

LS: Tell me about the Flyways. Where did the inspiration come from and how has it evolved into the company it is today?

HS: The name comes from ecology. A flyway is the term used to describe the pathways and supporting species of birds as they migrate for the seasons. In a flyway, the bird is the capstone species, but all of the players--trees, food sources, water sources, humans, etc-- must be integrated and balanced in order to support that bird. When the company was hatched (pun intended), I had been living and working in New Orleans, which is at the very southern end of the Mississippi Valley Flyway, in various reforestation and social justice efforts. One fall, I was sitting in the park watching some flocks fly south for the winter. I thought about how crucial it was for them to have the habitat in that area restored, because from Louisiana, they must fly over the Gulf of Mexico to get to the Yucatán peninsula. The more the Louisiana coastline recedes, the harder it is for those birds to survive the flight. What better metaphor for contributing to the supporting economic systems that give flight to social justice and positive social business communities? Over time, this idea has grown from watching those birds to a multi-million dollar investment business. We accomplished this through a creative approach: online collaboration tools, a willingness to be both open to change and true to the vision, empathy and a little more empathy on top, and an unwavering commitment to justice.

LS: What did you do before becoming an entrepreneur? What lead you to step out on your own?

HS: I've always been entrepreneurial. I was raised by a small business owner, who created local jobs, kept the work personal, and never stopped striving for excellence. As a result, I demand greatness from myself. I never felt challenged to meet that in myself from some of the work-a-day jobs I had. They were just things I did because I needed the money at the time. But we know that money all by itself isn't enough of a motivation, right? I had all the jobs a young person straight out of college with a Humanities degree is supposed to have--waitress, bartender, retail (and those are the types jobs that are really rife with sexual harassment, which I experienced A LOT)--but I always came back to social justice somehow. So mixed in there were some non-profit gigs and consulting with environmental organizations. Each of those jobs taught me something about a certain skill set or professional behavior, how to deal with setbacks and disappointment, how to defend my spiritual and physical self from untoward behavior, and how to build a business that actually works for the people who are part of it. Over time, as I worked up to more substantial jobs and partnerships (which also taught me about leadership), I met all the folks who could and would support this impact investing idea, and so here we are. Mind you, what I just described took over 20 years, the last 5 with The Flyways, to achieve so it goes to show that there's NEVER a need to impose a standard of “making it” by a certain age or in comparison to anyone else.

LS: Why do you focus on women and women owned businesses? How do you hope to make an impact in this area, and why is it such an important focus for the company?

HS: Great question! It's clear, and getting clearer by the day, that the future is female. This goes for business too. I want to quote the good women of the feminist business school, if I may: “We see entrepreneurship as a site of personal power, radical creativity, and meaningful social change. We exalt in integration and embodiment as we quest to build companies in harmony with our bodies, Earth, our communities, and our deeply held beliefs.” Powerful stuff! If there are women out there who are creating businesses with this as an operating (wo)manifesto, then I want to invest in them. Of course, it goes without saying that the female economy is a huge money-maker. But again, money can't be the only motivating factor! There has to be actual meaning, and nurturing meaning is something that women excel at. When we're at equity in the economy with men, these kinds of changes can, and will, benefit everyone. I want to take those oft-quoted numbers--for example, women participating equally to men in the economy can contribute $25 TRILLION to global GDP over the next 10 years--and give them feeling. What is that $25T contributing to our kids? Our food and water supplies? Our humanity? Our homes and planet?

LS: Have you had to overcome any challenges as a female entrepreneur? Is there anything you wish you knew before getting started?

HS: I was very lucky to have a female thesis advisor when I was in grad school who always told me to be true to me and not to stress about “coulda, shoulda, woulda.” Has that ever come in handy! The series of moments that crystallized the start of this company were at the last “job” I had, where the fellow in charge gave ample opportunities to learn how not to treat a team of employees. It would have been wonderful to have never experienced that, but then again, I wouldn't take away anything that made me who I am. I wish I’d had more allies as I was going through that time period, and so I've worked hard since then to make sure to surround myself with loving, supportive folks, such as yourself! So far, the most prevalent kind of female entrepreneur-related stress has come from well-intentioned men who think I don't know anything about investing or leadership, and take it upon themselves to explain what I might want to do about this or that. And I'd tell younger me to never stop getting educated about all sorts of stuff, because you never know when things find synthesis. The good news is, I haven't stopped getting educated! Life is for learning.

LS: What’s it like running a company and being a mom? How do you balance it all?

HS: This is crucial: my work and my motherhood are not two distinct things that I feel I must keep separate in order to find equivalence. I don't strive for “balance,” I strive for harmony. My daughter is involved in my business relationships, my thought process about investing in the future of the economy, and how I see myself leading a team of people to accomplish that. For example, Eva has been sitting next to me and playing while I work on this interview with you, and when she needs my attention, she gets it. Being a parent has also inspired me to create a company that has a pretty forward-thinking family leave and health care package for the team--we give three months a year for maternity and paternity leave, for example--and a culture of treating the team and our investees as a family in which we all have intrinsic value. Of course it's harder when my daughter is sick or needs me right in the middle of a meeting, but everyone has been so patient and generous. I've come to believe that this dignified economy won't require us to compartmentalize our lives in this way; it'll be natural to breastfeed at our work stations or for a new dad to stay at home with his baby.

LS: What’s your favorite part of running the Flyways? What are your biggest challenges?

HS: My favorite part of running The Flyways could be another blog all by itself. Simple answer: everything! I love everything about it. The challenges, I think I've touched on here and there: well-meaning mansplaining, an occasionally sick child, wishing there were more hours in the day to fit in all the possibilities for enchantment.

LS: What do you look forward to most when you think about your company and the impact that it will make on Women?

HS: I look forward to nothing less than a dignified way of doing economy. I look forward to justice. I look forward to the day when my daughter and all daughters and sons have equal chances for opportunity. I think giving women this opportunity will shift global consciousness: imagine knowing that humanity can not just survive but thrive. It's all right here, just waiting to be unleashed.

LS: How can we learn more/get involved/stay up to date on the flyways?

HS: We are always looking for people who would like to bring their assets to us to invest in this glorious and all-together possible future. If someone has a great business pitch, we want to hear it! We're also on all of the usual social media suspects, including Medium, where I try to post regularly about topics related to the dignified economy. And of course, there's our website at