How to Overcome Fear & Ask for What You Want (or the Time I Made $30K in 6 Weeks)

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There are monumental moments in life we will never forget: in life, in business and with our family and our children.

For me, there was one such moment during a deal that came together where I made the most money I had ever made in a real estate deal to that point — and having been a poor musician for many years, it was likely close to or even more than what I had made on a yearly basis the first few years out of college.

This post is about musings. About fun. It’s about living a little bit. Enjoying life. Asking for what you want…and being prepared to act on what you get.

It’s not just important, I think, to ask for what you want and to be prepared for what you ask for — to me, it is fundamental to your life and your business. 

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The Deal

I had already known the sellers, a doctor and his wife, who lived the wildly awesome lifestyle — with BMW convertibles, a large Southwest Florida home and the best of everything.

Related: How I Overcame Fear, Age, and Lack of Experience to Become a Successful Real Estate Investor

The home had incredible landscaping and a perfectly lit courtyard with a pool, and it was enclosed on three sides with floor to ceiling glass, which offered a view from the living room, dining room and kitchen. And of course it was perfectly decorated. It featured a vaulted roof over the pool, as well as a cabana house next to the residence with kid’s playroom, workout room and a giant office with a desk the CEO of IBM would have coveted.

They paid way too much for the house in the first place — and to make matters worse, it was during the years of complete cataclysmic economic disaster and the eventual crash of the real estate market in the late 2000’s. The situation was of course not compounded at all by their need to spend $2 dollars for every $1 they made. Their house, having been purchased for over a million dollars, was sold to us for less than half that.

The Importance of First Impressions

Let me digress for a moment…

When I first started as a real estate agent in Florida, I would (be required to) attend these big gatherings for new realtors (yawn) for ya-ya-rah-rah…education and all the hours of don’t-do-this-don’t-do-that with all these realtors.

Especially, say, the first meetings when they pile all 100-200 of the new realtors in a room together, give you the big pep talks, hear from these wildly successful agents — and you either leave there fired up or you leave feeling it is entirely impossible to measure up.

One of the interesting things for me was as I would meet a successful investor or real estate agent, I noticed that they were always well dressed, and they almost always…had a sweet watch. Seriously, is that ANOTHER #Rolex!? Yeah. It was.

Maybe I was (overly) obsessed with the watch part.

Maybe I still am.

But it was a clear indication on their part of, “I know what I am doing. I am successful. I can get the deal done.” 

You know when you meet someone, when you feel their very presence, the weight of their passion, the fight and drive they have for their business? This made a huge impression on me. And I continued to keep my eyes open as to how the best realtors acted, how they dressed, how they showed up to appointments and how they closed their deals (or at least the ones I could go read about, ask questions about or being on the other side of the deal as the other realtor).

So anyway, wandering words aside…

When we walked up to the doctor’s house, we were prepared. We were dressed well, like guys who could actually close on an almost $500k cash deal. My partner with his Rolex Yachtmaster and myself, pretty sure wearing something from the local mall (yeah, it wasn’t expensive or glamorous, but it was the best I had).

My partner and I role played through how the deal would go down. The questions the sellers would have. And the questions we expected they would need to answer for themselves to feel comfortable and agree to our offer. We came in, made a cash offer and put the house under contract.

It was a killer deal for us, and it got the sellers out of their terrible situation.

Closing the Deal

After doing very little work and listing the house on the market, we sold the house in about 6 weeks from start to finish. I will never forget that day. I remember my partner showing up to my house; I remember the look on his face. I remember it like it happened today.

He took out his checkbook and wrote me the check. It had more zeros oin it than I had ever seen on a check before. After our expenses of money, I had made just shy of $20k on the flip. And another $10k as the realtor on the deal. He had funded it and made more on it that I did. There was well over $60k profit in the deal.

The After Celebration

For fun that following weekend, my wife and I decided to do a little shopping and have a wonderful dinner to celebrate — so we headed into the mall just a mile or so from the beach. I had had my eyes on a pair of sunglasses. I showed them the pair of Ray Bans I wanted and asked what kind of deals they were running. Of course, it’s Sunglass Hut, and they don’t run deals.

I kindly asked again. And maybe a few times. Joking, but serious. I didn’t need to buy them, but I would get them if I could get a little better deal. At that point, the salesperson asked me if I had the special coupon that I guess only a few special customers had received. I smiled back and said, “Sure I do.” The salesperson responded, “Great!”

Guess what, I saved about 30% on the glasses. I walked out happy. Deal done. I paid cash. They had a sale. Probably still made like 80% profit on those things, anyway.

Then we walked directly to Macy’s, and I told my wife she should pick out whatever purse she wanted. She picked out a supple dark brown leather Dooney and Bourke bag and promptly walked away. See, she likes the deals we get, but she get’s a little squirmy when negotiation goes down. Like, duck and cover.

Meanwhile, I LIVE for it. #likeaboss

Anyway, I walked up to the clerk there, and for the second time that evening — batting 1000 baby — I asked what kind of deals they had going. She said they didn’t have any sales going. Shocking. I set the purse on the counter, and I could see — well, there was no one in the store, no sales happening, at least anytime soon. I asked again, what else could she do?

Guess what. A phone call later, a coupon appeared; she scanned it, and we saved 20%. Thanks Macy’s and Sunglass Hut sushi dinner tonight on you guys.

I literally try and negotiate with the checker at the local grocery store. And the guy who owns the gym for t-shirts. And the car salesman (only buy when you have the sales manager or owner at the table trying to close the deal!).

I love every second of it. And the answer is always NO if you don’t ask. Seriously, tonight as you are putting your organic peanut butter and box of fancy crackers to finish your supper shopping on the counter, ask for a discount from the checker at your grocery story. If nothing else, you both will get a little laugh. And you will get practice at asking for a good deal.

My favorite line when I am with my son or a buddy is to ask for a “two-good-looking-dudes discount.” It’s sure to get the eyebrow raise and some laughs. Make sure you ask at least twice. 🙂

Remember: If you don’t ask for a deal, then the answer is always “no.”

My First Big Boy Watch

Something like a week or two after the deal had closed, we headed out on a last minute cruise. We didn’t buy any fancy room; we actually bought our room for around $100 a person (got a deal from an online last minute cruise site, and we paid cash using our debit cards for our business account).

Who spends their time in their room anyway? Not us.

One of our favorite things to do on cruise ships is to go to their specialty restaurants. They are usually a LOT better than the regular dining room, and they treat you like kings and queens in there. Just a few tables, awesome food (that isn’t cooked for 2,000 people at once) and great service. It’s basically the same price you would have paid going out to dinner anywhere else, except you have two waiters for your table — and an ocean view.

On one of our excursions we went shopping on an island, and we walked into a jewelry shop.

Sure enough, I found this beautiful large-faced silver watch with this perfect leather strap that had a clasp/lock mechanism. It wasn’t a Rolex, but it was my first real watch. A Bulova with automatic movements — and the sexiest-looking watch I’d ever had on my wrist.

I fell in love with it and decided to just go for it. It wasn’t Rolex money, but it was certainly the most I had ever spent on a watch — and probably more than I’d spent on my first car. But why not? I had just made almost $30k in 6 weeks, and I could afford it. I didn’t have to put it on a credit card, and I loved the way it made me feel when I put it on.

Related: Newbies: Is Fear Holding You Back? Read This!

My wife officially said it was my anniversary present, and therefore I had to get it, which made it all the more special.

The Point

I wear my watch as a reminder that I can do anything I put my mind to. Actually, I’m literally sitting in the booth of a Einstein Brother’s wearing a hoodie, a #ROYALS baseball cap — and my awesome watch…because my stupid internet is down, and when I have a deadline..or a deal…or an appointment, I won’t let a little challenge keep me from making my deadline or getting the deal done.

Anyway, a watch by itself isn’t going to bring you happiness. Or luck. Or success. But the process of earning and buying a watch (or a car or a house) — that’s the point. This year, my family was able to turning our real estate business into a venture that allowed my wife to quit her job and stay home. This is what it’s about. Real estate investing is about opportunity and belief in yourself.

So take your well-pressed shirt, your killer shoes and the best dress watch you have, and put them on. Walk out the door with purpose and the knowledge in your heart you can make whatever goal or dream you have come to fruition. You just have to put the pieces together, to ask for what you want — and be fully prepared to get what you ask for.

What’s your dream, your desire? And what are you doing to work towards it?

I want to hear your stories! Please comment below. 

About Author

Nathan Brooks

Nathan Brooks is the co-founder and CEO of Bridge Turnkey Investments, a Kansas City-based company renovating and selling more than 100 turnkey properties per year. With over a decade of experience in real estate, Nathan is a seasoned investor with a large personal portfolio and a growing business portfolio. Just last year, through Bridge Turnkey Investments, he helped investors add over $12 million in value to their real estate portfolios. Nathan regularly produces educational content to fuel his passion for helping other people learn about and find success in real estate investing. He has been featured regularly on industry podcasts such as the BiggerPockets Podcast, Active Duty Passive Income Podcast, Freedom Real Estate Investing Podcast, Fearless Pursuit of Freedom Podcast, Titanium Vault, The Real Estate Investing Podcast, The Best Real Estate Investing Advice Ever Show, the Good Success Podcast, FlipNerd, Wholesaling Inc., The Real Estate Investing Profits Master Series, Flipping Junkie Podcast, Flip Empire podcast, Think Realty Radio, and more. He is a sought-after speaker and writer and can be found on stage regularly at events across the country.


  1. This article struck a cord with me. I just went into contract selling my first flip. After I split with my business partner I’ll clear 11g’s. I get the watch thing and the feeling of this is for real. I’m a realtor and I like doing deals and helping people but this one is special. Can’t wait to flip another!

  2. Nathan –

    What a great story! I love stories. It’s amazing what a difference “dressing the part” can do for your mental state. Someone once told me that in business you should dress for the job you aspire to have one day.

    I think the way you project yourself can make or break a negotiation. Sometimes the way you look makes you feel confident and that fuels your success. Great post.


    • Nathan Brooks

      Thanks Sharon! Dressing the part is EXACTLY right. That way we feel good, therefore our minds our set on the job at hand … whether it’s dealing with a contractor or negotiating a deal.

      Thanks for reading and taking the time to post Sharon!

    • Nathan Brooks

      Thanks Shane!

      It was a fun couple weeks, thats for sure! Thanks for taking time to read and respond!! I hope that sharing my stories just remind people (and myself) that we can accomplish something when we put our minds to it. Let’s get after it!!

  3. Frankie Woods

    I’ve been wanting that nice watch for ten years! But, every time I save up to buy one, I just keep saving and end up investing in something…

    I am going to have to take your approach at looking at every interaction as a potential deal. It’s funny, but man, it is so powerful to developing yourself as a business person. Great stuff!

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