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.

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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

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RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/mtait83/

https://www.decimal.com/

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X/SOCIAL:

@GoDecimal (Decimal)

@sashaorloff (Sasha)

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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

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.

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🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

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Highlights from the Episode:

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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

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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

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LINKS:

https://www.linkedin.com/in/davehartley/

—

X/SOCIAL:

@sashaorloff (Sasha)

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:

--

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

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/

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X/SOCIAL:

@getjustpaid (JustPaid)

@danielkivatinos (Daniel)

@sashaorloff (Sasha)

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

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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/

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

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🙏 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)

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)

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

In this episode, host Sasha Orloff interviews Brad Wiskirchen about his journey with Kount, the AI-driven fraud prevention company he bootstrapped and sold to Equifax for $640 million, while sharing insights from his experience as a founder and now a partner at CVC Capital Partners. For full show notes, visit: https://highlightai.com/share/eec1be56-ae04-4afc-bb24-7ed8523b2176

--

📰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:

Kount: https://kount.com/

https://www.linkedin.com/in/bradwiskirchen/

--

X/SOCIAL:

@sashaorloff

@KountInc

In this episode, Sasha Orloff is joined by Aneal Vallurupalli, CFO at Airbase, who drops insights on modern spend management and his journey from M&A to leading finance at a Paylocity acquisition target. Aneal discusses his career trajectory, the impactful role of a CFO in spend management, and how Airbase revolutionizes non-payroll spends in the AI era. Aneal also offers essential advice to CFOs navigating today’s dynamic financial landscape.

🔥 Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

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SPONSORS:

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. Trusted by Notion, Anthropic, and Vanta. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

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LINKS:

Airbase: https://www.airbase.com/

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X/SOCIAL:

@sashaorloff

@AVallurupalli

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TIMESTAMPS:

(00:00) Preview

(01:16) Intro

(01:43) Meet Aneal Vallurupalli, CFO of Airbase

(02:28) Understanding Airbase's spend management

(04:33) Aneal’s journey to Airbase

(08:08) Evolution and impact of Airbase

(09:43) Role and strategy as CFO

(17:34) Sponsor: Anrok

(18:59) Balancing flexibility and control in spend management

(21:36) Importance of change management

(23:58) Memorable customer success stories

(27:35) Evolution of software in the CFO's office

(31:21) Trends in selling to different industries

(37:08) Future of Airbase and business spend management

(39:36) Insights on M&A and career journey

(43:37) Reflections on buy-side and sell-side experiences

(45:39) Wrap