Fireside Chat: Amazon Fishbowl with Dorcas Cheng-Tozun

Jason Philip Yoong
4 min readMay 8, 2018

I had a fun, insightful, and peculiar chat with author Dorcas Cheng-Tozun at Amazon HQ in March 2018 about the intersection of startup life with marriage, family, and well-being. Regardless of your personal (single, dating, married, etc.) or professional (entrepreneur, freelance, full-time employee, etc.) status, I highly recommend her book Start, Love, Repeat: How to Stay in Love with Your Entrepreneur in a Crazy Start-up World.

Watch our chat below. In the spirit of continued transparency and to get better (let me know what other questions you recommend), I am sharing my list of questions below (after the neat photos, of course).

“Champion-in-chief” that is a title I like
Pump up the music!
Thank you Dorcas!
Do not lose sight of self-care when you are heads down on the business
I think we could have easily gone on for another hour!
I give the her book 5 stars. A must read.

Questions (in order):

  1. For audience members who have yet to read the book, how would you describe it?
  2. In the first chapter, you start the book off strong with the move to China. If you and your husband Ned had a young child during that time, how would that have changed your decision?
  3. You reference Action of Happiness, which is a movement of people taking action to create a happier society, and the 18 priorities such as family, friends, income, healthy, etc. in which the top six are essentials, middle six are nice to have and bottom six are non-essentials. How did your priority list change throughout the startup journey?
  4. In chapter eight, you describe the role of “champion-in-chief” to your entrepreneur partner, sharing that it is a partner’s responsibility to pull the other partner from the edge of the cliff when he is about to step off (Bill Reichert). What is an example of when you had to pull Ned from the cliff?
  5. In chapter 10, you cite a Pew Research Center study that found married couples rated the sharing of household chores as the third most important factor of a successful marriage, behind faithfulness and a happy sexual relationship, and that it ties in with coordination of logistics and responsibilities. What do you use currently to help coordinate your life?
  6. A piece I found critical is that active and reflective listening is a mandatory skill for every couple, for someone who wants to grow this skill, what advice would you give?
  7. In chapter 19, you cite that 90% of new ventures end up falling and the typical entrepreneur endures 3.8 failures before hitting upon a successful venture, you also share that grit is the most common trait successful individual’s share, grit being the passion and perseverance for very long term goals. How do you know if someone has grit, especially someone young and starting their first company?
  8. Along the topic of handling failure, you share that the ability to separate their ventures from their personal identities is the character trait most common in those who are best able to handle the demise of a business. For those of us who have a partner or a friend that does not separate these identities, what advice would you give?
  9. For myself, daily morning meditation has helped me be more present and stay calm during times of stress. What well-being techniques or daily practices do you recommend?
  10. Looking back at the journey, what did you learn about your husband Ned? What did you learn about yourself?
  11. In addition to Silicon Valley, you lived in China and Kenya, what specific lessons or practices did you experience there that you believe would be helpful for Silicon Valley entrepreneurs?
  12. I love this statement “the best antidote for resentment are curiosity and wonder” how do you stay curious?
  13. Final question before we get to audience Q&A, you have a room full of Amazonians, what is the one takeaway you want everyone to leave with?

Additional questions: (note: took a page from Tim Ferriss and his book Tribe of Mentors: Short Life Advice from the Best in the World, which I highly recommend in my 2017 book list)

  1. What books, besides your own, have you gifted the most to other people?
  2. What is the most worthwhile investment you have ever made?
  3. What have you become better at saying “no” to, and what approaches have worked for you?
  4. What purchase of $100 or less has most positively impacted your life in the last six months?
Read it!

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