Founders are told that if they work hard, build the right product and hire well, the outcome will follow. It's motivating. It's clean. And according to today's guest, it's mostly wrong.
Mike Grossman has been CEO of six venture-backed Silicon Valley companies. Across them, he tried 18 different business models. Twelve failed. Five required layoffs. Three lived in persistent existential crisis. And yet all six were eventually acquired. Mike's story is one that far more founders actually live, but almost nobody tells.
In this episode, Yaniv Bernstein sits down with Mike to dig into his new book, Failure Is An Option: a candid 44-essay collection drawn from three decades in the trenches. They explore the uncomfortable truth that luck dominates outcomes more than skill, why your business model is not your business, and how radical honesty is the most underrated leadership tool in a founder's kit.
In this episode, you will:
Learn about 'resulting': why confusing luck for skill costs founders in both directions
Hear how Mike pivoted Tempo from building a Visa/Mastercard competitor to partnering with Mastercard, only to have the entire model wiped out overnight by a Senate amendment
Discover the 'dreamers vs soldiers' framework for building teams that hold together when adversity strikes
Hear Mike's hard-won playbook for layoffs: why founders almost always cut too little, too late; what day two feels like; and why a smaller, denser team is often more productive
Get a clear framework for staying accountable for the process when the outcomes aren't in your control
Timestamps:
00:00 Coming Up...
00:34 On Today's Show: Mike Grossman on Managing Failure
02:02 The Role of Luck and Timing
03:41 Poker Strategy and 'Resulting'
08:55 "The Business Model Is Not The Business"
11:27 Tempo's Pivot
13:28 Why Values Matter In A Crisis
19:21 Talent Density and Layoffs: Cut Once, Cut Deep
28:15 How AI Changes Hiring Pace
32:15 Leading with 'Radical Honesty'
36:33 Dreamers vs. Soldiers
38:02 Managing Investors
41:43 Luck, Agency, Process
48:39 About 'Failure Is An Option'
51:29 Closing Thoughts
Resources mentioned
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Key links
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Learn more about Chris and Yaniv
Work 1:1 with Chris: http://chrissaad.com/advisory/
Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/
Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/
Producer: Justin McArthur https://www.linkedin.com/in/justin-mcarthur
Assistant Producer: Steph Hefferan https://www.linkedin.com/in/steph-heff/
Intro Voice: Jeremiah Owyang https://web-strategist.com/
