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.

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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

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

Run the Numbers

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