PODCAST · business
The AI CFO with Alex Wittenberg
by airCFO
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.
Episodes
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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…
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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,...
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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…
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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…
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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…
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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...
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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:...
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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…
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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...
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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...
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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...
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The Secret Signal VCs Look For In First Time Founders | Eric Bahn, Hustle Fund
Eric Bahn reveals the framework Hustle Fund uses to evaluate 1,000+ monthly pitches and select just 7 investments. From building Beat The GMAT to becoming a top early-stage VC, Eric breaks down the counterintuitive signals that separate future unicorns from the pack. Listen in as Eric shares real...
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From 130 Rejections to 4M Seed Round Success | Scott Hickle, Throne
Scott Hickle is building Throne, the world's first wearable for your toilet that he calls "Whoop for your poop." This AI-powered device clips onto your toilet and analyzes what's in the bowl to provide health insights straight to your phone, with the ultimate vision of becoming a smoke detector…
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Insights From a Founder Who Raised $95M in Just 11 Days | Nicolas Kopp, Rillet
Nicolas Kopp, Founder and CEO of Rillet, shares how he raised $95 million across two funding rounds in just 11 days of actual fundraising work. After building an AI-native ERP system in stealth for nearly two years, Rillet announced a $25 million Series A led by Sequoia in May, followed by a $70...
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Investing in Companies You Can't Clone | Jed Katz, Javelin Venture Partners
In this episode of Funded, we sit down with Jed Katz, Managing Director at Javelin Venture Partners. With over 15 years and more than 120 deals under his belt, Jed offers a raw and honest look at what it takes to get funded in today's dynamic market. Jed reveals Javelin's unique, sector-agnostic...
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Building Billion Dollar AI Businesses | Rudina Seseri, Glasswing Ventures
In this episode of Funded, Alex Wittenberg sits down with Rudina Seseri, Founder and Managing Partner at Glasswing Ventures, to discuss what it really takes to build and scale a successful AI startup. Rudina emphasizes the distinction between building a strong product and creating a successful...
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Founder Mistakes, Market Sizing, and Pitch Tips | Mark Volchek, Las Olas Venture Capital
In this episode of Funded, Alex sits down with Mark Volchek, founding partner at Las Olas Venture Capital (LOVC). Mark brings a wealth of experience to the discussion, having previously co-founded Higher One—a fintech company he helped lead from inception through IPO. His extensive background as...
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How to Think About Seed Stage Investing and Fundraising | Nick Adams, Differential
In this first episode of Funded, Alex Wittenberg, CEO of airCFO, sits down with Nick Adams, co-founder and Managing Partner at Differential Ventures, to demystify the venture capital fundraising process for early-stage founders. Alex and Nick provide practical, actionable insights for startup...
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Positioning Against ChatGPT and Fundraising Strategies | Taher Hassonjee, DocDraft
In this episode of Funded, Alex Wittenberg sits down with Taher Hassonjee, founder of DocDraft, to dive deep into the realities of early-stage fundraising for startups. This episode focuses on DocDraft’s journey, from the early decision to be an “AI-first” legal tech company to raising a $1.5...
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How To Impress On Your First Call | Kristina Chapple, 11 Tribes Ventures
In this episode of Funded, Alex welcomes Kristina Chapple, General Partner at 11 Tribes Ventures, for a candid conversation about reshaping early-stage venture capital. Kristina, recently recognized on Forbes 30 Under 30 and Chicago Innovations 25 Under 25 lists, offers insight into how 11 Tribes...
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Secrets from Subscript's Fundraise Journey | Sidarth Kakkar, Subscript
In this episode of the Funded, Alex sits down with Sidharth Kakkar, the founder of Subscript, to discuss his journey in raising a $15 million Series A round. The conversation spans various aspects of fundraising, including Sidharth's approach to crafting a compelling narrative for investors, the...
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How to Scale to $100M ARR with a 3-Person Finance Team | Riya Grover, Sequence
Riya Grover, Cofounder and CEO of Sequence, breaks down how AI-powered revenue automation is transforming finance operations for high-growth startups. Companies like Cognition, Deel, and MoonPay are scaling to 9 figures with finance teams of just 3-5 people—and Riya explains exactly how they're...
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ABOUT THIS SHOW
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.
HOSTED BY
airCFO
CATEGORIES
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Frequently Asked Questions
How many episodes does The AI CFO with Alex Wittenberg have?
The AI CFO with Alex Wittenberg currently has 22 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is The AI CFO with Alex Wittenberg 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...
How often does The AI CFO with Alex Wittenberg release new episodes?
The AI CFO with Alex Wittenberg has 22 episodes. Check the episode list to see recent publication dates and frequency.
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You can listen to The AI CFO with Alex Wittenberg on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts The AI CFO with Alex Wittenberg?
The AI CFO with Alex Wittenberg is created and hosted by airCFO.
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