Stewart, Thione: LGBTQ Founders and VCs

25 minutes, 4 links


Updated February 11, 2023
Better Venture

Gary Stewart (Techstars, FounderTribes)

Lorenzo Thione (Gaingels, StartOut)

Gary Stewart, the founder of FounderTribes, and Lorenzo Thione, co-founder of StartOut and now managing director of Gaingels, spoke to us about their experience being gay in the world of tech and investing. The bottom line: it really matters where you are (the UK is less networked than Spain or the US) and whether you find your safe group that allows you to be yourself at all times. Holding together really helps—and will eventually allow you to spread the privileges you and your group have achieved.

Interviewed January 2021

LGBTQ Communities in Different Countries and in Tech

Erika Brodnock (EB): You’ve both worked in the tech ecosystem in various roles as founders and investors—how has the experience of being part of the LGBTQ+ community in tech evolved during that time?

Lorenzo Thione (LT): There would be so much for me to say primarily, not just because I’ve lived my own identity as LGBT and as an entrepreneur, but also because I’ve really worked to affect and to improve the dynamics of how LGBTQ and entrepreneurship as identities meet. When I started my first company, I had just come out maybe two or three years prior to that. It wasn’t so much on my mind at the time, but I perceived it being an obstacle for a lot of other people who I knew and who were not out to their boards or to their investors or within their companies. It has certainly impacted me to think about why that was. Especially in places like San Francisco, which were extremely open and accepting, there was a dynamic that was characterized by the feeling of not knowing what you had to gain from coming out. I saw the myopic approach in that, I thought there was so much to be gained by not constantly looking over your shoulder and worrying. Not only that, but there’s also something to be gained for everybody else, because you’re all of a sudden becoming a visible, real role model; you show through representation what’s possible, what jobs and professions are possible. The value of representation is so, so important. We know this from entertainment, we know it in so many different circumstances. That was largely why I cofounded this non-profit, StartOut, shortly after the exit from my first company. StartOut is very much focused around creating not just a safe space, but also an edge, something to gain. For people to understand that the moment that they did come out and embrace their own LGBT identity and entrepreneurial identity together, they had a community to rely on, they had resources to rely on, they had a shared experience and a shared background.

Gary Stewart (GS): I’ve been gay in three different countries. I think being gay in New York in the 1990s was just really scary. It was at the height of the HIV/AIDS moment. America was a very homophobic country. Being at Yale Law School, in the 1990s, I studied a lot about sexuality, but I was nervous about it; I was afraid to even be associated with homosexuality in any case. At the time, it was still technically illegal for gay men to have homosexual sex. I mean, sodomy was illegal in a lot of states and the Supreme Court had ruled that such discrimination did not violate the US Constitution. So that was America. It was a large part of the reason why I left. I didn’t feel it was a place where I would ever be allowed to be myself; if you are gay and can choose where to live, you might not have chosen America in the 1990s. And especially being a Black Jamaican man, there were additional pressures and discrimination to deal with.

When I first moved to Barcelona, Spain, and my friends came to visit, they called it “Gaycelona.” Gay men were holding hands and kissing in the streets, which was really weird and transgressive to me. I quickly found a gay mentor, who still is one of my best friends. Everybody was just so open and accepting. And that explains probably why I lived in Spain for 14 years, because maybe from an economic point of view, it wasn’t the best place. But it was where I felt like I belonged, without judgment. Spain was really, really free and accepting. Even when I went to work for a business school run by old-world Spanish aristocrats, it was very welcoming. The dean was openly gay. And when I left Barcelona to go to work at a big telco called Telefonica where everyone looked like they came out of a Polo ad, I was worried. Everyone kept saying how they would be super Catholic—and yes, people were super Catholic, but they were still really accepting of me. On the whole, it didn’t really seem to be an obstacle, being gay in Spain.

Unlock expert knowledge.
Learn in depth. Get instant, lifetime access to the entire book. Plus online resources and future updates.

When I came to the UK, I thought, whereas in Spain homosexuality was really embraced and discussed, in the UK it didn’t really feel like it was something that was as visible. In the tech scene, I saw people starting to try and create “gay in tech” organizations, and I’d try to support them. But it just doesn’t seem like a gay movement exists in tech like it might in Spain or in the US. When it comes to lots of elements of personal identity, it seems like the UK prefers to pretend that a lot of things don’t exist and keep it moving. Whereas I feel identity politics seems to be part and parcel of being American. And definitely not something that Spanish people shy away from either.

The Importance of Representation at Every Level of VC

Johannes Lenhard (JL): Lorenzo, how and why did you become involved in Gaingels?

LT: So I should be precise that I did not found Gaingels; I was on the board of StartOut with my friend, David, who started Gaingels with Paul in 2015–2016. I was busy with writing and producing a musical that would go to Broadway, as well as a new social media company I had founded. Back then they came to me and basically said, “Look, we want to create a group for LGBT investors to invest in LGBT entrepreneurs.” At the time, that was definitely missing from the equation. I made it clear that I couldn’t do it with them but that I would be a big cheerleader and supporter. And then a time came when things had shifted a little, in 2018. My personal situation had shifted, the show had closed, my social media company was largely on autopilot; I could basically focus on other things. We started talking about the fact that there was more that could be impactful in the ecosystem and that could have a positive effect for social change, rather than only focusing on a narrow view of diversity when it came to LGBT leadership. We talked about how important it is to go beyond the founders, to address also the C suite, the boardroom, all the other layers in the venture ecosystem where decisions and value intersect. We started to focus on making sure Gaingels could add value beyond investing—we developed a recruitment tool and established an internal practice for our companies to help them identify great board members that come from diverse backgrounds, including LGBT.

Building a diverse investing ecosystem means also to address the issue of who is benefiting financially from the value that is being created in the ecosystem. If you looked at how this was decades (or even just a few years) ago, both decision power as well as the wealth value would remain within insular groups largely made of people that all looked the same and came from the same socioeconomic backgrounds and the same educational and financial circles. Bringing more diverse investors, investing in more diverse teams, pushing the conversation into valuing diversity and inclusions across all axes, all this can only happen once you’re at the table. So we focused on delivering value, and creating access opportunities, and over time Gaingels really evolved into what it is now, a venture investment syndicate made of thousands of individual investors who index very high across many diversity axes, that are able, collectively, to back and invest in companies that embrace diverse leadership at all stages of growth. This is because of our collective commitment, the value we deliver, and the fact that we bring and represent the LGBTQ community and its allies on the venture cap table, to help push forward the conversation on why inclusion and representation is important, even in venture. In the last three years, we went from an angel group that had invested $3M or $4M across a couple of years to having invested almost $150M in the three years since.

Making Your Own Room to Grow Professionally

EB: Gary, what made you start FounderTribes? Was there a particular moment or incident that made you decide to leave your career behind at Telefonica?

GS: What I found is Spain was really great for me, because I was an American first and Black second; like that, America is great, because as long as you are good at what you do, there’s a way, and they really prioritize and love winners of all colors, even though it might be a little bit more difficult to win if you’re Black, or gay, or both. Then I found in the UK that it’s a societal system that’s the most stultified; it’s like you’re fighting against almost 1,000 years of dynastic history. It’s not as fluid as say, Spain, which is ultra-liberal after shedding Franco in the 1970s, or the US, which is still a relatively young country. In the UK, everything is a bit more rigid. So long story short, I found that in Europe, and in the UK in particular, there wasn’t really room for me to grow professionally, unless I was willing to create something myself. Certain doors would be closed to me, because in many ways I am a perpetual outsider who is allowed in to visit but never really welcomed to stick around indefinitely, at least not at the level that would match my ambitions. The reason that I created FounderTribes was to see if I could do something about this.

In 2021, it can’t be that we still live in a system that rejects 99% of would-be founders in no small part because of race, gender, and other considerations that should be irrelevant in this context. And it’s not just about race; particularly in the UK, it’s also about class and geography. There are just so many different reasons why people are locked out of the system. Entrepreneurship is not exempt from the rules of society at large, which still privileges upper-middle-class white men who went to certain schools and are based in London. We can’t sit around for another 10 years talking about how 1% of founders in the US that get funding are Black or 2% are women, or that in the UK, those numbers are 0.24% for Black founders and not much better for women. I don’t even know what percentage are gay. I wanted to use technology to focus on this problem, to give more people access to the feedback, networks, and capital that they need to start up and scale up their businesses, all from a mobile phone.

The Work Is Never Done: LGBTQ Accessibility and Intersectionality

JL: Where do you think the accessibility for LGBTQ folks is not yet given? Where is the ecosystem particularly closed? And where do we still need to work harder?

LT: So, there are two really important dimensions to take into consideration there. But one is obvious: geography. It’s not the same everywhere, even within a certain country. Obviously, San Francisco and New York are very different realities than rural America and the South, or even the Midwest. There are still a lot of discriminatory laws in place in states that are just simply not as open. But the other dimension to look at is intersectionality. While things may have gotten better in many areas for gay white men, the issues are compounded for LGBT women, for BIPOC LGBT folx, and especially for trans individuals. I would say that the reality is that for trans men and women in the workforce, as employees in a tech company or a VC, we are in an absolute way much farther behind then where we gay men were 15 or 20 years ago. Issues range from open discrimination to constant microaggression and unconscious bias. The reality is—and the shortest way to say this is—the work is never done. We have to take some of the progress and the privilege that derives from say, even for someone who’s a member of the LGBT community, being male and white, and use it to advance the state of things for many others. How do I leverage that power to help create more equity, both through representation so that it becomes normal and through more direct access and opportunities, for anybody else that is not yet at the same sort of place in that forward movement as we are?

EB: On two occasions now, Lorenzo, you’ve said that this isn’t just about the LGBTQ community, it is about making sure that the door is open for everybody that needs to come through it, which is commendable, and in my opinion, the true definition of allyship. Gary, do you want to answer that question as well?

GS: Before I get to intersectionality. I still feel that for me, being gay still needs to be focused upon. These two parts of my identity, being Black and being gay, present themselves differently. Being Black is something that I can’t really avoid—everyone knows it. So I have to deal with that element of my identity always. Whereas being gay, you can hide it. The struggle is different, precisely because it can be hidden. So for instance in the UK, I don’t see that many other openly gay entrepreneurs and I believe many of them might not be out of the closet. And that makes me ask the question, in this day and age, why are people still afraid to come out? And so as much as I think the intersectional bit is important, I think it’s also important to still remember that just because gay people can now marry and there are gay characters on TV, it doesn’t mean that anti-gay prejudice has magically disappeared. There’s still lots of things that gay people can’t do. Up until recently, gay people couldn’t even donate blood, or at least it was treated with suspicion, because of the AIDS crisis. Gay people can’t really have kids the same way, and in the UK, I still don’t think you see so many public displays of affection between gay people. I also have a transsexual friend, and I have to say, her struggle is real. Just because people watch Pose doesn’t mean that they don’t have issues with transgender or transsexual women, for example.

Dealing With—and Debunking—Presumptions and Prejudices

EB: To focus slightly more on your intersectional identity, has either being Black or being gay ever hampered any of your progress?

GS: Definitely! Like I said, being Black is different, because I can’t hide it. People won’t always say what they think about it to my face. Being Black in the UK is a really interesting experience, in the sense that even though I’m not from here, there are certain presumptions that I can’t seem to overcome. I just wasn’t born into the right family. My last name could be an “acceptable” last name if I weren’t Black. That is heavily tied to race, but not limited to it. I think that’s also about class. Maybe that’s why Meghan Markle felt a little bit uncomfortable as an American here. Whereas I think being gay has been less of a factor. I can choose when I want to share it, and I must admit that I don’t always choose to share it.

EB: Lorenzo, what are your thoughts on this—has your sexuality ever been a superpower for you in any way?

LT: First of all, it’s somewhat easy to affirm that my identity as a gay entrepreneur has had an impact on both my choices and my outcome, since it’s what makes me who I am, but it’s hard to say whether or not it has made things necessarily better or worse. It definitely has carved a path, and I’ve chosen to walk one set of choices and one set of things that I’ve leveraged that way, that would not have been the same if I hadn’t been gay. Any ingroup/outgroup dynamic—whether it is about sexual orientation or ethnicity or being a Stanford grad—can be helpful and leveraged for advantage, however. It is not something that is specific to either race or sexual orientation, I can guarantee you that for Stanford graduates, it’s easier for them to raise money from Stanford graduates. You leverage the shared identity and experience with an ingroup to create more affinity to leverage the fact that they have a vested interest in your success just by virtue of association.

The impact, though, can be certainly negative for people who have to deal with individuals, because of their work or because of where they live, who have prejudices against them. I don’t believe that has happened to me specifically. But I’ve also really tried to create visibility for my own successes and for the things that I was doing, so that it would both help others to see what’s possible, as well as debunk the prejudices that may be holding back certain groups of people. I often tell the story of having dealt with a college roommate who came from a very conservative family. I wasn’t out when I first lived with him. He was a little younger, and I was doing really well academically and had certain successes that clearly created a certain positive relationship. When I came out to him, which was not easy, it broke down all of the things that his family or his background had created for him: “Wait, wait, wait a second. This is a person who I know, who I respect, who I admire, who I want to emulate in so many other ways; how is this the same person as what I’ve been told that a gay person is going to do or represent in society?” And whereas that might be a very specific example, I really believe that creating mold breaking examples and stories where you show people what’s possible has both a positive impact within the group, because it creates representation and visibility for them to see what they can do, but also outside the group, debunking and breaking down prejudices. It’s the same rhetoric that can bolster the acceptance of immigrants in a lot of groups where immigration is seen as something that conservative movements have depicted as leech-like or taking and not giving, it breaks down that narrative by showing what success and what positive impact to society immigrants can have.

Advice on Being Open about Sexuality in Tech and VC

JL: Let’s touch on how to best navigate the tech and VC ecosystem when it comes to being open with your sexuality. What would you tell people now? What is the best takeaway that you’ve learned that you can share?

GS: My best tip is definitely to find your tribe. I always like to have a group where I feel really safe. At my last job, for instance, there was a group of us who were early-stage investors and we were all gay, some out of the closet, some a bit more closeted. We spent a lot of time together, hanging out, and having all those conversations that normally you can’t have when you’re in mixed communities, because you’re worried about being “too gay” or whatever. It is good to have that community where you have that safe space, and then just navigate it the best that you can; you don’t have to be out with everybody if you don’t want to be.

LT: So I think it’s very similar to what Gary said, but let me focus directly on the relationships; so if we’re thinking, for example, about entrepreneurs navigating the world of VC, which largely means looking for investors, employees, or partners. That is quite similar to dating; if you were to date someone and go on a few dates but you felt like you had to hide all of these things about yourself, most likely, that’s not going to be a relationship that’s going to work out. I see it similarly for the entrepreneurs now; there are enough groups that are dedicated to removing a lot of the specific barriers you might face and connect you with other like-minded people. It helps if you weed out the people that you might not want to be in business with, specifically not for a long relationship between an entrepreneur and an investor. I say, find your tribe. If the venture partner that you might want to take a big investment from really has a problem with you being gay, guess what: you do not want them to find out at a later point after they’ve signed that check.

If you found this post worthwhile, please share!