Boldstart Ventures specializes in what it calls “inception investing,” where it makes bets on founders in the earliest stage of creating a company – often before they’ve written a single line of code. As Boldstart Partner and Somerville, Massachusetts resident Ellen Chisa notes, “If someone announces on LinkedIn that they’re starting a company, it’s often already too late for us.”
Startup Boston caught up with Ellen to discuss this investing philosophy and how she leverages her background as an engineer, founder, and manager at companies from Kickstarter to Microsoft to help entrepreneurs get started and grow.
This interview offers an insider's view into the nuanced world of early-stage investing. Ellen provides insights into how Boldstart identifies potential, supports founders, and navigates the ever-evolving landscape of technology entrepreneurship – particularly in an era where AI is reshaping most every sector.
Startup Boston (SB): You have both an engineering and a business background, and you’ve also been a founder yourself. Could you walk me through briefly how you got to where you are today?
Ellen Chisa (EC): As you mentioned, I originally went to engineering school. Something people don’t always pick up on is that the engineering school I attended—Olin College of Engineering, just outside of Boston—was pretty much brand new when I enrolled. When I was admitted and decided to matriculate, there were no alumni yet. So, it was always a bit entrepreneurial while also being engineering-focused.
Because of that, the college placed a heavy emphasis on entrepreneurship. In fact, I actually dropped out during undergrad to launch my first startup with five of my friends. It was a total disaster—but a fun and valuable learning experience. That’s when I realized I was definitely going to keep doing startups.
One of the challenges with that first startup was that we weren’t very good software engineers yet, so we ran into a lot of software-related problems. I realized I needed to learn how to build higher-quality software if I wanted to succeed in the future. That led me to spend a couple of years at Microsoft. After that, I decided to return to the startup world and worked at Kickstarter in New York. Then I joined a travel company in Boston called Lola during the last AI wave, founded by Paul English, who also co-founded Kayak. After that, I started a programming language company called Darklang.
SB: Wow, so you’ve had quite a diverse range of experiences.
EC: Yes, I’ve thought about this a lot recently. There was definitely a period where I was strictly focused on consumer-facing products, and then a time when I was all about developer tools. Now, at Boldstart, we’re an enterprise-focused fund. This diversity gives us a lot of flexibility in the types of companies we can work with. I can look at developer tooling, application layer, and infrastructure or even delve into deep tech. It’s been rewarding to have such a broad lens.
SB: That’s very cool. Can you talk me through how you decided to join Boldstart? What attracted you to it, and how did you get started there?
EC: Boldstart actually invested in my previous startup, Darklang. Even though Boldstart didn’t lead that round, their smaller fund at the time made a big impression on me because of how much work and thoughtfulness they brought to the table.
After I left Darklang, I was taking some time to figure out what I wanted to do next—whether that was starting another company, joining a team in-house, or something else. I had been angel investing on the side, and the team at Boldstart suggested I join them, even if only temporarily. They said, “Why don’t you come here, and we’ll figure it out? Maybe you’ll want to start something, and we can back it. Maybe you’ll want to join a portfolio company. Or maybe you’ll find that you enjoy investing.” That openness eventually led to my current investment role.
SB: That’s a fascinating journey. I know Boldstart focuses on inception investing, which is quite different from investors who typically engage with more established companies. Since you’re often investing before there’s even a product or fully-formed company, how do you spot talent and potential at such an early stage?
EC: It’s a unique challenge, for sure. Usually, if someone announces on LinkedIn that they’re starting a company, it’s already too late for us. The conventional signals that other VCs might use—like raising a seed round—often come after we’ve already engaged with a founder.
At this stage, I focus on a few key things. First, I evaluate whether the market they’re targeting is large enough. Is the problem they’re solving significant enough to sustain a company that can generate over $100 million in revenue in the next 5–10 years? Could they eventually displace the largest incumbent in their space? I’m looking for ideas that make me think, “Yes, this could be huge.”
Next, I spend time with founders discussing their first hypothesis—how they plan to reach that vision. For us, it’s less about whether they can write code or build a product. We assume they can. It’s more about whether they can efficiently scope and execute their initial experiments to learn quickly and iterate.
SB: Do most of the founders you work with have prior startup experience? Does that factor into your decision-making?
EC: It’s a mix. We have some founders who’ve built multiple companies before. For example, we’re working with Guy Podjarny on his third company now—his second company, Snyk, was a major success in our portfolio. But we also work with plenty of first-time founders. It really depends on the individual and their ideas.
SB: That makes sense. So when founders come to you, you evaluate them based on the criteria you mentioned—market size, hypothesis, and potential for growth. Do you also help them refine their ideas?
EC: Absolutely. There are cases where founders come to us with an idea, and we help them refine it. For instance, we might say, “Have you considered this market?” or “Here’s what we’ve seen from similar buyer personas in the past.” Sometimes they’ll go back, work on the idea for a few months, and realize, “Actually, you’re right—this market isn’t as promising as I thought.” In those cases, they might come back to us with a new idea. It’s often an iterative process.
We also actively reach out to people doing interesting work—whether in academia or within enterprises—because we want to meet great people, even if they’re not starting a company today. They could become future founders, portfolio customers, or even angel investors. Building those relationships early is key.
SB: Speaking of technology, is there a specific area you’re particularly excited about, or are you more industry-agnostic?
EC: We’re fairly agnostic, but we try to have a prepared mind. Some investors might have a very specific thesis and wait for a founder who aligns with their vision. We take a different approach—we listen to founders and assess whether their vision makes sense to us. It’s less about dictating what we think the future should look like and more about aligning with the founder’s perspective.
SB: I imagine AI is becoming a bigger area of focus. How are you thinking about that?
EC: AI is everywhere now. We don’t necessarily label ourselves as “AI investors,” but almost every enterprise company we look at has some AI baked into their product. For example, if someone pitches us a cybersecurity company, we’d expect some AI component to be part of their solution, but we’d still think of them as a cybersecurity company first.
That said, we’re mindful of companies that include AI as a buzzword. Some founders focus on solving customer problems first, with AI being just one part of their implementation. That’s the approach we prefer—AI as a means to an end, rather than the sole focus.
SB: Lastly, looking ahead to 2025, how are you thinking about the VC landscape, especially given economic uncertainties and interest rate fluctuations?
EC: For us, it’s largely business as usual. Inception investing tends to be more insulated from market fluctuations since it involves the earliest stages of company building. We have the longest timeline before needing a public market event or acquisition, so there’s time to adapt to changing conditions.
We’ve noticed a divergence in how rounds are structured at this stage. Some founders aim for smaller angel rounds to minimize dilution and validate specific hypotheses, while others with more experience and a clear vision go for larger inception rounds. We’ve adjusted by being flexible with check sizes to accommodate both approaches.
SB: So, is it safe to say that inception investing is particularly well-structured for this type of economic environment, where there's a lot of uncertainty?
EC: I think so, yes.
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About the author: Randall Woods is a former editor at Bloomberg News and currently is a Senior Vice President at SBS Comms, a communications agency for technology companies and startups.
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