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
Jan 27, 2025
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Mike Maples Jr. is a co-founding partner at Floodgate and known for early investments in Twitter and other startups. He emphasizes the power of being intentional and prepared, sharing that luck favors those with a 'prepared mind.' Reflecting on his father's mentorship, he highlights the importance of authenticity and gratitude in life. Maples advocates for embracing 'reckless optimism' in entrepreneurship and discusses the need for founders to inspire confidence. He also reflects on missed opportunities, such as not investing in Airbnb, emphasizing the value of trust in decision-making.
Emphasizing the importance of authenticity, true success is achieved by aligning personal strengths and passions with market needs.
The wisdom of mentors shapes our journey, highlighting the significance of doing your best and valuing the gift of time.
Overcoming self-doubt is essential for growth, as consciously pursuing aspirations can counteract negativity and inspire action.
Deep dives
The Importance of Being Unique
Each individual has the potential to excel at something uniquely suited to their abilities and passions. Contrary to the common belief of competing to be 'the best,' true success lies in identifying a niche that aligns with personal strengths and market needs. When one operates at the intersection of what they love, what they're good at, and what they can earn from, they become irreplaceable rather than merely the best. This perspective reframes success as a journey to authenticity rather than a race to the top.
Lessons from a Father
The wisdom imparted by a mentor or parent can profoundly shape one's view on life and work. A poignant lesson shared was the notion of 'doing your best,' which transcends mere achievement and reflects gratitude for the gift of time. The speaker's father illustrated through personal anecdotes that focus and dedication, exemplified during a fishing competition, can yield extraordinary results even amid distractions. This emphasis on personal authenticity and purpose empowers individuals to honor their unique contributions to the world.
Navigating Self-Doubt
Managing the internal voice of self-doubt is crucial for personal growth and achievement. Many individuals grapple with the thoughts that undermine their confidence, often leading to inaction and missed opportunities. The approach to overcoming this voice involves recognizing it as unwarranted negativity and consciously choosing to pursue goals regardless of those doubts. By actively deciding to engage with aspirations, individuals can sidestep the paralyzing effect of self-criticism and push forward towards their ambitions.
The Role of Noticing in Leadership
Cultivating the ability to notice the world around us can greatly enhance leadership effectiveness. By being attuned to subtleties and unexpected connections, leaders can identify opportunities and insights that might otherwise go unnoticed. The analogy of stand-up comedians highlights how their observational skills allow them to capture and convey unique perspectives humorously. This skill of 'noticing' enables leaders to lead with creativity and insight, fostering environments where innovation can thrive.
Embracing the Journey of Discovery
The path to success is often filled with trial and error, highlighting the importance of resilience and exploration. Many renowned entrepreneurs, like James Dyson, exemplify how embracing failure with curiosity can lead to remarkable breakthroughs. This perspective emphasizes that the willingness to experiment without fear of failure is crucial for long-term growth and discovery. Ultimately, success comes from consistently engaging with challenges, learning from them, and not being afraid to pivot when necessary.
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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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