Funded with Alex Wittenberg

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.

Funded with Alex Wittenberg is a business podcast hosted by airCFO, with 21 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

airCFO hosts Funded with Alex Wittenberg, a business show with 21 episodes published.

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  Funded with Alex Wittenberg

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

  Jul 28, 20261h 2m

  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

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  Funded with Alex Wittenberg

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

  Jul 1, 202656 min

  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/ 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

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  Funded with Alex Wittenberg

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

  Jun 4, 202650 minS0

  <p>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.</p><p></p><p>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.</p><p></p><p>More about Oncology Ventures: https://oncology.ventures</p><...

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  Funded with Alex Wittenberg

  Community, AI, and Knowing When Not to Raise | Aileen Allen, Mercury Fund

  Apr 28, 202651 minS0

  <p>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.</p><p>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.</p><p><...

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  Funded with Alex Wittenberg

  The AI-Native Playbook for Raising a $3.7M Seed Round | Andy Keil, DreamBase

  Mar 3, 202658 minS0

  <p>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.</p><p></p><p>Subscribe to Funded for more conversations with founders on the real story behind startup fundraising. <br /></p><p>More about Dreambase: https://dreambase.ai/</p>

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