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

“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, ngmoco, Weebly, Chegg, Bazaar-voice, Spiceworks, Okta, and Demandforce.


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]

People Mentioned

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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32 Replies to “The Man Who Taught Me How to Invest — Mike Maples (#286)”

  1. Please provide transcripts along with your podcasts! I generally do not have the time to listen to a podcast, but would like to read the content. I’m sure there are many other people who are in the same situation!

    1. Transcripts could be generated quickly by teaching dragon voice engine, and running recording through software- it will transcribe it, like it does for MD’s and attorneys.

    2. I sat for a moment to read this comment. When I hit the back button I was offered a free ebook for 5 morning rituals…required an email address entry as well before receiving the file to read. – All I can think is this was some sort of A/B testing to see if people read longer form items, such as a transcript.

    3. I find that podcast are a much great time saver, because you can listen as you do another task that requires your eyes and hands, you can listen to a podcast at 2X speed if you want to get through it really quickly.

  2. Great guest, particularly enjoyed Mike’s thoughts on Capitalism. If you have a part two, I’d like to hear Mike explain his comment that Fed intervention hurts the middle class. How exactly does that work? I don’t doubt it, but the connection isn’t clear to me.

    Thank you for continuing to educate me.

    1. Mike…It would have been fun to have gone down that rabbit hole some more:) Here is how I think about the issue at a high level. This is a little bit of a stream of consciousness so I hope I don’t ramble too much this late at night:

      In a truly free economy, the price of money (aka interest rates) would be set by supply and demand by the private banking system rather than set artificially by the Fed. Banks would locally determine the cost of money based on the local supply of money they can safely offer in a way that lines up with demand for money that contributes to business expansion.

      Why is this?

      Most companies of all types finance some of their businesses with bank loans. In a free market, banks “invest” the savings of their customers’ deposits into other companies (in the form of loans) that they think will be most successful. In order to be successful in a free market, banks must be very careful who they loan money to or they can run out of money and go broke from bad loans.

      When the Fed sets interest rates artificially below a level that would be set by free-market supply and demand of money, banks are confronted with a much greater number of requests for loans. In a “normal” market, banks would throttle demand for easy money by raising interest rates. This has the effect of reducing the number of unworthy borrowers. At the same time, because higher interest rates reduce the prices of stocks (because a stock is the present value of future cash flows discounted at a now higher interest rate), you also have less speculation in the stock market.

      The original Great Depression was only made possible because the government in 1913, for the first time, began to intervene in a fundamental way to manipulate the money supply. A cheap money policy was the goal of government officials. Interest rates no longer rose in response to increased speculation and borrowing.

      The Fed believed that by taking the control of the pricing of money out of the hands of private banks, it could guarantee a permanent prosperity by smoothing out the ups and downs of the business cycle. Many officials thought that, by manipulating the money supply, they could keep the economy in a permanent boom.

      But the Fed was wrong to do this. A free banking system in the 20s would have been forced to curtail the rampant borrowing and speculation that occurred. Instead, these behaviors went unchecked and widened in their scope until eventually everything came crashing down in a chain reaction.

      A similar thing happened in the ‘00s for a different reason. In response to the recession of 2001 and the terrorist attacks and other weaknesses in the US economy, the Fed kept interest rates artificially low to keep the economy moving.

      What happened was predictable: When you make the price of money artificially low, you encourage more people to borrow. Soon people were borrowing money like crazy to buy houses they couldn’t afford. And Wall Street made things worse with CDOs and other instruments that pooled the risky loans into a toxic mess that almost destroyed the economy.

      Why does this hurt the middle class? The American Dream is about being rewarded for honest work that drives *productivity* and *output* forward and this is what most of the middle class jobs are about…expanding the economy through increased productivity that is a win//win for the worker and for society. But in an economy where wealth is created more easily by borrowing money, pretty soon you have an economy based on people pimping their houses to each other. The people who take out loans they can’t afford or financial engineers who can tap into the massively overflowing money supply and skim off the top get to jump in front of the line of the honest people who are doing the real work to get ahead.

      And when things spin out of control, two things always happen:

      1. People blame the “free market” or “capitalism” when in fact it is the LACK of free market policies that causes the wide-sweeping set of distortions that blow up and cascade out of control;

      2. The middle class foots the bill when the banks and financial institutions are “too big to fail.” You can’t have a chain reaction where even the good banks fail along with the bad, since everything is so linked…It would cause the money supply to fall to zero and a mass panic…So the government is forced to put a wall of money in front of the problem (at Main Street’s expense or at future generations’ expense because it prints money to get out of the problem.)

      In my opinion, people should get prosper in a free society by creating *value* rather than profiting from distorted economic incentives driven by the Fed jacking with the money supply. A lot of people in the middle class are starting to think that they are “suckers” in a rigged system in which they wait in line by the rules while others cut in line because they profit from unsound money.

      Hope that helps. It’s now officially past my bedtime 🙂

  3. Hi Tim,

    Really curious as to how come we weren’t introduced to your old friend even sooner in this podcast.

    Hope it’s not a problem I’m mentioning other podcasts, but if I’m not mistaken I’ve heard your story with Mike on either the Rolf Potts or Cal Fussman podcast. Probably the latter if I remember the flow of the conversation correctly.

    It’s nice to see someone that had such a positive impact be brought on the podcast. There are a few other people I’ve heard of along many of your conversations and it would definitely be interesting to see some of them have their own episode in here as well.

    Looking forward,


  4. Where can I find your 2018 event schedule? I want to ask for tickets to one of your events for my birthday gift this year.

  5. So much great knowledge in this one, but what impacted me most is how ready at hand Mike is with his gratitude and emotion.

  6. Hey Tim, good to meet at your recent Tribe of Mentors book event at Castro Theatre. Great interview with Mike Maples.

    Question: Which organizations or charities can you recommend that support young entrepreneurs get a headstart? I’m working on a project to help fund nonprofits that focus on developing entrepreneurs in the early stages. One I’m looking at is Girls Who Code, but looking for others targeting early career entrepreneurs (18-25 year olds).

    Any suggestions?



  7. Your TED talk on the stoics and fear setting really gave me a much need directional perspective. I’ve changed things up and am fear setting for 2018 thanks

  8. Tim,

    Just wanted to know you were the answer to one of the questions on our esteemed University Challenge TV programme here in the UK last night.

    The question Jeremy Paxman asked was “A self-confessed professional dilettante, which US proponent of self-help is the author of the 4hr Chef and the 4hr work week….?”

    Answered correctly by an American studying at Trinity College Oxford.

    You probably won’t be able to view it in the US unless you have a VPN but someone you know might. It is episode 21 of the current series. You can search bbc iplayer to find it. About 6 mins in.

    Anyway, in British Intelligentsia you know you have arrived if you make it as an erudite question on the show – 65 years and still going strong.

    David Gingell

  9. What a great podcast! I’m not one to listen to leave comments, but this was a great conversation that hit on so many interesting life topics. I am a venture investor in India and its amazing how much of this discussion I could both relate to as well as gain insights from. Thanks for sharing this.



  10. Hello from Malaysia. I’ve heard of Tim Ferris via the 4 hour workbook but was introduced to the podcast via Spotify.

    The program has been insightful and at times, mind blowing.

    The Spotify gig really expanded your reach Tim!

  11. Hi Tim!

    I’ve been thinking a lot about the question “what would it look like if it we’re easy?”. I’m having a lot of trouble apply that to my situation. Would you be able to expand more on that question in a podcast or article?

    Thanks so much! Have a great holiday!


  12. I really enjoyed this!

    My favourite quotes from Mike:

    “Entrepreneurship comes from love and creation, not anger and disruption”

    “What would JP Morgan do?”

  13. Meaty. The great lesson in this episode is “understand your (YOUR) first principles”. I really valued the philosophical lens, from different angles, on the role of entrepreneur.

    Idea: an interesting head to head would be Mike and M. Sanjayan chewing on entrepreneurship as relates to solving conservation and environmental condition challenges.

  14. Mike had some amazing founder stories. I had to rewind a couple times so I could hear them again.

    Good luck in Austin Texas Tim!

  15. WOW, my new favorite!! I would love to share the epiphany I discovered about “love yourself”. I was set down that path at age 13 when I was handed a book of that exact title. (after my first battle with suicidal thoughts came online)

    I spent years of self torturing “trying” to “love myself”. I was well into my 40’s when I discovered the secret for my brain. LOVE IS NOT A VERB.

    Love is the experience of a feeling. It is sensations in the body. Sensations that CAUSE acts of love. Yes, you can go the other way, but then you are locked in conditions. “I did this, therefore I get to feel love.” It’s temporal and fleeting.

    In my journal that night I wrote “I am feeling loved.”

    And because I love playing with words, I dove into variations and experimented with them over several weeks.

    This was the most powerful for me:

    “I now command my subconscious mind into I am feeling loved in and out of time.”

    here’s the breakdown:

    “I now command my subconscious mind” – deep well of gratitude to Tony Robbins for the prefix!

    “into” – grammatically goofy but neurolinguistically perfect – I am commanding “enter into this state”

    “I am feeling loved” – literally this is ALL you have to do – FEEL loved

    “in and out of time” – While I’m Day Setting and Night Setting the “out of time” meditative type place is in force. This was the power verbage that steered the subconscious mind to carry it through the rest of the day.

    The protocol is so simple you’re only going to believe it after you’ve followed it fully to prove it’s bunk.

    1. In the morning, get into intention-state and write and or say “I now command my subconscious mind into I am feeling loved in and out of time.”

    2. In the evening, check in with how self-love fared that day.

    3. repeat for 2 weeks

    4. check in with how your life has been over the past 2 weeks


    I wrote a little chant/song of the power phrase and it still is one of the mp3 pre-alarms I wake up to every morning.

    (*pre-alarms – I run 3-4 Day Setting alarms before the “no really get out of bed” alarm goes off. It’s sooooo delightful to wake up to my voice saying & singing nice things to me!)

  16. Hi Tim,

    Thank you.

    I was standing on a rooftop of a building I was prepared to jump off of and then your “Powerful new truths I’ve come to realize [1:40:25], On applying loving-kindness meditation. [1:44:52], and What is Mike’s 60-second idea to change the world? [1:45:47]” sections part of the podcast came on. It stopped me from going through with my plan.

    I am holding on by exploring the books (Tribes of Mentors included) and metta meditation you mentioned. I am wondering if you could go further down this rabbit hole and speak to this topic a bit more……perhaps in a form of a short podcast?

    Thank you once again.

    1. Hi RST! First off, this was going around FB yesterday:

      Could one friend please copy and re-post? We are trying to demonstrate that someone is always listening.




      Just one person makes a difference

      So First Off:

      You WERE heard. I saw your post as I was headed to bed & sent supportive energy your way.


      Tim has this great interview with Adam Robinson who has some practical insights on suicidal depression and the conversation weaves that direction.

      Adam has come out the other side & his twitter is full of enthusiastic life.


      Search Tim’s blog for “suicide”, you’ll find a couple deeper dives.


      Build your support team. Find a great counselor.

      Your “break glass in case of emergency” lever is getting triggered when you’re not days atop Mt Everest, broken leg, intense pain, wolves looming. We can’t fix the faulty sensor, but we CAN:

      ! create many alternative neuropathways!

      ! install pre-pre-pre warning systems!

      ! amass so many tools to deploy at the pre pre pre stages that we successfully avert that neuropathway!

      ! develop Self-Loving, Self-Caring, Self-Empowerment so strongly that even if the lever gets pulled, we have Best Self pulling from many directions back out of it!

      I wish you all the success on your journey upward into your New Life. You have faced death and said “no thank you! I gots shit to do!!”.

      I am SO proud of you!!

      And here are some words for you to play with:

      What would it feel like if I saw my worth as priceless?

      What would I do if I felt Enough to overflowing?

      1. Michelle – Thanks for your supportive energy and all the information you’ve shared. They are very helpful and I will be focusing my energy on absorbing all the materials to give myself a chance.

  17. Listened to this a couple of days ago and needed to say that, of all the ≈ 200 episodes I’ve listened to, this is the episode which has touched me most deeply. Mike, you are so warm, heartfelt, and relentlessly positive. The highlights were many, but number one is your words about parenting. If I can remember that they didn’t choose to have me when I’m talking to my kids, I will be a much better father. The one other thing I want to thank you both for is the talk about being kinder to ourselves. Thanks to both of you for sharing this conversation with the world.

  18. Really enjoyed learning more about Mike Maples (and Tim!)

    John Boyd does not get enough credit for his ideas. A former customer wrote a book about Boyd (Boyd: The Fighter Pilot Who Changed the Art of War) which opened my eyes to the OODA Loop concept. This concept is well outlined in the book which can also be applied to lots of business situations/models. There is also a very intriquing breakdown of brainstorming as outlined by the Destruction & Creation model using the example of a snowmobile. I believe this is one way to create ‘Zero to One’ ideas as Peter Thiel wrote about.

    Thanks for all your insights and ideas to learn from.

  19. Tim,

    Love your podcasts and books! They’ve inspired me in a number of ways. I was listening to you talk with Mike Maples, Jr. and really enjoying it. Mike is fascinating and I love his values. Then the OODA Loop was mentioned, and I thought “ooooh crap, the article I’ve been procrastinating on for years is going to be irrelevant as soon as Mike is done explaining it”.

    Lucky for me, Mike’s explanation of the OODA Loop is far different from how I understand and use it. But I didn’t want to say anything until my answer was complete. So, I built a blog and wrote an article that I think you and Mike might like and found useful. Not sure if its kosher to post a link here or if anyone is interested. It’s titled- Boyd Revisited: Lessons from an Apex Predator. Let me know if it is or you are.



  20. Hi RST! I was clearing out an old website and came upon our exchange from 2018. I wanted to follow up with you and see how things are progressing along your journey.

    How are your tools and resources serving you these days?