“How I Screwed Up Accounting” - Sasha Orloff, Puzzle

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Accounting might not be the flashiest part of startup life—but it is one of the most critical.

Sasha Orloff is a repeat founder currently leading the team at the accounting platform Puzzle. Previously, he was the founder of LendUp and Mission Lane.

In this episode, Sasha reveals how he almost lost a crucial investment over accounting mistakes at his first startup. What began as a scramble to follow "best practices" by hiring firms and building a finance team turned into a painful lesson: traditional accounting wasn't designed to help founders build businesses.

"My first surprise was you have to file taxes even if you don't generate any revenue, which for a lot of early stage startups, we don't generate revenue right away."

For Sasha, this seemingly small mistake led to big consequences

“It nearly cost me a term sheet,” Sasha says. “I had an investor say to me once, ‘If you’re building a company and you’re not doing the things that are required by law… what else are you not doing?’” 

That wake-up call reshaped not just Sasha’s view of accounting—but his entire perception of the industry as a whole. 

In this episode, Sasha unpacks: 

• How his first “fix” to his accounting problem only made things worse

• The “aha” moment where he realized where he went wrong

• How that moment became the spark that led him to build Puzzle

Whether you’re a first-time founder or ten years in to building company #2, this episode will leave you with a clearer sense of why financial clarity matters, what not to do, and how screwing something up can sometimes be the start of your best idea.