127: Commercial Financing with John Matheson

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John Matheson is the CEO of Commercial Loan Success, a software and education platform designed to help small business owners and property investors make more informed financing decisions. Using the Commercial Loan Success loan analysis software platform, commercial borrowers and commercial lenders are able to communicate more effectively, and borrowers are able to approach commercial lenders more confidently, already knowing that their transactions are lendable. Through Commercial Loan Success, John hopes to provide the resources and educational materials that small business owners, entrepreneurs, and real estate investors can use to confidently obtain financing and grow their businesses profitably, all without being at the mercy of the predatory lenders.

John is also the managing member of J. Healy Development, LLC. The company specializes in developing new projects
into sustainable properties. John has been in the property development business for 26 years, and has been involved in
transactions for developing, permitting, and/or financing of completed projects totaling over $50 million. Through J.
Healy, John focuses on making multifamily, mixed-use, storage, and other commercial development properties more
green and sustainable, lessening a property’s footprint while increasing its value.

Key Points

  1. One of your most important partners – the lender!
  2. When a bank says no, go to the next one
  3. Being prepared to request a loan
  4. 3 things you need to provide to a bank – NOI, cap rate/appraised value, & debt service coverage ratio (DSCR)

Lightning Questions

  1. What was your biggest hurdle getting started in real estate investing, and how did you overcome it?
    • Mindset – when you’re starting out you’ll doubt yourself. You have to keep moving.When you get told no, go on to the next. Keep moving and never stop.
  2. Do you have a personal habit that contributes to your success?
    • John is stubborn. He keeps moving. John makes a plan and then is relentless in his approach.
  3. Do you have an online resource that you find valuable?
    • Slack.com
  4. What book would you recommend to the listeners and why?
  5. If you were to give advice to your 20 year old self to  get started in real estate investing, what would it be?
    • Spend more time with your family. Building a real estate business will take every minute if you let it. The deals will still be there.




Commercial Mortgages 101 by Michael Reinhard

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