Crafting Puzzle, Challenging QuickBooks, and Helping Startups Grok Their Financial Health | Sasha Orloff (Co-founder & CEO of Puzzle)

Accounting may not be the sexiest part of running a business, but according to Sasha Orloff, it’s the key to understanding your company’s financial health—and ultimately, its success. At his previous two startups, Sasha was frustrated that he didn’t have a real-time view into his company’s financial health. And he realized the problem wasn’t accounting – but accounting software. So, Sasha founded Puzzle, because “it's hard to set yourself up for success if you don't know when you're about to run out of money.”

Sasha is on a mission to make accounting intuitive, real-time, and accessible for founders and finance teams alike.

In this episode of CRAFTED., we explore how Sasha is crafting Puzzle, how AI makes this the right moment to challenge QuickBooks, and why he was so confident that the market needed Puzzle that he was undaunted by the five years he estimated it would take to build an MVP.

"We’re not just rethinking accounting software—we’re rethinking how founders and CEOs can make data-driven decisions to build enduring companies." 

Sasha shares:

• How the frustration he felt at his previous startups led him to Puzzle 
• Why “accounting gets a bad rap”, but it crucial for founders: it’s your financial health
• Why second-time founders are ideal customers
• Why it took five years to build an MVP – and why he wasn’t daunted by this expectation
• Why the problem was never accounting, but accounting software and the distorted realities it’s built to create
• Why AI and modern API’s made now the right time to build Puzzle
• Why Puzzle is “poking the bear” and putting highway billboards up near QuickBooks HQ

• (01:04) - Sasha’s finance frustrations at previous startups
• (02:15) - Traditional accounting software isn’t made for founders
• (02:15) - The problem with traditional accounting software
• (05:01) - What Puzzle does differently: Real-time financial health
• (07:52) - AI’s role in revolutionizing accounting
• (10:22) - Why second-time founders are Puzzle’s ideal users
• (12:48) - Building a five-year MVP: Challenges and conviction
• (16:41) - Tackling QuickBooks: Bold marketing moves and billboards
• (19:15) - Understanding edge cases and complexity in accounting
• (23:07) - The future of Puzzle: Helping startups thrive
• (27:01) - Hosting the Turpentine Finance podcast

Links:

• Learn more about Puzzle: Puzzle.io
• Follow Sasha Orloff on LinkedIn: Sasha Orloff
• Turpentine Finance Podcast: Turpentine Finance

CRAFTED. is produced by Modern Product Minds, where CRAFTED. host Dan Blumberg and team can help you take a new product from zero to one... and beyond. We specialize in early stage product discovery, growth, and experimentation. Learn more at modernproductminds.com

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