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DreamNation Real Estate 26 – Damon Woodward: How To Create Win-Win Situations

“The first one is always tough.” This is true in so many levels, especially when it comes to real estate. If you are a newbie in this field, what things should you consider? What are the struggles that would come along the way? These are just some of the questions that our guest for today, Mr. Damon Woodward, would answer as he walks us down memory lane and tells us how he started his real estate journey.

Damon will share to us the basic principles of investment and the things we need to keep in mind to succeed in this venture. Whether you want to play it big or small, he has some tips and tricks for us to help us stay on the path of entrepreneurship.

But before anything else, let’s take a glimpse on Damon’s youth and see how these things have unveiled for him. In this episode, Damon talks about his humble beginnings living with his twin brother and mother. He had it simple and pretty much enjoyed his childhood alongside his peers.

Damon became a young entrepreneur when he started raking leaves on people’s lawn and got some money in return which he would use to buy the food that he likes. Little did he know that this mindset and experience would help make him successful today. From working on the mining industry for years to ultimately becoming successful in real estate, Damon is living proof that hard work, proper training, and patience always pays off in the long run. Now, he is ready to tell us the secret formula on how to transition to real estate.

How To Create Win-Win Situations Podcast – TImestamp

(1:19) Damon’s humble beginnings

(2:42) Damon shares about being a young entrepreneur

(4:57) Talks about being in a program for kids called SIL (Student Independent Living)

(5:13) Relates about how he owned a house at the age of 15 but gradually went downhill

(7:13) How his past experiences helped him develop the mindset he has now

(10:01) How he got into real estate

(11:16) How a man named Richard Dolan introduced him to real estate

(13:24) Talks about making connections along the way

(14:25) Damon tells us of the first-ever real estate deal he closed

(17:32) Tips for newbies on where to start in the real estate industry

(19:21) Talks about how to build relationships

(21:37) Tips and tricks on how to invest even if you don’t have the capital yet

(22:37) Never underestimate proper training and education about real estate

(24:40) Challenges that you might encounter along the way

(30:39) Damon talks about the buy-and-hold strategy for multifamily properties

(34:13) He shares about Black Card University and Stefan Aarnio

(40:30) Why it is essential to have a coach or mentor

Damon Woodward: How To Create Win-Win Situations?


Here’s what you have missed:

  • There’s nothing wrong with being an entrepreneur at a young age
  • A formula you can use to start a business
  • How to gain courage to do something alone
  • How and where to start for newbies
  • Tricks on how to invest without having the means or money
  • What the multifamily buy-and-hold strategy is




(4:24) I don’t think it was really about the money. I think I wanted to be respected. I think I wanted to just have a purpose.

(7:01) People that have a little bit of a colorful upbringing or a little bit of a colorful past—I’m finding now that they oftentimes make the best entrepreneurs.

(18:07) Try to flip first, even though wholesaling is still a really great place to start. But me personally, I started flipping right away.

(22:18) If somebody didn’t have access to any capital or any credit, try to find a strong relationship with somebody that does have access to either some capital or some credits and just present an idea to them about it.

(24:30) Even if you only had a 10% stake in a deal, you’re documenting your progress.

(25:20) The first one is always tough.

(32:41) It’s just about developing the skills and having a really good system in place to be able to manage some of the projects.

(33:48) As long as you just start small and start simple, then you can work your way out over a period of time and you don’t have to use any of your own resources or your own credit. But it certainly takes a little bit of work to learn.

(41:31) I was around people that were leveling up all the time. I was around people that were spending a ridiculous amount of money on their education. And I just started following the same pattern.

(43:17) No matter what happens, everything that we want is on the other side of something that is uncomfortable.



Damon Woodward Youtube: https://www.youtube.com/

Damon Woodward Facebook: https://www.facebook.com

Damon Woodward Instagram: https://www.instagram.com

Damon Woodward Website: https://www.damonwood

Blackcard University Website: https://blackcardu.com/

Damon Woodward LinkedIn: https://www.linkedin.com/in/



People mentioned:

Richard Dolan

Stefan Aaronic


Books mentioned:

Hard Times Create Strong Men – By Stefan Aarnio

hard-times-create-strong-men pdf/#:~:text=Hard%20



Money People Deal – By Stefan Aarnio




Lisitn My Real Estate Podcast




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