Most investors spend their lives trying to answer one question: how do you get access to great companies early?
Lorenzo Thione somehow answered a harder one: how do you do it 2,700 times—without turning your operation into a flaming spreadsheet monster—and still have time to produce Broadway shows?
In this episode of Ignite VC, Lorenzo (Managing Director at Gaingels) sits down with Brian Bell to unpack how Gaingels scaled into one of the world’s most active venture syndicates—now spanning ~2,700 portfolio companies and $1B+ in invested capital—and why the organization’s “inclusive investing” mission is not a side quest, but part of the engine.
If you’re not listening to the full episode, here’s the story, the strategy, and the playbook—minus the podcast banter (but with a little of the energy).
The bigger pattern: scale doesn’t come from hustle—it comes from systems that compound.
A lot of venture sounds like: “We have great taste.”
Gaingels sounds more like: “We built a machine where good opportunities and good people keep colliding… on purpose.”
And that’s the throughline of Lorenzo’s entire life:
He helped build a computationally intense AI search company so early that Amazon essentially called them up and said, “Hey… want to try this thing we’re calling EC2?” (Yes, that EC2.)
The company was acquired by Microsoft and became part of the original story (and some of the underlying tech) behind Bing.
He helped build communities like StartOut to increase visibility and support for LGBTQ founders.
He wrote and produced a Broadway musical that took seven years of rewriting before it hit the big stage.
Same philosophy everywhere:
the nonlinear advantage comes from building flywheels—not just making bets.
Lorenzo’s origin story: early AI, early cloud, and the Bing prequel
Before “AI” became a daily buzzword, Lorenzo was building in the trenches of natural language + information retrieval—the kind of work that’s brutally compute-hungry.
PowerSet (his company) was so computationally demanding—before cloud was a normal thing—that it attracted investment connected to Bezos’s family office. Then came the surreal moment:
Amazon calls and says they’ve got excess infrastructure they might rent out. They want PowerSet as a test partner. They’re calling it Elastic Compute Cloud (EC2). Lorenzo believes they were among the first non-Amazon users.
Eventually, PowerSet was acquired by Microsoft, and Lorenzo describes Microsoft as seeing early that AI mattered for search. Their tech fed into the early story of what made Bing different—especially for informational queries (think Wikipedia-style intent).
The lesson isn’t “wow, cool résumé.” It’s this:
When you’re early, you don’t win by being right once. You win by building the infrastructure to keep being right.
Which is exactly how Gaingels thinks about venture.
What Gaingels actually is (and what it isn’t)
Gaingels isn’t trying to be your classic lead investor writing thesis memos in a candlelit library.
Lorenzo explains that Gaingels typically invests alongside other great investors rather than leading rounds. Their value is a mix of:
Capital aggregation (syndicating checks into rounds)
Talent + governance support (hiring, board recruitment, advisory networks)
Network effects across thousands of companies and investors
Over time, the network itself becomes the product: the introductions, the cross-portfolio opportunities, the investor connections—those become a flywheel.
In plain terms: Gaingels behaves like a VC platform more than a single VC brain.
The early Gaingels: a small club… with a problem
The first version of Gaingels started as something much more intimate: essentially a group of investors focused on backing founders from the LGBTQ community.
It was meaningful—and it came with a structural risk Lorenzo calls out in a very VC way:
If you artificially narrow the universe of opportunities too much, you risk losing information and losing “alpha.”
Not because the founders aren’t great—but because constrained sourcing can create blind spots, weaker deal flow, and fewer “network adjacencies” into the best rounds.
So Gaingels evolved.
Not by abandoning the mission, but by engineering a model that scales the mission.
The Gaingels evolution: from “fund overlooked founders” to “rewire who gets access”
Here’s the clever pivot Lorenzo describes:
If venture is heavily driven by networks—who you know, who you’ve worked with, who vouches for you—then exclusion happens even without explicit intent. That leads to predictable outcomes: women, LGBTQ founders, and founders of color getting disproportionately less funding.
Gaingels’ approach became:
Invite a highly diverse group of investors into the network
Invest in companies that value diverse leadership, talent, and capital
Help those companies execute on diversity goals (tools, board access programs, etc.)
Over time, create more diverse cap tables
When exits happen, liquidity flows into communities historically excluded from that wealth engine
Those communities reinvest—creating a compounding loop
This is inclusion as a flywheel, not a slogan.
It’s the VC equivalent of planting trees that drop seeds.
How do you operationally manage 2,700 investments?
At some point, “we’re a syndicate” becomes “we’re running a small financial-services company.”
Brian asks the obvious: How do you manage that complexity?
Lorenzo’s answer is refreshingly unsexy—and that’s why it’s real:
They didn’t wake up and decide to “build a platform.”
They crawled.
Early days: spreadsheets
Then: databases
Then: Airtable and automation
Then: an internal system that gradually became robust enough to handle serious scale
And here’s the key: they built it because, early on, third-party SPV infrastructure felt like it would eat too much of the already-thin economics. So they built their own rails, step by step.
That leads to the deeper point:
Scale isn’t a feature you buy. It’s a capability you grow—like muscle.
Why Gaingels runs much of its SPV infrastructure internally
This part gets nerdy in a good way.
They do use platforms like AngelList for some syndications, but a large portion is run on their own internal platform. The reason isn’t just cost—Lorenzo notes that efficient markets tend to push costs toward similar true-cost levels over time.
The reasons are more strategic:
Control over timing and quality of K-1s/tax reporting
Direct relationship with LPs (and better understanding of who they are)
Avoiding the “if you bring someone onto Platform X, they now enter everyone else’s ecosystem too” dynamic
Counterparty risk: he references the kind of mess that happens when SPV providers collapse and funds get stranded—meaning you’re suddenly cleaning up someone else’s operational disaster
Translation:
Gaingels prefers owning the pipes because reliability becomes a competitive advantage when you’re operating at scale.
“Okay, but why Broadway?” (Or: storytelling is the hidden operating system)
Then the episode veers into the most Lorenzo thing imaginable: theater.
He shares how, despite not having a theater background, he helped develop Allegiance—a musical connected to George Takei—through a seven-year writing and rewriting journey, premiering in 2012 and reaching Broadway in 2015.
And he’s since been involved with major productions many people recognize.
This isn’t a quirky footnote. It connects directly to startups:
Broadway is basically a startup factory where:
you pitch constantly
you raise capital
you recruit talent
you iterate on product (the show) through endless rewrites
and you live or die by market reception
In other words: it’s venture—with better costumes.
The meta-lesson:
founders who can tell a clear story don’t just raise money—they recruit belief.
And belief is the first ingredient in everything else (customers, hires, partners, momentum).
Practical takeaways for founders and investors
1) Build your “nonlinear advantage” by stacking worlds
Lorenzo’s career works because he cross-pollinated: AI + investing + community + storytelling.
That mix creates pattern recognition other people don’t have.
Founder version: don’t just learn your industry—learn the adjacent system that controls distribution, capital, or trust.
2) Flywheels beat heroics
Gaingels didn’t scale on hustle alone. It scaled by making the network itself more valuable with every new node.
Ask yourself: what gets easier as you grow? If the answer is “nothing,” you don’t have a flywheel—you have a treadmill.
3) Own the rails when the rails are strategic
If your business depends on operations being timely, reliable, and trusted, outsourcing the core machinery can become an existential risk.
4) Inclusion can be an engine—not a tax
Gaingels’ thesis is that inclusive capital tables create long-run compounding effects—wealth flows into communities that reinvest, expanding the ecosystem.
Whether you’re mission-driven or purely returns-driven, the punchline is the same:
more doors open → more talent enters → more winners emerge.
The closing thought: 2,700 investments isn’t the headline—it’s the proof
The tempting takeaway is: “Wow, 2,700 is a lot.”
But the real takeaway is what that number implies:
Gaingels didn’t just find a good deal source. They built repeatable infrastructure—operationally, socially, and financially—that keeps producing opportunities.
Or, in Broadway terms:
they didn’t just get lucky with one hit show.
They built a theater that can keep opening nights coming.
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Chapters:
00:00 – Introduction to Lorenzo Thione
01:22 – Growing Up in Milan and Early Career Path
03:47 – Entering the World of AI and Natural Language Search
06:10 – Building PowerSet and the Microsoft Acquisition
08:34 – Early Days of Cloud Computing and EC2
09:57 – What Gaingels Is and How It Started
12:04 – The Venture Syndicate Model Explained
14:25 – Scaling a Network-Driven Investment Platform
16:01 – Managing SPVs and Venture Infrastructure
18:20 – The Mission Behind Inclusive Investing
22:10 – How Networks Drive Venture Outcomes
26:05 – Broadway, Storytelling, and Entrepreneurship
30:15 – Lessons for Founders Raising Capital
33:10 – Closing Thoughts and Future of Venture Networks
Transcript
Brian Bell (00:01:15):
Hey, everyone, welcome back to the Ignite podcast. Today, we’re thrilled to have Lorenzo Thione on the mic. He is managing director at Gangel’s, a serial entrepreneur who sold his natural language startup to PowerSet to Microsoft, a co-founding chairman of Startout, supporting LGBTQ plus founders, and a Tony Award winning Broadway producer. So much to talk about. He sits at the rare intersection of venture technology and storytelling, built a career proving that nonlinear can be a competitive advantage. Thanks for coming on, Lorenzo.
Lorenzo Thione (00:01:42):
Hey, thanks, Brian. It’s a pleasure. Excited to be here.
Brian Bell (00:01:45):
Yeah. And so for the audience, it’s funny, Lorenzo and I realize we’ve collaborated on many, many deals over the years, but we’ve actually never spoken face-to-face or on the Zoom or phone call or never met. So this is the years in the making at this point.
Lorenzo Thione (00:01:58):
Yeah, that’s right. It’s like you kind of seem like you think you’ve come to know someone and you’re like, wait, we’ve never really spoken, have we? Yeah. I don’t know where you were based, actually.
Brian Bell (00:02:07):
I don’t know where we’re going for you. I’m east of Sacramento. I moved out during COVID. So I was in the Bay for 10 years. And then I didn’t start Team Ignite until I was sitting here in my pajamas during COVID. I was like, I think I’ll start a syndicate and start, you know, syndicating investments. This is pretty fun. COVID? Yeah. I’m for it, actually. That was a great time to do it, right? Right in COVID. But yeah, I’d love to get your origin story.
Lorenzo Thione (00:02:29):
Yeah. So as you might kind of intuit from my name, I’m Italian. I was born in Italy, in Milan, and I grew up there and didn’t really kind of expect necessarily I would end up in the States, but I ended up taking on a scholarship for what was supposed to be an exchange period in the US. And then once I got to the University of Texas in Austin. I finished up my undergraduate degree and ended up signing up for graduate school. So I stayed for graduate school. And it was the kind of beginning of the prior growth phase of artificial intelligence. Like as you, you know, if you kind of like break down AI’s history and evolution, you had like the first summer in the 70s and mid to late 80s. Then you’ve got the first winter through all of the 90s. Then you’ve got the second summer, really in the early 2000s that led to kind of the early machine learning, deep learning kind of advances. And then there was kind of this quiet period until the generative AI and transformer era kind of really came to be. So I was really getting my degree and getting interested in sub-branch of artificial intelligence, which now is really on vogue at the time, was probably not as much so, which is natural language analysis and processing, computational linguistics. A lot of it was symbolic. Statistical methods kind of started to take a little bit more the front stage. That’s sort of what became what my focus was through graduate school and then ended up graduating and through an internship became a scientist at Xerox PARC or rather FX PAL, which was a sister laboratory with PARC. I was effectively down the hall from Alan Kay and a bunch of really amazing people, you know, that sort of make up the history pages of computer science. And it was an incredible experience. And as you may know something about Xerox and Xerox PARC, they have like a really great track record of inventing amazing technology and a really poor track record of making any money out of it. And I was focused on, as you would at Xerox, document understanding, information retrieval, kind of all the aspects that kind of dealt with unstructured information that often was in documents and so on. And ended up working on this technology that looked a lot like RAG, effectively looked a lot like retrieval augmented generation. Just using different type of technologies, we were using very expensive computation to parse and understand the content of each sentence sort of in a narrower scope than what very large multibillion parameters transformer models do today. But we were doing a very similar semantic extraction and then indexing that information into some kind of database that would be useful to search and retrieve information using natural language. And so that was the beginning of what became the technology for the company I co-founded called PowerSet. In 2003, 2005, started the work around PowerSet, which was born with the mission of effectively creating smarter AI-powered search. That sounds like something that people give for granted and understand why that would be useful today. It really wasn’t at the time. The amount of sort of denial and skepticism that we encountered, not in whether we could do it, which would have been legitimate skepticism, but rather whether anybody would need it was what we were fighting up against. which is effectively the common, the consensus was that search had been solved. Google was fine. And that keywords that people, all people wanted to do was using keywords to retrieve the information that they wanted and not really understanding that actually in, you know, the idea is nobody is going to type in long sentences into a search box, which is, Ridiculous, if you think about it today, whether you’ve augmented it with speech recognition or not, people are clearly very willing to write up paragraphs of instructions and prompts and go back if the experience you get is 100x better or transformatively better than what could have been done before. But we did have some amazing investors that kind of believed in it. And so it was, I think it was Founders Fund first ever investment and the Foundation Capital was one of our investors as well and built what I can only describe as the absolute star team around the topics of AI, information retrieval, technologies, search development. Even MLOps and DataOps at the time, our company was so computationally intensive, demanding for computation at a time when the cloud didn’t exist, that we actually attracted some investments from Bezos’ family office. And we one day received a phone call and it was like, hey, from the Amazon team is like, we are thinking we have all of this extra infrastructure and we’re thinking that we might let people use our extra computational infrastructure when it’s not used. We’re calling it Elastic Compute Cloud EC2. And we think that you’d be a good partner to test this out. And I think we were the very first non-Amazon users of EC2. So ended up building a lot of infrastructure to manage distributed operations in the hybrid between the cloud as it existed at the time and our own data center, which was still at the time when you had your own machines and, you know, procure them and provide provision them on your own data center.
Lorenzo Thione (00:07:59):
And we built an awesome team. As you mentioned, a few years later, we were fortunate enough to exit the company in a good acquisition to Microsoft. Microsoft already was showing, I think, really signs of foretelling leadership in seeing AI as a key to competing in search. And we became some of the technology that made up the original launch of Bing. And I think we provided, you know, ultimately our technology was too expensive and didn’t scale out quite as much to really be usable across the entire web. And the performance of it was significantly better on informational type of queries than it would on a lot of what the web was being used for at the time, which was navigation or search was being used for at the time, which was navigation. And so we, I think we launched as part of being a powering queries that were hitting Wikipedia and Quora and so on. But we also provided a really great story to Microsoft as to why Bing was different than Live Search, which was their product prior to Bing, and why that was a worthy alternative or competitor to Google. And I think we were part of that early story. But besides that, I think that the thing that became something I’m really proud, like I said, is the amazing team we were able to put together. And the folks that were part of the PowerSet, original PowerSet team, all went on to either lead incredible organizations and AI efforts and research at large companies like Nuance and Google and eBay and LinkedIn and then Adobe, or started companies that became generationally meaningful in their own, right? One of the founders of GitHub was part of our team, as well as Weights and Biases, Crowdflower, Touring, and Runway, even Runway Financial, now the video generation one. So really incredible group of people.
Lorenzo Thione (00:09:55):
After the acquisition, my life sort of kind of, like you said, became nonlinear in a lot of different ways. And obviously, I had the ability to begin supporting other founders and a lot of the people that came out of the Power Set team and the companies that they were starting. I had the fortune of being able to invest in them and then became an angel investor first in my own right, as well as having you mentioned starting Startout Nonprofit, which is now the premier nonprofit organization supporting LGBTQ entrepreneurship across the high growth landscape, as well as being part of Gangel’s from its very origin. And I’m glossing over a couple of other startups, as you would things that didn’t last long and others that actually ended up being profitable and bootstrapped from day one and are still around, which is something I think I recommend to every entrepreneur. Great thing is not to have investors if you don’t have to have any.
Lorenzo Thione (00:10:47):
But I was part of the Gangel’s kind of experiment, so to speak, from the very beginning, when we were just a small club of investors that were trying to initially invest within the LGBTQ entrepreneurial community. And then over time, grew into what it is today, which is one of the largest and most active venture syndicates in the world, supporting diversity, diverse leadership, talent, and capital across the entire venture ecosystem. So we will invest alongside great other investors. So we’re not lead investors, right? We bring capital from a very diverse group of capital allocators. We support our portfolio companies with their hiring and their governance and board recruitment and advisory board recruitments, often tapping into pools of talent that they don’t have access to on their own. And we’ve grown in this way over a portfolio that is now 2,700 portfolio companies. Over a billion dollars in invested capital. A really amazing organization.
Brian Bell (00:11:50):
2,700 over how many years?
Lorenzo Thione (00:11:51):
Well, technically since 2013, but like the model really didn’t start to evolve until 2018. So 2018-19 is when I would actually start to count. You know, it’s obviously a very large amount of relatively small investments, although especially because we invested both in the early stage and at the late stage, we’ll have some larger deployment of capital. And over time, we’ve attracted LPs that are more family offices or multifamily offices and institutions in nature. And so the capital that can be allocated to some of those deals becomes higher. But largely, we are still a very sort of grassroots diverse group of investors that have this double bottom line of both investing in amazing companies that have incredible venture investors that we follow, but also with an eye to knowing that those companies want our help and are aligned with us in wanting to build truly inclusive organizations at the level of talent, governance and capital. And we make this also very approachable so that investors can often invest minimum investments that are very, very small compared to sometimes what you would need to do if you were an angel investor trying to get on a cap table on your own, given the fact that often you just can’t, right? Especially if you’re trying to invest in Series B, Series C, and so on.
Lorenzo Thione (00:13:11):
You run a syndicate, you know how the business works. Really is but effectively we work as both you know just the syndicator which is you know capital but also as almost like a fund meaning that we are partnering with the companies the companies look to us to help them in all the ways we can help them and now the depth and the with of the network itself has become an asset because the amount of business introductions, investors introductions, business opportunities that come from cross portfolio connections have become part of that flywheel that kind of continues to push it forward.
Lorenzo Thione (00:13:47):
And then there’s my other hat as a writer and producer in the world of Broadway, which I’m very happy to tell you more about if it’s relevant to your interest.
Brian Bell (00:13:55):
I’d love to hear about it. How did that come about?
Lorenzo Thione (00:13:58):
So I mentioned coming to the US now 25 years ago, it was not too long before September 11 happened. And that experience really had a big impact on my personal life as a recent immigrant, as a friend to many others who were immigrant, many of which fell into categories or groups that were all of a sudden being looked at with suspicion and with less than friendliness, I would say, in the immediate aftermath for no fault of their own other than either the way they look, the color of their skin, or their national origin.
Lorenzo Thione (00:14:01):
That experience really had a big impact on my personal life as a recent immigrant, as a friend to many others who were immigrant, many of which fell into categories or groups that were all of a sudden being looked at with suspicion and with less than friendliness, I would say, in the immediate aftermath for no fault of their own other than either the way they look, the color of their skin, or their national origin. That experience, in a lot of ways, kind of created a nugget of awareness and understanding and sensibility that was only amplified by my own experience. And like I said, as an immigrant, no matter what, you feel the precariousness of building a life and a career and a business and all of these kind of connections to a world to which you feel there is something missing in the kind of you’re not a citizen yet. You may be working towards permanent residency and citizenship. And it only happened several years later for me, right? First becoming a green card holder and then a naturalized citizen.
Lorenzo Thione (00:15:15):
So in 2008, I was already a green card holder, but not yet a citizen. I met randomly after the acquisition, I met the actor George Takei. So I met him in a theater one evening and we are striking up conversation and, you know, just making small talk. But he ends up telling me the story of his childhood when he was a child of five. He and his family were taken in the middle of the night at gunpoint by the U.S. Army, put on trains with blacked out windows and taken to what would become a prison for them for three and a half years. Actually several different camps that they were imprisoned in.
Lorenzo Thione (00:15:51):
You know as we know this is one of the most egregious violations of U.S constitutional rights. These were citizens. He was born in the United States. His father was born in the United States. His mother was a naturalized citizen. So you know this was happening across the entire southwestern area of the United States. Definitely up in Washington State where I’m from.
Brian Bell (00:16:09):
Yeah.
Brian Bell (00:16:10):
That happened too in Washington and even in Canada, actually, but 120,000 people.
Lorenzo Thione (00:16:16):
And as he was telling me the story, obviously kind of the connections to my own understanding and experience of that precariousness of that sort of Damocles that you have, where all of a sudden one day you can wake up and the geopolitical order has changed and your life is thrown upside down for no fault of their own. And of course, we are seeing the relevance of that story today even more than I could have ever anticipated in 2008, where what I was feeling were the echoes of September 11. But things in the years that came sort of made that story even more relevant.
Lorenzo Thione (00:16:50):
But at the time, I was like, you know what? This is a story that’s too important and too few people know it. And it happened to be also what he described as his life mission to tell the story of the internment of Japanese-Americans. And you started the conversation saying, I live at this intersection of storytelling and entrepreneurship. And I think to be a good founder, entrepreneur, money raiser, and so on, your primary skill is to be a good storyteller and to create an emotional connection with your audience.
Lorenzo Thione (00:17:19):
Whether it be an audience of one that you’re raising money from or trying to hire for your business, or an audience of many selling your products to or telling a story where your product is a story. Having never written or worked in the theater before, I got it in my head that I would, and with a good friend and collaborator, pitched the idea to George a week or two later about telling this as a musical, as a Broadway musical, or rather a musical that would end up on Broadway.
Lorenzo Thione (00:17:47):
And so we embarked on this journey that became a seven-year journey of writing and rewriting and refining a musical titled Allegiance, which opened in 2012 in San Diego at the Old Globe Theater. And then from there moved to Broadway in 2015, starring George Takei and Lea Salonga, which is now available actually as a film. We did it as a movie on Broadway. People can still see that production, which is one of the great prides and joy of my life.
Lorenzo Thione (00:18:20):
And became the beginning of a separate and parallel career as a creator and creative producer on Broadway, the West End and in theater in general. And I’ve been fortunate to be part of the producing team of a lot of other shows, including some that people in your audience would know, Hadestown, & Juliet, Days of Wine and Roses and The Notebook and so on.
Lorenzo Thione (00:18:43):
And currently working on several new projects, which we’ve originated, co-created, originally written, and then brought other collaborators to work on, including an upcoming West End musical called Indigo, which premiered last summer just north of London.
Brian Bell (00:19:00):
Amazing. What an amazing story. There’s so much to unpack there. I’ll probably circle back to the beginning and then we’ll kind of take it step by step because I want to know, you know, back to the days of PowerSet, like what did you learn about being a great investor by being like a founder who went through an acquisition?
Brian Bell (00:19:15):
What was it that kind of informed how you invest now?
Brian Bell (00:19:19):
If you think back to it, like, was it the timing was right for PowerSet? Was it the team? What is it about the PowerSet experience that kind of informs your current investing framework and how you think about it?
Lorenzo Thione (00:19:29):
Well, I mean, I learned some important lessons about how this world works without trying to pass judgment on whether that’s right or wrong or whether it can be changed or improved. And that is the absolute and ultimate important lesson of relationships and network.
Lorenzo Thione (00:19:29):
Well, I mean, I learned some important lessons about how this world works without trying to pass judgment on whether that’s right or wrong or whether it can be changed or improved. And that is the absolute and ultimate important lesson of relationships and network. And I was the technical founder in a team of three where my two other co-founders had long established networks within the Silicon Valley community. Knew investors, had worked as entrepreneurs in residence at funds, knew a lot of the people that were involved. And especially at that time, but it hasn’t really changed, the importance of that to open the right doors cannot be underestimated or understated.
Lorenzo Thione (00:20:15):
And then I think I learned the importance of a founding team where you have the right complementary skills and the right complementary kind of experience that can really answer and address investors’ concerns in the early days. And so I think we had a really great founding team that brought operational experience, fundraising and executive experience and technology, both from something that was so research oriented, not only the work I had done at PARC and that was part of the technology we were licensing and bringing, but also the people that we were able to bring onto the team.
Lorenzo Thione (00:21:00):
And I think what that does in terms of how I look at investments today is, you know, in a similar way is first of all the amount of time in any investor’s day is limited. And the amount of potential deal flow that exists out there is unlimited effectively.
Brian Bell (00:21:18):
Effectively, yeah.
Lorenzo Thione (00:21:20):
Thirty thousand pre-Series A companies a year. So you have to decide on some kind of proxy for how you’re going to filter. And filtering through the warm introduction, the connection, the people that you’re co-investing with or have co-invested with, or the people that you’ve worked with, obviously is already a really strong proxy for the quality of the team and capabilities and sort of skills that are critical to the founder journey.
Lorenzo Thione (00:22:02):
And I think to the extent that we’ve seen institutions doing some of the work that universities couldn’t quite do, universities like Stanford and Harvard certainly at MIT had sort of a history of creating entrepreneur classes, people that were technologically skilled but also had the right qualities to be founders.
Lorenzo Thione (00:22:19):
The next big evolution we’ve seen in that institutional filter I think is probably Y Combinator, where that became one of the ways in which you would know that if someone had been receiving funding from YC, you had a basis of what you would look for in the quality of the founder that someone else had screened for.
Lorenzo Thione (00:22:33):
And so that became one of the filters investors used to kind of decide how to winnow down from the 30,000 companies to the ones that you can actually take meetings with.
Brian Bell (00:23:54):
Yeah, love that. And we kind of breezed through the StartOut to Gangel’s story of it. Maybe you can explain what StartOut was and how that kind of led into Gangel’s.
Lorenzo Thione (00:24:02):
Yeah. I mean it was post-acquisition obviously it was a good acquisition. We were integrating the team into Microsoft, but I knew I wasn’t going to stay long-term. I wanted to kind of do other things that felt entrepreneurial.
Lorenzo Thione (00:24:19):
And so I looked at the model that had served me as a founder — the founder networks and the founder lunches and the meetups and so on where so much of that early ecosystem had come to support my founder journey.
Lorenzo Thione (00:24:34):
And found that it existed for several groups of affinity groups whether it be women or founders of color. There were communities where people were seeking a shared life experience as a proxy for connection which then helped create more opportunities for support and collaboration. And that didn’t exist in the LGBTQ community at the time.
Lorenzo Thione (00:25:00):
And it just sort of happened as a random conversation with three other founders I knew and we realized that a network like that didn’t exist.
Lorenzo Thione (00:25:17):
Around that same time I had come out shortly after September 11. That moment really made me realize life is fleeting and you’d rather live authentically than hide.
Lorenzo Thione (00:25:35):
From that moment onwards I’d been out with investors and employees and friends. But that wasn’t the case for some of the founders I knew who were still not out to their boards or employees.
Lorenzo Thione (00:26:27):
And I remember asking them why. And the answer was always the same: I know what I have to lose and I don’t know what I have to gain.
Lorenzo Thione (00:27:14):
Which by the way was very similar reasoning that Tim Cook privately expressed before he came out publicly.
Lorenzo Thione (00:28:34):
That notion was one of the reasons StartOut needed to exist — to provide visibility and role models to others who didn’t know whether being a founder and being out were compatible.
Lorenzo Thione (00:29:00):
And that was the reason we started StartOut in 2008 in New York and San Francisco. It was volunteer-run. And the reaction was amazing.
Lorenzo Thione (00:29:56):
Twenty years later it’s now a thriving organization with more than 20,000 members across the country and accelerators that have helped companies raise billions of dollars.
Lorenzo Thione (00:30:28):
Gangel’s came from conversations within that community about how founders needed capital.
Lorenzo Thione (00:31:08):
So we started a small club of investors that wanted to invest in LGBTQ founders.
Lorenzo Thione (00:31:35):
Eventually we realized restricting ourselves only to those founders limited the ecosystem impact we wanted. So we redesigned the model.
Lorenzo Thione (00:32:14):
Instead we decided to invest alongside the best venture investors and support diversity across talent, governance, and capital.
Lorenzo Thione (00:33:05):
By bringing diverse investors onto cap tables we help redistribute wealth generated by venture success into communities that historically haven’t had access.
Brian Bell (00:34:32):
It’s amazing. So you guys started as a syndicate and it sounds like it started on AngelList because AngelList started doing syndicates around the same time.
Lorenzo Thione (00:34:39):
We started as an angel group actually — literally people writing checks directly onto cap tables before syndication platforms existed.
Lorenzo Thione (00:35:06):
The concept of SPV syndication didn’t really become mainstream until AngelList.
Brian Bell (00:35:36):
Now I’d love to get into the structure and operations. I just crossed 300 investments and you guys have 2,700. How do you manage that operational complexity?
Lorenzo Thione (00:35:53):
Well because we’ve been doing it for nearly 15 years we learned to crawl before we walked.
Lorenzo Thione (00:36:10):
In the early days everything was spreadsheets. Then databases. Then automation. Before you know it you’ve built internal infrastructure.
Lorenzo Thione (00:36:45):
At some point we collaborated with AngelList but a large portion of our syndications still run on internal systems.
Brian Bell (00:37:40):
Interesting. So you spin up your own LLCs and manage taxes and K-1s internally?
Lorenzo Thione (00:38:03):
Yes and beyond cost there are strategic reasons. Control over LP relationships, data, timing of tax documents, and operational independence.
Lorenzo Thione (00:39:29):
The last thing you want with thousands of SPVs is dependency on a third party failing operationally.
Brian Bell (00:40:03):
Do you guys only syndicate or do you run funds as well?
Lorenzo Thione (00:40:08):
We run a few funds as well. Some LPs prefer giving us discretionary capital instead of evaluating every single deal.
Brian Bell (00:41:17):
Yeah that makes sense.
Lorenzo Thione (00:41:21):
But fundamentally we still treat each SPV like a fund that invested in one company.
Brian Bell (00:47:29):
I’d love to go back to Broadway storytelling and producing. What impact has that had on your investing?
Lorenzo Thione (00:47:37):
Just like venture capital you can approach Broadway purely financially or as a way to create impact.
Lorenzo Thione (00:48:29):
Broadway isn’t necessarily the most efficient capital allocation but occasionally returns are extraordinary.
Lorenzo Thione (00:49:02):
The difference is venture seeks exits while Broadway can produce returns for decades through licensing and touring.
Lorenzo Thione (00:50:13):
Theatre also uniquely shapes culture and challenges power structures through storytelling.
Brian Bell (00:53:12):
Looking forward 3, 5, or 10 years, what excites you?
Lorenzo Thione (00:53:18):
AI investing excites me a lot. I manage the AI investment strategy at Gangel’s.
Lorenzo Thione (00:53:36):
And creatively I’m excited about Indigo, a musical about three generations of women navigating autism, dementia, and family relationships.
Brian Bell (00:55:42):
Amazing. Let’s finish with some rapid-fire questions.
Brian Bell (00:55:46):
What’s the best founder trait you see repeatedly?
Lorenzo Thione (00:55:49):
Vision. I spot it through storytelling and enthusiasm. I want to understand why that founder is uniquely obsessed with the problem they’re solving.
Brian Bell (00:56:40):
Why the high-volume investment strategy?
Lorenzo Thione (00:56:50):
Because scale matters for our mission. If we want to change the venture ecosystem we have to operate at ecosystem scale.
Brian Bell (00:58:29):
What’s one thing VCs get wrong about non-traditional founders?
Lorenzo Thione (00:58:33):
Sometimes they invest for optics rather than conviction.
Brian Bell (01:01:07):
What belief did you change your mind on in the last decade?
Lorenzo Thione (01:01:14):
That founders should raise as much venture capital as possible whenever it’s available.
Brian Bell (01:02:29):
Best piece of advice you’ve received?
Lorenzo Thione (01:02:32):
Be obsessive about your network and how you help it.
Brian Bell (01:04:07):
Lorenzo, thanks for sitting down with me. Really learned a lot. What an incredible journey.
Lorenzo Thione (01:04:17):
Thanks Brian. It was a pleasure.
