How to Start a Business While Working Full-Time & the Importance of Owning Your Misses with Spencer Hilligoss

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May 19 2020 53 mins   3

Spencer Hilligoss is an active syndicator, real estate investor and executive leader for two real estate businesses. His own company, Madison Investing, has co-sponsored deals totaling more than 4000 units for more than $500M.

He is also a former technology leader with a 13 year track record of building high-performing teams across five companies in Silicon Valley - three of them, software "unicorns" - valued at more than $1B.

In today’s episode, we discuss:

  • The various challenges Spencer faced when building Madison Investing while working full-time as a tech leader in Silicon Valley.
  • Taking ownership of building a growing team and having to lay multiple members off
  • Partnering with his wife
  • And much more!

To learn more about the Staying Power Collective, a group for aspiring and current virtual firm owners on a mission to grow their firms, visit

To read the show notes, guest contact information, and impactful quotes, visit