Day 86: How to Become a Questions Machine (Part 5)

As I continue to listen, read, and watch James Altucher everyday to prep for a once in a life-time podcast interview — this is how I would introduce James or so I think if my nerves don’t get the best of me…

Welcome James Altucher to an Interview with Melissa Llarena. James is the author of several Wall Street Journal Best Selling books including ‘Choose Yourself’ where he suggests that we write 10 ideas everyday to become an ideas machine. James has co-founded 20 companies 17 of which have failed on paper yet have given him winning lessons. He is the host of widely popular podcasts The James Altucher Show and Ask Altucher. He is a chess master and helped behind the scenes on “Deep Blue” the AI which beat the World Chess Champion, Garry Kasparov in a historic match. James is a venture capitalist. And these days, you can find James doing stand up comedy in local NYC clubs. Welcome James and happy early birthday.

You intrigue me. Your writing is relatable and provocative. You’ve risen back up from the ashes several times personally and professionally. And the way you are grabbing life by its horns is inspiring. You do things sober that require most people a bit of liquid courage to even think about.

Here are some questions that I’d love to ask you:

  1. What are you learning about yourself as you continue to do stand-up comedy? How is this affecting your self-esteem? How is it shaping the way you look at everyday situations? Any wacky places from which you’ve gotten your content?
  2. It’s hard for me to focus on any one thing at a time. When I worked in advertising, I thought I’d be happy only doing one thing but I realized I’m not. How have you made your interests in such wide-ranging things work together in a way that you’ve been able to make some real impact.
  3. How do you know when it’s time to go from learning from others by reading their books to taking action based on what you learned? I can listen to podcasts until I’m blue in the face and listen to everyone’s morning routine but at some point I have to pick what’s going to work for me — how can we think about when it’s the right time to stop reading and take action?
  4. Describe someone who you think has less to lose if they put themselves in uncomfortable situations than if they would stay the course in an ordinary life? Can ordinary ever be good? Where did you hear this message originally? How do you stop yourself from stopping yourself? Mel Robbins talks about the 5-second rule…ever try that?
  5. In your post, I Don’t Know How to Be a Good Father I heard some sadness around how those earlier days are now gone that your daughters are older. I read how you think it’s hard to ignite a fire in someone else to pursue their passions. So now, looking at where your daughters are and how they’ve turned out so far how do you think you did as a father? Does being a dad ever stop?
  6. What musicians or bands are on your playlist? Did learning how to DJ change that? Ever daydream as you listen to music? Maybe that you are someone else or doing things that you wouldn’t ordinarily do in real-life? I do hence I ask. When I daydream, I can breakdance like they did in that 1984 Breakdance movie.
  7. What advice would you have given your sons? Would it have sounded any different than the kind you have given to your daughters? I have three sons hence I ask. Side note: it’s interesting to me that James has two daughters and I have only sons. Curious, how our parenting styles have been shaped as a result of parenting only a member of the opposite sex? Something about this idea is compelling….extremely compelling to me. Perhaps, my psychology undergrad degree finds it fascinating…
  8. How did you prepare for your TEDxSanDiego talk? I have one coming up in March? I’m scared out of my mind. Any suggestions? I plan on documenting it via video. Yet, before then I want to see how Tim Urban documented or thought about his. Any favorite TED or TEDx talks you’d recommended me watching?
  9. In the 2017 documentary Becoming Warren Buffett, Warren says, “Wait till women discover, they’re the slaves of the world. My sisters were as smart as I was…but they got the message, a million different ways that their future was limited, and I got the message that the sky is the limit…” What are your thoughts as a dad to two daughters? My dad has two daughters.
  10. A big point of frustration is that I feel as if I did what I was told to ultimately land that big house. The messages I was fed was go to school and be a professional. My parent’s generation nor my grandparent’s generation thought about entrepreneurship as a good option. I think entrepreneurship to immigrants feels like the only option because they can’t fit into corporations. It’s like entrepreneurship out of necessity. How do you have this conversation with older generations who aren’t drinking this Kool-aid? I still want to make my dad proud?

#100daysofwriting #documenting #2018 #newyear

Subscribe to An Interview with Melissa Llarena the podcast. My plan is to interview talented people who figured out how to build untraditional careers of substance. My guests would have had the guts to say NO to traditional options, brains to make sometimes wacky interests profitable, and creativity to pull it all off.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Melissa Llarena

Melissa Llarena


I coach executives on how to dissect & deliver a perfect #jobinterview @TuckSchool Author of №1 #HR interview @Forbes @LinkedIn #mom