AMA with Sasha Orloff - His Journey to Building Puzzle
Ever wondered what it really takes to build a company from the ground up?
Join Sasha Orloff, Co-Founder & CEO of Puzzle for an exclusive AMA session where nothing is off-limits. With over $1B raised across his ventures, Sasha brings battle-tested insights on everything from fundraising and product pivots to hiring A+ teams and navigating investor conversations.
No slides. Just real talk.
Bring your boldest questions and get ready for a candid, behind-the-scenes look at the entrepreneurial rollercoaster.
And guess what? We’re heading to karaoke right after — so start picking your go-to song now! More details coming soon.
This event is a Techstars founder & alumni exclusive.
About Sasha Orloff: Sasha is a serial founder whose ventures have collectively raised over $1 billion in venture capital and debt, and Puzzle is his most ambitious yet. Having started his founder journey at YC, Sasha frequently fields questions from founders about how to prepare effectively for fundraising. To address these common challenges and streamline the preparation process, Sasha designs templates on Notion.
About Puzzle 🧩🚀
Puzzle’s accounting software is built for growing startups that need real-time financial insights without the hassles of monthly bookkeeping. Its AI-powered platform automates transaction categorization, reconciliation, and daily reporting for accurate numbers you can trust. The result is faster decisions, stronger growth, and peace of mind.