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Sometimes the best business decision is knowing when to let go. Amy Calandrino, founder of a commercial real estate brokerage, shares her journey from hammering in her own signs during the 2010 recession to building a team of nearly 10 advisors—and why she ultimately chose to close her firm to join Cushman & Wakefield. In this episode, Amy reveals the hidden costs of entrepreneurship, the importance of aligning your work with your values, and how she's redirecting her energy toward meaningful impact through her family foundation's financial literacy programs.

[01:05 - 04:10] From Vermont to Orlando: Building a Career on Grit

• Started working full-time at age 13 and put herself through college debt-free
• Worked alongside her husband in a law office where she learned about commercial real estate

[04:25 - 07:20] The Hidden Costs of Running a Brokerage

• Founded her brokerage in 2010 during the economic downturn with a shoestring budget
• Grew from solo founder to nearly 10 advisors by 2022

[07:21 - 11:45] Making the Leap: Consulting the Best in the Business

• Sought advice from industry leaders Sarah Malcolm, Allison Weiss, and Beth Azor
• Realized she could still be an entrepreneur without owning a brokerage

[11:46 - 19:30] The Three-Month Transition and Its Unexpected Lessons

• Spent 90 days transitioning clients and wrapping up her brokerage
• Experienced grief despite making the right decision

[19:31 - 27:15] Redirecting Energy: The Aspiring Entrepreneur Program

• Founded a family foundation with her husband to give back to the community
• Created an entrepreneurship program for elementary school students

[27:20 - 31:50] Final Four & How to Connect

Connect with Amy:

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

Email: Amy.Calandrino@cushwake.com

Book: "From Perfect to Real" (available on Amazon)

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"Success to me is serving my clients in the best way possible and knowing each and every day that I've put forth the most amount of effort that I can. I never want to p

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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

LEAVE A 5-STAR REVIEW by clicking this link.

WHERE CAN I LEARN MORE?

Be sure to follow me on the below platforms:

Subscribe to the podcast on Apple, Spotify, Google, or Stitcher.

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www.yonahweiss.com

None of this could be possible without the awesome team at Buzzsprout. They make it easy to get your show listed on every major podcast platform.

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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What happens when a Hollywood producer trades movie sets for multifamily properties? Michael Jacobs, founder of Mar Vista Entertainment (sold to Fox Studios), shares his transition from 25 years in entertainment to building a vertically integrated real estate empire in Pittsburgh.

[00:01 - 08:05] From Hollywood Producer to Real Estate Investor

• Built Mar Vista Entertainment from a 2003 business plan to Fox Studios acquisition
• Specialized in $5M-and-under movie production for Netflix, Disney Channel, Lifetime
• The decision to transition away from Hollywood's demanding travel schedule
• Started with three duplexes to test the rental market in Pittsburgh's Squirrel Hill

[08:06 - 15:40] Building a Vertically Integrated Real Estate Business

• How frustration with general contractors led to building an in-house construction team
• The challenge of 100-year-old infrastructure: cast iron pipes, knob-and-tube wiring
• Expanding from rental properties to becoming one of Pittsburgh's premier design-build firms
• Why complete gut renovations became the standard approach for old housing stock

[15:41 - 22:10] The "Singles and Doubles" Business Philosophy

• Why avoiding the pressure for home runs and grand slams builds sustainable businesses
• The danger of social media hype and "get rich quick" mentalities
• How to test, measure, and scale gradually while watching the numbers
• Balancing tenant satisfaction with property upgrades to reduce turnover

[22:11 - 28:40] Final Four & Building for the Future

• Worst job: Cleaning motel rooms for $6/hour time-and-a-half on Sundays
• Paradigm-shifting book: "Buy Back Your Time" by Dan Martell
• Skill to learn: Guitar (joining the ranks of aspiring musical entrepreneurs)
• Success definition: Providing for family and keeping nine children and two grandchildren happy

Connect with Michael:

Website: https://marvistadb.com
LinkedIn: Michael Jacobs

LEAVE A 5-STAR REVIEW by clicking this link.

WHERE CAN I LEARN MORE?

Be sure to follow me on the below platforms:

Subscribe to the podcast on Apple, Spotify, Google, or Stitcher.

LinkedIn

Youtube

Exclusive Facebook Group

www.yonahweiss.com

None of this could be possible without the awesome team at Buzzsprout. They make it easy to get your show listed on every major podcast platform.

Tweetable Quotes:

"The numbers drive everything at the end of the day. " - Michael Jacobs

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