In Conversation: Gary Stewart and Lorenzo Thione

Two investor/entrepreneurs talk openly about being gay in tech, intersectionality, finding community, and the power of honest relationships.
Erika Brodnock
Johannes Lenhard
Gary Stewart
Lorenzo Thione
▪︎ 26 minutes read time
stewart-thione

Erika Brodnock and Johannes Lenhard are the authors of Better Venture, a first-of-its-kind guide to diversity and inclusion in venture capital and startups—who funds, who gets funded, why that needs to change, and how to make it happen. Gary Stewart, the founder and CEO of FounderTribes, and Lorenzo Thione, co-founder of StartOut and now managing director of the LGBTQ+ investors’ group Gaingels, spoke to Johannes and Erika about their experience as gay men in the tech and investing world. The bottom line: it really matters where you are (the UK is less networked than Spain or the US) and whether you found a safe community to be yourself within the larger founder-funder ecosystem. Holding together really helps—and will eventually allow you to spread your achievements to others.

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 LGBTQ+ and as 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. It wasn’t so much on my mind at the time, but I perceived it being an obstacle for a lot of other people I knew 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 that 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. There is 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 real, visible role model; by representation, you show what’s possible, what jobs and professions are possible for others like you. Representation is so, so important. We know this from entertainment, we know it in so many different circumstances.

That was largely why I cofounded StartOut, as a nonprofit, shortly after the exit from my first company. StartOut is very much focused on creating not just a safe space, but also an edge, something to gain, and for people to understand that the moment that choose to come out and embrace their own LGBTQ+ identity and entrepreneurial identity together, they have a community to rely on, they have resources to rely on, they have a shared experience and a shared background.

Johannes Lenhard (JL): Gary, do you want to say a little bit about how it was for you over the last decade or so?

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 U.S. 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 with 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.

When I came to the U.K., I thought, whereas in Spain homosexuality was really embraced and discussed, in the U.K. it didn’t really feel like it was something that was very 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 U.S. When it comes to lots of elements of personal identity, it seems like the U.K. 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.

JL: Lorenzo, tell us about the story behind Gaingels.

LT: I was on the board of StartOut with my friend David [Beatty], who started Gaingels with Paul [Grossinger] in 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 LGBTQ+ investors to invest in LGBTQ+ 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 auto pilot; 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, than only focusing on a narrow view of diversity when it came to LGBTQ+ leadership.

We talked about how important it is to go beyond the founders to address 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 the LGBTQ+ community.

Building a diverse investing ecosystem means also addressing 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 who 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 inclusion 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 and who 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 $3 or $4 million over a couple of years to having invested almost $150 million dollars in the three years since.

EB: A fantastic step indeed. 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 U.K. 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 Spain, which is ultra-liberal after shedding Franco in the 1970s, or the U.S., 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 U.K. 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 is 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 U.K., 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 U.S. that get funding are Black or 2% are women, or that in the U.K., 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.

JL: Where do you think the accessibility for LGBTQ+ folx 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 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 LGBTQ+ women, for BIPOC LGBTQ+ 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 VC firm, 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 is this—the work is never done. We have to take some of the progress and the privilege that it derives from—even for someone who’s a member of the LGBTQ+ 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 who is not yet at the same sort of place in that forward movement as we are.

EB: I love how you explain 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. That’s commendable, and in my opinion, the true definition of allyship. Gary, do you want to answer that question as well and perhaps talk about intersectionality, too?

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 U.K., 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 because of the legacy of the AIDS crisis. Gay people can’t really have kids the same way and in the U.K., 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.

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 U.K. 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, I don’t always choose to share it.

LT: It’s somewhat easy to affirm that my identity as a gay entrepreneur has had an impact on both my choices and my outcome—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 in-group/out-group 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, either. I can guarantee you that Stanford graduates, it’s easier for them to raise money from Stanford graduates. You leverage the shared identity and experience with an in-group 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 in their work or 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 that I grew up being told is going to do or represent certain negative things in society?” And whereas that might be a very specific example, I really believe that 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 debunking and breaking down prejudices outside the group. It’s the same rhetoric that can bolster the acceptance of immigrants in conservative groups that have depicted immigrants as leech-like or taking and not giving, stories of success break down that narrative by showing what positive impacts to society immigrants can have.

JL: What would you tell people now who are navigating the tech and VC ecosystem as gay, lesbian, trans, bisexual, or queer people? 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: I think it’s very similar to what Gary said, but let me focus directly on the relationships. 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 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. 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.

I say, find your tribe.

With data, history, and interviews with investors and founders, Better Venture demonstrates the needs—both moral and monetary—for a more diverse and equitable funding system in the U.S. and U.K., and across Europe. To support the creation of this book and be the first to know about new interviews and special offers, sign up for the waitlist or pre-order the book today.

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