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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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E47: Agentic Commerce, Stablecoins, and Global Trends with Cindy Turner, CPO of Worldpay
June 12, 2025

E47: Agentic Commerce, Stablecoins, and Global Trends with Cindy Turner, CPO of Worldpay

This week, Sasha Orloff and Worldpay Chief Product Officer Cindy Turner explore the shifting digital payments landscape—from stablecoins and agentic tech to global trends in account-to-account payments, regional behaviors, re...
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E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze
May 21, 2025

E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze

In this episode, Sasha Orloff talks with Jean-Denis Greze, Co-founder and CEO of Town, about building an AI-powered tax solution for SMBs, exploring the startup’s origin, the balance between automation and human expertise, st...
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E45: Artisan: Stop Hiring Humans, with Jaspar Carmichael-Jack
April 30, 2025

E45: Artisan: Stop Hiring Humans, with Jaspar Carmichael-Jack

This week, Sasha Orloff sits down with Jaspar Carmichael-Jack, Founder & CEO of Artisan, about how their AI employees like Ava are transforming sales and workflows by integrating software into cohesive ecosystems, highlightin...
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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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