Funded with Alex Wittenberg

airCFO
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Funded is a show taking you behind the scenes of the startup fundraising process. I'm Alex Wittenberg, CEO of airCFO, and every episode I talk to people who've been through the fundraising gauntlet: founders who just closed rounds and VCs writing checks right now. We get into the gory details that don’t make it into the press release. Founders share how they hustled their way onto VCs’ radars, how they refined their pitches, and what terms they negotiated. VCs explain what makes them take a meeting, how their firm evaluates deals, and why they say yes or pass. If you're raising money or thinking about it, this show is for you. New episodes every week.

  1. 4d ago

    The VC Who Invests in Cancer Care From the Inside | Ben Freeberg, Oncology Ventures

    In this episode of Funded, Alex sits down with Ben Freeberg, Founder and Managing Partner of Oncology Ventures, a seed-stage fund investing in data and infrastructure startups transforming cancer care. Ben breaks down why more than half of the 1,700 cancer deaths in the US every day are preventable with technology that already exists, how he built a venture fund where his LPs are also his most important customers, and why commercialization clarity is the number one thing that kills deals in his pipeline. More about Oncology Ventures: https://oncology.ventures 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

    50 min

  2. Apr 28

    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 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

    51 min

  3. Mar 3

    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/

    58 min

  4. Feb 11

    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.

    54 min

  5. Jan 28

    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.

    1h 8m

  6. Jan 22

    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.

    55 min

  7. Jan 22

    The Urgent Pain Point Test Every Startup Must Pass | Arun Penmetsa, Storm Ventures

    Storm Ventures partner Arun Penmetsa reveals exactly how his firm evaluates early stage B2B software startups and what separates companies with staying power from those destined to flame out. With 25 years of experience and investments across 6 funds, Storm specializes in helping companies transition from founder-led sales to scalable go-to-market teams. Arun breaks down Storm's 3-stage investment process and shares the key traits they look for in founders. He explains why team comes first, followed by market urgency, and how the AI boom has complicated traditional evaluation metrics. The conversation dives deep into what makes AI companies defensible versus those riding a temporary wave.

    52 min

  8. Jan 22

    This $55M Secret is Changing How Finance Teams Work | Ali Hussain, Tabs

    Fresh off announcing their $55M Series B led by Lightspeed Venture Partners, Tabs CEO Ali Hussain reveals how AI is transforming the finance function. Ali shares the founding story behind Tabs - how his team spent 3 months having 8 calls per day with finance professionals to deeply understand revenue accounting pain points. The conversation explores Tabs' new AI agents for billing and collections, plus Ali's 4-step framework for building production-ready AI agents in finance. He explains why finance teams have historically blocked new revenue streams and how modern tools are changing that dynamic. Ali also discusses the evolution of CFO roles in an AI-driven world, arguing we're not heading toward zero-person finance organizations but rather strategic finance teams with superpowers. He shares tactical fundraising advice accumulated over 3 years building Tabs, including the importance of running compressed funding processes and leveraging founder introductions.

    1 hr
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About

Funded is a show taking you behind the scenes of the startup fundraising process. I'm Alex Wittenberg, CEO of airCFO, and every episode I talk to people who've been through the fundraising gauntlet: founders who just closed rounds and VCs writing checks right now. We get into the gory details that don’t make it into the press release. Founders share how they hustled their way onto VCs’ radars, how they refined their pitches, and what terms they negotiated. VCs explain what makes them take a meeting, how their firm evaluates deals, and why they say yes or pass. If you're raising money or thinking about it, this show is for you. New episodes every week.

Information

  • Creator
    airCFO
  • Years Active
    2K
  • Episodes
    19
  • Rating
    Clean
  • Copyright
    © 2026 airCFO