"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
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.
Sep 5, 2025 • 40min
E55: First Round and YC-Backed Startup 'Eliminating Business Bullshit' | Josh Wymer, CEO of CentralHQ
Josh Wymer, Co-founder and CEO of Central HQ, shares insights on revolutionizing business operations with AI. He discusses raising $8.6 million from First Round Capital and Y Combinator to streamline back-office tasks through Slack-based automation. The conversation reveals how AI can alleviate the burdens of payroll and compliance for startups, highlighting the importance of trust and transparency in automation. Wymer also emphasizes the need for emotional branding and differentiation in the competitive finance sector, ensuring businesses stay agile and efficient.
Aug 27, 2025 • 38min
E54: Filling the Gap Between QuickBooks and NetSuite with SoftLedger CEO Ben Taylor
Ben Taylor, CEO and Co-founder of SoftLedger, offers insight into revolutionizing accounting with his API-first general ledger. He discusses his journey from personal challenges to creating a solution for businesses outgrowing QuickBooks. The conversation highlights the integration of AI in accounting, emphasizing its potential to streamline complex processes while maintaining user-friendly interfaces. Taylor also shares innovative approaches to fundraising, shifting from traditional models to customer-driven strategies that underscore the importance of client satisfaction in tech finance.
4 snips
Aug 6, 2025 • 38min
E53: How AI Agents are Replacing Manual Accounting Work with Truewind CEO Alex Lee
Join Alex Lee, the co-founder and CEO of Truewind, a pioneer in AI-powered accounting. He discusses how Truewind's technology is revolutionizing traditional accounting by cutting data reconciliation time from hours to minutes. Alex shares insights on the adoption of AI in the industry, the challenges of fundraising in a tough climate, and how customer feedback drives innovation. He also highlights the importance of retaining human oversight in finance, emphasizing that AI enhances accountants' roles rather than replacing them.
4 snips
Jul 30, 2025 • 37min
E52: Building a Viral Contract Platform: Will Hubbard, CEO of Agree
Will Hubbard, Founder & COO of Agree, dives into the creation of a game-changing platform that integrates contracting, invoicing, and payments seamlessly. He shares insights on Agree's rapid growth and the impact of their recent $7.2M seed round. The conversation highlights the importance of user-centered design in finance tech and how AI is reshaping the industry. Hubbard also reveals how their platform simplifies the contracting process, turning tedious tasks into delightful user experiences, and discusses the significance of fostering customer empathy in product development.
