January 27, 2025

619: Mike Maples Jr. - Practicing Reckless Optimism, Betting On Founders, Bill Gates Hiring Mike Sr at Microsoft, Being Overprepared, & What It Means To Do YOUR Best

1 hour 7 minutes

Go to www.LearningLeader.com for full show notes.

The Learning Leader Show With Ryan Hawk

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My Guest: Mike Maples Jr is a co-founding Partner at Floodgate. He has been on the Forbes Midas List eight times in the last decade and was recently profiled by Harvard Business School for his lifetime contributions to entrepreneurship. Some of his early investments include: Twitter, DemandForce, Twitch, and Applied Intuition. Mike is also the bestselling author of Pattern Breakers: Why Some Start-Ups Change the Future.

Notes

Chance favors the prepared mind. We are all visited by luck, but most of us don’t answer the door. We need to become a professional noticer. That is Mike’s favorite verb. Noticing. Most people don’t have prepared minds. Be intentional about noticing the world around you and being prepared for when luck visits you.
Mike's dad died 7 days before we recorded. “He was a mentor, a friend, and one of the greatest inspirations of my life.” His advice: Do your best. There’s only one of you. Decide what to do with your gift of time, be intentional. Have gratitude for your time. Make the most of it. Don’t waste it trying to be someone else.
Focus - Fishing competition when Mike was 5 or 6. Let’s find a good spot and stay there the entire time. While everyone else moved constantly, Mike and his dad stayed in their spot, caught a big carp, and won.
Bill Gates begged Mike’s dad to “be the adult in the room” at Microsoft. Mike Sr would say to the people he led at Microsoft, "I want to know that you’re thinking about what you’re doing." He used a Socratic method. He was not prescriptive.
Be proactive. Have an intentional strategy. Be intentional.
Jonathan Livingston Seagull - The biggest limits in the world are the limits of your mind, your imagination, and your actions– not the limits of the world itself.
Have to get over that voice in your head that says, “You’re not good enough.”
We get told to be realistic or stay within the lines.
Everybody is figuring it out as they go. Everyone is “winging it.”
Only by being radically different can you make a radical difference.
Great founders are like Patrick Mahomes and Steph Curry. You don’t know how they’re going to score, but you know they will.
Practice Reckless Optimism – The world is built by Optimists. You need to be FOR something. Bet ON something, not against it.
Mike sees himself as a co-conspirator more than an investor.
There can’t be a recipe for a breakthrough because by definition breakthroughs haven’t happened yet.
“Chance favors the prepared mind.” We are all visited by luck but most don’t answer the door.
Chris Rock - Forming unexpected connections.
Sam Beskind (Stanford basketball player where he played for Rob Ehsan) - Time management strategy. Stanford coaches had a one-pager with 3 keys to winning. Not 20. 3. If you have 20 keys, you have none. Nobody can remember all that.
Life/Career Advice: Internalize what it means to do your best. Gratitude for your time. Avoid the trap of mimetic desire. The “T” of knowledge. Charlie Munger. Try to know what the best ideas that have ever existed in a wide range of fields. Then choose one field to know about more than anyone else in the world. Have one area where you are fanatically obsessed. For Mike, that’s startups.

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