"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
Puzzle, Turpentine
On Tech Finance, host Sasha Orloff brings you inside the office of the CFO - covering major tech finance news including funding announcements, deals, product launches, and emerging players shaping B2B fintech. We break down the week's biggest developments in finance tech and accounting, and explore how finance leaders are putting AI to work.Tech Finance is brought to you by Puzzle, the modern accounting platform with an AI-first ledger, built for speed, automation, and real time decision making. Learn more: puzzle.ioTech Finance is part of the Turpentine podcast network. Learn more: turpentine.co
Episodes
Mentioned books
Jan 14, 2026 • 36min
E65: a16z-backed Stuut CEO Tarek Alaruri on Why Legacy AR Software Failed and How AI Fixes It
Tarek Alaruri, CEO and co-founder of Stuut, leads an AI-powered accounts receivable platform that automates multiple AR functions. He discusses the shortcomings of legacy software and how Stuut’s solution drastically reduces days sales outstanding (DSO) by 40%. Tarek also emphasizes the importance of human-in-the-loop training to fine-tune AI responses and shares insights on fundraising from Andreessen Horowitz, addressing the evolving role of AR teams in managing client relationships rather than routine tasks.
12 snips
Jan 7, 2026 • 36min
E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"
Sam Ross, founder and CEO of Numeral and ex-product leader at Teespring and Airbnb, discusses his decision to pivot from a profitable venture to launch an AI-driven sales tax automation platform. He shares insights on the boring yet vital nature of sales tax compliance, the impact of a pivotal Supreme Court ruling, and how AI transforms traditional processes. With gripping anecdotes from his e-commerce experiences, Ross elaborates on the complexities of government systems and the challenges of navigating funding rounds, revealing the potential for smarter tools in automating tax solutions.
10 snips
Dec 17, 2025 • 48min
E63: Reverse Engineering Venture Capital with Metal's Usman Gul
Usman Gul, Founder and CEO of Metal, discusses his journey of creating an AI-driven fundraising operating system. He shares insights on avoiding common fundraising mistakes and the importance of targeted investor selection based on data. The conversation delves into the principles of effective fundraising, AI's role in storytelling, and evolving market dynamics that affect founders today. Usman offers practical advice for first-timers, emphasizing thorough preparation and relationship intelligence in securing funding.
9 snips
Dec 10, 2025 • 41min
E62: From Divvy FP&A to Parallel Founder: How Renato Villanueva Built the Tool Finance Actually Wants
Renato Villanueva, Founder and CEO of Parallel, shares his journey from FP&A professional at Divvy to launching an AI-driven financial planning tool. He discusses the critical challenges that fueled his startup creation and how nurturing investor relationships helped him secure $2.4 million in funding. Renato reveals how Parallel empowers founders to overcome common mistakes in hiring and revenue growth, elevating their financial decision-making. He emphasizes building meaningful tools over mere functions to truly meet startup needs.
Dec 3, 2025 • 38min
E61: Maxima's $41M Mission: Automating Enterprise Accounting Close with AI
Join Yogi Goel, Co-founder and CEO of Maxima, an AI-centric enterprise accounting startup, as he shares insights from his two decades in finance. Discover how Maxima raised $41 million to revolutionize accounting by automating journal entries and reconciliations, closing books 2-3 days faster with up to 98% automation. Yogi discusses the struggles accountants face and the need for AI to take on mundane tasks, allowing professionals to focus on strategic roles. Plus, he offers valuable advice for CFOs hesitant about adopting AI.
18 snips
Nov 20, 2025 • 45min
E60: Deel's COO on Scaling to $17.3B Valuation (and Where They Go From Here)
Dan Westgarth, COO of Deel, shares his expertise in scaling operations that drive a $17.3B valuation and manage payroll across 150 countries. He discusses lessons from his time at Revolut, focusing on first-principles thinking and decentralized decision-making. Westgarth highlights the importance of automation in global payroll and shares strategies for onboarding and customer success. He predicts a future with real-time payroll and fewer vendor dependencies, aiming for a seamless experience for employees and employers alike.
Nov 12, 2025 • 38min
E59: Why AI Tax Tools Fail the QSBS Test, with Nick Abouzeid of Rivet
Discover the innovative approach Rivet takes in modern tax services, combining expert practitioners with cutting-edge software. Hear about the challenges faced by traditional firms and how Rivet's model enhances responsiveness and efficiency. Nick Abouzeid shares insights on the interplay between AI and human judgment in tax work, the reasons behind raising venture capital, and the importance of international hiring for quality service. Learn why clients are switching to Rivet for improved support and how the firm’s fixed-pricing model is transforming the industry.
Oct 24, 2025 • 38min
E58: The future of M&A is AI? With Blake Hutchison, CEO of Flippa
Blake Hutchison, CEO of Flippa, leads the charge in transforming online business transactions with Lauren AI, an innovative tool designed to enhance deal sourcing and outreach. He discusses how AI is reshaping the M&A landscape, making it easier for small entrepreneurs to buy and sell businesses. Blake shares insights on how Lauren AI matches buyers with off-market opportunities, streamlines deal structures, and automates outreach efforts, all while ensuring that human relationships remain central to the process. The future of M&A is indeed looking bright!
Sep 25, 2025 • 56min
E57: Lessons from Brex, SVB, a16z: How Jason Mok Spots What Founders Need Before They Know It
In this discussion with Jason Mok, VP & GM of Startups at Brex, we dive into Brex's evolution from credit card services to a full-fledged financial platform. Jason shares insights on how Brex simplifies startup onboarding with innovative features like one-click accounting, seamlessly integrating with Puzzle for real-time bookkeeping. He reflects on his time at Silicon Valley Bank and how its culture shaped his approach to supporting founders. The conversation highlights the importance of proactive financial infrastructures in scaling startup success.
Sep 17, 2025 • 43min
E56: 5,000 Startups Later: Tax Lessons Every Founder Needs with Joe Faris
Joe Faris, founder of Accountalent and a veteran in helping over 5,000 startups, shares invaluable insights from his 40 years of experience. He discusses essential tax strategies, emphasizing the importance of 83B elections and timely compliance to avoid costly mistakes. Joe also highlights payroll challenges startups face when hiring across state lines and shares tips on maintaining robust bookkeeping practices. His expert advice empowers founders to navigate the complex world of taxes and finance with confidence.
