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

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

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.io Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co

  1. Using AI and Humans to Fix Accounting w/ Matt Tait, CEO of Decimal

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    Using AI and Humans to Fix Accounting w/ Matt Tait, CEO of Decimal

    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/ Found Found 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

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  2. From Quill to AI: The Evolution of Accounting with David Hartley, former CIO and CPA

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    From Quill to AI: The Evolution of Accounting with David Hartley, former CIO and CPA

    In the final episode of season one, Sasha Orloff is joined by David Hartley, a seasoned CPA with over 30 years of experience, as they explore the evolution of accounting from the 15th century to today's AI-driven landscape and discuss how the profession adapts to technological change while preserving its core value of trust. — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — Highlights from the Episode: Accounting profession is facing its most significant period of change, with AI and automation creating both challenges and opportunities for practitioners at all levels. There's currently a major pipeline issue in accounting - with 75% of CPAs approaching retirement age and not enough new talent entering the field. Despite technological advances, the fundamental need for trust and human interpretation in accounting remains paramount, suggesting AI will augment rather than replace accountants. — RECOMMENDED PODCAST: Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution. Apple: https://podcasts.apple.com/us/podcast/id1786227593 Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg YouTube: https://www.youtube.com/@ModernRelationshipsPod -- SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: https://www.linkedin.com/in/davehartley/ — X/SOCIAL: @sashaorloff (Sasha)

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  3. How to Not Be in the Bottom 90% of Acquisitions with Andrew Gazdecki

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    How to Not Be in the Bottom 90% of Acquisitions with Andrew Gazdecki

    In this episode, Sasha Orloff is joined by Andrew Gazdecki, founder of Acquire.com, who shares his expertise on successfully selling companies, maximizing exit value, and key lessons from his own acquisition experiences, with over $500 million in closed deals. — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — Highlights from the Episode: Creating a competitive process with multiple potential buyers is crucial for maximizing exit value - "if you have one buyer, you have no buyer" Proper preparation and documentation (clean financials, confidential information memorandum) significantly speeds up the acquisition process and builds buyer confidence Being transparent about business challenges upfront ("bruises and all") builds trust and allows you to control the narrative around potential objections -- RECOMMENDED PODCAST: Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution. Apple: https://podcasts.apple.com/us/podcast/id1786227593 Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg YouTube: https://www.youtube.com/@ModernRelationshipsPod — SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: Acquire: https://acquire.com/ https://www.linkedin.com/in/agazdecki/ — X/SOCIAL: @acquiredotcom (Acquire) @agazdecki (Andrew) @sashaorloff (Sasha) — TIMESTAMPS: (00:00) Intro (02:10) Personal lessons from selling Business Apps (03:50) Building Acquire.com from personal experience (06:49) First acquisition story with ESW Capital (09:28) Negotiating terms and tax considerations (12:20) Story of Altcoin acquisition (13:53) Sponsor: Notion (15:15) Experience at Spiff and path to Acquire.com (18:35) Maximizing exit value strategies (25:47) Process of listing on Acquire.com (27:36) Types of buyers and deal sizes (29:34) Success stories and notable deals (32:57) Future plans for Acquire.com (34:04) Wrap

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  4. AI Finance Agents & The CHARGE Framework: JustPaid's Vision for Modern AR

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    AI Finance Agents & The CHARGE Framework: JustPaid's Vision for Modern AR

    This week, Sasha Orloff sits down with JustPaid founders Daniel Kivatinos, a successful YC founder behind the first iPad medical records company, and Anelya Grant, a Kazakhstan immigrant who built an accounting practice for YC startups, about how their unique backgrounds inspired them to tackle the critical challenge of accounts receivable automation with an AI-powered platform. For full show notes, visit: https://highlightai.com/share/309bb91f-34ee-4052-88e5-28718a9101da — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: Streamlining Accounts Receivable: Transforming an Overlooked Cornerstone of Business Operations: https://www.justpaid.ai/blog/streamlining-accounts-receivable JustPaid: https://www.justpaid.ai https://www.linkedin.com/in/kivatinos/ https://www.linkedin.com/in/anelya/ — X/SOCIAL: @getjustpaid (JustPaid) @danielkivatinos (Daniel) @sashaorloff (Sasha)

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  5. Growth Levers: A PayPal Veteran's Guide to Startup Success | Matt Lerner on the CRAFTED. Podcast

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    Growth Levers: A PayPal Veteran's Guide to Startup Success | Matt Lerner on the CRAFTED. Podcast

    Today, we’re sharing a special episode from our friends at the Webby Awards-honored CRAFTED. podcast. In this conversation, Dan Blumberg interviews growth expert, SYSTM founder, and former PayPal leader Matt Lerner about his book 'Growth Levers,' offering actionable strategies for startups to identify the 10% of efforts that drive 90% of growth. They discuss common startup pitfalls, the mindset shift to customer-centric thinking, JTBD-style interviewing, and the importance of rapid experimentation. For full show notes, visit: https://highlightai.com/share/af10e152-f30a-403e-805f-d234eb40109a — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — Check out Dan Blumberg's CRAFTED. where he interviews founders of high growth startups, including from Lattice, Gusto, Moov, Monte Carlo, Customer.io and our own Sasha Orloff! Apple: https://podcasts.apple.com/us/podcast/crafted-the-tech-podcast-for-founders-makers/id1649355311 Spotify: https://open.spotify.com/show/3xtU2V1jRP89aI1ULRN2GI?si=b5753bd5be14494c — SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: Matt Lerner's company: https://www.systm.co/ CRAFTED. podcast: https://crafted.fm Growth Levers: https://www.amazon.com/dp/173842622X — LinkedIn: Matt Lerner https://www.linkedin.com/in/matthewlerner/ Dan Blumberg https://www.linkedin.com/in/dblums/ Sasha Orloff https://www.linkedin.com/in/sashaorloff/

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  6. AI is Solving Finance’s Biggest Problem - And It’s Not What You Think, with Nicolas Boucher

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    AI is Solving Finance’s Biggest Problem - And It’s Not What You Think, with Nicolas Boucher

    This week, Nicolas Boucher, a finance influencer with nearly a million LinkedIn followers, shares his journey from corporate finance to becoming a content creator and educator, discuss the impact of AI on finance jobs, and how he uses platforms like LinkedIn to share valuable financial insights. For full show notes, visit: https://highlightai.com/share/af10e152-f30a-403e-805f-d234eb40109a — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — RECOMMENDED PODCAST: Unpack Pricing Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more. Apple: https://podcasts.apple.com/us/podcast/id1765716600 Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg — SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/product/ai?utm_source=podcasts&utm_medium=upstreampod — LINKS: AI Finance Club: https://ai-finance.club/ https://www.linkedin.com/in/bouchernicolas/ — X/SOCIAL: @BoucherNicolas (Nicolas) @sashaorloff (Sasha)

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  7. When 3.6 Million Users Need a New Home with Copilot Money's Andrés Ugarte

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    When 3.6 Million Users Need a New Home with Copilot Money's Andrés Ugarte

    This week, Sasha Orloff is joined by Andrés Ugarte to explore the rise of Copilot Money after Mint's shutdown announcement, sharing his journey from frustrated user to founder of a privacy-focused personal finance app, and discussing the challenges of building a product-driven company in a shifting financial landscape. For full show notes, visit: https://highlightai.com/share/31895f5b-d783-4eaa-ab11-ac3214b21ddb — RECOMMENDED PODCAST: Unpack Pricing Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more. Apple: https://podcasts.apple.com/us/podcast/id1765716600 Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg — SPONSOR: 🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. 💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial. 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/product/ai?utm_source=podcasts&utm_medium=upstreampod -- LINKS: Copilot Money: https://copilot.money/ https://www.linkedin.com/in/andresugarte/ -- X/SOCIAL: @chuga (Andrés) @sashaorloff (Sasha)

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  8. Paul Barnhurst (The FP&A Guy) on What CEOs Want from FP&A

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    Paul Barnhurst (The FP&A Guy) on What CEOs Want from FP&A

    In this episode of Turpentine Finance, host Sasha Orloff sits down with Paul Barnhurst, a passionate FP&A educator and content creator who shares insights on financial planning & analysis, teaching methodologies, and the evolution of financial tools. For full show notes, visit: https://highlightai.com/share/1823b417-abe8-49bb-8f00-d673e24077b1 -- 📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess  -- RECOMMENDED PODCAST: Unpack Pricing Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more. Apple: https://podcasts.apple.com/us/podcast/id1765716600 Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg SPONSOR: -- 🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. 💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial. -- LINKS: The FP&A Guy: https://www.thefpandaguy.com/ https://www.linkedin.com/in/TheFPandAGuy/ -- X/SOCIAL: @sashaorloff

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    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.io Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co

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