Navigating Fundraising and Financial Diligence with Sasha Orloff

On The Deep End today, we welcome Sasha Orloff, the Founder and CEO of Puzzle, a modern accounting software package for startups that recently raised $15 million in series A. Sasha joins us to discuss the use of accounting as a powerful decision-making tool and the creation of infrastructure to start and scale businesses, as part of our series on meta-problems to help founders start more companies. Despite advances in financial technology, Sasha believes that core accounting software remains outdated and does not take advantage of modern capabilities. He suggests that accounting could be a competitive advantage for businesses if it were reimagined as a tool for data-driven decision-making, empowering founders to build better businesses. During the episode, Sasha identifies three key areas that founders should focus on when fundraising: telling a compelling story, taking the process seriously, and planning for success: Founders must have a strong answer for what sets them apart from their competitors, and they should be intentional about raising venture capital. As the market returns to normal, Sasha advises founders to be aware of business compliance and financial diligence to avoid giving away a larger percentage of their company for less money. Throughout the episode, he emphasizes the importance of founders understanding their business numbers to make informed decisions and build successful companies. You can learn more about Puzzle at https://puzzle.io.