FAILURE IS AN OPTION: Silicon Valley CEO Mike Grossman Reveals the Truth About Success episode artwork

EPISODE · Aug 18, 2026 · 53 MIN

FAILURE IS AN OPTION: Silicon Valley CEO Mike Grossman Reveals the Truth About Success

from DIVERSIFIED GAME · host Kellen Kash Cache Coleman

FAILURE IS AN OPTION: Silicon Valley CEO Mike Grossman Reveals the Truth About SuccessWhat does entrepreneurship really look like when you remove the highlight reel?On this episode of Diversified Game, Kellen Coleman, M.A. sits down with Silicon Valley entrepreneur, six-time CEO, author, and former McKinsey consultant Mike Grossman, author of Failure Is an Option: Reflections of a Silicon Valley CEO.Mike breaks down the side of entrepreneurship people rarely post online: failure, bad timing, mental pressure, investor expectations, legal mistakes, family sacrifice, luck, and the difference between a good process and a good outcome.He shares how one company reached about a $30 million run rate before Congress changed the rules around its business model, while another company facing a disrupted IPO during COVID was unexpectedly acquired for roughly $400 million.The conversation also covers when entrepreneurs should quit or pivot, why “hope isn’t a strategy,” how acting as his own lawyer nearly cost Mike millions, why ownership matters, how his wife helped make his entrepreneurial career possible, and why many CEOs struggle privately with mental health.• Control effort and process, not outcomes.• Failure does not automatically mean incompetence.• Know when persistence becomes denial.• Hire experts where your expertise ends.• Ownership and long-term thinking matter.• Entrepreneurship is emotional as well as financial.• Never confuse the Silicon Valley highlight reel with reality.03:01 Mike introduces Failure Is an Option05:51 Outcomes vs. effort07:00 The $400M acquisition10:06 Hope isn’t a strategy15:20 Mike’s four tests before starting a company27:34 His biggest business mistake34:59 Ownership, debt and long-term wealth38:19 Marriage and entrepreneurship45:59 CEOs and mental health52:50 Focus on what you can controlMike GrossmanBook: Failure Is an Option: Reflections of a Silicon Valley CEOWebsite: https://FailureIsAnOption.comLearn the mindset and moves that lead to real results. Please visit my website to get more information: http://diversifiedgame.com/🔔𝐃𝐨𝐧'𝐭 𝐟𝐨𝐫𝐠𝐞𝐭 𝐭𝐨 𝐬𝐮𝐛𝐬𝐜𝐫𝐢𝐛𝐞 𝐭𝐨 𝐦𝐲 𝐜𝐡𝐚𝐧𝐧𝐞𝐥 𝐟𝐨𝐫 𝐦𝐨𝐫𝐞 𝐮𝐩𝐝𝐚𝐭𝐞𝐬.https://www.youtube.com/@DiversifiedGamePodcast/?sub_confirmation=1🔗 Support Me Here!Patreon: https://www.patreon.com/profile?u=15553364🔗 Stay Connected With Me.Facebook: https://web.facebook.com/GAMEDIVERSIFIED/Twitter (X): https://x.com/gamediversifiedLinkedIn: https://www.linkedin.com/company/gamediversifiedWebsite: http://diversifiedgame.com/📩 For business inquiries: [email protected]=============================🎬Suggested videos for you:▶️ https://www.youtube.com/watch?v=rBJSpSxBBuA▶️ https://www.youtube.com/watch?v=cmxmzwnhZ3w▶️ https://www.youtube.com/watch?v=zQrzgwornbI▶️ https://www.youtube.com/watch?v=K3PsTkobKKE▶️ https://www.youtube.com/watch?v=PnqZniYw-0k=================================🔎 Related Phrases:This Is Why You’re Not A Millionaire Yet, Hard Truths You Need To Hear, Entrepreneurship Motivation, Success Habits Daily, Real Talk About Wealth, Best Side Hustles For 2025, Millionaire Success Lessons, How To Become Wealthy, Mindset Shift For Money, Daily Millionaire Routine, What Stops You From Success, Rich Vs Poor Habits, Millionaire Morning Routine, Business Growth TruthDGP&x%

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FAILURE IS AN OPTION: Silicon Valley CEO Mike Grossman Reveals the Truth About Success

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