Funded with Alex Wittenberg

Community, AI, and Knowing When Not to Raise | Aileen Allen, Mercury Fund

In this episode of Funded, Alex sits down with Aileen Allen, Partner at Mercury Fund, a 20-year-old Texas-based VC investing at seed and Series A in vertical AI, developer tooling, and agentic commerce. Aileen spent 15+ years as a go-to-market operator at companies like Atlassian before making the jump to venture. She shares why she thinks some founders shouldn't take venture capital at all, why the skills that matter in go-to-market are shifting toward editorial instincts and community building, and how Mercury evaluates founders when AI has made it easier than ever to ship a V1. More about Mercury Fund: https://www.mercuryfund.com [https://www.mercuryfund.com] We also have a newsletter! In The AI CFO, Alex explores the tools, wins, and hard lessons shaping the future of startup finance. Every two weeks. Subscribe here: https://www.aircfo.com/the-ai-cfo?utm_source=spotify&utm_medium=podcast [https://www.aircfo.com/the-ai-cfo?utm_source=spotify&utm_medium=podcast]

The AI-Native Playbook for Raising a $3.7M Seed Round | Andy Keil, DreamBase

Andy Keil is the co-founder of DreamBase, an analytics platform that lets AI-native teams understand their business without a data team or a single line of SQL. He sits down with Alex to discuss how DreamBase went from whiteboard to working prototype in five days, why making onboarding too frictionless killed user trust, and how he closed a $3.7M seed round with a Notion memo instead of a pitch deck. Subscribe to Funded for more conversations with founders on the real story behind startup fundraising. More about Dreambase: https://dreambase.ai/ [https://dreambase.ai/]

How Campfire Raised $100M+ While Doubling Revenue Six Quarters Straight | John Glasgow, Campfire

In the latest episode of Funded, Campfire CEO John Glasgow shares how he raised $103.5M across three rounds in under a year while running every sales call, closing the books as CFO, and building one of the fastest-growing AI-native ERPs in the market. John breaks down his fundraising strategy: stacking all investor meetings into two-week windows, choosing board members he'd worked with before, and managing back-to-back rounds while the business was exploding.

Why Market Size Trumps Everything In VC Deals | Jesse Robbins, Heavybit

Jesse Robbins from Heavybit breaks down what VCs actually look for when evaluating early stage startups and why most founders get it completely wrong. Jesse reveals the brutal truth about funding stages - pre-seed typically needs zero revenue but credible design partners, seed stage requires $500K to $1.5M in revenue, and Series A demands $1.5M to $3M. He explains why market size is the ultimate arbiter of whether Heavybit will invest, even if they love the team and product. The conversation dives deep into founder evaluation, where Jesse looks for personal grit and strong cofounder dynamics over flashy credentials. He shares why founders who can grind without positive feedback and maintain their vision through adversity are the ones who succeed. Jesse also breaks down Heavybit's investment process, from the best ways to get on their radar to what happens in partner meetings. He explains their hands-on post-investment approach, including structured onboarding, bi-weekly partner meetings, and customized sprint programs.

Strategic Confidence in the Seed Funding Round | Henry LeGard, Verisoul

In this episode of Funded, Alex Wittenberg sits down with Henry LeGard to explore his fundraising journey for Verisoul, a company dedicated to detecting fake accounts and bots. Henry shares valuable insights on the challenges he faced and strategies he employed during a seed round. In this conversation, Henry recounts a creative yet ultimately ineffective marketing stunt involving Mardi Gras cakes aimed at attracting potential clients. Alex and Henry deep dive into constructing a compelling narrative that resonates with investors by focusing not just on traction but also on the size of the market opportunity and the strength of the team. They discuss tactics for generating investor interest and managing the fundraising process effectively. Through this discussion, Henry emphasizes that investors are primarily swayed by a compelling story and potential for massive growth rather than just current performance metrics.