Funded with Alex Wittenberg

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.comWe 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.

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, plus Ali's 4-step framework for building production-ready AI agents in finance. He explains why finance teams have historically blocked new revenue streams and how modern tools are changing that dynamic.Ali also discusses the evolution of CFO roles in an AI-driven world, arguing we're not heading toward zero-person finance organizations but rather strategic finance teams with superpowers. He shares tactical fundraising advice accumulated over 3 years building Tabs, including the importance of running compressed funding processes and leveraging founder introductions.

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 the intersection of three notoriously difficult sectors for VC funding: consumer, healthcare, and hardware. He pitched over 130 investors to raise his 4M seed round, with some literally telling him in the first 30 seconds they would never invest but just wanted to hear the pitch for entertainment.Scott shares his meticulously organized fundraising system, including his detailed spreadsheet tracking 250+ investors and his decision to isolate himself in San Francisco for 2.5 months until he closed the round. The conversation includes amazing war stories like booking same-day flights to Boston to recruit their CTO and accidentally ending up at a black-tie Crohn's gala in tuxedos with 90-minute notice.

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 weeks after their Series A, supporting over 200 companies with an unprecedented NPS score of 71 for accounting software. Nicolas explains the strategic decision to take a preemptive Series B offer rather than wait, the importance of building investor relationships before fundraising, and why compressed fundraising timelines work when you have strong commercial traction.

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 former founders, they prioritize scrappiness and intellectual honesty in a team, viewing these traits as key indicators of success. He shares a candid look at their due diligence process, emphasizing that while data and market size are crucial, the most critical factor is a founder's ability to be open about their company's challenges. Jed also offers invaluable advice for founders, highlighting the importance of iterating on their pitch, seeking honest feedback, and building a strong, trusting relationship with potential investors.The conversation also dives deep into the most pressing topic in venture today: AI. Jed explains why Javelin is wary of "copycat" businesses that can be replicated in a weekend and what a truly defensible AI-powered company looks like. He discusses how the rapid pace of AI development is shifting the investment landscape, favoring companies that can achieve significant progress with a small team and minimal capital.

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 customers, and getting pricing right. Both she and Alex explore how early foundational decisions—especially operational shortcuts—can add up as operational debt, potentially causing bigger problems as a company begins to scale.The conversation goes into depth on Glasswing Ventures’ approach as a thesis-driven, early-stage fund focused on AI-native companies, particularly in enterprise verticals such as supply chain, financial services, and cybersecurity. Rudina explains that while AI enablement has become table stakes for modern startups, true differentiation comes from building AI-native solutions that tackle previously unsolvable problems and create orders-of-magnitude improvements for their customers. She details Glasswing’s hands-on investment and diligence process, the importance of founder execution over just market opportunity, and how their deep advisor network and operational support help startups go from idea to market leader.

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 just providing capital.The conversation dives deep into Las Olas Venture Capital’s investment philosophy, focusing specifically on early-stage B2B software startups. Mark explains that while market size and demand are crucial, LOVC prioritizes founders who demonstrate strong execution skills, possess sector expertise, and can present realistic, well-constructed financial models and business plans. He stresses the importance of being fully prepared before meeting with investors—having all relevant documents ready can make or break a deal—and highlights that delays and lack of preparation are common red flags during the diligence process.

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 operational expertise in AI, machine learning, and data infrastructure to the discussion. With Differential Ventures having raised over $100 million across three funds and making over 40 investments, Nick is able to offer a rare perspective from both sides of the table.In this conversation, Nick reveals his firm's investment philosophy, prioritizing a startup's value proposition and team, especially at the seed stage. He outlines their stringent process, sifting through 5,000 annual opportunities to make 8-10 investments, emphasizing founder-market fit and defensible moats in competitive, AI-driven sectors. Nick also discusses their hands-on post-investment approach and advises founders to build genuine relationships with VCs and not be overly secretive with their ideas, highlighting VCs' collaborative nature. His insights provide a valuable playbook for navigating venture fundraising, particularly in the rapidly evolving AI landscape.

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 details of the fundraising process, sharing candid advice and tactics. He discusses building an investor list of 50-70 firms, the importance of leveraging personal networks versus relying on cold outreach, and tactics for keeping track of investor conversations—he used nothing more than Google Sheets. Taher also underscores the value of addressing potential investor concerns head-on, recommending founders proactively frame points of contention (like DocDraft’s differentiation from tools such as ChatGPT) rather than hoping those issues go unnoticed. The episode offers behind-the-scenes insight into crafting compelling narratives, evaluating lead investors, and even tactical advice for running a process-driven, time-bound fundraise.

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 measuring success through exit valuations or growth rates, Kristina highlights the importance of evaluating founder outcomes, such as the health of personal relationships, mental and physical health, and the sustainability of the entrepreneurial journey. Throughout the episode, Kristina and Alex explore the shortcomings of the traditional VC model, especially its tendency to overlook the human side of entrepreneurship. They discuss the evaluation process at 11 Tribes, which includes founder personality assessments and prioritizes qualities like intensity and sober-mindedness in addition to financial acumen.

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 of the delicate relationship between a founder and investors.Throughout the discussion, Alex and Sidharth emphasize the iterative nature of developing a fundraising strategy and the need to leverage the founder community for guidance. Sidharth's background as a second-time founder informs much of his approach to strategically growing Subscript and successfully navigating the venture capital landscape. This episode offers rich insights for first-time founders aiming to secure venture funding.

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 landed multiple term sheets in just 3 weeks and what investors really want to see beyond the "AI" buzzword. She shares why human-in-the-loop design is the difference between AI that works and AI that creates chaos, plus her framework for building agents that actually integrate into enterprise workflows.Whether you're building in the AI space, thinking about your next fundraise, or trying to scale your finance operations, this conversation is packed with actionable insights from someone who's doing it at the highest level.Links & Resources:• Learn more about Sequence: https://www.sequencehq.com/• Check out airCFO: https://www.aircfo.com/Subscribe to Funded for more conversations with founders who are building the future of business.