Photo by Nathan Dumlao on Unsplash

Is Wholesaling Really That Hard? (Answer: Nope)

I meet aspiring real estate investors every day, mostly through CTREIA. They also hit me up on Facebook, Instagram, and LinkedIn. I love hearing from and getting to know them.

That said, I hear it all the time. Every. Single. Day. ”Yeah but…”.

They are the Dreamers. I was one of them, not that long ago.

They know they want to break the shackles of their job, their debt, and their general dissatisfaction with their current life. But they won’t take ACTION to change.

“Yeah, but…”

So why do people find it so hard to get started? Here’s what I hear:

  • I don’t have enough money
  • I don’t have any time
  • I can’t find any deals
  • I’m afraid

These are all real reasons. The people who move forward are the ones who DECIDE their current situation is no longer acceptable. They DECIDE to make a change. Then, they ACT.

If I know anything about life and the real estate investing game, the difference between winning and losing is pretty simple…ACTION.

  1. Get your head right
  2. Educate yourself and/or find a mentor to model
  3. Take action
  4. Make mistakes, fix them and persevere

Sure, in the beginning, wholesaling can seem complicated, but it’s not. It’s the human being who is complicated.

When I signed my first deal, my hand shook, uncontrollably. I was more nervous to sign that piece of paper than the morning I got married.

I found my buyer on Craigslist, a week later, and assigned the contract to him. Then it happened. About a month later, the deal closed, and the attorney seated across the huge oak conference table handed me a check for $5,000. I was into the deal for $100!

I was off to the races.

I plowed that money back into my business. Cranked up my marketing and made sure everyone in my target market knew who I was and the problems I could solve for them.

Since that day in 2011, I’ve wholesaled many dozens of properties, I flipped even more through Clark St Homes. Clark St Properties now owns more than 100 rental units throughout New England.

Wholesaling is not complicated. You are. And that’s OK.

To overcome your “Yeah, buts” consider these:

1. I don’t have enough money.

You only need $100 to put a property under contract. If you need more or don’t have the $100, recruit a friend to partner on the deal. Money is easy to raise when you have a good deal, in-hand.

2. I don’t have enough time.

I worked an 80+ hour a week job when I did my first deal. I woke up 30 minutes early and searched for properties before work. I stopped watching TV and searched for properties after work. I searched for properties while I ate lunch. Can you find 30 to 60 minutes a day?

3. I can’t find any deals.

Call every For Sale By Owner (FSBO) listing. Search Craigslist. Search the pre-foreclosure listings on Zillow. Network with local family attorneys, bankruptcy attorneys, and accountants. Let them know you can help solve their clients’ financial issues by providing a fast, fair, all-cash offer for their properties.

4. I’m afraid.

Of course you are! People fear the unknown. Many fear failure. Some even fear success. You have to DECIDE you MUST (not should) make a change.

Remember, you’re not alone. Join your local Real Estate Investors Association. Partner with a friend you trust. Find a mentor. Hire a Coach.

The bottom line, Wholesaling is a simple process. It takes some work, but that won’t stop you, right?

You. Can. Do. This.

Overcome the negative self-talk. You deserve to be free of your job. You deserve to be free of your debt. You deserve to live life on your own terms. Don’t let anyone tell you this can’t be done. They’re wrong, and probably a little bit afraid.

Now what?


Press the “Go Button”, learn by doing, and fail forward.

When you do, reach out to me. I’ll probably buy the property from you.

Happy Investing!


CTREIA is the largest real estate investors & apartment owners association in the Northeast. We provide motivation, networking, funding, insurance, and coaching for investors in Connecticut and throughout the US.

If you are interested in learning more about becoming a CTREIA member or are interested in learning how to become a real estate investor, go to If you’re interested in funding your deals, go to If you’re interested in protecting your assets, go to




Dad, Husband, Coach, ‘Nova BBall fanatic w/an addiction to real estate. Founder @ Clark St Holdings & Co-Host of The Real Estate Underground podcast.

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Ed Mathews

Ed Mathews

Dad, Husband, Coach, ‘Nova BBall fanatic w/an addiction to real estate. Founder @ Clark St Holdings & Co-Host of The Real Estate Underground podcast.

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