Episode 18

Published on:

25th Jan 2021

Quitting Silicon Valley Tech Leadership To Helping Investors Build Passive Income - Spencer Hilligoss

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.

Spencer is a member of the 2021 Forbes Real Estate Council and a Registered Representative of Growth Capital Services, member FINRA, SIPC.

[00:0103:00] Opening Segment

  • I introduce and welcome our guest, Spencer Hilligoss
  • What's keeping him busy these days
  • Congratulating Spencer with his recently acquired broker's license

[03:0107:19] Spencer’s Story

  • Spencer talks about his journey to reach where he is today
  • He shares his background

[07:2014:19] Financial Offense and Defense

  • Spencer shares his perspective on financial offense and financial defense
  • Taking action and inaction 

[14:2026:06] Silicon Valley Tech Leadership

  • How he found himself joining the Silicon Valley Tech Industry and taking up leadership roles
  • The FOUR factors/steps in working at a tech company in Silicon Valley
  • Spencer shares his insights on coaching programs

[26:0731:06] Helping Investors Build Passive Income

  • Spencer talks about why he transitioned to a different career

[31:0738:30] Madison Investing

  • Spencer shares the story behind Madison Investing
  • He mentions what it's like starting a business with his spouse
  • He talks about what they do in Madison Investing
  • How they find and vet deals and take care of their investors

[38:3148:43] Passive Path To Financial Freedom

  • Spencer's take on the passive path to financial freedom
  • The biggest mistake real estate investors make

[48:4454:49] The Contrarian 3-Pack

  • What would you say is the most contrarian investment you've made?
  • Buying precious metals
  • What's your favorite activity to do with your friends and family outside of work?
  • Going to the park with my kids
  • What actions, whether within work or family, offer you the most fulfillment in life?
  • Hearing feedback from people that you have made a positive impact on
  • Get in touch with Spencer. See the links below.


Tweetable Quotes:

"I'm the anti-empire guy. What I want is full financial autonomy, geographical autonomy. I wanna be the best dad possible, the best husband possible, and live life on our terms." – Spencer Hilligoss

"Before you pay money to a person who's going to be educating you, take the time to ensure they actually have done the thing they are about to educate you on." – Spencer Hilligoss

"The single biggest mistake that real estate investors particularly make…is they breeze right by the notion that you have to pick the right strategy." – Spencer Hilligoss


Reach out to Spencer through LinkedIn or their website https://www.madisoninvesting.com/


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Think Different. Earn Different. Live Fulfilled.

Let’s stay Contrarian!

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About the Podcast

Contrarian Cashflow
Think Different. Earn Different. Live Fulfilled.
Have you ever thought there has to be more to offer from life?

I went to college....because they said that is what you do

I got a well paying job...because that is what they said to do

I reached Income and Net Worth goals....because that is what they said to do

As I attained each of those goals I didn't feel the change in myself I had expected. My life wasn't any different and it kept me wanting for more...

Who is they and why did I feel so compelled to listen??

After much introspection I have found relationships and fulfillment will lead to the most impactful life.

This podcast is about that journey, interviewing some of the most successful within investing and entrepreneurship. How we seek fulfillment in life and maintain motivation through life's ups and downs.

Please join us as we delve into becoming who you are meant to be.

About your host

Profile picture for John Blanton

John Blanton

John is an experienced sales professional and investor driven to help others surpass their goals and find fulfillment in life. He has a passion for gaining financial independence and helping others get there through investment cashflow. He is fortunate to be supported by his loving wife and two daughters. Favorite activities include spending time being active outdoors with his family.