Funded with Alex Wittenberg

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...

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 imp...

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 t...

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 de...

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...

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 a...

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...

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...

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 revenue accounting pain points. The conversation explores Tabs' new AI agents for billing and collections,...

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 examples from Hustle Fund's 620-company portfolio.

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 for colon cancer. What makes this story incredible is Scott's resilience in fundraising for a startup at...

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 million Series B led by Andreessen Horowitz just three months later. The company doubled ARR in 12 week...

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 approach, explaining that they invest in ideas they would be passionate about building themselves. As f...

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 business, highlighting the complexities of early go-to-market strategy, landing initial flagship customer...

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 both an operator and investor shapes Las Olas’s approach and commitment to supporting founders beyond j...

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 founders looking to tackle their next fundraise. Nick brings both deep investment experience and operation...

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 million pre-seed round, led by Harlem Capital in mid-2023. Taher walks listeners through the granular deta...

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 goes beyond financial metrics to focus on the well-being and resilience of founders. Rather than just...

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 importance of finding believers rather than trying to change investment perspectives, and the nuances o...

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 doing it. Riya also reveals the behind-the-scenes story of Sequence's Series A fundraise: how they lande...