Cornered By A 5'2" Realtor: The Deal That Started It All

After years of analysis paralysis, I finally became a real estate investor when my realtor forced me to sign on a four-family property. That first deal generated substantial rental income and sold for four times the purchase price, launching my journey from corporate employee to successful real estate investor.

• Spent 2.5 years analyzing over 1,100 deals without making a single offer due to fear
• Worked a demanding tech job with extensive travel while wanting to build real estate wealth
• Realtor Amy Rio confronted me and made me purchase a $99,000 four-family property
• That first property sold years later for over $400,000
• Built a sustainable strategy: flip houses to generate capital, then buy multifamily properties
• Continued working my day job for 7 more years while building my real estate business
• Developed systems for finding deals, managing contractors, and raising private money
• You don't need the perfect deal - you need to take action

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Chapters

• 0:00 Signing My First Deal
• 0:47 Welcome to Demo to Dollars
• 1:06 My Real Estate Journey Begins
• 2:39 Forced Into Action
• 5:06 Building a Flipping Business
• 6:53 Today's Key Takeaway

Transcript

Speaker 1: 0:00

Now Amy is generously about 5'2" and I'm more than a foot taller than her, but at that moment I was more afraid of Amy than I was of committing to the deal. My hand shook as I signed the document and in that moment, with that pen stroke, I became a real estate investor. Ever sat in your car scrolling through Zillow and thought, man, if I just knew where to start, I could flip one of these. Yeah, I've been there too. Most people who want to flip houses never even start, not because they're lazy, but because they don't have the blueprint. Well, that changes today. If you give me five minutes, I'll give you real world flipping strategies that actually work. No fluff, no theories, no gatekeeping, just real how-to information for you to apply today. Welcome back to Demo, to Dollars, your no BS flipping playbook, one tip at a time. Today I'm pulling back the curtain and sharing my story at least part of it how I went from red-eye flights and endless meetings that probably could have been emails to building a real estate business that changed my family's future. Let's get into it.

Speaker 1: 1:08

Back in 2008, a really good friend of mine gave me Robert Kiyosaki's Rich Dad, poor Dad and, like a lot of you, it lit a fire under me. I knew I wanted freedom and real estate felt like the way out. So I dove in headfirst. I read the books, I went to conferences, I talked to agents. I analyzed deal after deal after deal. I was busy but not productive, because after two and a half years I had nothing to show for it Zero properties. Here's why I didn't have the money. At least that's what I thought At the time. We had a toddler, a newborn, a wife who wanted to stay home with their girls. I was fully supportive of that, but we were barely making it. I had a mortgage that was a tech firm. I was flying 50 to 100,000 miles a year. I was gone 150 nights a year and living in hotels. Basically, on paper it looked great, but in reality the travel glamour wore off about 30 minutes into the first trip. I missed my girls, I missed my wife. So I spent every free moment I had soaking up time with them and I was caught in analysis paralysis, you know.

Speaker 1: 2:32

I looked back and it turns out I ran numbers on more than 1100 deals. I was looking for that perfect home run deal. That's what I thought. What actually was. The truth was, I was absolutely terrified and because of that fear I never even made a single offer. So while other investors were crushing it with flips and rentals, I was stuck on the sidelines by my own doing.

Speaker 1: 2:57

Then I met a local realtor named Damie Rio. She saw right through me. She called me a tire kicker from day one. One day she called and said I found a deal and I'm making you buy it. It was a four family in East Hartford, connecticut. It was listed at $99,000. It was a mess but most of it was cosmetic. So we walked through the property and she laid out the plan. You know about 15K more and it would be rent ready. I had enough in my savings for the down payment and rehab. But as we walked outside after the walkthrough I was all ready with my excuses. I didn't like the stained glass window in the stairwell. The landscaping was a mess, the porch was dirty.

Speaker 1: 3:40

Amy pretended to listen intently as she pulled out a purchase and sale agreement and put it on the hood of my truck and with that she put her hand up, stopping my speech mid-word. Amy pretended to listen intently as she pulled out a purchase order. Amy intend. Amy pretended to listen intently as she pulled out a purchase and sale agreement, put it on the hood of my car and then she put her hand up, stopping me mid-word. And then she put her hand up, stopping my speech mid-word. With that, she shoved a pen in my hand and said I've shown you over 20 properties. You always find an excuse and if you don't buy this one, I will Now sign the effin' document or never call me again. By the way. She didn't say effin', sign it. She said and this? She said sign it. She said this deal. She said sign it. She said this deal isn't perfect, but none are. This is a really good deal. You'll get cashflow and the property will appreciate. Now Amy is generously about 5'2" and I'm more than a foot taller than her, but at that moment I was more afraid of Amy than I was of committing to the deal. But at that moment I was more afraid of Amy than I was of committing to the deal. My hand shook as I signed the document and in that moment, with that pen stroke, I became a real estate investor.

Speaker 1: 5:06

Now, fast forward. That little four family has generated tens of thousands of dollars in rental income for me and my family and, frankly, I sold it last year for over $400,000. That first deal changed everything. From there, I stacked base hits, mostly singles and doubles. I'd flip a house or two, make the money from them and then buy a multifamily, rinse and repeat, rinse and repeat. And I got smarter about the business operation. I built systems for finding and managing deals, for finding and managing good contractors. I learned how to spot bad ones and fire them fast. And I also learned how to raise money and work with private lenders. And that's when it really started to take off. Piece by piece, flipping became less of a side hustle and more of a business.

Speaker 1: 5:56

And here's the truth most people don't want to hear. I didn't quit my job day one. In fact, I worked for another seven years. I flipped nights and weekends. I made mistakes, I fixed them, but I didn't leave my day job until I had a sizable chunk of money set aside and I got a little nudge. More on that in a future episode.

Speaker 1: 6:18

So if you're stuck in the same spot I was in, successful on paper but desperate for freedom, this podcast is your shortcut. I've made the mistakes so you don't have to, and I desperately want to help you. All right, let's wrap it up. Here's today's takeaway. You don't need the perfect deal. You don't need permission, you need a plan and you need some guidance. Take action, find the deals, run the numbers and make offers, get in the game and stay in the game. If I can do it, so can you. This is Demo to the Dollars. I'm Ed Matthews. Catch you on the next one. This is Demo to Dollars. I'm Ed Matthews. Catch you on the next one. Thanks for listening to Demo to Dollars. If today's episode helped you move one step closer to your first or next deal, do me a favor follow us wherever you get your podcasts so you never miss a show. I'm grateful to be part of your journey. Now get out there and get cracking. Bye for now.