Venture Voices | 25 Madison
For our first episode of Venture Voices in 2025, we are joined by Jaja Liao, Principal at 25 Madison, a venture studio and early-stage fund focused on pre-seed and seed investing. Jaja studied molecular biology at Yale and started her career at Google as a business analyst on the AdMob and AdX products. Looking for more hands-on, high-growth environments, Jaja joined Clover Health—still a startup at the time – on its growth strategy team.
After Clover Health, she spent several years on the early-stage investment team at Headline. In 2022, Jaja joined 25 Madison as a studio, and when the studio expanded into a fund, she transitioned to lead the fund investing practice. She uses her broad experience to identify and help the most promising early-stage companies.
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25 Madison
Why did you decide to join 25 Madison, and can you share its backstory and evolution?
Number one: we wanted to double down on the winners that we incubated via the studio.
Number two: we also wanted to invest in new companies that we liked in the market but hadn’t incubated ourselves.
That was in 2022 when I joined, we now run both a studio and a fund. I only work on the fund side, but I still work with my colleagues on the studio investment team as well. One last thing to note is that Apollo Global Management is our largest investor.
How does 25 Madison’s relationship with PE funds shape your investment strategy? Are there specific sectors you prioritize for startup incubation and investment?
Within the B2B SaaS sectors you mentioned, are there certain categories performing better than others?
What is 25 Madison’s value add? How do you help your portfolio companies stand out in the market?
Do you think your partnership with PE firms differentiates you from other venture capitalists? Are there others with similar models?
What sets us apart is that we collaborate with multiple PE firms. My studio investment team works closely with their portfolio companies on a daily basis, to identify key pain points. From there, we explore whether we can incubate a product to address those specific challenges. We actively engage these companies as design partners, rather than simply spinning out of a PE fund and stopping there.
Why is now a particularly good time for companies to target Private Equity firms?
AI plays a key role here. Many PE firms and their portfolio companies care about implementing AI but are not always at the forefront of adoption, unlike the venture capitalist and tech sectors. They’re interested but often don’t know where to start. Efficiency is a major priority for these firms, and AI provides a powerful tool to help them achieve it. It’s a great feature and product for these types of firms to adopt, making them ideal partners for startups looking to make an impact.
Do PE companies typically come to you with AI-related challenges, or do you take the lead in proposing solutions?
During these discussions, they might realize and articulate, ‘Oh, this particular task I do every week or every day is incredibly frustrating. I’d gladly pay to offload it.’ This evolves into a longer conversation, which helps us understand both the external and internal factors. From there, we can propose effective AI solutions and hopefully, engage them as design partners.
Is there resistance to AI adoption from companies? If so, how do you help overcome it?
The key is to discuss AI adoption with companies at a time when they’re not struggling with a long list of challenges, as it's hard to get people's attention then. If you enter post-acquisition for example, when they’re making changes and starting to think about the next 3–5 years, you have the chance to interview them and figure out how to help them.
How would you describe the culture at 25 Madison, and how does it shape your approach to building companies?
We’re always looking for creative ways to solve problems, and it permeates throughout our entire culture. Specifically, we love solving problems that are the unsexy, overlooked areas that other people tend to ignore.
We’re very open to being creative in how we solve problems, whether that’s through building a product or trying something that others might not have attempted. That lens of creativity is deeply embedded in our culture.
What does your diligence process entail when evaluating startups, and what should founders focus on to stand out?
Our diligence process isn’t drastically different from a normal VC diligence process, we’re very focused on talking to potential users in our network. This ties back to the sectors we invest in: industrial supply chain, commerce, healthcare, and regulated industries.
For startup founders to stand out, having a clear understanding of their target customer and demonstrating how their product addresses a specific pain point is key. If we can’t diligence a buyer or use case within our network, it often means the product may not have a real use case or isn’t a fit for us.
Are there specific traits you look for in founders or does it vary depending on the startup?
On the studio side, it’s more about domain expertise. For example, if someone is building something specific in an area like industrial supply chains, we look for expertise in that area. These profiles tend to do better on go-to-market and sales. We’re not looking for perfectly formed teams in the studio, because part of the studio’s purpose is to help augment and build the rest of the team.
Do you think progress is being made in improving diversity for female founders?
What should startup founders focus on to stand out during a pitch?
Do you have an example of a particularly strong pitch that stood out to you?
Sometimes you can just tell from the first conversation with a startup founder that they’re uniquely suited to solve a specific problem. I usually know after the first meeting if I want to invest or not—it’s very intuitive now. If I’m not excited in the first meeting, it’s usually a sign that something’s off.
What’s your outlook on the 2025 global startup ecosystem?
Are there any specific industries or opportunities you would recommend new founders explore for big market disruptions?
Any books, resources, or activities you’d recommend for startup founders to grow and develop themselves?
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