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
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.
01:07:57
forum Ask episode
web_stories AI Snips
view_agenda Chapters
menu_book Books
auto_awesome Transcript
info_circle Episode notes
volunteer_activism ADVICE
Do Your Best
Do your best and be the best version of yourself.
Express gratitude for your time and don’t compare yourself to others.
question_answer ANECDOTE
Focus and Discipline
Mike Maples Jr. and his father won a fishing competition by focusing on one spot.
Others moved around frequently, but they stayed put, demonstrating the power of focus.
question_answer ANECDOTE
Thoughtful Process at Microsoft
Bill Gates invited Mike Maples Sr. to join Microsoft and manage products.
Maples Sr. encouraged thoughtful processes instead of simply coding intensely.
Get the Snipd Podcast app to discover more snips from this episode
This classic novel by Robert M. Pirsig is a personal and philosophical odyssey that delves into the author's search for meaning. The narrative follows a father and his son on a summer motorcycle trip from the Midwest to California, intertwining a travelogue with deep philosophical discussions. The book explores the concept of 'quality' and how it informs a well-lived life, reconciling science, religion, and humanism. It also touches on the author's own struggles with his past and his philosophical quest, making it a touching and transcendent exploration of human experience and endeavor.
Jonathan Livingston Seagull
Richard Bach
Russell Munson
The book tells the story of Jonathan Livingston Seagull, a seagull who is different from the others in his flock. While most seagulls focus on eating and survival, Jonathan is passionate about flying and constantly challenges himself to improve his flight skills. His nonconformity leads to his banishment from the flock, but he continues to pursue his dreams, eventually finding other like-minded seagulls and learning valuable lessons about love, kindness, and transcendence. The story is an allegory about seeking a higher purpose in life and not compromising one's vision, even in the face of societal pressure[2][4][5].
The Beginning of Infinity
Explanations That Transform the World
David Deutsch
In this groundbreaking book, David Deutsch argues that explanations have a fundamental place in the universe and that improving them is the basic regulating principle of all successful human endeavor. The book takes readers on a journey through various fields of science, history of civilization, art, moral values, and the theory of political institutions. Deutsch explains how we form new explanations and drop bad ones, and discusses the conditions under which progress, which he argues is potentially boundless, can and cannot happen. He emphasizes the importance of good explanations, which he defines as those that are 'hard to vary' and have 'reach', and argues that these explanations are central to the Enlightenment way of thinking and to all scientific and philosophical progress.
Be Here Now
Ram Dass
Be Here Now is a seminal book on spirituality, yoga, and meditation written by Ram Dass. The book is divided into four sections: 'Journey', which details Ram Dass's transformation from a Harvard psychologist to a spiritual seeker; 'From Bindu to Ojas', a core section that includes spiritual themes and inspirational quotes; 'Cookbook for a Sacred Life', a manual for conscious living with practical advice on meditation, yoga, and diet; and 'Painted Cakes (Do Not Satisfy Hunger)', a list of recommended books for further spiritual exploration. The book emphasizes the importance of living in the present moment, shedding ego and material attachments, and finding unity with the divine through unconditional love and mindfulness[2][4][5].
This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver.
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.
The Learning Leader Show With Ryan Hawk 
