The Random Show — New Year’s Resolutions, 2010-2019 Lessons Learned, Finding Joy, Energy Management, and Much More (#408)

Technologist, serial entrepreneur, world-class investor, self-experimenter, and all-around wild and crazy guy Kevin Rose (@KevinRose),  rejoins me for another episode of “The Random Show.” In this one we explore the language of relationships, polarity, energy management, difficult conversations, finding peace and patience, the importance of self-compassion, the search for palatable decaf coffee, panic-selling, serving the moment, and much more!

Please enjoy! 

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform. You can also watch the conversation on YouTube

#408: The Random Show — New Year's Resolutions, 2010-2019 Lessons Learned, Finding Joy, Energy Management, and Much More


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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear another episode of The Random Show? — Check out my conversation with Kevin when I was in his neck of the woods a few months back in which we discussed Japanese whiskey, domestic speakeasies, wooden saddles, poetry, the art of surrender and letting go, and mushroom cultivation in the Pacific Northwest. (Stream below or right-click here to download):

#391: The Random Show — On Fasting, Forest Bathing, How to Say NO, Rebooting the Self, and Much More



  • Connect with Kevin Rose:

The Kevin Rose Show | Oak Meditation | Zero | Instagram | Twitter


  • Why is Kevin introducing this show like he’s the 2020 incarnation of Rain Man? [04:03]
  • Why was wine appropriate for the 10-year anniversary of Kevin and Darya’s first date? [04:57]
  • Opining on lessons learned from past relationships, polarity, sensitivity, and cultivating the structures that make our current relationships work — even when there’s an occasional breakdown in communication. [07:09]
  • What did therapy look like when Kevin and Darya were seeing a therapist, and what are the most valuable tools they took away from the experience? [20:12]
  • What a writer can learn when they get language wrong in a relationship and their partner is patient enough to guide the conversation toward a more understanding tone. [21:48]
  • What comes to mind most when Kevin reflects on the past decade and what the years ahead have in store? In what area does he feel he’s improved upon thanks to lessons and interactions from the past? [25:33]
  • Why I tend to err on the side of admitting I don’t know something or someone rather than trying to fake it, where I think my biggest knowledge gaps are currently, and how I’m trying to minimize the number of decisions I’m obligated to make. [28:28]
  • Why I’m now so committed to strategically saying “no” when I used to say “yes” to everything. [31:22]
  • As someone who’s known me since well before I had 618,952 unread emails, 287 unread text messages, a neverending supply of unsolicited spam books from publishers, and occasional recognition from strangers on the street, Kevin wonders if I maybe feel a little overwhelmed these days. How am I dealing with time, attention, and energy management? [35:00]
  • What are the categories of things that have depleted our energy versus the categories of things that have given us energy? What would we like to more of/less of in 2020? [39:53]
  • Pondering questions Jerry Colonna asked me in episode 373 and applying them to the new year (and heavy conversations I’ve had over the past two weeks): How am I complicit in creating the conditions I say I don’t want? What needs to be said that isn’t being said? What’s being said that I’m not hearing? What am I saying that’s not being heard? [45:32]
  • Thoughtful notes to the living and dead, why I resolved to have some recent difficult conversations by voice instead of mail, why I don’t write Kevin as many love letters as I used to, and why a resolution can serve the purpose of closing a loop even if it doesn’t offer any solutions. [51:29]
  • Important realizations I’ve had when thinking back over the last 10 years. [58:11]
  • What does the next decade look like for me from a bio-hacking standpoint? Is it still something I focus on, or have I moved away from it intentionally? [1:01:30]
  • How my interest in bio-hacking began as a self-defense mechanism, and why my focus has shifted more from the known to the unknown in terms of how treatments for certain maladies and disorders are being explored now. [1:07:15]
  • A realization I’ve had recently about finding peace, and why I’m not making a million resolutions for 2020. [1:16:39]
  • To what does Kevin credit his greater sense of ease and patience over the last few years? How does this contrast with the way he dealt with situations in the past — even situations he should have been enjoying but couldn’t? [1:17:42]
  • A book I’m really enjoying now that would have earned mockery from the me of 10 years ago — and how it’s helping me reframe some of the mental struggles that both of us have endured. [1:20:15]
  • A lot of people who take pride in being achievers don’t extend compassion toward themselves — and I think Kevin and I have both fallen prey to this self-neglect in the past. If you’re having internal dialogue that’s critical without being compassionate, how might we suggest breaking away from its influence for a fresh perspective? [1:27:04]
  • Is there such a thing as good decaf coffee? If you know of any, please tweet Kevin! For my part, I’m happy to be the first non-caffeinated monkey shot into space on the quest to enlightenment through abstinence. [1:31:32]
  • Addressing one of the biggest self-help elephants in the room. [1:33:54]
  • If psychedelics become a legal form of therapy, can the world look forward to Tim Ferriss-branded psychedelic treatment mall kiosks? [1:37:37]
  • One fun money-generating idea for psychedelic research charity I’m thinking of pursuing in 2020, how Kevin’s connections may already be able to help, and why I think money spent in the direction of this research is capable of such monumental, world-changing results. [1:44:52]
  • Dream artists I would love to have participating in this effort. [1:48:23]
  • What uninvestigated secrets might be revealed by paying top-tier journalists $2 a word to find them? [1:49:57]
  • What does Kevin feel he did quite well over the past 10 years, and what insight might he offer others seeking similar success? [1:55:13]
  • What is Kevin’s framework for deciding when it’s time to sell off investments — or buy more? [1:59:19]
  • A time I most regret panic-selling an investment, why it happened then, and what I’ve learned since that decreases the likelihood of panic-selling as my go-to strategy now. [2:01:14]
  • Understanding one’s own strengths and weaknesses, the luxury of being able to make occasional mistakes in the investment game when you hit home runs more often than you strike out, and how Kevin plays this game safer than it probably looks to an outside observer. [2:04:50]
  • What is Kevin’s “20 percent ultra-risky” strategy, how did he invest when he didn’t have much to risk, and what happens when that 20 percent grows to 40 or even 90 percent? [2:08:40]
  • On living well as the best revenge, becoming better at following my own advice over the past 10 years, and why letting an Internet troll starve is ultimately better for you and the troll. [2:13:08]
  • How Kevin applies Michael Singer’s quote to “serve the moment” to his own circumstances. [2:19:12]
  • Final thoughts. [2:20:32]