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March 24, 2021 28 mins

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Spencer Hilligoss is an active syndicator, real estate investor, and executive leader. He leads business development, operations, and investor relations for Madison Investing.

Spencer is a technology leader with a 13-year track record of building high-performing teams across five companies - three of them, software "unicorns" - valued at more than $1B. He built and led the origination teams for LendingHome and led their Professional Development group.

 

[00:01 – 05:47] Opening Segment

  • Spencer speaks about things that he accomplished during this pandemic
  • He discusses how his real estate journey started

[05:48 – 16:54] Don't Quit Your Day Job Just Yet

  • Change your game plan accordingly – take charge of your own life! 
  • Spencer talks about his background
  • Before quitting your day job, listen to Spencer's advice on how you should work your way around this thought.

[16:55 – 22:38] Financial Literacy

  • Spencer shares that he wished he understood how to take charge of his own financial literacy earlier in his career
  • The biggest challenges Spencer is currently facing

[22:39 – 28:31] THE FINAL FOUR

  • What's the worst job that you ever had?
    • A part-time job during college. I worked for an author.
  • What's a book you've read that has given you a paradigm shift?
  • What is a skill or talent that you would like to learn?
    • I would like to be able to record and produce my own music.
  • What does success mean to you?
    • Optionality and being able to give back to others
  • Connect with Spencer. Links below

 

Tweetable Quotes: 

"As an investor, just get some more income streams whether it's active [or] passive. Just diversify a little bit. Build a side hustle." – Spencer Hilligoss

 

Resources Mentioned:


You can connect with Spencer on LinkedIn and at https://www.madisoninvesting.com/

 

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