Banker to Investor to Operator: Nick Chammas, CFO of Eight Sleep, on Why Your Job is Always to Sell

Nick Chammas, CFO of Eight Sleep, joins CJ to discuss his career journey from working as a first-year analyst on Google's IPO to his current role as CFO of Eight Sleep. He shares anecdotes from the Google IPO process (including a memorable story about Eric Schmidt) and a wealth of knowledge that he gained throughout the years. He talks about what it was like being a banker versus an operator and offers a word of caution for startup operators working with investment bankers for the first time. He emphasizes the necessity for sales skills irrespective of your role and gives tips on how to convey a balanced story to your board. He also provides insight into decision-making, explaining the difference between one-way and two-way doors, how to approach each, and how to navigate numbers versus gut feelings.If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.—SPONSORS:Planful is a financial performance management platform designed to streamline financial tasks for businesses. It helps with budgeting, closing the books, and financial reporting, all on a cloud-based platform. By improving the efficiency and accuracy of these processes, Planful allows businesses to make better financial decisions. Find out more at www.planful.com/metrics.Leapfin is accounting automation software that automatically prepares and posts reliable journal entries. High-growth businesses like Reddit, Canva, and Seat Geek choose Leapfin to eliminate manual tasks, accelerate month-end close, and enable accounting leaders to provide faster insights to help their companies grow. To automatically standardize your revenue data with measurable business impact, check out leapfin.com today. Mercury is the fintech ambitious companies use for banking and all their financial workflows. With a powerful bank account at the center of their operations, companies can make better financial decisions and ensure that every dollar spent aligns with company priorities. That's why over 100K startups choose Mercury to confidently run all their financial operations with the precision, control, and focus they need to operate at their best. Learn more at mercury.com.Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust®; Members FDIC.NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist. Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.—FOLLOW US ON X:@cjgustafson222 (CJ)—TIMESTAMPS:(00:00) Preview and Intro(02:57) Sponsor - Planful | Leapfin (05:25) Introduction to Eight Sleep(07:05) Working on the Google IPO (11:50) A Story From the Google IPO Roadshow(13:40) Banking Versus Investing Versus Operating (15:21) Date the Banker, Marry the Analyst (17:06) Sponsor - Mercury | Netsuite | Maxio(20:29) Advice for Startup Operators Working With Investment Bankers(22:34) Deal Fatigue Versus Deal Momentum(23:53) Knowing How to Sell(27:29) Decision Making: One-way Versus Two-way Doors(30:32) Numbers Versus Gut Feel or Anecdotes(36:17) Tips on Conveying a Story to Your Board(39:22) Long-ass Lightning Round: Choosing a Job Versus Choosing a Boss(40:49) Finance Software Stack(41:37) Craziest Expense Story This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com