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Sasha Orloff

CEO of Puzzle and host of the Turpentine Finance podcast. YC, ODF, Village Global alumni.

Sasha Orloff is the host of the "Turpentine Finance" podcast and the CEO of Puzzle, a modern accounting platform with an AI-first ledger.12 He is an alumnus of Y Combinator (YC), On Deck Fellowship (ODF), and Village Global.2

The "Turpentine Finance" podcast, which is part of the Turpentine podcast network, features Sasha interviewing CFOs, founders, and finance leaders from top tech companies.13 The podcast covers major tech finance news, including funding announcements, deals, product launches, and emerging players shaping B2B fintech.1 It also explores how finance leaders are implementing AI in their work.1

Sasha's podcast discussions often touch on topics such as M&A, market downturns, macroeconomics, product-market fit, fundraising, financial forecasting, headcount, and equity.3 The show aims to provide insights into decision-making processes and mental models that can be applied during high-pressure situations.3

As of February 2025, the podcast has been active for about two years, with 37 episodes released.1 Sasha's LinkedIn username is indeed sashaorloff, where he shares professional insights and updates about his work in the tech finance space.245

Highlights

Mar 21 · twitter

It won’t be an accrual world for accounting.

Feb 16 · twitter

At a QuickBooks all-hands meeting, somebody said this:

Accountants would become the Uber drivers of AI.

The software that 85% of small business accountants rely on every day, their primary tool, is telling its employees that those same accountants are about to become irrelevant.

Then they launched an accounting services business.

Started competing directly with accountants.

Turning accountants into the Uber.

So your software partner, the one you built your entire practice around, is now your competitor. And they're using AI to do it.

We're building Puzzle with the opposite thesis.

Not AI to replace accountants. But AI to make accountants more valuable. We're not here to take away their money. We're here to help them make more money.

The accountants I talk to feel this tension.

They just don't always say it out loud.

Their most important software vendor is actively trying to make them obsolete.

If your software partner started competing with you tomorrow, how would you respond?

At a QuickBooks all-hands meeting, somebody said this:

Accountants would become the Uber drivers of
Dec 19 · podcasts.apple.com
"Turpentine Finance" with Sasha Orloff - Apple Podcasts
"Turpentine Finance" with Sasha Orloff - Apple Podcasts
Aug 22 · podpage.com
Season 1 | "Turpentine Finance" with Sasha Orloff - Podpage

Related Questions

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Who are some of the notable guests Sasha Orloff has interviewed on his podcast?
How does Sasha Orloff choose his guests for the Turpentine Finance podcast?
What are some key topics Sasha Orloff covers in his podcast?
How has the Turpentine Finance podcast evolved since its inception?
Sasha Orloff
Sasha Orloff, photo 1
Sasha Orloff, photo 2
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Location

San Francisco, California, United States