Suggestions
Sasha Orloff
CEO of Puzzle and host of the Turpentine Finance podcast. YC, ODF, Village Global alumni.
Sasha Orloff is the Co-founder and CEO of Puzzle, a company that has raised over $1B of venture capital and debt. Puzzle has developed a modern core accounting platform focused on accuracy and automation.
Sasha is also the host of the Turpentine Finance podcast, where he shares insights on finance, accounting, and successful company strategies. The podcast is available on Spotify, Apple, and YouTube.
With over 20 years of experience, Sasha Orloff has been involved in predictive analytics and data to enhance business and community outcomes. He has worked in startups, multinational corporations, governments, and non-profits in various capacities like manager, entrepreneur, advisor, and board member.
Sasha Orloff is passionate about helping startups create more valuable businesses by leveraging a next-generation general ledger for accounting, making it a competitive advantage for startups.
In addition to his professional work, Sasha has been a guest lecturer at prestigious universities like Stanford, Princeton, Georgetown, and Harvard. He has also presented at events like TEDx, World Economic Forum, and various fintech conferences.
Sasha Orloff has been featured in renowned publications such as The Wall Street Journal, The New York Times, TechCrunch, and many others. His educational background includes studies at Y Combinator, Harvard Business School, Stanford, Georgetown University, and other prestigious institutions.
Throughout his career, Sasha has been affiliated with organizations like Turpentine, For Every Founder, On Deck, Revolut, The Aspen Institute, and TransUnion, holding roles varying from podcast host to CEO to advisor and board member.
Highlights
Startups are losing money with inefficient manual AR processes.
Fellow YC founders @danielkivatinos and Anelya Grant from @getjustpaid shared their framework for streamlining accounts receivable (AR) operations with me on @TurpentineMedia!
We discussed:
💡 How their CHARGE framework breaks down AR into cost, handling, amount, responsibility, growth, and extent ⚙️ How to use AI to remove manual errors and accelerate collections 📈 How to scale AR operations to handle 10x the volume without adding headcount.
Listen to the full episode to fix your AR process (link in the comments!)
Here's how to close deals faster - organize your data room before investors ask for it.
The difference between quick closes and failed deals comes down to preparation:
• Build your data room methodically from the start. • Share only what’s requested, but always be prepared. Financials, contracts, and key metrics should be a click away. • Update those numbers monthly. This 30-minute habit saves weeks of scrambling during fundraising.
The best deals move fast. I use @NotionHQ to manage and organize @puzzlefin's data room - get the template I use + 6 months of Notion for free in the comments!
