The AI CFO with Alex Wittenberg

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

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

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

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

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

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/

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.

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.

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.

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.