The AI CFO with Alex Wittenberg

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On The AI CFO, we're figuring out how startup finance is changing in the age of AI, in real time. I'm Alex Wittenberg, CEO of airCFO, and each episode I sit down with the people building and investing in AI in the next generation of world changing startups. Whether you're making your way through the fundraising gauntlet or building an AI-powered finance function on the other side of it, you'll hear what's actually working from founders & operators on the frontier. This podcast is a companion to the writing that I’m doing on this topic every two weeks in The AI CFO newsletter. Subscribe at aircfo.com/the-ai-cfo.

  1. 7h ago

    Every CFO Needs an Engineer | Ali Esfahani, Unconventional AI

    The AI CFO started as Alex Wittenberg's newsletter on how AI is reshaping the way startups build, operate & think about finance. Now it's a podcast too, and the first guest is Ali Esfahani, [UN]CFO at Unconventional AI, which raised a $475M seed round to rebuild the computer from the ground up and solve AI's power problem. Ali handles finance, legal, and investor relations, and he's using AI to build his own tools, from a resume screener to an AI chief of staff. He explains why every CFO should have a software engineer, why seat-based software pricing is dead, and how to start building without a technical background. If you listen to Funded, you're in the right place. Same show, new name. More about Unconventional AI: https://unconv.ai Read The AI CFO newsletter every two weeks: https://www.aircfo.com/the-ai-cfo

  2. Jul 28

    This VC Says There's Still Room for AI Startups | Nick Tippmann, TipTop VC

    Nick Tippmann, founder of TipTop VC, has spent his career betting on vertical software, first as founding CMO at Greenlight Guru, now as an investor backing the next wave of vertical AI startups. In this conversation, Nick lays out how he actually evaluates founders and markets, from a simple IQ, EQ, and grit framework to the TAM math behind why vertical AI represents such a massive opportunity. More about TipTop VC: https://www.tiptop.vc/ 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

  3. Jul 1

    The Fundraising Story Most Founders Won't Tell You | Andrew Rea, TaxWire

    Andrew Rea is the co-founder and CEO of TaxWire, a global sales tax compliance platform handling everything from calculation and filings to the full managed service layer. In this episode of Funded, he sits down with Alex to break down three completely different fundraising experiences: a pre-seed that took 200+ investor conversations to close, a seed round that generated seven term sheets in four days, and most recently, a Series A that went from phone call to term sheet in 24 hours. More about TaxWire: https://www.taxwire.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

  4. Jun 4

    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

  5. 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

  6. 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/

  7. 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.

  8. 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.

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About

On The AI CFO, we're figuring out how startup finance is changing in the age of AI, in real time. I'm Alex Wittenberg, CEO of airCFO, and each episode I sit down with the people building and investing in AI in the next generation of world changing startups. Whether you're making your way through the fundraising gauntlet or building an AI-powered finance function on the other side of it, you'll hear what's actually working from founders & operators on the frontier. This podcast is a companion to the writing that I’m doing on this topic every two weeks in The AI CFO newsletter. Subscribe at aircfo.com/the-ai-cfo.

Information

  • Creator
    airCFO
  • Years Active
    2026
  • Episodes
    22
  • Rating
    Clean
  • Copyright
    © 2026 airCFO