057: Darrah Brustein | Kindred Spirits: Saving Hard and Playing Hard

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Today, my guest is fellow entrepreneur, lifestyle designer, and avid traveler Darrah Brustein. She shares the financial lessons she learned early in life, the impact they made, and how they helped her get to where she is today.

Darrah has such an incredible point of view, born from experiences like working for a company that went under right after purchasing her first home and starting a business with her twin brother. I personally loved the monthly check-in that Darrah and her partner use to tune in and get intentional in their relationship, and plan to incorporate that for Kim and I.

In This Conversation We Cover:

  • 1:00 Where Darrah grew up, and what it was like
  • 2:28 Money lessons learned early on in life
  • 5:27 Chores Darrah had growing up to learn financial health
  • 9:35 College, choosing majors, thoughts on the necessity of college
  • 15:31 Key lessons learned in working for a company that goes under
  • 17:11 Starting a business with her twin brother
  • 19:42 How Darrah set herself up to create passive income
  • 21:37 How outsourcing has helped in her business
  • 22:43 Network under 40, what it is and why it exists
  • 25:11 How to figure out what your strengths are and how to use them in a business
  • 26:54 How Darrah travels HARD
  • 30:07 Play funds and how Darrah financially prepares for travel
  • 35:14 Tuning in and getting intentional about her relationship
  • 39:00 Tony Robbins Morning Questions
  • 40:16 Darrah’s Davos invitation; the world economic forum
  • 42:15 PLAY HARD. How Darrah would like to add more play into her life
  • 44:45 Rapid fire
  • 46:44 What’s next: Darrah’s online 3 day Summit event

Darrah’s Relationship Check-In Questions

You can find more about Darrah’s intentional relationship strategies in her article, “You’ve Fallen In Love. Now What?”

  1. What’s something I can do more/less of to make you feel more loved?
  2. What was this month’s high/low point?
  3. What’s one thing I did this month that made you feel loved?
  4. Of what are you most proud of us as a couple? Of yourself? Of the other?
  5. What’s your biggest current worry; personally or professionally?
  6. What’s your goal/hope/intention for us over the next month?
  7. Random surprise question that’s fun and playful!

Tony Robbins’ Morning Questions

  1. What am I happy about in my life right now? What about that makes me happy? How does that make me feel?
  2. What am I excited about in my life right now? What about that makes me excited? How does that make me feel?
  3. What am I proud about in my life right now? What about that makes me proud? How does that make me feel?
  4. What am I grateful about in my life right now? What about that makes me grateful? How does that make me feel?
  5. What am I enjoying most in my life right now? What about that do I enjoy? How does that make me feel?
  6. What am I committed to in my life right now? What about that makes me committed? How does that make me feel?
  7. Who do I love? Who loves me? What about that makes me loving? How does that make me feel?

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Hi, I’m Rob!

Hi, I’m Rob! It has been said “You are not what you have learned, but what you’ve overcome.”


I have overcome my share of obstacles in order to architect the life of my dreams and uncover the key to lasting, meaningful success. Growing up in Queens (literally on the wrong side of the tracks), my early years were tumultuous, marked by hardship and violence.

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