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"Turpentine Finance" with Sasha Orloff

A podcast where Sasha Orloff talks to founders and finance leaders at the best tech companies about what it takes to architect success. Our guests speak candidly about big business inflections, market curveballs and how they approach decision-making to tease out tactics and mental models you can use for when the pressure is on. You’ll hear stories from Instacart, Mercury, OpenAI, Andreessen-Horowitz, Netflix, Runway, and more.

Topics frequently touched upon M&A, Market Downturn, Macro, PMF, Fundraising, Financial Forecasting, Headcount, Equity.

Recent Episodes

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E44: From $2B to $80B: Wealthfront CFO Alan Imberman’s 10-Year Journey
April 23, 2025

E44: From $2B to $80B: Wealthfront CFO Alan Imberman’s 10-Year Journey

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 ...
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E43: The CFO's Blockbuster vs Netflix Moment: AI Adoption with Wouter Born
April 16, 2025

E43: The CFO's Blockbuster vs Netflix Moment: AI Adoption with Wouter Born

This week, Sasha Orloff is joined by Wouter Born, a 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 Bl...
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E42: Can AI predict the next unicorn. Crunchbase says yes with 95% accuracy.
April 9, 2025

E42: Can AI predict the next unicorn. Crunchbase says yes with 95% accuracy.

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 u...
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E41: Surprising Trends from Deel's Data with Ben Cohen
April 2, 2025

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

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 chal...
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E40: The $500 Domain That Became a Multi-Million Dollar AI Tax Assistant with Kash Ali of TaxGPT
March 27, 2025

E40: The $500 Domain That Became a Multi-Million Dollar AI Tax Assistant with Kash Ali of TaxGPT

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 Cuba...
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The AI Economy: How Agents Will Transact Without Us, with Don Gossen CEO of Nevermined
March 19, 2025

The AI Economy: How Agents Will Transact Without Us, with Don Gossen CEO of Nevermined

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 ch...
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