Financial Freedom with Real Estate Investing

W-2 jobs give us a sense of security. But what happens if you lose your job or can’t work due to illness or injury? Spencer Hilligoss wanted to play financial defense and build enough passive income to keep the lights on for his family should something unexpected happen. And though real estate gets a bad rap for being a risky investment, Spencer discovered that multifamily is actually very predictable. In fact, it’s the best kind of boring! 

Spencer has 13 years of experience in tech startups, building high-performing teams across five companies—three of which valued at more than $1B. He currently serves as the Senior Director of Professional Development for LendingHome, the largest residential flip lender in the country. Spencer is also the Cofounder and Principal at Madison Investing, a real estate education platform dedicated to helping busy professionals build passive income, and a contributing writer and member of Forbes Real Estate Council.

On this episode, Spencer joins me to explain how the ‘dark decade’ he endured as a young man inspired him to pursue passive income through real estate. He shares his approach to financial planning, describing how he and his wife set goals and analyze deals together. Listen in for Spencer’s insight around the benefits of passive investing in multifamily over SFH strategies and learn exactly what he looks for in a sponsor, a market and a deal.

Key Takeaways

What’s keeping Spencer at his W-2 job

  • Take care of team at work
  • Don’t want to pull ripcord too soon

How Spencer got into real estate

  • Dad was top-performing real estate broker
  • Brother’s death + parent’s divorce led to bankruptcy
  • Pursue real estate to play defense financially

The Silicon Valley wealth playbook

  1. Join early stage tech startup for equity
  2. Work 16-hour days
  3. Pray for liquidity event
  4. Save for retirement (can’t access)

Spencer’s path to multifamily investing

  • Tech startup lends to real estate investors
  • Get educated and compare strategies
  • Built SFH portfolio of 7 (not passive)

How passive investing in multifamily differs from SFH

  • Analyze deal and build relationships up front
  • Double money in 5 years, don’t lift finger to manage

Spencer’s approach to financial planning

  • Based on being great parent, giving back
  • Work toward $8K/month passive income

What Spencer looks for in a sponsor

  • Track record (trustworthiness, grit, etc.)
  • Approach
  • Team
  • Communication

Spencer’s advice for new syndicators

  • Leverage partnerships and coaching
  • Borrow credibility from experienced investors

What Spencer looks for in a market

  • Strong job growth
  • Employers = counterweight to correction

What Spencer looks for in a deal

  • Specific plan to add value
  • Firsthand photos/videos beyond pro forma

What’s next for Spencer

  • More active to accelerate timeline
  • Scale impact through educational platform

Connect with Spencer Hilligoss

Madison Investing


Spencer on LinkedIn


Rich Dad Poor Dad: What the Rich Teach Their Kids About Money—That the Poor and Middle Class Do Not by Robert T. Kiyosaki


Department of Numbers

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Nighthawk Equity

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Financial Freedom with Real Estate Investing: The Blueprint to Quitting Your Job with Real Estate—Even Without Experience or Cash by Michael Blank

Direct download: ABI_186.mp3
Category:Commercial Real Estate -- posted at: 1:00am EST