How Lily got into investing
I didn’t take the traditional path into venture. My background is in marketing operations, and I first got into startups when I joined Tessian as an intern—fresh out of school, no real experience, just eager to learn. Tessian was pre-seed at the time, so I had a front-row seat to what it takes to scale a company from zero to $40 million in revenue. Over those four years, I picked up low-code and no-code automation, web scraping, and GTM systems-building, learning how to build and rebuild infrastructure at a breakneck pace as the company grew. By the time I left, Tessian was about to be acquired by Proofpoint for a few hundred million dollars, and I had gained a deep understanding of how startups operate at hyper-growth speed.
My move into venture happened through Flex Capital—a former Tessian colleague introduced me to the team when they were looking for someone to build automated sourcing and GTM operations for the firm. In VC, you’re essentially running a two-sided go-to-market strategy: meeting the right companies at the right time while also fundraising. I joined Flex while we were raising our second fund (which we successfully closed); over time, I started taking on an investing role alongside running our systems.
The Flex advantage: Investing through an operator’s lens
Flex is redefining venture by putting operators at the forefront. Our founder-CEOs, Auren Hoffman and Tod Sacerdoti, aren’t just investors—they’re actively running companies while backing other founders. Auren built LiveRamp, now a public company, and currently runs SafeGraph, a data business. Tod founded BrightRoll, sold it to Yahoo, then led Yahoo’s ad product team before starting Pipedream, a developer API platform.
Their experience isn’t just historical—it’s happening in real-time. That’s a big part of what makes Flex’s model work. Founders don’t just need theoretical advice —they also need insights from people who are navigating today’s challenges alongside them. The startup landscape moves fast, and whether it’s hiring, fundraising, or scaling, what worked three years ago isn’t always relevant today.
This is why having actively operating CEOs as GPs is such a differentiator. When a founder is figuring out how to hire key talent, how to build GTM systems, or how to deploy code efficiently, getting input from someone who solved that problem six months ago—not six years ago—makes all the difference. During COVID, for example, companies needed to adapt in ways that prior generations of founders never faced. Today, AI and automation are changing development cycles at a rapid pace. Having investors who are building alongside you provides an edge. We invest with the same mindset we use to build our own companies: lean, fast-moving, and hands-on.
“Having actively operating CEOs as GPs is a differentiator. When a founder is figuring out how to hire key talent, build GTM systems, or deploy code efficiently, getting input from someone who solved that problem six months ago—not six years ago—makes all the difference.”
The next wave in venture: AI, B2C, and what’s undervalued today
For the past decades, B2B software has dominated venture—and for good reason. It’s been a hugely successful category, and we spend a lot of time evaluating it at Flex. But competition is getting tougher. The incumbents aren’t 40-year-old legacy companies anymore—they’re 10-year-old startups run by sharp, capable teams still innovating. That makes it harder to carve out new opportunities, and the market is starting to reflect that.
At the same time, every company is becoming an AI company, and that’s where we’ll see the next wave of breakout successes. But the area I’m most excited about is B2C AI. Over the last decade, we haven’t seen many great consumer companies emerge at scale, whereas in the early 2000s and 2010s, B2C startups defined entire new markets. I think we’re about to see another major shift in consumer innovation, fueled by AI.
AI’s impact on B2B is obvious—automating workflows, optimizing sales, generating content. But in B2C, AI can power entirely new consumer experiences. Take a recipe app—the traditional model is just a database of recipes. But with AI, I should be able to say: “Here’s what’s in my fridge, and here’s the kind of meal I want,” and instantly get a personalized recipe. That’s a far more engaging, dynamic experience. The technology for these products is being built, but mass adoption hasn’t happened yet.
“The area I’m most excited about is B2C AI. Over the last decade, we haven’t seen many great consumer companies emerge at scale… but I think we’re about to see another major shift in consumer innovation, fueled by AI.”
One of the most exciting examples is StackBlitz, a Flex portfolio company that recently launched Bolt—a tool that lets users build full applications in just a few prompts. It’s a game-changer for developers and operates in both B2B and B2C, though its early users are more technical. But products like this—where AI removes friction in building, creating, and interacting with technology—will define the next wave of consumer innovation. The best founders will be those who can translate cutting-edge AI into intuitive, engaging experiences that drive mass appeal. That’s where I’m looking next.
The future of founders: Technical skill, distribution, and brand
There’s a growing belief in venture that the next generation of founders won’t need to be as technical as their predecessors. With AI making it easier than ever to build and deploy, the thinking goes that non-technical founders will have fewer barriers to creating successful software companies. That may be true to some extent—but I’d still always bet on a deeply technical team.
The bigger shift, though, isn’t in who can build—it’s in how companies win. With AI lowering the bar for product development, simply creating an amazing product won’t be enough. The companies that stand out will be the ones that nail distribution. That’s why we’re so excited to be investing at Seed—in this new landscape, small teams can achieve outsized outcomes without raising massive rounds, as long as they execute well on distribution and customer engagement.
The new differentiator is brand—and it’s going to matter more than ever. Customer trust, retention, and adoption will be shaped not just by what a product does, but by how it makes users feel. Creating delight and reducing time-to-value will be critical. If a customer has to wade through a paywall or complex onboarding before seeing real value, they’ll lose interest fast. The products that win will be the ones that deliver instant delight—where users feel the benefit before they even think about paying.
“The companies that stand out will be the ones that nail distribution. That’s why we’re so excited to invest at Seed—in this new landscape, small teams can achieve outsized outcomes without raising massive rounds, as long as they execute well on distribution and customer engagement.”
Look at ChatGPT—it’s already one of the five most-visited websites in the world. If I ask my dad, who’s in his sixties, what he thinks about AI, he won’t talk about open-source LLMs or cutting-edge models—he’ll say, “Oh yeah, I’ve heard of ChatGPT.” That’s the power of brand. In this next wave of company-building, brand and immediate value creation will be the new moats. Founders who understand that—and execute on it—will define the next decade of venture.
Go-to-market strategy: What founders should prioritize
A strong GTM strategy isn’t one-size-fits-all—it depends on whom you’re selling to and how they buy. If you’re selling to a niche enterprise audience, a high-volume outbound motion doesn’t make sense. Spamming a small group of specialized buyers risks alienating them before you’ve even had a conversation. Instead, founders should focus on building a community that naturally attracts those customers.
On the other hand, if your product has broad horizontal appeal, investing in a highly sophisticated outbound motion can work—especially with AI-powered personalization. But founders often assume automated outbound is always the answer. If your buyer pool is small, you can’t afford to burn trust with bad copy and generic messaging.
“Community” is a buzzword, but at its core, it means creating value for your customers before they buy. The best way to do that? Build a content engine that establishes credibility, speaks to key concerns, and meets your audience where they are.
For B2B SaaS, content is foundational to building credibility and trust. The best approach is to create one major content asset per quarter—a report, deep-dive analysis, or webinar—then repurpose it into blog posts, LinkedIn updates, and short videos. Delivering those insights repeatedly across multiple touchpoints ensures they reach the right audience and reinforce your expertise. And if you’re in enterprise sales, there’s an even sharper edge: sell something that gets your buyer promoted. Enterprise buyers are driven by KPIs and career growth—if your content makes them look smart, gives them real insights, and helps them hit their goals, you’re not just selling a product. You’re building lasting relationships.
None of this is a quick hack. But founders who master content, community, and credibility put themselves in the strongest position to win.
My hypothetical startup: Reinventing genealogy with AI
The genealogy space is overdue for disruption. Companies like MyHeritage.com have dominated the market for decades, but innovation has stalled. I’d build an AI-powered ancestry platform that automates searches, pulls from global databases, and maps deep historical family connections in a more intuitive and engaging way. Family history has huge intrinsic value and viral potential—people love sharing it, and AI could make the experience dramatically better. Plus, B2C is exciting, and I’m drawn to opportunities where technology can reshape how people connect with their past.
The advice I’d give to a new investor
Venture is a compounding job—the relationships you build over time make everything easier and more rewarding. My biggest advice? Track and nurture those relationships from day one. Whether it’s in a CRM, Airtable, or even a spreadsheet, having a system to remember who you’ve met, what they’re working on, and how you can connect them to others is invaluable. The more you help others—whether it’s introducing a founder to a key hire or helping an investor find the right deal—the more your own network strengthens over time. Invest early in building relationships, and they’ll pay off exponentially.
