"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

Wouter Born, a finance and AI influencer and General Partner at Born Capital, shares insights on how AI is transforming the role of CFOs. He draws parallels between Netflix and Blockbuster, urging finance leaders to adapt to survive. Wouter discusses practical steps for AI integration, emphasizing the need for innovation and collaboration. He delves into the critical role of financial storytelling and how AI can enhance this narrative. The conversation highlights the evolving tech stack for CFOs and the importance of balancing innovation with data privacy.

Megh Gautam, Chief Product Officer at Crunchbase, shares insights on transforming the company into an AI-driven platform. They discuss the impressive 95% accuracy in predicting unicorn startups and how AI enhances user experience. Megh reflects on their journey from a math major to a tech leader, emphasizing the importance of data trust and user engagement. The conversation also addresses innovative pricing strategies and the future of data integration in accounting, showcasing how machine learning informs decision-making for founders and investors.

In this discussion, Ben Cohen, Head of Data at Deel, shares his expertise on global hiring trends and the impact of Generation Z on the workforce. He reveals surprising insights from Deel's 2025 Global Hiring Report, including the rising demand for finance roles and the shift towards domestic hiring. The conversation also touches on the challenges of managing a distributed workforce and the innovative tools that enhance collaboration and productivity, emphasizing the importance of trust in asynchronous decision-making.

Kash Ali, Founder and CEO of TaxGPT, shares his inspiring journey from Pakistan to Silicon Valley, ignited by a personal tax dilemma. He reveals how a simple domain purchase transformed into a multi-million dollar B2B AI assistant for accountants following a GPT-4 demo. The discussion highlights the platform's unique advantages in compliance and data security, its evolution from a consumer tool, and the impact of Y Combinator on his success. Kash envisions a future where AI simplifies tax solutions, redefining accounting and tax compliance.

Donald Gossen, CEO of Nevermined and a veteran in AI and machine learning, discusses the future of AI-driven payments and the concept of AI agents acting as independent economic entities. He dives into the challenges and innovations of dynamic payment systems and the transformative potential of blockchain in enhancing transaction security. Gossen also shares insights on how these intelligent agents will reshape commerce, facilitating automated transactions and financial decision-making, marking a revolutionary shift in the fintech landscape.

This week, Sasha Orloff is joined by Ankur Dahiya, CEO and founder of Fifteenth, a B2B fintech startup using AI to modernize the tax industry, as they discuss his journey from navigating complex stock options at Flexport to transforming CPA services, the challenges of scaling a tax-focused business, the role of AI in automating tax processes, and his vision for more efficient, accessible tax advisory following a successful funding round.--SPONSORS: NotionBoost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzlePuzzle📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/--RECOMMENDED IN THIS EPISODE:https://www.linkedin.com/in/ankurdahiya/https://www.fifteenth.com--X/SOCIAL:@sashaorloff (Sasha)@ankurd (Ankur)--TIMESTAMPS:(00:00) Intro(01:37) Guest Introduction: Ankur Dahiya(02:24) Problem with taxes(03:01) Birth of Fifteenth(08:33) Combining human expertise with AI(12:22) Future of AI in tax solutions(14:40) Sponsors: Notion | Puzzle(16:03) Managing personal finances(19:42) Fundraising and building the team(25:49) Challenges and advice for founders(27:55) Tax tips for founders and engineers(33:12) Wrap

In this first episode of Season 2, Sasha Orloff is joined by Matt Tait, CEO of Decimal, to discuss the rise of AI in accounting, Decimal’s recent acquisition of KPMG Spark, and their new strategic partnership with Puzzle. Matt also covers his journey building Decimal, the balance of human expertise in a tech-driven world, and the industry’s future.--SPONSORS: Puzzle📈  No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/FoundFound provides small business owners tools to track expenses, calculate taxes, manage cashflow, send invoices and more. Open a Found account for free at https://found.com/econ102--RECOMMENDED IN THIS EPISODE:https://www.linkedin.com/in/mtait83/https://www.decimal.com/--X/SOCIAL:@GoDecimal (Decimal)@sashaorloff (Sasha)--TIMESTAMPS:(00:00) Intro(00:59) Season 2 changes(01:48) Exciting times in accounting(03:12) Interview with Matt Tate, CEO of Decimal(04:22) Rise and fall of Bench(06:18) Challenges in the accounting industry(13:03) Founding and vision of Decimal(16:46) Sponsors: Puzzle | Found(18:34) Acquisition of KPMG Spark(23:11) Team collaboration and roadmap insights(23:45) Scaling with Puzzle's AI native ledger(24:31) Evaluating technology partnerships(28:59) Role of trust and accountability in accounting(29:43) AI's impact on client experience(31:08) Human interaction vs. full automation(36:22) Future of AI in accounting(43:34) Implementing AI tools at scale(45:14) Wrap

David Hartley, a seasoned CPA and former CIO, dives into the fascinating evolution of accounting from quill to AI. He discusses the critical role technology plays in the profession today, noting the major challenges and opportunities posed by AI and automation. With 75% of CPAs nearing retirement, he highlights a looming talent gap in the field. Despite advancements, Hartley emphasizes the unwavering importance of trust and human insight, positioning AI as a partner rather than a replacement in the accounting landscape.

In this conversation, Andrew Gazdecki, founder of Acquire.com, draws from his impressive experience in facilitating over $500 million in successful exits. He emphasizes the importance of creating a competitive bidding process and how having multiple buyers enhances exit value. Andrew discusses the necessity of thorough preparation and transparent communication about business challenges to build trust. He also touches on the financial advantages of Qualified Small Business Stock and adapts to changing regulations in the evolving crypto landscape.

In this discussion, co-founders Daniel Kivatinos, a pioneer in iPad medical records, and Anelya Grant, a former YC accountant from Kazakhstan, delve into their revolutionary platform JustPaid. They explore the challenges in accounts receivable management and introduce the CHARGE framework to streamline billing processes. The duo shares their personal journeys of innovation, emphasizing the transformative potential of AI finance agents in startups. Listeners will gain insights into enhancing financial communication and operational efficiency with cutting-edge technology.