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Straight Up Chicago Investor Podcast Episode 202: Challenging Househacks With Sewer Lines, Evictions, And Gangs…oh My! With Ben Sussman

Straight Up Chicago Investor Podcast Episode 202: Challenging Househacks With Sewer Lines, Evictions, And Gangs…oh My! With Ben Sussman

Our latest podcast episode features Ben Sussman, a real estate investor who has acquired 12 investment properties before the age of 30. While building a real estate portfolio at a young age may sound glamorous, Ben gave us a raw, unfiltered look at the challenges he has faced and the hard-won lessons he has learned along the way.

Ben got into real estate investing because he was attracted to the cash flow and tax benefits. He started by purchasing properties in up-and-coming neighborhoods like Belmont Cragin and Back of the Yards in Chicago. However, his first investment quickly turned into a nightmare when a broken sewer line caused major damage. Despite the obstacles, Ben persevered and continued building his portfolio.

His second project proved even more difficult when he inherited a tenant involved in gang activity who threatened Ben with violence multiple times. Ben explained how he navigated this dangerous situation and was eventually able to resolve it.

While the road to becoming a real estate investor has been far from easy, Ben said the positives have far outweighed the negatives. Ben's story is a testament to the power of perseverance and maintaining a long-term mindset as a real estate investor.

Despite the challenges, Ben has built a thriving real estate business and a 12-door portfolio before the age of 30. For anyone interested in real estate investing, Ben's episode is a must-listen. He provides invaluable advice for finding good deals, overcoming obstacles, and building wealth through real estate.

Ben's story is a raw, unfiltered look at what it really takes to become a successful real estate investor at a young age. While the road is far from easy, Ben proves that with hard work, perseverance, and the right mindset, anyone can achieve their real estate investing goals and build a life-changing portfolio.

Questions We Answer In this Show:

Q. Real Estate Investment: A Journey of Learning and Growth

Q. Cash Flow Challenges and Estoppel Agreements in Real Estate Investing

Q. Real Estate Horror Story: Taking the Leap of Faith and Dealing with Unexpected Expenses

Show Notes:

  • 04:19 Housing Provider Tip: Be mindful that source of income has been added to the Fair Housing Protected Classes and cannot be discriminated against!
  • 07:50 Intro to our guest, Ben Sussman!
  • 09:23 How did Ben get started in real estate?
  • 13:28 Ben talks about the neighborhoods he started investing in and his first acquisition!
  • 22:52 Lessons learned on Ben’s first property!
  • 25:12 Why did Ben go from Belmont Cragin to the Back of the Yards neighborhood for this second project? 
  • 33:18 Did Ben account for the added risk when acquiring his second property in a lower class neighborhood?
  • 38:05 How did Ben get out of the situation with his hostile, gang-member tenant?
  • 42:39 Ben summarizes the lessons learned on this second property!
  • 58:16 What is Ben's competitive advantage? 
  • 59:07 One piece of advice for new investors.
  • 59:49 What do you do for fun?
  • 61:15 Good book, podcast, or self development activity that you would recommend? 
  • 62:07 Local Network Recommendation?
  • 64:08 How can the listeners learn more about you and provide value to you?

Guest Name: Ben Sussman

Guest Company: Exit Realty

Guest Link:

Realtor Inquiries:

Other Links for show notes:

The Almanack (Book Recommendation)

Retire Early with Real Estate Investing (Book Recommendation)

Alan Sussman (Insurance Agent Facebook)

Alan Sussman 

Ben's Instagram

Chicago Investor Resources Shared

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