Tim Ferriss

The Man Who Taught Me How to Invest — Mike Maples (#286)

Mike Maples in front of a black backdrop.

“Holding a grudge is a symptom of not knowing how you want to spend the gift of the day.” 

– Mike Maples, Jr.

Mike Maples, Jr. (@m2jr) is the man who taught me how to invest. He’s one of my favorite people and a personal mentor.

He is a partner at Floodgate, a venture capital firm that specializes in micro-cap investments in startups. He has been on the Forbes Midas List since 2010 and named one of Fortune magazine’s  “8 Rising VC Stars.” Before becoming a full-time investor, Mike was inolved as a founder and operating executive at back-to-back starup IPOs, including Tivoli Systems (acquired by IBM) and Motive (acquired by Alcatel-Lucent). Some of Mike’s investments include Twitter, Twitch.tv. ngmoco, Weebly, Chegg, Bazaar-voice, Spiceworks, Okta, and Demandforce.

Enjoy!

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

The Man Who Taught Me How to Invest

Want to hear a conversation with a mentor from Tribe of Mentors? Listen to this episode with Tim Urban, in which we discuss the future, how to deal with procrastination, AI, and much much more. Listen to it here (stream below or right-click to download):

Managing Procrastination, Predicting the Future, and Finding Happiness – Tim Urban

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Selected Links from the Episode

  • Connect with Mike Maples, Jr.:

Floodgate | Twitter | Medium

Show Notes

  • Introduction. [05:30]
  • How we did market research back in the day. [10:15]
  • When he first hit the scene, Mike had trouble getting hired as a venture capitalist. [13:17]
  • How did Mike connect with our mutual friend Kevin Rose? [16:19]
  • Sometimes great introductions make up for lackluster investments. [18:03]
  • Mike’s not a man who holds many grudges. Here’s why. [23:09]
  • What happened when Mike invested in podcasting platform Odeo, and how its failure led to an opportunity to invest in Twitter. [25:30]
  • Rehearsing my SXSW talk in front of three chihuahuas. [34:51]
  • Overcoming technical difficulties when it came time to give the real talk. [35:49]
  • What Mike considers one of the most fun things about being an investor in contrast to being a founder. [36:34]
  • Without children of my own, some might wonder why I often ask guests for their parenting advice. Mike’s responses are one reason. [38:39]
  • What does Mike say to bolster the morale of entrepreneurs who are going through a rough patch? [41:48]
  • Why Mike thinks he might be “the worst person to talk to depressed people.” [46:35]
  • How Mike helped me act simple. [47:59]
  • One investment that seemed like a bad idea at the time but paid off very well, and how investment decisions happen at Floodgate. [52:28]
  • How does Mike know when to persist, quit, pivot, or double down with an idea? [56:53]
  • Mike explains how investment is like surfing. [1:00:19]
  • Early encouragement and advice about first principles thinking. [1:03:00]
  • What does Mike really think about the concept of social proof? [1:04:21]
  • Good first principles in action. [1:04:28]
  • The lessons Mike hopes to drive home for entrepreneurial students at Stanford. [1:07:25]
  • How does Mike recommend people find their unique gift, and what blocks that quest? [1:11:02]
  • I’ve recently moved to Austin. Where else might I have ended up? [1:14:16]
  • What books does Mike recommend and gift the most? [1:15:31]
  • Thoughts on death, grief, and grieving. [1:17:41]
  • What emerging technologies does Mike believe are most promising for anti-authoritarian disruption? [1:19:53]
  • Why Mike isn’t afraid that cryptocurrency adoption will disrupt venture capitalism. [1:26:16]
  • Mike’s view of the government’s role and how cryptocurrency helps separate politics from economics. [1:29:10]
  • Early traits that made Mike successful. [1:30:30]
  • Why did Mike’s dad tell him not to have heroes? [1:34:54]
  • What would Mike put on his billboard? [1:36:26]
  • Mike’s take on Jim Rohn’s famous, “you’re the average of the five people you spend the most time with.” [1:38:35]
  • Powerful new truths I’ve come to realize. [1:40:25]
  • On applying loving-kindness meditation. [1:44:52]
  • What is Mike’s 60-second idea to change the world? [1:45:47]
  • Parting thoughts. [1:46:31]

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