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[SaaS & AI Series] Reinventing Accounting in the AI Agent Era With Sasha Orloff

INspired INsider Podcast

Release Date: 06/16/2026

[Top Author Series] From Incremental Growth to 10X Scale With Blake Erickson show art [Top Author Series] From Incremental Growth to 10X Scale With Blake Erickson

INspired INsider Podcast

Blake Erickson is the Co-founder of Scaling.com, a research and advisory firm that helps established businesses pursue tenfold growth through strategic guidance and its Scaling Framework. He leads the company's strategist team and guides its strategic direction, having personally trained more than 1,200 people. Blake also co-authored The Science of Scaling, a New York Times bestselling book written with organizational psychologist Dr. Benjamin Hardy. An experienced entrepreneur and keynote speaker, he helps business owners strengthen leadership, identify growth opportunities, and develop...

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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-founder & Advisor to Mission Lane, with previous ventures collectively raising over $1 billion. Sasha also hosts the “Tech Finance” with Sasha Orloff podcast, where he interviews leaders shaping the future of finance and accounting.

In this episode…

For many businesses, accounting remains a slow, backward-looking process that delivers insights long after decisions have already been made. As AI reshapes industries across the economy, could financial operations become real-time, accurate, and proactive rather than reactive? What would it take to modernize one of the most critical yet overlooked functions in business?

Sasha Orloff, a serial entrepreneur and technology innovator, says the key is to rebuild accounting systems from the ground up, with data integrity and AI at the core. He notes that traditional software lacks real-time intelligence, leading to inefficiencies and delays. By reengineering the general ledger, businesses can access faster, more reliable financial insights and automate complex workflows. AI-powered anomaly detection and reconciliation further improve accuracy while reducing manual effort. The outcome is a more scalable and intelligent financial system for companies of all sizes.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz talks with Sasha Orloff, CEO and Co-founder of Puzzle, about transforming accounting with AI. They cover rebuilding systems for the AI era, using AI for accuracy over speed, why strong accounting drives growth, and strategies for adoption, customer trust, and go-to-market in a conservative industry.