39. Playing Financial Offense and Defense with Spencer Hilligoss

Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate syndicator partnering on over $800M in multifamily and self-storage assets under management. He is both a passive investor and active syndicator with a history in the financial technology industry. In this episode, Spencer discusses matching your investment strategy to your strengths, building your own investing criteria, and understanding the structure and value of the general partners in a syndication.

Spencer discusses financial offense and defense. He thought two large W2 incomes was enough but realized that multiple income streams would help insulate his family against the unknown.  That’s what he calls financial offense – things like adding income streams and setting clear financial goals.  Financial defense is thinking about creating maximum tax efficiency and expanding ones means rather than being completely focused on cutting costs.

Spencer explains how his fintech experience helped him prioritize personal finance and to see money as a tool.  This perspective also led to his transition from SFH’s to syndications. He also mentions that the operator, the market, and the deal are three critical things to look at for each syndication investment. He mentions that he thinks the strength, structure and experience of the operator are the most important parts to evaluate. Spencer stresses the importance of understanding the structure of the management group and what value each general partner is adding. He recommends third party evaluation of sponsors either through your network or getting references from people who have invested with them before. He discusses the importance of building your own criteria for what is important to you to get from the sponsor.

Podcasts he recommends:

Old Capital 

Bigger Pockets 

Financial Freedom with Real Estate Investing 


To connect with Spencer, go to www.madisoninvesting.com or LinkedIn.


If you would like to contact Jim Pfeifer, you can email him at jim@leftfieldinvestors.com or if you would like to find out more about Left Field Investors go to www.leftfieldinvestors.com


Our sponsor, Tribevest provides the easiest way to form, fund, and manage your Investor Tribe with people you know like, and trust.  Tribevest is the Investor Tribe management platform of choice for Jim Pfeifer and the Left Field Investors Community.  
Tribevest is a strategic partner and sponsor of Passive Investing from Left Field.  

Stay Connected!

Sign up to be notified of our latest articles and meeting announcements.