E65: a16z-backed Stuut CEO Tarek Alaruri on Why Legacy AR Software Failed and How AI Fixes It
In this episode, Sasha Orloff speaks with Tarek Alaruri, CEO and Co-founder of Stuut, about raising a Series A from Andreessen Horowitz to build an AI-powered accounts receivable platform that automates the entire AR function—from credit and collections to cash application and disputes—delivering a…
E66: Engineering the Modern Accounting Firm with Greg Capitolo of Attivo Partners
In this episode, Sasha Orloff speaks with Greg Capitolo, Co-founder and Partner at Attivo Partner, to discuss how fractional finance teams are transitioning from manual bookkeeping to AI-driven advisory roles, emphasizing the shift toward "real-time data-driven decision making" over traditional mon…
E67: Navigating the Era of "AI Slop" in Accounting with Luke Frye
In this episode, Sasha Orloff sits down with Luke Frye, founder of LukeFrye.co, to trace his decade-long journey through foundational fintech pioneers like Bench and Pilot and explore how AI is shifting the accountant's role from manual data entry to "architecting" financial systems and human-centr…
E68: Jeff Grimes of Perplexity on the New AI-Native Analyst
Sasha Orloff and Jeff Grimes, Perplexity’s Product Lead for Finance, explore the evolution of search from a simple "answer engine" to a high-stakes "action engine." They discuss the disruption of legacy platforms like the Bloomberg Terminal and how Perplexity is building an AI-native operating syst…
E69: Agentifying the $7 Trillion Tax Payment Network with Solon Angel of Remitian
Sasha Orloff sits down with Solon Angel, CEO of Remitian, to explore why tax payments remain one of fintech's most overlooked infrastructure problems. They discuss the outdated systems still powering tax compliance, how AI agents are enabling a new payments layer for accountants and taxpayers, and …
[SaaS & AI Series] Reinventing Accounting in the AI Agent Era With Sasha Orloff
![[SaaS & AI Series] Reinventing Accounting in the AI Agent Era With Sasha Orloff](https://cdn-images-3.listennotes.com/podcasts/inspired-insider-podcast-dr-jeremy-weisz-VW6utTIxvKU-LTBoCuxvHyQ.300x300.jpg)
Sasha Orloff is the CEO and Co-founder of Puzzle, an AI-powered accounting platform helping startups, small businesses, and accounting firms gain real-time financial insights through a smart general ledger. Before Puzzle, he was a serial entrepreneur, serving as Co-founder and CEO of LendUp and Co-…
Sasha Orloff, Puzzle, Founder & CEO on Real-Time Accounting
Sasha Orloff is Founder and CEO of Puzzle building a modern core accounting platform with real-time general ledger automation for provable accuracy. ~~~~~~~~~~~~~This episode is brought to you by Nebius — the ultimate cloud for AI innovators.Nebius provides AI infrastructure you can count on, combi…
AI is the Ultimate Accounting Assistant, with guest Sasha Orloff
Title: ATL266 — AI Is the Ultimate Accounting AssistantWiki: ATL266 - CPA Tech Wiki Guest: Sasha Orloff, CEO of Puzzle Hosts: Randy Johnston and Brian F. Tankersley, CPA.CITP, CGMA Publisher/Sponsor: CPA Practice Advisor
AI Is the Ultimate Accounting Assistant—But the Accountant Is Still Accountab…
AI is the Ultimate Accounting Assistant, Part Two (with Guest Sasha Orloff)
ATL267 – AI Is the Ultimate Accounting Assistant, Part Two
Guest: Sasha Orloff, Co-founder and CEO of PuzzleHosts: Randy Johnston and Brian F. Tankersley, CPA.CITP, CGMAProgram: Accounting Technology Lab, presented by CPA Practice AdvisorEpisode length: Approximately 10 minutes
Episode Summary
In p…
Learn What VCs Actually Want, From a Founder Who's Raised $1B with Sasha Orloff, Puzzle
Investors want founders who understand the financial reality of their business. Messy data, misunderstood metrics, or waiting until you’re nearly out of cash to start fundraising can cost founders leverage, valuation, and even a term sheet.
In this episode of Build Mode, host Isabelle Johannesen s…
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