INspired INsider Podcast · 2026-06-16 · 48 min
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.
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