Weiss Advice

How To Work Less & Impact More with Divya Smith


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What happens when a tech executive discovers she can beat her financial advisor's returns by 5%? Divya Smith, founder of Ascending Avenue, shares her journey from 20+ years in Fortune 500 leadership to managing $300M+ in multifamily assets while helping others achieve financial freedom without sacrificing family time.

[00:00 - 07:00] From Corporate Technology to Real Estate Investing

  • 20+ years in technology leadership and executive roles at Fortune 500 companies
  • The unsettling realization that financial advisors didn't know as much as expected
  • Testing her investment skills: 19% returns vs advisor's 14% (minus fees)
  • How a LinkedIn connection who quit corporate for real estate sparked the transition


[07:01 - 14:00] Learning from Single Family Rental Mistakes

  • Managing one property with 5 tenants over 15 years - including police visits and drug issues
  • Being $600 below market rent due to discomfort raising prices on struggling families


[14:01 - 20:00] Building a Different Kind of Real Estate Business

  • Currently managing 3 investments per year (down from 4 to avoid burnout)
  • The importance of in-house property management and construction teams
  • Creating community through quarterly events: pizza parties, Halloween celebrations, Easter hunts
  • Why Class B multifamily became the sweet spot for investments


[20:01 - 29:00] Final Four & The Real Goal of Financial Freedom

  • Worst job: Asking for $9M in leftover funds for community initiatives - and being denied
  • Paradigm-shifting book: "Atomic Habits" by James Clear (re-read annually)
  • Skill to learn: Guitar (gifted 2 years ago, still waiting to be played)
  • Success definition: Helping others define their own success and touching 10,000 lives through career coaching


Connect with Divya:

Website: https://www.ascendingavenue.com

LinkedIn: https://www.linkedin.com/in/divyasmith/

Instagram: https://www.instagram.com/investwithdivya

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Key Quote:

"The goal is not to quit your job. The goal is to do what you love to do." - Divya Smith


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