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PODCAST

"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

business management

All Episodes

39:52

E44: From $2B to $80B: Wealthfront CFO Alan...

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

2025/04/23

In this episode, Sasha Orloff is joined Alan Imberman, CFO of Wealthfront, about how a client-first philosophy, transparent access, innovative products like S&P 500 Direct Indexing, and strategic use of machine learning have helped Wealthfront grow to $80 billion in assets and 1 million customers, while delivering lower fees, better rates, and sustainable wealth-building strategies.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide

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44:06

E43: The CFO's Blockbuster vs Netflix Moment: AI...

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

2025/04/16

This week, Sasha Orloff is joined by Wouter Born, finance, AI influencer, and General Partner at Born Capital to discuss how AI is reshaping the CFO role and financial tech stack, drawing lessons from Netflix’s rise over Blockbuster, emphasizing innovation, practical AI adoption, and financial storytelling.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team

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41:27

E42: Can AI predict the next unicorn. Crunchbase says...

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

2025/04/09

This week, Sasha Orloff sits down with Megh Gautam, Chief Product Officer of Crunchbase, to explore the company’s evolution into an AI-driven intelligence platform, discussing its 95% unicorn prediction accuracy, AI-powered user experiences, pricing challenges, and insights for founders, investors, and job seekers.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps

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40:50

E41: Surprising Trends from Deel's Data with Ben Cohen

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

2025/04/02

This week, Sasha Orloff sits down with Ben Cohen, Head of Data from Deel to discuss the company's 2025 Global Hiring Report, covering trends in Gen Z salaries, rising demand for finance roles, global workforce management challenges, domestic hiring shifts, employee termination rates, and the tools Deel provides to support global hires, with an emphasis on trust and asynchronous decision-making for productivity.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace

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45:28

E40: The $500 Domain That Became a Multi-Million...

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

2025/03/27

This week, Sasha Orloff is joined by Kash Ali, Founder and CEO of TaxGPT, who shares how a personal tax issue led to the platform’s creation, its rapid growth after Greg Brockman’s GPT-4 demo, investor interest from Marc Cuban and Jason Calacanis, its shift from a consumer tool to a B2B AI assistant for accountants, its unique advantages over general AI, and his own journey from Pakistan to Silicon Valley, culminating in Y Combinator and a vision for the future of AI-driven tax

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35:23

E39: The AI Economy: How Agents Will Transact Without...

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

2025/03/19

This week, Sasha Orloff sits down with Donald Gossen, CEO of Nevermined, to explore the future of AI-driven payments, highlighting the company's vision for AI agents with independent accounts and transaction protocols, the challenges of dynamic payment systems, the role of blockchain in security, and Nevermined's journey in enabling decentralized AI-to-AI transactions.-- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From

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36:07

E38: AI-Powered Tax Solutions are Really Here, with...

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

2025/03/12

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: Notion Boost your startup with Notion—the

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48:43

Using AI and Humans to Fix Accounting w/ Matt Tait,...

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

2025/02/06

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

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51:50

E36: From Quill to AI: The Evolution of Accounting...

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

2024/12/19

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

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37:03

E35: How to Not Be in the Bottom 90% of Acquisitions...

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

2024/12/12

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

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52:19

E34: AI Finance Agents & The CHARGE Framework:...

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

2024/12/05

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

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37:54

E33: Growth Levers: A PayPal Veteran's Guide to...

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

2024/11/26

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

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48:32

AI is Solving Finance’s Biggest Problem - And It’s...

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

2024/11/21

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— RECOMMENDED PODCAST: Unpack Pricing Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and

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50:51

E31: When 3.6 Million Users Need a New Home with...

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

2024/11/14

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

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49:31

E30: Paul Barnhurst (The FP&A Guy) on What CEOs Want...

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

2024/10/31

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 -- SPONSOR: 🌎ANROK is the enterprise-grade

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56:00

E29: Bootstrapped to $640M: Brad Wiskirchen on M&A,...

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

2024/10/24

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:

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48:27

E28: Airbase CFO Aneal Vallurupalli on Acquisitions,...

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

2024/10/17

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 $325M 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

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51:54

E27: Architecting a Global Marketplace for M&A with...

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

2024/10/10

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, the leading platform for buying and selling online businesses. Blake shares insights from his career (Xero, Lonely Planet, Good44), and explains how Flippa operates as the ‘investment bank for the 99%,’ providing a marketplace for subscale business transactions. The episode dives into the opportunities presented by the marketplace, key deal characteristics, and the different buyer segments. They also discuss the importance

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46:12

E26: Why Finance Software is About to Change, with...

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

2024/10/03

In this episode, Sasha Orloff welcomes Jane Lee and Aditya Reddy of Sapphire Ventures to unpack their paper, “Rise of the Next Gen CFO,” which features a market map of CFO tools and identifies key trends and predictions. Jane and Aditya discuss how finance roles are transforming, the convergence of finance and data science, the influence of AI, and emerging investment strategies in this fast-paced sector.Nothing presented within this podcast is intended to constitute investment advice, and under

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53:16

E25: What Separates Good From Great Treasury, with...

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

2024/09/26

In this episode, Sasha Orloff is joined by Eugene Spevakov, the Treasurer and Head of Corporate FP&A at 6sense, treasury expert, and veteran CFO. Sasha and Eugene dive deep into the Treasury function: how it differs across industries, how a scaling startup will know when it’s time to hire for the role, how to structure the function, and what separates a great treasurer from merely good. Eugene offers a masterclass on leveraging treasury to drive growth, improve cash flow, and allocate risk

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