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 (http://aircfo.com/the-ai-cfo).
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 (https://unconv.ai)
Read The AI CFO newsletter every two weeks: https://www.aircfo.com/the-ai-cfo (https://www.aircfo.com/the-ai-cfo)
28 Jul 2026
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/ (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 (https://www.aircfo.com/the-ai-cfo)
1 Jul 2026
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 a Series A that went from phone call to term sheet in 24 hours.
More about TaxWire: https://www.taxwire.com/ (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 (https://www.aircfo.com/the-ai-cfo)
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